Wyeth

American Home Products Corporation

Wyeth Holdings Corporation

Zealand Pharma A/s

Pfizer Corporation

Ziarco Inc.

Panolil Raveendranath

Ronald S. Michalak

Panolil C Raveendranath

Jianxin Ren

Syed Muzafar Shah

Ronald Stanley Michalak

Sreenivasulu Megati

Mousumi Ghosh

Christoph Martin Dehnhardt

Joseph Zeldis

Yanzhong Wu

Galina Vid

Michael Z Kagan

Anita Wai-Yin Chan

Michael William Winkley

Mahmut Levent

Charles Chao Wu

John R Potoski

Silvio Iera

Karen Sutherland

Charles Guinosso

Frederick J Vyverberg

Ara R Boyajian

Michel Cantin

Alan Stockton

John A Wichtowski

John H Sellstedt

Mahdi Bakir Fawzi

Thomas Joseph Caggiano

Bogdan Kazimierz Wilk

Arthur G Mohan

Eric C Ehrnsperger

Lalitha Krishnan

Mahmoud Mirmehrabi

Gloria Cheal

John Potoski

Subodh S Deshmukh

John Leo Considine

Leonard Alexander McDonald

Maotang X Zhou

Razzak Noureldin

Asaf Ragim Alimardanov

Ting-Zhong Wang

Jason Brazzillo

Fangming Kong

Mark Edward Ruppen

Jianxin Gu

Annmarie Louise Sabb

James Albert Nelson

Warren Chew

Madelene M Antane

Mark A Collins

Arkadiy Zinoviy Rubezhov

Robert Lewis Vogel

Chia-Cheng Shaw

Zhixian Ding

Thurairajah Padmanathan

Michael D Smith

Constantine Gletsos

Xinxu Shi

Haris Durutlic

John Thomas Kendall

Yangzhong Wu

John Richard Potoski

Karen Wiggins Sutherland

Charles C Wu

Ronald S Michalak

Christoph Dehnhardt

Provided are methods for the preparation of certain substituted pyrrolidine compounds, forms of (2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid hydrochloride, and methods for preparing and using these forms.

Synthesis of pyrrolidine compounds

The present invention provides a compound of formula 1: wherein Ris CF, Ris H' Ris H.

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The present invention provides method for making a compound of formula 1: comprising the steps of reacting compounds of formulas 2 and 3: to produce a compound of formula 4: wherein R, R, R, Rand Rare defined as described herein. The compound of formula 4 is then converted to the compound of formula 1. The invention further comprises compounds of formulas 3 and 4 and methods for making compounds of formulas 3 and 4.

Processes for preparing sulfonamide trifluoroalkyl substituted alcohol compounds are provided. Desirably, the compounds are heterocyclic sulfonamide trifluoroalkyl substituted alcohol compounds or phenyl sulfonamide trifluoroalkyl substituted alcohol compounds.

Selective N-sulfonylation of 2-amino fluoro- and trifluoroalkyl substituted alcohols

Processes for preparing oxindoles, which can be utilized in the preparation of a variety of useful compounds, and methods for minimizing or preventing N-alkylation of amide containing compounds, including oxindoles, are provided. Also provided is a compound of the following structure: 

Process for the synthesis of progesterone receptor modulators

A method of selectively preparing a chiral 2S-amino alcohol useful in preparation of an amide sulfonated or acylated with alkyl, substituted aryl or substituted heteroaryl is described. The method involves reacting a di-tert-butyl diazene-1,2-dicarboxylate with a (4S)-4-benzyl-3-[(S)-trifluoromethyl-alkyl substituted alkanoyl]-1,3-oxazolidin-2-one to afford a di-tert-butyl 1-(1S,2S)-([(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-yl]-carbonyl}-trifluoromethyl-alkyl substituted alkyl)hydrazine-1,2-dicarboxylate. This dicarboxylate is then reduced to yield di-tert-butyl 1-(1S,2S)-[trifluoromethyl-alkyl substituted alkyl]hydrazine-1-(hydroxymethyl)-1,2-dicarboxylate. The resulting product is deblocked with an acid to yield the acid addition salt of (2S,3S)-trifluoro-hydrazino-methyl alkan-1-ol. The acid addition salt of (2S,3S)-trifluoro-2-hydrazino-methyl alkan-1-ol is hydrogenated in the presence of a suitable metal catalyst to yield the amino alcohol (2S,3S)-2-amino-trifluoro-methyl alkan-1-ol HCl.

Production of chirally pure amino alcohol intermediates, derivatives thereof, and uses thereof

A process for the reductive alkylation at the C-3 position of an indole compound in which the indole is treated with an aldehyde in the presence of a Lewis acid and a silicon hydride reducing agent. The process is useful for alkylating the C-3 position of indoles that contain acid-sensitive substituents at the N-1 position.

Synthetic methodology for the reductive alkylation at the C-3 position of indoles

Processes for preparing amino alcohols or salts thereof and sulfonamide substituted alcohol compounds are provided. Desirably, the sulfonamide substituted alcohol compounds are heterocyclic sulfonamide trifluoroalkyl-substituted alcohol compounds or phenyl sulfonamide trifluoroalkyl-substituted alcohol compounds.

Methods for preparing sulfonamide substituted alcohols and intermediates thereof

Selective dual serotonin and norepinephrine reuptake inhibitors are provided. These compounds have a lower side-effect profile and are useful in compositions and products for use in treatment of a variety of conditions including depression, fibromyalgia, anxiety, panic disorder, agorophobia, post traumatic stress disorder, premenstrual dysphoric disorder, attention deficit disorder, obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, autism, schizophrenia, obesity, anorexia nervosa, bulimia nervosa, Gilles de la Tourette Syndrome, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction, borderline personality disorder, fibromyalgia syndrome, diabetic neuropathic pain, chronic fatigue syndrome, pain, Shy Drager syndrome, Raynaud's syndrome, Parkinson's Disease, and epilepsy.

Serotonin and norepinephrine reuptake inhibitors and uses thereof

This invention relates to a process for the preparation of 6-hydroxyequilenins, which are useful as estrogenic agents.

Preparation of 6-hydroxyequilenins

A method of selectively preparing a chiral 2S-amino alcohol useful in preparation of an amide sulfonated or acylated with alkyl, substituted aryl or substituted heteroaryl is described. The method involves reacting a di-tert-butyl diazene-1,2-dicarboxylate with a (4S)-4-benzyl-3-[(S)-trifluoromethyl-alkyl substituted alkanoyl]-1,3-oxazolidin-2-one to afford a di-tert-butyl 1-(1S,2S)-([(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-yl]-carbonyl}-trifluoromethyl-alkyl substituted alkyl)hydrazine-1,2-dicarboxylate. This dicarboxylate is then reduced to yield di-tert-butyl 1-(1S,2S)-[trifluoromethyl-alkyl substituted alkyl]hydrazine-1-(hydroxymethyl)-1,2-dicarboxylate. The resulting product is deblocked with an acid to yield the acid addition salt of (2S,3S)-trifluoro-hydrazino-methyl alkan-1-ol. The acid addition salt of (2S,3S)-trifluor-2-hydrazino-methyl alkan-1-ol is hydrogenated in the presence of a suitable metal catalyst to yield the amino alcohol (2S,3S)-2-amino-trifluoro-methyl alkan-1-ol HCl.

Selective dual serotonin and norepinephrine reuptake inhibitors are provided. These compounds have a lower side-effect profile and are useful in compositions and products for use in treatment of a variety of conditions including depression, fibromyalgia, anxiety, panic disorder, agoraphobia, post traumatic stress disorder, premenstrual dysphoric disorder, attention deficit disorder, obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, autism, schizophrenia, obesity, anorexia nervosa, bulimia nervosa, Gilles de la Tourette Syndrome, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction, borderline personality disorder, fibromyalgia syndrome, diabetic neuropathic pain, chronic fatigue syndrome, pain, Shy Drager syndrome, Raynaud's syndrome, Parkinson's Disease, and epilepsy.

Serotonin and norepinephrine reuptake inhibitor and uses thereof

A process for making the compound of formula (I) wherein Ac represents acetate; X represents O or CH; Y represents C-Calkyl; and Z is selected from the group consisting of H, halogen, CN, CHO, CF, OCF, OH, C-Calkyl, C-Calkoxy, C-Cthioalkyl, NH, N(C-Calkyl), NH(C-Calkyl), NC(O)&#x2014;(CCalkyl), and NO. In his process, a compound of formula (II) is reacted with hydrazine to form a primary alkylamine, and then the primary alkylamine is reacted with acetic anhydride, to produce the compound of formula (I).

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Plattsburgh, NY, United States of America

Panolil C Raveendranath