RU2001130452A - Cyclic Protein Tyrosine Kinase Inhibitors - Google Patents
Cyclic Protein Tyrosine Kinase InhibitorsInfo
- Publication number
- RU2001130452A RU2001130452A RU2001130452/04A RU2001130452A RU2001130452A RU 2001130452 A RU2001130452 A RU 2001130452A RU 2001130452/04 A RU2001130452/04 A RU 2001130452/04A RU 2001130452 A RU2001130452 A RU 2001130452A RU 2001130452 A RU2001130452 A RU 2001130452A
- Authority
- RU
- Russia
- Prior art keywords
- amino
- thiazolecarboxamide
- methyl
- trimethylphenyl
- carbonyl
- Prior art date
Links
- 125000004122 cyclic group Chemical group 0.000 title 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title 1
- -1 cycloalkenylalkyl Chemical group 0.000 claims 233
- 125000003277 amino group Chemical group 0.000 claims 126
- 125000000217 alkyl group Chemical group 0.000 claims 106
- 229910052739 hydrogen Inorganic materials 0.000 claims 99
- 239000001257 hydrogen Substances 0.000 claims 99
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 79
- 150000001875 compounds Chemical class 0.000 claims 77
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 73
- 125000003118 aryl group Chemical group 0.000 claims 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 49
- 150000002431 hydrogen Chemical class 0.000 claims 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims 43
- 125000001424 substituent group Chemical group 0.000 claims 37
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 31
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 29
- 150000002367 halogens Chemical class 0.000 claims 28
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 229910052757 nitrogen Inorganic materials 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 125000004450 alkenylene group Chemical group 0.000 claims 18
- 125000002947 alkylene group Chemical group 0.000 claims 18
- 125000003342 alkenyl group Chemical group 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 150000002829 nitrogen Chemical group 0.000 claims 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 10
- 229910052717 sulfur Chemical group 0.000 claims 10
- 239000011593 sulfur Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000001495 ethyl group Chemical compound [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 9
- 239000001301 oxygen Substances 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 7
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000004429 atoms Chemical group 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 5
- 125000006309 butyl amino group Chemical compound 0.000 claims 5
- 125000006255 cyclopropyl carbonyl group Chemical compound [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- QFJCIRLUMZQUOT-HPLJOQBZSA-N Sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 229960002930 sirolimus Drugs 0.000 claims 4
- 210000001744 T-Lymphocytes Anatomy 0.000 claims 3
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 3
- 125000004419 alkynylene group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 229940113083 morpholine Drugs 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- FIEBFNVGGCDAMT-UHFFFAOYSA-N 2-(adamantane-1-carbonylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)C23CC4CC(CC(C4)C2)C3)SC=1C(=O)NC1=C(C)C=C(C)C=C1C FIEBFNVGGCDAMT-UHFFFAOYSA-N 0.000 claims 2
- SVPCWVYSRVATHE-UHFFFAOYSA-N 2-amino-4-phenyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)C1=C(C=2C=CC=CC=2)N=C(N)S1 SVPCWVYSRVATHE-UHFFFAOYSA-N 0.000 claims 2
- 125000001847 2-phenylcyclopropyl group Chemical compound [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims 2
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims 2
- ZWTABFNLYYWWKK-UHFFFAOYSA-N 4-methyl-2-[(4-methylphenyl)carbamoylamino]-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(C)=CC=2C)C)=C(C)N=C1NC(=O)NC1=CC=C(C)C=C1 ZWTABFNLYYWWKK-UHFFFAOYSA-N 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 101710039984 9.1 Proteins 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 101710040446 CD40 Proteins 0.000 claims 2
- 102100013137 CD40 Human genes 0.000 claims 2
- 101710003804 CD40LG Proteins 0.000 claims 2
- 102100003729 CD40LG Human genes 0.000 claims 2
- AQEFLFZSWDEAIP-UHFFFAOYSA-N Di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 2
- 229940099538 Rapamune Drugs 0.000 claims 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 2
- 150000003869 acetamides Chemical compound 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 230000001028 anti-proliferant Effects 0.000 claims 2
- 108090001123 antibodies Proteins 0.000 claims 2
- 102000004965 antibodies Human genes 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004693 haloalkylthiocarbonyl group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 230000001404 mediated Effects 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drugs Drugs 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical compound [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- REMZLTYVNBKZHE-UHFFFAOYSA-N tert-butyl N-[4-methyl-5-(prop-2-ynylcarbamoyl)-1,3-thiazol-2-yl]carbamate Chemical compound CC=1N=C(NC(=O)OC(C)(C)C)SC=1C(=O)NCC#C REMZLTYVNBKZHE-UHFFFAOYSA-N 0.000 claims 2
- PTZMYYBOYCLZLR-UHFFFAOYSA-N tert-butyl N-[4-methyl-5-[(3-methyl-4-propan-2-ylphenyl)carbamoyl]-1,3-thiazol-2-yl]carbamate Chemical compound C1=C(C)C(C(C)C)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)OC(C)(C)C)S1 PTZMYYBOYCLZLR-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 125000005152 trihalomethanesulfonyl group Chemical group 0.000 claims 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17 Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 1
- 125000001607 1,2,3-triazol-1-yl group Chemical compound [*]N1N=NC([H])=C1[H] 0.000 claims 1
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- MSQCMJUEOFEUQF-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)NC=2C=C3OCOC3=CC=2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C MSQCMJUEOFEUQF-UHFFFAOYSA-N 0.000 claims 1
- DBARUODEPPAYIW-UHFFFAOYSA-N 2-(1-benzofuran-2-carbonylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)C=2OC3=CC=CC=C3C=2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C DBARUODEPPAYIW-UHFFFAOYSA-N 0.000 claims 1
- NXXJZBCDGIPUJC-UHFFFAOYSA-N 2-(1-benzothiophene-2-carbonylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)C=2SC3=CC=CC=C3C=2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C NXXJZBCDGIPUJC-UHFFFAOYSA-N 0.000 claims 1
- IAIMSXQNQHSQSU-UHFFFAOYSA-N 2-(1H-indol-5-ylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)NC=2C=C3C=CNC3=CC=2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C IAIMSXQNQHSQSU-UHFFFAOYSA-N 0.000 claims 1
- JDOKXJGHJJJMNT-UHFFFAOYSA-N 2-(2,2-dimethylpropanoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound N1=C(NC(=O)C(C)(C)C)SC(C(=O)NC=2C(=CC(C)=CC=2C)C)=C1C JDOKXJGHJJJMNT-UHFFFAOYSA-N 0.000 claims 1
- UEBZEOJPXILZGN-UHFFFAOYSA-N 2-(2,2-diphenylethylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(C)=CC=2C)C)=C(C)N=C1NC(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 UEBZEOJPXILZGN-UHFFFAOYSA-N 0.000 claims 1
- BSXWVBPNGVGFRG-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-3-ylmethylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)NCC2OC3=CC=CC=C3OC2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C BSXWVBPNGVGFRG-UHFFFAOYSA-N 0.000 claims 1
- LHKGOAXEOHVSLI-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-ylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)NC=2C=C3OCCOC3=CC=2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C LHKGOAXEOHVSLI-UHFFFAOYSA-N 0.000 claims 1
- USERCIHGHFZDLO-UHFFFAOYSA-N 2-(2-acetamidohexanoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)C(NC(C)=O)CCCC)=NC(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C USERCIHGHFZDLO-UHFFFAOYSA-N 0.000 claims 1
- OPVQZQBNJMZFGA-UHFFFAOYSA-N 2-(2-hydroxyhexanoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)C(O)CCCC)=NC(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C OPVQZQBNJMZFGA-UHFFFAOYSA-N 0.000 claims 1
- DETBKLMNGRXIJF-UHFFFAOYSA-N 2-(2-methoxyethylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCOC)=NC(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C DETBKLMNGRXIJF-UHFFFAOYSA-N 0.000 claims 1
- NMZYKXFEHHAIEC-UHFFFAOYSA-N 2-(3,3-dimethylbutylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound N1=C(NC(=O)NCCC(C)(C)C)SC(C(=O)NC=2C(=CC(C)=CC=2C)C)=C1C NMZYKXFEHHAIEC-UHFFFAOYSA-N 0.000 claims 1
- AOYZBXYIQVKIJV-UHFFFAOYSA-N 2-(3,4-dihydro-1H-isoquinoline-2-carbonylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)N2CC3=CC=CC=C3CC2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C AOYZBXYIQVKIJV-UHFFFAOYSA-N 0.000 claims 1
- YCCKEKNOMVPJAO-UHFFFAOYSA-N 2-(3-butoxypropylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCOCCCC)=NC(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C YCCKEKNOMVPJAO-UHFFFAOYSA-N 0.000 claims 1
- MBSDJXXDWVXNSR-UHFFFAOYSA-N 2-(4-methoxybutylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCCOC)=NC(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C MBSDJXXDWVXNSR-UHFFFAOYSA-N 0.000 claims 1
- ARXRJMSASMFEPZ-UHFFFAOYSA-N 2-(anthracen-1-ylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)NC=2C3=CC4=CC=CC=C4C=C3C=CC=2)SC=1C(=O)NC1=C(C)C=C(C)C=C1C ARXRJMSASMFEPZ-UHFFFAOYSA-N 0.000 claims 1
- NLYRFTNFPYEWCA-UHFFFAOYSA-N 2-(benzylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(C)=CC=2C)C)=C(C)N=C1NC(=O)NCC1=CC=CC=C1 NLYRFTNFPYEWCA-UHFFFAOYSA-N 0.000 claims 1
- ANOOKLPIDKBMTR-UHFFFAOYSA-N 2-(butylcarbamoylamino)-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C ANOOKLPIDKBMTR-UHFFFAOYSA-N 0.000 claims 1
- IMYFBEPPKRILSO-UHFFFAOYSA-N 2-(butylcarbamoylamino)-4-methyl-N-(2-methylnaphthalen-1-yl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=C(C)C=CC2=CC=CC=C12 IMYFBEPPKRILSO-UHFFFAOYSA-N 0.000 claims 1
- KSWRLRDHSKDEAX-UHFFFAOYSA-N 2-(butylcarbamoylamino)-4-methyl-N-(6-methylquinolin-5-yl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=C(C)C=CC2=NC=CC=C12 KSWRLRDHSKDEAX-UHFFFAOYSA-N 0.000 claims 1
- LVNSQAOLBCRQLE-UHFFFAOYSA-N 2-(butylcarbamoylamino)-4-methyl-N-naphthalen-2-yl-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=CC=C(C=CC=C2)C2=C1 LVNSQAOLBCRQLE-UHFFFAOYSA-N 0.000 claims 1
- LJUFPYHBANWZNU-UHFFFAOYSA-N 2-(butylcarbamoylamino)-N-(2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=CC=C(CCC2)C2=C1 LJUFPYHBANWZNU-UHFFFAOYSA-N 0.000 claims 1
- VGYQBWIXVGITCO-UHFFFAOYSA-N 2-(butylcarbamoylamino)-N-(2,6-dimethyl-3-nitrophenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=C(C)C=CC([N+]([O-])=O)=C1C VGYQBWIXVGITCO-UHFFFAOYSA-N 0.000 claims 1
- GYWHLRCIEUMYTA-UHFFFAOYSA-N 2-(butylcarbamoylamino)-N-(2,6-dimethyl-3-propan-2-ylphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=C(C)C=CC(C(C)C)=C1C GYWHLRCIEUMYTA-UHFFFAOYSA-N 0.000 claims 1
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- CJEUAVQNZJMVLD-UHFFFAOYSA-N 2-(butylcarbamoylamino)-N-[4-(dimethylamino)-2,3,5,6-tetramethylphenyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C(=O)NC1=C(C)C(C)=C(N(C)C)C(C)=C1C CJEUAVQNZJMVLD-UHFFFAOYSA-N 0.000 claims 1
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- BTQMHYBZEXSDHT-UHFFFAOYSA-N 2-[(4-methoxy-2-methylphenyl)carbamoylamino]-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(OC)=CC=C1NC(=O)NC1=NC(C)=C(C(=O)NC=2C(=CC(C)=CC=2C)C)S1 BTQMHYBZEXSDHT-UHFFFAOYSA-N 0.000 claims 1
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- HFNZLNNQERXRDD-UHFFFAOYSA-N 2-[(4-tert-butylcyclohexanecarbonyl)amino]-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(C)=CC=2C)C)=C(C)N=C1NC(=O)C1CCC(C(C)(C)C)CC1 HFNZLNNQERXRDD-UHFFFAOYSA-N 0.000 claims 1
- OLOHQNWHBQKIJZ-UHFFFAOYSA-N 2-[(4-tert-butylcyclohexyl)carbamoylamino]-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(C)=CC=2C)C)=C(C)N=C1NC(=O)NC1CCC(C(C)(C)C)CC1 OLOHQNWHBQKIJZ-UHFFFAOYSA-N 0.000 claims 1
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- WAJOHRYOEUELOG-UHFFFAOYSA-N 2-[(5-chloro-4-methoxythiophene-3-carbonyl)amino]-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound COC1=C(Cl)SC=C1C(=O)NC1=NC(C)=C(C(=O)NC=2C(=CC(C)=CC=2C)C)S1 WAJOHRYOEUELOG-UHFFFAOYSA-N 0.000 claims 1
- FVDXSVWXGKDFFF-UHFFFAOYSA-N 2-[(5-chloropyridin-2-yl)carbamoylamino]-4-methyl-N-(2,4,6-trimethylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(C)=CC=2C)C)=C(C)N=C1NC(=O)NC1=CC=C(Cl)C=N1 FVDXSVWXGKDFFF-UHFFFAOYSA-N 0.000 claims 1
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- CJSMRSKBJZEIAA-UHFFFAOYSA-N tert-butyl N-[4-phenyl-5-[(2,4,6-trimethylphenyl)carbamoyl]-1,3-thiazol-2-yl]carbamate Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)C1=C(C=2C=CC=CC=2)N=C(NC(=O)OC(C)(C)C)S1 CJSMRSKBJZEIAA-UHFFFAOYSA-N 0.000 claims 1
- CDZZMXOFVHOKSV-UHFFFAOYSA-N tert-butyl N-[5-(1,4-dioxa-8-azaspiro[4.5]decane-8-carbonyl)-4-methyl-1,3-thiazol-2-yl]carbamate Chemical compound N1=C(NC(=O)OC(C)(C)C)SC(C(=O)N2CCC3(CC2)OCCO3)=C1C CDZZMXOFVHOKSV-UHFFFAOYSA-N 0.000 claims 1
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- LQKPJVCIOQVODS-UHFFFAOYSA-N tert-butyl N-[5-[(2-tert-butyl-4-methylphenyl)carbamoyl]-4-methyl-1,3-thiazol-2-yl]carbamate Chemical compound N1=C(NC(=O)OC(C)(C)C)SC(C(=O)NC=2C(=CC(C)=CC=2)C(C)(C)C)=C1C LQKPJVCIOQVODS-UHFFFAOYSA-N 0.000 claims 1
- WBGFEXDHFKSHFL-UHFFFAOYSA-N tert-butyl N-[5-[(4-cyclohexylphenyl)carbamoyl]-4-methyl-1,3-thiazol-2-yl]carbamate Chemical compound N1=C(NC(=O)OC(C)(C)C)SC(C(=O)NC=2C=CC(=CC=2)C2CCCCC2)=C1C WBGFEXDHFKSHFL-UHFFFAOYSA-N 0.000 claims 1
- FEWAQXNYQQUYHF-UHFFFAOYSA-N tert-butyl N-[5-[(4-methoxyphenyl)carbamoyl]-4-methyl-1,3-thiazol-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)OC(C)(C)C)S1 FEWAQXNYQQUYHF-UHFFFAOYSA-N 0.000 claims 1
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- YKSTWPONCQSRBI-UHFFFAOYSA-N tert-butyl N-methyl-N-[4-methyl-5-[(2,4,6-trimethylphenyl)carbamoyl]-1,3-thiazol-2-yl]carbamate Chemical compound S1C(N(C(=O)OC(C)(C)C)C)=NC(C)=C1C(=O)NC1=C(C)C=C(C)C=C1C YKSTWPONCQSRBI-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical compound [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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US8101629B2 (en) | 2001-08-13 | 2012-01-24 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
JO3429B1 (en) | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | Hiv inhibiting pyrimidines derivatives |
US7638522B2 (en) | 2001-08-13 | 2009-12-29 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino] benzonitrile |
US7265134B2 (en) * | 2001-08-17 | 2007-09-04 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
US6677487B2 (en) * | 2001-08-30 | 2004-01-13 | Pharmacia Corporation | α-haloenamine reagents |
US6825184B2 (en) | 2001-10-18 | 2004-11-30 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-Disubstituted benzo-fused urea compounds |
WO2003037869A1 (en) | 2001-11-01 | 2003-05-08 | Janssen Pharmaceutica N.V. | Amide derivatives as glycogen synthase kinase 3-beta inhibitors |
PL369259A1 (en) | 2001-11-01 | 2005-04-18 | Janssen Pharmaceutica N.V. | Heteroaryl amines as glycogen synthase kinase 3beta inhibitors (gsk3 inhibitors) |
US6693097B2 (en) | 2001-11-30 | 2004-02-17 | Synta Pharmaceuticals Corp. | Pyrimidine compounds |
IL162189A0 (en) * | 2001-11-30 | 2005-11-20 | Synta Pharmaceuticals Corp | Pyrimidine compounds |
MXPA04009541A (en) | 2002-03-29 | 2005-01-25 | Chiron Corp | Substituted benzazoles and use thereof as raf kinase inhibitors. |
US8299108B2 (en) | 2002-03-29 | 2012-10-30 | Novartis Ag | Substituted benzazoles and methods of their use as inhibitors of raf kinase |
NZ537156A (en) * | 2002-05-23 | 2007-06-29 | Cytopia Pty Ltd | Kinase inhibitors |
KR101169964B1 (en) | 2002-05-23 | 2012-08-06 | 와이엠 바이오사이언시즈 오스트레일리아 피티와이 엘티디 | Kinase inhibitors |
AUPS251402A0 (en) * | 2002-05-23 | 2002-06-13 | Cytopia Pty Ltd | Kinase inhibitors |
WO2003099773A1 (en) | 2002-05-24 | 2003-12-04 | Millennium Pharmaceuticals, Inc. | Ccr9 inhibitors and methods of use thereof |
GB0215676D0 (en) | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
US6872724B2 (en) | 2002-07-24 | 2005-03-29 | Merck & Co., Inc. | Polymorphs with tyrosine kinase activity |
AU2003261354A1 (en) * | 2002-08-02 | 2004-02-23 | The Regents Of The University Of California | New uses for inhibitors of inosine monophosphate dehydrogenase |
WO2004014904A1 (en) * | 2002-08-09 | 2004-02-19 | Pfizer Inc. | Antiproliferative 2-(heteroaryl)-aminothiazole compounds, pharmaceutical compositions and methods for their use |
PL208533B1 (en) | 2002-08-09 | 2011-05-31 | Janssen Pharmaceutica Nv | Processes for the preparation of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
KR101173510B1 (en) * | 2002-08-23 | 2012-08-21 | 슬로안-케테링인스티튜트퍼캔서리서치 | Synthesis of epothilones intermediates thereto analogues and uses thereof |
US7537891B2 (en) | 2002-08-27 | 2009-05-26 | Bristol-Myers Squibb Company | Identification of polynucleotides for predicting activity of compounds that interact with and/or modulate protein tyrosine kinases and/or protein tyrosine kinase pathways in breast cells |
EP1572957A4 (en) | 2002-08-27 | 2007-10-10 | Bristol Myers Squibb Pharma Co | Identification of polynucleotides for predicting activity of compounds that interact with and/or modulate protein tyrosine kinases and/or protein tyrosine kinase pathways in breast cells |
EP1558609A4 (en) * | 2002-10-30 | 2008-05-28 | Merck & Co Inc | Kinase inhibitors |
KR100866456B1 (en) | 2002-11-18 | 2008-10-31 | 케모센트릭스 | Aryl sulfonamides |
US7741519B2 (en) | 2007-04-23 | 2010-06-22 | Chemocentryx, Inc. | Bis-aryl sulfonamides |
US7420055B2 (en) | 2002-11-18 | 2008-09-02 | Chemocentryx, Inc. | Aryl sulfonamides |
US7227035B2 (en) | 2002-11-18 | 2007-06-05 | Chemocentryx | Bis-aryl sulfonamides |
US7169771B2 (en) | 2003-02-06 | 2007-01-30 | Bristol-Myers Squibb Company | Thiazolyl-based compounds useful as kinase inhibitors |
BRPI0407329A (en) | 2003-02-07 | 2006-01-10 | Janssen Pharmaceutica Nv | Pyrimidine Derivatives for the Prevention of HIV Infection |
MXPA05008309A (en) * | 2003-02-10 | 2005-09-20 | Amgen Inc | Vanilloid receptor ligands and their use in treatments. |
CL2004000303A1 (en) | 2003-02-20 | 2005-04-08 | Tibotec Pharm Ltd | COMPOUNDS DERIVED FROM PYRIMIDINS AND TRIAZINES; PREPARATION PROCESS; PHARMACEUTICAL COMPOSITION; AND ITS USE TO INHIBIT HIV REPLICATION. |
CA2520124A1 (en) | 2003-03-28 | 2004-10-14 | Chiron Corporation | Use of benzazole compounds for immunopotentiation |
US7427683B2 (en) | 2003-04-25 | 2008-09-23 | Ortho-Mcneil Pharmaceutical, Inc. | c-fms kinase inhibitors |
US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
US7790724B2 (en) | 2003-04-25 | 2010-09-07 | Janssen Pharmaceutica N.V. | c-fms kinase inhibitors |
WO2004096795A2 (en) * | 2003-04-25 | 2004-11-11 | 3-Dimensional Pharmaceuticals, Inc. | C-fms kinase inhibitors |
US7652044B2 (en) | 2003-06-03 | 2010-01-26 | Novartis A.G. | P-38 inhibitors |
SI2298743T1 (en) | 2003-06-26 | 2012-12-31 | Novartis Ag | 5-membered heterocycle-based P38 kinase inhibitors |
TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
US20050009891A1 (en) * | 2003-07-09 | 2005-01-13 | Lee Francis Y. | Combination of SRC Kinase inhibitors and chemotherapeutic agents for the treatment of proliferative diseases |
DE602004017654D1 (en) | 2003-07-16 | 2008-12-18 | Janssen Pharmaceutica Nv | TRIAZOLOPYRIMIDINE DERIVATIVES AS INHIBITORS OF GLYCOGEN SYNTHASE KINASE-3 |
EP2256106B1 (en) | 2003-07-22 | 2015-05-06 | Astex Therapeutics Limited | 3,4-disubstituted 1H-pyrazole compounds and their use as cyclin dependent kinases (CDK) and glycogen synthase kinase-3 (GSK-3) modulators |
CA2539726A1 (en) * | 2003-09-24 | 2005-05-06 | Vertex Pharmaceuticals Incorporated | 4-azole substituted imidazole compositions useful as inhibitors or c-met receptor tyrosine kinase |
WO2005033079A1 (en) | 2003-09-30 | 2005-04-14 | Eisai Co., Ltd. | Novel antifungal agent comprising heterocyclic compound |
ES2327418T3 (en) | 2003-10-16 | 2009-10-29 | Novartis Vaccines And Diagnostics, Inc. | BENZAZOLES REPLACED AND USE OF THE SAME AS INHIBITORS OF THE QUINASA RAF. |
CA2545259A1 (en) | 2003-11-10 | 2005-05-26 | Synta Pharmaceuticals, Corp. | Heteroaryl-hydrazone compounds |
US7338951B2 (en) | 2003-11-10 | 2008-03-04 | Synta Pharmaceuticals Corp. | Pyridine compounds |
CA2545340A1 (en) | 2003-11-10 | 2005-05-26 | Synta Pharmaceuticals, Corp. | Fused heterocyclic compounds |
GB2423083B (en) * | 2003-12-03 | 2007-07-11 | Cytopia Res Pty Ltd | Azole-based kinase inhibitors |
ZA200602138B (en) * | 2003-12-03 | 2007-06-27 | Cytopia Res Pty Ltd | Azole-based kinase inhibitors |
CA2554201C (en) * | 2004-01-21 | 2015-04-14 | Emory University | Compositions and use of tyrosine kinase inhibitors to treat pathogenic infection |
ES2791303T3 (en) * | 2004-01-30 | 2020-11-03 | Vertex Pharma | ATP-binding cassette transporter modulators intermediate |
EP1711497A1 (en) * | 2004-01-30 | 2006-10-18 | AB Science | 2-(3-substituted-aryl)amino-4-aryl-thiazoles as tyrosine kinase inhibitors |
CN1980909B (en) * | 2004-02-06 | 2010-08-25 | 布里斯托尔-迈尔斯·斯奎布公司 | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
US20050215795A1 (en) * | 2004-02-06 | 2005-09-29 | Bang-Chi Chen | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
US7491725B2 (en) | 2004-02-06 | 2009-02-17 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
TWI338004B (en) * | 2004-02-06 | 2011-03-01 | Bristol Myers Squibb Co | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
US7652146B2 (en) * | 2004-02-06 | 2010-01-26 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-carboxamides useful as kinase inhibitors |
US7534798B2 (en) | 2004-02-11 | 2009-05-19 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
US7384968B2 (en) * | 2004-04-01 | 2008-06-10 | Pfizer Inc. | Thiazole-amine compounds for the treatment of neurodegenerative disorders |
WO2005103022A1 (en) * | 2004-04-20 | 2005-11-03 | Transtech Pharma, Inc. | Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators |
US7550499B2 (en) * | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
WO2006115509A2 (en) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Small molecule immunopotentiators and assays for their detection |
CA2573999A1 (en) * | 2004-07-16 | 2006-04-06 | Sunesis Pharmaceuticals, Inc. | Thienopyrimidines useful as aurora kinase inhibitors |
US7410988B2 (en) | 2004-08-13 | 2008-08-12 | Genentech, Inc. | 2-Amido-thiazole-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
EA200700707A1 (en) | 2004-09-22 | 2007-08-31 | Х. Лундбекк А/С | DERIVATIVES 2-ACYLAMINOTHIAZOLE |
US20060069101A1 (en) * | 2004-09-27 | 2006-03-30 | Kim Kyoung S | Prodrugs of protein tyrosine kinase inhibitors |
NZ555289A (en) * | 2004-10-22 | 2010-10-29 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
US7645755B2 (en) * | 2004-10-22 | 2010-01-12 | Janssen Pharmaceutical N.V. | Inhibitors of c-fms kinase |
TW200628156A (en) * | 2004-11-04 | 2006-08-16 | Bristol Myers Squibb Co | Combination of a SRC kinase inhibitor and a BCR-ABL inhibitor for the treatment of proliferative diseases |
WO2006053109A1 (en) | 2004-11-10 | 2006-05-18 | Synta Pharmaceuticals Corp. | Heteroaryl compounds |
TW200630363A (en) | 2004-11-10 | 2006-09-01 | Synta Pharmaceuticals Corp | Process for preparing trisubstituted pyrimidine compounds |
JP2008519850A (en) | 2004-11-10 | 2008-06-12 | シンタ ファーマシューティカルズ コーポレーション | IL-12 modulating compound |
SE0402762D0 (en) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
SE0402763D0 (en) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Nitro indazole derivatives |
US7851466B2 (en) | 2004-11-19 | 2010-12-14 | Synta Pharmaceuticals Corp. | Pyrimidine compounds and uses thereof |
AU2005311251A1 (en) * | 2004-12-01 | 2006-06-08 | Devgen Nv | 5-carboxamido substituted thiazole derivatives that interact with ion channels, in particular with ion channels from the Kv family |
JP5507049B2 (en) | 2004-12-30 | 2014-05-28 | アステックス、セラピューティックス、リミテッド | Medicine |
DE602006020327D1 (en) * | 2005-01-19 | 2011-04-07 | Bristol Myers Squibb Co | 2-PHENOXY-N- (1,3,4-THIADIZOL-2-YL) PYRIDINE-3-AMINDER INHIBITOR FOR THE TREATMENT OF THROMBOEMBOLIC ILLNESSES |
EP1845973B1 (en) | 2005-01-21 | 2015-08-12 | Astex Therapeutics Limited | Pharmaceutical compounds |
AR054425A1 (en) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | PIPERIDIN ADDITION SALTS 4-IL-ACID AMID 4- (2,6-DICLORO-BENZOILAMINO) 1H-PIRAZOL-3-CARBOXILICO. |
BRPI0606480A (en) | 2005-01-21 | 2008-03-11 | Astex Therapeutics Ltd | pharmaceutical compounds |
US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
PE20061394A1 (en) * | 2005-03-15 | 2006-12-15 | Bristol Myers Squibb Co | METABOLITES OF N- (2-CHLORO-6-METHYLPHENYL) -2 - [[6- [4- (2-HYDROXYETHYL) -1-PIPERAZINYL] -2-METHYL-4-PYRIMIDINYL] AMINO] -5-THIAZOLCARBOXAMIDES |
WO2006106711A1 (en) | 2005-03-30 | 2006-10-12 | Eisai R & D Management Co., Ltd. | Antifungal agent containing pyridine derivative |
US20060235006A1 (en) * | 2005-04-13 | 2006-10-19 | Lee Francis Y | Combinations, methods and compositions for treating cancer |
US7674912B2 (en) | 2005-04-25 | 2010-03-09 | H. Lundbeck A/S | Pro-drugs of N-thiazol-2-yl-benzamide derivatives |
FR2885129B1 (en) | 2005-04-29 | 2007-06-15 | Proskelia Sas | NOVEL DERIVATIVES OF UREEE SUBSTITUTED WITH THIAZOLE OR BENZOTHIAZOLE, PROCESS FOR THE PREPARATION THEREOF, THEIR USE AS MEDICAMENTS, THE PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND THE USE THEREOF |
CN102813655A (en) * | 2005-05-05 | 2012-12-12 | 布里斯托尔-迈尔斯斯奎布公司 | Formulations of a SRC/ABL inhibitor |
US20060281788A1 (en) * | 2005-06-10 | 2006-12-14 | Baumann Christian A | Synergistic modulation of flt3 kinase using a flt3 inhibitor and a farnesyl transferase inhibitor |
JP5253159B2 (en) | 2005-06-24 | 2013-07-31 | デューク・ユニヴァーシティ | Direct drug delivery system based on thermoresponsive biopolymer |
DE602006017694D1 (en) * | 2005-06-27 | 2010-12-02 | Bristol Myers Squibb Co | C-LINKED CYCLIC ANTAGONISTS OF THE P2Y1 RECEPTOR SUITABLE FOR THE TREATMENT OF THROMBOTIC SUFFERING |
US7714002B2 (en) * | 2005-06-27 | 2010-05-11 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
ATE502924T1 (en) | 2005-06-27 | 2011-04-15 | Bristol Myers Squibb Co | LINEAR UREA MIMETIC ANTAGONISTS OF THE P2Y1 RECEPTOR FOR THE TREATMENT OF THROMBOSIS |
KR20080027890A (en) * | 2005-06-27 | 2008-03-28 | 브리스톨-마이어스 스큅 컴퍼니 | N-linked heterocyclic antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
EP1919885B1 (en) * | 2005-08-05 | 2010-04-28 | Brystol-Myers Squibb Company | Preparation of 2-amino-thiazole-5-carboxylic-acid derivatives |
WO2007035874A1 (en) * | 2005-09-21 | 2007-03-29 | Bristol-Myers Squibb Company | Oral administration of n-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-1,3-thiazole-5-carboxamide and salts thereof |
WO2007047919A2 (en) | 2005-10-20 | 2007-04-26 | University Of South Florida | Treatment of restenosis and stenosis with dasatinib |
TWI385169B (en) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | Heterocyclic substituted pyridine derivatives and antifungal agent containing same |
CN103626742B (en) * | 2005-11-01 | 2017-04-26 | 塔格根公司 | Bi-aryl meta-pyrimidine inhibitors of kinases |
ATE521608T1 (en) | 2005-11-01 | 2011-09-15 | Array Biopharma Inc | GLUCOKINASE ACTIVATORS |
EP1948820A2 (en) * | 2005-11-04 | 2008-07-30 | Bristol-Myers Squibb Pharma Company | T315a and f317i mutations of bcr-abl kinase domain |
ES2356080T3 (en) * | 2005-11-10 | 2011-04-04 | Bristol-Myers Squibb Pharma Company | MOESINA, CAVEOLINA AND PROTEINA 1 ASSOCIATED WITH YES AS MARKERS OF RESPONSE TO DASATINIB IN CANCERES DE MAMA. |
US20070149523A1 (en) * | 2005-11-14 | 2007-06-28 | Jan Ehlert | Thiazole Analogues and Uses Thereof |
US20100286090A1 (en) * | 2005-11-14 | 2010-11-11 | Bristol-Myers Squibb Company | Treatment of Multiple Myeloma |
US20090099197A1 (en) * | 2005-11-15 | 2009-04-16 | Bristol-Myers Squibb Company | Methods of Identifying and Treating Individuals Exhibiting MDR-1 Overexpression With Protein Tyrosine Kinase Inhibitors and Combinations Thereof |
US7705009B2 (en) * | 2005-11-22 | 2010-04-27 | Hoffman-La Roche Inc. | 4-aminopyrimidine-5-thione derivatives |
AU2006316705B2 (en) | 2005-11-25 | 2011-09-29 | Galapagos Sas | Urea derivatives useful as calcium receptor modulators |
ES2372975T3 (en) * | 2005-12-01 | 2012-01-30 | Bristol-Myers Squibb Company | PROCEDURES FOR IDENTIFICATION AND TREATMENT OF INDIVIDUALS SHOWING CARIOTIPOS. |
US20100004277A1 (en) * | 2006-01-26 | 2010-01-07 | Foldrx Pharmaceuticals, Inc. | Compounds and methods for modulating protein trafficking |
EP2295432A1 (en) * | 2006-02-10 | 2011-03-16 | TransTech Pharma Inc. | Process for the preparation of aminobenzimidazole derivatives |
WO2007106391A1 (en) * | 2006-03-10 | 2007-09-20 | Lymphosign Inc. | Compounds for modulating cell proliferation, compositions and methods related thereto |
US20070219370A1 (en) * | 2006-03-15 | 2007-09-20 | Bristol-Myers Squibb Company | Process for preparing n-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino] -5-thiazolecarboxamide and related metabolites thereof |
WO2007109527A1 (en) * | 2006-03-17 | 2007-09-27 | Bristol-Myers Squibb Company | Methods of identifying and treating individuals exhibiting mutant bcr/abl kinase polypeptides |
US8163746B2 (en) | 2006-04-19 | 2012-04-24 | Astellas Pharma Inc. | Azolecarboxamide derivative |
US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
CA2649739C (en) | 2006-04-20 | 2015-09-01 | Janssen Pharmaceutica N.V. | Inhibitors of c-fms kinase |
KR101367645B1 (en) | 2006-04-20 | 2014-02-27 | 얀센 파마슈티카 엔.브이. | Heterocyclic compounds as inhibitors of c-fms kinase |
EP2016067B1 (en) * | 2006-04-28 | 2012-08-08 | Syngenta Participations AG | Insecticidal compounds |
WO2007138110A2 (en) * | 2006-06-01 | 2007-12-06 | Devgen N.V. | Compounds that interact with ion channels, in particular with ion channels from the kv family |
DK2041093T3 (en) * | 2006-06-28 | 2010-08-02 | Glaxo Group Ltd | For the treatment of GPR38 receptor, diseases mediate useful piperazinyl derivatives |
GB0613674D0 (en) * | 2006-07-10 | 2006-08-16 | Proskelia Sas | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
EP2061772A4 (en) * | 2006-09-11 | 2011-06-29 | Curis Inc | Multi-functional small molecules as anti-proliferative agents |
JP5563300B2 (en) * | 2006-09-11 | 2014-07-30 | キュリス,インコーポレイテッド | Tyrosine kinase inhibitors containing zinc binding moieties |
WO2008036792A2 (en) | 2006-09-22 | 2008-03-27 | Novartis Ag | Method of optimizing the treatment of philadelphia-positive leukemia with abl tyrosine kinase inhibitors |
WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
US7960569B2 (en) * | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
US8227605B2 (en) | 2006-10-31 | 2012-07-24 | Schering Corporation | 2-aminothiazole-4-carboxylic amides as protein kinase inhibitors |
WO2008054702A1 (en) | 2006-10-31 | 2008-05-08 | Schering Corporation | Anilinopiperazine derivatives and methods of use thereof |
AU2007314305B2 (en) | 2006-10-31 | 2013-01-24 | Merck Sharp & Dohme Corp. | 2-aminothiazole-4-carboxylic amides as protein kinase inhibitors |
WO2008076883A2 (en) | 2006-12-15 | 2008-06-26 | Abraxis Bioscience, Inc. | Triazine derivatives and their therapeutical applications |
CN101323629B (en) * | 2007-02-16 | 2011-08-17 | 江苏正大天晴药业股份有限公司 | 4-{6-[5-(2-chlorinde-6- methylaniline formyl)-thiazole-2-amido]-2-methyl pyrimidine-4}-piperazine-1- diethyl methylphosphate |
TW200906825A (en) * | 2007-05-30 | 2009-02-16 | Scripps Research Inst | Inhibitors of protein kinases |
JP5559043B2 (en) * | 2007-06-07 | 2014-07-23 | イントラ−セルラー・セラピーズ・インコーポレイテッド | Novel heterocyclic compounds and uses thereof |
JP5710251B2 (en) * | 2007-06-07 | 2015-04-30 | イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. | Novel heterocyclic compounds and uses thereof |
UA105758C2 (en) | 2007-07-19 | 2014-06-25 | Х. Луннбек А/С | 5-membered heterocyclic amides and related compounds |
US20090076025A1 (en) * | 2007-09-14 | 2009-03-19 | Protia, Llc | Deuterium-enriched dasatinib |
SI2209778T1 (en) | 2007-09-21 | 2012-12-31 | Array Biopharma, Inc. | Pyridin-2 -yl-amino-i, 2, 4 -thiadiazole derivatives as glucokinase activators for the treatment of diabetes mellitus |
JO3240B1 (en) * | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | Inhibitors of c-fms Kinase |
US8067423B2 (en) | 2007-10-23 | 2011-11-29 | Teva Pharmaceutical Industries Ltd. | Polymorphs of dasatinib isopropyl alcohol and process for preparation thereof |
AU2008314922B2 (en) * | 2007-10-24 | 2013-08-29 | Astellas Pharma Inc. | Azolecarboxamide compound or salt thereof |
EP2062578A1 (en) | 2007-11-12 | 2009-05-27 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Novel use of chemical compounds for the treatment of AIDS |
WO2009076373A1 (en) * | 2007-12-10 | 2009-06-18 | Concert Pharmaceuticals Inc. | Heterocyclic kinase inhibitors |
EP2235537A2 (en) * | 2008-01-25 | 2010-10-06 | Bristol-Myers Squibb Pharma Company | Identification of predictive markers of response to dasatinib in human colon cancer |
EP2502907B1 (en) * | 2008-03-27 | 2018-08-29 | Grünenthal GmbH | Substituted 4-aminocyclohexane derivatives |
DE102008031036A1 (en) | 2008-06-30 | 2009-12-31 | Dömling, Alexander, Priv.-Doz. Dr. | Use of 4-aminothiazolpyrimidine derivatives for the treatment of associated organ transplants |
KR20110051214A (en) * | 2008-07-30 | 2011-05-17 | 닛토덴코 가부시키가이샤 | Drug carriers |
US8563742B2 (en) * | 2008-08-29 | 2013-10-22 | High Point Pharmaceuticals, Llc | Substituted aminothiazole derivatives, pharmaceutical compositions, and methods of use |
WO2010056539A1 (en) | 2008-10-29 | 2010-05-20 | E. I. Du Pont De Nemours And Company | Treatment of tailings streams |
US20100113520A1 (en) * | 2008-11-05 | 2010-05-06 | Principia Biopharma, Inc. | Kinase knockdown via electrophilically enhanced inhibitors |
US8685941B2 (en) * | 2008-12-01 | 2014-04-01 | University Of Central Florida Research Foundation, Inc. | Drug composition cytotoxic for pancreatic cancer cells |
US8530492B2 (en) | 2009-04-17 | 2013-09-10 | Nektar Therapeutics | Oligomer-protein tyrosine kinase inhibitor conjugates |
WO2010120388A1 (en) | 2009-04-17 | 2010-10-21 | Nektar Therapeutics | Oligomer-protein tyrosine kinase inhibitor conjugates |
WO2010139981A2 (en) * | 2009-06-03 | 2010-12-09 | Generics [Uk] Limited | Processes for preparing crystalline forms |
KR20120026612A (en) | 2009-06-09 | 2012-03-19 | 아브락시스 바이오사이언스, 엘엘씨 | Benzyl substituted triazine derivatives and their therapeutical applications |
CA2765030C (en) | 2009-06-09 | 2015-10-27 | California Capital Equity, Llc | Triazine derivatives and their therapeutical applications |
US10640457B2 (en) | 2009-12-10 | 2020-05-05 | The Trustees Of Columbia University In The City Of New York | Histone acetyltransferase activators and uses thereof |
CN101845045A (en) * | 2010-02-02 | 2010-09-29 | 南京卡文迪许生物工程技术有限公司 | Novel method for synthesizing dasatinib |
CN101812060B (en) * | 2010-02-02 | 2011-08-17 | 南京卡文迪许生物工程技术有限公司 | Simple novel method for preparing high-purity Sprycel, and intermediate compound |
EP2359813A1 (en) | 2010-02-04 | 2011-08-24 | Ratiopharm GmbH | Pharmaceutical composition comprising N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamid |
CN101948467B (en) * | 2010-05-17 | 2012-07-25 | 苏州波锐生物医药科技有限公司 | Thiazoleamide compound and use thereof for the preparation of anti-malignant tumor medicines |
CA2798578C (en) | 2010-05-21 | 2015-12-29 | Chemilia Ab | Novel pyrimidine derivatives |
CA2806820A1 (en) | 2010-07-30 | 2012-02-02 | Ranbaxy Laboratories Limited | N-methylformamide solvate of dasatinib |
WO2012060847A1 (en) | 2010-11-07 | 2012-05-10 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
CA2822621C (en) * | 2010-12-22 | 2020-12-15 | The Trustees Of Columbia University In The City Of New York | Histone acetyltransferase modulators and uses thereof |
CA2825367C (en) | 2011-01-21 | 2018-09-25 | Sun Pharma Advanced Research Company Ltd. | Diarylacetylene hydrazide containing tyrosine kinase inhibitors |
WO2012118599A1 (en) | 2011-02-28 | 2012-09-07 | Emory University | C-abl tyrosine kinase inhibitors useful for inhibiting filovirus replication |
DK2683643T3 (en) | 2011-03-09 | 2019-08-12 | Richard G Pestell | PROSTATACANCER CELL LINES, SIGNATURES AND APPLICATIONS THEREOF |
US9006241B2 (en) | 2011-03-24 | 2015-04-14 | Noviga Research Ab | Pyrimidine derivatives |
ES2622112T3 (en) | 2011-05-02 | 2017-07-05 | Stichting Vumc | Protection against endothelial barrier dysfunction through inhibition of the tyrosine-related gene Abl kinase (ARG) |
RU2013154412A (en) | 2011-05-10 | 2015-06-20 | Мерк Шарп И Доум Корп. | AMINOPYRIMIDINES AS SYC INHIBITORS |
US9120785B2 (en) | 2011-05-10 | 2015-09-01 | Merck Sharp & Dohme Corp. | Pyridyl aminopyridines as Syk inhibitors |
US9145391B2 (en) | 2011-05-10 | 2015-09-29 | Merck Sharp & Dohme Corp. | Bipyridylaminopyridines as Syk inhibitors |
CN102898424A (en) * | 2011-07-29 | 2013-01-30 | 江苏奥赛康药业股份有限公司 | Novel polymorphs of dasatinib, and preparation method thereof |
WO2013065063A1 (en) | 2011-11-03 | 2013-05-10 | Cadila Healthcare Limited | Anhydrous form of dasatinib, process for its preparation and its use |
WO2013082458A1 (en) | 2011-12-02 | 2013-06-06 | The Regents Of The University Of California | Reperfusion protection solution and uses thereof |
NZ630288A (en) | 2012-04-20 | 2015-08-28 | Shilpa Medicare Ltd | Process for preparing dasatinib monohydrate |
WO2013170118A1 (en) | 2012-05-11 | 2013-11-14 | Abbvie Inc. | Thiazolecarboxamide derivatives for use as nampt inhibitors |
AU2013262977A1 (en) | 2012-05-14 | 2015-01-22 | Prostagene, Llc | Using modulators of CCR5 for treating cancer |
RU2650524C2 (en) * | 2012-06-15 | 2018-04-16 | Басф Се | Multicomponent crystals comprising dasatinib and selected cocrystal formers |
CN104736144B (en) | 2012-07-27 | 2019-02-01 | 艾祖米科技有限公司 | Outlet inhibitor combination and the method treated using this composition |
JOP20180012A1 (en) | 2012-08-07 | 2019-01-30 | Janssen Pharmaceutica Nv | Sulfonylation process using nonafluorobutanesulfonyl fluoride |
EP2882757B1 (en) | 2012-08-07 | 2016-10-05 | Janssen Pharmaceutica, N.V. | Process for the preparation of heterocyclic ester derivatives |
CA2882088C (en) | 2012-08-23 | 2021-11-23 | Alios Biopharma, Inc. | Compounds for the treatment of paramoxyvirus viral infections |
WO2014039899A1 (en) | 2012-09-10 | 2014-03-13 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
CN103788085B (en) * | 2012-10-31 | 2016-09-07 | 复旦大学 | 2-(quinazoline-4-amino)-5-thiazole carboxamides analog derivative and bio-pharmaceutical purposes thereof |
CZ306598B6 (en) | 2012-12-06 | 2017-03-22 | Zentiva, K.S. | A method of preparation and purification of new and known polymorphs and dasatinib solvates |
WO2014102759A2 (en) | 2012-12-31 | 2014-07-03 | Ranbaxy Laboratories Limited | Process for the preparation of dasatinib and its intermediates |
US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
CN104151321B (en) * | 2013-05-15 | 2016-09-07 | 复旦大学 | N-(2-chloro-6-aminomethyl phenyl)-2 [(2-methylpyrimidine-4-base) amino] thiazole-5-methanamide compound and its production and use |
SG11201509303WA (en) * | 2013-05-23 | 2015-12-30 | Kalvista Pharmaceuticals Ltd | Heterocyclic derivates |
CN104225611B (en) * | 2013-06-18 | 2017-06-30 | 天津键凯科技有限公司 | The conjugate of Dasatinib and non-linear configurations polyethylene glycol |
AR096654A1 (en) * | 2013-06-20 | 2016-01-27 | Ab Science | DERIVATIVES OF BENZIMIDAZOL AS SELECTIVE INHIBITORS OF PROTEIN QUINASA |
WO2015011578A1 (en) * | 2013-07-22 | 2015-01-29 | Shilpa Medicare Limited | Dasatinib glucuronate salt and process for preparation thereof |
WO2015011120A2 (en) | 2013-07-25 | 2015-01-29 | Basf Se | Salts of dasatinib in crystalline form |
JP6370377B2 (en) | 2013-07-25 | 2018-08-08 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Amorphous salt of dasatinib |
TWI636047B (en) | 2013-08-14 | 2018-09-21 | 英商卡爾維斯塔製藥有限公司 | Heterocyclic derivatives |
CN103588758A (en) * | 2013-11-04 | 2014-02-19 | 南京大学 | Synthesis and preparation of nitroimidazole derivative containing 1,4-benzdioxan skeleton and application of nitroimidazole derivative in anticancer drugs |
US9636340B2 (en) | 2013-11-12 | 2017-05-02 | Ayyappan K. Rajasekaran | Kinase inhibitors |
IN2013MU03610A (en) | 2013-12-18 | 2015-04-24 | Dharmesh Mahendrabhai Shah | |
CZ306732B6 (en) | 2013-12-19 | 2017-05-31 | Zentiva, K.S. | A method of preparation of the anhydrous polymorphic form of N-6 Dasatinib |
US20170216286A1 (en) | 2014-01-28 | 2017-08-03 | Mayo Foundation For Medical Education And Research | Killing senescent cells and treating senescence-associated conditions using a src inhibitor and a flavonoid |
EP3107544B1 (en) | 2014-02-21 | 2020-10-07 | Principia Biopharma Inc. | Salts and solid form of a btk inhibitor |
AU2015200822A1 (en) | 2014-03-11 | 2015-10-01 | Cerbios-Pharma Sa | Process and intermediates for the preparation of dasatinib |
HU231013B1 (en) | 2014-05-26 | 2019-11-28 | Egis Gyógyszergyár Zrt. | Dasatinib salts |
CA2950485A1 (en) | 2014-06-30 | 2016-01-07 | Basf Se | Multicomponent crystals of dasatinib with menthol or vanillin |
CN104119292A (en) * | 2014-07-23 | 2014-10-29 | 天津市炜杰科技有限公司 | Preparation method of dasatinib intermediate |
RU2702106C2 (en) | 2014-08-26 | 2019-10-04 | Астеллас Фарма Инк. | 2-aminothiazole derivative or salt thereof |
UY36294A (en) | 2014-09-12 | 2016-04-29 | Novartis Ag | COMPOUNDS AND COMPOSITIONS AS QUINASA INHIBITORS |
WO2016059220A1 (en) | 2014-10-16 | 2016-04-21 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Tcr-activating agents for use in the treatment of t-all |
GB201421083D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
EA036269B1 (en) | 2014-12-18 | 2020-10-21 | Принсипиа Биофарма Инк. | Treatment of pemphigus |
PE20171517A1 (en) | 2015-03-13 | 2017-10-20 | Forma Therapeutics Inc | ALPHA-CINAMIDE COMPOSITIONS AND COMPOSITIONS AS HDAC INHIBITORS 8 |
CN104788445B (en) * | 2015-04-10 | 2017-06-23 | 山东新时代药业有限公司 | A kind of synthetic method of Dasatinib intermediate |
CN104974222B (en) * | 2015-06-14 | 2020-06-02 | 深圳市康尔诺生物技术有限公司 | Conjugated peptide compounds as protein tyrosine kinase inhibitors |
US20180305350A1 (en) | 2015-06-24 | 2018-10-25 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
CN106749223B (en) * | 2015-11-25 | 2019-12-20 | 中国科学院广州生物医药与健康研究院 | Tyrosine kinase inhibitor and preparation method and application thereof |
CN106866684B (en) * | 2015-12-10 | 2020-06-09 | 吴耀东 | Macrocyclic derivatives for the treatment of tumors |
WO2017108605A1 (en) | 2015-12-22 | 2017-06-29 | Synthon B.V. | Pharmaceutical composition comprising amorphous dasatinib |
TWI620748B (en) * | 2016-02-05 | 2018-04-11 | National Health Research Institutes | Aminothiazole compounds and use thereof |
US10722484B2 (en) | 2016-03-09 | 2020-07-28 | K-Gen, Inc. | Methods of cancer treatment |
WO2017168454A2 (en) * | 2016-04-02 | 2017-10-05 | Sun Pharma Advanced Research Company Limited | Novel compounds as btk inhibitors |
CN109311847B (en) | 2016-05-31 | 2021-07-06 | 卡尔维斯塔制药有限公司 | Pyrazole derivatives as plasma kallikrein inhibitors |
GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
GB201609603D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide |
IL293621B2 (en) | 2016-06-29 | 2023-09-01 | Principia Biopharma Inc | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
WO2018002958A1 (en) | 2016-06-30 | 2018-01-04 | Sun Pharma Advanced Research Company Limited | Novel hydrazide containing compounds as btk inhibitors |
EP3484876A1 (en) | 2016-07-14 | 2019-05-22 | Pfizer Inc | Novel pyrimidine carboxamides as inhibitors of vanin-1 enzyme |
BR112019005046A2 (en) | 2016-09-19 | 2019-06-18 | Novartis Ag | therapeutic combinations comprising a raf inhibitor and an erk inhibitor |
US20190270735A1 (en) | 2016-10-29 | 2019-09-05 | Cipla Limited | Polymorphs of Dasatinib |
US10800771B2 (en) | 2016-12-01 | 2020-10-13 | Natco Pharma Limited | Process for the preparation of dasatinib polymorph |
CA3044066A1 (en) | 2016-12-13 | 2018-06-21 | Princeton Drug Discovery Inc | Protein kinase inhibitors |
CN106674150A (en) * | 2016-12-28 | 2017-05-17 | 上海应用技术大学 | Dasatinib derivative with anti-tumor activity and application thereof |
IT201700006157A1 (en) | 2017-01-20 | 2018-07-20 | Cerbios Pharma Sa | Co-crystals of an antitumor compound |
IT201700006145A1 (en) | 2017-01-20 | 2018-07-20 | Cerbios Pharma Sa | Co-crystal of an antitumor compound |
EP3600287B1 (en) * | 2017-03-29 | 2023-07-05 | Purdue Research Foundation | Inhibitors of kinase networks and uses thereof |
EP3388430A1 (en) | 2017-04-10 | 2018-10-17 | Technische Universität München | Compound, compound for use in the treatment of a pathological condition, a pharmaceutical composition and a method for preparing said compound |
DK3391907T3 (en) | 2017-04-20 | 2020-03-09 | Iomx Therapeutics Ag | INTRACELLULAR KINASE SIK3, ASSOCIATED WITH RESISTANCE TO ANTITUMOR IMMUNE RESPONSES, AND APPLICATIONS THEREOF |
EP3649126A4 (en) | 2017-07-07 | 2021-04-07 | Biocon Limited | Polymorphic forms of dasatinib |
RU2674443C1 (en) * | 2017-11-16 | 2018-12-10 | Федеральное государственное автономное образовательное учреждение высшего образования "Белгородский государственный национальный исследовательский университет" (НИУ "БелГУ") | Method for inhibiting nuclear factor kappa b with use of 5-hydroxynicotinate 3-(2,2,2-trimethylhydrazinium) potassium propionate in cell culture |
US11234939B2 (en) | 2017-11-29 | 2022-02-01 | Kalvista Pharmaceuticals Limited | Dosage forms comprising a plasma kallikrein inhibitor |
GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
WO2019169135A1 (en) * | 2018-02-28 | 2019-09-06 | University Of Southern California | Compositions and methods for modulating inflammatory and degenerative disorder |
WO2019238817A1 (en) * | 2018-06-13 | 2019-12-19 | University Of Dundee | Bifunctional molecules for targeting rpn11 |
US20210283139A1 (en) * | 2018-06-13 | 2021-09-16 | Amphista Therapeutics Ltd | Bifunctional molecules for targeting uchl5 |
WO2019238886A1 (en) * | 2018-06-13 | 2019-12-19 | University Of Dundee | Bifunctional molecules for targeting usp14 |
TWI831259B (en) | 2018-06-15 | 2024-02-01 | 漢達生技醫藥股份有限公司 | Capsule containing dasatinib lauryl sulfate composition |
CN108929273A (en) * | 2018-06-27 | 2018-12-04 | 合肥医工医药有限公司 | A kind of preparation method of imidazole ethyl vanillic acid ether sodium salt |
WO2020092650A1 (en) * | 2018-10-30 | 2020-05-07 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for modulating t cell exhaustion |
BR112021011894A2 (en) | 2018-12-21 | 2021-09-08 | Daiichi Sankyo Company, Limited | PHARMACEUTICAL COMPOSITION |
CN109438437B (en) * | 2018-12-24 | 2020-07-17 | 深圳市第二人民医院 | Thiazole ring-containing anticancer compound |
KR20230031981A (en) | 2019-05-14 | 2023-03-07 | 프로벤션 바이오, 인코포레이티드 | Methods and compositions for preventing type 1 diabetes |
US11987575B2 (en) | 2019-07-29 | 2024-05-21 | Ascentage Pharma (Suzhou) Co., Ltd. | Tricyclic compounds as BCR-ABL inhibitors |
EP4010333A1 (en) | 2019-08-09 | 2022-06-15 | Kalvista Pharmaceuticals Limited | Plasma kallikrein inhibitors |
CN112409349A (en) * | 2019-08-20 | 2021-02-26 | 湖南华纳大药厂股份有限公司 | Kinase inhibitor, preparation, pharmaceutical composition and application thereof |
CN112402422A (en) * | 2019-08-20 | 2021-02-26 | 湖南华纳大药厂股份有限公司 | Use of fluoro-substituted 2-aminothiazole-5-aromatic carboxamides |
GB201913121D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
GB201913122D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
GB201913123D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
GB201913124D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
JP2023513444A (en) | 2020-01-24 | 2023-03-31 | ナノコピーア リミテッド ライアビリティ カンパニー | Solid amorphous dispersion of dasatinib and uses thereof |
WO2021228983A1 (en) | 2020-05-13 | 2021-11-18 | INSERM (Institut National de la Santé et de la Recherche Médicale) | A pharmaceutical composition comprising an arsenic compound, an inductor of type-1 ifn and a protein kinase inhibitor for treating cancer |
WO2021252917A2 (en) | 2020-06-11 | 2021-12-16 | Provention Bio, Inc. | Methods and compositions for preventing type 1 diabetes |
KR20220054066A (en) * | 2020-10-23 | 2022-05-02 | (주)메디톡스 | Protein kinase inhibitor and use thereof |
US11980619B2 (en) | 2021-07-28 | 2024-05-14 | Nanocopoeia, Llc | Pharmaceutical compositions and crushable tablets including amorphous solid dispersions of dasatinib and uses |
WO2023081923A1 (en) | 2021-11-08 | 2023-05-11 | Frequency Therapeutics, Inc. | Platelet-derived growth factor receptor (pdgfr) alpha inhibitors and uses thereof |
WO2023204642A1 (en) * | 2022-04-20 | 2023-10-26 | (주)메디톡스 | Protein kinase inhibitor and use thereof |
US20230355678A1 (en) | 2022-05-05 | 2023-11-09 | Immatics US, Inc. | Methods for improving t cell efficacy |
CN117820251B (en) * | 2024-03-01 | 2024-05-03 | 南京桦冠生物技术有限公司 | Bis-alpha-keto acid amide compound and composition thereof |
Family Cites Families (130)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3505055A (en) | 1966-12-07 | 1970-04-07 | Uniroyal Inc | Method of controlling plant growth with carboxamidothiazoles |
US3709992A (en) | 1966-12-07 | 1973-01-09 | Us Rubber Co | Fungicidal use of certain carboxamidothiazoles |
US3725427A (en) | 1966-12-07 | 1973-04-03 | Uniroyal Ltd | Certain 2,4-dimethyl-5-carboxamido-thiazoles |
DE2128699A1 (en) | 1971-06-09 | 1973-01-25 | Bayer Ag | THIAZYL URENE, THE METHOD OF MANUFACTURING THEM AND THEIR FUNGICIDAL USE |
US3796800A (en) * | 1971-11-22 | 1974-03-12 | Uniroyal Inc | Anti-inflammatory triazole compositions and methods for using same |
US3896223A (en) | 1971-11-22 | 1975-07-22 | Uniroyal Inc | Anti-inflammatory thiazole compositions and methods for using same |
US3879531A (en) | 1972-07-17 | 1975-04-22 | Uniroyal Inc | 2-aminothiazoles compositions and methods for using them as psychotherapeutic agents |
US3932633A (en) | 1972-12-04 | 1976-01-13 | Uniroyal Inc. | Novel o-triazenobenzamides, in treating aggressive behavior |
JPS57183768A (en) | 1981-05-06 | 1982-11-12 | Kanto Ishi Pharma Co Ltd | 4-methyl-5-(o-carboxyphenyl)carbamoylthiazole derivative and its preparation |
DE3205638A1 (en) | 1982-02-17 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Trisubstituted pyrimidine-5-carboxylic acids and their derivatives, processes for their preparation, and their use as pesticides |
DE3220118A1 (en) * | 1982-05-28 | 1983-12-01 | Bayer Ag, 5090 Leverkusen | ALKYLENE-BRIDGED GUANIDINOTHIAZOLE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
US4649146A (en) | 1983-01-31 | 1987-03-10 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivatives and pharmaceutical composition comprising the same |
US4727073A (en) | 1984-10-01 | 1988-02-23 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives and composition of the same |
JPS62123180A (en) * | 1985-11-21 | 1987-06-04 | Otsuka Pharmaceut Factory Inc | P-aminophenol derivative |
JPS6339868A (en) * | 1986-08-04 | 1988-02-20 | Otsuka Pharmaceut Factory Inc | Di (lower alkyl) phenol derivative |
US4837242A (en) * | 1987-01-20 | 1989-06-06 | Sumitomo Chemical Company, Limited | Thiazoles and pyrazoles as fungicides |
JP2552494B2 (en) | 1987-04-08 | 1996-11-13 | ヘキストジャパン株式会社 | Imidazothiadiazine derivative and method for producing the same |
GB8717068D0 (en) * | 1987-07-20 | 1987-08-26 | Fujisawa Pharmaceutical Co | Nitric ester derivative |
US4877441A (en) * | 1987-11-06 | 1989-10-31 | Sumitomo Chemical Company Ltd. | Fungicidal substituted carboxylic acid derivatives |
HU202728B (en) | 1988-01-14 | 1991-04-29 | Eszakmagyar Vegyimuevek | Synergetic fungicide and acaricide compositions containing two or three active components |
US4970318A (en) | 1988-05-24 | 1990-11-13 | Pfizer Inc. | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
JPH02129171A (en) | 1988-11-08 | 1990-05-17 | Nissan Chem Ind Ltd | Pyrazolecarboxanilide derivative and agent for controlling harmful life |
JPH02275857A (en) | 1989-01-13 | 1990-11-09 | Yoshitomi Pharmaceut Ind Ltd | Pyridine derivative |
US5696270A (en) | 1989-05-23 | 1997-12-09 | Abbott Laboratories | Intermediate for making retroviral protease inhibiting compounds |
US5064825A (en) | 1989-06-01 | 1991-11-12 | Merck & Co., Inc. | Angiotensin ii antagonists |
WO1991000277A1 (en) | 1989-06-30 | 1991-01-10 | E.I. Du Pont De Nemours And Company | Substituted imidazoles |
TW205041B (en) | 1989-08-07 | 1993-05-01 | Fujisawa Pharmaceutical Co | |
DE3934197A1 (en) | 1989-10-13 | 1991-04-18 | Bayer Ag | THIAZOLICARBONIC ACID DERIVATIVES |
JPH04316559A (en) | 1990-11-28 | 1992-11-06 | Nissan Chem Ind Ltd | Pyrazole carboxanilide derivative and fungicide |
AU664392B2 (en) | 1991-10-18 | 1995-11-16 | Monsanto Technology Llc | Fungicides for the control of take-all disease of plants |
DE4138042C2 (en) | 1991-11-19 | 1993-10-14 | Biotechnolog Forschung Gmbh | Epothilones, their production processes and agents containing these compounds |
JPH05345780A (en) | 1991-12-24 | 1993-12-27 | Kumiai Chem Ind Co Ltd | Pyrimidine or triazine derivative and herbicide |
US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
HUT63941A (en) | 1992-05-15 | 1993-11-29 | Hoechst Ag | Process for producing 4-alkyl-substituted pyrimidine-5-carboxanilide derivatives, and fungicidal compositions comprising same |
IL105939A0 (en) | 1992-06-11 | 1993-10-20 | Rhone Poulenc Agriculture | Herbicidal compounds and compositions |
DE4231517A1 (en) | 1992-09-21 | 1994-03-24 | Basf Ag | Carboxylic acid anilides, process for their preparation and compositions containing them for controlling harmful fungi |
HRP921338B1 (en) | 1992-10-02 | 2002-04-30 | Monsanto Co | Fungicides for the control of take-all disease of plants |
EP0603595A1 (en) | 1992-12-04 | 1994-06-29 | Hoechst Aktiengesellschaft | Fibre reactive dyes, method for their preparation and their use |
AU679735B2 (en) | 1993-04-07 | 1997-07-10 | Nissan Chemical Industries Ltd. | Pyrazole derivative |
US5514643A (en) * | 1993-08-16 | 1996-05-07 | Lucky Ltd. | 2-aminothiazolecarboxamide derivatives, processes for preparing the same and use thereof for controlling phytopathogenic organisms |
AU1433695A (en) | 1993-12-29 | 1995-07-17 | E.I. Du Pont De Nemours And Company | Arthropodicidal oxadiazine-, thiadiazine- or triazine-carboxanilides |
IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
US5582167A (en) * | 1994-03-02 | 1996-12-10 | Thomas Jefferson University | Methods and apparatus for reducing tracheal infection using subglottic irrigation, drainage and servoregulation of endotracheal tube cuff pressure |
DE69526790T2 (en) | 1994-06-24 | 2003-03-06 | Euro Celtique Sa | COMPOUNDS TO INHIBIT PHOSPHODIESRERASE IV |
US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
US6080772A (en) * | 1995-06-07 | 2000-06-27 | Sugen, Inc. | Thiazole compounds and methods of modulating signal transduction |
CA2230894A1 (en) | 1995-09-01 | 1997-03-13 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
US5811428A (en) | 1995-12-18 | 1998-09-22 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
DK1186606T4 (en) | 1995-11-17 | 2011-12-05 | Biotechnolog Forschung Gmbh | Epothilone derivatives, their preparation and use |
US5677097A (en) | 1996-01-18 | 1997-10-14 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor |
US6011029A (en) | 1996-02-26 | 2000-01-04 | Bristol-Myers Squibb Company | Inhibitors of farnesyl protein transferase |
CA2250231A1 (en) | 1996-04-03 | 1997-10-09 | Robert P. Gomez | Inhibitors of farnesyl-protein transferase |
ATE408612T1 (en) | 1996-11-18 | 2008-10-15 | Biotechnolog Forschung Gmbh | EPOTHILONES E AND F |
CA2273083C (en) | 1996-12-03 | 2012-09-18 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
US6380394B1 (en) | 1996-12-13 | 2002-04-30 | The Scripps Research Institute | Epothilone analogs |
US6441186B1 (en) | 1996-12-13 | 2002-08-27 | The Scripps Research Institute | Epothilone analogs |
ATE236890T1 (en) * | 1996-12-23 | 2003-04-15 | Bristol Myers Squibb Pharma Co | OXYGEN OR SULFUR CONTAINING 5-MEMBED HETEROAROMATIC DERIVATIVES AS FACTOR XA INHIBITORS |
US6187797B1 (en) * | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
NZ337195A (en) | 1997-02-25 | 2001-05-25 | Biotechnolog Forschung Gmbh | Epothilones with a modified side chain |
AU7687998A (en) | 1997-05-19 | 1998-12-11 | Sugen, Inc. | Heteroarylcarboxamide compounds active against protein tyrosine kinase related disorders |
US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
GB9801231D0 (en) | 1997-06-05 | 1998-03-18 | Merck & Co Inc | A method of treating cancer |
CA2293400A1 (en) * | 1997-06-13 | 1998-12-17 | Gerald Mcmahon | Novel heteroaryl compounds for the modulation of protein tyrosine enzyme related cellular signal transduction |
US5896223A (en) * | 1997-06-13 | 1999-04-20 | Tigliev; George S. | Optical system having an unlimited depth of focus |
ES2239806T3 (en) * | 1997-06-19 | 2005-10-01 | Bristol-Myers Squibb Pharma Company | XA FACTOR INHIBITORS WITH A P1 NEUTRAL SPECIFICITY GROUP. |
US6093742A (en) | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
WO1999002224A1 (en) | 1997-07-07 | 1999-01-21 | Lewis Robert D | Statistical analysis and feedback system for sports employing a projectile |
US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
JPH1180137A (en) | 1997-07-10 | 1999-03-26 | Nissan Chem Ind Ltd | Carbamoyltetrazole and herbicide |
WO1999003848A1 (en) | 1997-07-16 | 1999-01-28 | Schering Aktiengesellschaft | Thiazole derivatives, method for their production and use |
DK1005465T3 (en) | 1997-08-09 | 2007-11-05 | Bayer Schering Pharma Ag | New epothilone derivatives, processes for their preparation and their pharmaceutical use |
NZ503788A (en) | 1997-10-27 | 2002-11-26 | Agouron Pharma | 4-aminothiazole derivatives and their use as inhibitors of cyclin-dependent kinases |
US6022884A (en) | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
KR20010031912A (en) | 1997-11-10 | 2001-04-16 | 스티븐 비. 데이비스 | Benzothiazole Protein Tyrosine Kinase Inhibitors |
US6040321A (en) | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
EP1042327B1 (en) | 1997-12-04 | 2003-09-17 | Bristol-Myers Squibb Company | A process for the reduction of oxiranyl epothilones to olefinic epothilones |
US6365749B1 (en) | 1997-12-04 | 2002-04-02 | Bristol-Myers Squibb Company | Process for the preparation of ring-opened epothilone intermediates which are useful for the preparation of epothilone analogs |
ES2308821T3 (en) | 1997-12-15 | 2008-12-01 | Astellas Pharma Inc. | NEW DERIVATIVES OF PIRIMIDIN-5-CARBOXAMIDA. |
JPH11180965A (en) | 1997-12-24 | 1999-07-06 | Nissan Chem Ind Ltd | New carbamoyltetrazolinone and herbicide |
SI0928793T1 (en) | 1998-01-02 | 2002-10-31 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
EP0928790B1 (en) * | 1998-01-02 | 2003-03-05 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
ATE307123T1 (en) | 1998-02-25 | 2005-11-15 | Sloan Kettering Inst Cancer | SYNTHESIS OF EPOTHILONES, THEIR INTERMEDIATE PRODUCTS AND ANALOGUE COMPOUNDS |
WO1999047529A1 (en) | 1998-03-18 | 1999-09-23 | Ariad Pharmaceuticals, Inc. | Heterocyclic signal transduction inhibitors, compositions containing them |
US6498257B1 (en) | 1998-04-21 | 2002-12-24 | Bristol-Myers Squibb Company | 2,3-olefinic epothilone derivatives |
US6399638B1 (en) | 1998-04-21 | 2002-06-04 | Bristol-Myers Squibb Company | 12,13-modified epothilone derivatives |
KR100404256B1 (en) | 1998-05-05 | 2003-11-01 | 에프. 호프만-라 로슈 아게 | Pyrazole derivatives as p-38 map kinase inhibitors |
MY132496A (en) | 1998-05-11 | 2007-10-31 | Vertex Pharma | Inhibitors of p38 |
UA60365C2 (en) | 1998-06-04 | 2003-10-15 | Пфайзер Продактс Інк. | Isothiazole derivatives, a method for preparing thereof, a pharmaceutical composition and a method for treatment of hyperproliferative disease of mammal |
DE19826988A1 (en) | 1998-06-18 | 1999-12-23 | Biotechnolog Forschung Gmbh | Epothilone minor components |
WO1999067253A2 (en) | 1998-06-22 | 1999-12-29 | Novartis Ag | Desmethyl epothilones |
AU5036999A (en) | 1998-06-30 | 2000-01-17 | Schering Aktiengesellschaft | Epothilon derivatives, their preparation process, intermediate products and their pharmaceutical use |
AU747427B2 (en) | 1998-07-10 | 2002-05-16 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
GB9816533D0 (en) | 1998-07-29 | 1998-09-30 | Zeneca Ltd | Preparation of heterocyclic thiols |
WO2000017175A1 (en) | 1998-09-18 | 2000-03-30 | Vertex Pharmaceuticals Incorporated | INHIBITORS OF p38 |
JP3244672B2 (en) | 1998-10-13 | 2002-01-07 | 住友製薬株式会社 | Pharmaceuticals consisting of isoxazole derivatives |
IL142090A0 (en) * | 1998-10-22 | 2002-03-10 | Hoffmann La Roche | Thiazole derivatives |
GB9823873D0 (en) | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
GB9823871D0 (en) | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
DE69926542T2 (en) | 1998-12-25 | 2006-04-27 | Teikoku Hormone Mfg. Co., Ltd. | aminopyrazole |
NZ514095A (en) | 1999-02-10 | 2001-09-28 | Welfide Corp | Amide compounds and medicinal use thereof |
KR100342044B1 (en) | 1999-04-14 | 2002-06-27 | 김순택 | Green Emitting Phosphor Composition and Cathod-Ray Tube manufactured using the same |
JP3989175B2 (en) * | 1999-04-15 | 2007-10-10 | ブリストル−マイヤーズ スクイブ カンパニー | Cyclic protein tyrosine kinase inhibitor |
US7125875B2 (en) | 1999-04-15 | 2006-10-24 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
UA71971C2 (en) | 1999-06-04 | 2005-01-17 | Agoron Pharmaceuticals Inc | Diaminothiazoles, composition based thereon, a method for modulation of protein kinases activity, a method for the treatment of diseases mediated by protein kinases |
AU6471300A (en) | 1999-08-06 | 2001-03-05 | Takeda Chemical Industries Ltd. | P38map kinase inhibitors |
US6114365A (en) | 1999-08-12 | 2000-09-05 | Pharmacia & Upjohn S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
WO2001012621A1 (en) | 1999-08-13 | 2001-02-22 | Vertex Pharmaceuticals Incorporated | INHIBITORS OF c-JUN N-TERMINAL KINASES (JNK) AND OTHER PROTEIN KINASES |
JP3892296B2 (en) | 1999-09-10 | 2007-03-14 | メルク エンド カムパニー インコーポレーテッド | Tyrosine kinase inhibitor |
NZ520143A (en) | 2000-01-19 | 2005-01-28 | Alteon Inc | Thiazole, imidazole and oxazole compounds and treatments of disorders associated with protein aging |
WO2001056567A1 (en) * | 2000-02-04 | 2001-08-09 | Novo Nordisk A/S | 2,4-diaminothiazole derivatives and their use as glycogen synthase kinase-3 (gsk-3) inhibitors |
US20020132836A1 (en) | 2000-10-11 | 2002-09-19 | Chemocentryx Inc. | Compounds and methods for modulating CCR4 function |
US20020173524A1 (en) | 2000-10-11 | 2002-11-21 | Tularik Inc. | Modulation of CCR4 function |
US20020137755A1 (en) | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
EP1353676A4 (en) | 2000-12-29 | 2006-05-31 | Alteon Inc | Method for treating fibrotic diseases or other indications |
JP2002338537A (en) | 2001-05-16 | 2002-11-27 | Mitsubishi Pharma Corp | Amide compound and its medicinal use |
JP4917243B2 (en) | 2001-05-23 | 2012-04-18 | 日本曹達株式会社 | Method for producing thiazole compound |
US7144903B2 (en) * | 2001-05-23 | 2006-12-05 | Amgen Inc. | CCR4 antagonists |
JP4011359B2 (en) | 2002-02-15 | 2007-11-21 | 株式会社ニフコ | Cup holder device |
US20050009891A1 (en) | 2003-07-09 | 2005-01-13 | Lee Francis Y. | Combination of SRC Kinase inhibitors and chemotherapeutic agents for the treatment of proliferative diseases |
US7491725B2 (en) | 2004-02-06 | 2009-02-17 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
US7652146B2 (en) * | 2004-02-06 | 2010-01-26 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-carboxamides useful as kinase inhibitors |
TW200628156A (en) * | 2004-11-04 | 2006-08-16 | Bristol Myers Squibb Co | Combination of a SRC kinase inhibitor and a BCR-ABL inhibitor for the treatment of proliferative diseases |
US20060235006A1 (en) | 2005-04-13 | 2006-10-19 | Lee Francis Y | Combinations, methods and compositions for treating cancer |
CN102813655A (en) * | 2005-05-05 | 2012-12-12 | 布里斯托尔-迈尔斯斯奎布公司 | Formulations of a SRC/ABL inhibitor |
WO2007035874A1 (en) * | 2005-09-21 | 2007-03-29 | Bristol-Myers Squibb Company | Oral administration of n-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-1,3-thiazole-5-carboxamide and salts thereof |
JP4316559B2 (en) | 2005-11-30 | 2009-08-19 | 株式会社ナノクリエート | Light guide plate and manufacturing method thereof |
US8554512B2 (en) | 2006-06-13 | 2013-10-08 | Nike, Inc. | Athletic performance data system and method |
US7678998B2 (en) | 2007-05-21 | 2010-03-16 | Cicoil, Llc | Cable assembly |
US8897586B2 (en) | 2012-06-15 | 2014-11-25 | Comcast Cable Communications, Llc | Dynamic generation of a quantization matrix for compression of a digital object |
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