JP2015524825A5 - - Google Patents
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- JP2015524825A5 JP2015524825A5 JP2015526835A JP2015526835A JP2015524825A5 JP 2015524825 A5 JP2015524825 A5 JP 2015524825A5 JP 2015526835 A JP2015526835 A JP 2015526835A JP 2015526835 A JP2015526835 A JP 2015526835A JP 2015524825 A5 JP2015524825 A5 JP 2015524825A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- methyl
- ethyl
- acetamide
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 60
- 150000001875 compounds Chemical class 0.000 claims 59
- 229910052799 carbon Inorganic materials 0.000 claims 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 29
- 125000001424 substituent group Chemical group 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 21
- 239000012453 solvate Substances 0.000 claims 21
- 239000000651 prodrug Substances 0.000 claims 20
- 229940002612 prodrug Drugs 0.000 claims 20
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 18
- -1 cyclopropylidene, cyclobutylidene, cyclopentylidene Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 4
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- XDMLBYJYFBWPEM-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-[(6-piperidin-4-ylpyridin-3-yl)amino]pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC(C=N1)=CC=C1C1CCNCC1 XDMLBYJYFBWPEM-UHFFFAOYSA-N 0.000 claims 3
- 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- ZCSLTAPRCWBMTF-UHFFFAOYSA-N 2-[2-[2-[2-(4-piperazin-1-ylanilino)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1CCC1=CC=NC(NC=2C=CC(=CC=2)N2CCNCC2)=N1 ZCSLTAPRCWBMTF-UHFFFAOYSA-N 0.000 claims 2
- PSDHXBOJIOXUEW-UHFFFAOYSA-N 2-[2-[2-[2-(4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]-5-(trifluoromethyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC(C(F)(F)F)=CC=C1CCC1=NC(NC=2C=CC(=CC=2)C2CCNCC2)=NC=C1C(F)(F)F PSDHXBOJIOXUEW-UHFFFAOYSA-N 0.000 claims 2
- OXNCQFJFRZBEPY-UHFFFAOYSA-N 2-[2-[2-[2-(4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]-6-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC=C(C(F)(F)F)C(CC(=O)N)=C1CCC1=NC(NC=2C=CC(=CC=2)C2CCNCC2)=NC=C1C(F)(F)F OXNCQFJFRZBEPY-UHFFFAOYSA-N 0.000 claims 2
- AFIKVRLFAWOLRU-UHFFFAOYSA-N 2-[2-[2-[2-[(1-piperidin-4-ylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1CCC1=NC(NC2=CN(N=C2)C2CCNCC2)=NC=C1C(F)(F)F AFIKVRLFAWOLRU-UHFFFAOYSA-N 0.000 claims 2
- FPXDSJAROCABJE-UHFFFAOYSA-N 2-[2-[2-[2-[3-(1-acetamidoethyl)anilino]-5-chloropyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound CC(=O)NC(C)C1=CC=CC(NC=2N=C(CCC=3C(=CC=CC=3)CC(N)=O)C(Cl)=CN=2)=C1 FPXDSJAROCABJE-UHFFFAOYSA-N 0.000 claims 2
- GFQVYPFDWXATIW-UHFFFAOYSA-N 2-[2-[2-[2-[3-(1-aminoethyl)anilino]-5-chloropyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound CC(N)C1=CC=CC(NC=2N=C(CCC=3C(=CC=CC=3)CC(N)=O)C(Cl)=CN=2)=C1 GFQVYPFDWXATIW-UHFFFAOYSA-N 0.000 claims 2
- WTAYXQZUKKCIPJ-UHFFFAOYSA-N 2-[2-[2-[2-[3-fluoro-4-(1-methylpiperidin-4-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1CN(C)CCC1C(C(=C1)F)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 WTAYXQZUKKCIPJ-UHFFFAOYSA-N 0.000 claims 2
- OWXKLULULDRQDQ-UHFFFAOYSA-N 2-[2-[2-[2-[3-methyl-4-(1-methylpiperidin-4-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1CN(C)CCC1C(C(=C1)C)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 OWXKLULULDRQDQ-UHFFFAOYSA-N 0.000 claims 2
- QRWTZHKLKHTWCL-UHFFFAOYSA-N 2-[2-[2-[2-[4-(1-aminoethyl)anilino]-5-chloropyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1=CC(C(N)C)=CC=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 QRWTZHKLKHTWCL-UHFFFAOYSA-N 0.000 claims 2
- WOFLAEARBIFOJT-UHFFFAOYSA-N 2-[2-[2-[2-[4-(1-aminoethyl)anilino]-5-methylpyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1=CC(C(N)C)=CC=C1NC1=NC=C(C)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 WOFLAEARBIFOJT-UHFFFAOYSA-N 0.000 claims 2
- DIKWZDVSRMNGGE-UHFFFAOYSA-N 2-[2-[2-[2-[4-(1-methylpiperidin-4-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]-4-(trifluoromethyl)phenyl]acetamide Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=C(C=2)C(F)(F)F)CC(N)=O)=N1 DIKWZDVSRMNGGE-UHFFFAOYSA-N 0.000 claims 2
- PYVAEEAGWMSKHD-UHFFFAOYSA-N 2-[2-[2-[2-[4-(aminomethyl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1=CC(CN)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 PYVAEEAGWMSKHD-UHFFFAOYSA-N 0.000 claims 2
- ACYSNXBWWJMVHP-UHFFFAOYSA-N 2-[2-[2-[2-[4-(aminomethyl)anilino]-5-methylpyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC1=CC=C(CN)C=C1 ACYSNXBWWJMVHP-UHFFFAOYSA-N 0.000 claims 2
- HDFCPVIDDQRCPP-UHFFFAOYSA-N 2-[2-[2-[2-[4-(azetidin-3-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1CCC1=NC(NC=2C=CC(=CC=2)C2CNC2)=NC=C1C(F)(F)F HDFCPVIDDQRCPP-UHFFFAOYSA-N 0.000 claims 2
- XFPIWVJDMUZQLR-UHFFFAOYSA-N 2-[2-[2-[2-[4-(azetidin-3-yl)anilino]-5-methylpyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC(C=C1)=CC=C1C1CNC1 XFPIWVJDMUZQLR-UHFFFAOYSA-N 0.000 claims 2
- FQSILTSTNIHYSF-UHFFFAOYSA-N 2-[2-[2-[2-[4-[(2-hydroxyethylamino)methyl]anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1CCC1=NC(NC=2C=CC(CNCCO)=CC=2)=NC=C1C(F)(F)F FQSILTSTNIHYSF-UHFFFAOYSA-N 0.000 claims 2
- GYCYXSIVTCRVJB-UHFFFAOYSA-N 2-[2-[2-[2-[[6-(1-aminoethyl)pyridin-3-yl]amino]-5-chloropyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1=NC(C(N)C)=CC=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 GYCYXSIVTCRVJB-UHFFFAOYSA-N 0.000 claims 2
- HLXQYTKTHHXVSD-UHFFFAOYSA-N 2-[2-[2-[2-[[6-(1-methylpiperidin-4-yl)pyridin-3-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1CN(C)CCC1C(N=C1)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 HLXQYTKTHHXVSD-UHFFFAOYSA-N 0.000 claims 2
- RZCJZEVHDUNONV-UHFFFAOYSA-N 2-[2-[2-[5-methoxy-2-(4-piperidin-4-ylanilino)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(OC)=CN=C1NC(C=C1)=CC=C1C1CCNCC1 RZCJZEVHDUNONV-UHFFFAOYSA-N 0.000 claims 2
- BTPKHVRHWSFQTR-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-(4-piperazin-1-ylanilino)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC(C=C1)=CC=C1N1CCNCC1 BTPKHVRHWSFQTR-UHFFFAOYSA-N 0.000 claims 2
- SFXQZDVLZUPAFD-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-(4-piperidin-4-ylanilino)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC(C=C1)=CC=C1C1CCNCC1 SFXQZDVLZUPAFD-UHFFFAOYSA-N 0.000 claims 2
- OUMMZLTWRFRHRJ-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-(4-piperidin-4-yloxyanilino)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC(C=C1)=CC=C1OC1CCNCC1 OUMMZLTWRFRHRJ-UHFFFAOYSA-N 0.000 claims 2
- QUWXNYXWWFLRCA-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-(pyridin-3-ylamino)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC1=CC=CN=C1 QUWXNYXWWFLRCA-UHFFFAOYSA-N 0.000 claims 2
- 230000001668 ameliorated effect Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- BQEJKVORCZBMIZ-UHFFFAOYSA-N methyl n-[1-[4-[[4-[2-[2-(2-amino-2-oxoethyl)phenyl]ethyl]-5-methylpyrimidin-2-yl]amino]phenyl]cyclobutyl]carbamate Chemical compound C=1C=C(NC=2N=C(CCC=3C(=CC=CC=3)CC(N)=O)C(C)=CN=2)C=CC=1C1(NC(=O)OC)CCC1 BQEJKVORCZBMIZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- VUSNIIBMNQLWAI-UHFFFAOYSA-N 2-[2-[2-[2-(3-fluoro-4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1CCC1=NC(NC=2C=C(F)C(C3CCNCC3)=CC=2)=NC=C1C(F)(F)F VUSNIIBMNQLWAI-UHFFFAOYSA-N 0.000 claims 1
- YEJYWOCEMFYOCT-UHFFFAOYSA-N 2-[2-[2-[2-(3-methyl-4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C=1C=C(C2CCNCC2)C(C)=CC=1NC(N=1)=NC=C(C(F)(F)F)C=1CCC1=CC=CC=C1CC(N)=O YEJYWOCEMFYOCT-UHFFFAOYSA-N 0.000 claims 1
- MEQLFZOVUZJWAI-UHFFFAOYSA-N 2-[2-[2-[2-[(6-piperidin-4-ylpyridin-3-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1CCC1=NC(NC=2C=NC(=CC=2)C2CCNCC2)=NC=C1C(F)(F)F MEQLFZOVUZJWAI-UHFFFAOYSA-N 0.000 claims 1
- DOMYHOISEZLNTA-UHFFFAOYSA-N 2-[2-[2-[2-[[1-(azetidin-3-yl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC(=C1)C=NN1C1CNC1 DOMYHOISEZLNTA-UHFFFAOYSA-N 0.000 claims 1
- JJFRVCDWUNLPOP-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound N1=C(CCC=2C(=CC=CC=2)CC(N)=O)C(C)=CN=C1NC(=C1)C=NN1C1CCNCC1 JJFRVCDWUNLPOP-UHFFFAOYSA-N 0.000 claims 1
- GDVBBAJTPKHOET-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-[[6-(1-methylpiperidin-4-yl)pyridin-3-yl]amino]pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1CN(C)CCC1C(N=C1)=CC=C1NC1=NC=C(C)C(CCC=2C(=CC=CC=2)CC(N)=O)=N1 GDVBBAJTPKHOET-UHFFFAOYSA-N 0.000 claims 1
- WFRJERWIXQUGFT-UHFFFAOYSA-N 2-[4-methyl-2-[2-[2-(4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound CC1=CC=C(CC(N)=O)C(CCC=2C(=CN=C(NC=3C=CC(=CC=3)C3CCNCC3)N=2)C(F)(F)F)=C1 WFRJERWIXQUGFT-UHFFFAOYSA-N 0.000 claims 1
- DTXYSXSROLLGII-UHFFFAOYSA-N 2-[5-fluoro-2-[2-[2-(4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC(F)=CC=C1CCC1=NC(NC=2C=CC(=CC=2)C2CCNCC2)=NC=C1C(F)(F)F DTXYSXSROLLGII-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 238000011275 oncology therapy Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 CC(CC*)=C(*)C=NC(N*)=*=C Chemical compound CC(CC*)=C(*)C=NC(N*)=*=C 0.000 description 95
- KAUSQWLEXMNEAQ-UHFFFAOYSA-N C1C2=CC3=CC2=CC13 Chemical compound C1C2=CC3=CC2=CC13 KAUSQWLEXMNEAQ-UHFFFAOYSA-N 0.000 description 1
- ODYFWQCVWHJROZ-MWYAZZEHSA-N CC(C(CCC1)CCCC1c(cc1)ccc1C(c1ncc(C(F)(F)F)c(CC/C(/C(CC(NC)=O)=C)=C/C=C)n1)=C)=O Chemical compound CC(C(CCC1)CCCC1c(cc1)ccc1C(c1ncc(C(F)(F)F)c(CC/C(/C(CC(NC)=O)=C)=C/C=C)n1)=C)=O ODYFWQCVWHJROZ-MWYAZZEHSA-N 0.000 description 1
- WHKWMTXTYKVFLK-UHFFFAOYSA-N CC(C)N1CCNCC1 Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 description 1
- ZICRALLMHKILDG-UHFFFAOYSA-N CC(C)c1ccn[nH]1 Chemical compound CC(C)c1ccn[nH]1 ZICRALLMHKILDG-UHFFFAOYSA-N 0.000 description 1
- UQUHQKVINDTPNE-UHFFFAOYSA-N CC(CC1)CCN1N Chemical compound CC(CC1)CCN1N UQUHQKVINDTPNE-UHFFFAOYSA-N 0.000 description 1
- CYTQZWGBGWLGCL-UHFFFAOYSA-N CC(CCc1c2)Cc1ccc2[IH]C(NC)=N Chemical compound CC(CCc1c2)Cc1ccc2[IH]C(NC)=N CYTQZWGBGWLGCL-UHFFFAOYSA-N 0.000 description 1
- VHHKBSDREZULMD-UHFFFAOYSA-N CC(c1cnc(Nc2ccc(C3CNCCC3)cc2)nc1CCc1ccccc1CC(N)=O)(F)F Chemical compound CC(c1cnc(Nc2ccc(C3CNCCC3)cc2)nc1CCc1ccccc1CC(N)=O)(F)F VHHKBSDREZULMD-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N CC1CCNCC1 Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- XOQMBPKLVSRVDA-QDOSSMDNSA-N CCC(CC(C)=C)c1ccc(C(C)/C(/N=C/CCC2C(CC(C)N)=CC=CC2)=C/C=C/C(F)(F)F)cc1 Chemical compound CCC(CC(C)=C)c1ccc(C(C)/C(/N=C/CCC2C(CC(C)N)=CC=CC2)=C/C=C/C(F)(F)F)cc1 XOQMBPKLVSRVDA-QDOSSMDNSA-N 0.000 description 1
- BOQZDTMVKUJPOF-UHFFFAOYSA-N CCC(CCCCc(cc1)ccc1Nc1ncc(C(F)F)c(CCc2ccccc2CC(NC)=O)n1)N(C)C Chemical compound CCC(CCCCc(cc1)ccc1Nc1ncc(C(F)F)c(CCc2ccccc2CC(NC)=O)n1)N(C)C BOQZDTMVKUJPOF-UHFFFAOYSA-N 0.000 description 1
- IEGNEFIWHOOQEB-ONEGZZNKSA-N CCC(N(CC1)CCN1/C=C/N)=O Chemical compound CCC(N(CC1)CCN1/C=C/N)=O IEGNEFIWHOOQEB-ONEGZZNKSA-N 0.000 description 1
- PONFAIBVDWYWNT-GXDHUFHOSA-N CCC/C=N/C(NC)NC1=CCCC=C1 Chemical compound CCC/C=N/C(NC)NC1=CCCC=C1 PONFAIBVDWYWNT-GXDHUFHOSA-N 0.000 description 1
- TXIOGJHPPVXTOY-UHFFFAOYSA-N CCN1CCN(C)CC1 Chemical compound CCN1CCN(C)CC1 TXIOGJHPPVXTOY-UHFFFAOYSA-N 0.000 description 1
- IHNXHUNMFYXQCG-UHFFFAOYSA-N CCc1c[nH]nc1 Chemical compound CCc1c[nH]nc1 IHNXHUNMFYXQCG-UHFFFAOYSA-N 0.000 description 1
- QNLVTCHFUUSVEQ-UHFFFAOYSA-N CN(CC1)CCC1OS Chemical compound CN(CC1)CCC1OS QNLVTCHFUUSVEQ-UHFFFAOYSA-N 0.000 description 1
- HRMBSHRYMFIUMV-UHFFFAOYSA-N CN(CC1)CCC1OSC Chemical compound CN(CC1)CCC1OSC HRMBSHRYMFIUMV-UHFFFAOYSA-N 0.000 description 1
- VMSSMRFBHIVZRI-UHFFFAOYSA-N CN(CC1)CCN1c(cc1)ccc1Nc1ncc(C(F)(F)F)c(CCc2c(CC(N)O)cccc2)n1 Chemical compound CN(CC1)CCN1c(cc1)ccc1Nc1ncc(C(F)(F)F)c(CCc2c(CC(N)O)cccc2)n1 VMSSMRFBHIVZRI-UHFFFAOYSA-N 0.000 description 1
- DQGMDBXTJWSKSB-UHFFFAOYSA-N CN(CC1)CCN1c1cccc(Nc2nc(CCc3ccccc3)c(C(F)(F)F)cn2)c1 Chemical compound CN(CC1)CCN1c1cccc(Nc2nc(CCc3ccccc3)c(C(F)(F)F)cn2)c1 DQGMDBXTJWSKSB-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N CN1CCN(C)CC1 Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- KLFSEANDDJVDJZ-UHFFFAOYSA-N NC(Cc1c(CCc2c(C(F)(F)F)cnc(Nc3cc(CCNC4)c4cc3)n2)cccc1)=O Chemical compound NC(Cc1c(CCc2c(C(F)(F)F)cnc(Nc3cc(CCNC4)c4cc3)n2)cccc1)=O KLFSEANDDJVDJZ-UHFFFAOYSA-N 0.000 description 1
- DCXNVUSMVYIZCV-UHFFFAOYSA-N NC(Cc1c(CCc2c(C(F)(F)F)cnc(Nc3ccc(C4CCNCC4)cc3)n2)c(F)ccc1)=O Chemical compound NC(Cc1c(CCc2c(C(F)(F)F)cnc(Nc3ccc(C4CCNCC4)cc3)n2)c(F)ccc1)=O DCXNVUSMVYIZCV-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N OC1CCNCC1 Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261684254P | 2012-08-17 | 2012-08-17 | |
| US61/684,254 | 2012-08-17 | ||
| PCT/AU2013/000912 WO2014026242A1 (en) | 2012-08-17 | 2013-08-16 | Vegfr3 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015524825A JP2015524825A (ja) | 2015-08-27 |
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| EP3827838B1 (en) | 2015-12-16 | 2023-06-07 | The Walter and Eliza Hall Institute of Medical Research | Inhibition of cytokine-induced sh2 protein in nk cells |
| WO2018058125A1 (en) | 2016-09-26 | 2018-03-29 | Ensemble Group Holdings | Methods of assessing and treating cancer in subjects having dysregulated lymphatic systems |
| WO2018081436A1 (en) * | 2016-10-27 | 2018-05-03 | The Regents Of The University Of California | Integrin alpha 9 blockade suppresses lymphatic valve formation and promotes transplant survival |
| US10954216B2 (en) | 2016-12-27 | 2021-03-23 | Riken | BMP-signal-inhibiting compound |
| CN109942616A (zh) * | 2019-04-18 | 2019-06-28 | 广东工业大学 | 一种含炔基的芳基酰胺类衍生物及其制备方法和应用 |
| CN114853740B (zh) * | 2021-02-03 | 2023-08-01 | 药雅科技(上海)有限公司 | 炔类嘧啶化合物作为fgfr抑制剂的制备方法和用途 |
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| ES2314106T3 (es) | 2001-10-17 | 2009-03-16 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | Derivados de pirimidina, agentes farmaceuticos que contiene dichos compuestos, uso y metodo para su obtencion. |
| TW200922590A (en) * | 2007-09-10 | 2009-06-01 | Curis Inc | VEGFR inhibitors containing a zinc binding moiety |
| CN102272133A (zh) | 2008-11-06 | 2011-12-07 | 阿斯利康(瑞典)有限公司 | 淀粉样β的调节剂 |
| KR101639642B1 (ko) * | 2008-12-05 | 2016-07-14 | 애브비 바하마스 리미티드 | 암 치료에 사용하기 위한 키나제 억제제로서의 티에노［3,2-ｃ］피리딘 유도체 |
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| EP2429520A1 (en) * | 2009-05-14 | 2012-03-21 | Boehringer Ingelheim International GmbH | New combination therapy in treatment of oncological and fibrotic diseases |
| DE102010034699A1 (de) * | 2010-08-18 | 2012-02-23 | Merck Patent Gmbh | Pyrimidinderivate |
| JP6185839B2 (ja) * | 2010-09-14 | 2017-08-23 | ノバルティス アーゲー | Ｂｒａｆ阻害薬とｖｅｇｆ阻害薬との組み合わせ |
| ES2691673T3 (es) * | 2011-02-17 | 2018-11-28 | Cancer Therapeutics Crc Pty Limited | Inhibidores de Fak |
| JP5937112B2 (ja) | 2011-02-17 | 2016-06-22 | カンサー・セラピューティクス・シーアールシー・プロプライエタリー・リミテッドＣａｎｃｅｒ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｃｒｃ Ｐｔｙ Ｌｉｍｉｔｅｄ | 選択的ｆａｋ阻害剤 |
| KR101682417B1 (ko) | 2011-02-25 | 2016-12-06 | 주식회사유한양행 | 다이아미노피리미딘 유도체 및 그의 제조방법 |
| EP2874625B1 (en) | 2012-07-17 | 2017-05-17 | Sanofi | Use of vegfr-3 inhibitors for treating hepatocellular carcinoma |
| WO2014027199A1 (en) * | 2012-08-14 | 2014-02-20 | Cancer Therapeutics Crc Pty Ltd | Fak and flt3 inhibitors |
| HK1209105A1 (en) * | 2012-08-17 | 2016-03-24 | Cancer Therapeutics Crc Pty Limited | Vegfr3 inhibitors |
| CN103113355B (zh) | 2013-02-27 | 2014-08-13 | 无锡爱内特生物科技有限公司 | 一种Bcr/Abl酪氨酸激酶抑制剂及其制备方法和在治疗慢性粒细胞白血病中的应用 |
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