CN1826324A - 吲唑、苯并异噁唑和苯并异噻唑激酶抑制剂 - Google Patents
吲唑、苯并异噁唑和苯并异噻唑激酶抑制剂 Download PDFInfo
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- CN1826324A CN1826324A CNA2004800205684A CN200480020568A CN1826324A CN 1826324 A CN1826324 A CN 1826324A CN A2004800205684 A CNA2004800205684 A CN A2004800205684A CN 200480020568 A CN200480020568 A CN 200480020568A CN 1826324 A CN1826324 A CN 1826324A
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- Prior art keywords
- phenyl
- amino
- urea
- indazole
- fluoro
- Prior art date
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- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title description 2
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 300
- 238000000034 method Methods 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 69
- 238000011282 treatment Methods 0.000 claims abstract description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 417
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 380
- 229910052739 hydrogen Inorganic materials 0.000 claims description 302
- 239000001257 hydrogen Substances 0.000 claims description 302
- 125000003545 alkoxy group Chemical group 0.000 claims description 296
- 125000000217 alkyl group Chemical group 0.000 claims description 264
- 239000004202 carbamide Substances 0.000 claims description 228
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 180
- -1 heterocyclic radical Chemical class 0.000 claims description 149
- 150000002431 hydrogen Chemical class 0.000 claims description 120
- 229910052736 halogen Inorganic materials 0.000 claims description 117
- 150000002367 halogens Chemical class 0.000 claims description 117
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 100
- 125000001188 haloalkyl group Chemical group 0.000 claims description 76
- 125000004104 aryloxy group Chemical group 0.000 claims description 75
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 74
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 57
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 48
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 47
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 34
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 13
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 11
- RCFKEIREOSXLET-UHFFFAOYSA-N disulfamide Chemical compound CC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O RCFKEIREOSXLET-UHFFFAOYSA-N 0.000 claims description 11
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 7
- 102000001253 Protein Kinase Human genes 0.000 claims description 6
- 108060006633 protein kinase Proteins 0.000 claims description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- FHVZLYZHTFWZBU-UHFFFAOYSA-N NC1=NNC2=CC=CC(=C12)C1=CC=C(C=C1)NC(=O)NC1=C(C=CC(=C1)CN)F Chemical compound NC1=NNC2=CC=CC(=C12)C1=CC=C(C=C1)NC(=O)NC1=C(C=CC(=C1)CN)F FHVZLYZHTFWZBU-UHFFFAOYSA-N 0.000 claims description 4
- OKSJGKZXJBALIC-UHFFFAOYSA-N [O]c1cccnc1 Chemical compound [O]c1cccnc1 OKSJGKZXJBALIC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- USYMWIOIMAPLKQ-UHFFFAOYSA-N 1-[4-(3-amino-1,2-benzoxazol-4-yl)phenyl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NOC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F USYMWIOIMAPLKQ-UHFFFAOYSA-N 0.000 claims description 3
- QBINMYSOQKXQQY-UHFFFAOYSA-N 1-[4-(3-amino-1,2-benzoxazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NOC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 QBINMYSOQKXQQY-UHFFFAOYSA-N 0.000 claims description 3
- LHKISDLQDMVACN-UHFFFAOYSA-N 1-[4-(3-amino-7-fluoro-1h-indazol-4-yl)phenyl]-3-(3-bromophenyl)urea Chemical compound C=12C(N)=NNC2=C(F)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Br)=C1 LHKISDLQDMVACN-UHFFFAOYSA-N 0.000 claims description 3
- GICJPKNAEXYLLP-UHFFFAOYSA-N 1-[4-(3-amino-7-fluoro-1h-indazol-4-yl)phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=C(F)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F GICJPKNAEXYLLP-UHFFFAOYSA-N 0.000 claims description 3
- RHVSLTVUHZLKTK-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-(3-bromophenyl)urea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Br)=C1 RHVSLTVUHZLKTK-UHFFFAOYSA-N 0.000 claims description 3
- TVANTWOZIDQZPW-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-(3-ethylphenyl)urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C(O)=CC=2)=C1 TVANTWOZIDQZPW-UHFFFAOYSA-N 0.000 claims description 3
- SGBWPSGQHRKBIC-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-(3-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 SGBWPSGQHRKBIC-UHFFFAOYSA-N 0.000 claims description 3
- OQXNZBNSZVBRKJ-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 OQXNZBNSZVBRKJ-UHFFFAOYSA-N 0.000 claims description 3
- WITLPKVWXDHYIG-UHFFFAOYSA-N 1-[4-(3-amino-7-hydroxy-1h-indazol-4-yl)phenyl]-3-phenylurea Chemical compound C=12C(N)=NNC2=C(O)C=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 WITLPKVWXDHYIG-UHFFFAOYSA-N 0.000 claims description 3
- HPNXRBIPVXZNRH-UHFFFAOYSA-N 1-[4-[3-amino-7-(morpholin-4-ylmethyl)-1h-indazol-4-yl]phenyl]-3-(3-fluorophenyl)urea Chemical compound C1=CC(C=2C=CC(NC(=O)NC=3C=C(F)C=CC=3)=CC=2)=C2C(N)=NNC2=C1CN1CCOCC1 HPNXRBIPVXZNRH-UHFFFAOYSA-N 0.000 claims description 3
- DIVSMZRKCNCTAE-UHFFFAOYSA-N C1=CC(=CC(=C1)NC(=O)NC2=CC=C(C=C2)C3=C4C(=CC=C3)ON=C4N)CN Chemical compound C1=CC(=CC(=C1)NC(=O)NC2=CC=C(C=C2)C3=C4C(=CC=C3)ON=C4N)CN DIVSMZRKCNCTAE-UHFFFAOYSA-N 0.000 claims description 3
- OCFHFHNFMBNHCD-UHFFFAOYSA-N NC1=NNC2=CC(=CC(=C12)Br)C1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN Chemical compound NC1=NNC2=CC(=CC(=C12)Br)C1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN OCFHFHNFMBNHCD-UHFFFAOYSA-N 0.000 claims description 3
- KGLJHAFOHQKFIM-UHFFFAOYSA-N NC1=NNC2=CC(=CC(=C12)C1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN)Br Chemical compound NC1=NNC2=CC(=CC(=C12)C1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN)Br KGLJHAFOHQKFIM-UHFFFAOYSA-N 0.000 claims description 3
- SCOZFUZRBFNRLV-UHFFFAOYSA-N NC1=NNC2=CC=CC(=C12)C1=CC(=C(C=C1)NC(=O)NC1=C(C=CC(=C1)CN)F)CC Chemical compound NC1=NNC2=CC=CC(=C12)C1=CC(=C(C=C1)NC(=O)NC1=C(C=CC(=C1)CN)F)CC SCOZFUZRBFNRLV-UHFFFAOYSA-N 0.000 claims description 3
- KTAAKVRXJWWQJQ-UHFFFAOYSA-N NC1=NNC2=CC=CC(=C12)C1=CC(=C(C=C1)NC(=O)NC1=C(C=CC(=C1)CN)F)F Chemical compound NC1=NNC2=CC=CC(=C12)C1=CC(=C(C=C1)NC(=O)NC1=C(C=CC(=C1)CN)F)F KTAAKVRXJWWQJQ-UHFFFAOYSA-N 0.000 claims description 3
- WCHOFTOAQXAYJA-UHFFFAOYSA-N NC1=NNC2=CC=CC(=C12)C1=CC(=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN)F Chemical compound NC1=NNC2=CC=CC(=C12)C1=CC(=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN)F WCHOFTOAQXAYJA-UHFFFAOYSA-N 0.000 claims description 3
- IHHQGNMJFVCNJT-UHFFFAOYSA-N NC1=NNC2=CC=CC(=C12)C1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN Chemical compound NC1=NNC2=CC=CC(=C12)C1=CC=C(C=C1)NC(=O)NC1=CC(=CC=C1)CN IHHQGNMJFVCNJT-UHFFFAOYSA-N 0.000 claims description 3
- CYGQVCPQAICXPB-UHFFFAOYSA-N NC1=NNC2=CC=CC(=C12)C=1C=C(C=CC1)NC(=O)NC1=CC(=CC=C1)CN Chemical compound NC1=NNC2=CC=CC(=C12)C=1C=C(C=CC1)NC(=O)NC1=CC(=CC=C1)CN CYGQVCPQAICXPB-UHFFFAOYSA-N 0.000 claims description 3
- 229960001413 acetanilide Drugs 0.000 claims description 3
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 3
- LAVBIYHNXRCOKB-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)-2-ethylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound CCC1=CC(C=2C=3C(N)=NNC=3C=CC=2)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 LAVBIYHNXRCOKB-UHFFFAOYSA-N 0.000 claims description 2
- XTGFKWJKRWPKSI-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)-2-fluorophenyl]-3-(3-chloro-4-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 XTGFKWJKRWPKSI-UHFFFAOYSA-N 0.000 claims description 2
- XNLDLUQSTPVMTD-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)-2-fluorophenyl]-3-(3-ethylphenyl)urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=3C(N)=NNC=3C=CC=2)F)=C1 XNLDLUQSTPVMTD-UHFFFAOYSA-N 0.000 claims description 2
- DFSNEAFXYAHCMV-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)-2-fluorophenyl]-3-(3-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(F)=C1 DFSNEAFXYAHCMV-UHFFFAOYSA-N 0.000 claims description 2
- VVCCQOIZUNRHOM-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-(2-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F VVCCQOIZUNRHOM-UHFFFAOYSA-N 0.000 claims description 2
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- BNFKHGHCITYDOT-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-(3-ethylphenyl)urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C=CC=2)=C1 BNFKHGHCITYDOT-UHFFFAOYSA-N 0.000 claims description 2
- DMTDZFGYURLLKX-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-(3-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 DMTDZFGYURLLKX-UHFFFAOYSA-N 0.000 claims description 2
- OPTYQCYBVIBKCC-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-(3-hydroxyphenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(O)=C1 OPTYQCYBVIBKCC-UHFFFAOYSA-N 0.000 claims description 2
- YIMVQUCYRYQTLJ-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-(4-bromo-2-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(Br)C=C1F YIMVQUCYRYQTLJ-UHFFFAOYSA-N 0.000 claims description 2
- RPCMGDNNIFRGGQ-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-(4-fluorophenyl)urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C=C1 RPCMGDNNIFRGGQ-UHFFFAOYSA-N 0.000 claims description 2
- LGMSECGNRFRLTH-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-[2-fluoro-3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1F LGMSECGNRFRLTH-UHFFFAOYSA-N 0.000 claims description 2
- JBAAMDZTSDRVLV-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F JBAAMDZTSDRVLV-UHFFFAOYSA-N 0.000 claims description 2
- OSIDXFCEXZWGRW-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 OSIDXFCEXZWGRW-UHFFFAOYSA-N 0.000 claims description 2
- MXRPRVLJDJYRRD-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-[4-fluoro-3-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(C(F)(F)F)=C1 MXRPRVLJDJYRRD-UHFFFAOYSA-N 0.000 claims description 2
- UXMNYFJHEBEDJS-UHFFFAOYSA-N 1-[4-(3-amino-1h-indazol-4-yl)phenyl]-3-phenylurea Chemical compound C=12C(N)=NNC2=CC=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 UXMNYFJHEBEDJS-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
Description
Claims (52)
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US10/443254 | 2003-05-22 | ||
US10/443,254 US20040235892A1 (en) | 2003-05-22 | 2003-05-22 | Indazole and benzisoxazole kinase inhibitors |
US10/842292 | 2004-05-10 | ||
US10/842,292 US7297709B2 (en) | 2003-05-22 | 2004-05-10 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
PCT/US2004/016166 WO2004113304A1 (en) | 2003-05-22 | 2004-05-21 | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
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Families Citing this family (110)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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SG190788A1 (en) | 2010-11-15 | 2013-07-31 | Five Prime Therapeutics Inc | Fgfr1 extracellular domain combination therapies |
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CN108178789B (zh) | 2011-04-20 | 2021-11-02 | 阿塞勒隆制药公司 | 内皮糖蛋白多肽及其用途 |
WO2012158810A1 (en) | 2011-05-17 | 2012-11-22 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
CN102432595B (zh) * | 2011-09-14 | 2013-09-25 | 湖南有色凯铂生物药业有限公司 | N-吲哚-1-酰胺类化合物及作为抗癌药物的应用 |
JP6106685B2 (ja) | 2011-11-17 | 2017-04-05 | ダナ−ファーバー キャンサー インスティテュート, インコーポレイテッド | C−jun−n−末端キナーゼ(jnk)の阻害剤 |
EP2909194A1 (en) | 2012-10-18 | 2015-08-26 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
USRE48175E1 (en) | 2012-10-19 | 2020-08-25 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged small molecules as inducers of protein degradation |
US10000483B2 (en) | 2012-10-19 | 2018-06-19 | Dana-Farber Cancer Institute, Inc. | Bone marrow on X chromosome kinase (BMX) inhibitors and uses thereof |
EP3763710A1 (en) | 2013-02-20 | 2021-01-13 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
CA2906057A1 (en) | 2013-03-13 | 2014-10-02 | Genentech, Inc. | Antibody formulations |
SG11201508878WA (en) | 2013-05-01 | 2015-11-27 | Five Prime Therapeutics Inc | Methods of treating cancer |
WO2014190147A2 (en) | 2013-05-23 | 2014-11-27 | Five Prime Therapeutics, Inc. | Methods of treating cancer |
WO2014201127A2 (en) | 2013-06-11 | 2014-12-18 | Kala Pharmaceuticals, Inc. | Urea derivatives and uses thereof |
US8759538B1 (en) | 2013-06-13 | 2014-06-24 | Abbvie Inc. | Crystalline chemotherapeutic |
CN103524421B (zh) * | 2013-09-29 | 2015-04-01 | 镇江蓝德特药业科技有限公司 | 新型萘脲类衍生物及其医疗应用 |
WO2015058126A1 (en) | 2013-10-18 | 2015-04-23 | Syros Pharmaceuticals, Inc. | Heteroaromatic compounds useful for the treatment of prolferative diseases |
AU2014337044A1 (en) | 2013-10-18 | 2016-05-05 | Dana-Farber Cancer Institute, Inc. | Polycyclic inhibitors of cyclin-dependent kinase 7 (CDK7) |
EA035481B1 (ru) | 2013-10-25 | 2020-06-23 | Акселерон Фарма, Инк. | Эндоглиновые пептиды для лечения фиброзных заболеваний |
US10017477B2 (en) | 2014-04-23 | 2018-07-10 | Dana-Farber Cancer Institute, Inc. | Janus kinase inhibitors and uses thereof |
WO2015164604A1 (en) | 2014-04-23 | 2015-10-29 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged janus kinase inhibitors and uses thereof |
EP2985043A1 (en) | 2014-08-14 | 2016-02-17 | Institut d'Investigació Biomèdica de Bellvitge (IDIBELL) | Process for manufacturing a customizable medical device and device obtained by said process |
WO2016044334A1 (en) | 2014-09-15 | 2016-03-24 | Genentech, Inc. | Antibody formulations |
DK3212670T3 (da) | 2014-10-29 | 2021-03-22 | Five Prime Therapeutics Inc | Kombinationsterapi mod cancer |
US10174022B2 (en) | 2014-12-10 | 2019-01-08 | Kala Pharmaceuticals, Inc. | 1-amino-triazolo(1,5-A)pyridine-substituted urea derivative and uses thereof |
AU2015371251B2 (en) | 2014-12-23 | 2020-06-11 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (CDK7) |
US10550121B2 (en) | 2015-03-27 | 2020-02-04 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
BR112017020952A2 (pt) | 2015-04-13 | 2018-07-10 | Five Prime Therapeutics Inc | método de tratamento de câncer, composição e uso da composição |
US11155615B2 (en) | 2015-05-18 | 2021-10-26 | Eureka Therapeutics, Inc. | Anti-ROR1 antibodies |
CA2986441A1 (en) | 2015-06-12 | 2016-12-15 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
WO2017015623A2 (en) | 2015-07-23 | 2017-01-26 | Inhibrx Lp | Multivalent and multispecific gitr-binding fusion proteins |
CA2996978A1 (en) | 2015-09-09 | 2017-03-16 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
BR112018008865A8 (pt) | 2015-11-02 | 2019-02-26 | Five Prime Therapeutics Inc | polipeptídeos do domínio extracelular cd80 e seu uso no tratamento do câncer |
BR112018010410A8 (pt) | 2015-11-23 | 2019-02-26 | Five Prime Therapeutics Inc | método para tratar câncer em um sujeito, composição e métodos de aumento do número de células nk e de aumento do número de uma ou mais células positivas para pd-l1 |
AU2017232610B2 (en) * | 2016-03-16 | 2021-07-22 | Plexxikon Inc. | Compounds and methods for kinase modulation and indications therefore |
US20190263919A1 (en) | 2016-07-01 | 2019-08-29 | Five Prime Therapeutics, Inc. | Combined anti tumor therapy with a gitr agonist and cpg |
CN110709420A (zh) | 2017-03-31 | 2020-01-17 | 戊瑞治疗有限公司 | 使用抗gitr抗体的癌症组合疗法 |
KR20190139216A (ko) | 2017-04-28 | 2019-12-17 | 파이브 프라임 테라퓨틱스, 인크. | Cd80 세포외 도메인 폴리펩티드를 이용한 치료 방법 |
JP7098716B2 (ja) | 2017-08-01 | 2022-07-11 | セラヴァンス バイオファーマ アール&ディー アイピー, エルエルシー | Jakキナーゼ阻害剤としてのピラゾロおよびトリアゾロ二環式化合物 |
US11421034B2 (en) | 2017-09-13 | 2022-08-23 | Five Prime Therapeutics, Inc. | Combination anti-CSF1R and anti-PD-1 antibody combination therapy for pancreatic cancer |
CN111971304A (zh) | 2018-03-21 | 2020-11-20 | 戊瑞治疗有限公司 | 在酸性pH结合至VISTA的抗体 |
PE20211604A1 (es) | 2018-07-09 | 2021-08-23 | Five Prime Therapeutics Inc | Anticuerpos de union a ilt4 |
TW202028235A (zh) | 2018-07-11 | 2020-08-01 | 美商戊瑞治療有限公司 | 於酸性ph結合至含免疫球蛋白v域之t細胞活化抑制子(vista)之抗體 |
EP3843767A1 (en) | 2018-08-29 | 2021-07-07 | Five Prime Therapeutics, Inc. | Cd80 extracellular domain fc fusion protein dosing regimens |
CN113498352A (zh) | 2019-01-23 | 2021-10-12 | 施万生物制药研发Ip有限责任公司 | 作为jak抑制剂的咪唑并[1,5-a]吡啶、1,2,4-三唑并[4,3-a]吡啶和咪唑并[1,5-a]吡嗪 |
US20220031806A1 (en) | 2019-02-22 | 2022-02-03 | Five Prime Therapeutics, Inc. | Cd80 extracellular domain fc fusion proteins for treating pd-l1 negative tumors |
KR20220065816A (ko) | 2019-09-19 | 2022-05-20 | 브리스톨-마이어스 스큅 컴퍼니 | 산성 pH에서 VISTA에 결합하는 항체 |
US20230382972A9 (en) | 2019-11-04 | 2023-11-30 | Five Prime Therapeutics, Inc. | Cd80 extracellular domain fc fusion protein regimens |
KR20230020379A (ko) | 2020-01-06 | 2023-02-10 | 하이파이바이오 (에이치케이) 리미티드 | 항-tnfr2 항체 및 이의 용도 |
WO2021139682A1 (en) | 2020-01-07 | 2021-07-15 | Hifibio (Hk) Limited | Anti-galectin-9 antibody and uses thereof |
US20240228578A1 (en) | 2020-02-26 | 2024-07-11 | Five Prime Therapeutics, Inc. | Cd80 extracellular domain fc fusion protein therapy |
EP4192866A2 (en) | 2020-08-10 | 2023-06-14 | GV20 Therapeutics LLC | Compositions and methods for treating autoimmune diseases and cancers by targeting igsf8 |
AU2021360782A1 (en) | 2020-10-14 | 2023-06-08 | Five Prime Therapeutics, Inc. | Anti-c-c chemokine receptor 8 (ccr8) antibodies and methods of use thereof |
TW202325312A (zh) | 2021-07-23 | 2023-07-01 | 美商艾拉倫製藥股份有限公司 | β-鏈蛋白(CTNNB1)iRNA組成物及其使用方法 |
WO2023081923A1 (en) | 2021-11-08 | 2023-05-11 | Frequency Therapeutics, Inc. | Platelet-derived growth factor receptor (pdgfr) alpha inhibitors and uses thereof |
WO2024015993A1 (en) | 2022-07-15 | 2024-01-18 | Fibrogen, Inc. | Modified anti-galectin-9 antibody and uses thereof |
WO2024020579A1 (en) | 2022-07-22 | 2024-01-25 | Bristol-Myers Squibb Company | Antibodies binding to human pad4 and uses thereof |
WO2024040216A2 (en) | 2022-08-19 | 2024-02-22 | Fibrogen, Inc. | Anti-ccr8 antibodies and uses thereof |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2971842A (en) * | 1956-03-21 | 1961-02-14 | Gen Aniline & Film Corp | Light sensitive layers for photomechanical reproduction |
GB816283A (en) * | 1957-06-28 | 1959-07-08 | Corson G & W H | Road building |
GB9707800D0 (en) | 1996-05-06 | 1997-06-04 | Zeneca Ltd | Chemical compounds |
WO2000027627A1 (en) * | 1998-11-12 | 2000-05-18 | Eli Lilly And Company | Aryloxime linkers in the solid-phase synthesis of 3-aminobenzisoxazoles |
JP2004518669A (ja) * | 2000-12-20 | 2004-06-24 | スージェン・インコーポレーテッド | 4−アリール置換インドリノン |
AU2002353186A1 (en) * | 2001-12-19 | 2003-06-30 | Smithkline Beecham P.L.C. | (1-h-indazol-3-yl) -amide derivatives as gsk-3 inhibitors |
AU2003221184A1 (en) * | 2002-03-29 | 2003-10-27 | Mochida Pharmaceutical Co., Ltd. | Therapeutic agent for endothelial disorder |
EP1506176B1 (en) * | 2002-05-17 | 2013-04-24 | Pfizer Italia S.r.l. | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
GB0217757D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
KR101166745B1 (ko) * | 2002-09-05 | 2012-07-23 | 아방티 파르마 소시에테 아노님 | 의약으로서의 신규한 아미노인다졸 유도체 및 이를 함유하는 약제학적 조성물 |
BR0316606A (pt) * | 2002-12-12 | 2005-10-11 | Aventis Pharma Sa | Derivados de aminoindazóis e sua utilização como inibidores de quinases |
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