Back to results
US 2004/0023992 A1Published application
Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors
AssigneeBristol-Myers Squibb Company
InventorsJagabandhu Das, Chunjian Liu, Robert V. Moquin, Katerina Leftheris
Life of this patent
Estimating the term…
Abstract
Compounds having the formula (I), where all substituents are as defined herein, 1 and pharmaceutically acceptable salts, prodrugs, and solvates thereof, are useful as kinase inhibitors.
Claims19
A compound having the formula (I):
- 148
- or a pharmaceutically-acceptable salt, prodrug, or solvate thereof, wherein:
- Y is —C(═O)NR1—, —NR1C(═O)—, —NR1C(═O)NR1—, —NR1SO2—, —SO2NR1—, —C(═O)—, —OC(═O)—, or —CO2—;
- B is selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, hydroxy, alkoxy, aryl, cycloalkyl, heteroaryl, and heterocyclo;
- or when Y is —C(═O)NR1—, B also may be selected from —C(═O)R8, —C(═O)NR8R9, and —CO2R8,
- R1 is hydrogen, C1-4alkyl, or substituted C1-4alkyl;
- R2 is hydrogen or C1-4alkyl;
- R3 is hydrogen, methyl, perfluoromethyl, hydroxy, methoxy, halogen, cyano, NH2, or NH(CH3);
- R4 is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, cycloalkyl, heteroaryl, or heterocyclo;
- R5 is selected from hydrogen, halogen, cyano, alkyl, substituted alkyl, —C(═O)R11, —CO2R11, —S(═O)R12, —SO2R12, —SO3R12, —OR11, —SR11, —NR11R12, —C(═O)NR11R12, —NR11C(═O)R12, NR11CO2R12, —NR11SO2R12, —SO2NR11R12, cycloalkyl, aryl, heterocyclo and heteroaryl;
- R6 is selected from halogen, cyano, nitro, A1-R13, -A1-O-A2-R13, -A1-S-A2-R13, -A1-C(═O)-A2-R13, -A1-OC(═O)-A2-R13, -A1-S(═O)-A2-R13, -A1-SO2-A2-R13, -A1-CO2-A2-R13, -A1-NR13-A2-R14, -A1-NR15C(═O)-A2-R13, -A1-NR15C(═O)NR16-A2-R13, -A1-NR15CO2-A2-R13, -A1-NR15SO2-A2-R13, -A1-NR15SO2NR16-A2-R13, -A1-SO2NR15-A2-R13, and -A1-C(═O)NR15-A2-R13;
- A1 is —(CR17R18)r—;
- A2 is —(CR19R20)s—;
- R8 and R9 are selected from hydrogen, alkyl, substituted alkyl, aryl, cycloalkyl, heteroaryl, and heterocyclo, or when attached to the same nitrogen atom may together form a heteroaryl or heterocyclo ring;
- R1, R12, R13, and R14 are selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, cycloalkyl, heteroaryl, and heterocyclo, or when attached to the same nitrogen atom may form a heteroaryl or heterocyclo ring, provided that when R12 or R13 is attached to a sulfonyl group (as in —S(═O)R12, —SO2R12, —SO3R12, -A1-S(═O)R13, -A1—SO2R13, and -A1-SO3R13), R12 and R13 are not hydrogen;
- R15 and R16 are selected from hydrogen, C1-4alkyl, hydroxy, hydroxyC1-4alkyl, and aminoC1-4alkyl;
- R17, R18, R19, and R20 are selected from hydrogen, C1-4alkyl, halogen, cyano, hydroxy, hydroxyC1-4alkyl, haloC1-4alkyl, C1-4haloalkoxy, amino, C1-4alkylamino, and aminoC1-4alkyl;
- m is 0, 1 or 2;
- and
- r and s are selected from 0, 1, 2, 3, and 4.
17 more elements
A compound of formula (Ib),
- 150
- or a pharmaceutically-acceptable salt, prodrug, or solvate thereof, wherein
- B is selected from hydroxy, alkoxy, —C(═O)R8, —C(═O)NR8R9, —CO2R8, —(CH2)n—C3-7cycloalkyl, —(CH2)n-heteroaryl, —(CH2)n-heterocyclo, and —(CH2)n-phenyl, wherein each cyclic group B is optionally substituted with one to three R7;
- R5a and R5b are independently hydrogen, C1-4alkyl, substituted C1-4alkyl, halogen, C1-4haloalkoxy, C1-4haloalkyl, hydroxy, C1-4alkoxy, or cyano;
- R6 is alkyl, —O—(CH2)r—R13, —NR13R14, aryl, cycloalkyl, heterocyclo, or heteroaryl, wherein when R6 is alkyl, aryl, cycloalkyl, heterocyclo, or heteroaryl, R6 is optionally substituted with one to three groups selected from alkyl, substituted alkyl, halogen, cyano, nitro, hydroxy, alkoxy, haloalkoxy, amino, alkylamino, phenyl, benzyl, phenyloxy, and benzyloxy;
- R7 and R21 are independently selected from C1-6alkyl, substituted C1-4alkyl, halogen, haloalkyl, haloalkoxy, cyano, nitro, hydroxy, C1-4alkoxy, phenyl, benzyl, phenyloxy, benzyloxy, NH2, NH(C1-4alkyl), N(C1-4alkyl)2, C3-7cycloalkyl, and five or six membered heteroaryl or heterocycle;
- R8 and R9 are selected from hydrogen, alkyl, substituted alkyl, aryl, cycloalkyl, heteroaryl, and heterocyclo, or when attached to the same nitrogen atom may form a heteroaryl or heterocyclo ring;
- R13 and R14 are selected from hydrogen, alkyl, substituted alkyl, cyano, aryl, cycloalkyl, heteroaryl, or heterocyclo, or together form a heterocyclo or heteroaryl ring;
- r is 0, 1, 2, 3 or 4;
- and
- n is 0, 1, 2, 3, or 4.
8 more elements
Dependencies are inferred from the claim text.