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WO1997047594A1 - Derives de 4-nitrosulfonanilide - Google Patents

Derives de 4-nitrosulfonanilide Download PDF

Info

Publication number
WO1997047594A1
WO1997047594A1 PCT/JP1997/002002 JP9702002W WO9747594A1 WO 1997047594 A1 WO1997047594 A1 WO 1997047594A1 JP 9702002 W JP9702002 W JP 9702002W WO 9747594 A1 WO9747594 A1 WO 9747594A1
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutically acceptable
acceptable salt
derivative
antipyretic
inflammatory
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/JP1997/002002
Other languages
English (en)
Japanese (ja)
Inventor
Kensei Yoshikawa
Masahiro Hasegawa
Masatoshi Suzuki
Youichi Shimazaki
Mariko Ohtani
Shiuji Saito
Masami Goi
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.)
Taisho Pharmaceutical Co Ltd
Original Assignee
Taisho Pharmaceutical 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 Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd
Priority to AU31056/97A priority Critical patent/AU3105697A/en
Publication of WO1997047594A1 publication Critical patent/WO1997047594A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/55—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51—Y being a hydrogen or a carbon atom

Definitions

  • the present invention relates to a 4--2-torosulfonanilide derivative having an anti-inflammatory action, antipyretic action and analgesic action.
  • the present inventors have conducted intensive studies with the aim of providing a compound having an excellent anti-inflammatory action, antipyretic action and analgesic action, and as a result, the following 41-2 trosulfonanilide derivatives represented by We have found that we can achieve this and completed the present invention.
  • the present invention provides
  • n represents an integer of 0 to 8
  • X represents an oxygen atom or a sulfur atom
  • R ′ represents an alkyl group having 5 to 5 carbon atoms
  • R 2 represents a 3 to 8 carbon atom
  • R 3 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Or a pharmaceutically acceptable salt thereof.
  • the alkyl group having 1 to 5 carbon atoms includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, and the like. Examples thereof include a methyl group, an ethyl group, a propyl group and an isopropyl group.
  • the cycloalkyl group having 3 to 8 carbon atoms includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like, and cyclopentyl is preferred. And a cyclohexyl group or a cycloheptyl group.
  • Salts are salts with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid, or acetic acid, propionic acid, succinic acid, fumaric acid, maleic acid, benzoic acid, and fluoric acid It is a salt with organic acids such as, carboxylic acid, glycolic acid, lactic acid, linoleic acid, tartaric acid, citric acid, methanesulfonic acid, and p-toluenesulfonic acid.
  • the compound of the present invention can be produced, for example, by the following reaction route.
  • n is an integer of 1 to 8.
  • E t represents an ethyl group
  • R ′ and RR 3 have the same meanings as described above.
  • n 1 in equation (1), it can also be manufactured by the following method.
  • the compounds of the present invention can be administered orally or parenterally in conventional dosage forms. These include, for example, tablets, granules, powders, capsules, solutions, emulsions, suspensions, and injections, all of which can be produced by a usual method.
  • dosage forms include, for example, tablets, granules, powders, capsules, solutions, emulsions, suspensions, and injections, all of which can be produced by a usual method.
  • the dosage When used as an anti-inflammatory, antipyretic or analgesic in humans, the dosage varies depending on age, body weight, symptoms, route of administration, number of administrations, etc. mg Z days.
  • the compounds of the present invention exhibit excellent anti-inflammatory, antipyretic and analgesic effects, and are useful as anti-inflammatory, antipyretic or analgesic agents because they have few side effects such as gastrointestinal disorders.
  • Example 1 Example 1
  • reaction solution is concentrated, water is added, and the mixture is extracted with ethyl acetate.
  • organic layer is washed successively with a saturated aqueous solution of sodium hydrogen carbonate, a 5% aqueous solution of citric acid, and a saturated saline solution, and dried over anhydrous sodium sulfate. After concentration.
  • N- (2-cyclohexyloxy-141-trophenyl) methanesulfonamide 1 Add 0.9 g of chlorosulfonyl isocynate to a solution of 12 g of tetrahydrofuran containing 1 Og under ice-cooling. After stirring at room temperature for 4 hours, 6.5 ml of acetic acid and 6.5 ml of water were added, and the mixture was further stirred for 15 hours. The reaction solution was poured into water and extracted with ethyl acetate.
  • the force lagenin foot edema test is based on the method of Winter et al. [Proc. Soc. Exp. Biol. Med., Vol. 11, pp. 544 (1962)]. I went. Specimens (compounds 1 and 2) suspended in a 5% aqueous solution of gum arabic were orally administered to Wistar rats (6 per group) at a dose of 1 ml per 100 g body weight. . One hour later, 0.1 ml of 1% strength lagenin was subcutaneously administered to the left foot of the foot. Three hours after administration of force lagenin, paw volume was measured, and its edema inhibition rate was determined to examine anti-inflammatory effects. The dose of the sample was 1 mg / kg / kg.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention se rapporte à des composés représentés par la formule générale (I) ou à des sels pharmaceutiquement acceptables de ces composés. Dans la formule (I), n est un entier compris entre 0 et 5, X représente l'oxygène ou le soufre, R1 représente l'hydrogène ou un alkyle C¿1-5, R?2 représente un alkyle C¿1-5 et R?3 représente un cycloalkyle C¿3-8?. Ces dérivés de 4-nitrosulfonanilide et leurs sels n'entraînent que peu d'effets secondaires tels que des troubles digestifs, ils peuvent faire l'objet d'une administration prolongée, offrent un haut degré de sécurité et ont, entre autres, des effets anti-inflammatoires, antipyrétiques et analgésiques.
PCT/JP1997/002002 1996-06-13 1997-06-11 Derives de 4-nitrosulfonanilide Ceased WO1997047594A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU31056/97A AU3105697A (en) 1996-06-13 1997-06-11 4-nitrosulfonanilide derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/151972 1996-06-13
JP15197296 1996-06-13

Publications (1)

Publication Number Publication Date
WO1997047594A1 true WO1997047594A1 (fr) 1997-12-18

Family

ID=15530255

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/002002 Ceased WO1997047594A1 (fr) 1996-06-13 1997-06-11 Derives de 4-nitrosulfonanilide

Country Status (2)

Country Link
AU (1) AU3105697A (fr)
WO (1) WO1997047594A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4942640A (fr) * 1972-07-03 1974-04-22
JPH0495057A (ja) * 1990-08-08 1992-03-27 Taisho Pharmaceut Co Ltd Ｎ―置換スルホンアニリド化合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4942640A (fr) * 1972-07-03 1974-04-22
JPH0495057A (ja) * 1990-08-08 1992-03-27 Taisho Pharmaceut Co Ltd Ｎ―置換スルホンアニリド化合物

Also Published As

Publication number Publication date
AU3105697A (en) 1998-01-07

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