ES2587514T3 - Inhibidores tricíclicos de quinasas - Google Patents
Inhibidores tricíclicos de quinasas Download PDFInfo
- Publication number
- ES2587514T3 ES2587514T3 ES12716781.5T ES12716781T ES2587514T3 ES 2587514 T3 ES2587514 T3 ES 2587514T3 ES 12716781 T ES12716781 T ES 12716781T ES 2587514 T3 ES2587514 T3 ES 2587514T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrimido
- amino
- imidazo
- pyrimidin
- 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.)
- Active
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- 229940043355 kinase inhibitor Drugs 0.000 title description 5
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 5
- -1 C1-6- alkyl Chemical group 0.000 claims abstract description 299
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 105
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 133
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 78
- UKAFWJUARMVPPH-UHFFFAOYSA-N 8h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)N=CNC2=N1 UKAFWJUARMVPPH-UHFFFAOYSA-N 0.000 claims description 25
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 20
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- LPWIXQTVUKDQPE-UHFFFAOYSA-N 12-(4-bromoanilino)-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(Br)=CC=3)N=C2N2C=CN=C21 LPWIXQTVUKDQPE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- WJDVIVAHSHCRQL-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(4-piperidin-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C2N2C=CN=C21 WJDVIVAHSHCRQL-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- WSTMFUSTYZOYDL-UHFFFAOYSA-N 12-(1,2,3-benzothiadiazol-5-ylamino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4N=NSC4=CC=3)N=C2N2C=CN=C21 WSTMFUSTYZOYDL-UHFFFAOYSA-N 0.000 claims description 2
- CFYZZUMUBPACPF-UHFFFAOYSA-N 12-(1,3-benzothiazol-6-ylamino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4SC=NC4=CC=3)N=C2N2C=CN=C21 CFYZZUMUBPACPF-UHFFFAOYSA-N 0.000 claims description 2
- XBXHHAXUUZSAER-UHFFFAOYSA-N 12-(4-cyclohexylanilino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3CCCCC3)N=C2N2C=CN=C21 XBXHHAXUUZSAER-UHFFFAOYSA-N 0.000 claims description 2
- GKAIUFLVMQMDHO-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GKAIUFLVMQMDHO-UHFFFAOYSA-N 0.000 claims description 2
- PLQFKOCDZHKHRX-UHFFFAOYSA-N 12-[3-chloro-4-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)C(F)(F)F)=C(Cl)C=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 PLQFKOCDZHKHRX-UHFFFAOYSA-N 0.000 claims description 2
- OXBXLTUEEZXRSD-UHFFFAOYSA-N 12-[3-chloro-4-(4-methylpiperazin-1-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 OXBXLTUEEZXRSD-UHFFFAOYSA-N 0.000 claims description 2
- KFZPTHFHLAAPLY-UHFFFAOYSA-N 12-[4-(1,4-diazepan-1-yl)-3-methylanilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCNCCC2)C(C)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl KFZPTHFHLAAPLY-UHFFFAOYSA-N 0.000 claims description 2
- JPQMJYUOSIHHNT-UHFFFAOYSA-N 12-[4-(4-acetylpiperazin-1-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 JPQMJYUOSIHHNT-UHFFFAOYSA-N 0.000 claims description 2
- TWJWRKWSQONEGU-UHFFFAOYSA-N 12-[4-(4-acetylpiperazin-1-yl)anilino]-7-(2-chloro-6-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 TWJWRKWSQONEGU-UHFFFAOYSA-N 0.000 claims description 2
- MHOWYCRQHGHKCI-UHFFFAOYSA-N 12-[[2-(cyclopropanecarbonyl)spiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl]amino]-7-(2,6-dichloro-4-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC(F)=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)C(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 MHOWYCRQHGHKCI-UHFFFAOYSA-N 0.000 claims description 2
- GFTMSJAEEHGADR-UHFFFAOYSA-N 12-anilino-7-(3-methoxy-2-methylphenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC1=CC=CC(N2C(C3=CN=C(NC=4C=CC=CC=4)N=C3N3C=CN=C32)=O)=C1C GFTMSJAEEHGADR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- SVUNWNBQQMXLGG-UHFFFAOYSA-N 4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 SVUNWNBQQMXLGG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- PBHVOWBAQKJIHE-UHFFFAOYSA-N 7-(2,4-dimethoxyphenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC1=CC(OC)=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C2N2C=CN=C21 PBHVOWBAQKJIHE-UHFFFAOYSA-N 0.000 claims description 2
- RGHKDYZHFCXXGZ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(1H-indazol-5-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C=NNC4=CC=3)N=C2N2C=CN=C21 RGHKDYZHFCXXGZ-UHFFFAOYSA-N 0.000 claims description 2
- SJKFRWBTYBCUGI-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(1H-indazol-6-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4NN=CC4=CC=3)N=C2N2C=CN=C21 SJKFRWBTYBCUGI-UHFFFAOYSA-N 0.000 claims description 2
- GGAQMONGBVYRHN-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(3,5-difluoro-4-piperazin-1-ylanilino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C(F)=C(N2CCNCC2)C(F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GGAQMONGBVYRHN-UHFFFAOYSA-N 0.000 claims description 2
- RVAPALZVDKEYRH-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(1,1,2,3,3-pentamethylisoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2C(C)(C)N(C)C(C)(C)C2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl RVAPALZVDKEYRH-UHFFFAOYSA-N 0.000 claims description 2
- FIEFUTLSNLZAGA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl FIEFUTLSNLZAGA-UHFFFAOYSA-N 0.000 claims description 2
- NNDPUBRAHKIRIP-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(2-methylsulfonyl-3,4-dihydro-1H-isoquinolin-6-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2CN(S(=O)(=O)C)CCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl NNDPUBRAHKIRIP-UHFFFAOYSA-N 0.000 claims description 2
- NZCPVWCJDIRVSB-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[(6-piperazin-1-ylpyridin-3-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=NC(=CC=3)N3CCNCC3)N=C2N2C=CN=C21 NZCPVWCJDIRVSB-UHFFFAOYSA-N 0.000 claims description 2
- IPAMMJLEAOPWRH-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[3-methoxy-4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCN(C)CC2)C(OC)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl IPAMMJLEAOPWRH-UHFFFAOYSA-N 0.000 claims description 2
- DXQPKMYOSPNPKP-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(2-oxopiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3C(CNCC3)=O)N=C2N2C=CN=C21 DXQPKMYOSPNPKP-UHFFFAOYSA-N 0.000 claims description 2
- YUSACECZXYAHRO-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(3,3-difluoropiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C(F)(F)CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 YUSACECZXYAHRO-UHFFFAOYSA-N 0.000 claims description 2
- UYFFZUITWKYKDZ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(3-oxopiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC(=O)NCC3)N=C2N2C=CN=C21 UYFFZUITWKYKDZ-UHFFFAOYSA-N 0.000 claims description 2
- JPLBPJNNOXQWAL-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4,4-difluoropiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(F)(F)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 JPLBPJNNOXQWAL-UHFFFAOYSA-N 0.000 claims description 2
- ZWUXTZDZEJUYDC-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(4-hydroxypiperidin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 ZWUXTZDZEJUYDC-UHFFFAOYSA-N 0.000 claims description 2
- FIZCVABTBXZLTR-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(7-methylsulfonyl-2,7-diazaspiro[3.4]octan-2-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1N(S(=O)(=O)C)CCC11CN(C=2C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C5=NC=CN54)=O)=CN=3)=CC=2)C1 FIZCVABTBXZLTR-UHFFFAOYSA-N 0.000 claims description 2
- ITBIXLURBFCVLL-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(9-methyl-3,9-diazaspiro[5.5]undecan-3-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCC21CCN(C=1C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C5=NC=CN54)=O)=CN=3)=CC=1)CC2 ITBIXLURBFCVLL-UHFFFAOYSA-N 0.000 claims description 2
- PJEIKZYPAJBYSN-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[1-[1-(dimethylamino)-3-methylbutyl]cyclobutyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(NC=2N=C3C(C(N(C=4C(=CC=CC=4Cl)Cl)C4=NC=CN43)=O)=CN=2)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 PJEIKZYPAJBYSN-UHFFFAOYSA-N 0.000 claims description 2
- ZCMFFRXYWPAMAF-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(dimethylamino)ethyl-ethylamino]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N(CCN(C)C)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 ZCMFFRXYWPAMAF-UHFFFAOYSA-N 0.000 claims description 2
- RCWBCGALBPUPRM-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[3-(diethylamino)propoxy]-3-fluoroanilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C(F)C(OCCCN(CC)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 RCWBCGALBPUPRM-UHFFFAOYSA-N 0.000 claims description 2
- KXAUNTOLVMSJKJ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KXAUNTOLVMSJKJ-UHFFFAOYSA-N 0.000 claims description 2
- MIUZKHQKIKYNFA-UHFFFAOYSA-N 7-(2-chloro-4,6-difluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(F)=CC=3F)Cl)C3=NC=CN3C2=N1 MIUZKHQKIKYNFA-UHFFFAOYSA-N 0.000 claims description 2
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- C—CHEMISTRY; METALLURGY
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- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| US201161447405P | 2011-02-28 | 2011-02-28 | |
| US201161447405P | 2011-02-28 | ||
| PCT/US2012/026685 WO2012161812A1 (en) | 2011-02-28 | 2012-02-27 | Tricyclic inhibitors of kinases |
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| ES2587514T3 true ES2587514T3 (es) | 2016-10-25 |
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| UY (1) | UY33925A (enExample) |
| WO (1) | WO2012161812A1 (enExample) |
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| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| PE20190736A1 (es) | 2012-06-13 | 2019-05-23 | Incyte Holdings Corp | Compuestos triciclicos sustituidos como inhibidores del receptor del factor de crecimiento de fibroblastos (fgfr) |
| WO2014026125A1 (en) | 2012-08-10 | 2014-02-13 | Incyte Corporation | Pyrazine derivatives as fgfr inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| KR102269032B1 (ko) | 2013-04-19 | 2021-06-24 | 인사이트 홀딩스 코포레이션 | Fgfr 저해제로서 이환식 헤테로사이클 |
| JPWO2015029447A1 (ja) * | 2013-08-30 | 2017-03-02 | 興和株式会社 | 光学活性カルビノール化合物の製造方法 |
| GB201322602D0 (en) | 2013-12-19 | 2014-02-05 | Almac Discovery Ltd | Pharmaceutical compounds |
| AU2015245901B2 (en) * | 2014-04-10 | 2017-05-25 | Dalhousie University | Treatment of Parkinson's disease through ArfGAP1 inhibition using substituted piperazine derivatives |
| CN107072970B (zh) * | 2014-08-29 | 2021-05-25 | 得克萨斯州大学系统董事会 | 用于治疗癌症和其他增殖性疾病的新的辣椒平类似物 |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| ES2895769T3 (es) | 2015-02-20 | 2022-02-22 | Incyte Corp | Heterociclos bicíclicos como inhibidores de FGFR |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CA3043945A1 (en) | 2016-11-16 | 2018-05-24 | Sui Xiong Cai | 8,9-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6h)-ones |
| CN110198943B (zh) * | 2017-01-23 | 2021-04-16 | 石家庄智康弘仁新药开发有限公司 | 作为Wee1抑制剂的1,2-二氢-3H-吡唑[3,4-d]嘧啶-3-酮衍生物 |
| SG11201908788YA (en) | 2017-03-31 | 2019-10-30 | Seattle Genetics Inc | Combinations of chk1- and wee1 - inhibitors |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| CN110914277B (zh) * | 2017-07-10 | 2022-08-09 | 上海瑛派药业有限公司 | 咪唑并[1,2-b]嘧啶并[4,5-d]哒嗪-5(6H)-酮类化合物及其应用 |
| JOP20200024A1 (ar) | 2017-08-04 | 2020-02-02 | Bayer Ag | مركبات ثنائي هيدروكساديازينون |
| EP3661917B1 (en) | 2017-08-04 | 2022-05-11 | Bayer Aktiengesellschaft | 6-((3-trifluoromethyl)phenyl)-4,5-dihydropyridazin-3(2h)-one derivatives as pde3a and pde3b inhibitors for treating cancer |
| CN107821390A (zh) * | 2017-10-13 | 2018-03-23 | 南京扬子鸿利源化学品有限责任公司 | 一种甲基磺草酮油悬浮剂及其制备方法 |
| WO2019085933A1 (zh) | 2017-11-01 | 2019-05-09 | 南京明德新药研发股份有限公司 | 作为Wee1抑制剂的大环类化合物及其应用 |
| SI3788047T1 (sl) | 2018-05-04 | 2024-11-29 | Incyte Corporation | Trdne oblike inhibitorja fgfr in postopki priprave le-teh |
| SG11202010882XA (en) | 2018-05-04 | 2020-11-27 | Incyte Corp | Salts of an fgfr inhibitor |
| CN108727249A (zh) * | 2018-07-07 | 2018-11-02 | 台州学院 | 3-二氟甲基哌啶盐酸盐及其衍生物的合成方法 |
| MX2021003531A (es) * | 2018-09-27 | 2021-07-21 | Betta Pharmaceuticals Co Ltd | Inhibidor de fgfr4 y su uso. |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| US12180184B2 (en) | 2018-10-26 | 2024-12-31 | Wuxi Biocity Biopharmaceutics Co., Ltd. | Pyrimidopyrazolone derivative as Wee1 inhibitor and use thereof |
| CA3128293A1 (en) | 2019-02-01 | 2020-08-06 | Bayer Aktiengesellschaft | 1,2,4-triazin-3(2h)-one compounds for the treatment of hyperproliferative diseases |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| WO2020180959A1 (en) | 2019-03-05 | 2020-09-10 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| HRP20241008T1 (hr) | 2019-04-30 | 2024-11-08 | Wuxi Biocity Biopharmaceutics Co., Ltd. | Kristalni oblik spoja inhibitora wee1 i njegova uporaba |
| US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| PH12022550361A1 (en) | 2019-08-14 | 2023-02-27 | Incyte Corp | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| CN112442049A (zh) * | 2019-09-03 | 2021-03-05 | 微境生物医药科技(上海)有限公司 | 作为Wee1抑制剂的嘧啶衍生物 |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| PE20221905A1 (es) | 2019-10-11 | 2022-12-23 | Incyte Corp | Aminas biciclicas como inhibidoras de la cdk2 |
| US11607416B2 (en) | 2019-10-14 | 2023-03-21 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US20240010655A1 (en) * | 2019-10-16 | 2024-01-11 | Impact Therapeutics (Shanghai), Inc | Dihydroimidazo pyrimido pyrimidinone compound |
| WO2021113462A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Derivatives of an fgfr inhibitor |
| EP4069696A1 (en) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN115698006B (zh) | 2020-06-17 | 2024-03-29 | 微境生物医药科技(上海)有限公司 | 作为Wee-1抑制剂的吡唑并[3，4-d]嘧啶-3-酮衍生物 |
| CN116888107A (zh) * | 2021-02-19 | 2023-10-13 | 微境生物医药科技(上海)有限公司 | 作为Wee-1抑制剂的稠环化合物 |
| WO2022221170A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| JP2024515318A (ja) * | 2021-04-30 | 2024-04-08 | ウィゲン・バイオメディシン・テクノロジー・（シャンハイ）・カンパニー・リミテッド | Ｗｅｅ－１阻害剤としての縮合環状化合物、その調製方法およびその使用 |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2022261160A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| AU2022384370A1 (en) * | 2021-11-09 | 2024-06-13 | Hangzhou Glubio Pharmaceutical Co. Ltd. | Wee1 protein kinase degradation agent and use thereof |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| CN116836184B (zh) * | 2022-03-25 | 2025-07-25 | 药雅科技(上海)有限公司 | Wee1激酶抑制剂的制备及其应用 |
| WO2024199388A1 (zh) * | 2023-03-29 | 2024-10-03 | 微境生物医药科技(上海)有限公司 | 作为myt1抑制剂的化合物 |
| CN119039287A (zh) * | 2023-05-29 | 2024-11-29 | 中国药科大学 | 一类四氢吡啶并嘧啶酮衍生物及其制备方法与应用 |
| KR20250136774A (ko) * | 2024-03-08 | 2025-09-16 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
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| AU2004261589B2 (en) | 2003-07-25 | 2008-05-22 | Novartis Ag | p-38 kinase inhibitors |
| US20050070554A1 (en) * | 2003-08-27 | 2005-03-31 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| US20050250836A1 (en) * | 2004-05-03 | 2005-11-10 | Pfizer Inc | Inhibitors of checkpoint kinases (Wee1 and Chk1) |
| AR058277A1 (es) | 2005-12-09 | 2008-01-30 | Solvay Pharm Gmbh | N- sulfamoil - piperidin - amidas, composiciones farmaceuticas que las comprenden y procedimiento para su preparacion |
| KR101555384B1 (ko) * | 2006-12-13 | 2015-09-23 | 아스카 세이야쿠 가부시키가이샤 | 퀴녹살린 유도체 |
| EP2213673B1 (en) * | 2007-10-23 | 2013-06-05 | Msd K.K. | Pyridone-substituted-dihydropyrazolopyrimidinone derivative |
| EP2303885B1 (en) | 2008-06-12 | 2013-07-03 | Merck Sharp & Dohme Corp. | Process for producing bicycloaniline derivatives |
| WO2010067886A1 (en) * | 2008-12-12 | 2010-06-17 | Banyu Pharmaceutical Co.,Ltd. | Dihydropyrimidopyrimidine derivative |
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2012
- 2012-02-24 TW TW101106325A patent/TWI532742B/zh not_active IP Right Cessation
- 2012-02-27 JP JP2013556755A patent/JP5886326B2/ja not_active Expired - Fee Related
- 2012-02-27 EP EP12716781.5A patent/EP2681221B1/en not_active Not-in-force
- 2012-02-27 UY UY0001033925A patent/UY33925A/es not_active Application Discontinuation
- 2012-02-27 ES ES12716781.5T patent/ES2587514T3/es active Active
- 2012-02-27 WO PCT/US2012/026685 patent/WO2012161812A1/en not_active Ceased
- 2012-02-27 MX MX2013009873A patent/MX340402B/es active IP Right Grant
- 2012-02-27 CA CA2827648A patent/CA2827648A1/en not_active Abandoned
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| CN103703005A (zh) | 2014-04-02 |
| MX340402B (es) | 2016-07-07 |
| US8710065B2 (en) | 2014-04-29 |
| JP2014506929A (ja) | 2014-03-20 |
| EP2681221B1 (en) | 2016-05-18 |
| CA2827648A1 (en) | 2012-11-29 |
| US20120220572A1 (en) | 2012-08-30 |
| EP2681221A1 (en) | 2014-01-08 |
| JP5886326B2 (ja) | 2016-03-16 |
| MX2013009873A (es) | 2014-03-12 |
| TWI532742B (zh) | 2016-05-11 |
| AR085502A1 (es) | 2013-10-09 |
| WO2012161812A1 (en) | 2012-11-29 |
| TW201247675A (en) | 2012-12-01 |
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