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 (108)
| 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 |
| US7713973B2 (en) * | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| WO2006055831A2 (en) | 2004-11-17 | 2006-05-26 | Miikana Therapeutics, Inc. | Kinase inhibitors |
| 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 |
| CN102335163A (zh) * | 2005-07-18 | 2012-02-01 | 彼帕科学公司 | 癌症的治疗 |
| EP1928456B1 (en) * | 2005-09-30 | 2015-04-22 | Miikana Therapeutics, Inc. | Substituted pyrazole compounds |
| TW200808788A (en) * | 2006-04-19 | 2008-02-16 | Astellas Pharma Inc | Azolecarboxamide derivative |
| 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 |
| EP2041138B1 (en) * | 2006-07-07 | 2014-06-25 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7531539B2 (en) * | 2006-08-09 | 2009-05-12 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7605160B2 (en) * | 2006-08-09 | 2009-10-20 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| JP2010502731A (ja) | 2006-09-05 | 2010-01-28 | バイパー サイエンシズ，インコーポレイティド | Ｐａｒｐ阻害剤による脂肪酸合成の阻害、及びその治療方法 |
| WO2008030883A2 (en) * | 2006-09-05 | 2008-03-13 | Bipar Sciences, Inc. | Treatment of cancer |
| AR063581A1 (es) * | 2006-11-08 | 2009-02-04 | Schering Corp | Imidazopirazinas como inhibidores de proteina quinasa |
| US8148522B2 (en) * | 2007-01-02 | 2012-04-03 | Bristol-Myers Squibb Company | Intermediate useful in preparing certain pyrrolotriazine compounds and a process for making the intermediate |
| ES2353630T3 (es) * | 2007-01-08 | 2011-03-03 | Bristol-Myers Squibb Company | Productos intermedios útiles en la preparación de determinados compuestos de pirrolotriazina y un procedimiento de fabricación de productos intermedios. |
| DE102007012645A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| JP2010522241A (ja) | 2007-03-21 | 2010-07-01 | ブリストル−マイヤーズ スクイブ カンパニー | 増殖性疾患、アレルギー性疾患、自己免疫疾患または炎症性疾患として有用な縮合ヘテロ環化合物 |
| WO2008131050A1 (en) * | 2007-04-18 | 2008-10-30 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| CA2683152A1 (en) * | 2007-06-11 | 2008-12-18 | Miikana Therapeutics, Inc. | Substituted pyrazole compounds |
| 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 |
| ES2498065T3 (es) * | 2007-10-24 | 2014-09-24 | Astellas Pharma Inc. | Compuesto de azolcarboxamida o sal del mismo |
| US7868001B2 (en) * | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| AU2008321128A1 (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 |
| US20090149397A1 (en) * | 2007-12-07 | 2009-06-11 | Bipar Sciences | 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 |
| ES2548131T3 (es) * | 2008-01-08 | 2015-10-14 | Merck Sharp & Dohme Limited | Sales farmacéuticamente aceptables de 2-{4-[(3S)-piperidin-3-il]fenil}-2H-indazol-7-carboxamida |
| CA2710929A1 (en) * | 2008-01-28 | 2009-08-06 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| NZ587039A (en) | 2008-02-13 | 2013-01-25 | Gilead Connecticut Inc | 6-aryl-imidazo[1, 2-a]pyrazine derivatives, method of making, and method of use thereof |
| 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 |
| CN104744476B (zh) | 2008-12-08 | 2017-04-12 | 吉利德康涅狄格公司 | 咪唑并吡嗪syk抑制剂 |
| 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 |
| SG171993A1 (en) * | 2008-12-08 | 2011-07-28 | Gilead Connecticut Inc | Imidazopyrazine syk inhibitors |
| JP5487214B2 (ja) * | 2008-12-19 | 2014-05-07 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼ阻害剤として有用なカルバゾールカルボキシアミド化合物 |
| ES2539620T3 (es) | 2008-12-19 | 2015-07-02 | Cephalon, Inc. | Pirrolotriazina como inhibidor de ALK y de JAK2 |
| JP2012529535A (ja) | 2009-06-12 | 2012-11-22 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼモジュレーターとして有用なニコチンアミド化合物 |
| EP2464647B1 (en) | 2009-08-11 | 2016-09-21 | 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 |
| NZ602362A (en) | 2010-03-11 | 2014-11-28 | Gilead Connecticut Inc | Imidazopyridines syk inhibitors |
| WO2011141713A1 (en) | 2010-05-13 | 2011-11-17 | 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 |
| WO2012114222A1 (en) | 2011-02-23 | 2012-08-30 | Pfizer Inc. | IMIDAZO[5,1-f][1,2,4]TRIAZINES FOR THE TREATMENT OF NEUROLOGICAL DISORDERS |
| US9062045B2 (en) | 2011-09-15 | 2015-06-23 | Novartis Ag | Triazolopyridine compounds |
| 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 |
| CA2916504A1 (en) | 2013-06-25 | 2014-12-31 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| UY35625A (es) | 2013-06-25 | 2014-12-31 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos como inhibidores de quinasa |
| EP3027171B1 (en) | 2013-07-30 | 2020-03-25 | Gilead Connecticut, Inc. | Formulation of syk inhibitors |
| EA201791873A1 (ru) | 2013-07-30 | 2018-09-28 | Джилид Коннектикут, Инк. | Полиморф ингибиторов syk |
| KR20180002888A (ko) | 2013-12-04 | 2018-01-08 | 길리애드 사이언시즈, 인코포레이티드 | 암을 치료하는 방법 |
| US9290505B2 (en) | 2013-12-23 | 2016-03-22 | Gilead Sciences, Inc. | Substituted imidazo[1,2-a]pyrazines as Syk inhibitors |
| UY35898A (es) | 2013-12-23 | 2015-07-31 | Gilead Sciences Inc | ?compuestos inhibidores de syk y composiciones que los comprenden?. |
| US9856263B2 (en) | 2014-04-28 | 2018-01-02 | 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 |
| EP3461821B1 (en) | 2014-10-24 | 2020-05-13 | Bristol-Myers Squibb Company | Indole carboxamide compounds useful as kinase inhibitors |
| SG11201703186RA (en) | 2014-10-24 | 2017-05-30 | Bristol Myers Squibb Co | Tricyclic atropisomer compounds |
| BR112017007545A2 (pt) | 2014-10-24 | 2017-12-19 | Bristol Myers Squibb Co | derivados de carbazol |
| ES2928164T3 (es) | 2015-10-19 | 2022-11-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| MX2018005342A (es) | 2015-11-02 | 2018-08-15 | Janseen Pharmaceutica Nv | Compuesto de [1,2,4]triazolo[1,5-a]pirimidin-7-ilo. |
| HUE060680T2 (hu) | 2015-11-19 | 2023-04-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| DK3394033T3 (da) | 2015-12-22 | 2021-01-04 | Incyte Corp | Heterocykliske forbindelser som immunmodulatorer |
| WO2017148391A1 (zh) * | 2016-03-01 | 2017-09-08 | 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 |
| MA44860A (fr) | 2016-05-06 | 2019-03-13 | Incyte Holdings Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| ES2930092T3 (es) | 2016-07-14 | 2022-12-07 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3504198B1 (en) | 2016-08-29 | 2023-01-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| BR112019008163A2 (pt) | 2016-11-02 | 2019-07-09 | Janssen Pharmaceutica Nv | compostos de [1,2,4]triazolo[1,5-a]pirimidina como inibidores de pde2 |
| ES2912264T3 (es) | 2016-11-02 | 2022-05-25 | Janssen Pharmaceutica Nv | Compuestos de [1,2,4]triazolo[1,5-a]pirimidina como inhibidores de PDE2 |
| SG11201903892UA (en) | 2016-11-02 | 2019-05-30 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine derivatives as pde2 inhibitors |
| MA47123A (fr) | 2016-12-22 | 2021-03-17 | Incyte Corp | Dérivés de benzooxazole en tant qu'mmunomodulateurs |
| EP3558989B1 (en) | 2016-12-22 | 2021-04-14 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| US20180179179A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CA3047991A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| CN111217797B (zh) * | 2017-06-30 | 2021-02-05 | 北京泰德制药股份有限公司 | Rho相关蛋白激酶抑制剂、包含其的药物组合物及其制备方法和用途 |
| CN111051311A (zh) | 2017-08-25 | 2020-04-21 | 吉利德科学公司 | Syk抑制剂的多晶型物 |
| AU2019227607C1 (en) | 2018-02-27 | 2023-07-20 | Incyte Corporation | Imidazopyrimidines and triazolopyrimidines as A2A / A2B inhibitors |
| US10669271B2 (en) | 2018-03-30 | 2020-06-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| LT3790877T (lt) | 2018-05-11 | 2023-05-10 | Incyte Corporation | Tetrahidro-imidazo[4,5-c]piridino dariniai kaip pd-l1 imunomoduliatoriai |
| MA52940A (fr) | 2018-05-18 | 2021-04-28 | Incyte Corp | Dérivés de pyrimidine fusionnés utilisés en tant qu'inhibiteurs de a2a/a2b |
| CA3105721A1 (en) | 2018-07-05 | 2020-01-09 | Incyte Corporation | Fused pyrazine derivatives as a2a / a2b inhibitors |
| 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 |
| US11071730B2 (en) | 2018-10-31 | 2021-07-27 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds |
| US11203591B2 (en) | 2018-10-31 | 2021-12-21 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds |
| 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 |
| KR20210131372A (ko) | 2019-02-22 | 2021-11-02 | 크로노스 바이오, 인코포레이티드 | Syk 억제제로서의 축합된 피라진의 고체 형태 |
| 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 |
| WO2020237025A1 (en) | 2019-05-23 | 2020-11-26 | Gilead Sciences, Inc. | Substituted exo-methylene-oxindoles which are hpk1/map4k1 inhibitors |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| EP4037773A1 (en) | 2019-09-30 | 2022-08-10 | Incyte Corporation | Pyrido[3,2-d]pyrimidine compounds as immunomodulators |
| PE20230407A1 (es) | 2019-11-11 | 2023-03-07 | Incyte Corp | Sales y formas cristalinas de un inhibidor de pd-1/pd-l1 |
| EP4157848A4 (en) * | 2020-06-01 | 2024-07-17 | Nanjing Ruijie Pharma Co., Ltd. | COMPOUNDS AND THEIR USES AS SPLEEN TYROSINE KINASE INHIBITORS |
| WO2022099071A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process for making a pd-1/pd-l1 inhibitor and salts and crystalline forms thereof |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| AU2023249795A1 (en) | 2022-04-08 | 2024-10-17 | Shy Therapeutics, Llc | Compounds that interact with ras superfamily proteins for treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
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 |
| WO2004005290A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Substituierte imidazotriazine |
| WO2004005291A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Heterocyclisch 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 |
| IT7919536A0 (it) | 1978-01-25 | 1979-01-23 | Bayer Ag | Coloranti eterociclici. |
| DE2844606A1 (de) | 1978-10-13 | 1980-04-24 | Bayer Ag | Heterocyclische farbstoffe |
| GB9222253D0 (en) | 1992-10-23 | 1992-12-09 | Celltech Ltd | Chemical compounds |
| GB9304920D0 (en) | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| US6716575B2 (en) | 1995-12-18 | 2004-04-06 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
| US7119174B2 (en) | 1995-12-18 | 2006-10-10 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
| US5962312A (en) | 1995-12-18 | 1999-10-05 | Sugen, Inc. | Diagnosis and treatment of AUR-1 and/or AUR-2 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 |
| WO1998028281A1 (en) | 1996-12-23 | 1998-07-02 | 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 |
| US6294532B1 (en) | 1997-08-22 | 2001-09-25 | Zeneca Limited | Oxindolylquinazoline derivatives as angiogenesis inhibitors |
| 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 |
| WO2001007466A1 (en) | 1999-07-21 | 2001-02-01 | University Of Massachusetts | Kinase blocking polypeptides and uses thereof |
| JP4623483B2 (ja) * | 1999-08-23 | 2011-02-02 | 塩野義製薬株式会社 | ｓＰＬＡ２阻害作用を有するピロロトリアジン誘導体 |
| GB9922171D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| GB9922173D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| HUP0204413A3 (en) | 1999-09-21 | 2003-07-28 | Astrazeneca Ab | Quinazoline compounds, their preparation, their use and pharmaceutical compositions containing them |
| WO2001021596A1 (en) | 1999-09-21 | 2001-03-29 | Astrazeneca Ab | Quinazoline derivatives and their use as pharmaceuticals |
| US6455525B1 (en) | 1999-11-04 | 2002-09-24 | Cephalon, Inc. | Heterocyclic substituted pyrazolones |
| MXPA02006338A (es) | 1999-12-24 | 2002-12-13 | Aventis Pharma Ltd | Azaindoles. |
| AU2001228638A1 (en) | 2000-01-28 | 2001-08-07 | Astrazeneca Ab | Chemical compounds |
| AU782775B2 (en) | 2000-02-05 | 2005-08-25 | Vertex Pharmaceuticals Incorporated | Pyrazole compositions useful as inhibitors of ERK |
| AU782878B2 (en) | 2000-02-05 | 2005-09-08 | Vertex Pharmaceuticals Incorporated | Pyrazole compositions useful as inhibitors of erk |
| EP1134221A1 (en) | 2000-03-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines as lkB kinase inhibitors |
| EP1209158A1 (en) | 2000-11-18 | 2002-05-29 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines |
| 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 |
| EE200200715A (et) | 2000-06-28 | 2004-08-16 | Astrazeneca Ab | Asendatud kinasoliini derivaadid ja nende kasutamine inhibiitoritena |
| US20050009876A1 (en) | 2000-07-31 | 2005-01-13 | Bhagwat Shripad S. | Indazole compounds, compositions thereof and methods of treatment therewith |
| CN102060857A (zh) | 2000-08-10 | 2011-05-18 | 辉瑞意大利有限公司 | 具有激酶抑制剂活性的二环吡唑类、其制备方法和包含它们的药物组合物 |
| US6352858B1 (en) | 2000-09-11 | 2002-03-05 | Isis Pharmaceuticals, Inc. | Antisense modulation of BTAK expression |
| US6610677B2 (en) | 2000-09-15 | 2003-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002022605A1 (en) | 2000-09-15 | 2002-03-21 | 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 |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| AU2002215053A1 (en) | 2000-11-27 | 2002-06-24 | Pharmacia Italia S.P.A. | Phenylacetamido- pyrazole derivatives and their use as antitumor agents |
| 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 |
| 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) |
| WO2002050079A1 (fr) * | 2000-12-20 | 2002-06-27 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Inhibiteurs de kinases dependantes des cylines (cdk) et de la glycogene synthase kinase-3 (gsk-3) |
| AP2003002825A0 (en) | 2000-12-21 | 2003-09-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| 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 |
| JP3779682B2 (ja) | 2001-05-14 | 2006-05-31 | ファイザー・プロダクツ・インク | ５，８，１４−トリアザテトラシクロ［１０．３．１．０２，１１．０４，９］−ヘキサデカ−２（１１），３，５，７，９−ペンタンの酒石酸塩及びその医薬組成物 |
| US20050090498A1 (en) | 2001-05-24 | 2005-04-28 | Kiyohiro Samizu | 3-Quinolin-2(1h)-ylideneindolin-2-one derivative |
| JP2004534779A (ja) | 2001-05-30 | 2004-11-18 | エルジー ライフサイエンス リミテッド | 疾病治療用プロテインキナーゼ阻害剤 |
| MXPA03010961A (es) | 2001-05-31 | 2004-02-27 | Vertex Pharma | Compuestos de tiazol utiles como inhibidores de proteinas cinasas. |
| ES2274035T3 (es) | 2001-06-01 | 2007-05-16 | Vertex Pharmaceuticals Incorporated | Compuestos de tiazol utiles como inhibidores de proteina quinasas. |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| CA2447885C (en) | 2001-06-22 | 2009-05-12 | The Procter & Gamble Company | Fabric care compositions for lipophilic fluid systems |
| GB0115393D0 (en) | 2001-06-23 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| NZ530524A (en) | 2001-07-19 | 2006-12-22 | Pharmacia Italia S | Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents |
| 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 |
| AU2002342607B2 (en) | 2001-08-06 | 2006-10-19 | Pharmacia Italia S.P.A. | 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 |
| EP1427707A1 (en) | 2001-09-19 | 2004-06-16 | Pharmacia Corporation | Substituted indazole compounds for the treatment of inflammation |
| US6849653B2 (en) | 2001-09-19 | 2005-02-01 | Pharmacia Corporation | Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation |
| MXPA04002667A (es) | 2001-09-19 | 2004-06-18 | Pharmacia Corp | Compuestos de pirazolilo sustituido para el tratamiento de la inflacion. |
| EP1427706B1 (en) | 2001-09-19 | 2007-05-30 | Pharmacia Corporation | Substituted pyrazolo compounds for the treatment of inflammation |
| NZ531765A (en) | 2001-09-26 | 2006-02-24 | Pharmacia Italia S | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them |
| GB0124299D0 (en) | 2001-10-10 | 2001-11-28 | Astrazeneca Ab | Crystal structure of enzyme and uses thereof |
| EP1438053B1 (de) | 2001-10-17 | 2008-09-10 | Boehringer Ingelheim Pharma GmbH & Co.KG | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
| 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 |
| ES2333702T3 (es) | 2001-12-24 | 2010-02-26 | Astrazeneca Ab | Derivados de quinazolina sustituidos que actuan como unhibidores de cinasas aurora. |
| FR2836914B1 (fr) | 2002-03-11 | 2008-03-14 | Aventis Pharma Sa | Indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| US7179826B2 (en) | 2002-03-15 | 2007-02-20 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| US7091343B2 (en) | 2002-03-15 | 2006-08-15 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| AU2003220300A1 (en) | 2002-03-15 | 2003-09-29 | Binch, Hayley | Compositions useful as inhibitors of protein kinases |
| US20040009981A1 (en) | 2002-03-15 | 2004-01-15 | David Bebbington | Compositions useful as inhibitors of protein kinases |
| SE0200979D0 (sv) | 2002-03-28 | 2002-03-28 | Astrazeneca Ab | New compounds |
| WO2003086403A1 (en) | 2002-04-08 | 2003-10-23 | Merck & Co., Inc. | Inhibitors of akt activity |
| WO2003087395A2 (en) | 2002-04-15 | 2003-10-23 | 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 |
| WO2003092607A2 (en) | 2002-05-01 | 2003-11-13 | Vertex Pharmaceuticals Incorporated | Crystal structure of aurora-2 protein and binding pockets thereof |
| AU2003227741A1 (en) | 2002-05-17 | 2003-12-02 | Pharmacia Italia S.P.A. | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| MXPA04011930A (es) | 2002-05-31 | 2005-03-31 | Yamanouchi Pharma Co Ltd | Derivados de tetrahidropirano. |
| 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 |
| WO2003107002A1 (ja) | 2002-06-12 | 2003-12-24 | 株式会社アクシアバイオサイエンス | ｃｈｆｒタンパク質により触媒されるオーロラキナーゼＡ及びオーロラキナーゼＢのポリユビキチン化反応 |
| CA2486215A1 (en) | 2002-06-14 | 2003-12-24 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| MY141867A (en) | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| JP4570955B2 (ja) | 2002-07-09 | 2010-10-27 | バーテクス ファーマスーティカルズ インコーポレイテッド | プロテインキナーゼ阻害活性を持つイミダゾール類 |
| US20040197792A1 (en) | 2002-07-15 | 2004-10-07 | Sugen, Inc. | Novel Kinases |
| CA2492673A1 (en) | 2002-07-17 | 2004-01-22 | Pharmacia Italia S.P.A. | Heterobicyclic pyrazole derivatives as kinase inhibitors |
| CA2493637A1 (en) | 2002-07-25 | 2004-02-12 | Manuela Villa | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| EP1526852A1 (en) | 2002-07-25 | 2005-05-04 | Pharmacia Italia S.p.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| DE60319836T2 (de) | 2002-07-25 | 2009-05-07 | Pfizer Italia S.R.L. | Heterocyclische kondensierte pyrazolderivate als kinaseinhibitoren |
| US7304071B2 (en) | 2002-08-14 | 2007-12-04 | 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 |
| WO2004037814A1 (en) | 2002-10-25 | 2004-05-06 | 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 |
| WO2004056812A1 (en) | 2002-12-23 | 2004-07-08 | Astrazeneca Ab | 4- (pyridin-4-ylamino) -quinazoline derivatives as anti-tumor agents |
| EP1575946A1 (en) | 2002-12-24 | 2005-09-21 | AstraZeneca AB | Quinazoline compounds |
| MY136174A (en) | 2002-12-24 | 2008-08-29 | Astrazeneca Ab | Phosphonooxy quinazoline derivatives and their pharmaceutical use |
| WO2004058782A1 (en) | 2002-12-24 | 2004-07-15 | Astrazeneca Ab | Therapeutic quinazoline derivatives |
| 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. |
| US20040242613A1 (en) | 2003-01-30 | 2004-12-02 | Boehringer Ingelheim Pharmaceuticals, Inc. | Pyrimidine derivatives useful as inhibitors of PKC-theta |
| US20050266409A1 (en) | 2003-02-04 | 2005-12-01 | Wyeth | Compositions and methods for diagnosing, preventing, and treating cancers |
| EP1592389B1 (en) | 2003-02-14 | 2009-04-22 | Laboratoires Serono SA | Piperazine-2-carboxamide derivatives |
| WO2004071507A1 (en) | 2003-02-17 | 2004-08-26 | Pharmacia Italia S.P.A. | Tetracyclic pyrazole derivatives as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| 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 |
| DK1599478T3 (da) | 2003-02-26 | 2007-09-17 | Boehringer Ingelheim Pharma | Dihydropteridinoner, fremgangsmåde til fremstilling af disse og anvendelse af disse som lægemiddel |
| 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 |
| CA2522176A1 (en) | 2003-03-13 | 2004-09-30 | 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 |
| JP4709139B2 (ja) | 2003-04-16 | 2011-06-22 | アストラゼネカ アクチボラグ | 癌の治療のためのキナゾリン誘導体 |
| CA2522435C (en) | 2003-04-24 | 2011-04-12 | Merck & Co., Inc. | Inhibitors of akt activity |
| CA2522262A1 (en) | 2003-04-24 | 2004-11-11 | Merck & Co., Inc. | Inhibitors of akt activity |
| EP1620095A4 (en) | 2003-04-24 | 2009-04-01 | Merck & Co Inc | HEMMER OF ACT ACTIVITY |
| EP1622616B1 (en) | 2003-04-24 | 2011-06-15 | Merck Sharp & Dohme Corp. | 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 |
| DE602004029242D1 (en) | 2003-05-01 | 2010-11-04 | Bristol Myers Squibb Co | Pyrazolamidverbindungen |
| WO2005000200A2 (en) | 2003-05-09 | 2005-01-06 | Sugen, Inc. | Novel kinases |
| AU2004240772B2 (en) | 2003-05-22 | 2011-04-28 | Nerviano Medical Sciences S.R.L. | Pyrazolo-quinazoline derivatives,process for their preparation and their use as kinase inhibitors |
| US7345046B2 (en) | 2003-05-30 | 2008-03-18 | Chiron Corporation | Heteroaryl-fused pyrimidinyl compounds as anticancer agents |
| EP1635837B1 (en) | 2003-06-02 | 2008-07-16 | AstraZeneca AB | (3-((quinazolin-4-yl)amino)-1h-pyrazol-1-yl)acetamide derivatives and related compounds as aurora kinase inhibitors for the treatment of proliferative diseases such as cancer |
| TW200505452A (en) | 2003-06-17 | 2005-02-16 | Astrazeneca Ab | Chemical compounds |
| AU2004249730A1 (en) | 2003-06-20 | 2004-12-29 | Novartis Vaccines And Diagnostics, Inc. | Pyridino(1,2-A)pyrimidin-4-one compounds as anticancer agents |
| US20050065171A1 (en) | 2003-06-25 | 2005-03-24 | Shakespeare William C. | Substituted purine derivatives |
| GB0315657D0 (en) | 2003-07-03 | 2003-08-13 | Astex Technology Ltd | Pharmaceutical compounds |
| CA2531142A1 (en) | 2003-07-03 | 2005-01-13 | Cambridge University Technical Services Ltd | Use of aurora kinase inhibitors for reducing the resistance of cancer cells |
| EP1641775B1 (en) | 2003-07-03 | 2009-02-18 | Euro-Celtique S.A. | 2-pyridine alkyne derivatives useful for treating pain |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| 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 |
| GB0315966D0 (en) | 2003-07-08 | 2003-08-13 | Cyclacel Ltd | Compounds |
| 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 |
| EA011300B1 (ru) | 2003-07-16 | 2009-02-27 | Янссен Фармацевтика Н.В. | Производные триазолопиримидина в качестве ингибиторов киназы гликогенсинтазы-3 |
| ATE370142T1 (de) | 2003-07-16 | 2007-09-15 | Janssen Pharmaceutica Nv | Triazolopyrimidinderivate als inhibitoren von glycogensynthasekinase-3 |
| AU2004261400A1 (en) | 2003-07-21 | 2005-02-10 | Laboratoires Serono Sa | Alkynyl aryl carboxamides |
| DK1648878T3 (da) | 2003-07-24 | 2009-08-10 | Euro Celtique Sa | Piperidinforbindelser og farmaceutiske sammensætninger, som indeholder dem |
| 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 |
| AU2004261484A1 (en) | 2003-07-30 | 2005-02-10 | Cyclacel Limited | 2-aminophenyl-4-phenylpyrimidines as kinase inhibitors |
| WO2005012298A1 (en) | 2003-07-30 | 2005-02-10 | Cyclacel Limited | Pyridinylamino-pyrimidine derivatives as protein kinase inhibitors |
| US7094791B2 (en) | 2003-07-31 | 2006-08-22 | Avalon Pharmaceuticals, Inc. | Derivatives of 3-hydroxy-pyrrole-2,4-dicarboxylic acid and uses thereof |
| US20050043346A1 (en) | 2003-08-08 | 2005-02-24 | Pharmacia Italia S.P.A. | Pyridylpyrrole derivatives active as kinase inhibitors |
| US7279575B2 (en) | 2003-08-08 | 2007-10-09 | Pfizer Italia S.R.L. | Pyrimidylpyrrole derivatives active as kinase inhibitors |
| JP2007512230A (ja) | 2003-08-20 | 2007-05-17 | 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（４−アミノ−１，２，５−オキサジアゾール−４−イル）−ヘテロ芳香族化合物 |
| TWI339206B (en) | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| EP1667995A1 (en) | 2003-09-12 | 2006-06-14 | Applied Research Systems ARS Holding N.V. | Benzimidazole acetonitriles |
| EP1664030A1 (en) | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives |
| DK1667991T3 (da) | 2003-09-16 | 2008-08-18 | Astrazeneca Ab | Quinazolinderivater som tyrosinkinaseinhibitorer |
| CA2539049A1 (en) | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| MXPA06003110A (es) | 2003-09-17 | 2006-06-20 | Icos Corp | Uso de inhibidores de chk1 para controlar la proliferacion celular. |
| CA2539064A1 (en) | 2003-09-17 | 2005-04-21 | Sunesis Pharmaceuticals, Inc. | Identification of kinase inhibitors |
| EP1664046B1 (en) | 2003-09-19 | 2009-06-17 | Gilead Sciences, Inc. | Aza-quinolinol phosphonate integrase inhibitor compounds |
| 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 |
| ES2284054T3 (es) | 2003-10-14 | 2007-11-01 | Pharmacia Corporation | Compuestos de pirazinona sustituidos para el tratamiento de la inflamacion. |
| 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 |
| CA2542076C (en) | 2003-10-14 | 2013-02-26 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Substituted tricyclic compounds as protein kinase inhibitors |
| KR20060123164A (ko) | 2003-10-17 | 2006-12-01 | 아스트라제네카 아베 | 암 치료에 사용하기 위한 4-(피라졸-3-일아미노)피리미딘유도체 |
| WO2005037797A1 (en) | 2003-10-21 | 2005-04-28 | Pharmacia Corporation | Substituted pyrazole urea compounds for the treatment of inflammation |
| JP5164380B2 (ja) | 2003-10-21 | 2013-03-21 | サイクラセル リミテッド | ピリミジン−４−イル−３，４−チオン化合物及び治療におけるその使用 |
| CA2542514A1 (en) | 2003-10-23 | 2005-05-06 | 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 |
| WO2005047266A1 (en) | 2003-11-14 | 2005-05-26 | 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 |
| EP1791831A4 (en) | 2003-11-19 | 2009-07-08 | Signal Pharm Llc | METHOD FOR THE TREATMENT OF 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 |
| EP1773807A2 (en) | 2004-06-14 | 2007-04-18 | 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 |
| US7713973B2 (en) * | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| CA2610347A1 (en) | 2005-06-09 | 2006-06-08 | 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 US US11/251,616 patent/US7713973B2/en active Active
- 2005-10-14 WO PCT/US2005/037059 patent/WO2006044687A2/en not_active Ceased
- 2005-10-14 AT AT05810353T patent/ATE479687T1/de not_active IP Right Cessation
- 2005-10-14 JP JP2007536949A patent/JP2008516973A/ja not_active Withdrawn
- 2005-10-14 DE DE602005023333T patent/DE602005023333D1/de not_active Expired - Lifetime
- 2005-10-14 EP EP05810353.2A patent/EP1812439B2/en not_active Expired - Lifetime
-
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 |
| WO2004005290A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Substituierte imidazotriazine |
| WO2004005291A1 (de) * | 2002-07-08 | 2004-01-15 | Bayer Healthcare Ag | Heterocyclisch 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 |
| 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 |
Cited By (9)
| 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 |
| 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 |
|---|---|
| EP1812439B2 (en) | 2017-12-06 |
| WO2006044687A3 (en) | 2006-07-20 |
| ATE479687T1 (de) | 2010-09-15 |
| JP2013121966A (ja) | 2013-06-20 |
| WO2006044687A2 (en) | 2006-04-27 |
| EP1812439B1 (en) | 2010-09-01 |
| EP1812439A2 (en) | 2007-08-01 |
| JP2012102121A (ja) | 2012-05-31 |
| US20100216765A1 (en) | 2010-08-26 |
| US20060084650A1 (en) | 2006-04-20 |
| US8288536B2 (en) | 2012-10-16 |
| DE602005023333D1 (de) | 2010-10-14 |
| JP5524171B2 (ja) | 2014-06-18 |
| US7713973B2 (en) | 2010-05-11 |
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