Smithkline Corporation

Smithkline Beckman Corporation

Kenneth G Holden

John G Gleason

William F Huffman

Nelson C Yim

Carl Kaiser

Joseph Weinstock

Carl D Perchonock

A chemical process is described for preparing 7,8-acetamido, hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines which involves reacting a 7,8-quinone derivative of a 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine with a benzyl or benzhydrylamine followed by hydrolysis of the resulting imine and reaction with acetic anhydride or acetyl chloride.

Process useful for preparing 7,8-acetamido,

A group of new chemical compounds are described which are intermediates for preparing 7,8-amino, hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines. The intermediates are distinguished in structure by a benzyloxy substituent at either the 7 or 8-position.

Intermediates for preparing 7,8-amino,

A group of 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines whose structures have amino, hydroxy substituents at the 7,8-positions of the benzazepine nucleus is disclosed. Novel intermediates and routes of synthesis used for preparing them are also described. The end products have pharmacodynamic activity.

7,8-Amino, hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines

Mercapto substituted-2,3,4,5-tetrahydro-1H-3-benzazepines having dopamine receptor blocking activity are prepared from o-quinones or via standard preparative procedures.

6-Phenyl thio- and 6-cyclohexyl thio-2,3,4,5-tetrahydro-1H-3-benzazepines

The stereospecific cycloaddition of nitrogen containing acetic acid halides or anhydrides with Schiff bases having a carbalkoxy group substituted on the methine carbon atom offers new intermediates and methods for preparing synthetic cephalosporin congeners having antibacterial activity.

3-Amino-2-hydroxy, halo or mercaptomethyl-4-oxoazetidines

A new series of lower alkylthio-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines having potent central dopaminergic activity of utility in treating Parkinson's disease. The 6-and 9-methylthio compounds are particularly of use.

Alkylthio-7,8-dihdroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines

A novel process for preparing 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline by cyclizing N-acetyl-2,3-dichlorobenzylaminoacetaldehyde dimethyl acetal with a Lewis acid, reducing, and hydrolyzing the resulting acylated isoquinoline is disclosed.

Method for preparing 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline

Substituted azetidine intermediates for preparing novel bicyclic .beta.-lactam penicillin analogs which have antibacterial activity are disclosed.

Substituted azetidinones

A group of 7,8-dihydroxy-2,3,4,5-tetrahydro-1H-3-benzazepines with structures containing a furyl ring at position 1 which have dopaminergic activity. Particular species of this group include 7,8-dihydroxy-1-(furyl)-2,3,4,5-tetrahydro-1H-3-benzazepine and its dimethyl ether derivative.

Substituted furyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds and

Novel benzazepine derivatives having central and peripheral dopaminergic activity useful in treating Parkinson's and cardiovascular diseases. The compounds have additional use as intermediates for the synthesis of other benzazepines with similar useful properties. The 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione derivatives are particularly useful.

2,3,4,5-Tetrahydro-1H-3-benzazepine-7,8-diones

Methods and intermediates for preparing cis-4-oxoazetidine intermediates

A group of 7,8-dihydroxy-2,3,4,5-tetrahydro-1H-3-benzazepines with structures containing a thienyl or furyl ring at position 1 which have dopaminergic activity. Particular species of this group include 7,8-dihydroxy-1-(5'-methyl-2'-thienyl)-2,3,4,5-tetrahydro-1H-3-benzazepine and its dimethyl ether derivative, 7,8-dihydroxy-1-(2'-thienyl)-2,3,4,5-tetrahydro-1H-3-benzazepine and its dimethyl ether as well as 7,8-dihydroxy-1-(3'-thienyl)-2,3,4,5-tetrahydro-1H-3-benzazepine and its dimethyl ether.

Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1H-3-benzazepine

A new process is disclosed for the preparation of N-acyl-.alpha.-aromatic and N-acyl-.alpha.-heteroaromatic glycines by reaction of an .alpha.-ester or ether of an N-acylglycine ester or acid with an aromatic or heteroaromatic compound. Also disclosed are new intermediates for preparing N-acyl-.alpha.-aromatic and N-acyl-.alpha.-heteroaromatic glycines.

Process for preparing substituted glycines

Novel bicyclic .beta.-lactams and intermediates useful in their preparation are disclosed. In particular, 7.beta.-acyl-amino- and 7.beta.-amino-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids are prepared. The acylated compounds are antibacterial agents.

Growing community of inventors

Haddonfield, NJ, United States of America

Kenneth G Holden