Eli Lilly and Company

Vanda Pharmaceuticals Inc.

Michael Edward Kobierski

Charles J Barnett

Thomas M Wilson

Michael E Kopach

Pingyun Chen

Bret Anthony Astleford

John Arnold Werner

Steven Eugene Dunlap

The disclosure provides process developments and novel routes for the preparation of the NK-1 receptor antagonist, Compound (I) and intermediates in those routes. 

Process development of a pyridine-containing NK-1 receptor antagonist

The present invention relates to novel compounds, (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone benzoate, and (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone toluate, which are useful intermediates for the preparation of the compound of Formula I:  The present invention further relates to novel processes for preparing a crystalline compound, which is {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV.

Intermediate and process useful in the preparation of {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone

Intermediate and process useful in the preparation of {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl)-(2-chlorophenyl)-methanone

This invention provides a process to prepare (2R)-anti-5-&lcub;3-&lsqb;4-(10,11-difluoromethanodibenzosuber-5-yl)piperazin-1-yl&rsqb;-2-hydroxypropoxy&rcub;quinoline.

Process for preparing a 10,11-methanodibenzosuberane derivative

Processes and intermediates useful to make antifolates

Processes for preparing 4-hydroxy-5-ethynylpyrrolo[2,3-d]pyrimidine intermediates and N-[4-(2-{4-hydroxypyrrolo[2,3-d]pyrimidin-3-yl}ethyl)benzoyl]-L-glutamic acid derivatives having antineoplastic activity are provided.

Process for the preparation of 4-hydroxy-5-substituted ethynylpyrrolo

4-Hydroxypyrrolo[2,3-d]pyrimidines are regiospecifically halogenated at the C-5 position by silylation in the presence of an inert organic solvent and iodination, bromination or chlorination.

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Greenwood, IN, United States of America

Michael Edward Kobierski