Gilead Sciences, Inc.

Pfizer Corporation

Genencor International, Inc.

Bioavailability Systems, L.l.c.

Dsm Pharmaceuticals, Inc.

Other

Catalytica Pharmaceuticals, Inc.

Robert Seemayer

Jeff A Zablocki

Elfatih O Elzein

Jack S Liang

Travis Lemons

Charles T Goodhue

Thomas C Nugent

John M Gruber

Gregory Marshall Whited

Yian Shi

Matthew W Chase

Theresa C Paulson

Elfatih Elzein

Jeff Zablocki

Disclosed is a synthesis suitable for large scale manufacture of an A-adenosine receptor agonist, and also relates to polymorphs of that compound, and to methods of isolating a specific polymorph.

Process for preparing an A2A-adenosine receptor agonist and its polymorphs

Disclosed is a synthesis suitable for large scale manufacture of an A-adenosine receptor agonist, namely, (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazol-4-yl)-N-methylcarboxamide. Also, disclosed are polymorphs of this compound and methods for isolating a specific polymorph. Also, disclosed are pharmaceutical compositions and methods for preparing pharmaceutical compositions.

Monohydrate of (1-{9-[4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazol-4-yl)-N-methylcarboxamide

The present invention is directed to a process for preparing (S,S)-cis-2-phenyl-3-aminopiperidine and (S,S)-cis-2-phenyl-3-tertbutoxycarbonylaminopiperidine.

Process for the preparation of (S,S)-cis-2-phenyl-3-aminopiperidine

A process for preparing (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine. The process includes the steps of contacting a compound containing a mixture of R- and S-isomers and having the formulawith an effective amount of a chiral organic acid in the presence of an organic solvent and an effective amount of an organic carboxylic acid for converting the R-isomer into an acid salt of the S isomer, wherein the organic solvent is capable of solubilizing the compound containing the mixture of R- and S-isomers, while precipitating the acid salt and the organic carboxylic acid is different from the chiral organic acid; neutralizing the acid salt with a base to provide an S-isomer of a chiral ketone of the formula; and reacting the chiral ketone with an organic amine in the presence of a Lewis acid to provide the corresponding imine and reducing the imine.

Process for the preparation of (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine

Ortho esters and ortho carbonates can be produced by alkylating esters and carbonates with, for example, the hexafluorophosphate salt of a trialkyl oxonium ion. The spiro species are useful intermediates in the synthesis of complex organic molecules. Synthetic pathways for the production of medically active compounds incorporates spiro ortho esters. Anti-first-pass effect materials are produced in high yield utilizing a synthetic strategy incorporating cyclic ortho ester intermediates.

Synthesis of spiro esters, spiro ortho carbonates, and intermediates

Synthesis of spiro ortho esters, spiro ortho carbonates, and intermediates

The present invention provides a method for enantioselectively producing a nonracemic 6,7-dihydroxy geranyloxy compound from a geranyloxy compound. In particular, methods of the present invention involve enantioselectively epoxidizing the geranyloxy compound and hydrolyzing the epoxide moiety under conditions sufficient to produce the nonracemic 6,7-dihydroxy geranyloxy compound.

Preparation of chiral 6,7-dihydroxy geranyloxy compounds

This invention provides a process for preparing acylaromatics comprising reacting an aromatic compound with a carboxylic acid in the presence of a reaction medium comprising polyphosphoric acid and a strong protic acid. In one embodiment, the invention provides a process for preparing a para-acyl phenoxyethylamine comprising the steps of reacting a 2-phenoxyethyl compound bearing a leaving group on the ethyl 1-position with a carboxylic acid in the presence of a reaction medium comprising polyphosphoric acid and a strong protic acid, to form apara-acyl phenoxyethyl intermediate bearing the leaving group; and reacting the para-acyl phenoxyethyl intermediate with an amine that substitutes for the leaving group to form the para-acyl phenoxyethylamine.

Process for preparing acylaromatic compounds

Provided are enzymatic methods for the selective hydrolytic resolution of certain enantiomers of a pharmaceutical compound, the pharmaceutical compound comprising a (.+-.) mixture of a .alpha.-substituted 2-methyl proprionic acid derivative. Specifically provided is the selective enzymatic resolution of either the R(+) or S(-) enantiomer of (.+-.)-ethyl ciprofibrate. Also provided are substantially pure enantiomers of R(+) and S(-) ciprofibrate.

Enzymatic resolution of substituted 2-methyl-propionic acid

There is provided a regio-selective method for the resolution of carbohydrate monoester mixtures, by treating such mixtures with one or more selective enzymes. The resolution of such mixtures results in monoesters comprising significantly purer isolates of one desired isomer.

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Belmont, CA, United States of America

Robert Seemayer