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US 9,255,072 B2Granted
Pyrazole compounds and thiazole compounds as protein kinases inhibitors
AssigneeNational Health Rsearch Institutes
InventorsWeir-Torn Jiaang, Tsu-An Hsu, Wen-Hsing Lin, Yu-Sheng Chao
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Abstract
A compound of formula (I): wherein A, B, D, X, Y, R1, R2, R3, m, p, and q are defined herein. Also disclosed is a method for inhibiting FMS-like tyrosine kinase 3, aurora kinase, or vascular endothelial growth factor receptor.
Claims14
A compound of formula (I):
- wherein
- A is CR′, B is N or NR, and D is N or NR, in which R is H or C(O)ORf and R′ is H or alkyl, Rf being C1-C6 alkyl, aryl, or cycloalkyl;
- X is phenylene;
- Y is arylene or heteroarylene;
- R1 is H or alkyl;
- R2 is alkyl, heterocyclyl, or alkoxy when p is 1 and each of the R2 groups, independently, is alkyl, heterocyclyl, or alkoxy when p is 2 or 3;
- R3 is NRaC(O)Rb, CRaRbNRcC(O)NRdRe, NRaS(O2)Rb, NRaC(O)NRbRc, NRaC(O)ORb, or CRaRbNRcC(O)ORd when q is 1;
- and each of the R3 groups, independently, is amino, halo, alkyl, NRaC(O)Rb, CRaRbNRcC(O)NRdRe, NRaS(O2)Rb, NRaC(O)NRbRc, NRaC(O)ORb, or CRaRbNRc—C(O)ORd when q is 2 or 3;
- in which each of Ra, Rb, Rc, Rd, and Re, independently, is H, alkyl, cyclyl, heterocyclyl, aryl, heteroaryl, arylalkyl, or heteroalkyl;
- m is 1;
- p is 1, 2, 3;
- and
- q is 1, 2, 3.
10 more elements
A compound, wherein the compound is
- N1-[3-(4-aminophenyl)-1H-5-pyrazolyl]-4-(4-methylpiperazino) benzamide;
- N1-3-[3-(benzoylamino)phenyl]-1H-5-pyrazolyl-4-(4-methylpiperazino) benzamide;
- N1-(3-3-[(phenylsulfonypl)amino]phenyl-1H-5-pyrazolyl)-4-(4-methylpiperazino)benzamide;
- N1-(4-methyl-3-{4-[({[(5-methyl-3-isoxazolyl)amino]carbonyl}amino) methyl]phenyl}-1H-5-pyrazolyl)-4-(4-methylpiperazino)benzamide;
- N1-(3-4-[([5-(tert-butyl)-3-isoxazolyl]aminocarbonyl)amino]phenyl-1H-5-pyrazolyl)-4-(2-morpholinoethoxy)benzamide;
- N1-(3-4-[([5-(tert-butyl)-3-isoxazolyl]aminocarbonyl)amino]-3-methylphenyl-1H-5-pyrazolyl)-4-[(4-methylpiperazino)methyl]benzamide;
- N1-[3-(4-[([5-(tert-butyl)-3-isoxazolyl]aminocarbonyl)amino]methylphenyl)-1H-5-pyrazolyl]-4-[(4-methylpiperazino)methyl]benzamide;
- Phenyl-N-[4-(5-[4-(4-methylpiperazino)benzoyl]amino-1H-3-pyrazolyl)phenyl]carbamate;
- (5-Methyl-3-isoxazolyl)methyl-N-[4-(5-[4-(2-morpholinoethoxy)benzoyl]amino-1H-3-pyrazolyl)benzyl]carbamate;
- N1-[3-(5-[2-methyl-6-(4-methylpiperazino)-4-pyrimidinyl]amino-1H-3-pyrazolyl)phenyl]-1-benzenesulfonamide;
- N-[5-(tert-butyl)-3-isoxazolyl]-N′-4-[5-(6-[4-(2-hydroxyethyl)piperazino]-2-methyl-4-pyrimidinylamino)-1H-3-pyrazolyl]benzylurea;
- (5-Methyl-3-isoxazolyl)methyl-N-4-[5-(6-[4-(2-hydroxyethyl)piperazino]-2-methyl-4-pyrimidinylamino)-1H-3-pyrazolyl]benzylcarbamate;
- N-(5-methyl-3-isoxazolyl)-N′-[4-(2-[2-methyl-6-(4-methylpiperazino)-4-pyrimidinyl]amino-1,3-thiazol-5-yl)phenyl]urea;
- N1-5-[4-([(5-methyl-3-isoxazolyl)amino]carbonylamino)phenyl]-1,3-thiazol-2-yl-4-(2-morpholinoethoxy)benzamide;
- N-(5-{4-[3-(5-Ethyl-isoxazol-3-yl)-ureido]-3-methyl-phenyl}-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-benzamide;
- 5-{4-[3-(5-Ethyl-isoxazol-3-yl)-ureido]-3-methyl-phenyl}-3-[4-(2-morpholin-4-yl-ethoxy)-benzoylamino]-pyrazole-1-carboxylic acid ethyl ester;
- N-(5-{4-[3-(5-Cyclopropyl-isoxazol-3-yl)-ureidomethyl]-phenyl}-2H-pyrazol-3-yl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide;
- N-(5-{4-[3-(5-Cyclopropyl-isoxazol-3-yl)-ureidomethyl]-phenyl}-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-benzamide;
- N-(5-{4-[3-(5-Ethyl-isoxazol-3-yl)-ureidomethyl]-phenyl}-2H-pyrazol-3-yl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide;
- N1-(3-4-[([(5-cyclopropyl-3-isoxazolyl)amino]carbonylamino)methyl]phenyl-1H -5-pyrazolyl)-4-[(4-methylpiperazino)methyl]benzamide;
- 1-(5-Ethyl-isoxazol-3-yl)-3-(4-{2-[6-(4-ethyl-piperazin-1-yl)-2-methyl-pyrimidin-4-ylamino]-thiazol-5-yl}-phenyl)-urea;
- or
- 1-(4-{2-[6-(3-Amino-pyrrolidin-1-yl)-2-methyl-pyrimidin-4-ylamino]-thiazol-5-yl}-phenyl)-3-(5-ethyl-isoxazol-3-yl)-urea.
20 more elements
A compound of formula (I):
- wherein
- A is CH, B is NH, and D is N;
- X is phenylene;
- Y is pyrimidinylene;
- R1 is H or alkyl;
- R2 is alkyl, halo, heteroalkyl, alkoxyalkyl, heterocyclyl, alkoxy, or amino;
- R3 is alkyl, halo, amino, C(O)NRaRb, CRaRbNRcC(O)NRdRe, CRaRbNRcC(O)ORd, CRaRbNRcS(O)Rd, CRaRbNRcS(O2)Rd, NRaRb, NRaC(O)NRbRc, NRaS(O2)Rb, NRaC(O)Rb, NRaC(O)ORb, or S(O2)NRaRb, in which each of Ra, Rb, Rc, Rd, and Re, independently, is H, alkyl, cyclyl, heterocyclyl, aryl, heteroaryl, arylalkyl, or heteroalkyl;
- m is 0;
- p is 0, 1, 2, 3;
- and
- q is 1, 2, 3.
8 more elements
A compound of formula (I):
- wherein
- A is S, B is CR′, and D is N, in which R′ is H or alkyl;
- X is phenylene;
- Y is pyrimidinylene;
- R1 is H or alkyl;
- R2 is alkyl, halo, heteroalkyl, alkoxyalkyl, heterocyclyl, alkoxy, or amino;
- R3 is alkyl, halo, amino, NRaRb, NRaC(O)NRbRc, NRaS(O2)Rb, or NRaC(O)Rb, in which each of Ra, Rb, and Rc, independently, is H, alkyl, cyclyl, heterocyclyl, aryl, heteroaryl, arylalkyl, or heteroalkyl;
- m is 0;
- p is 0, 1, 2, 3;
- and
- q is 1,2,3.
8 more elements
Dependencies are inferred from the claim text.