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Claims for Patent: 8,785,632

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Claims for Patent: 8,785,632

Title:Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors
Abstract: Enantiomerically pure compound of formula 1 ##STR00001## are provided, as well as methods for their synthesis and use. Preferred compounds are potent inhibitors of the c-Met protein kinase, and are useful in the treatment of abnormal cell growth disorders, such as cancers.
Inventor(s): Cui; Jingrong Jean (San Diego, CA), Funk; Lee Andrew (Oceanside, CA), Jia; Lei (San Diego, CA), Kung; Pei-Pei (San Diego, CA), Meng; Jerry Jialun (San Diego, CA), Nambu; Mitchell David (San Diego, CA), Pairish; Mason Alan (San Diego, CA), Shen; Hong (San Diego, CA), Tran-Dube; Michelle (La Jolla, CA)
Assignee: Agouron Pharmaceuticals, Inc. (San Diego, CA) Pfizer Inc. (New York, NY)
Application Number:13/537,759
Patent Claims: 1. An enantiomerically pure compound of formula 1 ##STR00130## wherein: Y is CR.sup.12; R.sup.1 is 5-12 membered heteroaryl; and each hydrogen in R.sup.1 is optionally replaced by one or more R.sup.3 groups; R.sup.2 is hydrogen; each R.sup.3 is independently halogen, C.sub.1-12 alkyl, C.sub.2-12 alkenyl, C.sub.2-12 alkynyl, C.sub.3-12 cycloalkyl, C.sub.6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, --S(O).sub.mR.sup.4, --SO.sub.2NR.sup.4R.sup.5, --S(O).sub.2OR.sup.4, --NO.sub.2, --NR.sup.4R.sup.5, --(CR.sup.6R.sup.7).sub.nOR.sup.4, --CN, --C(O)R.sup.4, --OC(O)R.sup.4, --O(CR.sup.6R.sup.7).sub.nR.sup.4, --NR.sup.4C(O)R.sup.5, --(CR.sup.6R.sup.7).sub.nC(O)OR.sup.4, --(CR.sup.6R.sup.7).sub.nC(O)NR.sup.4R.sup.5, --(CR.sup.6R.sup.7).sub.nNCR.sup.4R.sup.5, --C(.dbd.NR.sup.6)NR.sup.4R.sup.5, --NR.sup.4C(O)NR.sup.5R.sup.6, or --NR.sup.4S(O).sub.pR.sup.5, each hydrogen in R.sup.3 is optionally replaced by R.sup.8, and R.sup.3 groups on adjacent atoms may combine to form a C.sub.6-12 aryl, 5-12 membered heteroaryl, C.sub.3-12 cycloalkyl or 3-12 membered heteroalicyclic group; each R.sup.4, R.sup.5, R.sup.6 and R.sup.7 is independently hydrogen, halogen, C.sub.1-12 alkyl, C.sub.2-12 alkenyl, C.sub.2-12 alkynyl, C.sub.3-12 cycloalkyl, C.sub.6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl; or any two of R.sup.4, R.sup.5, R.sup.6 and R.sup.7 bound to the same nitrogen atom may, together with the nitrogen to which they are bound, be combined to form a 3 to 12 membered heteroalicyclic or 5-12 membered heteroaryl group optionally containing 1 to 3 additional heteroatoms selected from N, O, and S; or any two of R.sup.4, R.sup.5, R.sup.6 and R.sup.7 bound to the same carbon atom may be combined to form a C.sub.3-12 cycloalkyl, C.sub.6-12 aryl, 3-12 membered heteroalicyclic or 5-12 membered heteroaryl group; and each hydrogen in R.sup.4, R.sup.5, R.sup.6 and R.sup.7 is optionally replaced by R.sup.8; each R.sup.8 is independently halogen, C.sub.1-12 alkyl, C.sub.2-12 alkenyl, C.sub.2-12 alkynyl, C.sub.3-12 cycloalkyl, C.sub.6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, --NH.sub.2, --CN, --OH, --O--C.sub.1-12 alkyl, --O--(CH.sub.2).sub.nC.sub.3-12 cycloalkyl, --O--(CH.sub.2).sub.nC.sub.6-12 aryl, --O--(CH.sub.2).sub.n(3-12 membered heteroalicyclic) or --O--(CH.sub.2).sub.n(5-12 membered heteroaryl); and each hydrogen in R.sup.8 is optionally replaced by R.sup.11; each R.sup.11 is independently halogen, C.sub.1-12 alkyl, C.sub.3-12 cycloalkyl, C.sub.6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, --O--C.sub.1-12 alkyl, --O--(CH.sub.2).sub.nC.sub.3-12 cycloalkyl, --O--(CH.sub.2).sub.nC.sub.6-12 aryl, --O--(CH.sub.2).sub.n(3-12 membered heteroalicyclic), --O--(CH.sub.2).sub.n(5-12 membered heteroaryl) or --CN, and each hydrogen in R.sup.11 is optionally substituted by halogen, --OH, --CN, --C.sub.1-12 alkyl which may be partially or fully halogenated, or --O--C.sub.1-12 alkyl which may be partially or fully halogenated; R.sup.12 is hydrogen; each m is independently 0, 1 or 2; each n is independently 0, 1, 2, 3 or 4; and each p is independently 1 or 2; or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1, wherein R.sup.1 is a furan, thiophene, pyrrole, thiazole, imidazole pyrazole, isoxazole, isothiazole, oxadiazole, triazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, or triazine, and each hydrogen in R.sup.1 is optionally replaced by R.sup.3.

3. An enantiomerically pure compound of formula 1a ##STR00131## wherein: Y is CH; R.sup.1 is pyrazole; and each hydrogen in R.sup.1 is optionally replaced by R.sup.3; each R.sup.3 is independently 3-12 membered heteroalicyclic, and each hydrogen in R.sup.3 is optionally replaced by R.sup.8; each R.sup.8 is independently halogen, C.sub.1-12 alkyl, C.sub.2-12 alkenyl, C.sub.2-12 alkynyl, C.sub.3-12 cycloalkyl, C.sub.6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, --NH.sub.2, --CN, --OH, --O--C.sub.1-12 alkyl, --O--(CH.sub.2).sub.nC.sub.3-12 cycloalkyl, --O--(CH.sub.2).sub.nC.sub.6-12 aryl, --O--(CH.sub.2).sub.n(3-12 membered heteroalicyclic) or --O--(CH.sub.2).sub.n(5-12 membered heteroaryl); and each hydrogen in R.sup.8 is optionally replaced by R.sup.11; each R.sup.11 is independently halogen, C.sub.1-12 alkyl, C.sub.3-12 cycloalkyl, C.sub.6-12 aryl, 3-12 membered heteroalicyclic, 5-12 membered heteroaryl, --O--C.sub.1-12 alkyl, --O--(CH.sub.2).sub.nC.sub.3-12 cycloalkyl, --O--(CH.sub.2).sub.nC.sub.6-12 aryl, --O--(CH.sub.2).sub.n(3-12 membered heteroalicyclic), --O--(CH.sub.2).sub.n(5-12 membered heteroaryl) or --CN, and each hydrogen in R.sup.11 is optionally substituted by halogen, --OH, --CN, --C.sub.1-12 alkyl which may be partially or fully halogenated, or --O--C.sub.1-12 alkyl which may be partially or fully halogenated; and each n is independently 0, 1, 2, 3 or 4; or a pharmaceutically acceptable salt thereof.

4. An enantiomerically pure compound selected from the group consisting of 3[(R)-1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-[1-(1-methyl-piperidi- n-4-yl)-1H-pyrazol-4-yl]-pyridin-2-ylamine; 1-[4-(4-{6-Amino-5-[(R)-1-(2,6-dichloro-3-fluoro-phenyl]-ethoxy]-pyridin-- 3-yl}-pyrazol-1-yl)-piperidin-1-yl]-2-hydroxy-ethanone; and 3-[(R)-1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-py- razol-4-yl)-pyridin-2-ylamine; or a pharmaceutically acceptable salt thereof.
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