Apotex Pharmachem Inc.

Brantford Chemicals Inc.

Zhi-Xian Wang

Bhaskar Reddy Guntoori

Stephen E Horne

Mohammed Abdul Raheem

K S Keshava Murthy

Elena Bejan

Murali Kondamreddy

Svetoslav S Bratovanov

Bo Chen

Yutao Xue

Lihong Liu

Hao Chen

Gamini Weeratunga

Cameron L McPhail

David A Stradiotto

Alfredo Paul Ceccarelli

Eckardt C G Wolf

Chandrawansha B W Senanayake

Gurijala V Reddy

Abbulu Kante

YuanQiang Li

Xiongwei Cai

Joseph DiMartino

Yuanqiang Li

Yuan Qiang Li

The present invention provides a process for the preparation of Efavirenz. A compound of Formula 1: may be prepared by a process comprising cyclizing, in the presence of a first base, a compound of Formula 5 with a haloformate of Formula 6. Other processes are also provided as well as novel compounds prepared by and used in such processes.

Methods of making Efavirens and intermediates thereof

An industrially acceptable process for the preparation and purification of cis-2-methylspiro(1,3-oxathiolane-5,3')quiniclidine from a cis/trans mixture of isomers. Treatment of the mixture with an organic sulfonic acid generates a less soluble acid addition salt that is enriched in the cis-isomer. Recrystallization or pulping using various organic solvents allows for enrichment of the cis-isomer by filtration. These new sulfonic acid salts of the cis-isomer of 2-methylspiro(1,3-oxathiolane-5,3&#x2032;)quiniclidine prepared according to the present invention could be further converted into the hydrochloride salt by any known procedures such as treatment with a base and then hydrochloric acid salt formation or exchange of the sulfonic acid salt with hydrochloric acid.

Process for the preparation and purification of cis-2-methylspiro(1,3-oxathiolane-5,3')quiniclidine hydrochloride

Methods of making efavirenz and intermediates thereof

An industrially acceptable process for the preparation of 2-methylspiro(1,3-oxathiolane-5,3')quiniclidine. The cis-isomer of 2-methylspiro(1,3-oxathiolane-5,3&#x2032;)quiniclidine is known generally as Cevimeline.

Process for the preparation of 2-methylspiro(1,3-oxathiolane-5,3')quiniclidine

This invention relates to a new and efficient process for the production of dopamine agonists such as Cabergoline and the intermediates thereof.

Efficient process for the preparation of cabergoline and its intermediates

A process provided for the preparation of the (S)- and (R)- alpha- ethyl-2-oxo-1-pyrrolidineacetamide of formula:(1) from (RS)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid of formula:(2) comprising: i) combining the (RS)-2 with a chiral base (resolving agent) in a resolution solvent and crystallizing from the said mixture the diastereomeric salt of (S)- or (R)-2 and chiral base; ii) regenerating (S)- or (R)-2 from the crystallized diastereomeric salt by treating with a suitable acid or acidic ion-exchange resin; iii) optionally regenerating (R)- or (S)-2 or their mixture (predominantly one enantiomer) from the crystallization mother liquor by treating with a suitable acid or acidic ion-exchange resin; iv) optionally epimerizing (RS)-2 by treating (R)- or (S)-2 or their mixture (predominantly one enantiomer) of step iii with an acid anhydride; V) optionally converting (RS)-2 of step iv into enantiomerically enriched (S)- or (R)-2 through steps i and ii; vi) formation of the mixed anhydride by reacting (R)- or (S)-2 with an alkyl or aryl sulfonyl halogen compound RSO2X in the presence of a suitable base; and vii) reacting the mixed anhydride with ammonia; wherein R represents C 1 to C 15 alkyl or aryl groups such as methyl, ethyl, p-toluenyl, 2,4,6-trimethylbenzyl, 2,4,6-trichloribenzyl, and X represents a halogen atom such as F, Cl and Br atoms. 

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This invention relates to a process for the preparation of an aminoalkyl phenyl carbamate compound of formula 1, wherein Rand Rindependently are hydrogen or Calkyl; Rand Rare the same or different and each is a lower alkyl; or Rand Rtogether with the nitrogen to which they are attached form a cyclic moiety of a three to eight-member ring, with or without a hetero atom like nitrogen or oxygen; Rand Rindependently are hydrogen, linear, branched or cyclic Calkyl, allyl, propargyl or benzyl; or Rand Rtogether with the nitrogen to which they are attached form a cyclic moiety of three to eight member ring, with or without a hetero atom like nitrogen or oxygen; the carbon center marked with '*' is racemic or enantiomerically enriched (R)- or (S)-configuration; and pharmaceutically acceptable addition salts, and crystalline and amorphous forms thereof comprising the steps of:  

Process for the preparation of phenylcarbamates

A process for the preparation of aminoalkyl phenyl carbamate compounds of Formula I, wherein Rand Rindependently are hydrogen or a Calkyl; Rand Rare the same or different and each is a Calkyl; or Rand Rtogether with the nitrogen to which they are attached form a cyclic three to eight membered ring, with or without a heteroatom like nitrogen or oxygen; Rand Rindependently are hydrogen, linear, branched or cyclic Calkyl; or Rand Rtogether with the nitrogen to which they are attached form a cyclic three to eight membered ring, with or without a heteroatom like nitrogen or oxygen; the carbon centre designated '*' can be racemic or enantiomerically enriched in the (R)- or (S)- configuration; and pharmaceutically acceptable acid addition salts thereof.

The present invention relates to a process for producing 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones of formula 1, including Finasteride and Dutasteride.

Process for the preparation of 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones

Provided is an efficient method for the preparation of 3-aryloxy-3-arylpropylamines, their optical stereoisomers, and pharmaceutically acceptable salts thereof. The process allows for the isolation of 3-aryloxy-3-arylpropylamines in high yield and purity. The present invention further relates to a process for producing fluoxetine, tomoxetine, norfluoxetine, duloxetine, nisoxetine, and their optically enriched (R)- and (S)-enantiomers.

Efficient method for preparing 3-aryloxy-3-arylpropylamines and their optical stereoisomers

A process for the preparation of the boron difluoride chelate of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolone carboxylic acid via:

Process for the preparation of the boron difluoride chelate of quinolone-3-carboxylic acid

Process for the preparation of Flecainide, its pharmaceutically acceptable salts and important intermediates thereof that involves the use of the 2-halobenzoic acid and its derivatives as a starting material. The use of this process also allows for the synthesis of a novel intermediate useful in the production of Flecainide. This new process is an inexpensive and efficient process for the manufacture of these compounds.

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Brantford, Canada

Zhi-Xian Wang