JP2008516973A - キナーゼ阻害剤 - Google Patents
キナーゼ阻害剤 Download PDFInfo
- Publication number
- JP2008516973A JP2008516973A JP2007536949A JP2007536949A JP2008516973A JP 2008516973 A JP2008516973 A JP 2008516973A JP 2007536949 A JP2007536949 A JP 2007536949A JP 2007536949 A JP2007536949 A JP 2007536949A JP 2008516973 A JP2008516973 A JP 2008516973A
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- JP
- Japan
- Prior art keywords
- alkyl
- hetero
- cycloalkyl
- pyrazol
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229940043355 kinase inhibitor Drugs 0.000 title description 7
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 150
- 238000000034 method Methods 0.000 claims abstract description 48
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 42
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- -1 nitro, thio, hydroxy Chemical group 0.000 claims description 999
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 201000010099 disease Diseases 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 24
- 102000001253 Protein Kinase Human genes 0.000 claims description 18
- 108060006633 protein kinase Proteins 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 13
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 238000001727 in vivo Methods 0.000 claims description 9
- 230000007170 pathology Effects 0.000 claims description 9
- 208000024891 symptom Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 7
- 239000005022 packaging material Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- 102000003989 Aurora kinases Human genes 0.000 claims description 3
- 108090000433 Aurora kinases Proteins 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 238000001361 intraarterial administration Methods 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000007912 intraperitoneal administration Methods 0.000 claims description 2
- 238000007913 intrathecal administration Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 239000002502 liposome Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1265
- 125000005842 heteroatom Chemical group 0.000 claims 648
- 125000000753 cycloalkyl group Chemical group 0.000 claims 444
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 418
- 150000001602 bicycloalkyls Chemical group 0.000 claims 413
- 125000001072 heteroaryl group Chemical group 0.000 claims 389
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 354
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 307
- 229910052739 hydrogen Inorganic materials 0.000 claims 217
- 125000003118 aryl group Chemical group 0.000 claims 216
- 239000001257 hydrogen Substances 0.000 claims 216
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 214
- 125000003545 alkoxy group Chemical group 0.000 claims 213
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 181
- 125000004104 aryloxy group Chemical group 0.000 claims 178
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 177
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 177
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 177
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 176
- 125000005843 halogen group Chemical group 0.000 claims 164
- 125000003282 alkyl amino group Chemical group 0.000 claims 133
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 108
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 97
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 87
- 229940124530 sulfonamide Drugs 0.000 claims 84
- 150000003456 sulfonamides Chemical class 0.000 claims 83
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 66
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 35
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 35
- 125000002947 alkylene group Chemical group 0.000 claims 32
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 29
- BOUIZPWBFIVJPD-UHFFFAOYSA-N 3h-1,2,4-triazin-4-amine Chemical class NN1CN=NC=C1 BOUIZPWBFIVJPD-UHFFFAOYSA-N 0.000 claims 16
- 125000004429 atom Chemical group 0.000 claims 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 10
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 241001024304 Mino Species 0.000 claims 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 8
- 206010012289 Dementia Diseases 0.000 claims 7
- 150000001412 amines Chemical class 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 7
- 150000001408 amides Chemical class 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims 5
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims 4
- 241000894007 species Species 0.000 claims 4
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 2
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 2
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- QVESPAZTKUYKFE-UHFFFAOYSA-N 7-(3-ethylsulfonylphenyl)-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CCS(=O)(=O)C1=CC=CC(C=2N=C(NC=3NN=C(C)C=3)N3C=CN=C3C=2)=C1 QVESPAZTKUYKFE-UHFFFAOYSA-N 0.000 claims 2
- MTEVLMIUCCLOJF-UHFFFAOYSA-N 7-[3-(ethylsulfonylmethyl)phenyl]-2-methyl-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CCS(=O)(=O)CC1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 MTEVLMIUCCLOJF-UHFFFAOYSA-N 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 2
- 230000006999 cognitive decline Effects 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical class 0.000 claims 2
- MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical class 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 2
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 2
- ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- HMKSATPFCVLZAD-KRWDZBQOSA-N (2s)-n-[4-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]sulfanylphenyl]oxolane-2-carboxamide Chemical compound N=1C(SC=2C=CC(NC(=O)[C@H]3OCCC3)=CC=2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 HMKSATPFCVLZAD-KRWDZBQOSA-N 0.000 claims 1
- CMDUDMQXEVARHF-KRWDZBQOSA-N (2s)-n-[[3-[5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]methyl]pyrrolidine-2-carboxamide Chemical compound N1C(C)=CC(NC=2N3C=CN=C3C=C(N=2)C=2C=C(CNC(=O)[C@H]3NCCC3)C=CC=2)=N1 CMDUDMQXEVARHF-KRWDZBQOSA-N 0.000 claims 1
- FYLXOUQHGOJJRI-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[3-[5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]methanone Chemical compound N1C(C)=CC(NC=2N3C=CN=C3C=C(N=2)C=2C=C(C=CC=2)C(=O)N2CCC(O)CC2)=N1 FYLXOUQHGOJJRI-UHFFFAOYSA-N 0.000 claims 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 1
- OTBFUMSMIVYLAK-UHFFFAOYSA-N 1,3-thiazole-5-sulfonamide Chemical compound NS(=O)(=O)C1=CN=CS1 OTBFUMSMIVYLAK-UHFFFAOYSA-N 0.000 claims 1
- AFCXECFLGWINNG-UHFFFAOYSA-N 1-[[3-[5-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]phenyl]methyl]imidazolidin-2-one Chemical compound O=C1NCCN1CC1=CC=CC(C=2N=C(NC3=NNC(=C3)C3CC3)N3C=CN=C3C=2)=C1 AFCXECFLGWINNG-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- ZZPZQIMGCDVBIX-UHFFFAOYSA-N 2-[4-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]pyrazol-1-yl]-n-phenylacetamide Chemical compound N=1C(C2=CN(CC(=O)NC=3C=CC=CC=3)N=C2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 ZZPZQIMGCDVBIX-UHFFFAOYSA-N 0.000 claims 1
- DYADDGIMLGZAON-UHFFFAOYSA-N 2-[[4-[2-methyl-5-[(5-methyl-1h-pyrazol-3-yl)amino]imidazo[1,2-c]pyrimidin-7-yl]pyrazol-1-yl]methyl]benzonitrile Chemical compound N=1C(C2=CN(CC=3C(=CC=CC=3)C#N)N=C2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 DYADDGIMLGZAON-UHFFFAOYSA-N 0.000 claims 1
- BJQRCMRGLKTFCX-UHFFFAOYSA-N 2-[[4-[5-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]-2-methylimidazo[1,2-c]pyrimidin-7-yl]pyrazol-1-yl]methyl]benzonitrile Chemical compound N=1C(C2=CN(CC=3C(=CC=CC=3)C#N)N=C2)=CC2=NC(C)=CN2C=1NC(=NN1)C=C1C1CC1 BJQRCMRGLKTFCX-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- FMMUQXDMPOTDLB-UHFFFAOYSA-N 2-methyl-7-[1-(2-methylpropyl)pyrazol-4-yl]-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical class C1=NN(CC(C)C)C=C1C1=CC2=NC(C)=CN2C(NC2=NNC(C)=C2)=N1 FMMUQXDMPOTDLB-UHFFFAOYSA-N 0.000 claims 1
- NWUUBYBANOEWNL-UHFFFAOYSA-N 2-methyl-7-[3-(3-methylimidazol-4-yl)phenyl]-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)C=2N(C=NC=2)C)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 NWUUBYBANOEWNL-UHFFFAOYSA-N 0.000 claims 1
- NMSNGWOXZGUXPU-UHFFFAOYSA-N 2-methyl-7-[3-[3-(methylamino)pyrrolidin-1-yl]sulfonylphenyl]-n-(5-methyl-1h-pyrazol-3-yl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1C(NC)CCN1S(=O)(=O)C1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 NMSNGWOXZGUXPU-UHFFFAOYSA-N 0.000 claims 1
- QHCODFQJYAZFBH-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-piperazin-1-ylsulfonylphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)S(=O)(=O)N2CCNCC2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 QHCODFQJYAZFBH-UHFFFAOYSA-N 0.000 claims 1
- HUPVQHYRVNCWRU-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-propan-2-yloxyphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CC(C)OC1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 HUPVQHYRVNCWRU-UHFFFAOYSA-N 0.000 claims 1
- RWXSVGBXJSUDBT-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-propoxyphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound CCCOC1=CC=CC(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)=C1 RWXSVGBXJSUDBT-UHFFFAOYSA-N 0.000 claims 1
- OAZQHPZMYBNBIE-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-(3-pyrrolidin-1-ylsulfonylphenyl)imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C=2C=C(C=CC=2)S(=O)(=O)N2CCCC2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 OAZQHPZMYBNBIE-UHFFFAOYSA-N 0.000 claims 1
- QMETZUFLUYJPNN-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[1-(1-phenylpropan-2-yl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound C1=C(C=2N=C(NC3=NNC(C)=C3)N3C=C(C)N=C3C=2)C=NN1C(C)CC1=CC=CC=C1 QMETZUFLUYJPNN-UHFFFAOYSA-N 0.000 claims 1
- WJXWUUGUOWMEAY-UHFFFAOYSA-N 2-methyl-n-(5-methyl-1h-pyrazol-3-yl)-7-[1-(2-piperidin-1-ylethyl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-amine Chemical compound N=1C(C2=CN(CCN3CCCCC3)N=C2)=CC2=NC(C)=CN2C=1NC=1C=C(C)NN=1 WJXWUUGUOWMEAY-UHFFFAOYSA-N 0.000 claims 1
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008545660A (ja) * | 2005-05-20 | 2008-12-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼ阻害剤として有用なピロロピリジン化合物 |
| JP2012505234A (ja) * | 2008-10-08 | 2012-03-01 | ブリストル−マイヤーズ スクイブ カンパニー | ピロロトリアジンキナーゼ阻害剤 |
| JP2012517965A (ja) * | 2009-02-13 | 2012-08-09 | バイエル ファーマ アクチエンゲゼルシャフト | Ａｋｔインヒビターとしての融合されたピリミジン |
| JP2013523884A (ja) * | 2010-04-14 | 2013-06-17 | アレイ バイオファーマ、インコーポレイテッド | ＪＡＫキナーゼの阻害剤としての５，７置換イミダゾ［１，２−ｃ］ピリミジン |
| JP2015518010A (ja) * | 2012-05-31 | 2015-06-25 | 上海 インスティテュート オブ マテリア メディカ、チャイニーズ アカデミー オブ サイエンシーズＳｈａｎｇｈａｉ Ｉｎｓｔｉｔｕｔｅ Ｏｆ Ｍａｔｅｒｉａ Ｍｅｄｉｃａ， Ｃｈｉｎｅｓｅ Ａｃａｄｅｍｙ Ｏｆ Ｓｃｉｅｎｃｅｓ | ピロロ［２，１−ｆ］［１，２，４］トリアジン系化合物、その製造方法および用途 |
| JP2017511365A (ja) * | 2014-04-17 | 2017-04-20 | アッヴィ・インコーポレイテッド | 複素環キナーゼ阻害薬 |
Families Citing this family (110)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1572514A4 (en) * | 2002-10-16 | 2007-09-26 | Transp Systems Inc | DISTRIBUTION SYSTEM FOR ONE RAILWAY |
| US7459562B2 (en) | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| EP1812439B2 (en) * | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| MX2007005857A (es) | 2004-11-17 | 2007-10-10 | Mikana Therapeutics Inc | Inhibidores de cinasa. |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| US7579360B2 (en) | 2005-06-09 | 2009-08-25 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| US7232901B2 (en) * | 2005-07-01 | 2007-06-19 | Bristol-Myers Squibb Company | Intermediates useful in preparing certain pyrrolotriazine compounds and process for making such intermediates |
| US7442700B2 (en) * | 2005-07-01 | 2008-10-28 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds useful as kinase inhibitors and methods of treating kinase-associated conditions therewith |
| EP1906948A4 (en) * | 2005-07-18 | 2010-03-17 | Bipar Sciences Inc | TREATMENT OF CANCER |
| BRPI0616630B8 (pt) * | 2005-09-30 | 2021-05-25 | Miikana Therapeutics Inc | compostos de pirazol substituídos |
| JP5182088B2 (ja) * | 2006-04-19 | 2013-04-10 | アステラス製薬株式会社 | アゾールカルボキサミド誘導体 |
| US7893058B2 (en) * | 2006-05-15 | 2011-02-22 | Janssen Pharmaceutica Nv | Imidazolopyrazine compounds useful for the treatment of degenerative and inflammatory diseases |
| US20100279327A1 (en) * | 2006-06-12 | 2010-11-04 | Bipar Sciences, Inc. | Method of treating diseases with parp inhibitors |
| SI2041138T1 (sl) * | 2006-07-07 | 2014-08-29 | Bristol-Myers Squibb Company | Pirolotriazin kinazni inhibitorji |
| US7531539B2 (en) * | 2006-08-09 | 2009-05-12 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| EP2049542B1 (en) * | 2006-08-09 | 2012-09-19 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| AU2007292306A1 (en) | 2006-09-05 | 2008-03-13 | Bipar Sciences, Inc. | Inhibition of fatty acid synthesis by PARP inhibitors and methods of treatment thereof |
| WO2008030883A2 (en) * | 2006-09-05 | 2008-03-13 | Bipar Sciences, Inc. | Treatment of cancer |
| PE20080931A1 (es) * | 2006-11-08 | 2008-07-19 | Schering Corp | Imidazopirazinas como inhibidores de proteina quinasa |
| WO2008083398A2 (en) * | 2007-01-02 | 2008-07-10 | Bristol-Myers Squibb Company | Intermediate useful in preparing certain pyrrolotriazine compounds and a process for making the intermediate |
| WO2008086264A1 (en) * | 2007-01-08 | 2008-07-17 | Bristol-Myers Squibb Company | Intermediates useful in preparing certain pyrrolotriazine compounds and a process for making the intermediates |
| DE102007012645A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| WO2008116064A2 (en) | 2007-03-21 | 2008-09-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful for the treatment of proliferative, allergic, autoimmune or inflammatory diseases |
| WO2008131050A1 (en) * | 2007-04-18 | 2008-10-30 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| JP2010529193A (ja) * | 2007-06-11 | 2010-08-26 | ミイカナ セラピューティクス インコーポレイテッド | 置換ピラゾール化合物 |
| DE102007032349A1 (de) | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| SI2206707T1 (sl) * | 2007-10-24 | 2014-11-28 | Astellas Pharma Inc. | Azolkarboksamidna spojina ali njena sol |
| US7868001B2 (en) * | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| WO2009064738A2 (en) * | 2007-11-12 | 2009-05-22 | Bipar Sciences, Inc. | Treatment of breast cancer with a parp inhibitor alone or in combination with anti-tumor agents |
| AU2008333786A1 (en) * | 2007-12-07 | 2009-06-11 | Bipar Sciences, Inc. | Treatment of cancer with combinations of topoisomerase inhibitors and PARP inhibitors |
| DE102008035209A1 (de) | 2008-07-29 | 2010-02-04 | Bayer Schering Pharma Aktiengesellschaft | Triazolotriazine und Triazolopyrazine und ihre Verwendung |
| DE102007060172A1 (de) | 2007-12-13 | 2009-06-25 | Bayer Healthcare Ag | Triazolotriazine und Triazolopyrazine und ihre Verwendung |
| PE20091074A1 (es) * | 2007-12-13 | 2009-07-26 | Bayer Healthcare Ag | Triazolotriazinas y triazolopirazinas y su uso |
| EP2240466B1 (en) * | 2008-01-08 | 2015-07-29 | Merck Sharp & Dohme Limited | Pharmaceutically acceptable salts of 2-{4-[(3s)-piperidin-3- yl]phenyl} -2h-indazole-7-carboxamide |
| CA2710929A1 (en) * | 2008-01-28 | 2009-08-06 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| JP5496915B2 (ja) | 2008-02-13 | 2014-05-21 | シージーアイ ファーマシューティカルズ，インコーポレーテッド | ６−アリール−イミダゾ［１，２−ａ］ピラジン誘導体、その製造方法、及びその使用方法 |
| DE102008023801A1 (de) | 2008-05-15 | 2009-11-19 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Imidazo- und Triazolopyrimidine, Imidazo- und Pyrazolopyrazine und Imidazotriazine |
| WO2010011837A1 (en) | 2008-07-24 | 2010-01-28 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US8450321B2 (en) | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| PE20120121A1 (es) | 2008-12-08 | 2012-02-20 | Gilead Connecticut Inc | Derivados de imidazopirazina como inhibidores de syk |
| EA020461B1 (ru) * | 2008-12-08 | 2014-11-28 | Джилид Коннектикут, Инк. | ИМИДАЗОПИРАЗИНОВЫЕ ИНГИБИТОРЫ Syk |
| WO2010071885A1 (en) | 2008-12-19 | 2010-06-24 | Cephalon, Inc. | Pyrrolotriazines as alk and jak2 inhibitors |
| ES2443948T3 (es) | 2008-12-19 | 2014-02-21 | Bristol-Myers Squibb Company | Compuestos de carbazol carboxamida útiles como inhibidores de quinasas |
| CN102458402B (zh) | 2009-06-12 | 2013-10-02 | 百时美施贵宝公司 | 用作激酶调节剂的烟酰胺化合物 |
| WO2011019780A1 (en) | 2009-08-11 | 2011-02-17 | Bristol-Myers Squibb Company | Azaindazoles as btk kinase modulators and use thereof |
| WO2011088045A1 (en) | 2010-01-12 | 2011-07-21 | Ambit Biosciences Corporation | Aurora kinase compounds and methods of their use |
| CA2787714C (en) | 2010-01-22 | 2019-04-09 | Joaquin Pastor Fernandez | Inhibitors of pi3 kinase |
| JP5093527B2 (ja) * | 2010-02-10 | 2012-12-12 | 日本電気株式会社 | 複合光導波路、波長可変フィルタ、波長可変レーザ、および光集積回路 |
| JP5938352B2 (ja) | 2010-03-11 | 2016-06-22 | ギリアード コネチカット， インコーポレイテッド | イミダゾピリジンｓｙｋ阻害剤 |
| US20130131057A1 (en) | 2010-05-13 | 2013-05-23 | Centro Nacional De Investigaciones Oncologicas (Cnio | New bicyclic compounds as pi3-k and mtor inhibitors |
| US8685969B2 (en) | 2010-06-16 | 2014-04-01 | Bristol-Myers Squibb Company | Carboline carboxamide compounds useful as kinase inhibitors |
| JP5543039B2 (ja) | 2011-02-23 | 2014-07-09 | ファイザー・インク | 神経障害治療のためのイミダゾ［５，１−ｆ］［１，２，４］トリアジン |
| UY34329A (es) | 2011-09-15 | 2013-04-30 | Novartis Ag | Compuestos de triazolopiridina |
| US9724352B2 (en) | 2012-05-31 | 2017-08-08 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Pyrrolo[2,1-F[1,2,4]triazine compounds, preparation methods and applications thereof |
| US9050345B2 (en) | 2013-03-11 | 2015-06-09 | Bristol-Myers Squibb Company | Pyrrolotriazines as potassium ion channel inhibitors |
| KR102345381B1 (ko) | 2013-06-25 | 2021-12-29 | 브리스톨-마이어스 스큅 컴퍼니 | 키나제 억제제로서 유용한 카르바졸 카르복스아미드 화합물 |
| AR096721A1 (es) | 2013-06-25 | 2016-01-27 | Bristol Myers Squibb Co | Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos |
| PL3027171T3 (pl) | 2013-07-30 | 2020-08-24 | Gilead Connecticut, Inc. | Formulacja inhibitorów syk |
| EA029281B1 (ru) | 2013-07-30 | 2018-03-30 | Джилид Коннектикут, Инк. | Полиморф ингибиторов syk |
| AU2014360537B2 (en) | 2013-12-04 | 2017-09-07 | Gilead Sciences, Inc. | Methods for treating cancers |
| TWI662037B (zh) | 2013-12-23 | 2019-06-11 | 美商基利科學股份有限公司 | 脾酪胺酸激酶抑制劑 |
| US9290505B2 (en) | 2013-12-23 | 2016-03-22 | Gilead Sciences, Inc. | Substituted imidazo[1,2-a]pyrazines as Syk inhibitors |
| EP3137454A1 (en) | 2014-04-28 | 2017-03-08 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
| CN106687139A (zh) | 2014-07-14 | 2017-05-17 | 吉利德科学公司 | 用于治疗癌症的组合 |
| TWI676618B (zh) | 2014-10-24 | 2019-11-11 | 美商必治妥美雅史谷比公司 | 三環化合物 |
| MX393057B (es) | 2014-10-24 | 2025-03-24 | Bristol Myers Squibb Co | Compuestos de indol carboxamida útiles como inhibidores de cinasas. |
| CN107108555B (zh) | 2014-10-24 | 2020-12-01 | 百时美施贵宝公司 | 三环阻转异构体化合物 |
| US20170107216A1 (en) | 2015-10-19 | 2017-04-20 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CA3001768C (en) * | 2015-11-02 | 2022-12-13 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidin-7-yl compound |
| MD3377488T2 (ro) | 2015-11-19 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca imunomodulatori |
| ES2916874T3 (es) | 2015-12-17 | 2022-07-06 | Incyte Corp | Derivados de N-fenil-piridina-2-carboxamida y su uso como moduladores de la interacción proteína/proteína PD-1/PD-L1 |
| CA3009474A1 (en) | 2015-12-22 | 2017-06-29 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CN115057861A (zh) * | 2016-03-01 | 2022-09-16 | 上海医药集团股份有限公司 | 一种含氮杂环化合物、制备方法、中间体、组合物和应用 |
| ES2906460T3 (es) | 2016-05-06 | 2022-04-18 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3464279B1 (en) | 2016-05-26 | 2021-11-24 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA45669A (fr) | 2016-07-14 | 2019-05-22 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| US20180057486A1 (en) | 2016-08-29 | 2018-03-01 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| KR20190070972A (ko) | 2016-11-02 | 2019-06-21 | 얀센 파마슈티카 엔.브이. | Pde2 억제제로서의 [1,2,4]트리아졸로[1,5-a]피리미딘 유도체 |
| WO2018083101A1 (en) | 2016-11-02 | 2018-05-11 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine compounds as pde2 inhibitors |
| WO2018083103A1 (en) | 2016-11-02 | 2018-05-11 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine compounds as pde2 inhibitors |
| US10308644B2 (en) | 2016-12-22 | 2019-06-04 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| JP7311228B2 (ja) * | 2017-06-30 | 2023-07-19 | ベイジン タイド ファーマシューティカル カンパニー リミテッド | Ｒｈｏ－関連プロテインキナーゼ阻害剤、それを含む医薬組成物並びにその調製方法及び使用 |
| KR20220070056A (ko) | 2017-08-25 | 2022-05-27 | 길리애드 사이언시즈, 인코포레이티드 | Syk 억제제의 다형체 |
| AU2019227607C1 (en) | 2018-02-27 | 2023-07-20 | Incyte Corporation | Imidazopyrimidines and triazolopyrimidines as A2A / A2B inhibitors |
| SMT202300065T1 (it) | 2018-03-30 | 2023-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| CN112752756B (zh) | 2018-05-11 | 2024-06-25 | 因赛特公司 | 作为PD-L1免疫调节剂的四氢-咪唑并[4,5-c]吡啶衍生物 |
| EP3810610A1 (en) | 2018-05-18 | 2021-04-28 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| CN117304191A (zh) | 2018-07-05 | 2023-12-29 | 因赛特公司 | 作为a2a/a2b抑制剂的稠合吡嗪衍生物 |
| US12297184B2 (en) | 2018-10-03 | 2025-05-13 | Tesaro, Inc. | Niraparib salts |
| CN111018860B (zh) * | 2018-10-10 | 2022-06-10 | 中国药科大学 | 吡咯并三嗪类化合物及其应用 |
| EP4371987B9 (en) | 2018-10-31 | 2025-11-26 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds as hpk1 inhibitors |
| EP3873608A1 (en) | 2018-10-31 | 2021-09-08 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds having hpk1 inhibitory activity |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| AU2020225455A1 (en) | 2019-02-22 | 2021-09-09 | Kronos Bio, Inc. | Solid forms of condensed pyrazines as Syk inhibitors |
| CN111961034A (zh) * | 2019-05-20 | 2020-11-20 | 浙江同源康医药股份有限公司 | 用作ret激酶抑制剂的化合物及其应用 |
| US11453681B2 (en) | 2019-05-23 | 2022-09-27 | Gilead Sciences, Inc. | Substituted eneoxindoles and uses thereof |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| JP7559059B2 (ja) | 2019-09-30 | 2024-10-01 | インサイト・コーポレイション | 免疫調節剤としてのピリド［３，２－ｄ］ピリミジン化合物 |
| EP4058461A1 (en) | 2019-11-11 | 2022-09-21 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| JP7535600B2 (ja) * | 2020-06-01 | 2024-08-16 | ナンジン ルイジエ ファーマ シーオー．，エルティーディー． | 化合物および脾臓チロシンキナーゼ阻害剤としてのその使用 |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| IL302590A (en) | 2020-11-06 | 2023-07-01 | Incyte Corp | Process for preparing PD-1/PD-L1 inhibitor and salts and crystalline forms thereof |
| US11760756B2 (en) | 2020-11-06 | 2023-09-19 | Incyte Corporation | Crystalline form of a PD-1/PD-L1 inhibitor |
| EP4504341A1 (en) | 2022-04-08 | 2025-02-12 | Shy Therapeutics LLC | Compounds that interact with ras superfamily proteins for treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| TW202614926A (zh) * | 2024-09-20 | 2026-04-16 | 美商富曼西公司 | 作為殺有害生物劑的連接的雙環化合物 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000071129A1 (en) * | 1999-05-21 | 2000-11-30 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| WO2003000693A1 (de) * | 2001-06-22 | 2003-01-03 | Bayer Healthcare Ag | Imidazotriazine als phosphodiesterase inhibitoren |
| WO2004005291A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Heterocyclisch substituierte imidazotriazine |
| WO2004005290A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Substituierte imidazotriazine |
| US20040063715A1 (en) * | 2002-09-23 | 2004-04-01 | Schering Corporation | Novel imidazopyrazines as cyclin dependent kinase inhibitors |
| WO2004043912A2 (en) * | 2002-11-06 | 2004-05-27 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| WO2004087707A1 (en) * | 2003-03-31 | 2004-10-14 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
| WO2004087056A2 (en) * | 2003-03-28 | 2004-10-14 | Scios Inc. | BI-CYCLIC PYRIMIDINE INHIBITORS OF TGFβ |
Family Cites Families (185)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB828847A (en) | 1956-12-14 | 1960-02-24 | Ilford Ltd | Improvements in or relating to cyanine dyes |
| FR1242962A (fr) | 1959-08-25 | 1960-10-07 | Kodak Pathe | Nouveau procédé pour la préparation de colorants sensibilisateurs de la série des cyanines et des mérocyanines et produits obtenus |
| DE2844606A1 (de) | 1978-10-13 | 1980-04-24 | Bayer Ag | Heterocyclische farbstoffe |
| GB2013703B (en) | 1978-01-25 | 1982-06-03 | Bayer Ag | Heterocyclic dyestuffs |
| GB9222253D0 (en) | 1992-10-23 | 1992-12-09 | Celltech Ltd | Chemical compounds |
| GB9304920D0 (en) | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| US7119174B2 (en) | 1995-12-18 | 2006-10-10 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
| JP3944241B2 (ja) | 1995-12-18 | 2007-07-11 | スージェン・インコーポレーテッド | Ａｕｒ―１および／またはａｕｒ―２関連疾患の診断および処置 |
| US6716575B2 (en) | 1995-12-18 | 2004-04-06 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
| GB9707800D0 (en) | 1996-05-06 | 1997-06-04 | Zeneca Ltd | Chemical compounds |
| GB9622363D0 (en) | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9625184D0 (en) | 1996-12-04 | 1997-01-22 | Celltech Therapeutics Ltd | Chemical compounds |
| AU5330698A (en) | 1996-12-23 | 1998-07-17 | Celltech Therapeutics Limited | Fused polycyclic 2-aminopyrimidine derivatives, their preparation and their use as protein tyrosine kinase inhibitors |
| GB9705361D0 (en) | 1997-03-14 | 1997-04-30 | Celltech Therapeutics Ltd | Chemical compounds |
| ATE342971T1 (de) | 1997-08-15 | 2006-11-15 | Univ Hiroshima | Den zellzyklus regulierende proteine |
| DE69838172T2 (de) | 1997-08-22 | 2008-04-10 | Astrazeneca Ab | Oxindolylchinazolinderivate als angiogenesehemmer |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| US6143480A (en) | 1998-09-03 | 2000-11-07 | Fuji Photo Film Co., Ltd. | Leuco dye and image recording medium containing the same |
| US6706491B1 (en) | 1999-04-09 | 2004-03-16 | The Board Of Trustees Of The University Of Illinois | Reagents and methods for identifying and modulating expression of genes regulated by p21 |
| US20050113460A1 (en) | 1999-04-30 | 2005-05-26 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| US6982265B1 (en) * | 1999-05-21 | 2006-01-03 | Bristol Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| EP1203013A4 (en) | 1999-07-21 | 2004-10-13 | Univ Massachusetts | KINASE BLOCKING POLYPEPTIDES AND USES THEREOF |
| US6787545B1 (en) * | 1999-08-23 | 2004-09-07 | Shiongi & Co., Ltd. | Pyrrolotriazine derivatives having spla2-inhibitory activities |
| HK1046688A1 (zh) | 1999-09-21 | 2003-01-24 | Astrazeneca Ab | 喹唑啉化合物和含有喹唑啉化合物的藥物組合物 |
| GB9922171D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| GB9922173D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| EE200200119A (et) | 1999-09-21 | 2003-04-15 | Astrazeneca Ab | Kinasoliini derivaadid ja nende kasutamine ravimitena |
| US6455525B1 (en) | 1999-11-04 | 2002-09-24 | Cephalon, Inc. | Heterocyclic substituted pyrazolones |
| HUP0203895A3 (en) | 1999-12-24 | 2004-09-28 | Aventis Pharma Ltd West Mallin | Substituted azaindoles and pharmaceutical compositions containing them and their use |
| EP1294709A2 (en) | 2000-01-28 | 2003-03-26 | AstraZeneca AB | Quinoline derivatives and their use as aurora 2 kinase inhibitors |
| JP4739632B2 (ja) | 2000-02-05 | 2011-08-03 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｅｒｋのインヒビターとして有用なピラゾール組成物 |
| JP4783532B2 (ja) | 2000-02-05 | 2011-09-28 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｅｒｋのインヒビターとして有用なピラゾール組成物 |
| EP1209158A1 (en) | 2000-11-18 | 2002-05-29 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines |
| EP1134221A1 (en) | 2000-03-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines as lkB kinase inhibitors |
| JP2001294772A (ja) | 2000-04-10 | 2001-10-23 | Fuji Photo Film Co Ltd | 着色組成物、インクジェット用インク及びインクジェット記録方法 |
| JP2001302667A (ja) * | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| US6335342B1 (en) | 2000-06-19 | 2002-01-01 | Pharmacia & Upjohn S.P.A. | Azaindole derivatives, process for their preparation, and their use as antitumor agents |
| BR0111754A (pt) | 2000-06-28 | 2003-04-29 | Astrazeneca Ab | Uso de um composto, método para inibir aurora 2 quinase em um animal de sangue quente, composto, e, composição farmacêutica |
| US20050009876A1 (en) | 2000-07-31 | 2005-01-13 | Bhagwat Shripad S. | Indazole compounds, compositions thereof and methods of treatment therewith |
| CA2416527C (en) | 2000-08-10 | 2009-12-22 | Pharmacia Italia S.P.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| US6352858B1 (en) | 2000-09-11 | 2002-03-05 | Isis Pharmaceuticals, Inc. | Antisense modulation of BTAK expression |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6610677B2 (en) | 2000-09-15 | 2003-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| AU2001290912A1 (en) | 2000-09-15 | 2002-03-26 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US7473691B2 (en) | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6613776B2 (en) | 2000-09-15 | 2003-09-02 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6455559B1 (en) | 2001-07-19 | 2002-09-24 | Pharmacia Italia S.P.A. | Phenylacetamido-pyrazole derivatives, process for their preparation and their use as antitumor agents |
| AU2002215053A1 (en) | 2000-11-27 | 2002-06-24 | Pharmacia Italia S.P.A. | Phenylacetamido- pyrazole derivatives and their use as antitumor agents |
| MXPA03004714A (es) | 2000-11-28 | 2003-08-19 | Pfizer Prod Inc | Sales de una isotiazol-4-carboxamida y su uso como agentes de antihiperproliferacion. |
| FR2818278B1 (fr) * | 2000-12-20 | 2003-02-28 | Sod Conseils Rech Applic | Inhibiteurs de kinases dependantes des cyclines (cdk) et de la glycogene synthase kinase-3 (gsk-3) |
| JP2004516297A (ja) * | 2000-12-20 | 2004-06-03 | ソシエテ・ド・コンセイユ・ド・ルシエルシエ・エ・ダアツプリカーション・シヤンテイフイツク・（エス．セー．エール．アー．エス） | サイクリン依存性キナーゼ（ｃｄｋ）及びグリコーゲンシンターゼキナーゼ−３（ｇｓｋ−３）の阻害剤 |
| BR0116493A (pt) | 2000-12-21 | 2003-09-30 | Vertex Pharma | Compostos de pirazol úteis como inibidores de proteìna cinase |
| GB0102687D0 (en) | 2001-02-02 | 2001-03-21 | Pharmacia & Upjohn Spa | Oxazolyl-pyrazole derivatives active as kinase inhibitors,process for their preparation and pharmaceutical compositions comprising them |
| MY130778A (en) | 2001-02-09 | 2007-07-31 | Vertex Pharma | Heterocyclic inhibitiors of erk2 and uses thereof |
| HRP20030910B1 (hr) | 2001-05-14 | 2011-11-30 | Pfizer Products Inc. | Tartaratne soli 5,8,14-triazatetraciklo {10.3.1.0<sup>2,11</sup>.0<sup>4,9</sup>}-heksadeka-2(11), 3,5,7,9-pentaena i pripadajućih farmaceutskih spojeva |
| KR20040000507A (ko) | 2001-05-24 | 2004-01-03 | 야마노우치세이야쿠 가부시키가이샤 | 3-퀴놀린-2(1ｈ)-일리덴인돌린-2-온 유도체 |
| US20030208067A1 (en) | 2001-05-30 | 2003-11-06 | Cao Sheldon Xiaodong | Inhibitors of protein kinase for the treatment of disease |
| WO2002096905A1 (en) | 2001-06-01 | 2002-12-05 | Vertex Pharmaceuticals Incorporated | Thiazole compounds useful as inhibitors of protein kinases |
| MXPA03010961A (es) | 2001-05-31 | 2004-02-27 | Vertex Pharma | Compuestos de tiazol utiles como inhibidores de proteinas cinasas. |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| KR100824669B1 (ko) | 2001-06-22 | 2008-04-28 | 더 프록터 앤드 갬블 캄파니 | 친유액 시스템용 직물 보호 조성물 |
| GB0115393D0 (en) | 2001-06-23 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| JP2004534857A (ja) | 2001-07-19 | 2004-11-18 | フアルマシア・イタリア・エツセ・ピー・アー | フェニルアセトアミド−チアゾール誘導体、それらの製造のための方法及び抗癌剤としてのそれらの使用 |
| US20040235867A1 (en) | 2001-07-24 | 2004-11-25 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| US6872533B2 (en) | 2001-07-27 | 2005-03-29 | The Regents Of The University Of California | STK15 (STK6) gene polymorphism and methods of determining cancer risk |
| WO2003011287A1 (en) | 2001-08-03 | 2003-02-13 | Vertex Pharmaceuticals Incorporated | Pyrazolon derivatives as inhibitors of gsk-3 |
| NZ530782A (en) | 2001-08-06 | 2005-11-25 | Pharmacia Italia S | Aminoisoxazole derivatives active as kinase inhibitors |
| US20030073692A1 (en) | 2001-08-07 | 2003-04-17 | Pharmacia & Upjohn S.P.A. | Amino-phthalazinone derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them |
| WO2003020276A1 (en) | 2001-08-30 | 2003-03-13 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US6806272B2 (en) | 2001-09-04 | 2004-10-19 | Boehringer Ingelheim Pharma Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| JP2005507892A (ja) | 2001-09-19 | 2005-03-24 | ファルマシア・コーポレーション | 炎症の治療のための置換されたピラゾリルベンゼンスルファミド化合物 |
| CA2460939C (en) | 2001-09-19 | 2008-07-29 | Pharmacia Corporation | Substituted pyrazolyl compounds for the treatment of inflammation |
| EP1444207A2 (en) | 2001-09-19 | 2004-08-11 | Pharmacia Corporation | Substituted pyrazolyl-compounds for the treatment of inflammation |
| US20030109550A1 (en) | 2001-09-19 | 2003-06-12 | Michael Clare | Substituted indazole compounds for the treatment of inflammation |
| KR20040047869A (ko) | 2001-09-26 | 2004-06-05 | 파마시아 이탈리아 에스.피.에이. | 키나제 억제제로서 활성인 아미노인다졸 유도체, 이의제조방법 및 이를 함유하는 약제학적 조성물 |
| GB0124299D0 (en) | 2001-10-10 | 2001-11-28 | Astrazeneca Ab | Crystal structure of enzyme and uses thereof |
| JP4460292B2 (ja) | 2001-10-17 | 2010-05-12 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法 |
| US20040010027A1 (en) | 2001-12-17 | 2004-01-15 | Pharmacia & Upjohn Spa | Hydroxphenyl-pyrazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical comositions comprising them |
| SE0104340D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New compounds |
| ATE446093T1 (de) | 2001-12-24 | 2009-11-15 | Astrazeneca Ab | Substituierte chinazolin-derivate als aurora- kinase inhibitoren |
| FR2836914B1 (fr) | 2002-03-11 | 2008-03-14 | Aventis Pharma Sa | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| US20040009981A1 (en) | 2002-03-15 | 2004-01-15 | David Bebbington | Compositions useful as inhibitors of protein kinases |
| US6846928B2 (en) | 2002-03-15 | 2005-01-25 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| WO2003077921A1 (en) | 2002-03-15 | 2003-09-25 | Vertex Pharmaceuticals, Inc. | Azinylaminoazoles as inhibitors of protein kinases |
| AU2003225800A1 (en) | 2002-03-15 | 2003-09-29 | Hayley Binch | Azolylaminoazine as inhibitors of protein kinases |
| SE0200979D0 (sv) | 2002-03-28 | 2002-03-28 | Astrazeneca Ab | New compounds |
| JP4451136B2 (ja) | 2002-04-08 | 2010-04-14 | メルク エンド カムパニー インコーポレーテッド | Ａｋｔ活性阻害薬 |
| AU2003244978A1 (en) | 2002-04-15 | 2003-10-27 | Inserm | Methods to identify anti-tumoral agents inhibiting rasgap / aurora kinase interactions |
| EP1506189A1 (en) | 2002-04-26 | 2005-02-16 | Vertex Pharmaceuticals Incorporated | Pyrrole derivatives as inhibitors of erk2 and uses thereof |
| EP1549318B1 (en) | 2002-05-01 | 2010-02-17 | Vertex Pharmaceuticals Incorporated | Crystal structure of aurora-2 protein and binding pockets thereof |
| WO2003097610A1 (en) | 2002-05-17 | 2003-11-27 | Pharmacia Italia S.P.A. | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| JPWO2003101983A1 (ja) | 2002-05-31 | 2005-09-29 | アステラス製薬株式会社 | テトラヒドロピラン誘導体 |
| AU2002311176A1 (en) | 2002-06-12 | 2003-12-31 | Axia Biosciences, Inc. | Chfr protein-catalyzed polyubiquitination of aurora kinase a and aurora kinase b |
| FR2840905B1 (fr) | 2002-06-12 | 2006-07-07 | Centre Nat Rech Scient | Anticorps monoclonal anti-aurora-a, son procede d'obtention, et ses utilisations dans le diagnostic et le traitement des cancers |
| AU2003276005B2 (en) | 2002-06-14 | 2009-01-15 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| MY141867A (en) | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| US7361665B2 (en) | 2002-07-09 | 2008-04-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases |
| WO2004006838A2 (en) | 2002-07-15 | 2004-01-22 | Sugen, Inc. | Novel kinases |
| WO2004007504A1 (en) | 2002-07-17 | 2004-01-22 | Pharmacia Italia S.P.A. | Heterobicyclic pyrazole derivatives as kinase inhibitors |
| EP1530573B1 (en) | 2002-07-25 | 2008-03-19 | Pfizer Italia S.r.l. | Condensed heterocyclic pyrazole derivatives as kinase inhibitors |
| MXPA05000945A (es) | 2002-07-25 | 2005-05-16 | Pharmacia Italia Spa | Biciclo-pirazoles activos como inhibidores de la cinasa, procedimientos para su preparacion y composiciones farmaceuticas que los contienen. |
| US20060100233A1 (en) | 2002-07-25 | 2006-05-11 | Manuela Villa | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| AU2003262642B2 (en) | 2002-08-14 | 2010-06-17 | Vertex Pharmaceuticals Incorporated | Protein kinase inhibitors and uses thereof |
| AU2003301439A1 (en) | 2002-10-16 | 2004-05-04 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| US7262200B2 (en) | 2002-10-25 | 2007-08-28 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| US20040102360A1 (en) | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| GB0226583D0 (en) | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| US6909001B2 (en) | 2002-12-12 | 2005-06-21 | Pharmacia Corporation | Method of making tricyclic aminocyanopyridine compounds |
| UA81790C2 (uk) | 2002-12-19 | 2008-02-11 | Фармация Италия С.П.А. | Заміщені піролопіразольні похідні як інгібітори кінази |
| AU2003292435A1 (en) | 2002-12-23 | 2004-07-14 | Astrazeneca Ab | 4- (pyridin-4-ylamino) -quinazoline derivatives as anti-tumor agents |
| UA83814C2 (ru) | 2002-12-24 | 2008-08-26 | Астразенека Аб | Производные фосфонооксихиназолина и их фармацевтическое применение |
| ATE412657T1 (de) | 2002-12-24 | 2008-11-15 | Astrazeneca Ab | Therapeutische quinazolin-derivate |
| WO2004058752A1 (en) | 2002-12-24 | 2004-07-15 | Astrazeneca Ab | Quinazoline compounds |
| CL2004000016A1 (es) | 2003-01-21 | 2005-04-15 | Wyeth Corp | Compuesto derivado de cloruro de 4-amino-2-butenoilo o una sal farmaceuticamente aceptable del mismo; procedimiento para preparar dicho compuesto, util como intermediario en la sintesis de compuestos inhibidores de proteina quinasa tirosina. |
| EP1590334B1 (en) | 2003-01-30 | 2009-08-19 | Boehringer Ingelheim Pharmaceuticals Inc. | 2,4-diaminopyrimidine derivatives useful as inhibitors of pkc-theta |
| WO2004070062A2 (en) | 2003-02-04 | 2004-08-19 | Wyeth | Compositions and methods for diagnosing and treating cancers |
| WO2004071390A2 (en) | 2003-02-14 | 2004-08-26 | Applied Research Systems Ars Holding N.V. | Piperazine-2-carboxamide derivatives |
| BRPI0407544A (pt) | 2003-02-17 | 2006-02-14 | Pharmacia Italia Spa | derivados de pirazol tetracìclicos como inibidores da cinase, processo para a sua preparação e composições farmacêuticas que os compreendem |
| US6861422B2 (en) | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| DE50307267D1 (de) | 2003-02-26 | 2007-06-21 | Boehringer Ingelheim Pharma | Dihydropteridinone, verfahren zu deren herstellung und deren verwendung als arzneimittel |
| BRPI0408486A (pt) | 2003-03-11 | 2006-04-04 | Pharmacia Italia Spa | derivados de biciclopirazol ativos como inibidores da cinase, processo para a sua preparação e composições farmacêuticas compreendendo-os |
| US7456190B2 (en) | 2003-03-13 | 2008-11-25 | Vertex Pharmaceuticals Incorporated | Compositions useful as protein kinase inhibitors |
| WO2004090106A2 (en) | 2003-04-04 | 2004-10-21 | Vertex Pharmaceuticals Incorporated | Crystal structures of human pim-1 kinase protein complexes and binding pockets thereof, and uses thereof in drug design |
| RU2005135337A (ru) | 2003-04-16 | 2006-06-10 | Астразенека Аб (Se) | Производные хиназолина для лечения злокачественного новообразования |
| AU2004233828B2 (en) | 2003-04-24 | 2009-05-28 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| AU2004233827B2 (en) | 2003-04-24 | 2009-05-28 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| DE602004026047D1 (de) | 2003-04-24 | 2010-04-29 | Merck Sharp & Dohme | Hemmer der akt aktivität |
| US7414055B2 (en) | 2003-04-24 | 2008-08-19 | Merck & Co., Inc. | Inhibitors of Akt activity |
| US20040242559A1 (en) | 2003-04-25 | 2004-12-02 | Aventis Pharma S.A. | Novel indole derivatives, preparation thereof as medicinal products and pharmaceutical compositions, and especially as KDR inhibitors |
| AU2004255153B2 (en) | 2003-05-01 | 2007-11-22 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| EP1617840A4 (en) | 2003-05-01 | 2008-08-20 | Bristol Myers Squibb Co | PYRAZOLE AMID COMPOUNDS AS KINASE INHIBITORS |
| US20050125852A1 (en) | 2003-05-09 | 2005-06-09 | Sugen, Inc. | Novel kinases |
| ES2436524T3 (es) | 2003-05-22 | 2014-01-02 | Nerviano Medical Sciences S.R.L. | Derivados de pirazolo-quinazolina, procedimiento para su preparación y su uso como inhibidores de cinasas |
| US7345046B2 (en) | 2003-05-30 | 2008-03-18 | Chiron Corporation | Heteroaryl-fused pyrimidinyl compounds as anticancer agents |
| DE602004015108D1 (de) | 2003-06-02 | 2008-08-28 | Astrazeneca Ab | (3-((chinazolin-4-yl)amino)-1h-pyrazol-1-yl)acetamid derivate und verwandte verbindungen als aurora kinase inhibitoren zur behandlung von proliferativen erkrankungen wie krebs |
| TW200505452A (en) | 2003-06-17 | 2005-02-16 | Astrazeneca Ab | Chemical compounds |
| ES2339862T3 (es) | 2003-06-20 | 2010-05-26 | Novartis Vaccines And Diagnostics, Inc. | Compuestos de piridino 1,2-a-pirimidin-4-ona como agentes anticancerosos. |
| WO2005009348A2 (en) | 2003-06-25 | 2005-02-03 | Ariad Pharmaceuticals, Inc. | Substituted purine derivatives |
| AU2003304266A1 (en) | 2003-07-03 | 2005-01-21 | Cambridge University Technical Services Ltd | Use of aurora kinase inhibitors for reducing the resistance of cancer cells |
| GB0315657D0 (en) | 2003-07-03 | 2003-08-13 | Astex Technology Ltd | Pharmaceutical compounds |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| ES2322707T3 (es) | 2003-07-03 | 2009-06-25 | Euro-Celtique S.A. | Derivados de 2-piridina alquino utiles para tratar el dolor. |
| GB0315966D0 (en) | 2003-07-08 | 2003-08-13 | Cyclacel Ltd | Compounds |
| US20050032869A1 (en) | 2003-07-08 | 2005-02-10 | Pharmacia Italia S.P.A. | Pyrazolyl-indole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| US7141568B2 (en) | 2003-07-09 | 2006-11-28 | Pfizer Italia S.R.L. | Pyrrolo[3,4-c]pyrazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| EP1648900A4 (en) | 2003-07-11 | 2010-02-10 | Ariad Pharma Inc | PHOSPHORUS MACROCYCLES |
| NZ545058A (en) | 2003-07-16 | 2008-05-30 | Janssen Pharmaceutica Nv | Triazolopyrimidine derivatives as glycogen synthase kinase 3 inhibitors |
| ES2317031T3 (es) | 2003-07-16 | 2009-04-16 | Janssen Pharmaceutica Nv | Derivados de triazolopirimidina como inhibidores de la glucogeno-sintasa-quinasa 3. |
| ES2337150T3 (es) | 2003-07-21 | 2010-04-21 | Merck Serono Sa | Alquinilaril carboxamidas. |
| EP1648878B9 (en) | 2003-07-24 | 2011-03-16 | Euro-Celtique S.A. | Piperidine compounds and pharmaceutical compositions containing them |
| US7619059B2 (en) | 2003-07-29 | 2009-11-17 | Life Technologies Corporation | Bimolecular optical probes |
| US20050026984A1 (en) | 2003-07-29 | 2005-02-03 | Aventis Pharma S.A. | Substituted thieno [2,3-c] pyrazoles and their use as medicinal products |
| EP1648875A1 (en) | 2003-07-30 | 2006-04-26 | Cyclacel Limited | 2-aminophenyl-4-phenylpyrimidines as kinase inhibitors |
| JP2007500178A (ja) | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体 |
| US7094791B2 (en) | 2003-07-31 | 2006-08-22 | Avalon Pharmaceuticals, Inc. | Derivatives of 3-hydroxy-pyrrole-2,4-dicarboxylic acid and uses thereof |
| US7279575B2 (en) | 2003-08-08 | 2007-10-09 | Pfizer Italia S.R.L. | Pyrimidylpyrrole derivatives active as kinase inhibitors |
| US20050043346A1 (en) | 2003-08-08 | 2005-02-24 | Pharmacia Italia S.P.A. | Pyridylpyrrole derivatives active as kinase inhibitors |
| ATE536353T1 (de) | 2003-08-20 | 2011-12-15 | Vertex Pharma | 2-(4-amino-1,2,5-oxadiazol-4-yl)-imidazol- verbindungen als protein kinase inhibitoren |
| TWI339206B (en) | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| WO2005026155A1 (en) | 2003-09-12 | 2005-03-24 | Applied Research Systems Ars Holding N.V. | Benzimidazole acetonitriles |
| BRPI0414488A (pt) | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| WO2005026150A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| WO2005026156A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| EP1670422A4 (en) | 2003-09-17 | 2007-08-01 | Sunesis Pharmaceuticals Inc | IDENTIFYING KINASE INHIBITORS |
| KR20070064414A (ko) | 2003-09-17 | 2007-06-20 | 이코스 코포레이션 | 세포 증식 제어를 위한 ｃｈｋ1 억제제의 용도 |
| ATE433974T1 (de) | 2003-09-19 | 2009-07-15 | Gilead Sciences Inc | Azachinolinolphosphonatverbindungen als integraseinhibitoren |
| US20050085531A1 (en) | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| CA2541667A1 (en) | 2003-10-14 | 2005-04-21 | Pharmacia Corporation | Substituted pyrazinone compounds for the treatment of inflammation |
| WO2005037825A2 (en) | 2003-10-14 | 2005-04-28 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Protein kinase inhibitors |
| CN1897950A (zh) | 2003-10-14 | 2007-01-17 | 惠氏公司 | 稠合芳基和杂芳基衍生物及其使用方法 |
| ES2328820T3 (es) | 2003-10-17 | 2009-11-18 | Astrazeneca Ab | Derivados de 4-(pirazol-3-ilamino)pirimidina para uso en el tratamiento de cancer. |
| WO2005037797A1 (en) | 2003-10-21 | 2005-04-28 | Pharmacia Corporation | Substituted pyrazole urea compounds for the treatment of inflammation |
| BRPI0415759A (pt) | 2003-10-21 | 2006-12-19 | Cyclacel Ltd | compostos de pirimidin-4-il-3,4-tiona e uso dos mesmos na terapia |
| EP1678146A1 (en) | 2003-10-23 | 2006-07-12 | Pharmacia Corporation | Pyrimidine compounds for the treatment of inflammation |
| WO2005044270A1 (en) | 2003-11-04 | 2005-05-19 | 4Sc Ag | Oxadiazolopyrazine derivatives as pharmaceutically active compounds |
| AU2004289539C1 (en) | 2003-11-14 | 2012-06-07 | Lorus Therapeutics Inc. | Aryl imidazoles and their use as anti-cancer agents |
| MY141220A (en) | 2003-11-17 | 2010-03-31 | Astrazeneca Ab | Pyrazole derivatives as inhibitors of receptor tyrosine kinases |
| US20050107386A1 (en) | 2003-11-19 | 2005-05-19 | Rama Krishna Narla | Methods of treating diseases and disorders by targeting multiple kinases |
| FR2864084B1 (fr) | 2003-12-17 | 2006-02-10 | Aventis Pharma Sa | Nouveaux derives organophosphores des indazoles et leur utilisation comme medicaments |
| WO2005123672A2 (en) | 2004-06-14 | 2005-12-29 | Takeda San Diego, Inc. | Kinase inhibitors |
| FR2876377B1 (fr) | 2004-10-11 | 2007-03-16 | Univ Claude Bernard Lyon | Nouveaux derives de 9h-pyrido[2,3-b]indole, leur procede de preparation, ainsi que les compositions pharmaceutiques contenant de tels composes |
| EP1812439B2 (en) * | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US20070004684A1 (en) | 2005-06-09 | 2007-01-04 | Boehringer Ingelheim International Gmbh | Alpha-Carbolines as CDK-1 inhibitors |
| US7442700B2 (en) * | 2005-07-01 | 2008-10-28 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds useful as kinase inhibitors and methods of treating kinase-associated conditions therewith |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
-
2005
- 2005-10-14 EP EP05810353.2A patent/EP1812439B2/en not_active Expired - Lifetime
- 2005-10-14 DE DE602005023333T patent/DE602005023333D1/de not_active Expired - Lifetime
- 2005-10-14 WO PCT/US2005/037059 patent/WO2006044687A2/en not_active Ceased
- 2005-10-14 JP JP2007536949A patent/JP2008516973A/ja not_active Withdrawn
- 2005-10-14 US US11/251,616 patent/US7713973B2/en active Active
- 2005-10-14 AT AT05810353T patent/ATE479687T1/de not_active IP Right Cessation
-
2010
- 2010-04-06 US US12/755,301 patent/US8288536B2/en not_active Expired - Fee Related
-
2011
- 2011-12-26 JP JP2011284364A patent/JP5524171B2/ja not_active Expired - Fee Related
-
2013
- 2013-01-17 JP JP2013006060A patent/JP2013121966A/ja not_active Ceased
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000071129A1 (en) * | 1999-05-21 | 2000-11-30 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| WO2003000693A1 (de) * | 2001-06-22 | 2003-01-03 | Bayer Healthcare Ag | Imidazotriazine als phosphodiesterase inhibitoren |
| WO2004005291A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Heterocyclisch substituierte imidazotriazine |
| WO2004005290A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Substituierte imidazotriazine |
| US20040063715A1 (en) * | 2002-09-23 | 2004-04-01 | Schering Corporation | Novel imidazopyrazines as cyclin dependent kinase inhibitors |
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| WO2004087056A2 (en) * | 2003-03-28 | 2004-10-14 | Scios Inc. | BI-CYCLIC PYRIMIDINE INHIBITORS OF TGFβ |
| WO2004087707A1 (en) * | 2003-03-31 | 2004-10-14 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
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| JP2008545660A (ja) * | 2005-05-20 | 2008-12-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼ阻害剤として有用なピロロピリジン化合物 |
| JP2009179644A (ja) * | 2005-05-20 | 2009-08-13 | Vertex Pharmaceut Inc | プロテインキナーゼ阻害剤として有用なピロロピリジン化合物 |
| JP2012505234A (ja) * | 2008-10-08 | 2012-03-01 | ブリストル−マイヤーズ スクイブ カンパニー | ピロロトリアジンキナーゼ阻害剤 |
| JP2012517965A (ja) * | 2009-02-13 | 2012-08-09 | バイエル ファーマ アクチエンゲゼルシャフト | Ａｋｔインヒビターとしての融合されたピリミジン |
| JP2013523884A (ja) * | 2010-04-14 | 2013-06-17 | アレイ バイオファーマ、インコーポレイテッド | ＪＡＫキナーゼの阻害剤としての５，７置換イミダゾ［１，２−ｃ］ピリミジン |
| JP2015205905A (ja) * | 2010-04-14 | 2015-11-19 | アレイ バイオファーマ、インコーポレイテッド | ＪＡＫキナーゼの阻害剤としての５，７置換イミダゾ［１，２−ｃ］ピリミジン |
| JP2015518010A (ja) * | 2012-05-31 | 2015-06-25 | 上海 インスティテュート オブ マテリア メディカ、チャイニーズ アカデミー オブ サイエンシーズＳｈａｎｇｈａｉ Ｉｎｓｔｉｔｕｔｅ Ｏｆ Ｍａｔｅｒｉａ Ｍｅｄｉｃａ， Ｃｈｉｎｅｓｅ Ａｃａｄｅｍｙ Ｏｆ Ｓｃｉｅｎｃｅｓ | ピロロ［２，１−ｆ］［１，２，４］トリアジン系化合物、その製造方法および用途 |
| JP2017511365A (ja) * | 2014-04-17 | 2017-04-20 | アッヴィ・インコーポレイテッド | 複素環キナーゼ阻害薬 |
| US10280184B2 (en) | 2014-04-17 | 2019-05-07 | Abbvie Inc. | Heterocyclic kinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1812439B1 (en) | 2010-09-01 |
| WO2006044687A3 (en) | 2006-07-20 |
| US20100216765A1 (en) | 2010-08-26 |
| ATE479687T1 (de) | 2010-09-15 |
| US7713973B2 (en) | 2010-05-11 |
| JP2012102121A (ja) | 2012-05-31 |
| EP1812439B2 (en) | 2017-12-06 |
| WO2006044687A2 (en) | 2006-04-27 |
| US8288536B2 (en) | 2012-10-16 |
| JP2013121966A (ja) | 2013-06-20 |
| US20060084650A1 (en) | 2006-04-20 |
| EP1812439A2 (en) | 2007-08-01 |
| DE602005023333D1 (de) | 2010-10-14 |
| JP5524171B2 (ja) | 2014-06-18 |
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