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IE43698B1 - 3-iminoalkyl-2-(1h)-pyridines - Google Patents

3-iminoalkyl-2-(1h)-pyridines

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Publication number
IE43698B1
IE43698B1 IE1724/76A IE172476A IE43698B1 IE 43698 B1 IE43698 B1 IE 43698B1 IE 1724/76 A IE1724/76 A IE 1724/76A IE 172476 A IE172476 A IE 172476A IE 43698 B1 IE43698 B1 IE 43698B1
Authority
IE
Ireland
Prior art keywords
compound
formula
stated
methyl
ethyl
Prior art date
Application number
IE1724/76A
Other versions
IE43698L (en
Original Assignee
Sandoz Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sandoz Ltd filed Critical Sandoz Ltd
Publication of IE43698L publication Critical patent/IE43698L/en
Publication of IE43698B1 publication Critical patent/IE43698B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Anesthesiology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The compounds of the formulae Ia and Ib in which the symbols have the meanings given in Claim 1 are suitable as starting materials for pharmaceutically active substances. They are obtained by reacting a compound of the formula II with a compound of the formula III as defined in Claim 1 or by oxidation of a compound of the formula Ib as defined in Claim 2 and obtained in this way.

Description

This invention relates to 3-iminoalky 1-2(111)pyridines.
More particularly, this invention provides compounds of formula X, R. ‘1 ro •r. '2 in which R^ is alkyl of 1 to 4 carbon atoms or cycloaikyl of 3 to- 6 carbon atoms, Ρ^2 is hydrogen, fluorine, chlorine, or alkyl or alkoxy of 1 to 4 carbon atoms, and is straight chain alkyl, of 1 to 4 carbon atoms.
The compounds of formula I may exi st in tautomeric forms of formulae Ia, Ib and Ic, Ia Ib in which R , R2 and R3 are as defined above.
While reference is made hereinafter only to the form of formula I, or the corresponding chemical name, it is to be understood that the invention is not intended to be limited to any particular form of the compounds.
The invention also provides a process for the production of compounds of formula X, characterised by reducing a compound of formula XI, The reduction is suitably effected by catalytic hydrogenation and in an inert organic solvent. Suitable catalysts include palladium on carbon, platinum oxide and Raney nickel and suitable solvents include lower alkanols, such as methanol or, preferably, ethanol. The reaction temperature is suitably from 10° to 50°C, preferably 20° to 30°C, and the reaction time may vary, for example from 1 to 10, more usually 2 to 3, hours.
The resulting compounds of formula I may be isolated and purified using conventional techniques. Where required, non salt forms of the compounds may be converted into acid or base addition salt forms ih conventional manner, and vice versa.
The compounds of formula II may be produced in accordance with the following reaction scheme:3 43598 Step d) Inert organic Solvent RpR2 an<^ R3 as defined above, and signifying alkyl of 1 to 4 carbon atoms.
;The cyclisation in step a) is suitably effected with an acid, e.g. hydrochloric, u-toluenesulphonic, poly phosphoric or, preferably sulphuric acid and in an inert Organic solvent,· such as an aromatic hydrocarbon, e.g. benzene or toluene, or, alternatively and preferably, employing an excess of the acid to provide a reaction medium. The reaction temperature is suitably from 80° to 150°C, preferably the reflux temperature of the reaction medium, and the reaction time may vary, for example from 12 to 36 hours, more usually 20 to 36 hours.
The oxidation in step b) is suitably effected with potassium permanganate or, preferably, chromium trioxi.de, under acid conditions, provided for example by sulphuric, hydrochloric or, preferably, acetic acid, and in the presence of water. The reaction temperature is suitably from 10° to 50°C, preferably 20° to 30°C and the reaction time may vary, for example from 1 to 5, more usually 1.5 to 2.5 hours.
Suitable solvents for use in step c) include ethers, such as diethyl ether or tetrahydrofuran, and aliphatic hydrocarbons, such as hexane, pentane or heptane, preferably tetrahydrofuran. The reaction temperature may, for example, be from -75° to -55°C, prefer4 3 6 3 3 ably -65° to -60°C, and the reaction time may vary, for example from 1 to 5, more usually 2.5 to 3.5 hours.
Step d) is suitably effected in the same solvents as described above for step c), hexane being preferred, however, and under the same conditions as for step c).
The resulting compounds of formulae II, III, IV and V may be isolated and purified using conventional techniques. Where required, non salt forms of the compounds of formula II, III and IV may be converted into acid or base addition salt forms in conventional manner, or vice versa.
The compounds of formula VI,· VII and VIII are either known or may be produced in conventional manner from available materials.
The compounds of formula I possess pharmacological activity. In particular, they possess sleepinducing, minor tranquillising and neuroleptic activity, as indicated 1) by the hexobarbital reinduction method of Winter, J. Pharmacol, and Exp. Therap. 94., 7-11 (1948), in which the re-induction of anaesthesia is used to determine sedative-hypnotic activity in mice given 70 mg/kg of animal body weight i.p. of hexobarbital followed immediately after the mice regain their righting reflexes by 4 to 200 mg/kg of animal body weight i.p. of the test compound; 2) by their ability to produce docility in behaviour tests in mice given 20 to 200 mg/kg of animal body weight, i.p. of the test compound, according to the 30-word adjective check sheet system basically as described by Irwin S. (Gordon Research Conference, Medicinal Chemistry, 1959) and Chen (Symposium on Sedative and Hypnotic Drugs, Williams and Wilkins, 1954); 3) by their ability to antagonise chronic convulsions and death in mice given about 35 to 250 mg/kg of the test compound followed immediately by 50 mg/kg i.p. of N-sulfamoylazepine; 4). by the apomorphine gnawing test basically as described by the method of Ernst [Psychopharmacologica 10, 316 to 323 (1967)] in which male Wistar rats weighing 90 to 110 g are given 17.3 mg/kg p.o. of the test compound followed 30 minutes later by 10 mg/kg i.p. of apomorphine. It is well known that gnawing is induced by apomorphine and the test compound is said to have neuroleptic activity if it reduces the gnawing activity in rats; and 5) by the rat conditioned avoidance response methodology of L. Cook and C. Cantania, Effects of Drugs on Avoidance and Escape Behaviour, Federation Proceedings 23 , 818-825, (1964) •1 u t, g g in which rats are administered orally 22.0 mg/kg of the test compound. After administration, if the compound blocks the avoidance response, said compound is said to be a neuroleptic agent.
The compounds are therefore indicated for use as sleep-inducers, minor tranquillisers and neuroleptic agents. An indicated suitable daily dosage is, for sleep-inducing use, from 15 to 750 mg, suitably administered as g single dose at bed-time, for minor tranquilliser use from 10 to 1000 mg, conveniently administered in divided doses of from 2.5 to 500 mg, two to four times daily, or in retard form, and for neuroleptic use from 1 to 1000 mg, conveniently administered in divided doses of from 0.25 to 500 mg, two to four times daily, or In retard form.
The compounds may be admixed vzith conventional pharmaceutically acceptable diluents or carriers, and, optionally, other excipients, and administered in such forms as tablets or capsules.
The compounds may be administered in non salt form or in the form of pharmaceutically acceptable acid or base addition salts, which salt forms possess the same order of activity as the non-salt forms. Suit- 8 43693 able salt forms include mineral acid, such as hydrochloric, hydrobromic or sulphuric acid, salt forms and alkali metal, such as sodium or potassium salt forms.
Preferred compounds of Formula I are those in which 5 Rj is methyl, especially those in which R^ is methyl and R^ is ethyl. Particularly preferred is the compound of Formula I in which R^ is ethyl, R2 is hydrogen ana R^ is methyl, that is, 3-(l-iminopropyl)-4-hydroxy-G-phenyll-methyl-2(IH)-pyridone.
The following Examples illustrate the invention. 43608 EXAMPLE 1 : 3- (1-In-i nopropyl) -i-hyrlroxy-6-phenyl-lingthyl-2 (111) -pyridone a) 3-Ethyl-S-^lbydroxyphenethylteN^methyteisoxazoleil£S£fe£S2i?i-S-l£2SE2HD4_of_foniiula_IV)_ A suspension of 58.5 σ (0.348 mole) of 3-ethylN,5-dimethyl-isoxazols-4-carboxamide in 1 litre of tetrahydrofuran is cooled to -65°C and 478 ml of 1.6M n-butyllithium in hexane (0.765 mole) is added, dropwise while maintaining the temperature between -60° and -7C°C. After addition is complete, tho suspension is stirred for 1 ^/2 hours at -60° to -70DC, and then 37.2 g (0.350 mole) of benzaldehyde in 375 ml. tetrahydrofuran is added, dropwise, while maintaining the temperature between -Cfi and -70°C. After addition is complete, the mixture is stirred for 1 1/2 hours at -60° to -70°C and then warmed to -30°C and quenched by the addition of saturated ammonium chloride solution. The mixture is further diluted with tetrahydrofuran and the layers are separated. The tetrahydrofuran layer is washed twice with 501 brine, and once with brine, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo.
The solid residue is triturated with ether and filtered to give the heading compound, m.p. 135° to 137°C.
Jcomgound_of_formula_III).
A solution of 29.0 g (0.105 mole) of 3-ethyl-5(B-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide and 500 ml of acetic acid, at room temperature, is treated, dropwise, rapidly with 12.5 g (0.125 mole) of chromium trioxide in 125 ml of water. The resulting solution is stirred for 2 hours at room temperature and a portion of the acetic acid is removed in vacuo. The remainder is poured onto ice/water and extracted with methylene chloride. The methylene chloride layer is washed with 2N sodium hydroxide, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo.
The solid residue is triturated with ether and recrystallised from ethanoi to give the heading compound, m.p. 134° to 136°C. c) 1^Ε^)ιγΐ252ΐηβ6Ηγ1-6-ρΗβην1-ΪΞοΧ3Ζθ1ο£4Λ5-ο].ρνΓϊΰίηii 5SizE2®_ Ϊ2Ε2)Ε222έ_2ί _ί 252El5_ ϊϊΐ A mixture of 11.0 g (0.0405 mole) of 3-ethyl-Nmethyl-5-phenacyl-4-isoxazole carboxamide and 120 ml of 2M sulphuric acid is refluxed for 18 hours. The mixture is cooled and extracted with methylene chloride. The methylene chloride layer is washed with water and then brine, dried over anhydrous magnesium sulphate, filtered - 11 4 3 6 3 3 and evaporated in vacuo. The residue is triturated with ether and filtered to give the heading compound, m.p. 167° to 169°C. 4) 3;_tlyTmino2ronyl)-4-hvdroxy26zEhenyl2l;n;ethyly2_(lH).ΕΖΣΐ3£Π£_ΐ£2222Η23-2ί_ί2ΕΞ^ΐ2_£) A mixture of 7.2 g (0.0314 mole) of 3-ethvl-5methyl-6-phenyl-isoxazolof4,5-c]pyridin-4(5H)-one, 160 ml of ethanol and 0.800 g of 10% palladium on carbon is hydrogenated at 50 psi and room temperature. The hydrogenation is ceased after 1 equivalent of hydrogen is absorbed (ca. 4 hours). The mixture is filtered to remove the catalyst and the solvent is removed in vacuo. The residue is crystallised from ether to give the heading compound, m.p. 145° to 147°C.
EXAMPLES 2-9i In manner analogous to Example 1 and employing appropriate starting materials in approximately equivalent amounts, the compounds of formulae I, II, III, IV and V, in which Rj, R?R3 have the significances indicated in the following Table, may be obtained.
*Jt 4# V C* O EX. No.R1R2R3 Melting Point (°C) - Compound I11 ! III - IV 2 cyclohexyl H :ch3 t i 3 c2h5 £-ClCH3 4C2H5e-fCH3 188-189 ί 5 ^2^5 ECH3CII3 '· 6C2H5 £-ch3oCH3 j ί 7C2H5 m-FCH3 1 8 C-H- ' o-F CH. 121.5-124 2 5 3 9C2H5 o-CH3CH3 1

Claims (32)

1. Λ process for the production of a compound of formula I, in which Pj is alkyl of 1 to 4 carbon .atoms or cycloalkyl of 3 to 6 carbon atoms, 5 ? 2 is hydrogen, fluorine, chlorine, or alkyl or alkoxy of 1 to 4 carbon atoms, and 1’ 3 is straight chain alkyl of 1 to 4 carbon atoms, characterised by 10 reducing a compound of formula II, in which Pp R ? and R^ ? - re ; ’ Λ defined above. 14 4 3 598
2. A process for the production of a compound of formula I, stated in Claim 1, substantially as herein described with reference to any one of the Examples
3. A compound of formula I, stated in Claim 1, 5 whenever produced by a process according to Claim 1 or 2.
4. A compound of formula I, stated in Claim 1.
5. A compound of formula I, stated in Claim 1, in which *3 is methyl.
6. A compound of formula I, stated in Claim 1, 10 in which R i is ethyl and R 3 is methyl.
7. A compound of formula I, stated in Claim 1, in which R 1 is ethyl, R^ i s met hyl and Rp is hydrogen.
8. A compound of formula I, stated in Claim 1, in which R 1 is ethyl, Rp is methyl and Rp is para-chloro. 15
9. A compound of formula I, stated in Claim 1, in which R 1 is ethyl, Rp is methyl and Rp is para-fluoro.
10. A compound of formula I, stated in Claim 1, in which R 1 is ethyl, Rp is methyl and Rp is para-methyl.
11. A compound of formula I, stated in Claim 1, 20 in which R 1 is ethyl, Rp is methyl and Rp is para-methoxy
12. A compound of formula I, stated in Claim 1, in which R 1 is ethyl, Rp is methyl and Rp is meta-fluoro.
13. A compound of formula I, stated in Claim 1 in v/hich I'.j is ethyl, R, is methyl and FL is ortho-fluoro.
14. A compound of formula I, stated in Claim 1, in v/hich R^ is ethyl, is methyl and is ortho-methyl.
15. A compound of formula I, stated in Claim. 1, in v/hich R^ is cyclohcxyl, is methyl. R 2 to is any hydrogen end
16. A compound according one of Claims 3 to 15 , in non-salt form.
17. A compound according to any one of Claims 3 to 15 in acid addition salt form.
18. A. compound according to any one of Claims 3 to 15 ir. base addition salt form. IS.
19.A compound according to any one of Claims 3 to 15 in alkali metal salt form.
20. A pharmaceutical composition comprising a compound according to any one of Claims 3 to li, in non salt form or in pharmaceutically acceptable acid or base addition salt form, in association with a pharmaceutically accept.'iblo diluent or carrier. - 16
21. A process for tho production of a compound of formula II, stated in Claim 1, chariictorised by cyclisation of a compound of formula III tl in which R^, R 2 and R^ are as defined in Claim 1, under acid conditions.
22. A process for the production of a compound of formula II, stated in Claim 1, substantially as herein described with-reference to any one of the Examples.
23. A compound of formula II, stated in Claim 1 whenever produced by a process according to Claim 21 or 22.
24. A compound of formula II, stated in Claim 1
25. A process for the production of a compound of formula III, stated in Claim 21, characterised by oxidation of a compound of formula IV O. 17 ί 3 3 D 8 in which R,, R„ and R., arc as defined in Claim 1 1 z 3 under acid conditions and in the presence of water.
26. A process for the production of a compound of formula III, stated in Claim 21, substantially as herein described with reference to any one of the Examples.
27. A compound of formula III, stated in Claim 21, whenever produced by a process according to Claim 25 or 26.
28.S. A compound of formula III, stated in Claim 21.
29. A process for the production of a compound of formula IV, stated in Claim 25, characterised by reaction of a compound of formula V R in which and E., are as defined in Claim 1 with a compound of formula VI oci: R. '2 VI in which R^ is as defined in Claim 1 in an inert organic solvent. diiotm
30. A process for tlie production of a compound of formula IV, stated in Claim 25, substantially as herein described vzith reference to any one of the Examples. I
31. A compound of formula IV, stated in Claim 5 25, whenever produced by a process according to Claim 29 or 30.
32. A compound of formula IV, stated in Claim 25
IE1724/76A 1975-08-06 1976-08-04 3-iminoalkyl-2-(1h)-pyridines IE43698B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US60232475A 1975-08-06 1975-08-06

Publications (2)

Publication Number Publication Date
IE43698L IE43698L (en) 1977-02-06
IE43698B1 true IE43698B1 (en) 1981-05-06

Family

ID=24410893

Family Applications (1)

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Country Status (16)

Country Link
AT (1) ATA579476A (en)
AU (1) AU507216B2 (en)
BE (1) BE844882A (en)
CA (1) CA1064935A (en)
CH (1) CH626077A5 (en)
DE (1) DE2633819A1 (en)
DK (1) DK342876A (en)
ES (1) ES450507A1 (en)
FI (1) FI762152A (en)
FR (2) FR2361886A1 (en)
GB (1) GB1563336A (en)
IE (1) IE43698B1 (en)
NO (1) NO762643L (en)
NZ (1) NZ181683A (en)
PH (1) PH11844A (en)
ZA (1) ZA764732B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2801190A1 (en) * 1977-01-19 1978-07-20 Sandoz Ag 3- (ALPHA-IMINOBENZYL) -4-HYDROXY-2 (1H) - PYRIDONE DERIVATIVE

Also Published As

Publication number Publication date
CH626077A5 (en) 1981-10-30
AU507216B2 (en) 1980-02-07
BE844882A (en) 1977-02-04
FI762152A (en) 1977-02-07
NO762643L (en) 1977-02-08
ATA579476A (en) 1981-06-15
NZ181683A (en) 1979-01-11
DE2633819A1 (en) 1977-02-24
PH11844A (en) 1978-07-21
AU1661276A (en) 1978-02-09
DK342876A (en) 1977-02-07
CA1064935A (en) 1979-10-23
FR2361886A1 (en) 1978-03-17
ES450507A1 (en) 1977-12-16
FR2360585B1 (en) 1980-02-15
GB1563336A (en) 1980-03-26
ZA764732B (en) 1978-03-29
FR2360585A1 (en) 1978-03-03
IE43698L (en) 1977-02-06

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