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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| US67969005P | 2005-05-11 | 2005-05-11 | |
| PCT/US2005/037059 WO2006044687A2 (en) | 2004-10-15 | 2005-10-14 | Kinase inhibitors |
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| JP2011284364A Expired - Fee Related JP5524171B2 (ja) | 2004-10-15 | 2011-12-26 | キナーゼ阻害剤 |
| JP2013006060A Ceased JP2013121966A (ja) | 2004-10-15 | 2013-01-17 | キナーゼ阻害剤 |
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| JP2013006060A Ceased JP2013121966A (ja) | 2004-10-15 | 2013-01-17 | キナーゼ阻害剤 |
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| US (2) | US7713973B2 (https=) |
| EP (1) | EP1812439B2 (https=) |
| JP (3) | JP2008516973A (https=) |
| AT (1) | ATE479687T1 (https=) |
| DE (1) | DE602005023333D1 (https=) |
| WO (1) | WO2006044687A2 (https=) |
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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003284237A1 (en) * | 2002-10-16 | 2004-05-04 | Transport Systems, Inc. | Monorail sortation system |
| 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 |
| CN101084214A (zh) | 2004-11-17 | 2007-12-05 | 迈卡纳治疗股份有限公司 | 激酶抑制剂 |
| US7579360B2 (en) | 2005-06-09 | 2009-08-25 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I 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 |
| US7619083B2 (en) * | 2005-07-01 | 2009-11-17 | Bristol-Myers Squibb Company | Intermediates useful in preparing certain pyrrolotriazine compounds and process for making such intermediates |
| ZA200800907B (en) * | 2005-07-18 | 2010-04-28 | Bipar Sciences Inc | Treatment of cancer |
| KR101487027B1 (ko) * | 2005-09-30 | 2015-01-28 | 미카나 테라퓨틱스, 인크. | 치환된 피라졸 화합물 |
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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 |
|---|---|
| WO2006044687A2 (en) | 2006-04-27 |
| US8288536B2 (en) | 2012-10-16 |
| US20060084650A1 (en) | 2006-04-20 |
| DE602005023333D1 (de) | 2010-10-14 |
| EP1812439B1 (en) | 2010-09-01 |
| ATE479687T1 (de) | 2010-09-15 |
| JP2012102121A (ja) | 2012-05-31 |
| US20100216765A1 (en) | 2010-08-26 |
| EP1812439A2 (en) | 2007-08-01 |
| JP5524171B2 (ja) | 2014-06-18 |
| US7713973B2 (en) | 2010-05-11 |
| WO2006044687A3 (en) | 2006-07-20 |
| JP2013121966A (ja) | 2013-06-20 |
| EP1812439B2 (en) | 2017-12-06 |
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