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WO2005077345A1 - Compounds for the treatment of gastro-esophageal reflux disease - Google Patents

Compounds for the treatment of gastro-esophageal reflux disease Download PDF

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Publication number
WO2005077345A1
WO2005077345A1 PCT/US2005/000336 US2005000336W WO2005077345A1 WO 2005077345 A1 WO2005077345 A1 WO 2005077345A1 US 2005000336 W US2005000336 W US 2005000336W WO 2005077345 A1 WO2005077345 A1 WO 2005077345A1
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WO
WIPO (PCT)
Prior art keywords
triazol
phenyl
methyl
chloro
ylsulfanylmethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2005/000336
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French (fr)
Inventor
Anders Lehmann
Jan Mattsson
Karolina Nilsson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AstraZeneca AB
Shire NPS Pharmaceuticals Inc
Original Assignee
AstraZeneca AB
NPS Pharmaceuticals Inc
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Publication date
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Publication of WO2005077345A1 publication Critical patent/WO2005077345A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/04—Drugs for disorders of the respiratory system for throat disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to the use of certain compounds for the inhibition of transient lower esophageal sphincter relaxations.
  • a further aspect of the invention is directed to the use of certain compounds for the treatment of gastro-esophageal reflux disease.
  • the lower esophageal sphincter (LES) is prone to relaxing intermittently. As a consequence, fluid from the stomach can pass into the esophagus since the mechanical barrier is temporarily lost at such times, an event hereinafter referred to as "reflux".
  • Gastro-esophageal reflux disease is the most prevalent upper gastrointestinal tract disease. Current pharmacotherapy aims at reducing gastric acid secretion, or at neutralizing acid in the esophagus. The major mechanism behind reflux has been considered to depend on a hypotonic lower esophageal sphincter. However, e.g. Holloway & Dent (1990) Gastroenterol. Clin. N. Amer. 19, pp. 517-535, has shown that most reflux episodes occur during transient lower esophageal sphincter relaxations (TLESRs), i.e. relaxations not triggered by swallows. It has also been shown that gastric acid secretion usually is normal in patients with GERD.
  • TLESRs transient lower esophageal sphincter relaxations
  • the object of the present invention was to find a new way for the inhibition of transient lower esophageal sphincter relaxations (TLESRs), thereby preventing reflux. More particularly the object of the invention was to find a new way of treating gastro-esophageal reflux disease (GERD), as well as a new way for the treatment of regurgitation.
  • GGERD gastro-esophageal reflux disease
  • the present invention is directed to the use of compounds of formula la
  • P is selected from the group consisting of hydrogen, C 3 . 7 alkyl or a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S;
  • R 1 is selected from the group consisting of hydrogen, hydroxy, halo, nitro, C ⁇ alkylhalo, O . 6 alkylhalo, C ⁇ alkyl, OC ⁇ alkyl, C 2 . 6 alkenyl, OC 2 . 6 alkenyl, C 2 . 6 alkynyl, OC 2 . 6 alkynyl, C 0 .
  • M 1 is selected from the group consisting of a bond, C ⁇ alkyl, C 2 . 3 alkenyl, C 2 . 3 alkynyl, C 0 .
  • X 1 , X 2 and X 3 are independently selected from the group consisting of CR, CO, N, NR, O and S;
  • R is selected from the group consisting of hydrogen, Co- 3 alkyl, halo, Co. 3 alkylOR 5 , C 0 . 3alkyl R 5 R 6 , C 0 . 3 alkyl(CO)OR 5 , C 0 - 3 alkylNR 5 R 6 and C 0 . 3 alkylaryl;
  • M 2 is selected from a group consisting of a bond, d ⁇ alkyl, C 3 . cycloalkyl, C . 3 alkenyl, C 2 .
  • Q is a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S, which group may optionally be fused with a 5- or 6- membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S and which fused ring may be substituted by one or more A;
  • R 5 and R 6 are independently selected from the group consisting of hydrogen, hydroxy, d- 6 alkyl,
  • R 6 may together form a 5- or 6-membered ring containing one or more atoms independently selected from the goup consisting of C, N, O and S; wherein any d- 6 alkyl, C 2 . 6 alkenyl, C 2 . 6 alkynyl, Co- 6 alkylC 3 . 6 cycloalkyl, C 0 . 6 alkylaryl and C 0 .
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may be substituted by one or more A;
  • A is selected from the group consisting of hydrogen, hydroxy, oxo, halo, nitro, Co- 6 alkylcyano, d. 4 alkyl, Co- alkylC 3 . 6 cycloalkyl, d- ⁇ alkylhalo, Od- ⁇ alkylhalo, C 2 . 6 alkenyl, Od_ 6 alkyl, C 0 .
  • TLESRs transient lower esophageal sphincter relaxations
  • the present invention further provides the use of a compound of formula I
  • P is selected from the group consisting of thiophene, pyridyl, thiazolyl, furyl, pyrrolyl and phenyl, whereby the phenyl ring is substituted on position 3 or disubstituted on positions 2 and 5;
  • R 1 is attached to P via a carbon atom on ring P and is selected from the group consisting of hydrogen, hydroxy, halo, nitro, C ⁇ . 6 alkylhalo, Od. 6 alkylhalo, d. 6 alkyl, Od. 6 alkyl, C 2 . 6 alkenyl, OC 2 . 6 alkenyl, C 2 . 6 alkynyl, OC 2 .
  • M 1 is a bond
  • X 1 selected from the group consisting of C, CO, N, O and S;
  • X 2 is selected from the group consisting of C, N, O and S
  • X 3 is i) selected from the group consisting of N, O and S, or ii) selected from N, O, S, and C when X 2 is selected from N, O, or S, and when X 3 is C the substituent R on X 3 is H. ;
  • R is selected from the group consisting of hydrogen, C 0 - 3 alkyl, halo, C 0 - 3 alkylOR 5 , C 0 .
  • M 2 is selected from a group consisting of a bond, d- 3 alkyl, C 2 . 3 alkynyl, C 0 - 4 alkyl(CO)Co- 4 alkyl,
  • X 4 is selected from the group consisting of Co- 4 alkylR 5 R 6 , C 3 _ 7 cycloalkyl, C 1 . 4 alkyl(NR 5 R 6 ),
  • Q is i) selected from the group consisting of triazolyl, imidazolyl, oxadiazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, and wherein any substitutable nitrogen atom in the ring is substituted with R 4 on such nitrogen atom and any suitable carbon atom is optionally substituted with R 4 ; and
  • R 5 and R 6 are independently selected from the group consisting of hydrogen and d. 6 alkyl; wherein any d- 6 alkyl defined under R 1 , R 2 and R 4 may be substituted by one or more A ;
  • A is selected from the group consisting of hydrogen, hydroxy, halo, nitro, oxo, C 0 . 6 alkylcyano, Co. 4 alkylC 3 . 6 cycloalkyl, C ⁇ _ 6 alkyl, d. 6 alkylhalo, Od. 6 alkylhalo, C 2 . 6 alkenyl, C 0 - 3 alkylaryl, Co-
  • TLESRs transient lower esophageal sphincter relaxations
  • the present invention further provides the use of a compound of formula lb
  • P is selected from the group consisting of thiophene, pyridyl, thiazolyl, furyl, pyrrolyl and phenyl, whereby the phenyl ring is substituted on position 3 or disubstituted on positions 2 and 5;
  • R 1 is attached to P via a carbon atom on ring P and is selected from the group consisting of hydrogen, hydroxy, halo, nitro, d. 6 alkylhalo, Od- ⁇ alkylhalo, d. 6 alkyl, Od- ⁇ alkyl, C 2 - 6 alkenyl,
  • M 1 is a bond
  • X 1 selected from the group consisting of C, CO, N, O and S
  • X 2 is selected from the group consisting of C, N, O and S
  • X 3 is selected from the group consisting of N, O and S, or X 3 is CH when X 2 is N, O or S;
  • R is selected from the group consisting of hydrogen, Co- 3 alkyl, halo, Co- 3 alkylOR 5 , Co-
  • M 2 is selected from a group consisting of a bond, C M alkyl, C 2 . 3 alkynyl, Co- 4 alkyl(CO)C 0 - 4 alkyl, C 0 - 3 alkylOCo- 3 alkyl, Co-3alkylNR 5 d. 3 alkyl, C 0 . 3 alkyl(CO)NR 5 , C 0 . 4 alkylNR 5 , Co- 3 alkyl(SO)C 0 .
  • X 4 is selected from the group consisting of Co- alkylR 5 R 6 , C 3 . 7 cycloalkyl, C 1 . 4 alkyl(NR 5 R 6 ),
  • Q is i) selected from the group consisting of triazolyl, imidazolyl, oxadiazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, and wherein any substitutable nitrogen atom in the ring is substituted with R 4 on such nitrogen atom; and
  • R 5 and R 6 are independently selected from the group consisting of hydrogen and d- 6 alkyl; wherein any d. 6 alkyl defined under R 1 , R 2 and R 4 may be substituted by one or more A ;
  • A is selected from the group consisting of hydrogen, hydroxy, halo, nitro, oxo, Co- 6 alkylcyano,
  • TLESRs transient lower esophageal sphincter relaxations
  • alkyl includes both straight and branched chain alkyl groups and may be methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, t-pentyl, neo-pentyl, n-hexyl or i-hexyl, t-hexyl.
  • Ci- 3 alkyl refers to an alkyl group having 1, 2 or 3 carbon atoms, and may be methyl, ethyl, n- propyl and i-propyl.
  • cycloalkyl refers to an optionally substituted, saturated cyclic hydrocarbon ring system.
  • C 3 . 7 cycloalkyl may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • alkenyl includes both straight and branched chain alkenyl groups.
  • C 2 - 6 alkenyl refers to an alkenyl group having 2 to 6 carbon atoms and one or two double bonds, and may be, but is not limited to vinyl, allyl, propenyl, i-propenyl, butenyl, i-butenyl, crotyl, pentenyl, i-pentenyl and hexenyl.
  • alkynyl includes both straight and branched chain alkynyl groups.
  • aryl refers to an optionally substituted monocyclic or bicyclic hydrocarbon ring system containing at least one unsaturated aromatic ring. Examples and suitable values of the term “aryl” are phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, indyl and indenyl.
  • heteroaryl refers to an optionally substituted monocyclic or bicyclic unsaturated, aromatic ring system containing at least one heteroatom selected independently from N, O or S.
  • heteroaryl may be, but are not limited to thiophene, thienyl, pyridyl, thiazolyl, furyl, pyrrolyl, triazolyl, imidazolyl, oxadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, benzoimidazolyl, benzooxazolyl, tetrahydrotriazolopyridyl, tetrahydrotriazolopyrimidinyl, benzofuryl, indolyl, isoindolyl, pyri
  • alkylaryl refers to a substituent that is attached via the alkyl group to an aryl, heteroaryl and cycloalkyl group.
  • a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O or S includes aromatic and heteroaromatic rings as well as carbocyclic and heterocyclic rings which may be saturated or unsaturated.
  • Such rings may be, but are not limited to furyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, thiazolyl, thienyl, imidazolyl, imidazolidinyl, imidazolinyl, triazolyl, morpholinyl, piperazinyl, piperidyl, piperidonyl, pyrazolidinyl, pyrazolinyl, pyrrolidinyl, pyrrolinyl, tetrahydropyranyl, thiomorpholinyl, phenyl, cyclohexyl, cyclopentyl and cyclohexenyl.
  • a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O or S includes aromatic and heteroaromatic rings as well as carbocyclic and heterocyclic rings which may be saturated or unsaturated.
  • rings may be, but are not limited to imidazolidinyl, imidazolinyl, morpholinyl, piperazinyl, piperidyl, piperidonyl, pyrazolidinyl, pyrazohnyl, pyrrolidinyl, pyrrolinyl, tetrahydropyranyl or thiomorpholinyl, tetrahydrothiopyranyl, furyl, pyrrolyl, isoxazolyl, isothiazolyl, oxazolyl, oxazolidinonyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, thiazolyl, thienyl, imidazolyl, triazolyl, phenyl, cyclopropyl, aziridinyl, cyclobutyl, azetidinyl, cyclopent
  • a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O or S, which group may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O or S, includes aromatic and heteroaromatic rings as well as carbocyclic and heterocyclic rings which may be saturated or unsaturated.
  • rings may be, but are not limited to naphthyl, norcaryl, chromyl, isochromyl, indanyl, benzoimidazol or tetralinyl, benzooxazolyl, benzothiazolyl, benzofuryl, benzothienyl, benzotriazolyl, indolyl, azaindolyl, indazolyl, indolinyl, isoindolinyl, benzimidazolyl, oxadiazolyl, thiadiazolyl, quinolinyl, quinoxalinyl and benzotriazolyl.
  • a subscript is the integer 0 (zero) the group to which the subscript refers, indicates that the group is absent, i.e. there is a direct bond between the groups.
  • halo may be fluoro, chloro, bromo or iodo.
  • alkylhalo means an alkyl group" as defined above, substituted with one or more halo.
  • d- 6 alkylhalo may include, but is not limited to fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl and bromopropyl.
  • Od- ⁇ alkylhalo may include, but is not limited to fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy and difluoroethoxy.
  • the compounds of formula I useful in accordance with the present invention may also be used as pharmaceutically acceptable salts, but also other salts may be useful in accordance with the present invention.
  • Examples of pharmaceutically acceptable salts useful in accordance with the present invention are, but are not limited to, hydrochloride, 4-aminobenzoate, anthranilate, 4-aminosalicylate, 4- hydroxybenzoate, 3,4-dihydroxybenzoate, 3-hydroxy-2-naphthoate, nitrate and trifluoroacetate.
  • Some compounds of formula I may have chiral centres and/or geometric isomeric centres (E- and Z- isomers), and it is to be understood that the invention encompasses the use of all such optical, diastereoisomers and geometric isomers.
  • the invention also relates to the use of any and all tautomeric forms of the compounds of formula I, la or lb.
  • a further aspect of the invention is the use of a compound formula I, la or lb for the manufacture of a medicament for the prevention of reflux.
  • Still a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment of gastro-esophageal reflux disease (GERD).
  • GFD gastro-esophageal reflux disease
  • a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment of regurgitation.
  • Still a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment or prevention of lung disease.
  • Another aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the management of failure to thrive.
  • Still a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment or prevention of asthma, such as reflux-related asthma.
  • a further aspect of the invention is the use of a compound according to formula I, la or lb for the manufacture of a medicament for the treatment or prevention of functional gastrointestinal disorders, such as functional dyspepsia (FD).
  • FD functional dyspepsia
  • Yet another aspect of the invention is the use of a compound according to formula I, la or lb for the manufacture of a medicament for the treatment or prevention of irritable bowel syndrome (IBS), such as constipation predominant IBS, diarrhea predominant IBS or alternating bowel movement predominant IBS.
  • IBS irritable bowel syndrome
  • Another aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment or prevention of chronic laryngitis.
  • a further aspect of the present invention is a method for the inhibition of transient lower esophageal sphincter relaxations (TLESRs), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such inhibition.
  • TLESRs transient lower esophageal sphincter relaxations
  • Another aspect of the invention is a method for the prevention of reflux, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such prevention.
  • Still a further aspect of the invention is a method for the treatment of gastro-esophageal reflux disease (GERD), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
  • GSD gastro-esophageal reflux disease
  • Yet another aspect of the invention is a method for the treatment of regurgitation, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula
  • Still a further aspect of the invention is a method for the treatment or prevention of asthma, such as reflux-related asthma, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
  • Yet another aspect of the invention is a method for the treatment of chronic laryngitis, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
  • Still a further aspect of the invention is a method for the treatment or inhibition of lung disease, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
  • Still a further aspect of the invention is a method for the management of failure to thrive, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
  • TLESR transient lower esophageal sphincter relaxations
  • GFD gastro-esophageal reflux disease
  • the compounds of formula I, la or lb are in accordance with the present invention suitably formulated into pharmaceutical formulations for oral administration. Also rectal, parenteral or any other route of administration may be contemplated to the skilled man in the art of formulations.
  • the compounds of formula I, la or lb are formulated with at least one pharmaceutically and pharmacologically acceptable carrier or adjuvant.
  • the carrier may be in the form of a solid, semi-solid or liquid diluent.
  • the compound of formula I, la or lb to be formulated is mixed with solid, powdered ingredients such as lactose, saccharose, sorbitol, mannitol, starch, amylopectin, cellulose derivatives, gelatin, or another suitable ingredient, as well as with disintegrating agents and lubricating agents such as magnesium stearate, calcium stearate, sodium stearyl fumarate and polyethylene glycol waxes.
  • disintegrating agents and lubricating agents such as magnesium stearate, calcium stearate, sodium stearyl fumarate and polyethylene glycol waxes.
  • Soft gelatine capsules may be prepared with capsules containing a mixture of the active compound or compounds of the invention, vegetable oil, fat, or other suitable vehicle for soft gelatine capsules.
  • Hard gelatine capsules may contain the active compound in combination with solid powdered ingredients such as lactose, saccharose, sorbitol, mannitol, potato starch, corn starch, amylopectin, cellulose derivatives or gelatine.
  • Dosage units for rectal administration may be prepared (i) in the form of suppositories which contain the active substance(s) mixed with a neutral fat base; (ii) in the form of a gelatine rectal capsule which contains the active substance in a mixture with a vegetable oil, paraffin oil, or other suitable vehicle for gelatine rectal capsules; (iii) in the form of a ready-made micro enema; or (iv) in the form of a dry micro enema formulation to be reconstituted in a suitable solvent just prior to administration.
  • Liquid preparations for oral administration may be prepared in the form of syrups or suspensions, e.g. solutions or suspensions, containing the active compound and the remainder of the formulation consisting of sugar or sugar alcohols, and a mixture of ethanol, water, glycerol, propylene glycol and polyethylene glycol. If desired, such liquid preparations may contain colouring agents, flavouring agents, saccharine and carboxymethyl cellulose or other thickening agent.
  • Liquid preparations for oral administration may also be prepared in the form of a dry powder to be reconstituted with a suitable solvent prior to use.
  • Solutions for parenteral administration may be prepared as a solution of a compound of the invention in a pharmaceutically acceptable solvent. These solutions may also contain stabilizing ingredients and/or buffering ingredients and are dispensed into unit doses in the form of ampoules or vials. Solutions for parenteral administration may also be prepared as a dry preparation to be reconstituted with a suitable solvent extemporaneously before use.
  • the compound of formula I, la or lb may be administered once or twice daily, depending on the severity of the patient's condition.
  • the compounds in accordance with the present invention can be prepared as described in Biological evaluation
  • a multilumen sleeve/sidehole assembly (Dentsleeve, Sydney, South Australia) is introduced through the esophagostomy to measure gastric, lower esophageal sphincter (LES) and esophageal pressures.
  • the assembly is perfused with water using a low-compliance manometric perfusion pump (Dentsleeve, Sydney, South Australia).
  • An air-perfused tube is passed in the oral direction to measure swallows, and an antimony electrode monitored pH, 3 cm above the LES. All signals are amplified and acquired on a personal computer at 10 Hz.
  • placebo (0.9% NaCl) or test compound is administered intravenously (i.v., 0.5 ml/kg) in a foreleg vein.
  • a nutrient meal (10% peptone, 5% D-glucose, 5% Intralipid, pH 3.0) is infused into the stomach through the central lumen of the assembly at 100 ml/min to a final volume of 30 ml/kg.
  • air is insufflated at 40 ml/min.
  • TLESRs is defined as a decrease in lower esophageal sphincter pressure (with reference to intragastric pressure) at a rate of >1 mmHg/s.
  • the relaxation should not be preceded by a pharyngeal signal ⁇ 2s before its onset in which case the relaxation is classified as swallow- induced.
  • the pressure difference between the LES and the stomach should be less than 2 mmHg, and the duration of the complete relaxation longer than 1 s.

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Abstract

The present invention relates to the use of a compound of (formula: Ia); for the inhibition of transient lower esophageal sphincter relaxations. A further aspect of the invention is directed to the use of compounds of formula Ia for the treatment of gastro-esophageal reflux disease.

Description

COMPOUNDS FOR THE TREATMENT OF GASTRO-ESOPHAGEAL REFLUX DISEASE
Field of the invention
The present invention relates to the use of certain compounds for the inhibition of transient lower esophageal sphincter relaxations. A further aspect of the invention is directed to the use of certain compounds for the treatment of gastro-esophageal reflux disease.
Background of the invention
The lower esophageal sphincter (LES) is prone to relaxing intermittently. As a consequence, fluid from the stomach can pass into the esophagus since the mechanical barrier is temporarily lost at such times, an event hereinafter referred to as "reflux".
Gastro-esophageal reflux disease (GERD) is the most prevalent upper gastrointestinal tract disease. Current pharmacotherapy aims at reducing gastric acid secretion, or at neutralizing acid in the esophagus. The major mechanism behind reflux has been considered to depend on a hypotonic lower esophageal sphincter. However, e.g. Holloway & Dent (1990) Gastroenterol. Clin. N. Amer. 19, pp. 517-535, has shown that most reflux episodes occur during transient lower esophageal sphincter relaxations (TLESRs), i.e. relaxations not triggered by swallows. It has also been shown that gastric acid secretion usually is normal in patients with GERD.
The object of the present invention was to find a new way for the inhibition of transient lower esophageal sphincter relaxations (TLESRs), thereby preventing reflux. More particularly the object of the invention was to find a new way of treating gastro-esophageal reflux disease (GERD), as well as a new way for the treatment of regurgitation.
Outline of the invention
The present invention is directed to the use of compounds of formula la
Figure imgf000003_0001
wherein: P is selected from the group consisting of hydrogen, C3.7alkyl or a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S;
R1 is selected from the group consisting of hydrogen, hydroxy, halo, nitro, C^alkylhalo, O . 6alkylhalo, C^alkyl, OC^alkyl, C2.6alkenyl, OC2.6alkenyl, C2.6alkynyl, OC2.6alkynyl, C0.
6alkylC3.6cycloalkyl, OC0.6alkylC3.6cycloalkyl, C0.6alkylaryl, OC0.6alkylaryl, CHO, (CO)R5,
O(CO)R5, O(CO)OR5, O(CN)OR5, C^alkylOR5, OC2.6alkylOR5, C1.6alkyl(CO)R5, OCi.
6alkyl(CO)R5, C0.6alkylCO2R5, OC^alkylCO^5, C0.6alkylcyano, OC2.6alkylcyano, C0.
6alkylNR5R6, OC2.6alkylNR5R6, C1.6alkyl(CO)NR5R6, Od-ealkylCCO^ , C0. 6alkylNR5(CO)R6, OC2.6alkylNR5(CO)R6, Co.6alkylNR5(CO)NR5R6, C0.6alkylSR5, OC2.6alkylSR5
C0.6alkyl(SO)R5, OC2.6alkyl(SO)R5, C0.6alkylSO2R5, OC2.6alkylSO2R5, C0.6alkyl(SO2)ι R5R6,
OC2.6alkyl(SO2)r^ A-6alkylNR5(SO2)R^ OC2_6al^^
OC2.6alkylNR5(SO2)NR5R6, (CO)NR5R6, O(CO)NR5R6, NR5OR6, C0.6alkylNR5(CO)OR6, OC2.
6alkylNR5(CO)OR6, SO3R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S, wherein said ring may be substituted by one or more A;
M1 is selected from the group consisting of a bond, C^alkyl, C2.3alkenyl, C2.3alkynyl, C0.
4alkyl(CO)C0.4alkyl, C0.3alkylOC0.3alkyl, C0.3alkyl(CO) R5, C0.3alkyl(CO)NR5Co-3alkyl, C0.
4alkylNR5, C0.3alkylSC0.3alkyl, C0-3alkyl(SO)C0'.3alkyl or C0.3alkyl(SO2)C0.3alkyl; R2 is selected from the group consisting of hydrogen, hydroxy, Co-6alkylcyano, oxo, = R5,
=NOR5, C^alkylhalo, halo, d^alkyl, O(CO)C1.4alkyl, C1.4alkyl(SO)C0.4alkyl, Ct. 4alkyl(SO2)C0.4alkyl, (SO)C0.4alkyl, (SO2)C0.4alkyl, OCMalkyl, d_4alkylOR5 and C0.
4alkylNR5R6;
X1, X2 and X3 are independently selected from the group consisting of CR, CO, N, NR, O and S;
R is selected from the group consisting of hydrogen, Co-3alkyl, halo, Co.3alkylOR5, C0. 3alkyl R5R6, C0.3alkyl(CO)OR5, C0-3alkylNR5R6 and C0.3alkylaryl;
M2 is selected from a group consisting of a bond, d^alkyl, C3. cycloalkyl, C .3alkenyl, C2.
3alkynyl, C0.4alkyl(CO)C0.4alkyl, Co.3alkylOCo.3alkyl, Co-salkylNR^walkyl, C0.3alkyl(CO)NR5,
C0.4alkyl R5, C0.3alkylSCo.3alkyl, Co.3alkyl(SO)Co-3alkyl and C0-3alkyl(SO2)Co-3alkyl;
R3 is selected from a group consisting of hydrogen, hydroxy, Co.6alkylcyano, oxo, = R5, =NOR5, d.4alkylhalo, halo, C alkyl, O(CO)Ci.4alkyl, d.4alkyl(SO)C0. alkyl, d.
4alkyl(SO2)C0.4alkyl, (SO)C0.4alkyl, (SO2)C0.4alkyl, Od.4alkyl, d-4alkylOR5 and C0-
4alkylNR5R6;
X4 is selected from the group consisting of C0.4alkylR5, C0.4alkyl(NR5R6), C0. alkyl(NR5R6)=N, R5C0.4alkyl(NR5R6)=N, NOC0.4alkyl, C1.4alkylhalo, C, O, SO, SO2 and S; Q is a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S, which group may optionally be fused with a 5- or 6- membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S and which fused ring may be substituted by one or more A;
R4 is selected from the group consisting of hydrogen, hydroxy, Co-6alkylcyano, oxo, =NR5, =NOR5, C1.4alkylhalo, halo, C alkyl, Od.4alkyl, OC0.6alkylaryl, O(CO)C1.4alkyl, C0.
4alkyl(S)C0-4alkyl, d.4alkyl(SO)C0.4alkyl, d.4alkyl(SO2)Co.4alkyl, (SO)C0.4alkyl, (SO2)C0.
4alkyl, d-4alkylOR5, C0.4alkylNR5R6 and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O or S, wherein said ring may be substituted by one or more
A; R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, d-6alkyl,
Co-6alkylC3-6cycloalkyl, Co-6alkylaryl, C0.6alkylheteroaryl and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O and S, and wherein R5 and
R6 may together form a 5- or 6-membered ring containing one or more atoms independently selected from the goup consisting of C, N, O and S; wherein any d-6alkyl, C2.6alkenyl, C2.6alkynyl, Co-6alkylC3.6cycloalkyl, C0.6alkylaryl and C0.
6alkylheteroaryl defined under R1, R2, R3, R4, R5 and R6 may be substituted by one or more A;
A is selected from the group consisting of hydrogen, hydroxy, oxo, halo, nitro, Co-6alkylcyano, d.4alkyl, Co- alkylC3.6cycloalkyl, d-βalkylhalo, Od-βalkylhalo, C2.6alkenyl, Od_6alkyl, C0.
3alkylaryl, C0.6alkylOR5, OC2.6alkylOR5, Cι.6alkylSR5, OC2.6alkylSR5, (CO)R5, O(CO)R5, OC2. 6alkylcyano, C0.6alkylCO2R5, Od-6alkylCO2R5, O(CO)OR5, OC1.6alkyl(CO)R5, d. 6alkyl(CO)R5, NR5OR6, C0-6alkyll R5R6, OC2.6alkylNR5R6, C0.6alkyl(CO)NR5R6, Od.
6alkyl(CO) R5R6, OC2.6alkylNR5(CO)R6, C0.6alkyl R (CO)R6,
C0.6alkylNR5(CO)NR5R6, O(CO) R5R6, NR5(CO)OR6, C0.6alkyl(SO2)NR5R6,
OC2.6alkyl(SO2)NR5R6, C0.6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, SO3R5, d.6alkylNR5(SO2)NR5R6, OC2.6alkyl(SO2)R5, Co.6alkyl(SO2)R5, Co.6alkyl(SO)R5,
OC2.6alkyl(SO)R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; m is selected from 0, 1, 2, 3 and 4; and n is selected from 0, 1, 2 and 3, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the inhibition of transient lower esophageal sphincter relaxations (TLESRs).
The present invention further provides the use of a compound of formula I
Figure imgf000005_0001
(I) wherein:
P is selected from the group consisting of thiophene, pyridyl, thiazolyl, furyl, pyrrolyl and phenyl, whereby the phenyl ring is substituted on position 3 or disubstituted on positions 2 and 5; R1 is attached to P via a carbon atom on ring P and is selected from the group consisting of hydrogen, hydroxy, halo, nitro, Cι.6alkylhalo, Od.6alkylhalo, d.6alkyl, Od.6alkyl, C2.6alkenyl, OC2.6alkenyl, C2.6alkynyl, OC2.6alkynyl, Co-6alkylC3.6cycloalkyl, OCo-6alkylC .6cycloalkyl, C0. ealkylaryl, OC0.6alkylaryl, CHO, (CO)R5, O(CO)R5, O(CO)OR5, O(CN)OR5, d.6alkylOR5, OC2.
6alkylORD, d.6alkyl(CO)RD, OC1.6alkyl(CO)RD, C0.6alkylCO2RD, Od.6alkylCO2R3, C0. ealkylcyano, OC2.6alkylcyano, C0.6alkyl R5R6, OC2.6alkylNR5R6, d.6alkyl(CO)NR5R6, OCi. 6alkyl(CO)NR5R6, C0.6alkyl R5(CO)R6, OC2.6alkylNR5(CO)R6, C0.6alkylNR5(CO)NR5R6, C0. 6alkylSR5, OC2.6alkylSR5, C0.6alkyl(SO)R5, OC2.6alkyl(SO)R5, C0-6alkylSO R5, OC2.6alkylSO2R5, C0.6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6,Co.6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, C0. 6alkylNR5(SO2)NR5R6, OC2.6alkylNR5(SO2)NR5R6, (CO)NR5R6, O(CO)NR5R6, NR5OR6, C0. 6alkylNR5(CO)OR6, OC2.6alkylNR5(CO)OR6, SO3R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S;
M1 is a bond;
X1 selected from the group consisting of C, CO, N, O and S;
X2 is selected from the group consisting of C, N, O and S; X3 is i) selected from the group consisting of N, O and S, or ii) selected from N, O, S, and C when X2 is selected from N, O, or S, and when X3 is C the substituent R on X3 is H. ;
R is selected from the group consisting of hydrogen, C0-3 alkyl, halo, C0-3alkylOR5, C0.
3alkylNR5R6, C0-3alkyl(CO)OR5 and C0.3alkylaryl; M2 is selected from a group consisting of a bond, d-3alkyl, C2.3alkynyl, C0-4alkyl(CO)Co-4alkyl,
C~3_3alkylOC0.3aU.yl, Co-salky E^d-salkyl, C0.3alkyl(CO)NR5, C0.4alkylNR5, C0-3alkyl(SO)C0-
3alkyl and Co-3alkyl(SO2)C0.3alkyl;
R3 is selected from a group consisting of hydroxy, Co-6alkylcyano, oxo, =NR5, =NOR5, d_
4alkylhalo, halo, CMalkyl, O(CO)d.4alkyl, d.4alkyl(SO)C0.4alkyl, d.4alkyl(SO2)C0. alkyl, (SO)C0.4alkyl, (SO2)C0-4alkyl, OCMalkyl, C alkylOR5 and C0.4alkylNR5R6;
X4 is selected from the group consisting of Co-4alkylR5R6 , C3_7cycloalkyl, C1.4alkyl(NR5R6),
NR5, C0-4alkyl(NR5R6)=N, NR5C«Malkyl(NR5R6)=N, NOC0.4alkyl, d.4alkylhalo, O, SO, SO2 and S, and wherein the bond between M2 and X4 is a single bond ;
Q is i) selected from the group consisting of triazolyl, imidazolyl, oxadiazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, and wherein any substitutable nitrogen atom in the ring is substituted with R4 on such nitrogen atom and any suitable carbon atom is optionally substituted with R4; and
R4 is selected from the group consisting of Co-6alkylcyano, =NCι. alkyl, =NOR5, d. 4alkylhalo, halo, Ci-βalkyl, OC1.4alkyl, C2.4alkenyl, Co-2alkylC3.6cycloalkyl, C0.6alkylaryl, Co- 6alkylheteroaryl, OCo-6alkylaryl, OCo-6alkylheteroaryl, NCo-6alkylaryl, NCo-
6alkylheteroaryl,Co-6alkylOaryl, Co-6alkylOheteroaryl, Co-6alkylNaryl, Co-6alkylNheteroaryl, OC0.6alkylOaryl, OC0.6alkylOheteroaryl, OC0.6alkylNaryl, OC0.6alkylNheteroaryl, NC0. 6alkylOaryl, NC0.6alkylOheteroaryl, NC0-6alkylNaryl, NC0.6alkylNheteroaryl, O(CO)Cι. 4alkyl, C0. alkyl(CO)Od.4alkyl5 d.4alkyl(S)C0.4alkyl, C alkyl(SO)C0.4alkyl, d. 4alkyl(SO2)C0.4alkyl, (SO)C0.4alkyl, (SO2)C0.4alkyl, d.4alkylOR5, C0^alkylN(d.4alkyl)2 and a 3- or 6-membered non-aromatic ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A; or ii) selected from the group consisting of benzoimidazolyl. benzooxazolyl, tetrahydrotriazolopyridyl, tetrahydrotriazolopyrimidinyl, pyridonyl, pyridazinyl, imidazopyridyl, oxazolopyridyl, thiazolopyridyl, imidazopyridazinyl, oxazolopyridazinyl, thiazolopyridazinyl and purinyl; and
R4 is selected from the group consisting of hydrogen, hydroxy, Co-6alkylcyano, =NR5, =NOR5, d.4alkylhalo, halo, d-ealkyl, Od.4alkyl, OC0.6alkylaryl, O(CO)d-4alkyl, C0.
4alkyl(S)C0.4alkyl, d. alkyl(SO)C0.4alkyl, d.4alkyl(SO2)C0.4alkyl, (SO)C0-4alkyl, (SO2)C0- 4alkyl, d-4alkylOR5, Co-4alkylNR5R6 and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A;
R5 and R6 are independently selected from the group consisting of hydrogen and d.6alkyl; wherein any d-6alkyl defined under R1, R2 and R4 may be substituted by one or more A ;
A is selected from the group consisting of hydrogen, hydroxy, halo, nitro, oxo, C0.6alkylcyano, Co.4alkylC3.6cycloalkyl, Cι_6alkyl, d.6alkylhalo, Od.6alkylhalo, C2.6alkenyl, C0-3 alkylaryl, Co-
6alkylOR5, OC2.6alkylOR5, Cι.6alkylSR5, OC2.6alkylSR5, (CO)R5, O(CO)R5, OC2.6alkylcyano,
Od_6alkylCO2R5, O(CO)OR5, Od.6alkyl(CO)R5, d.6alkyl(CO)R5, NR5OR6, OC2.6alkylNR5R6,
C0-6alkyl(CO) R5R6, Od.6alkyl(CO)NR5R6, OC2.6alkylNR5(CO)R6, C0.6alkylNR5(CO)R6, C0.
6alkylNR5(CO)NR5R6, O(CO)NR5R6, C0.6alkyl(SO2) R5R6, OC2.6alkyl(SO2)NR5R6, C0. 6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, SO3R5, d.6alkylNR5(SO2)NR5R6, OC2.
6alkyl(SO2)R5, C0.6alkyl(SO2)R5, C0-6alkyl(SO)R5,
OC2.6alkyl(SO)R5 and a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; ml is selected from 0, 1, 2, 3 and 4; m2 is selected from 0, 1 , 2 and 3; n is selected from 0, 1 and 2; and t is O or 1, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the inhibition of transient lower esophageal sphincter relaxations (TLESRs).
The present invention further provides the use of a compound of formula lb
Figure imgf000008_0001
(lb) wherein:
P is selected from the group consisting of thiophene, pyridyl, thiazolyl, furyl, pyrrolyl and phenyl, whereby the phenyl ring is substituted on position 3 or disubstituted on positions 2 and 5;
R1 is attached to P via a carbon atom on ring P and is selected from the group consisting of hydrogen, hydroxy, halo, nitro, d.6alkylhalo, Od-δalkylhalo, d.6alkyl, Od-βalkyl, C2-6alkenyl,
OC2.6alkenyl, C2.6alkynyl, OC2-6alkynyl, Co.6alkylC3.6cycloalkyl, OCo-6alkylC3.6cycloalkyl, C0. galkylaryl, OC0.6alkylaryl, CHO, (CO)R5, O(CO)R5, O(CO)OR5, O(CN)OR5, C^galkylOR5, OC2. 6alkylOR5, d.6alkyl(CO)R5, Od.6alkyl(CO)R5, C0.6alkylCO2R5, Od.6alkylCO2R5, C0.
6alkylcyano, OC2.6alkylcyano, C0.6alkylNR5R6, OC2.6alkylNR5R6, d.6alkyl(CO)NR5R6, Od-
6alkyl(CO)NR5R6, Co-6alkylNR5(CO)R6, OC2.6alkylNR5(CO)R6, C0.6alkylNR5(CO) R5R6, C0.
6alkylSR5, OC2.6alkylSR5, C0.6alkyl(SO)R5, OC2.6alkyl(SO)R5, C0-6alkylSO2R5, OC2.6alkylSO2R5,
C0.6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6,C0.6alkyl R5(SO2)R6, OC2.6alkylNR5(SO2)R6, Co- 6alkylNR5(SO2)NR5R6, OC2.6alkylNR5(SO2)NR5R6, (CO)NR5R6, O(CO) R5R6, NR5OR6, C0.
6alkyl R5(CO)OR6, OC2.6alkylNR5(CO)OR6, SO3R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S;
M1 is a bond;
X1 selected from the group consisting of C, CO, N, O and S; X2 is selected from the group consisting of C, N, O and S;
X3 is selected from the group consisting of N, O and S, or X3 is CH when X2 is N, O or S;
R is selected from the group consisting of hydrogen, Co-3alkyl, halo, Co-3alkylOR5, Co-
3alkylNR5R6, C0-3alkyl(CO)OR5 and Co.3alkylaryl;
M2 is selected from a group consisting of a bond, CMalkyl, C2.3alkynyl, Co-4alkyl(CO)C0-4alkyl, C0-3alkylOCo-3alkyl, Co-3alkylNR5d.3alkyl, C0.3alkyl(CO)NR5, C0.4alkylNR5, Co-3alkyl(SO)C0.
3alkyl and Co-3alkyl(SO2)Co-3alkyl;
R3 is selected from a group consisting of hydroxy, C0.6alkylcyano, oxo, =NR5, =NOR5, d-
4alkylhalo, halo, C alkyl, O(CO)d.4alkyl, d-4alkyl(SO)C0.4alkyl, C1.4alkyl(SO2)C0.4alkyl,
(SO)C0.4alkyl, (SO2)C0.4alkyl, Od.4alkyl, d.4alkylOR5 and C0.4alkylNR5R6; X4 is selected from the group consisting of Co- alkylR5R6 , C3.7cycloalkyl, C1.4alkyl(NR5R6),
1 R5, C0-4alkyl(NR5R6)=N, NR5C0.4alkyl(NR5R6)=N, NOC0. alkyl, d.4alkylhalo, O, SO, SO2 and S, and wherein the bond between M2 and X4 is a single bond ;
Q is i) selected from the group consisting of triazolyl, imidazolyl, oxadiazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, and wherein any substitutable nitrogen atom in the ring is substituted with R4 on such nitrogen atom; and
R4 is selected from the group consisting of C0.6alkylcyano, =NC1.4alkyl, =NOR5, d- 4alkylhalo, halo, d_6alkyl, Od.4alkyl, C2- alkenyl, C0.2alkylC3.6cycloalkyl, Co-6alkylaryl, C0. 6alkylheteroaryl, OCo-6alkylaryl, OC0.6alkylheteroaryl, NC0.6alkylaryl, NC0. 6alkylheteroaryl,C0.6alkylOaryl, C0.6alkylOheteroaryl, C0.6alkylNaryl, C0.6alkylNheteroaryl,
OC0.6alkylOaryl, OC0.6alkylOheteroaryl, OC0.6alkylNaryl, OC0.6alkylNheteroaryl, NC0. 6alkylOaryl, NC0.6alkylOheteroaryl, NC0.6alkylNaryl, NC0.6alkylNheteroaryl, O(CO)d. 4alkyl, C0.4alkyl(CO)Od.4alkyl, d.4alkyl(S)C0.4alkyl, d.4alkyl(SO)C0.4alkyl, d. 4alkyl(SO2)C0.4alkyl, (SO)C0. alkyl, (SO2)C0.4alkyl, d.4alkylOR5, C0-4alkylN(C1.4alkyl)2 and a 3- or 6-membered non-aromatic ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A; or ii) selected from the group consisting of benzoimidazolyl, benzooxazolyl, tetrahydrotriazolopyridyl, tetrahydrotriazolopyrimidmyl, pyridonyl, pyridazinyl, imidazopyridyl, oxazolopyridyl, thiazolopyridyl, imidazopyridazinyl, oxazolopyridazinyl, thiazolopyridazinyl and purinyl; and
R4 is selected from the group consisting of hydrogen, hydroxy, C0.6alkylcyano, =NR5, =NOR5, CMalkylhalo, halo, d.6alkyl, Od.4alkyl, OC0.6alkylaryl, O(CO)C1.4alkyl, C0. 4alkyl(S)C0- alkyl, d-4alkyl(SO)C0- alkyl, C1.4alkyl(SO2)C0.4alkyl, (SO)C0.4alkyl, (SO2)C0.
4alkyl, C!. alkylOR5, Co-4alkylNR5R6 and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A;
R5 and R6 are independently selected from the group consisting of hydrogen and d-6alkyl; wherein any d.6alkyl defined under R1, R2 and R4 may be substituted by one or more A ;
A is selected from the group consisting of hydrogen, hydroxy, halo, nitro, oxo, Co-6alkylcyano,
Co-4alkylC3-6cycloalkyl, d.6alkyl, d-βalkylhalo, Od.6alkylhalo, C2-6alkenyl, C0.3 alkylaryl, Co- 6alkylOR5, OC2-6alkylOR5, d.6alkylSR5, OC2.6alkylSR5, (CO)R5, O(CO)R5, OC2.6alkylcyano, Od.6alkylCO2R5, O(CO)OR5, Od.6alkyl(CO)R5, d.6alkyl(CO)R5, 1 R50R6, OC2.6alkyl R5R6, C0-6alkyl(CO) R5R6, Od.6alkyl(CO)NR5R6, OC2.6alkylNR5(CO)R6, C0.6alkylNR5(CO)R6, C0- 6alkylNR5(CO)NR5R6, O(CO)NR5R6, C0.6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6, C0. 6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, SO3R5, d.6alkylNR5(SO2)NR5R6, OC2. 6alkyl(SO2)R5, C0.6alkyl(SO2)R5, C0.6alkyl(SO)R5,
OC2.6alkyl(SO)R5 and a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; ml is selected from 0, 1, 2, 3 and 4; m2 is selected from 0, 1, 2 and 3; n is selected from 0, 1 and 2; and t is O or 1, or pharmaceutically acceptable salt or an optical isomer thereof; for the manufacture of a medicament for the inhibition of transient lower esophageal sphincter relaxations (TLESRs).
Listed below are definitions of various terms used in the specification and claims to describe the present invention.
For the avoidance of doubt it is to be understood that in this specification 'd-δ' means a carbon group having 1, 2, 3, 4, 5 or 6 carbon atoms. In this specification "C" means 1 carbon atom.
In this specification, unless stated otherwise, the term "alkyl" includes both straight and branched chain alkyl groups and may be methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, t-pentyl, neo-pentyl, n-hexyl or i-hexyl, t-hexyl. The term "Ci- 3alkyl" refers to an alkyl group having 1, 2 or 3 carbon atoms, and may be methyl, ethyl, n- propyl and i-propyl.
In this specification, unless stated otherwise, the term "cycloalkyl" refers to an optionally substituted, saturated cyclic hydrocarbon ring system. The term "C3.7cycloalkyl" may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
In this specification, unless stated otherwise, the term "alkenyl" includes both straight and branched chain alkenyl groups. The term "C2-6alkenyl" refers to an alkenyl group having 2 to 6 carbon atoms and one or two double bonds, and may be, but is not limited to vinyl, allyl, propenyl, i-propenyl, butenyl, i-butenyl, crotyl, pentenyl, i-pentenyl and hexenyl.
In this specification, unless stated otherwise, the term "alkynyl" includes both straight and branched chain alkynyl groups. The term C2-6alkynyl having 2 to 6 carbon atoms and one or two triple bonds, and may be, but is not limited to ethynyl, propargyl, butynyl, i-butynyl, pentynyl, i- pentynyl and hexynyl.
The term "aryl" refers to an optionally substituted monocyclic or bicyclic hydrocarbon ring system containing at least one unsaturated aromatic ring. Examples and suitable values of the term "aryl" are phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, indyl and indenyl.
In this specification, unless stated otherwise, the term "heteroaryl" refer to an optionally substituted monocyclic or bicyclic unsaturated, aromatic ring system containing at least one heteroatom selected independently from N, O or S. Examples of "heteroaryl" may be, but are not limited to thiophene, thienyl, pyridyl, thiazolyl, furyl, pyrrolyl, triazolyl, imidazolyl, oxadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, benzoimidazolyl, benzooxazolyl, tetrahydrotriazolopyridyl, tetrahydrotriazolopyrimidinyl, benzofuryl, indolyl, isoindolyl, pyridonyl, pyridazinyl, pyrimidinyl, imidazopyridyl, oxazolopyridyl, thiazolopyridyl, pyridyl, imidazopyridazinyl, oxazolopyridazinyl, thiazolopyridazinyl and purinyl.
In this specification, unless stated otherwise, the term "alkylaryl", "alkylheteroaryl " and "alkylcycloalkyl " refer to a substituent that is attached via the alkyl group to an aryl, heteroaryl and cycloalkyl group.
In this specification, unless stated otherwise, a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O or S, includes aromatic and heteroaromatic rings as well as carbocyclic and heterocyclic rings which may be saturated or unsaturated. Examples of such rings may be, but are not limited to furyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, thiazolyl, thienyl, imidazolyl, imidazolidinyl, imidazolinyl, triazolyl, morpholinyl, piperazinyl, piperidyl, piperidonyl, pyrazolidinyl, pyrazolinyl, pyrrolidinyl, pyrrolinyl, tetrahydropyranyl, thiomorpholinyl, phenyl, cyclohexyl, cyclopentyl and cyclohexenyl. In this specification, unless stated otherwise, a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O or S, includes aromatic and heteroaromatic rings as well as carbocyclic and heterocyclic rings which may be saturated or unsaturated. Examples of such rings may be, but are not limited to imidazolidinyl, imidazolinyl, morpholinyl, piperazinyl, piperidyl, piperidonyl, pyrazolidinyl, pyrazohnyl, pyrrolidinyl, pyrrolinyl, tetrahydropyranyl or thiomorpholinyl, tetrahydrothiopyranyl, furyl, pyrrolyl, isoxazolyl, isothiazolyl, oxazolyl, oxazolidinonyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidyl, pyrrolyl, thiazolyl, thienyl, imidazolyl, triazolyl, phenyl, cyclopropyl, aziridinyl, cyclobutyl, azetidinyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl and cyclooctenyl.
In this specification, unless stated otherwise, a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O or S, which group may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O or S, includes aromatic and heteroaromatic rings as well as carbocyclic and heterocyclic rings which may be saturated or unsaturated. Examples of such rings may be, but are not limited to naphthyl, norcaryl, chromyl, isochromyl, indanyl, benzoimidazol or tetralinyl, benzooxazolyl, benzothiazolyl, benzofuryl, benzothienyl, benzotriazolyl, indolyl, azaindolyl, indazolyl, indolinyl, isoindolinyl, benzimidazolyl, oxadiazolyl, thiadiazolyl, quinolinyl, quinoxalinyl and benzotriazolyl.
In this specification, unless stated otherwise, the term "=NR5" and "=NOR5" include imino- and oximogroups carrying an R5 substituent and may be, or be part of, groups including, but not limited to iminoalkyl, iminohydroxy, iminoalkoxy, amidine, hydroxyamidine and alkoxy amidine.
In the case where a subscript is the integer 0 (zero) the group to which the subscript refers, indicates that the group is absent, i.e. there is a direct bond between the groups.
In this specification, unless stated otherwise, the term "bond" is a saturated bond.
In this specification, unless stated otherwise, the term "halo" may be fluoro, chloro, bromo or iodo.
In this specification, unless stated otherwise, the term "alkylhalo" means an alkyl group" as defined above, substituted with one or more halo. The term "d-6alkylhalo" may include, but is not limited to fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl and bromopropyl. The term "Od-βalkylhalo" may include, but is not limited to fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy and difluoroethoxy.
Specific examples of compounds useful according to the present invention include
2-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-lH-benzoimidazole,
5-(3-Methoxy-phenyl)-3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole, 3-[5-(l-Methyl-5-thiophen-2-yl-lH-imidazol-2-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- benzonitrile,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]traiazol-3-ylsulfanylmethyl)-5-phenyl-[l,2,4]oxadiazole,
2- [5 -(3 -Methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5 -methyl- 1 H-benzoimidazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, 3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-trifluoromethyl- phenyl)-[l ,2,4]oxadiazole,
3-(3-Methoxy-phenyl)-5-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-phenyl-[l,2,4]oxadiazole, 5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-m-tolyl-[l,2,4]oxadiazole,
3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile, 3-[4-Methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[l,2,4]oxadiazole, 3-[5-(2-Methyl-thiazol-4-yl)-[l,3,4]oxadiazol-2-ylsulfanylmethyl]-5-m-tolyl-[l,2,4]oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[l,2,4]oxadiazole,
3-[5-(2,4-Dimethyl-thiazol-5-yl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[l,2,4]oxadiazole, 3-[4-Me yl-5-(5-nifro-furan-2-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[l,2,4]oxadiazole,
4-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
3-[5-(4-tert-Butyl-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-[l,2,4]- oxadiazole, 2-Chloro-5-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
2-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-benzooxazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[l,2,4]oxadiazole, 3-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
5-(3-Fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
2-(5-m-Tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-pyridine,
2- [5 -(3 -Methoxy-phenyl)- [ 1,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-imidazo [4, 5-b]pyridine, 5-(3-Fluoro-5-methyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4]oxadiazole,
3-Methyl-5-[3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine,
3-(4-Methyl-5-phenyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, 2-[4-Me l-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
4-Benzyl-2-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- morpholine,
4-[4-Methyl-5-(5-thiophen-3-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiazol-4-yl-
[l,2,4]oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-nitro-phenyl)-
[l,2,4]oxadiazole,
2-Methyl-4-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4]oxadiazol-5-yl]-pyridine,
3-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
3-(4-Methyl-5-thiophene-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[l,2,4]oxadiazole,
3-(4-Methyl-5-thiazol-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, 5-(3-Iodo-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(3-Ethyl-ρhenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
2- [5 -(2-Methyl-pyridin-4-yl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole, 2-[5-(3-Iodo-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-lH-benzoimidazole, 3-(4-Methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[l,2,4]oxadiazole,
2,6-Dichloro-4-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3- yl] -pyridine, 3-(4-Methyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
Dimethyl-{3-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]phenyl}-amine,
5-(3-Chloro-phenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-trifluoromethoxy- phenyl) [1,2,4] oxadiazole,
3-(5-Cyclohexyl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
3-(5-tert-Butyl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
5 -(3 -Bromo-phenyl)-3 -(4-methyl-5 -thiophen-2-yl-4H- [ 1 ,2,4] triazol-3 -ylsulfanylmethyl)- [l,2,4]oxadiazole,
2- [5 -(3 -Bromo-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole,
5-(3-Methoxymethyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-lsulfanylmethyl)-
[l,2,4]oxadiazole,
2- [5 -(3 -Methoxymethyl-phenyl)- [ 1,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole, 4-[5-(4-Methyl-5-thiophen-2-yl-4Η-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- pyridine,
2-{l-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-l-methyl-lH-imidazo[4,5- b]pyridine,
2- [5 -(3 -Methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 -methyl- 1 H-imidazo [4, 5 -b] , 3-[l-Methyl-l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-5-m-tolyl-
[l,2,4]oxadiazole,
3.[l.(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-5-m-tolyl-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfonylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfinylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, or
5-(3-Furan-3-yl-phenyl)-3-(4-memyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-(4-Cyclopropyl-5-{l-[5-(2,5-difluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4Η- [l,2,4]triazol-3-yl)-pyridine, 4-(5-{l-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-{4-Methyl-5-[l-(5-m-tolyl-[l,2,4]oxadiazol-3-yl)-ethylsulfanyl]-4H-[l,2,4]triazol-3-yl}- pyridine, 5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-o-tolyl-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-cyclopropyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
2- { 3 - [5 -(2-Fluoro-5 -methyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5-thiophen-2-yl-
[l,2,4]triazol-4-yl}-ethanol, 4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[l,2,4]triazol-3-yl}-pyrimidine,
3-(4-Ethyl-5-furan-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl-phenyl)-
[1,2,4] oxadiazole,
{ 3 - [5 -(2-Fluoro-5 -methyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5 -thiophen-2-yl- [1 ,2,4]triazol-4-yl} -acetic acid methyl ester,
5-(2-Fluoro-5-methyl-phenyl)-3-[5-furan-2-yl-4-(2-methoxy-ethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
3-(4-Cyclopropyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l ,2,4] oxadiazole, 3-(5-Chloro-2-fluoro-phenyl)-5-(4-cyclopropylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-{5-[3-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyrimidine,
3-(5-Cyclopentyl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, 3-(3-Chloro-phenyl)-5-{4-ethyl-5-[2-(4-methoxy-phenyl)-ethyl]-4H-[l,2,4]triazol-3- ylsulfanylmethyl}-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-p-tolyloxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(2-methoxy-ethyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l ,2,4] oxadiazole,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-ρhenyl)-3-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-(5-{l-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
3-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
3-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-[l,2,4]oxadiazole,
5-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-furan-2-yl-[l,2,4]oxadiazole, 5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- methanol,
3-(3-Chloro-ρhenyl)-5-[4-ethyl-5-(2-methoxy-ethyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,2,4]oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-methylsulfanylmethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole, 3-(3-Chloro-phenyl)-5-(5-ethoxymethyl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazole-3- carboxylic acid methyl ester,
2-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,3,4]oxadiazole,
2-(3-Chloro-phenyl)-5-(4-cyclopropyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,3,4]oxadiazole,
5-(3-Chloro-phenyl)-3- { 1 -[4-ethyl-5-(tetrahydro-furan-2-yl)-4H-[ 1 ,2,4]triazol-3-ylsulfanyl] - ethyl}-[l ,2,4]oxadiazole, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridazine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- ylmethyl)-pyridine,
5-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridin-2-ol, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-phenol,
5-(3-Chloro-phenyl)-3-[5-(4-methoxy-phenoxymethyl)-4-(tetrahydro-furan-2-ylmethyl)-4H-
[ 1 ,2,4]triazol-3 -ylsulfany lmethyl] -[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-[4-cyclopropyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, 3-[4-Ethyl-5-(tetrahydro-furan-2-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[1,2,4] oxadiazole,
2-(3-Chloro-phenyl)-5-{l-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-
[l,3,4]oxadiazole,
4-{5-[3-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3- yl}-pyrimidine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyrimidine,
3-(3-Chloro-phenyl)-5-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5-(3-Methylsulfanyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
2- [5-(3 -Methylsulfanyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole,
5-(2,5-Dimethyl-ρhenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5-(2-Fluoro-5-methyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(3-Cyclopropyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-{5-[2-(3-Chloro-phenyl)-oxazol-4-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3-yl}- pyridine,
4-[4-Methyl-5-(5-thiophen-2-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-{4-Methyl-5-[5-(3-methylsulfanyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
2-Methyl-4-[3-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl]-pyridine,
1 - {3-[3-(4-Methyl-5-thiophen-2-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-[ 1 ,2,4] oxadiazol-5-yl]- phenyl }-ethanone,
4-{5-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
2-Methyl-4-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3- yl]-pyridine, 3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-5-thiophen-2-yl-4H-
[l,2,4]triazole,
4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3-yl}- pyridine,
3-(4-Butyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)- [1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[4-(3-methoxy-proρyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
3-(4-Benzyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-(4-furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
3-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(3-Chloro-ρhenyl)-3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl } -2-methyl-pyridine,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
3-{5-[5-(2-Fluoro-5-methyl-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
5-(3-Chloro-phenyl)-3-(5-thiophen-2-yl-4-thiophen-2-ylmethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l ,2,4] oxadiazole, 5-(3-Cl loro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-{5-[3-(2-Fluoro-5-methyl-ρhenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 4- { 5- [3 -(2-Fluoro-5-methyl-phenyl)- [ 1 ,2,4] oxadiazol-5 -ylmethylsulfanyl] -4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4- { 5 - [5-(5-Bromo-2-fluoro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
3 - { 5 - [5 -(5-Bromo-2-fluoro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H- [l,2,4]triazol-3-yl}-pyridine,
5-(5-Bromo-2-fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-phenyl-[l,2,4]oxadiazole,
3-{5-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl}-pyridine,
4-{5-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(3-Fluoro-phenyl)-3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 3-[4-Methyl-5-(5-thiophen-3-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole,
2-Chloro-4-[3-(4-methyl-5-pyridin-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol- 5-yl] -pyridine,
2-Chloro-4-[3-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl]-pyridine,
2-Chloro-4-[3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine, 4-[4-Methyl-5-(5-phenyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-phenyl-[l,2,4]oxadiazole,
5-(5-Bromo-2-fluoro-ρhenyl)-3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l ,2,4] oxadiazole,
3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazole, 2-Chloro-4-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [ 1 ,2,4] oxadiazol-5-yl] -pyridine,
4- { 5-[3-(3-Fluoro-phenyl)- [ 1 ,2,4] oxadiazol-5-ylmethylsulfanyl] -4-methyl-4H- [ 1 ,2,4]triazol-3 - yl} -pyridine,
3-(3-Fluoro-phenyl)-5-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl-phenyl)-
[1,2,4] oxadiazole,
4- { 5- [5 -(3 -Chloro-phenyl)- [ 1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-furan-2-ylmethyl-4H- [l,2,4]triazol-3-yl}-pyridine,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
3-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine, 5-(3-Chloro-phenyl)-3-(4-ethyl-5-thiophen-3-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
3 - { 5- [5 -(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-furan-2-ylmethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
3-(4-Furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- [1,2,4] oxadiazole,
5-(5-Fluoro-2-methyl-phenyl)-3-(4-furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-furan-2-ylmethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 3-[3-(4-Methyl-5-pyridin-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
3-[3-(4-Methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
3-[3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
2-Chloro-4-[3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -pyridine, 3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thioρhen-3-yl- [1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
4-[4-Ethyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[lJ2,4]triazol-3-yl]-pyridine,
3-[4-Ethyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine, 3-(4-Ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl-phenyl)-
[1,2,4] oxadiazole,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine,
3-{4-Ethyl-5-[5-(2-fluoro-5-methyl-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H- [1 ,2,4]triazol-3-yl}-pyridine,
3-[5-(3-Chloro-phenyl)-[l ,2,4]oxadiazol-3-ylmethylsulfanyl]-5-pyridin-4-yl-[l ,2,4]triazol-4- ylamine,
4-{5-[5-(5-Bromo-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-2-yl-
[1,2,4] oxadiazole,
3-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-phenyl-[l,2,4]oxadiazole, 4-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2- methoxy-pyridine,
3-(3-Chloro-ρhenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
2-Methyl-4-[3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine,
4.[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2- methyl-pyridine, 5-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-2-yl-
[1,2,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[1 ,2,4]triazol-3-yl} -pyridine,
4-[3-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2- methyl-pyridine, 3-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -benzonitrile,
5-(3-Chloro-phenyl)-3-[5-(3-chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3 - [5-(4-chloro-phenyl)-4-methyl-4H-[ 1 ,2,4]triazol-3 -ylsulfanylmethyl] -
[1,2,4] oxadiazole,
4-{5-[5-(2,5-Dichloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(2,5-Dichloro-phenyl)-3-(4-ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole,
5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
4-{5-[5-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3- yl}-pyridine, 5-(2,5-Dichloro-phenyl)-3-(4-ethyl-5-thioρhen-3-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ρropyl-4H-[l,2,4]triazol-3- yl} -pyridine,
4-{5-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-propyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[1,2,4] oxadiazole, 3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[1,2,4] oxadiazole,
4-[4-Methyl-5-(3-thiophen-3-yl-[l,2,4]oxadiazol-5-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl- [1,2,4] oxadiazole,
5-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl-
[1,2,4] oxadiazole,
5-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- thiophene-3 -carbonitrile, 5-(3-Chloro-phenyl)-3-[5-(2-fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]- [1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[5-(3-fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[5-(4-fluoro-ρhenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]- [ 1 ,2,4] oxadiazole,
3-(5-Benzo[b]thiophen-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro- phenyl)- [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(3-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,2,4]oxadiazole, 5-(3-Chloro-phenyl)-3-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl-phenyl)-
[l,2,4]oxadiazole,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole, 3-(4-Ethyl-5-trifluoromethyl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l ,2,4] oxadiazole,
3-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-pyridin-4-yl-
[ 1 ,2,4]triazol-4-ylamine,
3-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thiophen-2-yl- [ 1 ,2,4]triazol-4-ylamine,
3-Pyridin-4-yl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-[l,2,4]triazol-4-ylamine,
3-Thiophen-2-yl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-[l,2,4]triazol-4-ylamine,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
4-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2- methyl-pyridine,
5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 4-[4-Ethyl-5-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
4-Ethyl-3 -furan-2-yl-5 -(5 -thiophen-3 -yl-isoxazol-3 -ylmethylsulfanyl)-4H- [ 1 ,2,4]triazole,
5-(3-Chloro-phenyl)-3-[5-(3,5-dichloro-ρhenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-(4-ethyl-5-m-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-nitro-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole, 4-{5-[3-(3-Chloro-ρhenyl)-isoxazol-5-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3-yl}- pyridine,
5-(3-Chloro-ρhenyl)-3-[5-(2,5-difluoro-ρhenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(3-chloro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]- [l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(4-chloro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,2,4]oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}-pyridine,
3-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazole, 3-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-[l,2,4]triazole,
5-(2-Chloro-5-methyl-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-{5-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine, 3-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazole,
3-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-[l,2,4]triazole,
4-{5-[5-(2-Fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(2,5-Dichloro-thiophen-3-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
4-{5-[5-(2,5-Dichloro-thiophen-3-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-4H-[l,2,4]triazol-3- yl}-pyridine, 4-Ethyl-3-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-4H-
[l,2,4]triazole,
4-Ethyl-3-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-5-furan-2-yl-4H-
[l,2,4]triazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole, 3-(3-Chloro-phenyl)-5-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thioρhen-3-yl-
[l,2,4]oxadiazole, 5-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-fluoro-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-fluoro-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]- [1,2,4] oxadiazole,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[l,2,4]oxadiazole,
3-{3-[5-(3-Chloro-thioρhen-2-yl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[ 1 ,2,4] oxadiazol-5-yl} -benzonitrile, 4-{5-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
2-(3-Chloro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,3,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(2-fluoro-5-methyl-phenyl)-4-furan-2-ylmethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
4-[3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2- methyl-pyridine, 3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-methoxy-phenyl)-
[l,2,4]oxadiazole,
5-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triaz'ol-3-ylsulfanylmethyl)-3-(3-methoxy-phenyl)-
[1,2,4] oxadiazole,
5 -(4-Ethyl-5-trifluoromethyl-4H- [ 1 ,2,4]triazol-3 -ylsulfanylmethyl)-3 -thiophen-2-yl- [l,2,4]oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
3-[3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile, 3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-trifluoromethyl-4H- [l,2,4]triazole,
3-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazole,
4-Ethyl-3-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-5-trifluoromethyl-4H-[l,2,4]triazole,
4-{3-[5-(3-Fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-[l,2,4]oxadiazol-5- yl}-2-methyl-pyridine,
4-{3-[5-(3-Chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-[l,2,4]oxadiazol-5- y 1 } -2-methyl-pyridine,
4-{3-[5-(4-Chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-[l,2,4]oxadiazol-5- yl } -2-methyl-pyridine, 4-{3-[5-(4-Methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-[l,2,4]oxadiazol-5- yl } -2-methyl-pyridine,
4-[3-(4-Ethyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2-methyl- pyridine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-fluoro-phenyl)- [ 1 ,2,4] oxadiazole,
4-{4-Ethyl-5-[5-(3-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-[l,2,4]triazol-3-yl}- pyridine,
5-(3-Chloro-phenyl)-3-[5-(3,5-difluoro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-[5-(2,6-difluoro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole,
2-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-4- methyl-phenol,
3-{l-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-5-furan-2-yl-4H-[l,2,4]triazole, 4-(5-{l-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3-yl)- pyridine,
3-[5-(4-Butoxy-phenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
3-(5-Benzo[l,3]dioxol-5-yl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)- [1 ,2,4] oxadiazole,
3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-methyl-thiazol-4-yl)-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-fluoro-phenyl)-
[1,2,4] oxadiazole, 4-Ethyl-3-{l-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-5-furan-2-yl-4H- [l,2,4]triazole,
4-(4-Ethyl-5-{l-[5-(2-fluoro-5-methyl-ρhenyl)-isoxazol-3-yl]-ethylsulfanyl}-4H-[l,2,4]triazol-
3-yl)-pyridine,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methyl-3H-imidazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(l-methyl-lH-imidazol-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(l-methyl-lH-imidazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 4-{5-[5-(3-Chloro-phenyl)-4-methyl-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3- yl}-pyridine,
3-[5-(3-Chloro-phenyl)-4-methyl-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-methyl-thiophen-2-yl)- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methyl-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(5-methyl-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole, 4-{5-[4-Chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3- yl} -pyridine,
3-[4-Chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
2-Chloro-4-{5-[5-(3-chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-6-methyl-pyridine,
3-[5-(5-Bromo-furan-2-yl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
2-Chloro-4-{5-[5-(3-chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 2-Chloro-4-{5-[5-(3-chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-6-methoxy-pyridine,
2-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-4- methyl-benzonitrile,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methoxy-thioρhen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1 ,2,4]oxadiazole, 3-[5-(5-Chloro-thiophen-3-yl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
3-[3-(4-E l-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-5- fluoro-benzonitrile, 4-Ethyl-3-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-5-thiophen-2-yl-4H-[l,2,4]triazole,
4-Methyl-3-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-5-thiophen-3-yl-4H-[l,2,4]triazole,
4-Ethyl-3-furan-2-yl-5-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazole,
4-[4-Ethyl-5-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
4-[4-Methyl-5-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine, 2-(4-Ethyl-5-furan-2-yl-4H-[l ,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l ,3,4]oxadiazole,
4-[4-Methyl-5-(5-m-tolyl-[l,3,4]oxadiazol-2-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
4-[4-Ethyl-5-(5-m-tolyl-[l,3,4]oxadiazol-2-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
4-{5-[5-(5-Chloro-thiophen-3-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4] triazol-3 -yl } -pyridine, 3-[3-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-4- fluoro-benzonitrile,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-4- fluoro-benzonitrile,
3-[3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-4- fluoro-benzonitrile,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
3-[5-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- benzonitrile, 3-[3-(4-Methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
2-Chloro-4-[3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -pyridine,
2-Chloro-4-[3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -pyridine,
2-(3-Chloro-phenyl)-5-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,3 ,4] oxadiazole, 2-(3-Chloro-phenyl)-5-(4-methyl-5-thiazol-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,3,4]oxadiazole,
2-(3-Cmoro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,3 ,4] oxadiazole,
2-(3-Chloro-phenyl)-5-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,3,4]oxadiazole,
4-{4-Ethyl-5-[5-(4-methyl-thiophen-2-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[l,2,4]triazol-3-yl}-pyridine,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-methyl-thiophen-2-yl)-
[1,2,4] oxadiazole, 3-(3-Chloro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-{5-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
4-{4-Ethyl-5-[5-(3-nitro-ρhenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4H-[l,2,4]triazol-3-yl}- pyridine,
2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-nitro-phenyl)-
[1,3, 4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H-[l,2,4]triazol-3-yl}- pyridine, 3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-(4-methoxy-phenyl)-4H-
[l,2,4]triazole,
5-(3-Chloro-ρhenyl)-3-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[l-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]- [ 1 ,2,4] oxadiazole,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridine, 3-[5-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2-yl]- benzonitrile,
3-[5-(4-E l-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2-yl]- benzonitrile,
3-[5-(4-Methyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2-yl]- benzonitrile, 3-[5-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -benzonitrile,
4-{5-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine, 4-{5-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-cyclopropyl-4H-
[1 ,2,4]triazol-3-yl}-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-cyclopropyl-4H-
[1 ,2,4]triazol-3-yl} -pyridine,
2-(5-Chloro-2-fluoro-phenyl)-5-[4-ethyl-5-(4-methoxy-ρhenyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l ,3 ,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine, 2-(3-Chloro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,3,4]oxadiazole,
2-(3-Chloro-phenyl)-5-[l-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[l,3,4]oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)- ethyl] - [ 1 ,2,4] oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine, 2-Chloro-4-[3-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine,
4- { 5 - [5 -(2-Fluoro-5 -methyl-phenyl)- [1,3,4] oxadiazol-2-ylmethy lsulfany 1] -4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4H- [l,2,4]triazol-3-yl}-pyridine,
4-{4-Cyclopropyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine,
2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl-phenyl)-
[1,3 ,4] oxadiazole, 2-[4-Ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(2-fluoro-5-methyl- phenyl)-[l ,3,4]oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3- yl} -pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine, 4-{5-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
4-(5-{l-[5-(5 -Chloro-2-fluoro-phenyl)-isoxazol-3 -yl] -ethylsulfanyl } -4-cyclopropyl-4H-
[l,2,4]triazol-3-yl)-pyridine,
3-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H- [l,2,4]triazole,
3-{l-[5-(5 -Chloro-2-fluoro-phenyl)-isoxazol-3 -yl] -ethylsulfanyl } -4-ethyl-5 -furan-2-yl-4H-
[l,2,4]triazole,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
5-(5-Chloro-2-fluoro-phenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-(5-furan-3-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-Chloro-2-[3-(4-ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl] -phenol, 2-Chloro-4-[5-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-
2-yl] -pyridine,
2-Chloro-4-[5-(4-ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -pyridine,
2-Chloro-4-[5-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,3,4]oxadiazol-2-yl]-pyridine, 2-Cmoro-4-[5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -pyridine,
2-Chloro-4-{5-[4-ethyl-5-(4-methoxy-ρhenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[ 1 ,3 ,4] oxadiazol-2-yl} -pyridine, 2-(3-Chloro-phenyl)-5-{l-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]- ethyl}-[l ,3,4] oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
5-(5-Bromo-2-fluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4] oxadiazole,
2-(3-Chloro-phenyl)-5-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,3,4]oxadiazole,
4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl} -pyridine, 4-{5-[5-(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-cyclopropyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4-(5 - { 1 - [5-(2-Fluoro-5 -methyl-phenyl)- [1,3,4] oxadiazol-2-yl] -ethylsulfanyl } -4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-(4-Ethyl-5-{l-[5-(2-fluoro-5-methyl-ρhenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4H- [ 1 ,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-(4-Cyclopropylmethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-yl]- ethylsulfanyl}-4H-[l,2,4]triazol-3-yl)-pyridine, 2-(2-Fluoro-5-methyl-phenyl)-5-{ 1 -[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-[l ,2,4]triazol-3- ylsulfanyl]-ethyl}-[l,3,4]oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-cyclopropyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
2-(5-Cmoro-2-fluoro-phenyl)-5-[l-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[1,3, 4] oxadiazole,
2-(5-Chloro-2-fluoro-phenyl)-5-{l-[4-memyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanyl] -ethyl } - [ 1 ,3 ,4] oxadiazole, 4-(4-Cyclopropylmethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4H- [ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
4-(4-Cycloproρyl-5-{l-[5-(3-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4H- [l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(4-Methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-
[l,3,4]oxadiazol-2-yl)-2-methyl-pyridine,
4-(5-{l-[4-Ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-[l,3,4]oxadiazol-
2-yl)-2-methyl-pyridine, 4-{5-[l-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,3,4]oxadiazol-2-yl}-2- methyl-pyridine,
4-{5-[l-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,3,4]oxadiazol-2- yl } -2-methyl-pyridine,
4-{5-[l-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,3,4]oxadiazol-2-yl}-2- methyl-pyridine,
2-(3-Chloro-phenyl)-5-{l-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3-ylsulfanyl]- ethyl}-[l ,3,4]oxadiazole,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-
3 -yl)-2-methyl-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-cycloproρyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
5-(3-Chloro-ρhenyl)-3-{l-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]- ethyl} -[1,2,4] oxadiazole,
4-(5- { 1 - [5-(5-Chloro-2-fluoro-ρhenyl)- [ 1 ,2,4] oxadiazol-3 -yl] -ethylsulfanyl } -4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
5-(5-Chloro-2-fluoro-phenyl)-3-{l-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanyl] -ethyl} - [ 1 ,2,4] oxadiazole, 4-[5-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2-yl]-2- methyl-pyridine,
4-[5-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -2-methyl-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H- [l,2,4]triazol-3-yl} -pyridine, 4-[5-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2-yl]-2- methyl-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-cyclopropylmethyl-4H-
[l,2,4]triazol-3-yl)-pyridine, 4-(5-{l-[5-(4-Fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-[l,3,4]oxadiazol-
2-yl)-2-methyl-pyridine,
4-(5-{l-[5-(3-Fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-[l,3,4]oxadiazol-
2-yl)-2-methyl-pyridine,
3-[3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl]-4-fluoro-benzonitrile,
4-Chloro-2-[3-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1 ,2,4]oxadiazol-5-yl]-phenol,
4- {4-Cyclopropyl-5-[5-(3-methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4H-
[ 1 ,2,4] triazol-3 -yl } -pyridine, 4-{4-Cyclopropyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[1 ,2,4]triazol-3-yl}-pyridine,
4- {4-Cyclopropyl-5 - [5 -(3 -fluoro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4H-
[l,2,4]triazol-3-yl}-pyridine,
4-[4-Cyclopropyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3 - [3 -(4-Cyclopropyl-5-pyridin-4-yl-4H- [ 1 ,2,4] triazol-3 -ylsulfanylmethyl)- [1,2,4] oxadiazol-5 - yl]-benzonitrile,
4-{4-Cyclopropyl-5-[5-(2,5-difluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[1 ,2,4]triazol-3-yl}-pyridine, 4-{4-Cycloρropyl-5-[l-(5-m-tolyl-[l,2,4]oxadiazol-3-yl)-ethylsulfanyl]-4H-[l,2,4]triazol-3-yl}- pyridine,
4-(4-Cyclopropyl-5 - { 1 - [5 -(3 -methoxy-phenyl)- [1,2,4] oxadiazol-3 -yl] -ethylsulfanyl} -4H-
[l,2,4]triazol-3-yl)-pyridine,
4-{5-[5-(2-Chloro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H- [l,2,4]triazol-3-yl}-pyridine,
2-[3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-methyl-phenol,
4-(5-{l-[5-(2-Chloro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine, {3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- phenyl } -methanol,
3-[5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- phenol,
5-(3-Cmoro-phenyl)-3-[4-(tetrahydro-furan-2-ylmethyl)-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
(2-Chloro-phenyl)-{5-[5-(3-chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-isobutyl-4H-
[ 1 ,2,4]triazol-3 -yl} -methanol,
5-(2-Fluoro-5-methyl-phenyl)-3-[5-thiophen-2-yl-4-(2,2,2-trifluoro-ethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 3-(2,5-Difluoro-phenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-Furan-3-yl-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole,
3-(3-Chloro-phenyl)-5-(5-furan-3-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-(5-furan-3-yl-4-methyl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl}-pyrimidine,
4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl}-pyrimidine,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5-(5-Chloro-thiophen-2-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(5-Chloro-thiophen-2-yl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(5-CMoro-thiophen-3-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole, 4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3- ylmethoxy } -phenol,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-ylmethoxy}-phenol, 3-(2,5-Difluoro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(2,5-Difluoro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-(5-{l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol- 3-yl)-pyridine,
4-{5-[5-(5 -Chloro-2-fluoro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl} -pyrimidine,
2-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-5 -methoxy-pyrimidine, 2-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyrimidine,
4-(5-{l-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-2-methoxy-pyridine,
5-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-2-methoxy-pyridine,
2-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-5 -methoxy-pyridine,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-6-methoxy-pyridazine, 3-(5-{ 1 -[5-(3-Chloro-phenyl)-[l ,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-cycloρropyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-isobutyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methylsulfanyl-propyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-hexyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-(4-cyclopropylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-fluoro-benzyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methyl-benzyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(2-methyl-butyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methyl-butyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-[4-(2-fluoro-benzyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yloxymethyl)-
[1,2,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethoxy]-4-methyl-4H-[l,2,4]triazol- 3-yl}-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethoxy}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
4-(5-{l-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethoxy}-4-methyl-4H-[l,2,4]triazol-3-yl)-pyridine,
5-(2-Methoxy-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-Furan-2-yl-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzoic acid methyl ester, 5-(2-Fluoro-ρhenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(2,5-Difluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-vinyl-phenyl)- [l,2,4]oxadiazole,
5 -(3 -Difluoromethoxy-phenyl)-3 -(4-methyl-5 -thiophen-2-yl-4H- [ 1 ,2,4]triazol-3 - ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(4-Methoxy-thiophen-3-yl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 5-(2-Chloro-ρhenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(4-Fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-[l-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]- [1,2,4] oxadiazole,
-(5-{l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-3- yl)-pyridine,
3-(3-Chloro-phenyl)-5-[2-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylmethyl)-[l,2,4]oxadiazole,
2-(3-Chloro-phenyl)-5-[2-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[l,3,4]oxadiazole,
2-(3-Chloro-phenyl)-5-[2-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-[l,3,4]oxadiazole,
2-(3-CMoro-phenyl)-5-[2-(4-cyclopropyl-5-furan-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]- [l,3,4]oxadiazole,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-ethyl-4H-[l,2,4]triazol-3-yl)- pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-cyclopropyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-4-cyclopropyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-methyl-propyl}-4-cyclopropyl-4H- [l,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-propyl}-4-cycloρropyl-4H-[l,2,4]triazol-3- yl)-pyridine,
8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[ 1 ,2,4]triazolo [4,3 -a] pyridine, 8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-thiophen-2-yl-5,6,7,8-tetrahydro-
[1 ,2,4]triazolo[4,3-a]pyridine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[1 ,2,4]triazolo[4,3-a]pyridine,
5-(5-Bromo-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-(3-chloro-phenyl)- [1,2,4] oxadiazole, 3-[3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- phenylamine,
5-(3-Chloro-phenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazole-3-sulfonylmethyl)-
[1,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[ 1 ,2,4]triazole-3-sulfinylmethyl)-
[1,2,4] oxadiazole,
2-Methyl-6-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridin-2-ol,
4-(5-{2-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-propyl}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
[5 -(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethyl] -methyl-(4-methyl-5 -pyridin-4-yl-4H-
[1 ,2,4]triazol-3-yl)-amine, 8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[l,2,4]triazolo[4,3-a]pyrimidine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[ 1 ,2,4]triazolo[4,3-a]pyrimidine,
8-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro- [1 ,2,4]triazolo[4,3-a]pyrimidine,
8-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethyl}-3-ρyridin-4-yl-5,6,7,8-tetrahydro-
[l,2,4]triazolo[4,3-a]pyrimidine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-furan-2-yl-5,6,7,8-tetrahydro-
[l,2,4]triazolo[4,3-a]pyrimidine, 8-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethyl}-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[l,2,4]triazolo[4,3-a]pyrimidine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(lH-pyrrol-3-yl)-
[1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine 1 -oxide,
5-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-
[l,2,4]oxadiazole, 5-(5-Chloro-2-fluoro-phenyl)-3-[4-(2-fluoro-ethyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole, 5-(5-Chloro-thiophen-3-yl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-4- hydroxy-benzonitrile,
3-(3-Chloro-phenyl)-5-[2-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]- [ 1 ,2,4] oxadiazole,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-[l,3,4]oxadiazol-2-yl)-pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-4-cyclopropyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
4-(5- {2- [3-(3-Chloro-phenyl)- [ 1 ,2,4] oxadiazol-5-yl] -cyclopropyl} -4-cyclopropyl-4H- [l,2,4]triazol-3-yl)-pyridine, or
4-(5-{2-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-l,l-dimethyl-ethyl}-[l,3,4]oxadiazol-2-yl)- pyridine,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethoxy}-4-cyclopropyl-4H-[l,2,4]triazol-3- yl)-pyridine, 4-(5-{ 1 -[5-(2-Chloro-5-methyl-phenyl)-[l ,2,4] oxadiazol-3 -yl] -ethylsulfanyl }-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H- [l,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
3-{3-[l-(4-Methyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,2,4]oxadiazol-5-yl}- benzonitrile, 3-{3-[l-(4-Cycloproρyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,2,4]oxadiazol-5- yl} -benzonitrile,
3-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-5-pyridin-4-yl-[l,2,4]triazol-4- ylamine,
3-(3-Chloro-phenyl)-5-[2-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]- [1,2,4] oxadiazole,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine, cis-4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-4-cyclopropyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l,l-dimethyl-ethyl}-[l,3,4]oxadiazol-2-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-methyl-propyl}-[l,3,4]oxadiazol-2-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-[l,3,4]oxadiazol-2-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-[l,3,4]oxadiazol-2-yl)- pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cycloproρyl}-4-methyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{2-[5-(3-Chloro-ρhenyl)-[l,3,4]oxadiazol-2-yl]-proρyl}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-[l,3,4]oxadiazol-2-yl)-pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ρropyl}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ρropyl}-4-cyclopropyl-4H-[l,2,4]triazol-3- yl)-pyridine,
(S)-[l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H- [1 ,2,4]triazol-3-yl)-ethyl]-carbamic acid tert-butyl ester,
(S)-l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cycloproρyl-5-ρyridin-4-yl-4H-
[l,2,4]triazol-3-yl)-ethylamine,
(S)-[l-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H-
[ 1 ,2,4]triazol-3-yl)-ethyl]-dimethyl-amine, or a salt thereof.
The compounds of formula I useful in accordance with the present invention, may also be used as pharmaceutically acceptable salts, but also other salts may be useful in accordance with the present invention.
Examples of pharmaceutically acceptable salts useful in accordance with the present invention are, but are not limited to, hydrochloride, 4-aminobenzoate, anthranilate, 4-aminosalicylate, 4- hydroxybenzoate, 3,4-dihydroxybenzoate, 3-hydroxy-2-naphthoate, nitrate and trifluoroacetate.
Some compounds of formula I may have chiral centres and/or geometric isomeric centres (E- and Z- isomers), and it is to be understood that the invention encompasses the use of all such optical, diastereoisomers and geometric isomers.
The invention also relates to the use of any and all tautomeric forms of the compounds of formula I, la or lb.
A further aspect of the invention is the use of a compound formula I, la or lb for the manufacture of a medicament for the prevention of reflux.
Still a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment of gastro-esophageal reflux disease (GERD).
Effective prevention of regurgitation would be an important way of preventing, as well as curing lung disease due to aspiration of regurgitated gastric contents, and for managing failure to thrive. Thus, a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment of regurgitation.
Still a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment or prevention of lung disease.
Another aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the management of failure to thrive.
Still a further aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment or prevention of asthma, such as reflux-related asthma.
A further aspect of the invention is the use of a compound according to formula I, la or lb for the manufacture of a medicament for the treatment or prevention of functional gastrointestinal disorders, such as functional dyspepsia (FD). Yet another aspect of the invention is the use of a compound according to formula I, la or lb for the manufacture of a medicament for the treatment or prevention of irritable bowel syndrome (IBS), such as constipation predominant IBS, diarrhea predominant IBS or alternating bowel movement predominant IBS. Another aspect of the invention is the use of a compound of formula I, la or lb for the manufacture of a medicament for the treatment or prevention of chronic laryngitis.
A further aspect of the present invention is a method for the inhibition of transient lower esophageal sphincter relaxations (TLESRs), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such inhibition.
Another aspect of the invention is a method for the prevention of reflux, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such prevention.
Still a further aspect of the invention is a method for the treatment of gastro-esophageal reflux disease (GERD), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
Yet another aspect of the invention is a method for the treatment of regurgitation, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula
I, la or lb is administered to a subject in need of such treatment.
Still a further aspect of the invention is a method for the treatment or prevention of asthma, such as reflux-related asthma, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
Yet another aspect of the invention is a method for the treatment of chronic laryngitis, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
Still a further aspect of the invention is a method for the treatment or inhibition of lung disease, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
Still a further aspect of the invention is a method for the management of failure to thrive, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I, la or lb is administered to a subject in need of such treatment.
The wording "TLESR", transient lower esophageal sphincter relaxations, is herein defined in accordance with Mittal, R.K., Holloway, R.H., Penagini, R., Blackshaw, L.A., Dent, J, 1995; Transient lower esophageal sphincter relaxation. Gastroenterology 109, pp. 601-610.
The wording "reflux" is defined as fluid from the stomach being able to pass into the esophagus, since the mechanical barrier is temporarily lost at such times.
The wording "GERD", gastro-esophageal reflux disease, is defined in accordance with van Heerwarden, M.A., Smout A.J.P.M., 2000; Diagnosis of reflux disease. Bailliere 's Clin. Gastroenterol. 14, pp. 759-774.
Pharmaceutical formulations
For clinical use, the compounds of formula I, la or lb are in accordance with the present invention suitably formulated into pharmaceutical formulations for oral administration. Also rectal, parenteral or any other route of administration may be contemplated to the skilled man in the art of formulations. Thus, the compounds of formula I, la or lb are formulated with at least one pharmaceutically and pharmacologically acceptable carrier or adjuvant. The carrier may be in the form of a solid, semi-solid or liquid diluent.
In the preparation of oral pharmaceutical formulations in accordance with the invention, the compound of formula I, la or lb to be formulated is mixed with solid, powdered ingredients such as lactose, saccharose, sorbitol, mannitol, starch, amylopectin, cellulose derivatives, gelatin, or another suitable ingredient, as well as with disintegrating agents and lubricating agents such as magnesium stearate, calcium stearate, sodium stearyl fumarate and polyethylene glycol waxes. The mixture is then processed into granules or compressed into tablets.
Soft gelatine capsules may be prepared with capsules containing a mixture of the active compound or compounds of the invention, vegetable oil, fat, or other suitable vehicle for soft gelatine capsules. Hard gelatine capsules may contain the active compound in combination with solid powdered ingredients such as lactose, saccharose, sorbitol, mannitol, potato starch, corn starch, amylopectin, cellulose derivatives or gelatine.
Dosage units for rectal administration may be prepared (i) in the form of suppositories which contain the active substance(s) mixed with a neutral fat base; (ii) in the form of a gelatine rectal capsule which contains the active substance in a mixture with a vegetable oil, paraffin oil, or other suitable vehicle for gelatine rectal capsules; (iii) in the form of a ready-made micro enema; or (iv) in the form of a dry micro enema formulation to be reconstituted in a suitable solvent just prior to administration.
Liquid preparations for oral administration may be prepared in the form of syrups or suspensions, e.g. solutions or suspensions, containing the active compound and the remainder of the formulation consisting of sugar or sugar alcohols, and a mixture of ethanol, water, glycerol, propylene glycol and polyethylene glycol. If desired, such liquid preparations may contain colouring agents, flavouring agents, saccharine and carboxymethyl cellulose or other thickening agent. Liquid preparations for oral administration may also be prepared in the form of a dry powder to be reconstituted with a suitable solvent prior to use.
Solutions for parenteral administration may be prepared as a solution of a compound of the invention in a pharmaceutically acceptable solvent. These solutions may also contain stabilizing ingredients and/or buffering ingredients and are dispensed into unit doses in the form of ampoules or vials. Solutions for parenteral administration may also be prepared as a dry preparation to be reconstituted with a suitable solvent extemporaneously before use.
In one aspect of the present invention, the compound of formula I, la or lb may be administered once or twice daily, depending on the severity of the patient's condition.
Methods of Preparation
The compounds in accordance with the present invention can be prepared as described in Biological evaluation
Screening for compounds active against TLESR
Adult Labrador retrievers of both genders, trained to stand in a Pavlov sling, are used. Mucosa- to-skin esophagostomies are formed and the dogs are allowed to recover completely before any experiments are done.
Motility measurement
In brief, after fasting for approximately 17 h with free supply of water, a multilumen sleeve/sidehole assembly (Dentsleeve, Adelaide, South Australia) is introduced through the esophagostomy to measure gastric, lower esophageal sphincter (LES) and esophageal pressures. The assembly is perfused with water using a low-compliance manometric perfusion pump (Dentsleeve, Adelaide, South Australia). An air-perfused tube is passed in the oral direction to measure swallows, and an antimony electrode monitored pH, 3 cm above the LES. All signals are amplified and acquired on a personal computer at 10 Hz.
When a baseline measurement free from fasting gastric/LES phase III motor activity has been obtained, placebo (0.9% NaCl) or test compound is administered intravenously (i.v., 0.5 ml/kg) in a foreleg vein. Ten min after i.v. administration, a nutrient meal (10% peptone, 5% D-glucose, 5% Intralipid, pH 3.0) is infused into the stomach through the central lumen of the assembly at 100 ml/min to a final volume of 30 ml/kg. Immediately following the meal, air is insufflated at 40 ml/min. In an alternative model (Barostat model), the infusion of the nutrient meal is followed by air infusion at a rate of 500 ml/min until a intragastric pressure of 10+1 mmHg is obtained. The pressure is then maintained at this level throughout the experiment using the infusion pump for further air infusion or for venting air from the stomach. The experimental time from start of nutrient infusion to end of air insufflation is 45 min. The procedure has been validated as a reliable means of triggering TLESRs.
TLESRs is defined as a decrease in lower esophageal sphincter pressure (with reference to intragastric pressure) at a rate of >1 mmHg/s. The relaxation should not be preceded by a pharyngeal signal <2s before its onset in which case the relaxation is classified as swallow- induced. The pressure difference between the LES and the stomach should be less than 2 mmHg, and the duration of the complete relaxation longer than 1 s.

Claims

Claims
1. Use of a compound formula la
Figure imgf000049_0001
(la) wherein:
P is selected from the group consisting of hydrogen, C3. alkyl or a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; R1 is selected from the group consisting of hydrogen, hydroxy, halo, nitro, d-6alkylhalo, Od_6alkylhalo, d-βalkyl, Od-6alkyl, d-βalkenyl, Od-βalkenyl, d-βalkynyl, OC2- 6alkynyl, C0.6alkylC3-6cycloalkyl, OCo-6alkylC3-6cycloalkyl, Co-6alkylaryl, OCo-6alkylaryl, CHO, (CO)R5, O(CO)R5, O(CO)OR5, O(CN)OR5, d.6alkylOR5, OC2.6alkylOR5, d_
6alkyl(CO)R5, Od.6alkyl(CO)R5, C0.6alkylCO2R5, Od.6alkylCO2R5, C0.6alkylcyano, OC2. 6alkylcyano, C0-6alkylNR5R6, OC2.6alkylNR5R6, d.6alkyl(CO)NR5R6, Od- 6alkyl(CO)NR5R6, C0-6alkylNR5(CO)R6, OC2.6alkylNR5(CO)R6, C0.6alkylNR5(CO)NR5R6, Co-ealkylSR5, OC2.6alkylSR5, C0.6alkyl(SO)R5, OC2-6alkyl(SO)R5, Co-6alkylSO2R5, OC2. 6alkylSO2R5, C0-6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6,C0.6alkylNR5(SO2)R6, OC2-
6alkylNR5(SO2)R6, Co.6alkylNR5(SO2)NR5R6, OC2-6alkylNR5(SO2)NR5R6, (CO)NR5R6, O(CO)NR5R6, NR5OR6, C0.6alkylNR5(CO)OR6, OC2.6alkylNR5(CO)OR6, SO3R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S, wherein said ring may be substituted by one or more A; M1 is selected from the group consisting of a bond, d-3alkyl, d-salkenyl, d^alkynyl, Co-
4alkyl(CO)C0.4alkyl, Co-salkylOCo-salkyl, C0.3alkyl(CO)NR5, Co.3alkyl(CO)NR5Co-3alkyl, C0-4alkylNR5, C0.3alkylSCo.3alkyl, C0.3alkyl(SO)C0.3 alkyl or C0.3alkyl(SO2)Co-3alkyl; R2 is selected from the group consisting of hydrogen, hydroxy, Co-6alkylcyano, oxo, =NR5, =NOR5, d.4alkylhalo, halo, d.4alkyl, O(CO)d.4alkyl, d.4alkyl(SO)C0. alkyl, CL 4alkyl(SO2)C0-4alkyl, (SO)C0-4alkyl, (SO2)C0-4alkyl, OC^alkyl, d.4alkylOR5 and C0.
4alkylNR5R6; X1, X2 and X3 are independently selected from the group consisting of CR, CO, N, NR, O and S;
R is selected from the group consisting of hydrogen, Co-3alkyl, halo, Co-3alkylOR5, Co- 3alkylNR5R6, C0.3alkyl(CO)OR5, Co-3alkylNR5R6 and C0.3alkylaryl; M2 is selected from a group consisting of a bond, d-3alkyl, C3- cycloalkyl, C2-3alkenyl,
C2.3alkynyl, C0.4alkyl(CO)Co.4alkyl, Co.3alkylOCo-3alkyl, Co-3alkylNR5d-3alkyl, C0. 3alkyl(CO)NR5, C0.4alkylNR5, C0.3alkylSCo-3alkyl, C0.3alkyl(SO)Co.3alkyl and C0. 3alkyl(SO2)Co-3alkyl; R3 is selected from a group consisting of hydrogen, hydroxy, Co-6alkylcyano, oxo, =NR5, =NOR5, d.4alkylhalo, halo, d.4alkyl, O(CO)C1.4alkyl, d.4alkyl(SO)C0.4alkyl, d.
4alkyl(SO2)C0.4alkyl, (SO)C0. alkyl, (SO2)C0.4alkyl, OC1.4alkyl, C alkylOR5 and C0.
4alkylNR5R6;
X4 is selected from the group consisting of Co-4alkylR5, Co-4alkyl(NR5R6), Co-
4alkyl(NR5R6)=N, NR5Co-4alkyl(NR5R6)=N, NOCo.4alkyl, d.4alkylhalo, C, O, SO, SO2 and S;
Q is a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S, which group may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S and which fused ring may be substituted by one or more A; R4 is selected from the group consisting of hydrogen, hydroxy, Co-6alkylcyano, oxo,
=NR5, =NOR5, d.4alkylhalo, halo, C alkyl, Od.4alkyl, OC0-6alkylaryl, O(CO)d_ 4alkyl5 C0-4alkyl(S)C0. alkyl, d.4alkyl(SO)C0.4alkyl, d.4alkyl(SO2)Co.4alkyl, (SO)C0- 4alkyl, (SO2)C0.4alkyl, d.4alkylOR5, Co-4alkylNR5R6 and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O or S, wherein said ring may be substituted by one or more A;
R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, d- 6alkyl, Co-6alkylC3.6cycloalkyl, Co-6alkylaryl, Co.6alkylheteroaryl and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O and S, and wherein R5 and R6 may together form a 5- or 6-membered ring containing one or more atoms independently selected from the goup consisting of C, N, O and S; wherein any d.6alkyl, C2.6alkenyl, C2.6alkynyl, Co-6alkylC3.6cycloalkyl, Co-6alkylaryl and Co-6alkylheteroaryl defined under R1, R2, R3, R4, R5 and R6 may be substituted by one or more A; A is selected from the group consisting of hydrogen, hydroxy, oxo, halo, nitro, Co- 6alkylcyano, d. alkyl, Co-4alkylC3.6cycloalkyl, Cι-6alkylhalo, Od.6alkylhalo, C2_ 6alkenyl, Od_6alkyl, C0.3 alkylaryl, C0.6alkylOR5, OC2.6alkylOR5, d.6alkylSR5, OC2. 6alkylSR5, (CO)R5, O(CO)R5, OC2-6alkylcyano, C0.6alkylCO2R5, Od-6alkylCO2R5, O(CO)OR5, Od.6alkyl(CO)R5, d.6alkyl(CO)R5, NR5OR6, C0-6alkylNR5R6, OC2.
6alkylNR ,55 nR6b, Co.6alkyl(CO)NR )5DπR6D, Od.6alkyl(CO)NR 5DRr 6°, OC2.6alkylNR5(CO)R6, C0.
6alkylNR5(CO)R6,
C0-6alkylNR5(CO)NR5R6, O(CO)NR5R6, NR5(CO)OR6, C0.6alkyl(SO2)NR5R6,
OC2.6alkyl(SO2)NR5R6, C0.6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, SO3R5, d.6alkylNR5(SO2)NR5R6, OC2.6alkyl(SO2)R5, Co-6alkyl(SO2)R5, C0.6alkyl(SO)R5,
OC2-6alkyl(SO)R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; m is selected from 0, 1, 2, 3 and 4; and n is selected from 0, 1, 2 and 3, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the inhibition of transient lower esophageal sphincter relaxations
(TLESRs).
2. Use of a compound of formula I
Figure imgf000051_0001
(I) wherein:
P is selected from the group consisting of thiophene, pyridyl, thiazolyl, furyl, pyrrolyl and phenyl, whereby the phenyl ring is substituted on position 3 or disubstituted on positions
2 and 5;
R1 is attached to P via a carbon atom on ring P and is selected from the group consisting of hydrogen, hydroxy, halo, nitro, d.6alkylhalo, Od-βalkylhalo, Cι-6alkyl, Od.6alkyl, C2. βalkenyl, OC2-6alkenyl, C2.6alkynyl, OC2-6alkynyl, C0.6alkylC3.6cycloalkyl, OCo-6alkylC3. ecycloalkyl, Co-ealkylaryl, OC0.6alkylaryl, CHO, (CO)R5, O(CO)R5, O(CO)OR5,
O(CN)OR5, d-ealkylOR5, OC2.6alkylOR5, d.6alkyl(CO)R5, OC1.6alkyl(CO)R5, C0. 6alkylCO2R5, Od.6alkylCO2R5, C0.6alkylcyano, OC2.6alkylcyano, C0.6alkylNR5R6, OC2.
6alkylNR5R6, d.6alkyl(CO)NR5R6, Od.6alkyl(CO)NR5R6, C0.6alkylNR5(CO)R6, OC2-
6alkylNR5(CO)R6, C0.6alkylNR5(CO)NR5R6, C0.6alkylSR5, OC2-6alkylSR5, C0.
6alkyl(SO)R5, OC2.6alkyl(SO)R5, C0.6alkylSO2R5, OC2.6alkylSO2R5, C0.6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6,Co.6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, C0.
6alkylNR5(SO2)NR5R6, OC2-6alkylNR5(SO2)NR5R6, (CO)NR5R6, O(CO)NR5R6, NR5OR6,
C0.6alkylNR5(CO)OR6, OC2.6alkylNR5(CO)OR6, SO3R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; M1 is a bond;
X1 selected from the group consisting of C, CO, N, O and S;
X is selected from the group consisting of C, N, O and S;
X3 is i) selected from the group consisting of N, O and S, or ii) selected from N, O, S, and C when X2 is selected from N, O, or S, and when X3 is C the substituent R on X3 is H. ;
R is selected from the group consisting of hydrogen, Co-3alkyl, halo, Co-3alkylOR5, Co-
3alkylNR5R6, C0.3alkyl(CO)OR5 and C0.3alkylaryl;
M2 is selected from a group consisting of a bond, d-3alkyl, d^alkynyl, Co-4alkyl(CO)Co-
4alkyl, Co-3alkylOC0.3alkyl, Co.3alkylNR5d.3alkyl, C0-3alkyl(CO)NR5, C0.4alkylNR5, C0- 3alkyl(SO)C0.3alkyl and C0.3alkyl(SO2)Co-3alkyl;
R3 is selected from a group consisting of hydroxy, Co-6alkylcyano, oxo, =NR5, =NOR5, d.4alkylhalo, halo, C alkyl, O(CO)C alkyl, C alkyl(SO)C0.4alkyl, d.4alkyl(SO2)C0.
4alkyl, (SO)C0-4alkyl, (SO2)Co. alkyl, OC1.4alkyl, Cι.4alkylOR5 and C0.4alkylNR5R6;
X4 is selected from the group consisting of Co-4alkylR5R6 , C3. cycloalkyl, d. 4alkyl(NR5R6), NR5, C0-4alkyl(NR5R6)=N, NR5C0-4alkyl(NR5R6)-N, NOC0.4alkyl, d-
4alkylhalo, O, SO, SO2 and S, and wherein the bond between M2 and X4 is a single bond ;
Q is i) selected from the group consisting of triazolyl, imidazolyl, oxadiazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, and wherein any substitutable nitrogen atom in the ring is substituted with R4 on such nitrogen atom and any suitable carbon atom is optionally substituted with R4; and
R4 is selected from the group consisting of Co-6alkylcyano, =NC1.4alkyl, =NOR5, d. 4alkylhalo, halo, d_6alkyl, OCι.4alkyl, C2- alkenyl, Co-2alkylC3.6cycloalkyl, Co. 6alkylaryl, C0.6alkylheteroaryl, OCo-βalkylaryl, OCo-6alkylheteroaryl, NCo-βalkylaryl, NCo-6alkylheteroaryl,Co-6alkylOaryl, Co-βalkylOheteroaryl, Co-6alkylNaryl, Co- 6alkylNheteroaryl, OC0.6alkylOaryl, OCo-6alkylOheteroaryl, OCo-6alkylNaryl, OCQ. eali ylNheteroaryl, NC0-6alkylOaryl, NC0.6alkylOheteroaryl, NCo-6alkylNaryl, NC0. 6alkylNheteroaryl, O(CO)d-4alkyl, Co.4alkyl(CO)OC1.4alkyl, C1-4alkyl(S)Co.4alkyl, d.4alkyl(SO)C0.4alkyl, d.4alkyl(SO2)C0.4alkyl, (SO)C0.4alkyl, (SO2)C0-4alkyl, d. 4alkylOR5, Co.4alkylN(d-4alkyl)2 and a 3- or 6-membered non-aromatic ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A; or ii) selected from the group consisting of benzoimidazolyl, benzooxazolyl, tetrahydrotriazolopyridyl, tetrahydrotriazolopyrimidmyl, pyridonyl, pyridazinyl, imidazopyridyl, oxazolopyridyl, thiazolopyridyl, imidazopyridazinyl, oxazolopyridazinyl, thiazolopyridazinyl and purinyl; and
R4 is selected from the group consisting of hydrogen, hydroxy, Co-βalkylcyano, =NR5, =NOR5, d.4alkylhalo, halo, d-6alkyl, Od.4alkyl, OC0.6alkylaryl, O(CO)d.4alkyl, Co- 4alkyl(S)C0-4alkyl, C1.4alkyl(SO)C0.4alkyl, C1.4alkyl(SO2)Co-4alkyl, (SO)C0.4alkyl,
(SO2)Co-4alkyl, d.4alkylOR5, Co-4alkylNR5R6 and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A;
R5 and R6 are independently selected from the group consisting of hydrogen and d- δalkyl; wherein any d..6alkyl defined under R1, R2 and R4 may be substituted by one or more A ;
A is selected from the group consisting of hydrogen, hydroxy, halo, nitro, oxo, Co- 6alkylcyano, Co- alkylC3.6cycloalkyl, d.6alkyl, d.6alkylhalo, Od-βalkylhalo, C2.
6alkenyl, C0.3 alkylaryl, C0.6alkylOR5, OC2.6alkylOR5, d.6alkylSR5, OC^alkylSR5,
(CO)R5, O(CO)R5, OC2.6alkylcyano, Od-6alkylCO2R5, O(CO)OR5, Od.6alkyl(CO)R5, d.6alkyl(CO)R5, NR5OR6, OC2.6alkylNR5R6, C0.6alkyl(CO)NR5R6, Od-
6alkyl(CO)NR5R6, OC2.6alkylNR5(CO)R6, C0.6alkylNR5(CO)R6, C0. 6alkylNR5(CO)NR5R6, O(CO)NR5R6, C0.6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6, C0.
6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, SO3R5, d-6alkylNR5(SO2)NR5R6, OC2-
6alkyl(SO2)R5, C0.6alkyl(SO2)R5, C0.6alkyl(SO)R5,
OC2.6alkyl(SO)R5 and a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; ml is selected from 0, 1, 2, 3 and 4; m2 is selected from 0, 1, 2 and 3; n is selected from 0, 1 and 2; and t is O or 1, or a pharmaceutically acceptable salt or an optical isomer thereof, with the proviso that the compound is not 5-(4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl-
[1,2,4] oxadiazole, 1 ,2-di {2-(3 -amino-phenyl)- [1,3,4] oxadiazole-yl)ethane, l,2-di{5-[5-
(4-nitro-phenyl)furan-2-yl]-[l,3,4]oxadiazol-yl)ethane, l,2-di{5-[5-(4-bromo- phenyl)furan-2-yl]-[l ,3,4]oxadiazol-yl)ethane, 1 ,2-di{5-[5-(4-chloro-phenyl)furan-2-yl]-
[1 ,3,4]oxadiazol-yl)ethane and 1 ,2-di{5-[5-(2,4-dibromo-phenyl)furan-2-yl]- [l,3,4]oxadiazol-yl)ethane; for the manufacture of a medicament for the inhibition of transient lower esophageal sphincter relaxations (TLESRs).
3. Use of a compound of formula la as defined in claim 1, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of gastro-esophageal reflux disease (GERD).
4. Use of a compound of formula la as defined in claim 1 , or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the prevention of reflux.
5. Use of a compound of formula la as defined in claim 1, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, regurgitation.
6. Use of a compound of formula la as defined in claim 1 , or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, asthma.
7. Use according to claim 6, wherein the asthma is reflux-related asthma.
8. Use of a compound of formula la as defined in claim 1 , or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, laryngitis.
9. Use of a compound of formula la as defined in claim 1, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, lung disease.
10. Use of a compound of formula la as defined in claim 1, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for managing failure to thrive.
11. Use of a compound of formula I as defined in claim 2, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of gastro-esophageal reflux disease (GERD).
12. Use of a compound of formula I as defined in claim 2, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the prevention of reflux.
13. Use of a compound of formula I as defined in claim 2, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, regurgitation.
14. Use of a compound of formula I as defined in claim 2, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, asthma.
15. Use according to claim 14, wherein the asthma is reflux-related asthma.
16. Use of a compound of formula I as defined in claim 2, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, laryngitis.
17. Use of a compound of formula I as defined in claim 2, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for the treatment of, or prevention of, lung disease.
18. Use of a compound of formula I as defined in claim 2, or a pharmaceutically acceptable salt or an optical isomer thereof, for the manufacture of a medicament for managing failure to thrive.
19. Use according to any one of the preceding claims, wherein the compound is selected from the group of compounds consisting of
2- [5 -(3 -Methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole,
5-(3-Methoxy-phenyl)-3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
3-[5-(l-Methyl-5-thiophen-2-yl-lH-imidazol-2-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- benzonitrile,
3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]traiazol-3-ylsulfanylmethyl)-5-phenyl-
[1,2,4] oxadiazole,
2- [5 -(3 -Methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5 -methyl- 1 H- benzoimidazole, 3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-trifluoromethyl- phenyl)-[l,2,4]oxadiazole,
3-(3-Methoxy-phenyl)-5-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-phenyl-
[1,2,4] oxadiazole,
5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-m-tolyl-
[1,2,4] oxadiazole, 3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl] -benzonitrile,
3-[4-Methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[1,2,4] oxadiazole,
3-[5-(2-Methyl-thiazol-4-yl)-[l,3,4]oxadiazol-2-ylsulfanylmethyl]-5-m-tolyl- [1,2,4] oxadiazole,
3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thioρhen-2-yl-
[l,2,4]oxadiazole,
3-[5-(2,4-Dimethyl-thiazol-5-yl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m- tolyl-[l,2,4]oxadiazole,
3-[4-Methyl-5-(5-nitro-furan-2-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[l,2,4]oxadiazole,
4-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine, 3-[5-(4-tert-Butyl-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[l,2,4]-oxadiazole,
2-Chloro-5-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-
[ 1 ,2,4]triazol-3-yl] -pyridine,
2- [5 -(3 -Methoxy-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -benzooxazole, 3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole,
3-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
5-(3-Fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole,
2-(5 -m-Tolyl- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl)-pyridine,
2- [5-(3 -Methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-imidazo [4,5- bjpyridine,
5-(3-Fluoro-5-methyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l ,2,4]oxadiazole,
3-Methyl-5-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine,
3-(4-Methyl-5-phenyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
2-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-Benzyl-2-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-
[ 1 ,2,4]triazol-3 -yl] -morpholine,
4-[4-Methyl-5-(5-thiophen-3-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-
3-yl]-pyridine, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiazol-4-yl- [1,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-nitro-phenyl)-
[1,2,4] oxadiazole,
2-Methyl-4-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazol-5 -yl] -pyridine,
3-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-(4-Methyl-5-thioρhene-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole, 3-(4-Methyl-5-thiazol-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[l,2,4]oxadiazole,
5-(3-Iodo-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(3-Ethyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
2- [5 -(2-Methyl-pyridin-4-yl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole,
2-[5-(3-Iodo-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-lH-benzoimidazole,
3-(4-Methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole, 2,6-Dichloro-4-[4-methyl-5-(5-m-tolyl-[ 1 ,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-
[1 ,2,4]triazol-3-yl]-pyridine,
3-(4-Methyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
Dimethyl-{3-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]phenyl}-amine, 5-(3-Chloro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3- trifluoromethoxy-phenyl)[l,2,4]oxadiazole,
3-(5-Cyclohexyl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- [l,2,4]oxadiazole,
3-(5-tert-Butyl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
5-(3-Bromo-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 2- [5 -(3 -Bromo-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole, "5-(3-Methoxymethyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- lsulfanylmethyl)-[l,2,4]oxadiazole,
2- [5 -(3 -Methoxymethyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H- benzoimidazole, 4-[5-(4-Methyl-5-thioρhen-2-yl-4Η-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
3 -yl] -pyridine,
2-{l-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-l-methyl-lH- imidazo[4,5-b]pyridine,
2- [5 -(3-Methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 -methyl- 1 H- imidazo[4,5-b],
3-[l-Methyl-l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-5-m- tolyl-[l ,2,4] oxadiazole,
3-[ 1 -(4-Methyl-5-thiophen-2-yl-4H-[l ,2,4]triazol-3-ylsulfanyl)-ethyl]-5-m-tolyl-
[l,2,4]oxadiazole, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfonylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfmylmethyl)-5-m-tolyl-
[l,2,4]oxadiazole, or
5-(3-Furan-3-yl-ρhenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-(4-Cyclopropyl-5-{l-[5-(2,5-difluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-
4Η-[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[l,2,4]triazol-3-yl)-pyridine, 4-{4-Methyl-5-[l-(5-m-tolyl-[l,2,4]oxadiazol-3-yl)-ethylsulfanyl]-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-o-tolyl-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-cyclopropyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
2- { 3 - [5 -(2-Fluoro-5 -methyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5 -thiophen-2- yl-[l,2,4]triazol-4-yl}-ethanol,
4- {4-Ethyl-5- [5-(2-fluoro-5-methyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4H-
[1 ,2,4]triazol-3-yl}-pyrimidine, 3-(4-Ethyl-5-furan-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- , , , . phenyl)- [ 1,2,4] oxadiazole,
{3-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thioρhen-2-yl-
[l,2,4]triazol-4-yl} -acetic acid methyl ester,
5-(2-Fluoro-5-methyl-phenyl)-3-[5-furan-2-yl-4-(2-methoxy-ethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
3-(4-Cycloρropyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5- methyl-phenyl)- [ 1 ,2,4] oxadiazole,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-cyclopropylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-
3-ylsulfanylmethyl)-[ 1 ,2,4] oxadiazole, 4-{5-[3-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyrimidine,
3-(5-Cyclopentyl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[l,2,4]oxadiazole,
3-(3-Chloro-phenyl)-5-{4-ethyl-5-[2-(4-methoxy-phenyl)-ethyl]-4H-[l,2,4]triazol-3- ylsulfanylmethyl } - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-p-tolyloxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(2-methoxy-ethyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole, 3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,,
5-(5-Chloro-2-fluoro-ρhenyl)-3-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole,
3 -(3 -Chloro-phenyl)-5-(4-ethyl-5-methoxymethyl-4H- [ 1 ,2,4]triazol-3 -ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-(5-{l-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-3- yl)-pyridine, 3-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
3-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[l,2,4]oxadiazole,
5-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-furan-2-yl- [1 ,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, {5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-
3 -yl} -methanol,
3-(3-Chloro-phenyl)-5-[4-ethyl-5-(2-methoxy-ethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-methylsulfanylmethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1 ,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(5-ethoxymethyl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazole-
3 -carboxylic acid methyl ester, 2-(5-Chloro-2-fluoro-ρhenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,3 ,4] oxadiazole,
2-(3-Chloro-phenyl)-5-(4-cyclopropyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,3 ,4] oxadiazole,
5-(3-Chloro-phenyl)-3-{l-[4-ethyl-5-(tetrahydro-furan-2-yl)-4H-[l,2,4]triazol-3- ylsulfanyl]-ethyl}-[l ,2,4]oxadiazole,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-pyridazine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-ylmethyl)-pyridine, 5-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-ρyridin-2-ol,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-phenol,
5-(3-Chloro-phenyl)-3-[5-(4-methoxy-phenoxymethyl)-4-(tetrahydro-furan-2-ylmethyl)- 4H-[1 ,2,4]triazol-3-ylsulfanylmethyl]-[l ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-cyclopropyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-
3 -ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole, 3-(4-Ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- ,
[l,2,4]oxadiazole,
3-[4-Ethyl-5-(tetrahydro-furan-2-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[1,2,4] oxadiazole,
2-(3-Chloro-phenyl)-5-{l-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanyl]- ethyl}-[l,3,4]oxadiazole,
4-{5-[3-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyrimidine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyrimidine, 3-(3-Chloro-phenyl)-5-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(3-Methylsulfanyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
2-[5-(3-Methylsulfanyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H- benzoimidazole,
5-(2,5-Dimethyl-ρhenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(2-Fluoro-5-methyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 5-(3-Cyclopropyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[ 1 ,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-{5-[2-(3-Chloro-phenyl)-oxazol-4-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3-yl}- pyridine,
4-[4-Methyl-5-(5-thioρhen-2-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol- 3 -yl] -pyridine,
4-{4-Methyl-5-[5-(3-methylsulfanyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[1 ,2,4]triazol-3-yl}-pyridine,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 2-Methyl-4-[3-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine, l-{3.[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-phenyl}-ethanone,
4- { 5- [5 -(2-Fluoro-5-methyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H- [l,2,4]triazol-3-yl}-pyridine, ''2-Methyi-4-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-
[ 1 ,2,4] triazol-3 -yl] -pyridine,
3 - [5 -(3 -Chloro-phenyl)-isoxazol-3 -ylmethylsulfanyl] -4-methyl-5 -thiophen-2-yl-4H-
[l,2,4]triazole, 5 4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
3-(4-Butyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methoxy-propyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- l o ylsulfanylmethyl] -[1,2,4] oxadiazole,
3-(4-Benzyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, is 3-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
5-(3-Chloro-phenyl)-3-(4-methyl-5-thioρhen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4- { 5 - [5-(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H- 20 [l,2,4]triazol-3-yl}-2-methyl-pyridine,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 25 3-{5-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
5-(3-Chloro-phenyl)-3-(5-thiophen-2-yl-4-thioρhen-2-ylmethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- 30 [1,2,4] oxadiazole,
3-{5-[3-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
4- { 5-[3-(2-Fluoro-5-methyl-phenyl)-[ 1 ,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine, 35 4-{5-[5-(5 -Bromo-2-fluoro-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H- , . ,
[ 1 ,2,4]triazol-3 -yl } -pyridine,
3-{5-[5-(5-Bromo-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
5-(5-Bromo-2-fluoro-phenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l ,2,4]oxadiazole,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-phenyl-
[l,2,4]oxadiazole,
3-{5-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4] triazol-3 -yl } -pyridine, 4-{5-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
5-(3-Fluoro-phenyl)-3-(4-methyl-5-thioρhen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
3-[4-Methyl-5-(5-thiophen-3-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol- 3-yl]-pyridine,
3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thioρhen-3-yl-
[1,2,4] oxadiazole,
2-Chloro-4-[3-(4-methyl-5-pyridin-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5 -yl] -pyridine, 2-Chloro-4-[3-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5 -yl] -pyridine,
2-Chloro-4-[3-(4-methyl-5-thioρhen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazol-5 -yl] -pyridine,
4-[4-Methyl-5-(5-phenyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-phenyl-
[1,2,4] oxadiazole,
5-(5-Bromo-2-fluoro-phenyl)-3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole, 3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-thiophen-2-yl-4H-
[l,2,4]triazole,
2-Chloro-4-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5 -yl] -pyridine,
4-{5-[3-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H- [l,2,4]triazol-3-yl}-pyridine, '-(3-FΪuoro-ρhenyl)-5-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole, 3-(4-Ethyl-5-thiophen-2-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l ,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-furan-2-ylmethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- [ 1 ,2,4]triazol-3-yl} -pyridine,
3-{5-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[1 ,2,4]triazol-3-yl} -pyridine,
5-(3-Chloro-ρhenyl)-3-(4-ethyl-5-thioρhen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 3-{5-[5-(3 -Chloro-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-furan-2-ylmethyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
3-(4-Furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
5-(5-Fluoro-2-methyl-phenyl)-3-(4-furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol- 3-ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-furan-2-ylmethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-[3-(4-Methyl-5-pyridin-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -benzonitrile, 3-[3-(4-Methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -benzonitrile,
3-[3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -benzonitrile,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l ,2,4] oxadiazole,
2-Chloro-4-[3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5 -yl] -pyridine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole, 3-(4-Ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- [l,2,4]oxadiazole,
4-[4-Ethyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-[4-Ethyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-(4-Ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l ,2,4] oxadiazole,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine, 3-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[l,2,4]triazol-3-yl}-pyridine,
3 - [5-(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5 -pyridin-4-y 1-
[ 1 ,2,4]triazol-4-ylamine,
4-{5-[5-(5-Bromo-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl} -pyridine,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-2-yl-
[1,2,4] oxadiazole,
3-[3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -benzonitrile, 3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-phenyl-
[1,2,4] oxadiazole,
4-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -2-methoxy-pyridine,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
2-Methyl-4-[3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazol-5 -yl] -pyridine, 4-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -2-methyl-pyridine,
5-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thioρhen-2-yl-
[1,2,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-pyridine, 4-[3-(4-Ethyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -2-methyl-pyridine,
3-{5-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-benzonitrile, 5-(3-Chloro-phenyl)-3-[5-(3-chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[5-(4-chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
4- { 5- [5-(2,5-Dichloro-phenyl)-[ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-ethyl-4H- [l,2,4]triazol-3-yl} -pyridine,
5-(2,5-Dichloro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(2,5-Difluoro-ρhenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- y lsulfanylmethyl)- [ 1 ,2,4] oxadiazole, 4-{5-[5-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
5-(2,5-Dichloro-phenyl)-3-(4-ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-propyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4- { 5 - [5 -(2-Fluoro-5 -methyl-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-propyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[1,2,4] oxadiazole,
4-[4-Methyl-5-(3-thiophen-3-yl-[l,2,4]oxadiazol-5-ylmethylsulfanyl)-4H-[l,2,4]triazol- 3 -yl] -pyridine,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thioρhen-3-yl-
[1,2,4] oxadiazole,
5-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl-
[1,2,4] oxadiazole, 5-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l ,2,4]triazol-3-ylsulfanylmethyl)-[l ,2,4]oxadiazol-5- yl] -thiophene-3 -carbonitrile,
5-(3-Chloro-phenyl)-3-[5-(2-fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(3-fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(4-fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
3-(5-Benzo[b]thiophen-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro- phenyl)- [ 1 ,2,4] oxadiazole, 5-(3-Chloro-ρhenyl)-3-[5-(3-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(3-Chloro-ρhenyl)-3-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l,2,4]oxadiazole,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)- [ 1 ,2,4] oxadiazole, 3-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-pyridin-4-yl-
[ 1 ,2,4]triazol-4-ylamine,
3 - [5-(2-Fluoro-5 -methyl-phenyl)- [ 1,2,4] oxadiazol-3 -ylmethylsulfanyl] -5 -thiophen-2-yl-
[ 1 ,2,4]triazol-4-ylamine,
3-Pyridin-4-yl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-[l,2,4]triazol-4- ylamine,
3-Thiophen-2-yl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-[l,2,4]triazol-4- ylamine,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole, 5-(3-Chloro-ρhenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-
2-methyl-pyridine,
5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4] oxadiazole, 4-[4-Ethyl-5-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-Ethyl-3-furan-2-yl-5-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazole,
5-(3-Chloro-phenyl)-3-[5-(3,5-dichloro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-m-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole, 5-(3-Chloro-ρhenyl)-3-[4-ethyl-5-(3-nitro-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazole,
4-{5-[3-(3-Chloro-ρhenyl)-isoxazol-5-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(3-Chloro-phenyl)-3-[5-(2,5-difluoro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(3-chloro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(4-chloro-ρhenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole, 4-{5-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
3 - [5-(3 -Chloro-phenyl)-oxazol-2-ylmethylsulfanyl] -4-ethyl-5 -thiophen-2-yl-4H-
[l,2,4]triazole,
3-[5-(3-Chloro-phenyl)-oxazol-2-ylme ylsulfanyl]-4-ethyl-5-furan-2-yl-4H- [l,2,4]triazole,
5-(2-Chloro-5-methyl-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
4-{5-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine, 3-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-ethyl-5-thiophen-2-yl-4H-
[l,2,4]triazole,
3 - [3 -(3 -Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl] -4-ethyl-5 -furan-2-yl-4H-
[l,2,4]triazole,
4-{5-[5-(2-Fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H- [l,2,4]triazol-3-yl}-pyridine, 5-(2,5-Dichloro-thioρhen-3-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-{5-[5-(2,5-Dichloro-thiophen-3-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
4-Ethyl-3-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-
4H-[l,2,4]triazole,
4-Ethyl-3-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-5-furan-2-yl-4H- [l,2,4]triazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole,
5 -(4-Ethyl-5 -trifluoromethyl-4H- [ 1 ,2,4] triazol-3 -ylsulfanylmethyl)-3 -thiophen-3 -yl-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-fluoro-phenyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-fluoro-phenyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[l,2,4]oxadiazole, 3-{3-[5-(3-Chloro-thiophen-2-yl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,2,4]oxadiazol-5-yl}-benzonitrile,
4-{5-[5-(3-Chloro-ρhenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
2-(3-Chloro-phenyl)-5-(4-e l-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,3 ,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(2-fluoro-5-methyl-phenyl)-4-furan-2-ylmethyl-4H-
[ 1 ,2,4]triazol-3 -ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 4-[3-(4-Ethyl-5-trifluoromethyl-4H-[l ,2,4]triazol-3-ylsulfanylmethyl)-[l ,2,4]oxadiazol- 5 -yl] -2-methyl-pyridine,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-methoxy- phenyl)- [ 1 ,2,4] oxadiazole,
5-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-(3-methoxy- phenyl)-[l,2,4]oxadiazole,
5-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-2-yl-
[l,2,4]oxadiazole,
5-(5-Chloro-2-fluoro-ρhenyl)-3-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole, 3-[3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -benzonitrile,
3 - [5-(3 -Chloro-phenyl)-isoxazol-3 -ylmethylsulfanyl] -4-ethyl-5 -trifluoromethyl-4H-
[l,2,4]triazole,
3-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-5-trifluoromethyl-4H- [l,2,4]triazole,
4-Ethyl-3-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-5-trifluoromethyl-4H-
[l,2,4]triazole,
4-{3-[5-(3-Fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[ 1 ,2,4] oxadiazol-5 -yl } -2-methyl-pyridine, 4-{3-[5-(3-Chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,2,4]oxadiazol-5-yl}-2-methyl-pyridine,
4-{3-[5-(4-Chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[ 1 ,2,4] oxadiazol-5 -yl } -2-methyl-pyridine,
4-{3-[5-(4-Methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]- [1 ,2,4]oxadiazol-5-yl}-2-methyl-pyridine,
4-[3-(4-Ethyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2- methyl-pyridine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-fluoro-phenyl)-
[1,2,4] oxadiazole, 4-{4-Ethyl-5-[5-(3-fluoro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
5-(3-Chloro-phenyl)-3-[5-(3,5-difluoro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[5-(2,6-difluoro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[ 1 ,2,4] oxadiazole, 2-[3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-methyl-phenol,
3-{l-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole, 4-(5-{l-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridine,
3-[5-(4-Butoxy-ρhenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(3-chloro- phenyl)- [ 1 ,2,4] oxadiazole,
3-(5-Benzo[l,3]dioxol-5-yl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro- phenyl)- [1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-methyl-thiazol-4- yl)- [ 1 ,2,4] oxadiazole,
3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-fluoro-phenyl)-
[1,2,4] oxadiazole, 4-Ethyl-3-{l-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-5-furan-2-yl-
4H-[l,2,4]triazole,
4-(4-Ethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methyl-3H-imidazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(l-methyl-lH-imidazol-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(l-methyl-lH-imidazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 4-{5-[5-(3 -Chloro-pheny l)-4-methyl-isoxazol-3 -ylmethylsulfanyl] -4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
3 - [5 -(3 -Chloro-pheny l)-4-methy l-isoxazol-3 -ylmethylsulfanyl] -4-ethyl-5 -furan-2-yl-4H-
[l,2,4]triazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-methyl-thioρhen- 2-yl)-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methyl-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(5-methyl-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 4-{5-[4-Chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-pyridine,
3-[4-Chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
2-Chloro-4-{5-[5-(3-chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-6-methyl-pyridine,
3-[5-(5-Bromo-furan-2-yl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(3-chloro- phenyl)-[l ,2,4] oxadiazole,
2-Chloro-4-{5-[5-(3-chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl} -pyridine, 2-Chloro-4-{5-[5-(3-chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-6-methoxy-pyridine,
2-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-methyl-benzonitrile,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methoxy-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1 ,2,4]oxadiazole,
3-[5-(5-Chloro-thiophen-3-yl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-
5 -fluoro-benzonitrile, 4-Ethyl-3-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-5-thiophen-2-yl-4H-[l,2,4]triazole,
4-Methyl-3-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-5-thiophen-3-yl-4H-[l,2,4]triazole,
4-Ethyl-3-furan-2-yl-5-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazole,
4-[4-Ethyl-5-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]-pyridine,
4- [4-Methyl-5-(5-phenyl-isoxazol-3 -ylmethylsulfanyl)-4H- [ 1 ,2,4]triazol-3 -yl] -pyridine, 2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,3, 4] oxadiazole,
4-[4-Methyl-5-(5-m-tolyl-[l,3,4]oxadiazol-2-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-[4-Ethyl-5-(5-m-tolyl-[l,3,4]oxadiazol-2-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-{5-[5-(5-Chloro-thiophen-3-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[1 ,2,4]triazol-3-yl}-pyridine,
3-[3-(4-Ethyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-fluoro-benzonitrile, 3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- 4-fluoro-benzonitrile,
3-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-fluoro-benzonitrile,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
3-[5-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- benzonitrile,
3-[3-(4-Methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl] -benzonitrile, 5-(5-Chloro-2-fluoro-phenyl)-3-(4-methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
2-Chloro-4-[3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine,
2-Chloro-4-[3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazol-5-yl]-pyridine,
2-(3-Chloro-phenyl)-5-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,3 ,4] oxadiazole,
2-(3-Chloro-ρhenyl)-5-(4-methyl-5-thiazol-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,3,4]oxadiazole, 2-(3-Chloro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,3,4]oxadiazole,
2-(3-Chloro-phenyl)-5-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,3, 4] oxadiazole,
4-{4-Ethyl-5-[5-(4-methyl-thiophen-2-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H- [1 ,2,4]triazol-3 -yl } -pyridine,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-methyl-thioρhen-2- yl)-[l ,2,4]oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole, 4- { 5- [3-(3-Chloro-phenyl)-[ 1 ,2,4] oxadiazol-5-ylmethylsulfanyl] -4-ethyl-4H-
[1 ,2,4]triazol-3-yl}-pyridine,
4-{4-Ethyl-5-[5-(3-nitro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4H-[l,2,4]triazol-
3-yl}-pyridine,
2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-nitro-phenyl)- [1,3, 4] oxadiazole, 4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H-[l,2,4]triazol-
3-yl} -pyridine,
3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-(4-methoxy-phenyl)-4H-
[l,2,4]triazole, 5-(3-Chloro-phenyl)-3-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)- ethyl]-[l ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[l-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[1,2,4] oxadiazole,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
3-[5-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -benzonitrile, 3-[5-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2-yl]- benzonitrile,
3-[5-(4-Methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -benzonitrile,
3-[5-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,3,4] oxadiazol-2-yl] -benzonitrile,
4-{5-[5-(3-Chloro-ρhenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
4- { 5 - [5-(3 -Chloro-phenyl)- [ 1 ,3 ,4] oxadiazol-2-ylmethylsulfanyl] -4-cyclopropyl-4H-
[1 ,2,4] triazol-3 -yl} -pyridine, 4- { 5- [5-(5-Chloro-2-fluoro-phenyl)-[ 1 ,3 ,4] oxadiazol-2-ylmethylsulfanyl] -4-cyclopropyl-
4H-[l,2,4]triazol-3-yl}-pyridine,
2-(5-Chloro-2-fluoro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,3,4]oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-methyl-4H- [ 1 ,2,4]triazol-3-yl} -pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
2-(3-Chloro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3- y lsulfanylmethyl] - [ 1 ,3 ,4] oxadiazole, 2-(3-Chloro-phenyl)-5-[l-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]- [l,3,4]oxadiazole,
5-(5-Chloro-2-fluoro-ρhenyl)-3-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanyl)-ethyl]-[l,2,4]oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl- 4H-[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
2-Chloro-4-[3-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine, 4-{5-[5-(2-Fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
4-{4-Cyclopropyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]- 4H-[l,2,4]triazol-3-yl}-pyridine,
2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l ,3, 4] oxadiazole,
2-[4-Ethyl-5-(4-methoxy-ρhenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(2-fluoro-5- methyl-phenyl)- [ 1 ,3 ,4] oxadiazole, 4-{5-[5-(5 -Chloro-2-fluoro-phenyl)-isoxazol-3 -ylmethylsulfanyl] -4-ethyl-4H-
[ 1 ,2,4] triazol-3 -yl } -pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-{5-[5-(5 -Chloro-2-fluoro-phenyl)-isoxazol-3 -ylmethylsulfanyl] -4-methy 1-4H- [l,2,4]triazol-3-yl} -pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
3-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
3-{l-[5-(5 -Chloro-2-fluoro-phenyl)-isoxazol-3 -yl] -ethylsulfanyl } -4-ethyl-5 -furan-2-yl- 4H-[l,2,4]triazole, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-(5-{l-[5-(3-Chloro-ρhenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-pyridine, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-cycloρropyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
5-(5-Chloro-2-fluoro-phenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-(5-furan-3-yl-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4]oxadiazole,
4-Chloro-2-[3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1 ,2,4]oxadiazol-5-yl]-phenol,
2-Chloro-4-[5-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,3,4]oxadiazol-2-yl]-pyridine, 2-Chloro-4-[5-(4-ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -pyridine,
2-Chloro-4-[5-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -pyridine,
2-Chloro-4-[5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,3,4]oxadiazol-2-yl]-pyridine,
2-Chloro-4-{5-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[ 1 ,3 ,4] oxadiazol-2-yl} -pyridine,
2-(3-Chloro-ρhenyl)-5-{ l-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanyl] -ethyl }-[ 1 ,3 ,4] oxadiazole, 4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-
4H-[ 1 ,2,4]triazol-3-yl)-pyridine,
5-(5-Bromo-2-fluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
2-(3-Chloro-ρhenyl)-5-[5-(4-methoxy-ρhenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,3,4]oxadiazole,
4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4-{5-[5-(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-cyclopropyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-(5-{l- [5 -(2-Fluoro-5 -methyl-phenyl)- [ 1,3,4] oxadiazol-2-yl] -ethylsulfanyl } -4-methyl- 4H-[1 ,2,4]triazol-3-yl)-pyridine,
4-(4-Ethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-yl]- ethylsulfanyl}-4H-[l,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropylmethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-yl]- ethylsulfanyl}-4H-[l,2,4]triazol-3-yl)-pyridme,
2-(2-Fluoro-5-methyl-ρhenyl)-5-{l-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-
[ 1 ,2,4]triazol-3 -ylsulfany 1] -ethyl } - [ 1 ,3 ,4] oxadiazole, 4-(5-{ 1 -[5-(5-Chloro-2-fluoro-phenyl)-[l ,3 ,4] oxadiazol-2-yl] -ethylsulfanyl }-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4- cyclopropyl-4H-[l,2,4]triazol-3-yl)-pyridine,
2-(5-Chloro-2-fluoro-phenyl)-5-[l-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)- ethyl]-[l,3,4]oxadiazole,
2-(5-Chloro-2-fluoro-phenyl)-5-{l-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-
[ 1 ,2,4]triazol-3 -ylsulfany 1] -ethyl } - [ 1 ,3 ,4] oxadiazole,
4-(4-Cyclopropylmethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]- ethylsulfanyl } -4H- [ 1 ,2,4] triazol-3 -yl)-pyridine, 4-(5-{l-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[l,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropyl-5-{l-[5-(3-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-(5-{l-[5-(4-Methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}- [l,3,4]oxadiazol-2-yl)-2-methyl-pyridine,
4-(5-{l-[4-Ethyl-5-(4-methoxy-ρhenyl)-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-
[ 1 ,3 ,4] oxadiazol-2-yl)-2-methyl-pyridine,
4-{5-[l-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,3,4]oxadiazol-2- yl } -2-methyl-pyridine, 4- { 5- [ 1 -(4-Cyclopropyl-5-pyridin-4-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanyl)-ethyl] -
[l,3,4]oxadiazol-2-yl}-2-methyl-pyridine,
4-{5-[l-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,3,4]oxadiazol-2- yl } -2-methyl-pyridine,
2-(3-Chloro-phenyl)-5-{l-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanyl] -ethyl} - [ 1 ,3 ,4] oxadiazole, 3-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-
[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-
[l,2,4]triazol-3-yl)-2-methyl-pyridine, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
5-(3-Chloro-phenyl)-3-{ 1 -[5-(4-methoxy-phenyl)-4-methyl-4H-[l ,2,4]triazol-3- ylsulfanyl]-ethyl}-[l,2,4]oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4- cyclopropyl-4H-[l,2,4]triazol-3-yl)-pyridine,
5-(5-Chloro-2-fluoro-phenyl)-3-{l-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfany 1] -ethyl } - [ 1 ,2,4] oxadiazole,
4-[5-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -2-methyl-pyridine, 4- [5 -(4-Cyclopropyl-5 -pyridin-4-yl-4H- [ 1 ,2,4] triazol-3 -ylsulfany lmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -2-methyl-pyridine,
4- { 5 - [5-(5-Chloro-2-fluoro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-cyclopropyl-
4H- [ 1 ,2,4]triazol-3 -yl} -pyridine,
4-[5-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -2-methyl-pyridine,
4-(5-{ 1 -[5-(3-Chloro-phenyl)-[l ,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4- cyclopropylmethyl-4H-[ 1 ,2,4] triazol-3 -yl)-pyridine,
4-(5-{l-[5-(4-Fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-
[l,3,4]oxadiazol-2-yl)-2-methyl-pyridine, 4-(5-{l-[5-(3-Fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-
[l,3,4]oxadiazol-2-yl)-2-methyl-pyridine,
3-[3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-4-fluoro-benzonitrile,
4-Chloro-2-[3-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4]oxadiazol-5-yl]-phenol,
4- {4-Cyclopropyl-5 - [5 -(3 -methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4H-
[l,2,4]triazol-3-yl}-pyridine,
4- {4-Cyclopropyl-5-[5-(2-fluoro-5-methyl-phenyl)-[ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -
4H-[1 ,2,4]triazol-3-yl}-pyridine, 4- { 4-Cyclopropyl-5 - [5 -(3 -fluoro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4H- [ 1 ,2,4]triazol-3-yl} -pyridine,
4-[4-Cyclopropyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3- yl] -pyridine,
3-[3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4]oxadiazol-5-yl]-benzonitrile,
4-{4-Cyclopropyl-5-[5-(2,5-difluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
4-{4-Cyclopropyl-5-[l-(5-m-tolyl-[l,2,4]oxadiazol-3-yl)-ethylsulfanyl]-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-(4-Cyclopropyl-5-{l-[5-(3-methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-{5-[5-(2-Chloro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-cyclopropyl-
4H-[ 1 ,2,4]triazol-3-yl} -pyridine,
2-[3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazol-5-yl]-4-methyl-phenol,
4-(5-{l-[5-(2-Chloro-5-methyl-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4- cyclopropyl-4H-[ 1 ,2,4]triazol-3-yl)-pyridine,
{3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -phenyl } -methanol, 3-[5-(4-Methyl-5-thiophen-2-yl-4H-[l ,2,4]triazol-3 -ylsulfanylmethyl)- [1 ,2,4]oxadiazol-
3 -yl] -phenol,
5-(3-Chloro-ρhenyl)-3-[4-(tetrahydro-furan-2-ylmethyl)-5-thiophen-2-yl-4H-
[ 1 ,2,4]triazol-3 -ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
(2-Chloro-phenyl)- { 5 - [5-(3 -chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4- isobutyl-4H-[ 1 ,2,4]triazol-3-yl} -methanol,
5-(2-Fluoro-5-methyl-phenyl)-3-[5-thiophen-2-yl-4-(2,2,2-trifluoro-ethyl)-4H-
[1 ,2,4]triazol-3-ylsulfanylmethyl]-[l ,2,4]oxadiazole,
3-(2,5-Difluoro-phenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole, 5-Furan-3-yl-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
3-(3-Chloro-phenyl)-5-(5-furan-3-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole, 5-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
5-(3-C oro-phenyl)-3-(5-furan-3-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5 4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyrimidine,
4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyrimidine,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- l o ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(5-Chloro-thiophen-2-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole, is 5-(5-Chloro-thiophen-2-yl)-3-(4-ethyl-5-furan-2-yl-4H-[ 1 ,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(5-Chloro-thiophen-3-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- 20 [ 1 ,2,4]triazol-3 -ylmethoxy } -phenol,
4-{5-[5-(5-Chloro-2-fluoro-ρhenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -ylmethoxy} -phenol,
3-(2,5-Difluoro-ρhenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5 3-(2,5-Difluoro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
4.(5_{l_[3.(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4- { 5 - [5 -(5 -Chloro-2-fluoro-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-cyclopropyl- 30 4H-[l,2,4]triazol-3-yl}-pyrimidine,
2-(5-{l-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-5-methoxy-pyrimidine,
2-(5-{ 1 -[5-(3-Chloro-ρhenyl)-[l ,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyrimidine, 35 4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H- [l,2,4]triazol-3-yl)-2-methoxy-pyridine,
5-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-2-methoxy-pyridine,
2-(5-{l-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H- [1 ,2,4]triazol-3-yl)-5-methoxy-pyridine,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-6-methoxy-pyridazine,
3-(5-{l-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine, 4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine,
5-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-isobutyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methylsulfanyl-propyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-hexyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-cyclopropylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4]oxadiazole, 5-(3-Chloro-phenyl)-3-[4-(3-fluoro-benzyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methyl-benzyl)-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(2-methyl-butyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methyl-butyl)-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[ 1 ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(2-fluoro-benzyl)-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole, 5-(3-Chloro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yloxymethyl)-
[1,2,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethoxy]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethoxy}-4-methyl-4H-[l,2,4]triazol- 3-yl)-pyridine, 4-(5-{l-[3-(3-Chloro-ρhenyl)-isoxazol-5-yl]-ethoxy}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
5-(2-Methoxy-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole, 5-Furan-2-yl-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl]-benzoic acid methyl ester,
5-(2-Fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4] oxadiazole,
5-(2,5-Difluoro-phenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-vinyl-phenyl)-
[l,2,4]oxadiazole, 5 -(3 -Difluoromethoxy-phenyl)-3 -(4-methyl-5 -thiophen-2-y 1-4H- [ 1 ,2,4] triazol-3 - ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(4-Methoxy-thiophen-3-yl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(2-Chloro-ρhenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole,
5-(4-Fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)- ethyl] - [ 1 ,2,4] oxadiazole, -(5-{l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethylsulfanyl}-4-methyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
3-(3-Chloro-phenyl)-5-[2-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylmethyl)- [ 1 ,2,4] oxadiazole,
2-(3-Chloro-phenyl)-5-[2-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[l,3,4]oxadiazole,
2-(3-Chloro-phenyl)-5-[2-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[l,3,4]oxadiazole, 2-(3-Chloro-phenyl)-5-[2-(4-cycloρropyl-5-furan-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]- [1,3, 4] oxadiazole,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-methyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl)-pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-methyl-propyl}-4-cyclopropyl-
4H-[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-propyl}-4-cyclopropyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro- [1 ,2,4]triazolo[4,3-a]pyridine,
8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-thiophen-2-yl-5,6,7,8-tetrahydro-
[l,2,4]triazolo[4,3-a]pyridine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8- tetrahydro-[ 1 ,2,4]triazolo[4,3-a]pyridine, 5-(5-Bromo-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl] -phenylamine,
5-(3-Chloro-phenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazole-3-sulfonylmethyl)- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfmylmethyl)-
[l,2,4]oxadiazole,
2-Methyl-6-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine, 4-(5-{l-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-ρyridin-2-ol,
4-(5-{2-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-propyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-methyl-(4-methyl-5-pyridin-4-yl-4H- [l,2,4]triazol-3-yl)-amine, 8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[l,2,4]triazolo[4,3-a]pyrimidine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8- tetrahydro-[ 1 ,2,4]triazolo[4,3-a]pyrimidine, 8-[5-(3-Chloro-ρhenyl)-[l,3,4]oxadiazol-2-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[ 1 ,2,4]triazolo[4,3-a]pyrimidine,
8-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethyl}-3-pyridin-4-yl-5,6,7,8- tetrahydro- [ 1 ,2,4] triazolo [4,3 -a]pyrimidine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-furan-2-yl-5,6,7,8- tetrahydro-[l,2,4]triazolo[4,3-a]pyrimidine,
8-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethyl}-3-pyridin-4-yl-5,6,7,8- tetrahydro-[ 1 ,2,4]triazolo[4,3-a]pyrimidine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(lH-pyrrol-3-yl)-
[1,2,4] oxadiazole, 4- { 5- [5 -(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H-
[l,2,4]triazol-3-yl} -pyridine 1 -oxide,
5-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-[4-(2-fluoro-ethyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(5-Chloro-thiophen-3-yl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-
4-hydroxy-benzonitrile, 3-(3-Chloro-phenyl)-5-[2-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[1,2,4] oxadiazole,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-proρyl}-[l,3,4]oxadiazol-2-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-4-cycloproρyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl)-pyridine, or
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l,l-dimethyl-ethyl}-
[ 1 ,3 ,4] oxadiazol-2-yl)-pyridine, 3-(5-{ 1 -[5-(3-Chloro-phenyl)-[l ,2,4] oxadiazol-3 -yl]-ethoxy}-4-cycloproρyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(2-Chloro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-
4H-[ 1 ,2,4]triazol-3-yl)-pyridine, 4-(5-{ l-[5-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-
4H-[l,2,4]triazol-3-yl)-pyridine,
4-(4-Cycloρropyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]- ethylsulfanyl}-4H-[l,2,4]triazol-3-yl)-pyridine,
3-{3-[l-(4-Methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,2,4]oxadiazol-
5-yl} -benzonitrile,
3-{3-[l-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[1,2,4] oxadiazol-5 -yl } -benzonitrile, 3-{l-[5-(3 -Chloro-phenyl)- [1,3,4] oxadiazol-2-yl] -ethylsulfanyl } -5 -pyridin-4-yl-
[ 1 ,2,4]triazol-4-ylamine,
3-(3-Chloro-phenyl)-5-[2-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[1,2,4] oxadiazole,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-4-cyclopropyl-4H- [l,2,4]triazol-3-yl)-pyridine, cis-4-(5 - {2- [3 -(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-5 -yl] -cyclopropyl } -4-cy clopropyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-(5- {2-[3-(3-Chloro-phenyl)-[ 1 ,2,4]oxadiazol-5-yl]- 1 , 1 -dimethyl-ethyl} -
[l,3,4]oxadiazol-2-yl)-pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-methyl-propyl}-[l,3,4]oxadiazol-
2-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-[l,3,4]oxadiazol-2- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-cycloproρyl}-[l,3,4]oxadiazol-2- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-4-methyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine, 4-(5-{2-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-propyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-[l,3,4]oxadiazol-2-yl)- pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-4-cycloproρyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
(S)-[l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H- [1 ,2,4]triazol-3-yl)-ethyl]-carbamic acid tert-butyl ester,
(S)- 1 - [3-(3-Chloro-phenyl)- [ 1 ,2,4] oxadiazol-5-yl] -2-(4-cyclopropyl-5-pyridin-4-yl-4H-
[l,2,4]triazol-3-yl)-ethylamine,
(S)-[l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H-
[l,2,4]triazol-3-yl)-ethyl]-dimethyl-amine, or a pharmaceutically acceptable salt or an optical isomer thereof.
20. A method for the inhibition of transient lower esophageal sphincter relaxations
(TLESRs), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la
Figure imgf000087_0001
(la) wherein: P is selected from the group consisting of hydrogen, d. alkyl or a 3- to 8-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; R1 is selected from the group consisting of hydrogen, hydroxy, halo, nitro, d-βalkylhalo, Od.6alkylhalo, d.6alkyl, Od-βalkyl, C2.6alkenyl, OC2.6alkenyl, C2.6alkynyl, OC2. 6alkynyl, Co-6alkylC3.6cycloalkyl, OCo-6alkylC3.6cycloalkyl, Co-6alkylaryl, OCo-βalkylaryl, CHO, (CO)RJ, O(CO)R5, O(CO)OR5, O(CN)OR5, d.6alkylOR5, OC2.6alkylOR5, C,.
6alkyl(CO)R5, Od-6alkyl(CO)R5, C0.6alkylCO2R5, Od.6alkylCO2R5, Co-ealkylcyano, OC2. ealkylcyano, Co-6alkylNR5R6, OC2.6alkylNR5R6, Cj.6alkyl(CO)NR5R6, Od-
6alkyl(CO)NR5R6, C0.6alkylNR5(CO)R6, OC2.6alkylNR5(CO)R6, Co-6alkylNR5(CO)NR5R6, C0-6alkylSR5, OC2.6alkylSR5, C0.6alkyl(SO)R5, OC2.6alkyl(SO)R5, C0.6alkylSO2R5, OC2.
6alkylSO2R5, C0.6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6,Co.6alkylNR5(SO2)R6, OC2.
6alkylNR5(SO2)R6, C0.6alkylNR5(SO2)NR5R6, OC2-6alkylNR5(SO2)NR5R6, (CO)NR5R6,
O(CO)NR5R6, NR5OR6, C0-6alkylNR5(CO)OR6, OC2.6alkylNR5(CO)OR6, SO3R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S, wherein said ring may be substituted by one or more A;
M1 is selected from the group consisting of a bond,
Figure imgf000088_0001
Co.
4alkyl(CO)Co-4alkyl, Co-3alkylOC0-3alkyl, C0-3alkyl(CO)NR5, C0-3alkyl(CO)NR5Co.3alkyl,
Co-4alkylNR5, Co-3alkylSC0.3alkyl, Co.3alkyl(SO)C0.3alkyl or C0-3alkyl(SO2)Co-3alkyl;
R2 is selected from the group consisting of hydrogen, hydroxy, Co-6alkylcyano, oxo, =NR5, =NOR5, d.4alkylhalo, halo, d-4alkyl, O(CO)d.4alkyl, C alkyl(SO)Co.4alkyl, d-
4alkyl(SO2)C0-4alkyl, (SO)C0.4alkyl, (SO2)C0.4alkyl, Od.4alkyl, d.4alkylOR5 and C0.
4alkylNR5R6;
X1, X2 and X3 are independently selected from the group consisting of CR, CO, N, NR, O and S; R is selected from the group consisting of hydrogen, Co-3alkyl, halo, Co-3alkylOR5, Co-
3alkylNR5R6, C0.3alkyl(CO)OR5, Co.3alkylNR5R6 and C0-3alkylaryl;
M2 is selected from a group consisting of a bond, CMalkyl, C3.7cycloalkyl, C2-3alkenyl,
C2.3alkynyl, C0.4alkyl(CO)C0.4alkyl, C0.3alkylOCo.3alkyl, Co-3alkylNR5d-3alkyl, C0.
3alkyl(CO)NR5, C0. alkylNR5, C0.3alkylSCo.3alkyl, C0-3alkyl(SO)C0-3alkyl and C0. 3alkyl(SO2)Co-3alkyl;
R ,3 ; is sel Ie_c„*te„dJ A from a group cons :i„s*t:ing o efι h„y,dΛrogen, h„ydAroxy, / C~>o-βa „ιlιk„y,ιlcyano, oxo, =NmR5
=NOR >53, d.4alkylhalo, halo, C1.4alkyl, O(CO)C alkyl, d.4alkyl(SO)Co.4alkyl, d
4alkyl(SO2)Co-4alkyl, (SO)C0. alkyl, (SO2)C0. alkyl, OCι.4alkyl, d.4alkylOR • 5D and C0.
4alkylNR5R6; X4 is selected from the group consisting of Co-4alkylR5, Co-4alkyl(NR5R6), Co-
4alkyl(NR5R6)=N, NR5C0.4alkyl(NR5R6)=N, NOC0.4alkyl, C alkylhalo, C, O, SO, SO2 and S;
Q is a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S, which group may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S and which fused ring may be substituted by one or more A;
R4 is selected from the group consisting of hydrogen, hydroxy, Co.6alkylcyano, oxo,
=NR5, =NOR5, C alkylhalo, halo, C alkyl, Od-4alkyl, OC0.6alkylaryl, O(CO)d.
4alkyl, C0.4alkyl(S)C0.4alkyl, d.4alkyl(SO)C0. alkyl, C1.4alkyl(SO2)C0. alkyl, (SO)C0. 4alkyl, (SO2)C0. alkyl, d.4alkylOR5, C0. alkylNR5R6 and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O or S, wherein said ring may be substituted by one or more A;
R5 and R6 are independently selected from the group consisting of hydrogen, hydroxy, d-
6alkyl, C0_6alkylC3.6cycloalkyl, Co-6alkylaryl, Co-6alkylheteroaryl and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O and S, and wherein R5 and R6 may together form a 5- or 6-membered ring containing one or more atoms independently selected from the goup consisting of C, N, O and S; wherein any d.6alkyl, C2.6alkenyl, C2.6alkynyl, Co-6alkylC3.6cycloalkyl, Co-βalkylaryl and
Co-βalkylheteroaryl defined under R1, R2, R3, R4, R5 and R6 may be substituted by one or more A;
A is selected from the group consisting of hydrogen, hydroxy, oxo, halo, nitro, Co-
6alkylcyano, C1.4alkyl, Co-4alkylC3-6cycloalkyl, d.6alkylhalo, Od-βalkylhalo, C2.
6alkenyl, Od-ealkyl, C0.3 alkylaryl, C0.6alkylOR5, OC2.6alkylOR5, d.6alkylSR5, OC2.
6alkylSR5, (CO)R5, O(CO)R5, OC2.6alkylcyano, C0.6alkylCO2R5, Od-6alkylCO2R5, O(CO)OR5, Od.6alkyl(CO)R5, d.6alkyl(CO)R5, NR5OR6, C0.6alkylNR5R6, OC2.
6alkylNR5R6, C0.6alkyl(CO)NR5R6, Od-6alkyl(CO)NR5R6, OC2.6alkylNR5(CO)R6, C0.
6alkylNR5(CO)R6,
C0.6alkylNR5(CO)NR5R6, O(CO)NR5R6, NR5(CO)OR6, Co.6alkyl(SO2)NR5R6,
OC2-6alkyl(SO2)NR5R6, C0.6alkylNR5(SO2)R6, OC2-6alkylNR5(SO2)R6, SO3R5, d.6alkylNR5(SO2)NR5R6, OC2.6alkyl(SO2)R5, C0.6alkyl(SO2)R5, C0.6alkyl(SO)R5,
OC2-6alkyl(SO)R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; m is selected from 0, 1, 2, 3 and 4; and n is selected from 0, 1, 2 and 3, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such inhibition.
21. A method for the inhibition of transient lower esophageal sphincter relaxations
(TLESRs), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula
Figure imgf000090_0001
(I) wherein:
P is selected from the group consisting of thiophene, pyridyl, thiazolyl, furyl, pyrrolyl and phenyl, whereby the phenyl ring is substituted on position 3 or disubstituted on positions
2 and 5;
R1 is attached to P via a carbon atom on ring P and is selected from the group consisting of hydrogen, hydroxy, halo, nitro, Ci-βalkylhalo, Od-δalkylhalo, d.6alkyl, Od-βalkyl, C2-
6alkenyl, Od-όalkenyl, d-βalkynyl, Od-βalkynyl, Co-6alkylC3.6cycloalkyl, OCo-6alkylC3. ecycloalkyl, C0.6alkylaryl, OC0.6alkylaryl, CHO, (CO)R5, O(CO)R5, O(CO)OR5,
O(CN)OR5, d.6alkylOR5, OC2.6alkylOR5, d.6alkyl(CO)R5, Od.6alkyl(CO)R5, C0.
6alkylCO2R5, OC1.6alkylCO R5, C0.6alkylcyano, OC2.6alkylcyano, C0-6alkylNR5R6, OC2-
6alkylNR5R6, d.6alkyl(CO)NR5R6, Od.6alkyl(CO)NR5R6, C0.6alkylNR5(CO)R6, OC2-
6alkylNR5(CO)R6, C0-6alkylNR5(CO)NR5R6, C0.6alkylSR5, OC2.6alkylSR5, Co.'
6alkyl(SO)R5, OC2.6alkyl(SO)R5, C0-6alkylSO2R5, OC2-6alkylSO2R5, Co-6alkyl(SO2)NR5R6,
OC2.6alkyl(SO2)NR5R6,Co-6alkylNR5(Sθ2)R6, OC2.6alkylNR5(Sθ2)R6, Co-
6alkylNR5(SO2)NR5R6, OC2-6alkylNR5(SO2)NR5R6, (CO)NR5R6, O(CO)NR5R6, NR5OR6,
C0.6alkylNR5(CO)OR6, OC2-6alkylNR5(CO)OR6, SO3R5 and a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S;
M1 is a bond;
X1 selected from the group consisting of C, CO, N, O and S;
X2 is selected from the group consisting of C, N, O and S;
X3 is i) selected from the group consisting of N, O and S, or ii) selected from N, O, S, and C when X2 is selected from N, O, or S, and when X3 is C the substituent R on X3 is H. ;
R is selected from the group consisting of hydrogen, Co-3alkyl, halo, Co^alkylOR5, Co-
3alkylNR5R6, C0.3alkyl(CO)OR5 and C0-3alkylaryl;
M2 is selected from a group consisting of a bond, C1.3a.kyl, C2.3alkynyl, Co-4alkyl(CO)Co- 4alkyl, C^alkylOQwalkyl, C0-3alkylNR5Cι.3alkyl, C0.3alkyl(CO)NR5, C0.4alkylNR5, C0.
3alkyl(SO)Co-3alkyl and C0.3alkyl(SO2)Co.3alkyl;
R3 is selected from a group consisting of hydroxy, Co-6alkylcyano, oxo, =NR5, =NOR5,
CMalkylhalo, halo, CMalkyl, O(CO)CMalkyl, CMalkyl(SO)C0.4alkyl, CMalkyl(SO2)Co- 4alkyl, (SO)C0.4alkyl, (SO2)C0-4alkyl, Od.4alkyl, d.4alkylOR5 and Co.4alkylNR5R6;
X4 is selected from the group consisting of Co-4alkylR5R6 , C3.7cycloalkyl, d.
4alkyl(NR5R6), NR5, Co. alkyl(NR5R6)=N, NR5C0.4alkyl(NR5R6)=N, NOC0-4alkyl, d.
4alkylhalo, O, SO, SO2 and S, and wherein the bond between M2 and X4 is a single bond ;
Q is i) selected from the group consisting of triazolyl, imidazolyl, oxadiazolyl, imidazolonyl, oxazolonyl, thiazolonyl, tetrazolyl and thiadiazolyl, and wherein any substitutable nitrogen atom in the ring is substituted with R4 on such nitrogen atom and any suitable carbon atom is optionally substituted with R4; and
R4 is selected from the group consisting of Co-6alkylcyano, =NC1.4alkyl, =NOR5, d- 4alkylhalo, halo, Ci-βalkyl, OCι.4alkyl, C2-4alkenyl, Co-2alkylC3.6cycloalkyl, Co- 6alkylaryl, Co-6alkylheteroaryl, OCo-6alkylaryl, OCo-6alkylheteroaryl, NCo-6alkylaryl,
NCo-6alkylheteroaryl,Co-6alkylOaryl, Co-6alkylOheteroaryl, Co-6alkylNaryl, Co- 6alkylNheteroaryl, OCo-βalkylOaryl, OCo-6alkylOheteroaryl, OCo-6alkylNaryl, OCo- 6alkylNheteroaryl, NC0.6alkylOaryl, NCo-βalkylOheteroaryl, NC0-6alkylNaryl, NC0. 6alkylNheteroaryl, O(CO)Cι.4alkyl, C0.4alkyl(CO)OCι.4alkyl, Cι-4alkyl(S)Co-4alkyl, d.4alkyl(SO)C0. alkyl, Cι.4alkyl(SO2)Co.4alkyl, (SO)C0.4alkyl, (SO2)C0.4alkyl, d_
4alkylOR5, C0-4alkylN(C1.4alkyl)2 and a 3- or 6-membered non-aromatic ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A; or ii) selected from the group consisting of benzoimidazolyl, benzooxazolyl, tetrahydrotriazolopyridyl, tetrahydrotriazolopyrimidmyl, pyridonyl, pyridazinyl, imidazopyridyl, oxazolopyridyl, thiazolopyridyl, imidazopyridazinyl, oxazolopyridazinyl, thiazolopyridazinyl and purinyl; and R4 is selected from the group consisting of hydrogen, hydroxy, Co-6alkylcyano, =NR5,
=NOR5, C alkylhalo, halo, Cι-6alkyl, Od.4alkyl, OC0-6alkylaryl, O(CO)CMalkyl, C0. 4alkyl(S)C0-4alkyl, C1.4alkyl(SO)C0-4alkyl, CMalkyl(SO2)Co-4alkyl, (SO)C0.4alkyl, (SO2)Co-4alkyl, d_4alkylOR5, Co-4alkylNR5R6 and a 5- or 6-membered ring containing one or more atoms independently selected from C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring containing one or more atoms independently selected from the group consisting of C, N and O and wherein said ring and said fused ring may be substituted by one or two A;
R5 and R6 are independently selected from the group consisting of hydrogen and d.
6alkyl; wherein any d-βalkyl defined under R1, R2 and R4 may be substituted by one or more A ;
A is selected from the group consisting of hydrogen, hydroxy, halo, nitro, oxo, Co-
6alkylcyano, Co-4alkylC3.6cycloalkyl, Cι.6alkyl, Cι.6alkylhalo, OCι-6alkylhalo, C2.
6alkenyl, C0.3alkylaryl, C0.6alkylOR5, OC2-6alkylOR5, d.6alkylSR5, OC2.6alkylSR5,
(CO)R5, O(CO)R5, OC2.6alkylcyano, OCι.6alkylCO2R5, O(CO)OR5, Od.6alkyl(CO)R5, d.6alkyl(CO)R5, NR5OR6, OC2.6alkylNR5R6, C0-6alkyl(CO)NR5R6, OCi.
6alkyl(CO)NR5R6, OC2.6alkylNR5(CO)R6, C0.6alkylNR5(CO)R6, Co.
6alkylNR5(CO)NR5R6, O(CO)NR5R6, C0.6alkyl(SO2)NR5R6, OC2.6alkyl(SO2)NR5R6, C0.
6alkylNR5(SO2)R6, OC2.6alkylNR5(SO2)R6, SO3R5, C1.6alkylNR5(SO2)NR5R6, OC2.
6alkyl(SO2)R5, C0.6alkyl(SO2)R5, C0.6alkyl(SO)R5, OC2-6alkyl(SO)R5 and a 5-membered ring containing one or more atoms independently selected from the group consisting of C, N, O and S; ml is selected from 0, 1, 2, 3 and 4; m2 is selected from 0, 1, 2 and 3; n is selected from 0, 1 and 2; and t is 0 or 1, or a pharmaceutically acceptable salt or an optical isomer thereof, with the proviso that the compound is not 5-(4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3- thiophen-3 -yl- [ 1 ,2,4] oxadiazole, 1 ,2-di { 2-(3 -amino-phenyl)- [ 1 ,3 ,4] oxadiazole-yl)ethane,
1 ,2-di { 5-[5-(4-nitro-ρhenyl)furan-2-yl] -[ 1 ,3 ,4] oxadiazol-yl)ethane, 1 ,2-di { 5- [5-(4- bromo-phenyl)furan-2-yl] - [ 1 ,3 ,4] oxadiazol-yl)ethane, 1 ,2-di { 5-[5-(4-chloro- phenyl)furan-2-yl]-[l,3,4]oxadiazol-yl)ethane and l,2-di{5-[5-(2,4-dibromo- phenyl)furan-2-yl] - [ 1 ,3 ,4] oxadiazol-yl)ethane; is administered to a subject in need of such inhibition.
22. A method for the treatment of gastro-esophageal reflux disease (GERD), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la as defined in claim 20, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment.
23. A method for the prevention of reflux, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la as defined in claim 20, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such prevention.
24. A method for the treatment of, or prevention of, regurgitation, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la as defined in claim 20, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
25. A method for the prevention of, or treatment of, lung disease, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la as defined in claim 20, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
26. A method for managing failure to thrive, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la as defined in claim 20, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such management.
27. A method for treatment or prevention of asthma, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la as defined in claim 20, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
28. A method according to claim 27, wherein the asthma is reflux-related asthma.
29. A method for treatment or prevention of laryngitis, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula la as defined in claim 20, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
30. A method for the treatment of gastro-esophageal reflux disease (GERD), whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I as defined in claim 21, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment.
31. A method for the prevention of reflux, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I as defined in claim 21, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such prevention.
32. A method for the treatment of, or prevention of, regurgitation, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I as defined in claim 21, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
33. A method for the prevention of, or treatment of, lung disease, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I as defined in claim 21, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
34. A method for managing failure to thrive, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I as defined in claim 21, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such management.
35. A method for treatment or prevention of asthma, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I as defined in claim 21, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
36. A method according to claim 35, wherein the asthma is reflux-related asthma.
37. A method for treatment or prevention of laryngitis, whereby a pharmaceutically and pharmacologically effective amount of a compound of formula I as defined in claim 21, or a pharmaceutically acceptable salt or an optical isomer thereof, is administered to a subject in need of such treatment or prevention.
38. A method according to any one of claims 20-37, wherein the compound of formula I or la is selected from the group of compounds consisting of 2-[5-(3-Methoxy-phenyl)- [l,2,4]oxadiazol-3-ylmethylsulfanyl]-lH-benzoimidazole, 5-(3-Methoxy-phenyl)-3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-[5-(l-Methyl-5-thiophen-2-yl-lH-imidazol-2-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- benzonitrile, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]traiazol-3-ylsulfanylmethyl)-5-phenyl-
[1,2,4] oxadiazole,
2-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-methyl-lH- benzoimidazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- [l,2,4]oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-trifluoromethyl- phenyl)-[l ,2,4]oxadiazole,
3-(3-Methoxy-phenyl)-5-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole, 5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-phenyl-
[1,2,4] oxadiazole,
5-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-m-tolyl-
[1,2,4] oxadiazole,
3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol- 5 -yl] -benzonitrile,
3-[4-Methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[1,2,4] oxadiazole,
3-[5-(2-Methyl-thiazol-4-yl)-[l,3,4]oxadiazol-2-ylsulfanylmethyl]-5-m-tolyl-
[1,2,4] oxadiazole, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[1,2,4] oxadiazole,
3-[5-(2,4-Dimethyl-thiazol-5-yl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m- tolyl- [ 1 ,2,4] oxadiazole,
3-[4-Methyl-5-(5-nitro-furan-2-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl- [l,2,4]oxadiazole,
4-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-[5-(4-tert-Butyl-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[1,2,4] -oxadiazole, 2-Chloro-5-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H- [1 ,2,4]triazol-3-yl]-pyridine,
2-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-benzooxazole,
3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole, 3-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
5-(3-Fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
2-(5-m-Tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-pyridine, 2- [5 -(3 -Methoxy-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-imidazo [4,5- b]pyridine,
5-(3-Fluoro-5-methyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
3-Methyl-5-[3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1, 2,4] oxadiazol-5-yl] -pyridine,
3-(4-Methyl-5-phenyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
2-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-Benzyl-2-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H- [1 ,2,4]triazol-3-yl]-morpholine,
4-[4-Methyl-5-(5-thioρhen-3-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-
3 -yl] -pyridine,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiazol-4-yl-
[1,2,4] oxadiazole, 3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-nitro-phenyl)-
[1,2,4] oxadiazole,
2-Methyl-4-[3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine,
3-[4-Methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-(4-Methyl-5-thiophene-3-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thiazol-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole, 5-(3-Iodo-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole,
5-(3-Ethyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
2-[5-(2-Methyl-pyridin-4-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-lH-benzoimidazole, 2- [5-(3 -Iodo-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H-benzoimidazole,
3-(4-Methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[l,2,4]oxadiazole,
2,6-Dichloro-4-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-
[1 ,2,4]triazol-3-yl] -pyridine, 3-(4-Methyl-5-ρ-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-[l,2,4]oxadiazole,
Dimethyl- {3-[3-(4-methyl-5-thiophen-2-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl]phenyl} -amine,
5-(3-Chloro-ρhenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3- trifluoromethoxy-phenyl) [ 1 ,2,4] oxadiazole,
3-(5-Cyclohexyl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
3-(5-tert-Butyl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- [1,2,4] oxadiazole,
5-(3-Bromo-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
2-[5-(3-Bromo-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-lH-benzoimidazole,
5-(3-Methoxymethyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- lsulfanylmethyl)-[l,2,4]oxadiazole,
2- [5-(3 -Methoxymethyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 H- benzoimidazole,
4-[5-(4-Methyl-5-thiophen-2-yl-4Η-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
3-yl]-pyridine, 2-{l-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-l-methyl-lH- imidazo[4,5-b]pyridine,
2- [5 -(3 -Methoxy-phenyl)- [ 1,2,4] oxadiazol-3 -ylmethylsulfanyl] - 1 -methyl- 1 H- imidazo[4,5-b],
3-[l-Methyl-l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-5-m- tolyl-[ 1,2,4] oxadiazole, 3-[l-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-5-m-tolyl-
[1,2,4] oxadiazole,
3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfonylmethyl)-5-m-tolyl-
[l,2,4]oxadiazole, 3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazole-3-sulfmylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole, or
5-(3-Furan-3-yl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
4-(4-Cyclopropyl-5-{l-[5-(2,5-difluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}- 4Η-[1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-{4-Methyl-5-[l-(5-m-tolyl-[l,2,4]oxadiazol-3-yl)-ethylsulfanyl]-4H-[l,2,4]triazol-3- yl} -pyridine, 5-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-o-tolyl-
[1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-(4-cyclopropyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
2- { 3 - [5 -(2-Fluoro-5 -methyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5 -thiophen-2- yl-[l,2,4]triazol-4-yl}-ethanol,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3 -yl } -pyrimidine,
3-(4-Ethyl-5-furan-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[ 1 ,2,4] oxadiazole, {3-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-
[l,2,4]triazol-4-yl} -acetic acid methyl ester,
5-(2-Fluoro-5-methyl-phenyl)-3-[5-furan-2-yl-4-(2-methoxy-ethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
3-(4-Cyclopropyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5- methyl-phenyl)- [ 1 ,2,4] oxadiazole,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-cyclopropylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-
3 -ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
4-{5-[3-(5-Chloro-2-fluoro-ρhenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4] triazol-3 -yl } -pyrimidine, 3-(5-Cyclopentyl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- [1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-{4-ethyl-5-[2-(4-methoxy-phenyl)-ethyl]-4H-[l,2,4]triazol-3- ylsulfanylmethyl} -[ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-p-tolyloxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(2-methoxy-ethyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
4-(5-{l-[3-(3-Chloro-ρhenyl)-isoxazol-5-yl]-ethylsulfanyl}-4-methyl-4H-[l,2,4]triazol-3- yl)-pyridine,
3-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole, 3-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole,
5-(4-Allyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-furan-2-yl-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]- [1 ,2,4]oxadiazole,
3-(3-Chloro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-
3-yl}-methanol, 3-(3-Chloro-phenyl)-5-[4-ethyl-5-(2-methoxy-ethyl)-4H-[ 1 ,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-methylsulfanylmethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4] oxadiazole,
3-(3-Chloro-ρhenyl)-5-(5-ethoxymethyl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4] oxadiazole, 5-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazole-
3 -carboxylic acid methyl ester,
2-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,3,4]oxadiazole, 2-(3-Chloro-phenyl)-5-(4-cyclopropyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,3,4]oxadiazole,
5-(3-Chloro-phenyl)-3-{ l-[4-ethyl-5-(tetrahydro-furan-2-yl)-4H-[l,2,4]triazol-3- ylsulfanyl] -ethyl } - [ 1 ,2,4] oxadiazole,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H- [ 1 ,2,4]triazol-3-yl)-pyridazine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3-ylmethyl)-pyridine,
5-(5-{ l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridin-2-ol, 4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-phenol,
5-(3-Chloro-phenyl)-3-[5-(4-methoxy-phenoxymethyl)-4-(tetrahydro-furan-2-ylmethyl)-
4H-[1 ,2,4]triazol-3-ylsulfanylmethyl]-[l ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-cyclopropyl-5-(4-methoxy-phenoxymethyl)-4H-[l,2,4]triazol- 3-ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-(4-Ethyl-5-methoxymethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole, 3-[4-Ethyl-5-(tetrahydro-furan-2-yl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-m-tolyl-
[1,2,4] oxadiazole,
2-(3-Chloro-phenyl)-5-{l-[4-ethyl-5-(4-methoxy-ρhenyl)-4H-[l,2,4]triazol-3-ylsulfanyl]- ethyl}-[l,3,4]oxadiazole,
4-{5-[3-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-pyrimidine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyrimidine,
3-(3-Chloro-phenyl)-5-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 5-(3-Methylsulfanyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
2-[5-(3-Methylsulfanyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-lH- benzoimidazole,
5-(2,5-Dimethyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(2-Fluoro-5-methyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(3-Cyclopropyl-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 4-{5-[2-(3-Chloro-phenyl)-oxazol-4-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3-yl}- pyridine,
4-[4-Methyl-5-(5-thiophen-2-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-
3 -yl] -pyridine,
4-{4-Methyl-5-[5-(3-methylsulfanyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H- [1 ,2,4]triazol-3 -yl } -pyridine,
4- { 5 - [5-(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
2-Methyl-4-[3-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazol-5 -yl] -pyridine, l-{3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5 -yl] -phenyl} -ethanone,
4- { 5 - [5-(2-Fluoro-5 -methyl-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
2-Methyl-4-[4-methyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H- [1 ,2,4]triazol-3 -yl] -pyridine,
3 - [5 -(3 -Chloro-phenyl)-isoxazol-3 -ylmethylsulfanyl] -4-methyl-5 -thiophen-2-y 1-4H-
[l,2,4]triazole,
4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine, 3-(4-Butyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methoxy-ρroρyl)-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
3-(4-Benzyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro-phenyl)- [1 ,2,4] oxadiazole, 5-(3-Chloro-ρhenyl)-3-(4-furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
3-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[1 ,2,4]triazol-3-yl}-pyridine, 5-(3-Chloro-phenyl)-3-(4-methyl-5-thiophen-3-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazole,
4- { 5 - [5 -(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H-
[l,2,4]triazol-3-yl}-2-methyl-pyridine,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
3-{5-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine, 5-(3-Chloro-phenyl)-3-(5-thiophen-2-yl-4-thioρhen-2-ylmethyl-4H-[ 1 ,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-{5-[3-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H- [l,2,4]triazol-3-yl}-pyridine,
4- { 5 - [3 -(2-Fluoro-5 -methyl-phenyl)- [ 1 ,2,4] oxadiazol-5 -ylmethylsulfanyl] -4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine,
4-{5-[5-(5 -Bromo-2-fluoro-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 3-{5-[5-(5 -Bromo-2-fluoro-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
5-(5-Bromo-2-fluoro-phenyl)-3-(4-methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-phenyl- [1,2,4] oxadiazole,
3-{5-[5-(3-Fluoro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4-{5-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 5-(3-Fluoro-ρhenyl)-3-(4-methyl-5-thiophen-3-yl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)- [l,2,4]oxadiazole,
3-[4-Methyl-5-(5-thiophen-3-yl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-
3 -yl] -pyridine,
3-(4-Methyl-5-thioρhen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl- [l,2,4]oxadiazole,
2-Chloro-4-[3-(4-methyl-5-pyridin-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5-yl] -pyridine,
2-Chloro-4-[3-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine, 2-Chloro-4-[3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5 -yl] -pyridine,
4-[4-Methyl-5-(5-ρhenyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]tτiazol-3-yl]- pyridine,
3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-phenyl- [1,2,4] oxadiazole,
5-(5-Bromo-2-fluoro-phenyl)-3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4] oxadiazole,
3 - [5 -(3 -Chloro-phenyl)-isoxazol-3 -ylmethylsulfanyl] -4-ethyl-5 -thiophen-2-yl-4H-
[l,2,4]triazole, . 2-Chloro-4-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine,
4-{5-[3-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4] triazol-3 -yl } -pyridine,
3-(3-Fluoro-phenyl)-5-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l ,2,4] oxadiazole, 4-{5-[5-(3 -Chloro-phenyl)- [ 1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-furan-2-ylmethyl-4H-
[l,2,4]triazol-3-yl} -pyridine,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine,
3-{5-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-pyridine, 5-(3-Chloro-phenyl)-3-(4-ethyl-5-thioρhen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-{5-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-furan-2-ylmethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 3-(4-Furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole,
5-(5-Fluoro-2-methyl-ρhenyl)-3-(4-furan-2-ylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-
3 -ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-(4-furan-2-ylmethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
3-[3-(4-Methyl-5-pyridin-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -benzonitrile,
3-[3-(4-Methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -benzonitrile, 3-[3-(4-Methyl-5-thiophen-3-yl-4H-[l ,2,4]triazol-3-ylsulfanylmethyl)-[l ,2,4]oxadiazol-
5-yl]-benzonitrile,
5-(5-Chloro-2-fluoro-ρhenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
2-Chloro-4-[3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1 ,2,4]oxadiazol-5-yl]-pyridine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[1,2,4] oxadiazole, 4-[4-Ethyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-[4-Ethyl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
3-(4-Ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l,2,4]oxadiazole,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine,
3-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4] triazol-3 -yl } -pyridine, 3 - [5 -(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -5-pyridin-4-yl- [ 1 ,2,4]triazol-4-ylamine,
4-{5-[5-(5-Bromo-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-2-yl- [l,2,4]oxadiazole,
3-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -benzonitrile,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-phenyl-
[1,2,4] oxadiazole, 4-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -2-methoxy-pyridine,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
2-Methyl-4-[3-(4-methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4] oxadiazol-5 -yl] -pyridine,
4-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -2-methyl-pyridine, 5-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-2-yl-
[1,2,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
4-[3-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -2-methyl-pyridine,
3-{5-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -benzonitrile,
5-(3-Chloro-phenyl)-3-[5-(3-chloro-ρhenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole, 5-(3-Chloro-ρhenyl)-3-[5-(4-chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
4-{5-[5-(2,5-Dichloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[1 ,2,4] triazol-3 -yl} -pyridine,
5-(2,5-Dichloro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole, . 5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-{5-[5-(2,5-Difluoro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine, 5-(2,5-Dichloro-phenyl)-3-(4-ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
4- { 5- [5 -(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-propyl-4H- [l,2,4]triazol-3-yl} -pyridine,
4- { 5- [5 -(2-Fluoro-5 -methyl-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-propyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-2-yl-
[1,2,4] oxadiazole, 3-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thioρhen-2-yl-
[1,2,4] oxadiazole,
4- [4-Methyl-5-(3 -thiophen-3 -yl- [ 1 ,2,4]oxadiazol-5-ylmethylsulfanyl)-4H-[ 1 ,2,4]triazol-
3 -yl] -pyridine,
5-(4-Methyl-5-thiophen-3-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl- [ 1 ,2,4] oxadiazole,
5-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl-
[1,2,4] oxadiazole,
5-[3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -thiophene-3 -carbonitrile, 5-(3-Chloro-phenyl)-3-[5-(2-fluoro-ρhenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(3-fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(4-fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[ 1 ,2,4] oxadiazole,.
3-(5-Benzo[b]thiophen-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro- phenyl)-[l ,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[5-(3-methoxy-ρhenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-[5-(4-methoxy-ρhenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l ,2,4] oxadiazole,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl- [ 1 ,2,4] oxadiazole,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)- [ 1 ,2,4] oxadiazole,
3-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-pyridin-4-yl-
[1 ,2,4]triazol-4-ylamine, 3-[5-(2-Fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-
[l,2,4]triazol-4-ylamine,
3-Pyridin-4-yl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-[l,2,4]triazol-4- ylamine,
3-Thiophen-2-yl-5-(5-m-tolyl-[l,2,4]oxadiazol-3-ylmethylsulfanyl)-[l,2,4]triazol-4- ylamine,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 4-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-
2-methyl-pyridine,
5-(2,5-Difluoro-phenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-[4-Ethyl-5-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-Ethyl-3-furan-2-yl-5-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazole,
5-(3-Chloro-phenyl)-3-[5-(3,5-dichloro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-(4-ethyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-m-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-nitro-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,2,4]oxadiazole, 4-{5-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-methyl-4H-[l,2,4]triazol-3- yl} -pyridine,
5-(3-Chloro-ρhenyl)-3-[5-(2,5-difluoro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(3-chloro-phenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(4-chloro-ρhenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine, 3 - [5-(3 -Chloro-phenyl)-oxazol-2-ylmethylsulfanyl] -4-ethyl-5 -thiophen-2-yl-4H-
[l,2,4]triazole,
3-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
5-(2-Chloro-5-methyl-ρhenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
4-{5-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-ethyl-4H-[l,2,4]triazol-3-yl}- pyridine,
3 - [3 -(3 -Chloro-pheny l)-isoxazol-5 -ylmethylsulfanyl] -4-ethyl-5 -thiophen-2-yl-4H-
[l,2,4]triazole, 3-[3-(3-Chloro-phenyl)-isoxazol-5-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
4-{5-[5-(2-Fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
5-(2,5-Dichloro-thiophen-3-yl)-3-(4-ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
4-{5-[5-(2,5-Dichloro-thiophen-3-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-4H-
[1 ,2,4]triazol-3-yl} -pyridine, 4-Ethyl-3-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-
4H-[l,2,4]triazole,
4-Ethyl-3-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-5-furan-2-yl-4H-
[l,2,4]triazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole, 3-(3-Chloro-phenyl)-5-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thiophen-3-yl-
[1,2,4] oxadiazole, 5 5-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thiophen-3-yl-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-fluoro-phenyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(4-fluoro-ρhenyl)-4H-[l,2,4]triazol-3- l o ylsulfanylmethyl] -[1,2,4] oxadiazole,
3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-thioρhen-2-yl-
[1,2,4] oxadiazole,
3-{3-[5-(3-Chloro-thiophen-2-yl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[l,2,4]oxadiazol-5-yl}-benzonitrile, is 4-{5-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine,
2-(3-Chloro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,3,4]oxadiazole,
5-(3-Chloro-ρhenyl)-3-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3- 20 ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(2-fluoro-5-methyl-phenyl)-4-furan-2-ylmethyl-4H-
[l,2,4]triazol-3-ylsulfanylmethyl]-[l,2,4]oxadiazole,
4-[3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -2-methyl-pyridine, 25 3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-methoxy- phenyl)- [ 1 ,2,4] oxadiazole,
5-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-(3-methoxy- phenyl)- [ 1 ,2,4] oxadiazole,
5-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-thioρhen-2-yl- 30 [1,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
3-[3-(4-Ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -benzonitrile, 5 3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-trifluoromethyl-4H- [l,2,4]triazole,
3-[5-(3-Chloro-phenyl)-oxazol-2-ylmethylsulfanyl]-4-ethyl-5-trifluoromethyl-4H-
[l,2,4]triazole,
4-Ethyl-3-(5-thiophen-3-yl-isoxazol-3-ylmethylsulfanyl)-5-trifluoromethyl-4H- [l,2,4]triazole,
4-{3-[5-(3-Fluoro-ρhenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[1,2,4] oxadiazol-5 -yl } -2-methyl-pyridine,
4-{3-[5-(3-Chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[ 1 ,2,4] oxadiazol-5 -yl } -2-methyl-pyridine, 4-{3-[5-(4-Chloro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-
[ 1 ,2,4]oxadiazol-5-yl} -2-methyl-pyridine,
4- { 3 -[5-(4-Methoxy-phenyl)-4-methyl-4H- [ 1 ,2,4]triazol-3-ylsulfanylmethyl] -
[ 1 ,2,4] oxadiazol-5-yl} -2-methyl-pyridine,
4-[3-(4-Ethyl-5-p-tolyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-2- methyl-pyridine,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-fluoro-phenyl)-
[1,2,4] oxadiazole,
4-{4-Ethyl-5-[5-(3-fluoro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 5-(3-Chloro-phenyl)-3-[5-(3,5-difluoro-ρhenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[5-(2,6-difluoro-ρhenyl)-4-ethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1,2,4] oxadiazole,
2-[3-(4-Ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl]-4-methyl-phenol,
3-{l-[5-(3-Chloro-ρhenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
4-(5-{l-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridine, 3-[5-(4-Butoxy-phenyl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(3-chloro- phenyl)- [1,2,4] oxadiazole,
3-(5-Benzo[l,3]dioxol-5-yl-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-chloro- phenyl)- [1,2,4] oxadiazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-methyl-thiazol-4- yl)-[ 1,2,4] oxadiazole, 3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-fluoro-phenyl)-
[1,2,4] oxadiazole,
4-Ethyl-3-{l-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-5-furan-2-yl-
4H-[l,2,4]triazole, 4-(4-Ethyl-5-{ 1 -[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methyl-3H-imidazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(l-methyl-lH-imidazol-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[1 ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(l-methyl-lH-imidazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-4-methyl-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine, 3 - [5 -(3 -Chloro-pheny l)-4-methyl-isoxazol-3 -ylmethylsulfanyl] -4-ethyl-5 -furan-2-yl-4H-
[l,2,4]triazole,
3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-methyl-thiophen-
2-yl)-[l ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methyl-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl]- [1 ,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(5-methyl-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
4-{5-[4-Chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine, 3-[4-Chloro-5-(3-chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
2-Chloro-4-{5-[5-(3-chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[1 ,2,4]triazol-3-yl}-6-methyl-pyridine,
3-[5-(5-Bromo-furan-2-yl)-4-ethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(3-chloro- phenyl)-[l,2,4]oxadiazole,
2-Chloro-4-{5-[5-(3-chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl} -pyridine,
2-Chloro-4-{5-[5-(3-chloro-phenyl)-[l,2,4]oxadiazol-3.-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-6-methoxy-pyridine, 2-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-methyl-benzonitrile,
5-(3-Chloro-phenyl)-3-[4-ethyl-5-(3-methoxy-thiophen-2-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
3-[5-(5-Chloro-thiophen-3-yl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H- [l,2,4]triazole,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-
5 -fluoro-benzonitrile,
4-Ethyl-3-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-5-thiophen-2-yl-4H-[l,2,4]triazole,
4-Methyl-3-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-5-thiophen-3-yl-4H-[l,2,4]triazole, 4-Ethyl-3-furan-2-yl-5-(5-phenyl-isoxazol-3-ylmethylsulfanyl)-4H-[l,2,4]triazole,
4- [4-Ethyl-5 -(5-pheny l-isoxazol-3 -ylmethylsulfanyl)-4H- [ 1 ,2,4] triazol-3 -yl] -pyridine,
4- [4-Methyl-5 -(5 -phenyl-isoxazol-3 -ylmethylsulfanyl)-4H- [ 1 ,2,4] triazol-3 -yl] -pyridine,
2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-m-tolyl-
[l,3,4]oxadiazole, 4-[4-Methyl-5-(5-m-tolyl-[l,3,4]oxadiazol-2-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-[4-Ethyl-5-(5-m-tolyl-[l,3,4]oxadiazol-2-ylmethylsulfanyl)-4H-[l,2,4]triazol-3-yl]- pyridine,
4-{5-[5-(5-Chloro-thiophen-3-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-pyridine,
3-[3-(4-Ethyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-fluoro-benzonitrile,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-
4-fluoro-benzonitrile, 3-[3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5- yl] -4-fluoro-benzonitrile,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]- benzonitrile,
3-[5-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-3-yl]- benzonitrile,
3-[3-(4-Methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -benzonitrile,
5-(5-Chloro-2-fluoro-phenyl)-3-(4-methyl-5-trifluoromethyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 2-Chloro-4-[3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [ 1 ,2,4]oxadiazol-5-yl]-pyridine,
2-Chloro-4-[3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,2,4]oxadiazol-5-yl]-pyridine,
2-(3-Chloro-phenyl)-5-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,3 ,4] oxadiazole,
2-(3-Chloro-phenyl)-5-(4-methyl-5-thiazol-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,3,4]oxadiazole,
2-(3-Chloro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,3, 4] oxadiazole, 2-(3-Chloro-phenyl)-5-(4-ethyl-5-trifluoromethyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,3, 4] oxadiazole,
4-{4-Ethyl-5-[5-(4-methyl-thiophen-2-yl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[l,2,4]triazol-3-yl}-pyridine,
3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(4-methyl-thiophen-2- yl)-[ 1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-{5-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-{4-Ethyl-5-[5-(3-nitro-ρhenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4H-[l,2,4]triazol-
3 -yl} -pyridine,
2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-nitro-ρhenyl)-
[l,3,4]oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H-[l,2,4]triazol- 3-yl}-pyridine,
3-[5-(3-Chloro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-(4-methoxy-phenyl)-4H-
[l,2,4]triazole,
5-(3-Chloro-phenyl)-3-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)- ethyl]-[l ,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-[l-(4-ethyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[1,2,4] oxadiazole,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H- [l,2,4]triazol-3-yl)-pyridine, 3-[5-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -benzonitrile,
3-[5-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2-yl]- benzonitrile, 3-[5-(4-Methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -benzonitrile,
3-[5-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -benzonitrile,
4-{5-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-methyl-4H- [l,2,4]triazol-3-yl}-pyridine,
4-{5-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyridine,
4- { 5- [5-(5-Chloro-2-fluoro-phenyl)- [ 1 ,3 ,4]oxadiazol-2-ylmethylsulfanyl] -4-cyclopropyl-
4H-[l,2,4]triazol-3-yl}-pyridine, 2-(5-Chloro-2-fluoro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenyl)-4H-[ 1 ,2,4]triazol-3- y lsulfanylmethyl] -[1,3,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4-ethyl-4H- [l,2,4]triazol-3-yl}-pyridine,
2-(3-Chloro-phenyl)-5-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,3 ,4] oxadiazole,
2-(3-Chloro-phenyl)-5-[l-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[1,3, 4] oxadiazole, 5-(5-Chloro-2-fluoro-phenyl)-3-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanyl)-ethyl] - [ 1 ,2,4] oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-
4H-[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H- [l,2,4]triazol-3-yl)-pyridine,
2-Chloro-4-[3-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine,
4- {5- [5-(2-Fluoro-5-methyl-phenyl)- [ 1 ,3,4] oxadiazol-2-ylmethylsulfanyl] -4-methyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-{4-Ethyl-5-[5-(2-fluoro-5-methyl-ρhenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-4H- [ 1 ,2,4]triazol-3-yl} -pyridine,
4-{4-Cyclopropyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-ylmethylsulfanyl]-
4H-[l,2,4]triazol-3-yl}-pyridine,
2-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(2-fluoro-5-methyl- phenyl)-[l,3,4]oxadiazole,
2-[4-Ethyl-5-(4-methoxy-ρhenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]-5-(2-fluoro-5- methy 1-phenyl)- [1,3,4] oxadiazole,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-4H-
[l,2,4]triazol-3-yl}-pyridine, 4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-methyl-4H-
[1 ,2,4]triazol-3-yl}-pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-methyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl}-pyridine,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine, 3-[5-(5-Chloro-2-fluoro-phenyl)-isoxazol-3-ylmethylsulfanyl]-4-ethyl-5-furan-2-yl-4H-
[l,2,4]triazole,
3 - { 1 - [5 -(5-Chloro-2-fluoro-phenyl)-isoxazol-3 -yl] -ethylsulfanyl } -4-ethyl-5 -furan-2-yl-
4H-[l,2,4]triazole,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H- [l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Chloro-ρhenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine, 5-(5-Chloro-2-fluoro-phenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(5-CWoro-2-fluoro-phenyl)-3-(5-furan-3-yl-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4-Chloro-2-[3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazol-5 -yl] -phenol, 2-Chloro-4-[5-(4-methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -pyridine,
2-Chloro-4-[5-(4-ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,3,4] oxadiazol-2-yl] -pyridine, 2-Chloro-4-[5-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -pyridine,
2-Chloro-4-[5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -pyridine,
2-Chloro-4-{5-[4-ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanylmethyl]- [1,3,4] oxadiazol-2-yl } -pyridine,
2-(3-Chloro-ρhenyl)-5- { 1 -[5-(4-methoxy-phenyl)-4-methyl-4H-[ 1 ,2,4]triazol-3- ylsulfanyl] -ethyl } - [ 1 ,3 ,4] oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-
4H-[ 1 ,2,4]triazol-3-yl)-ρyridine, 5-(5-Bromo-2-fluoro-ρhenyl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
2-(3-Chloro-phenyl)-5-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,3 ,4] oxadiazole,
4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-cyclopropyl-4H- [l,2,4]triazol-3-yl} -pyridine,
4- { 5 - [5-(3 -Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-cyclopropyl-4H-
[ 1 ,2,4] triazol-3 -yl} -pyridine,
4-(5- { 1 - [5-(2-Fluoro-5-methyl-phenyl)- [ 1 ,3,4] oxadiazol-2-yl] -ethylsulfanyl } -4-methyl-
4H-[l,2,4]triazol-3-yl)-ρyridine, 4-(4-Ethyl-5- { 1 -[5-(2-fluoro-5-methyl-phenyl)- [ 1 ,3 ,4] oxadiazol-2-yl] -ethylsulfanyl} -4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-yl]- ethylsulfanyl}-4H-[l,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropylmethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,3,4]oxadiazol-2-yl]- ethylsulfanyl }-4H-[l ,2,4]triazol-3-yl)-pyridine,
2-(2-Fluoro-5-methyl-phenyl)-5- { 1 -[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-
[l,2,4]triazol-3-ylsulfanyl]-ethyl}-[l,3,4]oxadiazole,
4-(5- { 1 -[5-(5-Chloro-2-fluoro-phenyl)-[ 1 ,3,4]oxadiazol-2-yl]-ethylsulfanyl} -4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine, 4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4- cyclopropyl-4H-[l,2,4]triazol-3-yl)-pyridine,
2-(5-CMoro-2-fluoro-phenyl)-5-[l-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)- ethyl] -[ 1 ,3 ,4] oxadiazole,
2-(5-Chloro-2-fluoro-phenyl)-5- { 1 -[4-methyl-5-(2-methyl-thiazol-4-yl)-4H- [1 ,2,4]triazol-3-ylsulfanyl]-ethyl}-[l ,3 ,4] oxadiazole,
4-(4-Cyclopropylmethyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-isoxazol-3-yl]- ethylsulfanyl}-4H-[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine, 4-(4-Cycloproρyl-5-{l-[5-(3-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4H-
[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(4-Methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-
[l,3,4]oxadiazol-2-yl)-2 -methyl-pyridine,
4-(5-{l-[4-Ethyl-5-(4-methoxy-phenyl)-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}- [1 ,3,4]oxadiazol-2-yl)-2 -methyl-pyridine,
4-{5-[l-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,3,4]oxadiazol-2- yl } -2-methyl-pyridine,
4-{5-[l-(4-Cyclopropyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-
[l,3,4]oxadiazol-2-yl}-2 -methyl-pyridine, 4-{5-[l-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,3,4]oxadiazol-2- yl } -2-methyl-pyridine,
2-(3-Chloro-phenyl)-5-{ l-[4-methyl-5-(2-methyl-thiazol-4-yl)-4H-[l,2,4]triazol-3- ylsulfanyl] -ethyl } - [ 1 ,3 ,4] oxadiazole,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H- [l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4-methyl-4H-
[l,2,4]triazol-3-yl)-2-methyl-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl)-pyridine, 5-(3-Chloro-phenyl)-3-{l-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanyl] -ethyl } - [ 1 ,2,4] oxadiazole,
4-(5-{l-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4- cyclopropyl-4H-[ 1 ,2,4]triazol-3-yl)-pyridine,
5-(5-Chloro-2-fluoro-ρhenyl)-3-{l-[5-(4-methoxy-phenyl)-4-methyl-4H-[l,2,4]triazol-3- ylsulfanyl]-ethyl}-[l,2,4]oxadiazole, 4-[5-(4-Ethyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -2-methyl-pyridine,
4-[5-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[ 1 ,3 ,4] oxadiazol-2-yl] -2-methyl-pyridine, 4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-cyclopropyl-
4H-[l,2,4]triazol-3-yl}-pyridine,
4-[5-(5-Furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,3,4]oxadiazol-2- yl] -2-methyl-pyridine,
4-(5-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-4- cyclopropylmethyl-4H-[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(4-Fluoro-phenyl)-4-methyl-4H-[l,2,4]triazol-3-ylsulfanyl]-ethyl}-
[l,3,4]oxadiazol-2-yl)-2-methyl-pyridine,
4-(5- { 1 -[5-(3-Fluoro-phenyl)-4-methyl-4H-[ 1 ,2,4]triazol-3-ylsulfanyl] -ethyl} -
[ 1 ,3 ,4] oxadiazol-2-yl)-2 -methyl-pyridine, 3 - [3 -(4-Cyclopropyl-5 -pyridin-4-yl-4H- [ 1 ,2,4] triazol-3 -ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-4-fluoro-benzonitrile,
4-Chloro-2-[3-(4-cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1 ,2,4]oxadiazol-5-yl]-phenol,
4- { 4-Cyclopropyl-5 - [5 -(3 -methoxy-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4H- [l,2,4]triazol-3-yl} -pyridine,
4-{4-Cyclopropyl-5-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-
4H-[l,2,4]triazol-3-yl}-ρyridine,
4-{4-Cyclopropyl-5-[5-(3-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4H-
[l,2,4]triazol-3-yl}-pyridine, 4- [4-Cyclopropyl-5 -(5-m-tolyl- [1,2,4] oxadiazol-3 -ylmethylsulfanyl)-4H- [ 1 ,2,4] triazol-3 - yl] -pyridine,
3-[3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-benzonitrile,
4- { 4-Cyclopropyl-5 - [5 -(2, 5 -difluoro-phenyl)- [1,2,4] oxadiazol-3 -ylmethylsulfanyl] -4H- [1 ,2,4]triazol-3-yl}-pyridine,
4- {4-Cycloρroρyl-5-[ 1 -(5-m-tolyl- [ 1 ,2,4] oxadiazol-3 -yl)-ethylsulfanyl] -4H-
[1 ,2,4]triazol-3-yl}-pyridine,
4-(4-Cyclopropyl-5-{l-[5-(3-methoxy-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4H-
[1 ,2,4]triazol-3-yl)-pyridine, 4- { 5 - [5-(2-Chloro-5-methyl-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-cyclopropyl- 4H-[l,2,4]triazol-3-yl}-pyridine,
2-[3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazol-5 -yl] -4-methyl-phenol,
4-(5-{l-[5-(2-Chloro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4- cyclopropyl-4H-[l,2,4]triazol-3-yl)-pyridine,
{3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -phenyl } -methanol,
3-[5-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
3 -yl] -phenol, 5-(3-Chloro-phenyl)-3-[4-(tetrahydro-furan-2-ylmethyl)-5-thiophen-2-yl-4H-
[ 1 ,2,4]triazol-3 -ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
(2-Chloro-phenyl)- { 5 - [5 -(3 -chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4- isobutyl-4H-[l,2,4]triazol-3-yl}-methanol,
5-(2-Fluoro-5-methyl-phenyl)-3-[5-thiophen-2-yl-4-(2,2,2-trifluoro-ethyl)-4H- [l,2,4]triazol-3-ylsulfanylmethyl]-[l,2,4]oxadiazole,
3-(2,5-Difluoro-ρhenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5 -Furan-3 -yl-3 -(4-methyl-5 -thiophen-2-yl-4H- [ 1 ,2,4] triazol-3 -ylsulfanylmethyl)-
[1,2,4] oxadiazole, 3-(3-Chloro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3 -(3 -Chloro-phenyl)-5 -(5 -furan-3 -yl-4-methyl-4H- [ 1 ,2,4]triazol-3 -ylsulfany lmethyl)- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(5-ruran-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(5-furan-3-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl} -pyrimidine, 4-{5-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4] triazol-3 -yl } -pyrimidine,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-(5-Chloro-2-fluoro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole, 5-(5-Chloro-thiophen-2-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-(5-Chloro-thiophen-2-yl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 5-(5-Chloro-thiophen-3-yl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
4- { 5-[5-(3-Chloro-phenyl)- [ 1 ,2,4] oxadiazol-3 -ylmethylsulfanyl] -4-ethyl-4H-
[l,2,4]triazol-3-ylmethoxy}-phenol,
4- { 5- [5-(5-Chloro-2-fluoro-phenyl)- [ 1 ,3,4] oxadiazol-2-ylmethylsulfanyl] -4-ethyl-4H- [ 1 ,2,4]triazol-3-ylmethoxy} -phenol,
3-(2,5-Difluoro-phenyl)-5-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
3-(2,5-Difluoro-phenyl)-5-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 4-(5-{l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethylsulfanyl}-4-methyl-4H-
[l,2,4]triazol-3-yl)-pyridine,
4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-cyclopropyl-
4H- [ 1 ,2,4] triazol-3 -yl } -pyrimidine,
2-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H- [ 1 ,2,4]triazol-3 -yl)-5 -methoxy-pyrimidine,
2-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[l,2,4]triazol-3-yl)-pyrimidine,
4-(5.{l.[5.(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl)-2-methoxy-pyridine, 5-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[ 1 ,2,4]triazol-3-yl)-2-methoxy-pyridine,
2-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H-
[1 ,2,4]triazol-3-yl)-5-methoxy-pyridine,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-ethyl-4H- [l,2,4]triazol-3-yl)-6-methoxy-pyridazine,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-cycloρropyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
4-{5-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-ylmethylsulfanyl]-4-methyl-4H-
[1 ,2,4]triazol-3-yl}-pyridine, 5-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-isobutyl-4H-[ 1 ,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methylsulfanyl-propyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-(4-hexyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-cyclopropylmethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-fluoro-benzyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole, 5-(3-Chloro-phenyl)-3-[4-(3-methyl-benzyl)-5-thioρhen-2-yl-4H-[ 1 ,2,4]triazol-3- ylsulfanylmethyl]-[l,2,4]oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(2-methyl-butyl)-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-[4-(3-methyl-butyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfany lmethyl]-[l ,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-[4-(2-fluoro-benzyl)-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] -[ 1 ,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yloxymethyl)-
[1,2,4] oxadiazole, 4-{5-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethoxy]-4-methyl-4H-
[l,2,4]triazol-3-yl} -pyridine,
4-(5-{l-[5-(3-Chloro-ρhenyl)-[l,3,4]oxadiazol-2-yl]-ethoxy}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
4-(5-{l-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethoxy}-4-methyl-4H-[l,2,4]triazol-3-yl)- pyridine,
5-(2-Methoxy-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole,
5-Furan-2-yl-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole, 3-[3-(4-Methyl-5-thioρhen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5-yl]-benzoic acid methyl ester,
5-(2-Fluoro-ρhenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(2,5-Difluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[l,2,4]oxadiazole, 3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(3-vinyl-phenyl)- [1,2,4] oxadiazole,
5-(3-Difluoromethoxy-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole, 5-(4-Methoxy-thiophen-3-yl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)- [1,2,4] oxadiazole,
5-(2-Chloro-ρhenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(4-Fluoro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)- [1,2,4] oxadiazole,
3-(3-Chloro-phenyl)-5-[l-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanyl)- ethyl] - [ 1 ,2,4] oxadiazole,
-(5-{l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethylsulfanyl}-4-methyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine, 3-(3-Chloro-phenyl)-5-[2-(4-ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[ 1 ,2,4] oxadiazole,
5-(3-Chloro-ρhenyl)-3-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-ylmethyl)-
[1,2,4] oxadiazole,
2-(3-Chloro-phenyl)-5-[2-(5-furan-2-yl-4-methyl-4H-[l,2,4]triazol-3-yl)-ethyl]- [l,3,4]oxadiazole,
2-(3-Chloro-phenyl)-5-[2-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[l,3,4]oxadiazole,
2-(3-Cmoro-phenyl)-5-[2-(4-cyclopropyl-5-furan-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[1,3, 4] oxadiazole, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-methyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-ethyl-4H-[l,2,4]triazol-3- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-ethyl}-4-cycloρropyl-4H- [ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-4-cyclopropyl-4H-
[1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[3-(3 -Chloro-phenyl)- [1,2,4] oxadiazol-5 -yl] -2-methyl-propyl } -4-cy clopropyl-
4H-[l,2,4]triazol-3-yl)-pyridine, 4-(5-{2-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-propyl}-4-cyclopropyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[1 ,2,4]triazolo[4,3-a]pyridine,
8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-thiophen-2-yl-5,6,7,8-tetrahydro- [1 ,2,4]triazolo[4,3-a]pyridine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8- tetrahydro-[l,2,4]triazolo[4,3-a]pyridine,
5-(5-Bromo-4-methyl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-3-(3-chloro-phenyl)-
[1,2,4] oxadiazole, 3-[3-(4-Methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-
5 -yl] -phenylamine,
5-(3-Chloro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfonylmethyl)-
[1,2,4] oxadiazole,
5-(3-Chloro-phenyl)-3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazole-3-sulfmylmethyl)- [l,2,4]oxadiazole,
2-Methyl-6-[3-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-
[l,2,4]oxadiazol-5-yl]-pyridine,
4-(5-{ 1 -[5-(3-Chloro-phenyl)-[l ,2,4] oxadiazol-3 -yl] -ethylsulfanyl }-4-ethyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridin-2-ol, 4-(5-{2-[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ρropyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
[5-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethyl]-methyl-(4-methyl-5-pyridin-4-yl-4H-
[ 1 ,2,4]triazol-3-yl)-amine,
8-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro- [ 1 ,2,4]triazolo[4,3-a]pyrimidine,
8-[5-(5-Chloro-2-fluoro-phenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8- tetrahydro-[l,2,4]triazolo[4,3-a]pyrimidine,
8-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-
[ 1 ,2,4]triazolo[4,3-a]pyrimidine, 8-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethyl}-3-pyridin-4-yl-5,6,7,8- tetrahydro-[l,2,4]triazolo[4,3-a]pyrimidine,
8-[5-(5-Chloro-2-fluoro-ρhenyl)-[l,2,4]oxadiazol-3-ylmethyl]-3-furan-2-yl-5,6,7,8- tetrahydro-[l,2,4]triazolo[4,3-a]pyrimidine,
8-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethyl}-3-pyridin-4-yl-5,6,7,8- tetrahydro-[l ,2,4]triazolo[4,3-a]pyrimidine, 3-(4-Ethyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-5-(lH-pyrrol-3-yl)-
[1,2,4] oxadiazole,
4-{5-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-
[ 1 ,2,4]triazol-3 -yl } -pyridine 1 -oxide, 5-(3-CWoro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-
[1,2,4] oxadiazole,
5-(5-Chloro-2-fluoro-phenyl)-3-[4-(2-fluoro-ethyl)-5-thioρhen-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl] - [ 1 ,2,4] oxadiazole,
5-(5-Chloro-thiophen-3-yl)-3-(4-ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3- ylsulfanylmethyl)-[ 1 ,2,4] oxadiazole,
3-[3-(4-Ethyl-5-furan-2-yl-4H-[l,2,4]triazol-3-ylsulfanylmethyl)-[l,2,4]oxadiazol-5-yl]-
4-hydroxy-benzonitrile,
3-(3-Chloro-phenyl)-5-[2-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[1,2,4] oxadiazole, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-[l,3,4]oxadiazol-2-yl)- pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3 -yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-4-cyclopropyl-4H- [l,2,4]triazol-3-yl)-pyridine, or
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l,l-dimethyl-ethyl}-
[ 1 ,3,4]oxadiazol-2-yl)-pyridine,
3-(5-{l-[5-(3-Chloro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethoxy}-4-cyclopropyl-4H-
[l,2,4]triazol-3-yl)-pyridine, 4-(5-{l-[5-(2-Chloro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-
4H-[ 1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(2,5-Difluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl-4H-
[l,2,4]triazol-3-yl)-pyridine,
4-(5-{l-[5-(2-Fluoro-5-methyl-ρhenyl)-[l,2,4]oxadiazol-3-yl]-ethylsulfanyl}-4-methyl- 4H-[1 ,2,4]triazol-3-yl)-pyridine,
4-(4-Cyclopropyl-5-{l-[5-(2-fluoro-5-methyl-phenyl)-[l,2,4]oxadiazol-3-yl]- ethylsulfanyl}-4H-[l,2,4]triazol-3-yl)-pyridine,
3-{3-[l-(4-Methyl-5-pyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]-[l,2,4]oxadiazol-
5-yl } -benzonitrile, 3-{3-[l-(4-Cyclopropyl-5-ρyridin-4-yl-4H-[l,2,4]triazol-3-ylsulfanyl)-ethyl]- [l,2,4]oxadiazol-5-yl}-benzonitrile,
3-{l-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-ethylsulfanyl}-5-pyridin-4-yl-
[ 1 ,2,4]triazol-4-ylamine, 3-(3-Chloro-phenyl)-5-[2-(4-methyl-5-thiophen-2-yl-4H-[l,2,4]triazol-3-yl)-ethyl]-
[1,2,4] oxadiazole,
4-(5-{2-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-4-cycloρroρyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine, cis-4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-4-cyclopropyl-4H- [1 ,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l,l-dimethyl-ethyl}-
[1,3,4] oxadiazol-2-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-methyl-propyl}-[l,3,4]oxadiazol-
2-yl)-pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-l-methyl-ethyl}-[l,3,4]oxadiazol-2- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-[l,3,4]oxadiazol-2- yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-cyclopropyl}-4-methyl-4H- [l,2,4]triazol-3-yl)-pyridine,
4-(5-{2-[5-(3-Chloro-phenyl)-[l,3,4]oxadiazol-2-yl]-proρyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-ρhenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-[l,3,4]oxadiazol-2-yl)- pyridine, 4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-4-methyl-4H-[l,2,4]triazol-
3-yl)-pyridine,
4-(5-{2-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-propyl}-4-cyclopropyl-4H-
[ 1 ,2,4]triazol-3-yl)-pyridine,
(S)-[l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H- [l,2,4]triazol-3-yl)-ethyl]-carbamic acid tert-butyl ester,
(S)-l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cycloproρyl-5-pyridin-4-yl-4H-
[l,2,4]triazol-3-yl)-ethylamine, (S)-[l-[3-(3-Chloro-phenyl)-[l,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H-
[l,2,4]triazol-3-yl)-ethyl]-dimethyl-amine, or a pharmaceutically acceptable salt or an optical isomer thereof.
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