Schering Corporation

Roche Palo Alto LLC

F. Hoffmann-la Roche Ag

Gary M Lee

Dinesh Gala

Wenxue Wu

Richard W Draper

Donald Hou

Hongbiao Liao

Janet L Mas

Martin Lawrence Schwartz

Suhan Tang

Andrew J Goodman

Jiang Zhu

Tiruvettipuram K Thiruvengadam

Xiaoyong Fu

David R Andrews

Timothy L McAllister

David J Tsai

David J S Tsai

Chou-Hang Tann

Donal Maloney

William W Leong

Keshab Sarma

Minzhang Chen

Humberto Bartolome Arzeno

Tong Xiao

Andrew D Jones

Juan Antonio Gamboa

Ingrid Mergelsberg

Michael Martin

Man Zhu

Xiongwei Shi

Christopher Nielsen

Bosco A D'sa

The present process provides a improved method for the preparation of alkylsulfanyl substituted triazoles 2 which are useful intermediates in a new process for the preparation of triazolones 20. 

Process for preparing triazolones

In an illustrative embodiment, the present invention describes the synthesis of the following compound and similar compounds, in high stereochemical purity by a novel stereoselective alkylation process: 

Stereoselective alkylation of chiral 2-methyl-4-protected piperazines

In one embodiment, the present invention discloses a process to directly prepare an unequal ratio of rotamers of an acid salt from a basic compound, by creative choice of a solvent medium. The process is particularly useful in preparing specific rotamers of pharmaceutically useful salts in desired preponderance.

Preparation of pharmaceutical salts

In its several embodiments, this invention discloses novel processes to prepare the compounds of formula II and formula IV:

Synthesis of piperidine and piperazine compounds as CCR5 antagonists

Preparation of salts of 4-[4-[(1R)-[4-(trifluoromethyl)phenyl]-2-methoxyethyl]-(3S)-methyl-1-piperazinyl]-4-methyl-1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]

In an illustrative embodiment, the present invention describes the synthesis of the following compound and similar compounds, in high stereochemical purity by a novel stereoselective alkylation process:

Disclosed are a process and intermediates of the formulae ##STR1## wherein X.sup.- is halide, BF.sub.4.sup.-, R.sup.3 SO.sub.3.sup.-, wherein R.sup.3 is C.sub.1 -C.sub.6 alkyl, CF.sub.3, C.sub.1 -C.sub.6 alkylphenyl or phenyl, and Q is a group of the formula ##STR2## wherein R is C.sub.1 -C.sub.6 alkyl; useful for preparing benzazepine intermediates of the formula ##STR3## These benzazepine intermediates are useful for preparing benzazepines having activity as selective D1 receptor antagonists.

Process for preparing intermediates for the synthesis of D1 antagonists

Disclosed are a process and intermediates of the formula ##STR1## wherein R is --CH.sub.3 or --C(O)--OR.sup.1, and R.sup.1 is C.sub.1 -C.sub.6 alkyl or --CH.sub.2 C.sub.6 H.sub.5 ; or the formula ##STR2## wherein: R.sup.2 is H or OH, R is --C(O)OR.sup.1 and R.sup.1 is C.sub.1 -C.sub.6 alkyl or --CH.sub.2 C.sub.6 H.sub.5, or where R.sup.2 is H, R can also be CH.sub.3 ; for preparing benzazepine intermediates of the formula ##STR3## The benzazepine intermediates are useful for preparing benzazepines having activity as selective D1 receptor antagonists.

Process for preparing benzazepine intermediates for the synthesis of D1

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Belmont, CA, United States of America

Gary M Lee