RU2386630C2 - Соединения и композиции в качестве ингибиторов протеинтирозинкиназы - Google Patents
Соединения и композиции в качестве ингибиторов протеинтирозинкиназы Download PDFInfo
- Publication number
- RU2386630C2 RU2386630C2 RU2008103143/04A RU2008103143A RU2386630C2 RU 2386630 C2 RU2386630 C2 RU 2386630C2 RU 2008103143/04 A RU2008103143/04 A RU 2008103143/04A RU 2008103143 A RU2008103143 A RU 2008103143A RU 2386630 C2 RU2386630 C2 RU 2386630C2
- Authority
- RU
- Russia
- Prior art keywords
- benzoimidazol
- ylamino
- pyrimidin
- trifluoromethylbenzamide
- methylphenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 21
- 239000000203 mixture Substances 0.000 title abstract 2
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title 1
- -1 imidazole-C0-4alkyl Chemical class 0.000 claims abstract 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 19
- 239000001257 hydrogen Substances 0.000 claims abstract 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract 10
- 125000004429 atom Chemical group 0.000 claims abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 8
- 150000002367 halogens Chemical class 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 claims abstract 6
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 claims abstract 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 6
- 102000001332 SRC Human genes 0.000 claims abstract 6
- 108060006706 SRC Proteins 0.000 claims abstract 6
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims abstract 6
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000006376 (C3-C10) cycloalkyl group Chemical class 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 150000003254 radicals Chemical class 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 4
- MABPYIPHMYIDIF-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methyl-n-[4-(2-methylimidazol-1-yl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound CC1=NC=CN1C(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)=C1 MABPYIPHMYIDIF-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- HTEUQPWFMDGLKN-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(4-ethylpiperazin-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HTEUQPWFMDGLKN-UHFFFAOYSA-N 0.000 claims 2
- DLDALFWGOIAFRT-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-morpholin-4-yl-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCOCC1 DLDALFWGOIAFRT-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- MQDQPOHOVUJCRE-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(2-methyl-5-nitrophenyl)benzimidazol-2-amine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 MQDQPOHOVUJCRE-UHFFFAOYSA-N 0.000 claims 1
- QMEQGSHLHUBJAH-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(4-phenoxyphenyl)benzimidazol-2-amine Chemical compound C1=NC(N)=CC(N2C3=CC=CC=C3N=C2NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 QMEQGSHLHUBJAH-UHFFFAOYSA-N 0.000 claims 1
- ZCHQKLBQZFZVBL-UHFFFAOYSA-N 2-[4-[2-methyl-6-[[6-[2-(2,4,6-trimethylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]pyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC2=CC=CC=C2N1C1=CC(NC=2N=C(C)N=C(C=2)N2CCN(CCO)CC2)=NC=N1 ZCHQKLBQZFZVBL-UHFFFAOYSA-N 0.000 claims 1
- PAOFCZHAUIKUDF-UHFFFAOYSA-N 2-[4-[6-[[6-(2-chlorobenzimidazol-1-yl)pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound N=1C(C)=NC(NC=2N=CN=C(C=2)N2C3=CC=CC=C3N=C2Cl)=CC=1N1CCN(CCO)CC1 PAOFCZHAUIKUDF-UHFFFAOYSA-N 0.000 claims 1
- ZFGRQAXIHZXQBZ-UHFFFAOYSA-N 2-[4-[6-[[6-[2-(2-chloro-6-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(N=CN=1)=CC=1N(C1=CC=CC=C1N=1)C=1NC1=C(C)C=CC=C1Cl ZFGRQAXIHZXQBZ-UHFFFAOYSA-N 0.000 claims 1
- AKGZCBJCSSQLLS-UHFFFAOYSA-N 2-[4-[6-[[6-[2-(4-bromo-2-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(N=CN=1)=CC=1N(C1=CC=CC=C1N=1)C=1NC1=CC=C(Br)C=C1C AKGZCBJCSSQLLS-UHFFFAOYSA-N 0.000 claims 1
- GTBRMMWAOBROMF-UHFFFAOYSA-N 2-[4-[6-[[6-[2-(5-methoxy-2-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound COC1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NC=3N=C(C)N=C(C=3)N3CCN(CCO)CC3)C=2)=C1 GTBRMMWAOBROMF-UHFFFAOYSA-N 0.000 claims 1
- HUEUNRUAWYBCTL-UHFFFAOYSA-N 3-(1-methylpiperidin-4-yl)oxy-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1OC1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HUEUNRUAWYBCTL-UHFFFAOYSA-N 0.000 claims 1
- HLZLAQGJKOZBRL-UHFFFAOYSA-N 3-(4-ethylpiperazin-1-yl)-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HLZLAQGJKOZBRL-UHFFFAOYSA-N 0.000 claims 1
- VSMPOKKWINPFAX-UHFFFAOYSA-N 3-(4-methylimidazol-1-yl)-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1=NC(C)=CN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 VSMPOKKWINPFAX-UHFFFAOYSA-N 0.000 claims 1
- DQDDAVDAKOJGAJ-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 DQDDAVDAKOJGAJ-UHFFFAOYSA-N 0.000 claims 1
- UPYUXTOZRFMXCW-UHFFFAOYSA-N 3-[3-(dimethylamino)pyrrolidin-1-yl]-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1C(N(C)C)CCN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 UPYUXTOZRFMXCW-UHFFFAOYSA-N 0.000 claims 1
- XWTZPPPOJTYYGH-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCN(CCO)CC1 XWTZPPPOJTYYGH-UHFFFAOYSA-N 0.000 claims 1
- CYTADLUJFNFLQB-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-2,5-dimethoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(OC)=CC(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)=C1OC CYTADLUJFNFLQB-UHFFFAOYSA-N 0.000 claims 1
- OJANARVSPGQGCL-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 OJANARVSPGQGCL-UHFFFAOYSA-N 0.000 claims 1
- PFIQMKZHLWNUCL-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-n-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound C1CN(CC)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)=C1 PFIQMKZHLWNUCL-UHFFFAOYSA-N 0.000 claims 1
- AGYCTUZXJHRHMX-UHFFFAOYSA-N 3-n-[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]-4-methylbenzene-1,3-diamine Chemical compound CC1=CC=C(N)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 AGYCTUZXJHRHMX-UHFFFAOYSA-N 0.000 claims 1
- NQYGSGQCRJPLIU-UHFFFAOYSA-N 4-methyl-3-n-(1-pyrimidin-4-ylbenzimidazol-2-yl)benzene-1,3-diamine Chemical compound CC1=CC=C(N)C=C1NC1=NC2=CC=CC=C2N1C1=CC=NC=N1 NQYGSGQCRJPLIU-UHFFFAOYSA-N 0.000 claims 1
- NHCXWLVIQSCNPV-UHFFFAOYSA-N 4-n-[6-[2-(2-chloro-6-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]-5-methyl-4-n-(2-morpholin-4-ylethyl)pyrimidine-4,6-diamine Chemical compound CC1=CC=CC(Cl)=C1NC1=NC2=CC=CC=C2N1C1=CC(N(CCN2CCOCC2)C=2C(=C(N)N=CN=2)C)=NC=N1 NHCXWLVIQSCNPV-UHFFFAOYSA-N 0.000 claims 1
- BLPQOFPQFKZYDY-UHFFFAOYSA-N CC(C)(C)N(C(CN1CCN(C)CC1)=C1)N=C1C(O)=O.CC(C=CC(N)=C1)=C1NC1=NC(C=CC=C2)=C2N1C1=NC=NC(N)=C1 Chemical compound CC(C)(C)N(C(CN1CCN(C)CC1)=C1)N=C1C(O)=O.CC(C=CC(N)=C1)=C1NC1=NC(C=CC=C2)=C2N1C1=NC=NC(N)=C1 BLPQOFPQFKZYDY-UHFFFAOYSA-N 0.000 claims 1
- JPRCFADQCQIMAE-UHFFFAOYSA-N CC(C)C(CO)NC1=CC(N2C(NC3=C(C)C=CC(C(C(C(F)(F)F)=CC=C4)=C4C(N)=O)=C3)=NC3=C2C=CC=C3)=NC=N1 Chemical compound CC(C)C(CO)NC1=CC(N2C(NC3=C(C)C=CC(C(C(C(F)(F)F)=CC=C4)=C4C(N)=O)=C3)=NC3=C2C=CC=C3)=NC=N1 JPRCFADQCQIMAE-UHFFFAOYSA-N 0.000 claims 1
- ZZUAKVFPUQAOKD-UHFFFAOYSA-N CC1=C(C=C(C=C1)C1=C(SC(=C1)C(C)(C)C)C(=O)N)NC1=NC2=C(N1C1=NC=NC=C1)C=CC=C2 Chemical compound CC1=C(C=C(C=C1)C1=C(SC(=C1)C(C)(C)C)C(=O)N)NC1=NC2=C(N1C1=NC=NC=C1)C=CC=C2 ZZUAKVFPUQAOKD-UHFFFAOYSA-N 0.000 claims 1
- ALJCNQSPZXWTBG-UHFFFAOYSA-N CC1=CC(C(O)=O)=NO1.CC(C=CC(N)=C1)=C1NC1=NC(C=CC=C2)=C2N1C1=NC=NC=C1 Chemical compound CC1=CC(C(O)=O)=NO1.CC(C=CC(N)=C1)=C1NC1=NC(C=CC=C2)=C2N1C1=NC=NC=C1 ALJCNQSPZXWTBG-UHFFFAOYSA-N 0.000 claims 1
- BJZKCXVPWVQAQR-UHFFFAOYSA-N CC1=NN(C)C(C(O)=O)=C1.CC(C=CC(N)=C1)=C1NC1=NC(C=CC=C2)=C2N1C1=NC=NC=C1 Chemical compound CC1=NN(C)C(C(O)=O)=C1.CC(C=CC(N)=C1)=C1NC1=NC(C=CC=C2)=C2N1C1=NC=NC=C1 BJZKCXVPWVQAQR-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 241001130469 Tila Species 0.000 claims 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000006393 methylpyrimidinyl group Chemical group 0.000 claims 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- PICSDTONCAVDKS-UHFFFAOYSA-N n-(2-methylphenyl)-1-pyrimidin-4-ylbenzimidazol-2-amine Chemical compound CC1=CC=CC=C1NC1=NC2=CC=CC=C2N1C1=CC=NC=N1 PICSDTONCAVDKS-UHFFFAOYSA-N 0.000 claims 1
- VXYKTIWYKXNBLX-UHFFFAOYSA-N n-[3-[[1-(6-amino-5-methylpyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2C(=C(N)N=CN=2)C)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 VXYKTIWYKXNBLX-UHFFFAOYSA-N 0.000 claims 1
- INIPJCMUHKXHJQ-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(1-methylpiperidin-4-yl)oxy-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1OC1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 INIPJCMUHKXHJQ-UHFFFAOYSA-N 0.000 claims 1
- YXQXVCBCHOYWDX-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=NC(C)=CN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 YXQXVCBCHOYWDX-UHFFFAOYSA-N 0.000 claims 1
- YQPHBBQBBMIYLO-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 YQPHBBQBBMIYLO-UHFFFAOYSA-N 0.000 claims 1
- OBLWMYNSTHSSDS-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 OBLWMYNSTHSSDS-UHFFFAOYSA-N 0.000 claims 1
- QJHCDMJHHLYGOJ-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-[(4-ethylpiperazin-1-yl)methyl]-5-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1CC1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 QJHCDMJHHLYGOJ-UHFFFAOYSA-N 0.000 claims 1
- SOLCZUBPADGMSF-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-chlorobenzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(Cl)=C1 SOLCZUBPADGMSF-UHFFFAOYSA-N 0.000 claims 1
- AYZBGELVIWCHIM-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=C1 AYZBGELVIWCHIM-UHFFFAOYSA-N 0.000 claims 1
- ZMLDJYQUOIGKDY-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-4-(2-methylimidazol-1-yl)-3-(trifluoromethyl)benzamide Chemical compound CC1=NC=CN1C1=CC=C(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)C=C1C(F)(F)F ZMLDJYQUOIGKDY-UHFFFAOYSA-N 0.000 claims 1
- NWSIWGBYWGMCQL-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-4-morpholin-4-yl-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C(C=C1C(F)(F)F)=CC=C1N1CCOCC1 NWSIWGBYWGMCQL-UHFFFAOYSA-N 0.000 claims 1
- YCGAVAFYTUFYPA-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-5-cyclopropyl-1h-pyrazole-3-carboxamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C(NN=1)=CC=1C1CC1 YCGAVAFYTUFYPA-UHFFFAOYSA-N 0.000 claims 1
- SAMCEVLBPWDZMX-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-5-tert-butyl-2-methylpyrazole-3-carboxamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC(C(C)(C)C)=NN1C SAMCEVLBPWDZMX-UHFFFAOYSA-N 0.000 claims 1
- JDFGIOCJMJJUNK-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-5-tert-butylthiophene-2-carboxamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC=C(C(C)(C)C)S1 JDFGIOCJMJJUNK-UHFFFAOYSA-N 0.000 claims 1
- QJJCDXBVFBLEDI-UHFFFAOYSA-N n-[3-[[1-(6-chloro-5-methylpyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2C(=C(Cl)N=CN=2)C)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 QJJCDXBVFBLEDI-UHFFFAOYSA-N 0.000 claims 1
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- VEXPKIRCYBYITI-UHFFFAOYSA-N n-[3-[[1-(6-methoxypyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(OC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 VEXPKIRCYBYITI-UHFFFAOYSA-N 0.000 claims 1
- DIORRHNKSLCDFP-UHFFFAOYSA-N n-[3-[[1-[6-(2,3-dihydroxypropylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCC(O)CO)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 DIORRHNKSLCDFP-UHFFFAOYSA-N 0.000 claims 1
- HHVUDVWMACNSOB-UHFFFAOYSA-N n-[3-[[1-[6-(2-hydroxyethylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCCO)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 HHVUDVWMACNSOB-UHFFFAOYSA-N 0.000 claims 1
- WLXHZMYOVDOALX-UHFFFAOYSA-N n-[3-[[1-[6-(2-methoxyethylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCOC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 WLXHZMYOVDOALX-UHFFFAOYSA-N 0.000 claims 1
- VRMZWFNHUNLCMF-UHFFFAOYSA-N n-[3-[[1-[6-[(1-ethylpyrrolidin-2-yl)methylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound CCN1CCCC1CNC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 VRMZWFNHUNLCMF-UHFFFAOYSA-N 0.000 claims 1
- REZFVUNAFUHYBW-UHFFFAOYSA-N n-[3-[[1-[6-[(4-aminocyclohexyl)amino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NC3CCC(N)CC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 REZFVUNAFUHYBW-UHFFFAOYSA-N 0.000 claims 1
- REDBMKRPRFVCHI-UHFFFAOYSA-N n-[3-[[1-[6-[2-(diethylamino)ethylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 REDBMKRPRFVCHI-UHFFFAOYSA-N 0.000 claims 1
- HOXAMYRZFGYTNX-UHFFFAOYSA-N n-[3-[[1-[6-[2-(dimethylamino)ethoxy]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(OCCN(C)C)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 HOXAMYRZFGYTNX-UHFFFAOYSA-N 0.000 claims 1
- SDPBPKTXHBUBMX-UHFFFAOYSA-N n-[3-[[1-[6-[4-(diethylamino)butylamino]-5-methylpyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound CCN(CC)CCCCNC1=NC=NC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=C1C SDPBPKTXHBUBMX-UHFFFAOYSA-N 0.000 claims 1
- ZJEDGXGHFKCGDV-UHFFFAOYSA-N n-[3-[[1-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=C(C=3)N3C=C(C)N=C3)C(F)(F)F)C=2)C)=N1 ZJEDGXGHFKCGDV-UHFFFAOYSA-N 0.000 claims 1
- FITNUKNIUJHPPH-UHFFFAOYSA-N n-[3-[[1-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 FITNUKNIUJHPPH-UHFFFAOYSA-N 0.000 claims 1
- HYCVSFKPKWAMAX-UHFFFAOYSA-N n-[3-[[1-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-4-(2-methylimidazol-1-yl)-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C(=CC=3)N3C(=NC=C3)C)C(F)(F)F)C=2)C)=N1 HYCVSFKPKWAMAX-UHFFFAOYSA-N 0.000 claims 1
- YBNOBYHPBBOUFT-UHFFFAOYSA-N n-[3-[[1-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C(CN4CCN(CC)CC4)=CC=3)C(F)(F)F)C=2)C)=N1 YBNOBYHPBBOUFT-UHFFFAOYSA-N 0.000 claims 1
- UOJUQBSCCIRCHS-UHFFFAOYSA-N n-[3-[[1-[6-[4-(dimethylamino)butylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(C)C)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 UOJUQBSCCIRCHS-UHFFFAOYSA-N 0.000 claims 1
- ONCSNTLXPGJUAI-UHFFFAOYSA-N n-[3-[[1-[6-[[4-(2-hydroxyethyl)piperazin-1-yl]amino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NN3CCN(CCO)CC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 ONCSNTLXPGJUAI-UHFFFAOYSA-N 0.000 claims 1
- OACBNSSQHGNVAI-UHFFFAOYSA-N n-[3-[[3-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]imidazo[4,5-b]pyridin-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=NC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 OACBNSSQHGNVAI-UHFFFAOYSA-N 0.000 claims 1
- QGDUBFDIQPISBZ-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-(piperidin-4-ylamino)-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1NC1CCNCC1 QGDUBFDIQPISBZ-UHFFFAOYSA-N 0.000 claims 1
- XZGBSCJUAQDTBL-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 XZGBSCJUAQDTBL-UHFFFAOYSA-N 0.000 claims 1
- NNLIMNLYBCBYQJ-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-piperazin-1-yl-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCNCC1 NNLIMNLYBCBYQJ-UHFFFAOYSA-N 0.000 claims 1
- XHZSFDNNTPIEDH-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-piperidin-4-yloxy-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1OC1CCNCC1 XHZSFDNNTPIEDH-UHFFFAOYSA-N 0.000 claims 1
- JQAVGDHDTJHEOD-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-pyrrolidin-2-yloxy-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1OC1CCCN1 JQAVGDHDTJHEOD-UHFFFAOYSA-N 0.000 claims 1
- YBQBSRIBXPKWKC-UHFFFAOYSA-N n-[4-methyl-3-[[1-(1h-pyrazolo[3,4-d]pyrimidin-4-yl)benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2C=3C=NNC=3N=CN=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YBQBSRIBXPKWKC-UHFFFAOYSA-N 0.000 claims 1
- GGEALBVZDVXUND-UHFFFAOYSA-N n-[4-methyl-3-[[1-(6-morpholin-4-ylpyrimidin-4-yl)benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(C=2)N2CCOCC2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GGEALBVZDVXUND-UHFFFAOYSA-N 0.000 claims 1
- QNTVHKHUPBDBQF-UHFFFAOYSA-N n-[4-methyl-3-[[1-[5-methyl-6-[2-(4-methylpiperazin-1-yl)ethylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCNC1=NC=NC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=C1C QNTVHKHUPBDBQF-UHFFFAOYSA-N 0.000 claims 1
- CIIHDSYJQQIKAC-UHFFFAOYSA-N n-[4-methyl-3-[[1-[5-methyl-6-[3-(4-methylpiperazin-1-yl)propylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCCNC1=NC=NC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=C1C CIIHDSYJQQIKAC-UHFFFAOYSA-N 0.000 claims 1
- GLYDCPPHXDVIKA-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-(2-pyridin-2-ylethylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCCC=3N=CC=CC=3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GLYDCPPHXDVIKA-UHFFFAOYSA-N 0.000 claims 1
- SLGMHHPVSAPRLI-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCCN3CCCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 SLGMHHPVSAPRLI-UHFFFAOYSA-N 0.000 claims 1
- UOJGMLQOPYVDAD-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-(3-morpholin-4-ylpropylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 UOJGMLQOPYVDAD-UHFFFAOYSA-N 0.000 claims 1
- QQVLIPDYPZXRET-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-[(1-methylpiperidin-4-yl)amino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1NC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 QQVLIPDYPZXRET-UHFFFAOYSA-N 0.000 claims 1
- XAWZDGHYUZKTTO-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-[(4-methylpiperazin-1-yl)amino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1NC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 XAWZDGHYUZKTTO-UHFFFAOYSA-N 0.000 claims 1
- DUSWCXDALWVDSK-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-[2-(4-methylpiperazin-1-yl)ethylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCNC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 DUSWCXDALWVDSK-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 230000002159 abnormal effect Effects 0.000 abstract 2
- 201000010099 disease Diseases 0.000 abstract 2
- 208000035475 disorder Diseases 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 108091000080 Phosphotransferase Proteins 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 102000020233 phosphotransferase Human genes 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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| US69617405P | 2005-07-01 | 2005-07-01 | |
| US60/696,174 | 2005-07-01 |
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Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| PT1599468E (pt) | 2003-01-14 | 2008-01-14 | Arena Pharm Inc | Derivados de arilo e heteroarilo 1,2,3.-trissubstituídos comomoduladores do metabolismo, e profilaxia e tratamento dedesordens relacionadas tais como diabetes e hiperglicemia |
| AR045047A1 (es) * | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| EP2287165A3 (en) | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| MX2009002046A (es) | 2006-08-24 | 2009-03-06 | Astrazeneca Ab | Derivados de morfolino pirimidina utiles en el tratamiento de trastornos proliferativos. |
| WO2008153701A1 (en) * | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| CN101809002B (zh) | 2007-07-09 | 2013-03-27 | 阿斯利康(瑞典)有限公司 | 用于与mtor激酶和/或pi3k相关的疾病中的吗啉代嘧啶衍生物 |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| AU2009248923B2 (en) | 2008-05-21 | 2015-01-29 | Takeda Pharmaceutical Company Limited | Phosphorous derivatives as kinase inhibitors |
| CA2729012A1 (en) | 2008-06-27 | 2009-12-30 | Amgen Inc. | Ang-2 inhibition to treat multiple sclerosis |
| PA8851101A1 (es) * | 2008-12-16 | 2010-07-27 | Lilly Co Eli | Compuesto amino pirazol |
| JP2012518037A (ja) * | 2009-02-18 | 2012-08-09 | アムジエン・インコーポレーテツド | ｍＴＯＲキナーゼ阻害剤としてのインドール／ベンゾイミダゾール化合物 |
| WO2010100127A1 (en) * | 2009-03-04 | 2010-09-10 | Novartis Ag | Disubstituted imidazole derivatives as modulators of raf kinase |
| SA111320519B1 (ar) * | 2010-06-11 | 2014-07-02 | Astrazeneca Ab | مركبات بيريميدينيل للاستخدام كمثبطات atr |
| WO2011157787A1 (en) * | 2010-06-17 | 2011-12-22 | Novartis Ag | Biphenyl substituted 1,3-dihydro-benzoimidazol-2-ylideneamine derivatives |
| JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｇｐｒ１１９レセプターのモジュレーターおよびそれに関連する障害の処置 |
| US9834518B2 (en) | 2011-05-04 | 2017-12-05 | Ariad Pharmaceuticals, Inc. | Compounds for inhibiting cell proliferation in EGFR-driven cancers |
| US9061028B2 (en) | 2012-02-15 | 2015-06-23 | Natco Pharma Limited | Process for the preparation of Nilotinib |
| JP6469567B2 (ja) | 2012-05-05 | 2019-02-13 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Ｅｇｆｒ発動性がんの細胞増殖阻害用化合物 |
| KR101469127B1 (ko) * | 2013-03-11 | 2014-12-04 | 한양대학교 에리카산학협력단 | 신규 벤즈이미다졸 유도체, 이의 이성질체 또는 이의 약학적으로 허용 가능한 염, 및 이를 포함하는 약학 조성물 |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
| WO2016014542A1 (en) * | 2014-07-21 | 2016-01-28 | Dana-Farber Cancer Institute, Inc. | Imidazolyl kinase inhibitors and uses thereof |
| KR101850282B1 (ko) * | 2014-11-26 | 2018-05-31 | 한국과학기술연구원 | 단백질 키나아제 저해제로 유용한 헤테로아릴아민 유도체 |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| DK3310760T3 (da) | 2015-06-22 | 2022-10-24 | Arena Pharm Inc | Krystallinsk L-argininsalt af (R)-2-(7-(4-cyclopentyl-3-(trifluormethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)eddikesyre til anvendelse ved S1P1-receptor-associerede lidelser |
| US9890163B2 (en) | 2015-10-15 | 2018-02-13 | Princeton Drug Discovery Inc | Inhibitors of protein kinases |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| KR101840674B1 (ko) * | 2017-02-20 | 2018-03-21 | 한양대학교 에리카산학협력단 | Jnk 저해 활성을 갖는 신규한 벤즈이미다졸 유도체 및 이의 용도 |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| KR20230084416A (ko) * | 2021-12-03 | 2023-06-13 | 연세대학교 산학협력단 | Wnk3 억제제를 유효성분으로 포함하는 면역관문 억제용 조성물 |
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| WO2001060816A1 (en) * | 2000-02-17 | 2001-08-23 | Amgen Inc. | Kinase inhibitors |
| RU2222536C2 (ru) * | 1998-11-17 | 2004-01-27 | Кумиай Кемикал Индастри Ко., Лтд. | Производные пиримидинилбензимидазола и триазинилбензимидазола и содержащий их фунгицид для сельского хозяйства/садоводства |
| EP1389617A1 (en) * | 2001-04-27 | 2004-02-18 | Zenyaku Kogyo Kabushiki Kaisha | Heterocyclic compound and antitumor agent containing the same as active ingredient |
-
2006
- 2006-06-30 AU AU2006265840A patent/AU2006265840B2/en not_active Expired - Fee Related
- 2006-06-30 CN CN2006800242273A patent/CN101213192B/zh not_active Expired - Fee Related
- 2006-06-30 EP EP06774386A patent/EP1899329B1/en not_active Not-in-force
- 2006-06-30 WO PCT/US2006/025706 patent/WO2007005673A1/en not_active Ceased
- 2006-06-30 CA CA002614148A patent/CA2614148A1/en not_active Abandoned
- 2006-06-30 RU RU2008103143/04A patent/RU2386630C2/ru not_active IP Right Cessation
- 2006-06-30 PL PL06774386T patent/PL1899329T3/pl unknown
- 2006-06-30 AT AT06774386T patent/ATE527253T1/de active
- 2006-06-30 MX MX2007016066A patent/MX2007016066A/es not_active Application Discontinuation
- 2006-06-30 JP JP2008519635A patent/JP5054004B2/ja not_active Expired - Fee Related
- 2006-06-30 PT PT06774386T patent/PT1899329E/pt unknown
- 2006-06-30 KR KR1020077030728A patent/KR20080015475A/ko not_active Abandoned
- 2006-06-30 US US11/915,148 patent/US8426404B2/en not_active Expired - Fee Related
- 2006-06-30 ES ES06774386T patent/ES2375151T3/es active Active
- 2006-06-30 BR BRPI0613501-3A patent/BRPI0613501A2/pt not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2222536C2 (ru) * | 1998-11-17 | 2004-01-27 | Кумиай Кемикал Индастри Ко., Лтд. | Производные пиримидинилбензимидазола и триазинилбензимидазола и содержащий их фунгицид для сельского хозяйства/садоводства |
| WO2001060816A1 (en) * | 2000-02-17 | 2001-08-23 | Amgen Inc. | Kinase inhibitors |
| EP1389617A1 (en) * | 2001-04-27 | 2004-02-18 | Zenyaku Kogyo Kabushiki Kaisha | Heterocyclic compound and antitumor agent containing the same as active ingredient |
Also Published As
| Publication number | Publication date |
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| AU2006265840A1 (en) | 2007-01-11 |
| WO2007005673A1 (en) | 2007-01-11 |
| CN101213192B (zh) | 2012-06-06 |
| CN101213192A (zh) | 2008-07-02 |
| MX2007016066A (es) | 2008-03-10 |
| US20080255112A1 (en) | 2008-10-16 |
| EP1899329A1 (en) | 2008-03-19 |
| RU2008103143A (ru) | 2009-08-10 |
| PL1899329T3 (pl) | 2012-03-30 |
| EP1899329B1 (en) | 2011-10-05 |
| CA2614148A1 (en) | 2007-01-11 |
| ATE527253T1 (de) | 2011-10-15 |
| ES2375151T3 (es) | 2012-02-27 |
| PT1899329E (pt) | 2012-01-13 |
| JP5054004B2 (ja) | 2012-10-24 |
| KR20080015475A (ko) | 2008-02-19 |
| AU2006265840B2 (en) | 2010-02-11 |
| US8426404B2 (en) | 2013-04-23 |
| BRPI0613501A2 (pt) | 2011-01-11 |
| JP2009500348A (ja) | 2009-01-08 |
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