Pfizer Corporation

Other

Darrell E Fox

Tamim F Braish

Timothy Norris

Stanley W Walinsky

Peter Robert Rose

Dennis J Hoover

John F Lambert

Keith Michael DeVries

Philip D Hammen

Terry G Sinay

Tamin F Braish

Jeffrey B Jorgensen

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

Processes and intermediates for preparing

Process and intermediates for preparing naphthyridonecarboxylic acid

1S,4S and 1R,4R-2-Alkyl-2,5-diazabicyclo[2.2.1]-heptanes useful as intermediates in the synthesis of certain antibacterial quinolones, are prepared respectively, from trans-4-hydroxy-L-proline and trans-4-hydroxy-D-proline via multistep procedures.

Process for optically active 2-alkyl-2,5-diazabicyclo[2.2.1] heptanes

1S,4S and 1R,4R-2-Alkyl-2,5-diazabicyclo[2.2.1]heptanes useful as intermediates in the synthesis of certain antibacterial quinolones, are prepared respectively, from trans-4-hydroxy-L-proline and trans-4-hydroxy-D-proline via multistep procedures.

Process for optically active 2-alkyl-2,5-diazabicyclo[2.2.1]heptanes

Diazabicyclo[2.2.1]heptane intermediates are prepared from 4-hydroxy-L-proline in a five step procedure, or from allo-4-hydroxy-D-proline, through a novel 2-(C.sub.1 -C.sub.6)alkyl-5-substituted-2,5-diazabicyclo[2.2.1]heptane intermediate. The diazabicycloheptanes are of use in the preparation of antibiotic quinolones.

Preparation of diazabicyclic Intermediates

1S, 4S and 1R,4R-2-Alkyl-2,5-diazabicyclo[2.2.1]-heptanes useful as intermediates in the synthesis of certain antibacterial quinolones, are prepared respectively, from trans-4-hydroxy-L-proline and trans-4-hydroxy-D-proline via multistep procedures.

Optically active 2-alkyl-2,5-diazabicyclo[2.2.1]heptanes

Process for optically active 2-alkyl-2,5-diazabicyclo(2.2.1)heptanes

(R,R)-2,5-Diazabicyclo[ 2.2.1]heptanes are prepared from a compound of the formula ##STR1## wherein X and R.sub.2 are as defined herein, by heating with tosylchloride in pyridine, reacting the formed compound of the formula ##STR2## with a C.sub.1 -C.sub.6 alkylamine or ammonia, and reducing or hydrolyzing the formed compound of the formula ##STR3## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.6 alkyl.

Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates

1S,4S and 1R,4R-2-alkyl-2,5-diazabicyclo[2.2.1]-heptanes useful as intermediates in the synthesis of certain antibacterial quinolones, are prepared respectively, from trans-4-hydroxy-L-proline and trans-4-hydroxy-D-proline via multistep procedures.

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Pawcatuck, CT, United States of America

Darrell E Fox