HRP20110822T1 - Derivati pirimidin uree kao inhibitori kinaze - Google Patents
Derivati pirimidin uree kao inhibitori kinaze Download PDFInfo
- Publication number
- HRP20110822T1 HRP20110822T1 HR20110822T HRP20110822T HRP20110822T1 HR P20110822 T1 HRP20110822 T1 HR P20110822T1 HR 20110822 T HR20110822 T HR 20110822T HR P20110822 T HRP20110822 T HR P20110822T HR P20110822 T1 HRP20110822 T1 HR P20110822T1
- Authority
- HR
- Croatia
- Prior art keywords
- urea
- phenyl
- pyrimidin
- phenylamino
- methyl
- Prior art date
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- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- ZENDWEPAVHORFD-UHFFFAOYSA-N pyrimidine;urea Chemical class NC(N)=O.C1=CN=CN=C1 ZENDWEPAVHORFD-UHFFFAOYSA-N 0.000 title 1
- -1 cyano, azo Chemical group 0.000 claims abstract 57
- 150000001875 compounds Chemical class 0.000 claims abstract 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract 13
- 125000004429 atom Chemical group 0.000 claims abstract 11
- 239000012634 fragment Substances 0.000 claims abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 11
- 150000002367 halogens Chemical class 0.000 claims abstract 10
- 125000002252 acyl group Chemical group 0.000 claims abstract 9
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 8
- 125000000524 functional group Chemical group 0.000 claims abstract 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 125000006413 ring segment Chemical group 0.000 claims abstract 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims 9
- 230000001419 dependent effect Effects 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 5
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 102000001253 Protein Kinase Human genes 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 108060006633 protein kinase Proteins 0.000 claims 3
- SNTNERODRPWWRE-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[4-(4-ethylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=CC(NC(=O)NC=2C(=C(OC)C=C(OC)C=2Cl)Cl)=NC=N1 SNTNERODRPWWRE-UHFFFAOYSA-N 0.000 claims 2
- RPUVDKQPMTYQLZ-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[4-[(dimethylamino)methyl]-3-(trifluoromethyl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=C(C(CN(C)C)=CC=3)C(F)(F)F)C=2)=C1Cl RPUVDKQPMTYQLZ-UHFFFAOYSA-N 0.000 claims 2
- VQZURLPUFBDRDB-UHFFFAOYSA-N 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-[6-[3-[[2-(dimethylamino)ethyl-methylamino]methyl]anilino]pyrimidin-4-yl]-1-methylurea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)N(C)C=2N=CN=C(NC=3C=C(CN(C)CCN(C)C)C=CC=3)C=2)=C1Cl VQZURLPUFBDRDB-UHFFFAOYSA-N 0.000 claims 2
- CYHHJONFACPQLV-UHFFFAOYSA-N 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-[6-[4-[(dimethylamino)methyl]-3-(trifluoromethyl)anilino]pyrimidin-4-yl]-1-methylurea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)N(C)C=2N=CN=C(NC=3C=C(C(CN(C)C)=CC=3)C(F)(F)F)C=2)=C1Cl CYHHJONFACPQLV-UHFFFAOYSA-N 0.000 claims 2
- UZAGJCMLDCFHRJ-UHFFFAOYSA-N 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-1-[6-[3-[(4-propan-2-ylpiperazin-1-yl)methyl]anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)N(C)C=2N=CN=C(NC=3C=C(CN4CCN(CC4)C(C)C)C=CC=3)C=2)=C1Cl UZAGJCMLDCFHRJ-UHFFFAOYSA-N 0.000 claims 2
- WOZDISXAXNAGKV-UHFFFAOYSA-N 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-1-[6-[4-(4-propan-2-ylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)N(C)C=2N=CN=C(NC=3C=CC(=CC=3)N3CCN(CC3)C(C)C)C=2)=C1Cl WOZDISXAXNAGKV-UHFFFAOYSA-N 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- ONDVCAPBCZPUFJ-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=NC=N1 ONDVCAPBCZPUFJ-UHFFFAOYSA-N 0.000 claims 1
- JFAXVUMTPNOZEQ-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-3-[6-[3-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=CC=C1NC(=O)NC1=CC(NC=2C=C(C=CC=2)N2CCN(C)CC2)=NC=N1 JFAXVUMTPNOZEQ-UHFFFAOYSA-N 0.000 claims 1
- JOHQZQKMODMOBG-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-3-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=CC=C1NC(=O)NC1=CC(NC=2C=CC(=CC=2)N2CCN(C)CC2)=NC=N1 JOHQZQKMODMOBG-UHFFFAOYSA-N 0.000 claims 1
- PEUHONJVRNJDTJ-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-3-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=C(Cl)C=2)Cl)=NC=N1 PEUHONJVRNJDTJ-UHFFFAOYSA-N 0.000 claims 1
- BAMLKTOWNZMRHX-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-3-[6-[3-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC=C(OC)C(NC(=O)NC=2N=CN=C(NC=3C=C(C=CC=3)N3CCN(C)CC3)C=2)=C1 BAMLKTOWNZMRHX-UHFFFAOYSA-N 0.000 claims 1
- GVABIZWYOYJZQB-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-3-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC=C(OC)C(NC(=O)NC=2N=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)C=2)=C1 GVABIZWYOYJZQB-UHFFFAOYSA-N 0.000 claims 1
- IQEYNNUPDBAUDF-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[3-(1-methylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=C(OC4CCN(C)CC4)C=CC=3)C=2)=C1Cl IQEYNNUPDBAUDF-UHFFFAOYSA-N 0.000 claims 1
- FQQXQHUJXYNDTN-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[3-[(dimethylamino)methyl]anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=C(CN(C)C)C=CC=3)C=2)=C1Cl FQQXQHUJXYNDTN-UHFFFAOYSA-N 0.000 claims 1
- LHWYRWLFJHGACI-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[4-(1-methylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=CC(OC4CCN(C)CC4)=CC=3)C=2)=C1Cl LHWYRWLFJHGACI-UHFFFAOYSA-N 0.000 claims 1
- JPUAQFXEUPDCJR-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=CC(OCCN4CCCC4)=CC=3)C=2)=C1Cl JPUAQFXEUPDCJR-UHFFFAOYSA-N 0.000 claims 1
- YWIOAYVIQMRDMD-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[4-(4-propan-2-ylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=CC(=CC=3)N3CCN(CC3)C(C)C)C=2)=C1Cl YWIOAYVIQMRDMD-UHFFFAOYSA-N 0.000 claims 1
- UXDUSFUFGIJHNA-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)anilino]pyrimidin-4-yl]urea Chemical compound C1CN(CC)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC1=CC(NC(=O)NC=2C(=C(OC)C=C(OC)C=2Cl)Cl)=NC=N1 UXDUSFUFGIJHNA-UHFFFAOYSA-N 0.000 claims 1
- AMODZGHNGCTRRA-UHFFFAOYSA-N 1-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[6-[4-[2-(4-methylpiperazin-1-yl)ethoxy]anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC(OC)=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=CC(OCCN4CCN(C)CC4)=CC=3)C=2)=C1Cl AMODZGHNGCTRRA-UHFFFAOYSA-N 0.000 claims 1
- STCCXHZVQSYEEE-UHFFFAOYSA-N 1-(2,6-dichloro-3-methoxyphenyl)-3-[6-[3-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=C(OCCN4CCOCC4)C=CC=3)C=2)=C1Cl STCCXHZVQSYEEE-UHFFFAOYSA-N 0.000 claims 1
- JEDUXCVVPNEFCQ-UHFFFAOYSA-N 1-(2,6-dichloro-3-methoxyphenyl)-3-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound COC1=CC=C(Cl)C(NC(=O)NC=2N=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)C=2)=C1Cl JEDUXCVVPNEFCQ-UHFFFAOYSA-N 0.000 claims 1
- CHLBDDFINTVDCC-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-(4-fluoroanilino)pyrimidin-4-yl]urea Chemical compound C1=CC(F)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 CHLBDDFINTVDCC-UHFFFAOYSA-N 0.000 claims 1
- BUTAEXCLYMKONO-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-(4-morpholin-4-ylanilino)pyrimidin-4-yl]urea Chemical compound ClC1=CC=CC(Cl)=C1NC(=O)NC1=CC(NC=2C=CC(=CC=2)N2CCOCC2)=NC=N1 BUTAEXCLYMKONO-UHFFFAOYSA-N 0.000 claims 1
- HLKRNVBXRIVMEU-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-(propan-2-ylamino)pyrimidin-4-yl]urea Chemical compound C1=NC(NC(C)C)=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=N1 HLKRNVBXRIVMEU-UHFFFAOYSA-N 0.000 claims 1
- OYMJQVXUVQNUQF-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[(6-methoxypyridin-3-yl)amino]pyrimidin-4-yl]urea Chemical compound C1=NC(OC)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 OYMJQVXUVQNUQF-UHFFFAOYSA-N 0.000 claims 1
- MDHHRXRJAKBJCO-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[3-(1-piperidin-4-ylethoxy)anilino]pyrimidin-4-yl]urea Chemical compound C1CNCCC1C(C)OC(C=1)=CC=CC=1NC(N=CN=1)=CC=1NC(=O)NC1=C(Cl)C=CC=C1Cl MDHHRXRJAKBJCO-UHFFFAOYSA-N 0.000 claims 1
- VKFPIKFNJZNULQ-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[3-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound C1CN(C)CCN1C1=CC=CC(NC=2N=CN=C(NC(=O)NC=3C(=CC=CC=3Cl)Cl)C=2)=C1 VKFPIKFNJZNULQ-UHFFFAOYSA-N 0.000 claims 1
- ZZXVWCUYEGLJNT-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[3-(dimethylamino)anilino]pyrimidin-4-yl]urea Chemical compound CN(C)C1=CC=CC(NC=2N=CN=C(NC(=O)NC=3C(=CC=CC=3Cl)Cl)C=2)=C1 ZZXVWCUYEGLJNT-UHFFFAOYSA-N 0.000 claims 1
- FPXFXHIQKOGXNX-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]urea Chemical compound ClC1=CC=CC(Cl)=C1NC(=O)NC1=CC(NC=2C=CC(OCCN3CCOCC3)=CC=2)=NC=N1 FPXFXHIQKOGXNX-UHFFFAOYSA-N 0.000 claims 1
- CPUTXKUWMPIHGY-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-(3-morpholin-4-ylpropoxy)anilino]pyrimidin-4-yl]urea Chemical compound ClC1=CC=CC(Cl)=C1NC(=O)NC1=CC(NC=2C=CC(OCCCN3CCOCC3)=CC=2)=NC=N1 CPUTXKUWMPIHGY-UHFFFAOYSA-N 0.000 claims 1
- TVIUHMSOPJPIQJ-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 TVIUHMSOPJPIQJ-UHFFFAOYSA-N 0.000 claims 1
- WYZWBXMQJVAYJS-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-(diethylamino)anilino]pyrimidin-4-yl]urea Chemical compound C1=CC(N(CC)CC)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 WYZWBXMQJVAYJS-UHFFFAOYSA-N 0.000 claims 1
- PXCZLDNWAQBSFD-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-[(1-methylpiperidin-4-yl)methoxy]anilino]pyrimidin-4-yl]urea Chemical compound C1CN(C)CCC1COC(C=C1)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 PXCZLDNWAQBSFD-UHFFFAOYSA-N 0.000 claims 1
- CPXJABBOZQTLFI-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-[(4-methylpiperazin-1-yl)methyl]anilino]pyrimidin-4-yl]urea Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 CPXJABBOZQTLFI-UHFFFAOYSA-N 0.000 claims 1
- FOMAIMPXVLHOCI-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-[2-(diethylamino)ethoxy]anilino]pyrimidin-4-yl]urea Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 FOMAIMPXVLHOCI-UHFFFAOYSA-N 0.000 claims 1
- GXCFKEINILJCOB-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[6-[4-[3-(diethylamino)propoxy]anilino]pyrimidin-4-yl]urea Chemical compound C1=CC(OCCCN(CC)CC)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 GXCFKEINILJCOB-UHFFFAOYSA-N 0.000 claims 1
- KAOFLJJIEACVMS-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-3-[6-(4-morpholin-4-ylanilino)pyrimidin-4-yl]urea Chemical compound FC1=CC=CC(F)=C1NC(=O)NC1=CC(NC=2C=CC(=CC=2)N2CCOCC2)=NC=N1 KAOFLJJIEACVMS-UHFFFAOYSA-N 0.000 claims 1
- QNBKYGNYGFJLJI-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-3-[6-[3-(dimethylamino)anilino]pyrimidin-4-yl]urea Chemical compound CN(C)C1=CC=CC(NC=2N=CN=C(NC(=O)NC=3C(=CC=CC=3F)F)C=2)=C1 QNBKYGNYGFJLJI-UHFFFAOYSA-N 0.000 claims 1
- CBEAHGSDZRXLSD-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[6-(3-chloroanilino)pyrimidin-4-yl]urea Chemical compound ClC1=CC=CC(NC=2N=CN=C(NC(=O)NC=3C(=CC=CC=3)Br)C=2)=C1 CBEAHGSDZRXLSD-UHFFFAOYSA-N 0.000 claims 1
- YOWPYNNYBJCHOY-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[6-[4-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC(NC=2C=CC(OCCN3CCOCC3)=CC=2)=NC=N1 YOWPYNNYBJCHOY-UHFFFAOYSA-N 0.000 claims 1
- PKUHELRFULHKNU-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[6-[4-(3-morpholin-4-ylpropoxy)anilino]pyrimidin-4-yl]urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC(NC=2C=CC(OCCCN3CCOCC3)=CC=2)=NC=N1 PKUHELRFULHKNU-UHFFFAOYSA-N 0.000 claims 1
- TWOXRWIXUSZQKV-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2)Br)=NC=N1 TWOXRWIXUSZQKV-UHFFFAOYSA-N 0.000 claims 1
- GMMQREGORYPJAE-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[6-[4-[2-(diethylamino)ethoxy]anilino]pyrimidin-4-yl]urea Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2)Br)=NC=N1 GMMQREGORYPJAE-UHFFFAOYSA-N 0.000 claims 1
- VAZQZGBYHJJBJH-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[6-[4-[3-(diethylamino)propoxy]anilino]pyrimidin-4-yl]urea Chemical compound C1=CC(OCCCN(CC)CC)=CC=C1NC1=CC(NC(=O)NC=2C(=CC=CC=2)Br)=NC=N1 VAZQZGBYHJJBJH-UHFFFAOYSA-N 0.000 claims 1
- VQRGGSOHSMIHJJ-UHFFFAOYSA-N 1-(2-chloro-3,5-dimethoxyphenyl)-3-[6-(methylamino)pyrimidin-4-yl]urea Chemical compound C1=NC(NC)=CC(NC(=O)NC=2C(=C(OC)C=C(OC)C=2)Cl)=N1 VQRGGSOHSMIHJJ-UHFFFAOYSA-N 0.000 claims 1
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- VDBQUHCIBRFLFQ-XYPYZODXSA-N C1C[C@@H](O)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC(Cl)=CC=2Cl)Cl)=NC=N1 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC(Cl)=CC=2Cl)Cl)=NC=N1 VDBQUHCIBRFLFQ-XYPYZODXSA-N 0.000 claims 1
- GVCMGLDCJNKSNM-XYPYZODXSA-N C1C[C@@H](O)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 GVCMGLDCJNKSNM-XYPYZODXSA-N 0.000 claims 1
- KZWAEUHVSWQIRT-WKILWMFISA-N C1C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC(Cl)=CC=2Cl)Cl)=NC=N1 Chemical compound C1C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC(Cl)=CC=2Cl)Cl)=NC=N1 KZWAEUHVSWQIRT-WKILWMFISA-N 0.000 claims 1
- WZGXXLGHCOQACF-WKILWMFISA-N C1C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 Chemical compound C1C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]1NC1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 WZGXXLGHCOQACF-WKILWMFISA-N 0.000 claims 1
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- ZEOWTGPWHLSLOG-UHFFFAOYSA-N Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F Chemical compound Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F ZEOWTGPWHLSLOG-UHFFFAOYSA-N 0.000 claims 1
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- 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 claims 1
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- 101710182389 Fibroblast growth factor receptor 2 Proteins 0.000 claims 1
- 102100027844 Fibroblast growth factor receptor 4 Human genes 0.000 claims 1
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- 101100118549 Homo sapiens EGFR gene Proteins 0.000 claims 1
- 101000917134 Homo sapiens Fibroblast growth factor receptor 4 Proteins 0.000 claims 1
- 101000944174 Homo sapiens Histone acetyltransferase KAT6B Proteins 0.000 claims 1
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- GLGPZGRSCDNMMG-UHFFFAOYSA-N [4-[[6-[(2,6-dichlorophenyl)carbamoylamino]pyrimidin-4-yl]amino]cyclohexyl] n-(2,6-dichlorophenyl)carbamate Chemical compound ClC1=CC=CC(Cl)=C1NC(=O)NC1=CC(NC2CCC(CC2)OC(=O)NC=2C(=CC=CC=2Cl)Cl)=NC=N1 GLGPZGRSCDNMMG-UHFFFAOYSA-N 0.000 claims 1
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- 230000014509 gene expression Effects 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
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- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
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Classifications
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
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GBGB0512324.5A GB0512324D0 (en) | 2005-06-16 | 2005-06-16 | Organic compounds |
PCT/EP2005/006815 WO2006000420A1 (en) | 2004-06-24 | 2005-06-23 | Pyrimidine urea derivatives as kinase inhibitors |
Publications (1)
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HRP20110822T1 true HRP20110822T1 (hr) | 2012-03-31 |
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HR20110822T HRP20110822T1 (hr) | 2004-06-24 | 2011-11-08 | Derivati pirimidin uree kao inhibitori kinaze |
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EP (3) | EP2418205B1 (es) |
JP (1) | JP4944776B2 (es) |
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CN (3) | CN101035769A (es) |
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AU (2) | AU2005256491C1 (es) |
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DK (1) | DK1761505T3 (es) |
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HK (1) | HK1104286A1 (es) |
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NZ (1) | NZ551438A (es) |
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GB0512324D0 (en) * | 2005-06-16 | 2005-07-27 | Novartis Ag | Organic compounds |
JP4641839B2 (ja) * | 2005-03-23 | 2011-03-02 | セントラル硝子株式会社 | 4−メチル−3−トリフルオロメチル安息香酸の製造方法 |
WO2006124462A2 (en) * | 2005-05-13 | 2006-11-23 | Irm, Llc | Compounds and compositions as protein kinase inhibitors |
AU2006283476A1 (en) * | 2005-08-22 | 2007-03-01 | Amgen Inc. | Bis-aryl urea compounds for the treatment of protein kinase-mediated diseaes |
SMP200800041B (it) * | 2005-12-21 | 2009-07-14 | Novartis Ag | Derivati di pirimidinil-aril-urea attivi come-fgf-inibitori |
JP2009532449A (ja) * | 2006-04-05 | 2009-09-10 | アストラゼネカ アクチボラグ | 抗癌活性のある置換キナゾリン |
ES2360423T3 (es) * | 2006-04-26 | 2011-06-03 | Supernus Pharmaceuticals, Inc. | Preparaciones de liberación controlada de oxcarbazepina que tienen perfil de liberación sigmoidal. |
EP1882475A1 (en) * | 2006-07-26 | 2008-01-30 | Novartis AG | Method of treating disorders mediated by the fibroblast growth factor receptor |
US8131527B1 (en) | 2006-12-22 | 2012-03-06 | Astex Therapeutics Ltd. | FGFR pharmacophore compounds |
WO2008078091A1 (en) | 2006-12-22 | 2008-07-03 | Astex Therapeutics Limited | Bicyclic heterocyclic compounds as fgfr inhibitors |
WO2008078100A2 (en) | 2006-12-22 | 2008-07-03 | Astex Therapeutics Limited | Tricyclic amine derivatives as protein tyrosine kinase inhibitors |
ES2454966T3 (es) | 2007-02-01 | 2014-04-14 | Resverlogix Corp. | Compuestos para la prevención y el tratamiento de enfermedades cardiovasculares |
GB0720041D0 (en) | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New Compounds |
GB0720038D0 (en) | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New compounds |
CN103353532B (zh) * | 2008-04-29 | 2016-05-11 | 诺瓦提斯公司 | 监测成纤维细胞生长因子受体的激酶活性的调节的方法及所述方法的应用 |
SI2300013T1 (en) | 2008-05-21 | 2018-03-30 | Adriad Pharmacaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
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