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WO1997046520A1 - Derives de 4-nitro-2-phenoxysulfonanilides - Google Patents

Derives de 4-nitro-2-phenoxysulfonanilides Download PDF

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Publication number
WO1997046520A1
WO1997046520A1 PCT/JP1997/001867 JP9701867W WO9746520A1 WO 1997046520 A1 WO1997046520 A1 WO 1997046520A1 JP 9701867 W JP9701867 W JP 9701867W WO 9746520 A1 WO9746520 A1 WO 9746520A1
Authority
WO
WIPO (PCT)
Prior art keywords
nitro
phenoxysulfonanilide
inflammatory
analgesic
antipyretic
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/JP1997/001867
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 AU29776/97A priority Critical patent/AU2977697A/en
Publication of WO1997046520A1 publication Critical patent/WO1997046520A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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 sulfonanilide derivatives having anti-inflammatory, analgesic and antipyretic effects.
  • the present inventors have studied for the purpose of providing a compound having an anti-inflammatory, analgesic, and antipyretic effect, and as a result, have found that a certain sulfonanilide derivative achieves the object, and completed the present invention.
  • the present invention provides
  • R represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • n represents an integer of 0 to 8
  • Ph represents a phenyl group.
  • It is a 2-phenoxysulfonylanilide derivative.
  • n force is an integer of 1 to 8, it can be produced by the following synthetic route.
  • Ph represents a phenyl group
  • Boc represents a t-butoxycarbonyl group
  • Et represents an ethyl group, and R has the same meaning as described above. Further, when n is an integer of 1 to 8, it can also be produced by the following synthetic route.
  • the compound of the present invention can be administered orally or parenterally in a conventional dosage form.
  • a conventional dosage form are, for example, tablets, granules, powders, powders, capsules, solutions, emulsions, suspensions, injections and the like, all of which can be produced by a usual method using a conventional carrier.
  • 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. Usually 5 to 100 Omg per day. Industrial applicability
  • the force lagenin paw edema test was carried out according to the method of Winter et al. [Proc. Soc. Ep. Bio. 1. Med., Vol. 111, p. 544 (1962)].
  • a test subject [compound of the present invention] suspended in a 5% aqueous solution of gum arabic was orally administered to a rat of type 1 Wis rats (6 rats per group) at a dose of 1 lm / 100 g body weight.
  • 1% strength lagenin was subcutaneously administered to the left limb foot 0 at 0.1 im 1.
  • Three hours after the administration of force lagenin the paw volume was measured, and its edema inhibition rate was determined to examine its anti-inflammatory effect.
  • the dose of the sample was set to lmg / kg. Table 1 shows the results. Table 1 Specimen Dose Edema suppression rate

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Cette invention concerne des dérivés de 4-nitro-2-phénoxysulfonanilides, lesquels correspondent à la formule générale (I) où R représente un atome d'hydrogène ou un groupe alkyle comportant de un à cinq atomes de carbone, tandis que n représente un nombre entier entre 0 et 8. Ces dérivés possèdent d'excellentes activités anti-inflammatoires, analgésiques et antipyrétiques.
PCT/JP1997/001867 1996-06-04 1997-06-02 Derives de 4-nitro-2-phenoxysulfonanilides Ceased WO1997046520A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29776/97A AU2977697A (en) 1996-06-04 1997-06-02 4-nitro-2-phenoxysulfonanilide derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8/140558 1996-06-04
JP14055896 1996-06-04

Publications (1)

Publication Number Publication Date
WO1997046520A1 true WO1997046520A1 (fr) 1997-12-11

Family

ID=15271482

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/001867 Ceased WO1997046520A1 (fr) 1996-06-04 1997-06-02 Derives de 4-nitro-2-phenoxysulfonanilides

Country Status (2)

Country Link
AU (1) AU2977697A (fr)
WO (1) WO1997046520A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2780009A4 (fr) * 2011-11-17 2015-05-06 Univ Colorado Regents Procédés et compositions pour une administration améliorée de médicament à l' il et formulations d'administration prolongée

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06206859A (ja) * 1992-11-20 1994-07-26 Taisho Pharmaceut Co Ltd Ｎ−アシル−５−アミノスルホンアニリド化合物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06206859A (ja) * 1992-11-20 1994-07-26 Taisho Pharmaceut Co Ltd Ｎ−アシル−５−アミノスルホンアニリド化合物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2780009A4 (fr) * 2011-11-17 2015-05-06 Univ Colorado Regents Procédés et compositions pour une administration améliorée de médicament à l' il et formulations d'administration prolongée
US9562015B2 (en) 2011-11-17 2017-02-07 The Regents Of The University Of Colorado, A Body Methods and compositions for enhanced drug delivery to the eye and extended delivery formulations

Also Published As

Publication number Publication date
AU2977697A (en) 1998-01-05

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