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WO1994016702A1 - Medicament contre l'elimination irreguliere des matieres fecales - Google Patents

Medicament contre l'elimination irreguliere des matieres fecales Download PDF

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Publication number
WO1994016702A1
WO1994016702A1 PCT/JP1994/000096 JP9400096W WO9416702A1 WO 1994016702 A1 WO1994016702 A1 WO 1994016702A1 JP 9400096 W JP9400096 W JP 9400096W WO 9416702 A1 WO9416702 A1 WO 9416702A1
Authority
WO
WIPO (PCT)
Prior art keywords
same
compound
different
formula
lower alkyl
Prior art date
Application number
PCT/JP1994/000096
Other languages
English (en)
Japanese (ja)
Inventor
Atsushi Tomaru
Nobuyuki Kishibayashi
Akio Ishii
Junichi Shimada
Fumio Suzuki
Original Assignee
Kyowa Hakko Kogyo Co., 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 Kyowa Hakko Kogyo Co., Ltd. filed Critical Kyowa Hakko Kogyo Co., Ltd.
Publication of WO1994016702A1 publication Critical patent/WO1994016702A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline

Definitions

  • the present invention relates to a medicine for treating bowel movement abnormality.
  • a compound represented by the following general formula (I) selectively antagonizes the adenosine receptor A receptor, and produces diuretic Sakugawa, renal protection Sakugawa, bronchodilation It is known to have a tonicity-improving action and a brain function-improving action (Japanese Patent Application Laid-Open Nos. 173889/1987 and 4-270222 / 1999).
  • the xanthine-inducing compound contained in the compound (I) has an adenosine antagonistic activity [Naunyn-Schmiedberg ', et al. Archcol.Pharmol.), 33 ⁇ , 59 (1987), Japanese Patent Publication No. 2-247180, Journal of Medicinal 'Chemistry (J. Med.Cem.), 35, 924 and 3066 (1992) ].
  • the compound exerts a defecation function promoting action.
  • compound (I) it is found that a compound in which the 8-position of a xanthine derivative is a lower alkyl has a diuretic effect is described in Journal of Medicinal Chemistry (J.
  • R ′, IT and R : i are the same or different and represent hydrogen or lower alkyl
  • X 1 and X 2 are the same or different and represent oxygen or sulfur
  • Q is lower alkyl
  • R (Wherein, R 'and K' represent-) or represent a different or non-replaced fatty alkyl.] Or a pharmaceutically acceptable salt thereof as an active ingredient And a therapeutic agent for bowel movement disorders.
  • the present invention relates to a method for treating bowel movement disorder, which comprises administering an effective amount of compound (I) or a pharmaceutically acceptable salt thereof to a patient with bowel movement disorder.
  • the present invention also relates to the use of compound (I) or a pharmaceutically acceptable salt thereof for the manufacture of a therapeutic agent for bowel movement disorders.
  • lower alkyl is straight-chain or branched having 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, Neopentyl, hexyl and the like are included.
  • Alkylene includes straight or branched ones having 1 to 4 carbon atoms, for example, methylene, ethylene, trimethylene, tetramethylene, methylmethylene, propylene, ethylethylene and the like.
  • the alicyclic alkyl includes those having 3 to 8 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
  • substituent of the alicyclic alkyl include the same or different substituents having 1 to 3 substituents, for example, lower alkyl, hydroxy, lower alkoxy, halogen, amino, nitro, etc., and alkyl of lower alkyl and lower alcohol.
  • the moiety is the same as the definition of the lower alkyl described above, and the halogen includes atoms of fluorine, chlorine, bromine, and iodine.
  • the pharmaceutically acceptable salts of compound (I) include pharmaceutically acceptable acid addition salts, metal salts, ammonium salts, organic amine addition salts, amino acid addition salts and the like.
  • Pharmaceutically acceptable acid addition salts of compound (I) include inorganic acid salts such as hydrochloride, sulfate and phosphate, acetate, maleate, fumarate, tartrate, citrate and the like.
  • Metal salts that are pharmacologically acceptable include alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as magnesium salts and calcium salts, aluminum salts, zinc salts and the like.
  • Ammonium salts include salts such as ammonium and tetramethylammonium.
  • Pharmaceutically acceptable organic amine addition salts include addition salts such as morpholine and piperidine, and pharmaceutically acceptable amino acid additions. Examples of the salt include addition salts of lysine, glycine, phenylalanine and the like.
  • the therapeutic agent for constipation abnormality of the present invention includes, for example, functional constipation [acute constipation or chronic constipation (relaxation). J or organ stool ⁇ inevitable cfei, tumor-, ulcerative, inflammatory scarring or vertebral injury, etc. ), Intestinal paralytic ileus (postoperative intestinal paralysis, appendectomy, hernia operation, gastrectomy or gallstone extraction, etc.), irritable bowel syndrome, various congenital gastrointestinal dysfunction or pseudo-intestinal obstruction (idiopathic) It can be used as an agent for eliminating intestinal contents during gastrointestinal examination or before and after surgery and for assisting defecation after surgery.
  • Compound (I) can be obtained by a known production method [Journal of Medicinal Chemistry (J. Med. Chem.), 35, 924 (1992)].
  • Table 1 shows examples of specific compounds used as therapeutic agents for bowel movement disorders of the present invention.
  • Table 2 shows the physicochemical properties of the compounds in Table 1.
  • Compound Melting point (° c) Molecular formula IR (KBr) (cm 1 )
  • Test example 1 Acute toxicity test
  • Test compounds were administered orally (OOnigZkg) using three dd male mice weighing 20 ⁇ lg per group. After the administration, the mortality was observed 7 times later, and the minimum lethal dose (MLD) value was determined.
  • MLD minimum lethal dose
  • the MLD is> 300 ing Zkg, and it is safe to use over a wide dose range with low toxicity.
  • CMC carboxymethylcellulose
  • test compound (0.0003 to 10 mg / kg) was orally administered in an amount of 0.5 ml per 250 g of rat weight, and the control group was orally administered a 0.33 ⁇ 4CMC solution in an amount of 0.5 ml orally per 250 g rat weight.
  • Feces excreted 3 hours after administration of the test compound were collected, and the wet weight was measured. After drying the collected feces at 100 ° C for 6 hours, the dry weight was measured, and the moisture content was calculated from the wet weight and dry weight according to the following formula. Since there was no change, the wet weight was used as the amount of defecation.
  • Moisture content (%) (wet weight-dry weight) Z (wet weight) X 100
  • the significant difference test for defecation volume was determined using the Kruska Wallis test between the control group and the test compound administration group, after confirming that there was a difference in the mean value of each group, and then using Steel's multiple comparison test. Performed c When the risk rate was less than 5 (p ⁇ 0.05), there was a significant difference, and the lowest dose with a significant difference was defined as the minimum effective dose (MED).
  • MED minimum effective dose
  • Table 3 shows the results. Third compound number MED (mg / kg, oral)
  • Compound (I) or a pharmaceutically acceptable salt thereof can be used as it is or in various pharmaceutical forms.
  • the pharmaceutical composition of the present invention can be produced by uniformly mixing an effective amount of compound (I) or a pharmaceutically acceptable salt thereof with a pharmaceutically acceptable carrier as an active ingredient.
  • These pharmaceutical compositions are desirably in a unit dosage form suitable for parenteral administration orally or as a formulation by injection or rectal administration.
  • any useful pharmacologically acceptable carrier can be used.
  • Oral liquid preparations such as suspensions and syrups include water, sugars such as sucrose, sorbitol, fructose, glycols such as polyethylene glycol, propylene glycol, sesame oil, olive shine, soybean oil And oils such as p-hydroxybenzoic acid esters, etc., and fringes such as strobe leaf wrappers and peppermint.
  • excipients such as lactose, glucose, sucrose, mannitol, disintegrants such as starch and sodium alginate, lubricants such as magnesium stearate and talc
  • a binder such as polyvinyl alcohol, hydroxypropyl cellulose, gelatin, a surfactant such as a fatty acid ester, and a plasticizer such as glycerin. Tablets and capsules are the most useful unitary oral dosage forms because of their ease of administration.
  • solid pharmaceutical carriers are used.
  • the injection can be prepared using a carrier consisting of distilled water, a salt solution, a glucose solution or a mixture of a salt solution and a glucose solution. At this time, it is prepared as a solution, suspension or dispersion using an appropriate solubilizing agent according to a conventional method. .
  • Formulations by rectal administration are preferably dissolved in a pharmaceutically acceptable carrier, such as a pH adjuster, base, disintegrant, excipient, diluent, coloring agent, fragrance, softener, wetting agent, etc. It can be prepared by uniformly dispersing or dissolving in the preparation together with adjuvants.
  • a pharmaceutically acceptable carrier such as a pH adjuster, base, disintegrant, excipient, diluent, coloring agent, fragrance, softener, wetting agent, etc. It can be prepared by uniformly dispersing or dissolving in the preparation together with adjuvants.
  • pH regulators are usually used for pharmaceuticals, and maintain the pH of the rectal fluid at 4.0 to 8.0 after administration of the preparation.
  • succinic acid-borax lactic acid-sodium lactate, Potassium monocitrate-sodium hydroxide, sodium dicitrate-sodium hydroxide, potassium phosphate monobasic-sodium phosphate, potassium phosphate monobasic-borax and the like.
  • the base may be an oily base or a water-soluble base that is commonly used.
  • Examples of the oily base include cocoa butter, Rakkasi oil, coconut oil, vegetable oils such as corn oil, Hadofuatsu Bok glycerol esters of saturated fatty acids of natural fatty acids as a raw material (Uitepu zone Ichiru 'M: Dainamai Tonoberu (Pharmasol 1 M : manufactured by NOF Corporation) and mineral oils such as serine and paraffin.
  • Examples of the water-soluble base include a polyethylene glycol-polypropylene glycol copolymer, propylene glycol, glycerin and the like. These bases can be used alone or in combination.
  • Examples of the dosage form of the preparation include a rectal suppository of IS1 at room temperature or a soft capsule prepared by filling a liquid or soft substance into a capsule.
  • Compound (I) or a pharmacologically acceptable salt thereof can be administered orally in the above-mentioned pharmaceutical form or parenterally as a preparation by injection or rectal administration.
  • the dosage is usually 1 to 50 mg / kg, divided into 3 to 4 times per day, depending on the dosage form, patient age, body weight, symptoms, etc.
  • a tablet having the following composition was prepared by a conventional method.
  • Fine granules having the following composition were prepared by a conventional method.
  • a forcepsel having the following composition was prepared by a conventional method.
  • An injection having the following composition was prepared by a conventional method.
  • a formulation for rectal administration having the following composition was prepared by a conventional method.
  • Witebzole 1 M H 15 manufactured by Dynamite Nobel
  • 290.9 g of Witepzol TM E75 manufactured by Dynamite Nobel
  • 2.5 g of Compound A, 13.6 g of potassium monophosphate and 14.2 g of sodium diphosphate were uniformly mixed and dispersed therein. The mixture was dispersed and filled into a plastic suppository mold, and then gradually cooled to obtain a rectal suppository (containing 2.5 mg of active ingredient per preparation).
  • a tablet having the following composition was prepared by a conventional method.
  • Compound Flg was dissolved in purified soy lOOg, and purified egg yolk lecithin 12 g and glycerin for injection 25 g were added. This mixture was kneaded and emulsified in a conventional manner to 1000 ml with distilled water for injection. The resulting dispersion was aseptically filtered using a 0.2 im disposable membrane filter, and then aseptically filled into glass vials in 2 ml increments for injection (containing 2 mg of active ingredient per vial). To).
  • a formulation for rectal administration having the following composition was prepared by a conventional method.
  • the Witepuzo Ichiru ⁇ ⁇ ⁇ (manufactured Dainamai Tonoichi Bell) 1 5 678. 8g and Witebuzoru ⁇ ⁇ 7 5 (Dainamai Tonoberu Co.) 290. 9 g were melted at 40 to 50 ° C.
  • the mixed and dispersed product was filled in a plastic suppository mold, and then gradually cooled to obtain a rectal suppository (containing 2.5 mg of active ingredient per preparation).
  • a formulation for rectal administration having the following composition was prepared by a conventional method.
  • Formulation Compound B 2.5 mg
  • a formulation for rectal administration having the following composition was prepared by a conventional method.
  • a formulation for rectal administration having the following composition was prepared by a conventional method.
  • Formulation compound X 2. ⁇ mg
  • a formulation for rectal administration having the following composition was prepared by a conventional method.
  • the Witepuzo Ichiru 'Micromax Eta (manufactured Dainamai Tonoichi Bell) 1 5 678. 8g and Witebuzoru (manufactured Dainamai Bok Nobel) 1 M E 7 5 290. 9g melted at 40 to 50 ° C.
  • 2.5 g of Compound AG, 13.6 g of potassium monophosphate and 14.2 g of sodium diphosphate were uniformly mixed and dispersed therein. The mixture was dispersed and filled into a plastic suppository mold, and then gradually cooled to obtain a rectal suppository (containing 2.5 mg of active ingredient per preparation).
  • a formulation for rectal administration having the following composition was prepared by a conventional method.
  • Formulation compound All 2.5 mg
  • a therapeutic agent for bowel movement disorder is provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Médicament contre l'élimination irrégulière des matières fécales, contenant, comme principe actif, un dérivé de xanthine représenté par la formule générale (I) ou un sel pharmaceutiquement acceptable de ce dérivé, formule dans laquelle R?1, R2 et R3¿ représentent chacun hydrogène ou alkyle inférieur; X1 et X2 représentent chacun oxygène ou soufre; et Q représente alkyle inférieur ou un groupe représenté par (a), (b), (c), (d) ou (e), Z1 et Z2 représentant chacun hydrogène ou étant combinés pour représenter oxygène; Y représentant une liaison simple ou alkylène; n valant 0 ou 1; le symbole .^_.^_.^_ représentant une liaison simple ou double; et R4 et R5 représentant chacun cycloalkyle (non)substitué.
PCT/JP1994/000096 1993-01-26 1994-01-25 Medicament contre l'elimination irreguliere des matieres fecales WO1994016702A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1088693 1993-01-26
JP5/10886 1993-01-26

Publications (1)

Publication Number Publication Date
WO1994016702A1 true WO1994016702A1 (fr) 1994-08-04

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995011904A1 (fr) * 1993-10-28 1995-05-04 University Of Florida Research Foundation, Inc. Nouveaux agonistes et antagonistes de recepteurs de l'adenosine a¿1?
WO1998005334A1 (fr) * 1996-08-07 1998-02-12 Kyowa Hakko Kogyo Co., Ltd. Emulsion grasse contenant un derive de xanthine
US5736528A (en) * 1993-10-28 1998-04-07 University Of Florida Research Foundation, Inc. N6 -(epoxynorborn-2-yl) adenosines as A1 adenosine receptor agonists
US5789416A (en) * 1996-08-27 1998-08-04 Cv Therapeutics N6 mono heterocyclic substituted adenosine derivatives
WO1999054331A1 (fr) * 1998-04-16 1999-10-28 Boehringer Ingelheim Pharma Kg Nouveaux derives de xanthine a substitution asymetrique, leur procede de preparation et leur utilisation comme medicaments a effet antagoniste de l'adenosine
WO2001034610A1 (fr) * 1999-11-12 2001-05-17 Biogen, Inc. Polycycloalkylpurines comme antagonistes du recepteur d'adenosine
WO2001080893A1 (fr) * 2000-04-26 2001-11-01 Eisai Co., Ltd. Compositions medicinales favorisant les mouvements intestinaux
US6576619B2 (en) 1999-05-24 2003-06-10 Cv Therapeutics, Inc. Orally active A1 adenosine receptor agonists
US6605600B1 (en) 1999-11-12 2003-08-12 Biogen, Incorporated Adenosine receptor antagonists and methods of making and using the same
US7160892B2 (en) 2001-10-22 2007-01-09 Eisai Co., Ltd. Pyrimidone compounds and pharmaceutical compositions containing the same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03173889A (ja) * 1989-09-01 1991-07-29 Kyowa Hakko Kogyo Co Ltd キサンチン誘導体

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03173889A (ja) * 1989-09-01 1991-07-29 Kyowa Hakko Kogyo Co Ltd キサンチン誘導体

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995011904A1 (fr) * 1993-10-28 1995-05-04 University Of Florida Research Foundation, Inc. Nouveaux agonistes et antagonistes de recepteurs de l'adenosine a¿1?
US5631260A (en) * 1993-10-28 1997-05-20 University Of Florida Research Foundation, Inc. Xanthine epoxides as A1 adenosine receptor agonists and antagonists
US5668139A (en) * 1993-10-28 1997-09-16 University Of Flordia Research Foundation, Inc. A1 adenosine receptor agonists and antagonists
US5736528A (en) * 1993-10-28 1998-04-07 University Of Florida Research Foundation, Inc. N6 -(epoxynorborn-2-yl) adenosines as A1 adenosine receptor agonists
US5998387A (en) * 1993-10-28 1999-12-07 University Of Florida Research Foundation, Inc. Method for using A1 adenosine receptor agonists
WO1998005334A1 (fr) * 1996-08-07 1998-02-12 Kyowa Hakko Kogyo Co., Ltd. Emulsion grasse contenant un derive de xanthine
US6210687B1 (en) 1996-08-07 2001-04-03 Kyowa Hakko Kogyo Co., Ltd. Fat emulsion containing xanthine derivative
JP2008231117A (ja) * 1996-08-07 2008-10-02 Kyowa Hakko Kogyo Co Ltd キサンチン誘導体含有脂肪乳剤
US5789416A (en) * 1996-08-27 1998-08-04 Cv Therapeutics N6 mono heterocyclic substituted adenosine derivatives
WO1999054331A1 (fr) * 1998-04-16 1999-10-28 Boehringer Ingelheim Pharma Kg Nouveaux derives de xanthine a substitution asymetrique, leur procede de preparation et leur utilisation comme medicaments a effet antagoniste de l'adenosine
US6576619B2 (en) 1999-05-24 2003-06-10 Cv Therapeutics, Inc. Orally active A1 adenosine receptor agonists
EP2070930A1 (fr) * 1999-11-12 2009-06-17 Biogen Idec MA, Inc. Polycycloalkylpurines comme antagonistes du récepteur de l'adénosine
US6605600B1 (en) 1999-11-12 2003-08-12 Biogen, Incorporated Adenosine receptor antagonists and methods of making and using the same
US6649600B1 (en) 1999-11-12 2003-11-18 Biogen, Inc. Adenosine receptor antagonists and methods of making and using the same
WO2001034610A1 (fr) * 1999-11-12 2001-05-17 Biogen, Inc. Polycycloalkylpurines comme antagonistes du recepteur d'adenosine
JP2003513982A (ja) * 1999-11-12 2003-04-15 バイオジェン インコーポレイテッド アデノシンレセプターアンタゴニストとしてのポリシクロアルキルプリン
US7579354B2 (en) 1999-11-12 2009-08-25 Kiesman William F Adenosine receptor antagonists and methods of making and using the same
BG65720B1 (bg) * 1999-11-12 2009-08-31 Biogen, Inc. Полициклоалкилпурини, антагонисти на аденозин рецептор
EP2305684A1 (fr) * 1999-11-12 2011-04-06 Biogen Idec MA Inc. Polycycloalkylpurines comme antagonistes du recepteur de l'adenosine
WO2001080893A1 (fr) * 2000-04-26 2001-11-01 Eisai Co., Ltd. Compositions medicinales favorisant les mouvements intestinaux
US7189717B2 (en) 2000-04-26 2007-03-13 Eisai Co., Ltd. Medicinal compositions promoting bowel movement
EP1510222A3 (fr) * 2000-04-26 2007-05-23 Eisai R&D Management Co., Ltd. Compositions medicinales favorisant les mouvements intestinaux
KR100782091B1 (ko) * 2000-04-26 2007-12-04 에자이 알앤드디 매니지먼트 가부시키가이샤 배변을 촉진하는 의약 조성물
US7160892B2 (en) 2001-10-22 2007-01-09 Eisai Co., Ltd. Pyrimidone compounds and pharmaceutical compositions containing the same

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