Ayerst, Mckenna & Harrison, Inc.

American Home Products Corporation

Ivo L Jirkovsky

Leslie G Humber

Christopher A Demerson

Thomas A Dobson

Adolf H Philipp

Andre A Asselin

Jean A Gauthier

George Santroch

Rene Martel

Mitchell N Cayen

Dushan Dvornik

Adolph H Philipp

A compound of the formula ##STR1## in which R.sup.1 is hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl;

[2-(1H-indol-1-yl)ethyl]-2-piperazine and pyrido[1,2-a]indol-9-one as

The invention discloses novel 4H-imidazo[2,3-c]pyrido[2,3-e][1,4]oxazine derivatives, processes for their preparation, pharmaceutical compositions thereof and methods for using the compounds. The compounds of this invention are useful in the treatment of anaphylactic reactions and allergic conditions in a mammal.

4H-Imidazo[2,3-c]pyrido[2,3-e][1,4]oxazine derivatives

Herein is disclosed pyrazino[2',3'-3,4]pyrido[1,2-a]indole derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for treating hypertension in a mammal.

Pyrazino[2',3'-3,4]pyrido[1,2-a]indole derivatives

Herein is disclosed 2H-benzothieno[3,2-c]pyrazol-3-amine derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for producing analgesia in a mammal. In addition, some of the derivatives are useful for inhibiting gastric acid secretion, convulsions, anxiety and aggression, and producing muscle relaxation, hypnosis and sedation in a mammal.

Analgesic compositions consisting of

Herein is disclosed benzofuro[3,2-c]pyrazol-3-amine derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for producing analgesia in a mammal. In addition, some of the derivatives are useful for inhibiting gastric acid secretion, convulsions, anxiety and aggression, and producing muscle relaxation, hypnosis and sedation in a mammal.

Benzofuro[3,2-c]pyrazol-3-amine derivatives

Pyrimido[1,6-a]indole derivatives characterized by having a substituted ethyl group at position 5 and optionally being further substituted at various positions on the pyrimido[1,6-a]indole nucleus are disclosed. The foregoing compounds are useful as antihypertensive agents in a mammal. Methods for their preparation also are disclosed.

Pyrimido[1,6-a]indole derivatives

1,4,5,6-Tetrahydropyrimidine derivatives characterized by having a phenyl or substituted phenyl at positions 1 and 6 in addition being further substituted at position 2. The foregoing compounds are useful as diuretic agents in a mammal. Methods for the preparation and use of the compounds are disclosed.

1,4,5,6-Tetrahydropyrimidine derivatives

Pyrazinoisoindolone derivatives of the formula ##STR1## wherein R.sup.1 is lower alkyl, phenyl, diphenylmethyl, pyridinyl, pyrimidinyl, pyrazinyl or pyrazinyl substituted with a lower alkyl, lower alkoxy or halo; and R.sup.2 is hydrogen, lower alkyl or di(lower)alkylamino(lower)alkyl are useful as antihypertensive agents.

2,3-Dihydro-3-[4-(substituted)-1-piperazinyl]-1H-isoindol-1-ones

A process applicable to the preparation of a wide variety of novel polycyclic heterocycles having a newly-formed pyran ring is disclosed. According to the process an aromatic nucleus bearing an ethanol group, for example, 3,4-dimethoxyphenethyl alcohol, is condensed with an aldehyde or ketone or a protected aldehyde or ketone, for example, aminoactaldehyde diethyl acetal, in the presence of an acid catalyst to afford the polycyclic heterocycle, for example, 6,7-dimethoxy-1-isochromanmethylamine. The new heterocycles so formed are useful for preparing derivatives having antiinflammatory, antibacterial or antifungal activities.

Isochromans

This invention discloses novel 1-oxo-5H-pyrimidol[2,1-c][1,4]benzoxa(or thia)zinc-2-carboxylic acid lower alkyl esters, derivatives thereof, process for their preparation, pharmaceutical compositions thereof and methods for using the compounds. The compounds of this invention are useful in the treatment of anaphylactic reactions and allergic conditions in a mammal.

1-Oxo-5H-pyrimido[2,1-C]benzoxazine-2-carboxylic acid esters

This invention discloses novel 1-oxo-5H-pyrimido[2,1-c][1,4]benzoxa(or thia)zine-2-carboxylic acid lower alkyl esters, derivatives thereof, process for their preparation, pharmaceutical compositions thereof and methods for using the compounds. The compounds of this invention are useful in the treatment of anaphylactic reactions and allergic conditions in a mammal.

1-Oxo-5H-pyrimido[2,1-c][1,4]benzthiazine-2-carboxylic acid esters

3-Oxo-5H-pyrimido[2,1-c][1,4]benzoxazine derivatives, optionally substituted with a hydroxymethyl, carboxy or loweer alkoxycarbonyl at position 1 and optionally substituted at positions 8 or 9, with a lowr alkyl or halo are disclosed. The derivatives are antiallergy agents and methods for their preparation and use are given.

3-Oxo-5H-pyrimido[2,1-c][1,4 ]benzoxazines

Derivatives of 4,5-dihydro-4-oxofuran-2-carboxylic acid characterized by having two substituents at position 5 and in addition being optionally further substituted at position 3 with a lower alkyl group, as well as esters therefor are disclosed. The foregoing compounds are useful hypolipidemic agents in a mammal. Novel methods for the preparation of these compounds also are disclosed.

Hypolipidemic derivatives of 4,5-dihydro-4-oxofuran-2-carboxylic acid

1-Hydroxyimidazole-5-methanamine derivatives characterized by having a lower alkyl group at positions N, N and 5 of the latter derivatives as well as having various substituents at position 2 of the imidazole ring are disclosed. These derivatives are useful as antihypertensive agents in a mammal. Methods for their preparation, use and pharmaceutical compositions also are disclosed.

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Montreal, Canada

Ivo L Jirkovsky