Wyeth

Purdue Pharma L.p.

Timothy John Doyle

David Michael Blum

Kevin Brown

Yanzhong Wu

Jean Schmid

John W F Whitehead

Jay Thomas Afragola

Joseph Zeldis

Ronald Stanley Michalak

Mel Jennings

Methods, composition, and intermediates are disclosed that are useful for making 4-Tetrazolyl-4-phenylpiperidine Compounds according to Formula I, where Aris &#x2014;C-Ccycloalkyl, phenyl, naphthyl, anthryl, phenanthryl or -(5-7-membered) heteroaryl, each being unsubstituted or substituted with one or more Rgroups; Aris phenyl, naphthyl, anthryl, phenanthryl or -(5-7-membered) heteroaryl, each being unsubstituted or substituted with one or more Rgroups; Zand Zare each independently a &#x2014;(C-Calkyl) group; Ris &#x2014;(CH)C(O)N(R)(R) where Rand Rare each independently H or &#x2014;(C-Calkyl); Ris halogen, &#x2014;C-Calkyl, &#x2014;O&#x2014;(C-Calkyl), &#x2014;NH(C-Calkyl) or &#x2014;N(C-Calkyl); n is an integer ranging from 1 to 4; m is an integer ranging from 0 to 4; and, in certain embodiments, the phenyl moiety attached to the 4-position of the piperidine ring of a compound according to Formula I can be optionally substituted with one or more Rgroups.

Methods for making 4-tetrazolyl-4-phenylpiperidine compounds

The present invention relates to novel methods for the preparation of glutamic acid derivatives and intermediates thereof, and such compounds prepared by the novel methods.

Methods for preparing glutamic acid derivatives

The invention provides 6-chloro-5-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-2-pyrazin-2-yl-N-[(1S)-2,2,2-trifluoro-1-methylethyl]pyrimidin-4-amine hemifumarate which is a tubulin inhibitor useful in the treatment of cancer and processes of making said hemifumarate.

Tubulin inhibitor and process for its preparation

The invention provides 6-chloro-5-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-2-pyrazin-2-yl-N-[(1S)-2,2,2-trifluoro-1-methylethyl]pyrimidin-4-amine hemifumarate which is a tubulin inhibitor useful in the treatment of cancer and processes of making hemifumarate compounds and compositioning of the present invention.

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Morristown, NJ, United States of America

Timothy John Doyle