Merck + Co., Inc.

Zeneca Limited

David J Mathre

Guo-Jie Ho

Paul Sohar

Thomas J Blacklock

Lyndon C Xavier

Todd K Jones

Edward J Grabowski

Ralph P Volante

James M Balkovec

Kai Rossen

Zhiguo Jake Song

Richard F Shuman

Khateeta M Emerson

Roger N Farr

Andrew S Thompson

Shieh-Shung T Chen

Nobuyoshi Yasuda

Milton L Hammond

Robert D Larsen

Andrew John Blacker

Robert E Schwartz

David G Melillo

Dalian Zhao

Mark A Huffman

Edward G Corley

John Y Chung

Ann E DeCamp

Robert A Reamer

Brian R Petuch

F Edward Roberts

August J Kempf

Mallory F Loewe

Lynn M Brown

Anthony M DeMarco

David Moody

Julie J Mohan

James D Carroll

The invention encompasses a process for making compounds of Formula I or Ia useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1##

Intermediates for making heterocycles useful as COX-2 inhibitors

Process for making phenyl heterocycles useful as cox-2 inhibitors

Imidazolmethyloxy-substituted tricyclo-macrolide immunosuppressants are prepared by reacting a tricyclo-macrolide with an imidazolmethyl trichloroacetimidate in the presence of an acid. The invention further provides a crystalline salt of imidazolmethyloxy-substituted tricyclo-macrolide, as well as novel compounds useful in the process of the present invention.

Process for the preparation of imidazolyl macrolide immunosuppressants

Process for peptide segment condensation

This invention is concerned with an improved process for the synthesis of hydroxysulfone, which is a key intermediate in the synthesis of carbonic anhydrase inhibitors, especially dorzolamide. Carbonic anhydrase inhibitors are known to be effective in treating elevated intraocular pressure or glaucoma.

Synthesis of hydroxysulfone and related compounds

Process to derivatives of piperizinylcamphorsulfonyl oxytocin antagonists

A key step in the synthesis of 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno�2,3-b!thiopyran-2-su lfonamide 7,7-dioxide (dorzolamide) and related compounds is a Ritter reaction with an unexpected tendency to proceed with retention of chirality.

Enantioselective synthesis of

Pyridyl ethylation of lactam derivatives

The present invention is directed to a compound represented by the structural formula: ##STR1## wherein Z-- represents a negatively charged counterion.

Boronic acid compound

A process of synthesizing N-acyl auxiliary compounds is disclosed. A compound of the formula: ##STR1## is reacted with an anhydride in the presence of a lithium salt and an amine base to produce the N-acylated auxiliary.

Process of synthesizing N-acyl auxiliaries

This invention is concerned with an improved process for the synthesis of and intermediate en route to 5,6-dihydro-(s)-4-(ethylamino)-(s)-6-methyl-4h-thieno[2,3-b]thiopyran-2-su lfonamide 7,7-dioxide and related compounds. The instant process reduces the reaction time for the synthesis of the key intermediate from 3 to 4 days to from about 2 to about 4 hours while retaining the high enantiomeric purity of the product.

Synthesis of an intermediate for the preparation of

Process of synthesizing n-acyl auxiliaries

The present invention is directed to water-soluble derivatives of antibiotic lipopeptides having the formula. ##STR1## wherein R is H or OH and R' is a phosphono, sulfo or acyl radical possessing a charged group at neutral pH. The derivatives are esters but having a charged group, have good solubility properties in aqueous medium, rendering them more useful as therapeutic agents.

Lipopeptide derivatives

A process for obtaining a compound of the formula ##STR1## in crystalline form by solubilizing the compound in warm aqueous n-propanol and then allowing the solution to stand at ambient temperature until crystal formation is substantially complete is described. The crystalline compound obtained thereby is also described.

Process for crystalline cyclic lipopeptides

The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl- methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of diborane, borane-dimethyl sulfide or borane-tetrahydrofuran reductions of ketones to secondary alcohols.

Chiral catalysts for reduction of ketones and process for their

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Skillman, NJ, United States of America

David J Mathre