Pfizer Corporation

Clifford N Meltz

Derek Lawrence Tickner

Gordon D Gruetzmacher

Ping W Chang

Joseph P Lyssikatos

Zheng Jane Li

Peter Robert Rose

Frank R Busch

Charles K Chiu

Subramanian Sam Guhan

Marcus D Ewing

Kees Pouwer

R Mark Guinn

Linda S Newton

Karl K Ng

Ronald J Post

Bryan Li

Rocco A Totino

This invention relates to the enantiomers of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-[3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-1-methyl-1H-quinolin-2-one, prodrugs thereof, and pharmaceutically acceptable salts and solvates of said compounds and said prodrugs, that are useful in the treatment of hyperproliferative diseases, such as cancers, in mammals. The invention also relates to processes for the production of enantiomerically pure or optically enriched (+)- or (&#x2212;)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-[3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-1-methyl-1H-quinolin-2-one enantiomers from a mixture containing two enantiomers using continuous chromatography. The invention further relates to the L-(+)-tartaric acid or (S)-(&#x2212;)-1,1'-binapthyl-2,2&#x2032;-diyl hydrogenphosphate salts of (+)-6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-[3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-1-methyl-1H-quinolin-2-one.

Enantiomers of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-[3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-1-methyl-1H-quinolin-2-one and salts thereof, useful in the treatment of cancer

This invention relates to the enantiomers of 6-&lsqb;(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl&rsqb;-4-&lsqb;3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl&rsqb;-1-methyl-1H-quinolin-2-one, prodrugs thereof, and pharmaceutically acceptable salts and solvates of said compounds and said prodrugs, that are useful in the treatment of hyperproliferative diseases, such as cancers, in mammals. The invention also relates to processes for the production of enantiomerically pure or optically enriched (&plus;)- or (&minus;)-6-&lsqb;(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl&rsqb;-4-&lsqb;3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl&rsqb;-1-methyl-1H-quinolin-2-one enantiomers from a mixture containing two enantiomers using continuous chromatography. The invention further relates to the L-(&plus;)-tartaric acid or (S)-(&minus;)-1,1&prime;-binapthyl-2,2&prime;-diyl hydrogenphosphate salts of (&plus;)-6-&lsqb;(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl&rsqb;-4-&lsqb;3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl&rsqb;-1-methyl-1H-quinolin-2-one.

ENANTIOMERS OF 6-&lsqb;(4-CHLORO-PHENYL)-HYDROXY-(3-METHYL-3H-IMIDAZOL-4-YL)-METHYL&rsqb;-4-&lsqb;3-(3-HYDROXY-3-METHYL-BUT-1-YNYL)-PHENYL&rsqb;-1-METHYL-1H-QUINOLIN-2-ONE AND SALTS THEREOF, USEFUL IN THE TREATMENT OF CANCER

Crystal forms of 6-&lsqb;(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl&rsqb;-4-(3-ethynyl-phenyl)-1-methyl-1H-quinolin-2-one, 2,3,- dihydroxybutanedioate salts and method of production

Process for preparing growth hormone secretagogues

Crystal forms of 6-&lsqb;(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl&rsqb;-4-(3-ethynyl-phenyl)-1-methyl-1H-quinolin-2-one, 2,3-dihydroxybutanedioate salts and method of production

Aqueous gel-forming compositions are prepared by reacting for 1-10 hours at 50.degree.-95.degree. C., melamine, formaldehyde and a sulfurous acid salt with the optional addition of a gel-modifying agent and/or a gelling agent which is added to the composition immediately prior to use.

Aqueous sulfomethylated melamine gel-forming compositions and methods of

Aqueous sulfomethylated melamine gel-forming compositions

Hydrocarbon recovery from subterranean reservoirs that are penetrated by either injector or producer wells is enhanced by selective permeability modification of the strata of the reservoir with gel-forming phenolic compositions. The injection of the phenolic composition follows a pH sequence specific to the reservoir environment which allows emplacement of the gel-forming composition the desired distance away from the wellbore and production of a uniform gel throughout the treated hydrocarbon-bearing reservoir. The permeability of a treated subterranean reservoir can be restored by treatment of the reservoir with either aqueous hypochlorite or mineral acid.

Enhanced hydrocarbon recovery by permeability modification with phenolic

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Niantic, CT, United States of America

Clifford N Meltz