Pfizer Corporation

R Mark Guinn

Derek Lawrence Tickner

Clifford N Meltz

Subramanian Sam Guhan

Marcus D Ewing

Kees Pouwer

Bryan Li

Karl K Ng

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

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Mystic, CT, United States of America

R Mark Guinn