American Home Products Corporation

American Home Products Corpooration

Dominick Mobilio

Leslie G Humber

Christopher A Demerson

Philip Floyd Hughes

John H Musser

Joseph P Sabatucci

Eckhardt S Ferdinandi

Albert J Molinari

Derivatives of 4-anilinoquinoline having the formula: ##STR1## where X is O or H.sub.2 and Z is 1-substituted-4-piperidinylamino or diloweralkylaminoloweralkyl inhibit binding of tritiated bradykinin to guinea pig ileum and inhibit bradykinin-induced writhing in mice. Bradykinin is a nonapeptide formed in plasma as a result of inflammation or injury and produces pain when it binds with pain receptors. A drug which inhibits the binding of bradykinin therefore has analgetic properties.

Derivatives of 4-anilinoquinoline-3-carboxamide as analgesic agents

There are disclosed compounds of the formula ##STR1## wherein R is hydrogen, halo or trifluoromethyl;

N-substituted aminoquinolines as analgesic agents

This invention relates to novel quinolinyl- and naphthalenylbenzamides or benylamines and related disclosed compounds of the formula ##STR1## wherein X is nitrogen, NO or CR.sup.1 ; Y is C(R.sup.1)(R.sup.2)O, OC(R.sup.1)(R.sup.2), C(R.sup.1)(R.sup.2)N(R.sup.3), N(R.sup.3)C(R.sup.1)(R.sup.2) or C(R.sup.1).dbd.C(R.sup.2); wherein R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen or lower alkyl containing 1 to 10 carbon atoms; Z is oxygen or (R.sup.1)(R.sup.2); R.sup.4 is R.sup.1, benzyl, benzyl ring substituted with R.sup.5, benzyl alpha monosubstituted with R.sup.1, benzyl ring substituted with R.sup.5 and alpha monosubstituted with R.sup.1, phenyl, phenylalkyl containing 2 to 10 carbon atoms in the alkyl group or phenylalkyl ring substituted with R.sup.5 and containing 2 to 10 carbon atoms in the alkyl group; wherein R.sup.5 is R.sup.1, lower alkoxy containing 1 to 10 carbon atoms, halogen, trihalomethyl, NO.sub.2, N(R.sup.1)(R.sup.2) or C(O)N(R.sup.1)(R.sup.2); R.sup.6 is R.sup.1 or R.sup.6 is C(O)(R.sup.7) with the proviso that Z is not oxygen; and wherein R.sup.7 is R.sup.1, phenyl, perfluoroalkyl containing 1 to 10 carbon atoms, phenylalkyl containing 1 to 10 carbon atoms in the alkyl group; or a pharmaceutically acceptable acid addition salt thereof, and their use in the treatment of pain mediated by the biological peptide, bradykinin. In particular, the preferred compounds are where X is nitrogen, and Y is CH.sub.2 O of the above structure.

Substituted quinolinyl- and naphthalenylbenzamides or benzylamines and

Substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid derivatives and methods for their preparation and use are disclosed. The compounds are useful anti-inflammatory agents.

Preparation of 2,3,4,9-tetrahydro-1H-carbazole acetic acid derivatives

Substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid derivatives and methods for their preparation and use are disclosed. The compounds are useful analgesic, anti-inflammatory, anti-asthmatic and anti-allergic agents.

Substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid derivatives,

2,3,4,9-tetrahydro-1H-carbazole acetic acid derivatives, composition and

Process for the production of substituted 2-oxocyclohexaneacetic acid esters and intermediates used for their production. The substituted 2-oxocyclohexaneacetic acid esters are themselves useful intermediates for the manufacture of substituted 2,3,4,9-tetrahydro-1H-carabazole-1-acetic acid derivatives having useful analgesic and anti-inflammatory activity.

Process for the production of substituted 2-oxocyclohexaneacetic acid

Substituted fused tetrahydrocarbazole acetic acid derivatives and methods for their preparation and use are disclosed. The compounds are useful analgesic and anti-inflammatory agents.

Process for the preparation of substituted fused tetrahydrocarbazole

Substituted fused tetrahydrocarbazole acetic acid derivatives and methods for their preparation and use are disclosed. The compouns are useful analgesic and anti-inflammatory agents.

Susbtituted fused tetrahydrocarbazole acetic acid derivatives

Process for the production of substituted 2-oxocyclohexaneacetic acid esters and intermediates used for their production. The substituted 2-oxocyclohexaneacetic acid esters are themselves useful intermediates for the manufacture of substituted 2,34,9-tetrahydro-1H-carbazole-1-acetic acid derivatives having useful analgesic and anti-inflammatory activity.

Substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid derivatives and methods for their preparation and use are disclosed. The compounds are useful analgesic and anti-inflammatory agents.

Production of substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid

Substituted fused tetrahydrocarbazole acetic acid derivatives,

Substituted 2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid derivatives and methods of their preparation and use are disclosed. The compounds are useful analgesic and anti-inflammatory agents.

Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1 and 4. The nucleus may be optionally substituted at position 8. The derivatives are useful anti-inflammatory and analgesic agents and methods and chemical intermediates for their preparation are also disclosed.

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Franklin Park, NJ, United States of America

Dominick Mobilio