JP2002516327A5 - - Google Patents
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- Publication number
- JP2002516327A5 JP2002516327A5 JP2000550849A JP2000550849A JP2002516327A5 JP 2002516327 A5 JP2002516327 A5 JP 2002516327A5 JP 2000550849 A JP2000550849 A JP 2000550849A JP 2000550849 A JP2000550849 A JP 2000550849A JP 2002516327 A5 JP2002516327 A5 JP 2002516327A5
- Authority
- JP
- Japan
- Prior art keywords
- phenylamino
- pyrimido
- pyrimidin
- dihydro
- phenyl
- 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.)
- Abandoned
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- -1 oxime ethers Chemical class 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 27
- 229910052717 sulfur Inorganic materials 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 125000001072 heteroaryl group Chemical group 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 150000002466 imines Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000004001 thioalkyl group Chemical group 0.000 description 10
- 150000003573 thiols Chemical class 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 8
- 0 *Nc(nc1N(*)C(N2*)=O)ncc1C2=O Chemical compound *Nc(nc1N(*)C(N2*)=O)ncc1C2=O 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 5
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 239000003102 growth factor Substances 0.000 description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 150000002829 nitrogen Chemical class 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 150000002923 oximes Chemical class 0.000 description 5
- 239000001301 oxygen Chemical class 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000011593 sulfur Chemical class 0.000 description 5
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 4
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 108091000080 Phosphotransferase Proteins 0.000 description 3
- 230000033115 angiogenesis Effects 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 3
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 3
- 102000020233 phosphotransferase Human genes 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- LPUCHTNHUHOTRY-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)ethanamine Chemical compound C1CC2C(C(N)C)CC1C2 LPUCHTNHUHOTRY-UHFFFAOYSA-N 0.000 description 2
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 description 2
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 2
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 2
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 2
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 2
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 description 2
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 2
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 2
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000005518 carboxamido group Chemical group 0.000 description 2
- 229940126864 fibroblast growth factor Drugs 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- LDGZHKKSDWYYBA-UHFFFAOYSA-N 1-(3,5-dimethylheptyl)-7-[4-(4-methylpiperazin-1-yl)anilino]-3,4-dihydropyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CCC(C)CC(C)CC)C(=O)NCC2=CN=C1NC(C=C1)=CC=C1N1CCN(C)CC1 LDGZHKKSDWYYBA-UHFFFAOYSA-N 0.000 description 1
- REAXZCOCRIIZGW-UHFFFAOYSA-N 1-(3,5-dimethylheptyl)-7-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(CCC(C)CC(C)CC)C2=CC=1NC(C=C1)=CC=C1N1CCN(C)CC1 REAXZCOCRIIZGW-UHFFFAOYSA-N 0.000 description 1
- VRKQHBMOSLPUBQ-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-7-[4-(4-hydroxypiperidin-1-yl)anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NC(=O)N2C3C4CCC(C4)C3)C2=N1 VRKQHBMOSLPUBQ-UHFFFAOYSA-N 0.000 description 1
- OOJYJQIMJKZUSJ-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-7-[4-(4-methylpiperazin-1-yl)anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NC(=O)N2C3C4CCC(C4)C3)C2=N1 OOJYJQIMJKZUSJ-UHFFFAOYSA-N 0.000 description 1
- CXCVAMWLZIFURV-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-7-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(C3C4CCC(C4)C3)C(=O)N=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 CXCVAMWLZIFURV-UHFFFAOYSA-N 0.000 description 1
- WVONWGTWBWLAOJ-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-7-[4-[4-(dimethylamino)piperidin-1-yl]anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NC(=O)N2C3C4CCC(C4)C3)C2=N1 WVONWGTWBWLAOJ-UHFFFAOYSA-N 0.000 description 1
- WALFZDZPONVUIH-UHFFFAOYSA-N 1-(3-hydroxypropyl)-7-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(N=C1)=CC2=C1C=NC(=O)N2CCCO WALFZDZPONVUIH-UHFFFAOYSA-N 0.000 description 1
- FOTIWFNYARKEJV-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-5,8-dihydropyrimido[4,5-d]pyrimidin-7-yl]-3-propan-2-ylurea Chemical compound N=1C=C2CNC(NC(=O)NC(C)C)=NC2=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 FOTIWFNYARKEJV-UHFFFAOYSA-N 0.000 description 1
- ITWZTPZSUCXFBF-UHFFFAOYSA-N 1-[3-(2-chloro-3,5-dimethoxyphenyl)-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-yl]-3-ethylurea Chemical compound N=1C=C2CN(C=3C(=C(OC)C=C(OC)C=3)Cl)C(NC(=O)NCC)=NC2=NC=1NC1=CC=NC=C1 ITWZTPZSUCXFBF-UHFFFAOYSA-N 0.000 description 1
- XIBHMIOBBVHSOX-UHFFFAOYSA-N 1-[3-(2-chloro-3,5-dimethoxyphenyl)-7-[4-(diethylamino)butylamino]-4h-pyrimido[4,5-d]pyrimidin-2-yl]-3-ethylurea Chemical compound CCNC(=O)NC1=NC2=NC(NCCCCN(CC)CC)=NC=C2CN1C1=CC(OC)=CC(OC)=C1Cl XIBHMIOBBVHSOX-UHFFFAOYSA-N 0.000 description 1
- JMNNHVDOWHBZGS-UHFFFAOYSA-N 1-[3-(2-chloro-3,5-dimethoxyphenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-4h-pyrimido[4,5-d]pyrimidin-2-yl]-3-ethylurea Chemical compound N=1C=C2CN(C=3C(=C(OC)C=C(OC)C=3)Cl)C(NC(=O)NCC)=NC2=NC=1NC1=CC=C(OCCN(CC)CC)C=C1 JMNNHVDOWHBZGS-UHFFFAOYSA-N 0.000 description 1
- VZXMDOYQIUIEJB-UHFFFAOYSA-N 1-[3-(3,5-dimethoxyphenyl)-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-yl]-3-ethylurea Chemical compound N=1C=C2CN(C=3C=C(OC)C=C(OC)C=3)C(NC(=O)NCC)=NC2=NC=1NC1=CC=NC=C1 VZXMDOYQIUIEJB-UHFFFAOYSA-N 0.000 description 1
- PYVOKPNSBSGKEP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-7-[4-(4-methylpiperazin-1-yl)anilino]-3,4-dihydropyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CCCN(C)C)C(=O)NCC2=CN=C1NC(C=C1)=CC=C1N1CCN(C)CC1 PYVOKPNSBSGKEP-UHFFFAOYSA-N 0.000 description 1
- JMZBFDDWDQKWEU-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-7-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(CCCN(C)C)C2=CC=1NC(C=C1)=CC=C1N1CCN(C)CC1 JMZBFDDWDQKWEU-UHFFFAOYSA-N 0.000 description 1
- QUAQRTRBWXHSIP-UHFFFAOYSA-N 1-[7-(4-fluoroanilino)pyrimido[4,5-d]pyrimidin-2-yl]-3-methylurea Chemical compound N=1C2=NC(NC(=O)NC)=NC=C2C=NC=1NC1=CC=C(F)C=C1 QUAQRTRBWXHSIP-UHFFFAOYSA-N 0.000 description 1
- FAKVFHGYAUSYSU-UHFFFAOYSA-N 1-[7-(4-piperazin-1-ylanilino)pyrimido[4,5-d]pyrimidin-2-yl]-3-propan-2-ylurea Chemical compound N=1C2=NC(NC(=O)NC(C)C)=NC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 FAKVFHGYAUSYSU-UHFFFAOYSA-N 0.000 description 1
- DGMQKVSTMNWHCW-UHFFFAOYSA-N 1-[7-[4-(4-acetylpiperazin-1-yl)anilino]pyrimido[4,5-d]pyrimidin-2-yl]-3-propan-2-ylurea Chemical compound N=1C2=NC(NC(=O)NC(C)C)=NC=C2C=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 DGMQKVSTMNWHCW-UHFFFAOYSA-N 0.000 description 1
- SFBNZVATRDLUJJ-UHFFFAOYSA-N 1-[7-[4-[2-(diethylamino)ethoxy]anilino]-3-(3,5-dimethoxyphenyl)-4h-pyrimido[4,5-d]pyrimidin-2-yl]-3-ethylurea Chemical compound N=1C=C2CN(C=3C=C(OC)C=C(OC)C=3)C(NC(=O)NCC)=NC2=NC=1NC1=CC=C(OCCN(CC)CC)C=C1 SFBNZVATRDLUJJ-UHFFFAOYSA-N 0.000 description 1
- PJOJHRHUSQPXIS-UHFFFAOYSA-N 1-[7-[4-[3-(aminomethyl)pyrrolidin-1-yl]anilino]pyrimido[4,5-d]pyrimidin-2-yl]-3-propan-2-ylurea Chemical compound N=1C2=NC(NC(=O)NC(C)C)=NC=C2C=NC=1NC(C=C1)=CC=C1N1CCC(CN)C1 PJOJHRHUSQPXIS-UHFFFAOYSA-N 0.000 description 1
- SEGPMNJSRKJLRF-UHFFFAOYSA-N 1-cyclopentyl-7-(4-fluoro-3-methylanilino)pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1=C(F)C(C)=CC(NC=2N=C3N(C4CCCC4)C(=O)N=CC3=CN=2)=C1 SEGPMNJSRKJLRF-UHFFFAOYSA-N 0.000 description 1
- LYPJMMVRHFYBED-UHFFFAOYSA-N 1-cyclopentyl-7-(4-methylsulfonylanilino)pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC=C(C=NC(=O)N2C3CCCC3)C2=N1 LYPJMMVRHFYBED-UHFFFAOYSA-N 0.000 description 1
- HSHLNEJOCHYTQO-UHFFFAOYSA-N 1-cyclopentyl-7-(4-piperazin-1-ylanilino)pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(C3CCCC3)C(=O)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 HSHLNEJOCHYTQO-UHFFFAOYSA-N 0.000 description 1
- SIIGOVZBTPGWRM-UHFFFAOYSA-N 1-cyclopentyl-7-(4-piperazin-1-ylanilino)pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(C3CCCC3)C(=O)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 SIIGOVZBTPGWRM-UHFFFAOYSA-N 0.000 description 1
- CMPAWLHWVNKEHO-UHFFFAOYSA-N 1-cyclopentyl-7-(pyridin-4-ylamino)pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(C3CCCC3)C(=O)N=CC2=CN=C1NC1=CC=NC=C1 CMPAWLHWVNKEHO-UHFFFAOYSA-N 0.000 description 1
- CETJKWMLOZBBRP-UHFFFAOYSA-N 1-cyclopentyl-7-[4-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1C2CN(C)CC2CN1C(C=C1)=CC=C1NC(N=C12)=NC=C1C=NC(=O)N2C1CCCC1 CETJKWMLOZBBRP-UHFFFAOYSA-N 0.000 description 1
- MAFLMDDLVBFCJM-UHFFFAOYSA-N 1-cyclopentyl-7-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(C3CCCC3)C(=O)N=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 MAFLMDDLVBFCJM-UHFFFAOYSA-N 0.000 description 1
- CYLYLWLMVRIMFM-UHFFFAOYSA-N 1-hexa-2,4-dienyl-7-[4-(4-methylpiperazin-1-yl)anilino]-3,4-dihydropyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CC=CC=CC)C(=O)NCC2=CN=C1NC(C=C1)=CC=C1N1CCN(C)CC1 CYLYLWLMVRIMFM-UHFFFAOYSA-N 0.000 description 1
- MXEAYMDSLOTGOA-UHFFFAOYSA-N 1-hexa-2,4-dienyl-7-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(CC=CC=CC)C2=CC=1NC(C=C1)=CC=C1N1CCN(C)CC1 MXEAYMDSLOTGOA-UHFFFAOYSA-N 0.000 description 1
- WGFUGBMZQCPOMB-UHFFFAOYSA-N 1-methyl-7-(4-pyrazol-1-ylanilino)pyrimido[4,5-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(C)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 WGFUGBMZQCPOMB-UHFFFAOYSA-N 0.000 description 1
- KAHIEOWPOWHUDI-UHFFFAOYSA-N 1-methyl-7-[4-(4-methylpiperazin-1-yl)anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NC(=O)N2C)C2=N1 KAHIEOWPOWHUDI-UHFFFAOYSA-N 0.000 description 1
- IMKFEYLQHSBAQD-UHFFFAOYSA-N 1-methyl-7-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(C)C2=NC=1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 IMKFEYLQHSBAQD-UHFFFAOYSA-N 0.000 description 1
- NCBMKQMKSYQZJC-UHFFFAOYSA-N 1-propan-2-yl-3-[7-(pyridin-4-ylamino)pyrimido[4,5-d]pyrimidin-2-yl]urea Chemical compound N=1C2=NC(NC(=O)NC(C)C)=NC=C2C=NC=1NC1=CC=NC=C1 NCBMKQMKSYQZJC-UHFFFAOYSA-N 0.000 description 1
- NFKADCJUKLTGRB-UHFFFAOYSA-N 1-propan-2-yl-7-(4-pyrazol-1-ylanilino)pyrimido[4,5-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 NFKADCJUKLTGRB-UHFFFAOYSA-N 0.000 description 1
- RXAJHBHFVIJJLB-UHFFFAOYSA-N 1-tert-butyl-3-[3-(2-chloro-3,5-dimethoxyphenyl)-7-[4-(diethylamino)butylamino]-4h-pyrimido[4,5-d]pyrimidin-2-yl]urea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(NCCCCN(CC)CC)=NC=C2CN1C1=CC(OC)=CC(OC)=C1Cl RXAJHBHFVIJJLB-UHFFFAOYSA-N 0.000 description 1
- FAIRRWVQRAQPBG-UHFFFAOYSA-N 1-tert-butyl-3-[3-(2-chloro-3,5-dimethoxyphenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-4h-pyrimido[4,5-d]pyrimidin-2-yl]urea Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(CN(C(NC(=O)NC(C)(C)C)=N2)C=3C(=C(OC)C=C(OC)C=3)Cl)C2=N1 FAIRRWVQRAQPBG-UHFFFAOYSA-N 0.000 description 1
- RASBXSGJWSOERH-UHFFFAOYSA-N 1-tert-butyl-3-[3-(3,5-dimethoxyphenyl)-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-yl]urea Chemical compound COC1=CC(OC)=CC(N2C(=NC3=NC(NC=4C=CN=CC=4)=NC=C3C2)NC(=O)NC(C)(C)C)=C1 RASBXSGJWSOERH-UHFFFAOYSA-N 0.000 description 1
- GERNRFYVQJDHOD-UHFFFAOYSA-N 1-tert-butyl-3-[7-[4-[2-(diethylamino)ethoxy]anilino]-3-(3,5-dimethoxyphenyl)-4h-pyrimido[4,5-d]pyrimidin-2-yl]urea Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(CN(C(NC(=O)NC(C)(C)C)=N2)C=3C=C(OC)C=C(OC)C=3)C2=N1 GERNRFYVQJDHOD-UHFFFAOYSA-N 0.000 description 1
- VPNHAJYZVQXPDL-UHFFFAOYSA-N 2-[4-(2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl)anilino]-8-cyclopentyl-8h-pyrido[4,3-d]pyrimidin-7-one Chemical compound O=C1N=CC2=CN=C(NC=3C=CC(=CC=3)N3CC4CNCC4C3)N=C2C1C1CCCC1 VPNHAJYZVQXPDL-UHFFFAOYSA-N 0.000 description 1
- HIOQQUAKCHYAAB-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)anilino]-8-cyclopentyl-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound C1C(N)CCN1C(C=C1)=CC=C1NC1=NC=C(CNC(=O)N2C3CCCC3)C2=N1 HIOQQUAKCHYAAB-UHFFFAOYSA-N 0.000 description 1
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| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
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| HK1041483B (zh) * | 1998-10-23 | 2004-12-24 | 霍夫曼-拉罗奇有限公司 | 雙環氮雜環 |
| AU776250B2 (en) | 1999-10-21 | 2004-09-02 | F. Hoffmann-La Roche Ag | Heteroalkylamino-substituted bicyclic nitrogen heterocycles as inhibitors of P38 protein kinase |
| CZ20021743A3 (cs) * | 1999-10-21 | 2002-08-14 | F. Hoffmann-La Roche Ag | Bicyklické dusíkové heterocykly substituované alkylaminoskupinou jako inhibitory P38 proteinkinázy |
| SK10572002A3 (sk) * | 2000-01-24 | 2003-10-07 | Warner-Lambert Company | 3-Aminochinazolín-2,4-diónové antibakteriálne činidlá |
| CA2397961C (en) * | 2000-01-25 | 2008-08-26 | Richard John Booth | Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors |
| US7053070B2 (en) | 2000-01-25 | 2006-05-30 | Warner-Lambert Company | Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors |
| US7235551B2 (en) | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
| AR030053A1 (es) * | 2000-03-02 | 2003-08-13 | Smithkline Beecham Corp | 1h-pirimido [4,5-d] pirimidin-2-onas y sales, composiciones farmaceuticas, uso para la fabricacion de un medicamento y procedimiento para producirlas |
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| CN100525768C (zh) | 2000-10-23 | 2009-08-12 | 史密丝克莱恩比彻姆公司 | 新化合物 |
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- 1999-05-10 WO PCT/US1999/010187 patent/WO1999061444A2/en not_active Ceased
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| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
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