Pfizer Corporation

Charles W Murtiashaw

Dennis Michael Godek

George Joseph Quallich

Frank J Urban

Brian C Vanderplas

Peter Thomas Stephenson

Stuart Peter Green

Triazole derivatives useful in therapy

(C.sub.1 -C.sub.3)Alkyl-4,6,7,8,9,9a-hexahydro-2H,3H-pyrido[1,2-a]pyrazin-1-one-7-c arboxylate esters, important precursors to certain bis-aza-bicyclic anxiolytics, can be prepared from di(C.sub.1 -C.sub.3)alkyl cis-piperidine-2,5-dicarboxylate starting material by a new process via a new class of intermediates, di(C.sub.1 -C.sub.3)alkyl cis-N-(2-(phthalimido)ethyl)piperidine-2,5-dicarboxylates. In the process, the starting material is reacted with either 2-(phthalimido)ethyl triflate or 2-(phthalimido)acetaldehyde to form the new intermediate, which can then be cyclized to the aforementioned precursor.

Process and intermediate for certain bis-aza-bicyclic anxiolytic agents

Azabicyclo [2.2.2.]octan-3-imines of the general formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined herein are prepared by reacting a compound of the formula ##STR2## with a compound of the formula ##STR3## wherein A is MgCl, MgBr or Li.

Process and intermediates for preparing azabicyclo[2.2.2]octan-3-imines

Immunoregulatory N-(S-3-alkyl-4-heptenoyl)- and N-(S-3-alkylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine and esters thereof are synthesized via R-trans-2-hexen-4-ols, R-3-alkyl-4-heptenoic acid and S-3-alkylheptanoic acid.

Processes and intermediates for

A process and intermediates for the manufacture of S-3-methylheptanoic acid from S-citronellol; a novel crystalline form of immunoregulatory N-(S-3-methlylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, an immunoregulatory agent; and an improved process and intermediates therefor.

Crystalline N-(S-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine,

The present invention relates to processes and intermediates for the preparation of spiro-heteroazolones. The latter compounds are useful as aldose reductase inhibitors.

Certain 3,4-dihydro-2H-pyrano[2,3-b]pyridines

Immunoregulatory N-(S-3-alkyl-4-heptenoyl)- and N-(S-3-alkylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine and esters thereof are synthesized via R-trans-2-hexen-4-ols, R-3-alkyl-4-heptanoic acid and S-3-alkylheptanoic acid.

A process and intermediates for the manufacture of S-3-methylheptanoic acid from S-citronellol; a novel crystalline form of immunoregulatory N-(S-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, an immunoregulatory agent; and an improved process and intermediates therefor.

Azabicyclo[2.2.2]octan-3-imines of the general formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined herein are prepared by reacting a compound of the formula ##STR2## ps with a compound of the formula wherein A is MgCl, MgBr or Li.

Process for preparing azabicyclo[2.2.2]octan-3-imines

A process and intermediates for the manufacture of S-3-methylheptanoic acid from S-citronellol; a novel crystallline form of immunoregulatory N-(S-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, an immunoregulatory agent; and an improved process and intermediates therefor.

(C.sub.1 -C.sub.3)Alkyl-4,6,7,8,9,9a-hexahydro-2H,3H-pyrido-[1,2-a]pyrazin-1-one-7- carboxylate esters, important precursors to certain bis-aza-bicyclic anxiolytics, can be prepared from di(C.sub.1 -C.sub.3)alkyl cis-piperidine-2,5-dicarboxylate starting material by a new process via a new class of intermediates, di(C.sub.1 -C.sub.3)alkyl cis-N-(2-(phthalimido)ethyl)piperidine-2,5-dicarboxylates. In the process, the starting material is reacted with either 2-(phthalimido)ethyl triflate or 2-(phthalimido)acetaldehyde to form the new intermediate, which can then be cyclized to the aforementioned precursor.

Azabicyclo[2.2.2]octan-3-imines of the general formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined herein are prepared by reacting a compound of the formula ##STR2## with a compound of the formula ##STR3## wherein A is MgCl, MgBr or Li.

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North Stonington, CT, United States of America

Charles W Murtiashaw