Pfizer Corporation

Philip D Hammen

George M Milne, Jr

Keith Michael DeVries

Stephen S Massett

John L Tucker

Dennis J Hoover

Peter Robert Rose

Berkeley W Cue

Darrell E Fox

Constantine Sklavounos

Joanna Teresa Negri

Richard S Lehner

Kerry P Mahon

Jeffrey B Jorgensen

Diane M Rescek

Lulin Wei

Andrew C Braisted

Process for preparing 4&Prime;-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives

The present invention provides novel processes for preparing 3(S)-&lsqb;(5-chloro-1H-indole-2-carbonyl)-amino&rsqb;-2(R)-hydroxy-4-phenyl-butyric acid. Also provided are novel intermediates used in those processes. Further, the 3(S)-&lsqb;(5-chloro-1H-indole-2-carbonyl)-amino&rsqb;-2(R)-hydroxy-4-phenyl-butyric acid prepared by the novel processes can be further reacted to yield known indole 2-carboxamides and derivatives thereof possessing glycogen phosphorylase inhibitory activity, which are useful in the treatment of mammals, especially human beings, having glycogen phosphorylase dependent diseases or conditions.

Processes and intermediates for preparing 3(S)-&lsqb;(5-chloro-1H-indole-2-carbonyl)-amino&rsqb;-2(R)-hydroxy-4-phenyl-butyric acid

A process of purifying a (6-chloro-2-carbazolyl)methyl-malonic acid di(C.sub.1 -C.sub.6 alkyl) ester of Formula (I): ##STR1## wherein R.sub.a and R.sub.b must be the same and are selected from the group consisting of C.sub.1 -C.sub.6 alkyl; comprises phase separating one or more impurities from said carbazole ester at least once wherein the solvent used to carry out said phase separation is acetic acid. In a preferred embodiment said acetic acid is glacial acetic acid which is maintained at a temperature of from about 30.degree. to about 110.degree.0 C. and said carbazole ester is obtained in a purity of at least 99.90% by weight, so that the amount of impurities present therein is 0.10% or less by weight. In a more preferred embodiment of said process, said temperature is from about 50.degree. to about 70.degree. C., and said phase separation is carried out only once.

Method of purifying carbazole ester precursors of

Benzothiazine dioxide derivatives

6-Fluoro-4-chromanone, a sorbinil intermediate, is regenerated from enantiomeric and mixtures of enantiomeric and racemic compounds obtained as major by-products in the synthesis of sorbinil. The regenerated intermediate is useful in the synthesis of additional sorbinil.

Regeneration of 6-fluoro-4-chromanone from by-products in the synthesis

Novel 2-aminomethyleneindanones having analgesic activity are disclosed.

2-Aminomethyleneindanone analgesic agents

Process for production of 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic acid-1,1-dioxide by hydrolysis, in the presence of hydroxide ions, of an alkyl or aralkyl ester thereof followed by precipitation of the acid at pH below 6.0 and its use as an intermediate for the production of N-(2-pyridyl)-3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxamid e-1,1-dioxide and the analogous N-(2-thiazolyl)-compound, effective antiinflammatory agents.

3,4-Dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic

Certain 2-(4-aroylpiperazin-1-yl)-4-amino-6,7-dimethoxyquinazolines are prepared by a novel process wherein certain 2-(4-substituted-piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline intermediates wherein said substituent is cyano, certain carbon-oxygen double bond containing groups or certain carbon-nitrogen double bond containing groups, are reacted with certain metalloaryl compounds followed by hydrolysis. The products are known hypotensive agents. Certain of the process intermediates are novel compounds.

Process for preparing hypotensive

6-(Triphenylmethylamino)-2,2-dimethyl-3-(N-[p-methoxybenzyl]carbamoyl)penam -dimethylsulfoxide complex as a useful intermediate leading to the synthesis of antibacterial 6-acylamino-2,2-dimethyl-3-(5-tetrazolyl)penams.

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East Lyme, CT, United States of America

Philip D Hammen