GB1272906A - Quinoxalinecarboxamide anti inflammatory agents - Google Patents

Quinoxalinecarboxamide anti inflammatory agents

Info

Publication number
GB1272906A
GB1272906A GB34658/70A GB3465870A GB1272906A GB 1272906 A GB1272906 A GB 1272906A GB 34658/70 A GB34658/70 A GB 34658/70A GB 3465870 A GB3465870 A GB 3465870A GB 1272906 A GB1272906 A GB 1272906A
Authority
GB
United Kingdom
Prior art keywords
oxo
tetrahydro
ethyl
reacting
alkyl
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.)
Expired
Application number
GB34658/70A
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.)
Pfizer Inc
Original Assignee
Pfizer Inc
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 Pfizer Inc filed Critical Pfizer Inc
Publication of GB1272906A publication Critical patent/GB1272906A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring

Landscapes

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

Abstract

1,272,906. Quinoxalinecarboxamides. PFIZER Inc. 17 July, 1970 [15 Oct., 1969], No. 34658/70. Heading C2C. Novel quinoxaline carboxamides of the Formula IV and the basic metal salts thereof, wherein R 1 and R 2 are H, C 1-3 alkyl, C 2-4 alkenyl, C 3-6 cycloalkyl, phenyl or phenyl substituted by F, Cl, Br, C 1-2 alkoxy, or C 1-3 alkyl; and R 5 is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, pyridyl, pyridyl substituted by 1 or 2 CH 3 radicals, thiazolyl, phenyl, benzyl or mono- or disubstituted phenyl or benzyl, said substituents being F, C1, Br, C 1-3 alkyl, C 1-2 alkoxy, C 1-2 alkylthio, OH, NH 2 , C 1-3 alkylamino, CF 3 or OCF 3 ; are prepared by reacting C 1-3 alkyl esters of the appropriate 1,2,3,4-tetrahydro-3-oxo-2- quinoxaline carboxylic acids with amines of the formula or by reacting compounds of the above Formula IV in which the radical R 3 CO- is replaced by a hydrogen atom with anhydrides of the formula 3,4 - Dihydro - 2<SP>1</SP>,5<SP>1</SP> - difluoro - 3 - oxo - 2- quinoxaline-carboxanilide is obtained by reacting 2,5 - difluoroaniline with ethyl 3,4 - dihydro- 3 - oxo - 2 - quinoxaline - carboxylate resulting from the reaction o-phenylenediamine and diethyl bromomalonate or diethyl oxo-malonate. Ethyl 1,2,3,4 - tetrahydro - 1 - acetyl - 3 - oxo- 2-quinoxalinecarboxylate is made by reacting acetic anhydride with ethyl 1,2,3,4-tetrahydro-3- oxo - 2 - quinoxalinecarboxylate obtained by hydrogenating ethyl 3,4-dihydro-3-oxo-2-quinoxalinecarboxylate. 1,2,3,4 - Tetrahydro - 2<SP>1</SP>,5<SP>1</SP> - difluoro - 3 - oxo- 2-quinoxalinecarboxanilide is prepared by reacting 2,5-difluoroaniline with ethyl 1,2,3,4-tetrahydro-3-oxo-2-quinoxalinecarboxylate. Pharmaceutical compositions, having antiinflammatory activity and suitable for oral or parenteral administration, contain the above novel compounds or pharmaceutically acceptable salts thereof and carriers therefor.
GB34658/70A 1969-10-15 1970-07-17 Quinoxalinecarboxamide anti inflammatory agents Expired GB1272906A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US86673269A 1969-10-15 1969-10-15

Publications (1)

Publication Number Publication Date
GB1272906A true GB1272906A (en) 1972-05-03

Family

ID=25348279

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34658/70A Expired GB1272906A (en) 1969-10-15 1970-07-17 Quinoxalinecarboxamide anti inflammatory agents

Country Status (2)

Country Link
US (1) US3654275A (en)
GB (1) GB1272906A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PH15791A (en) * 1978-10-20 1983-03-25 Lilly Co Eli Pharmaceutical composition containing 3,4-dihydro-3-oxoquinoxalines
US6369057B1 (en) 1991-04-15 2002-04-09 Aventis Pharma Deutschland Gmbh Quinoxalines, processes for their preparation and their use
JP2005530753A (en) * 2002-05-03 2005-10-13 エラン ファーマシューティカルズ，インコーポレイテッド Sulfonylquinoxaloneacetamide derivatives and related compounds as bradykinin antagonists
WO2004033436A1 (en) * 2002-10-10 2004-04-22 Elan Pharmaceuticals Inc Sulfonylbenzodiazepinone acetamides as bradykinin antagonists
EP1572678A4 (en) * 2002-12-19 2008-05-07 Elan Pharm Inc Substituted n-phenyl sulfonamide bradykinin antagonists
ES2314418T3 (en) * 2003-05-02 2009-03-16 Elan Pharmaceuticals, Inc. DERIVATIVES OF AMIDAS OF THE ACID 4-BROMO-5- (2-CHLOROBENZOYLAMINE) -1H-PIRAZOL-3-CARBOXYCLIC AND RELATED COMPOUNDS AS ANTIGONISTS OF THE B1 BRADIQUININE RECEPTOR FOR THE TREATMENT OF INFLAMMATORY DISEASES.
CA2524274A1 (en) * 2003-05-02 2004-11-18 Elan Pharmaceuticals, Inc. 4-bromo-5-(2-chloro-benzoylamino)-1h-pyrazole-3-carboxylic acid (1-(aminocarbonyl)eth-1-yl) amide derivatives and related compounds as bradykinin b1 receptor antagonists for the treatment of inflammatory diseases
US20070123531A1 (en) * 2003-05-02 2007-05-31 Elan Pharmaceuticals, Inc. 4-Bromo-5-(2-chloro-benzoylamino)-1h-pyrazole-3-carboxylic acid (phenyl) amide derivatives and related compounds as bradykinin b1 receptor antagonists for the treatment of inflammatory diseases

Also Published As

Publication number Publication date
US3654275A (en) 1972-04-04

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee