CA2882270A1 - Vegfr3 inhibitors - Google Patents
Vegfr3 inhibitors Download PDFInfo
- Publication number
- CA2882270A1 CA2882270A1 CA2882270A CA2882270A CA2882270A1 CA 2882270 A1 CA2882270 A1 CA 2882270A1 CA 2882270 A CA2882270 A CA 2882270A CA 2882270 A CA2882270 A CA 2882270A CA 2882270 A1 CA2882270 A1 CA 2882270A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- alkyl
- methyl
- compound
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229940127432 VEGFR3 Inhibitors Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 380
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 45
- 201000011510 cancer Diseases 0.000 claims abstract description 39
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 230000005764 inhibitory process Effects 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 230000001668 ameliorated effect Effects 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 8
- 239000008177 pharmaceutical agent Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 230
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 165
- 125000000217 alkyl group Chemical group 0.000 claims description 117
- -1 cyclopropylidene, cyclobutylidene, cyclopentylidene Chemical group 0.000 claims description 110
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
- 229940002612 prodrug Drugs 0.000 claims description 59
- 239000000651 prodrug Substances 0.000 claims description 59
- 239000012453 solvate Substances 0.000 claims description 57
- 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 238000001727 in vivo Methods 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
- 230000000259 anti-tumor effect Effects 0.000 claims description 5
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 208000026037 malignant tumor of neck Diseases 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims 3
- 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 2
- 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 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
- 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 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
- KOVWPXOOIFPKTR-UHFFFAOYSA-N 2-[2-[2-[2-[4-(3-aminooxetan-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=C1C1(N)COC1 KOVWPXOOIFPKTR-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
- KTPMPJGZQKHEHW-UHFFFAOYSA-N 2-[2-[2-[2-[4-(piperazine-1-carbonyl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1CCC1=NC(NC=2C=CC(=CC=2)C(=O)N2CCNCC2)=NC=C1C(F)(F)F KTPMPJGZQKHEHW-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
- NLSFWYVKGBOHMI-UHFFFAOYSA-N 2-[2-[2-[2-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]acetamide Chemical compound C1CN(C)CCC1N1N=CC(NC=2N=C(CCC=3C(=CC=CC=3)CC(N)=O)C(=CN=2)C(F)(F)F)=C1 NLSFWYVKGBOHMI-UHFFFAOYSA-N 0.000 claims 2
- 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 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
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- 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
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- 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 2
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Classifications
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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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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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/02—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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D405/02—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 containing two hetero rings
- C07D405/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2882270A1 true CA2882270A1 (en) | 2014-02-20 |
Family
ID=50101125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2882270A Abandoned CA2882270A1 (en) | 2012-08-17 | 2013-08-16 | Vegfr3 inhibitors |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US9266864B2 (enExample) |
| EP (1) | EP2885292A4 (enExample) |
| JP (1) | JP2015524825A (enExample) |
| CN (2) | CN104837835A (enExample) |
| AU (1) | AU2013302319A1 (enExample) |
| CA (1) | CA2882270A1 (enExample) |
| HK (1) | HK1209104A1 (enExample) |
| WO (1) | WO2014026242A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015123722A1 (en) * | 2014-02-19 | 2015-08-27 | Bionomics Limited | Inhibitors |
| CN112972492B (zh) | 2015-12-16 | 2024-11-08 | 沃尔特及伊莱萨霍尔医学研究院 | Nk细胞中对细胞因子诱导的sh2蛋白的抑制 |
| EP4026849A1 (en) * | 2016-09-26 | 2022-07-13 | Ensemble Group Holdings | Methods of assessing and treating cancer in subjects having dysregulated lymphatic systems using a combination of vegfr-3 and pd-1 or pd-l1 inhibitors |
| US11279763B2 (en) | 2016-10-27 | 2022-03-22 | The Regents Of The University Of California | Integrin alpha 9 blockade suppresses lymphatic valve formation and promotes transplant survival |
| CA3048376A1 (en) | 2016-12-27 | 2018-07-05 | 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 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE50212771D1 (de) * | 2001-10-17 | 2008-10-23 | Boehringer Ingelheim Pharma | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
| TW200922590A (en) * | 2007-09-10 | 2009-06-01 | Curis Inc | VEGFR inhibitors containing a zinc binding moiety |
| EP2367826A4 (en) | 2008-11-06 | 2012-07-04 | Astrazeneca Ab | MODULATORS OF THE PROTEIN -AMYLOID |
| UA103351C2 (uk) * | 2008-12-05 | 2013-10-10 | Ебботт Леборетріз | ПОХІДНІ ТІЄНО[3,2-c]ПІРИДИНУ ЯК ІНГІБІТОРИ КІНАЗ ДЛЯ ЗАСТОСУВАННЯ В ЛІКУВАННІ РАКУ |
| WO2010111406A2 (en) | 2009-03-24 | 2010-09-30 | Myriad Pharmaceuticals, Inc. | Compounds and therapeutic uses thereof |
| WO2010130757A1 (en) * | 2009-05-14 | 2010-11-18 | 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 |
| WO2012110774A1 (en) | 2011-02-17 | 2012-08-23 | Cancer Therapeutics Crc Pty Limited | Selective fak inhibitors |
| DK2675793T3 (en) * | 2011-02-17 | 2018-11-12 | Cancer Therapeutics Crc Pty Ltd | FAK INHIBITORS |
| KR101682417B1 (ko) | 2011-02-25 | 2016-12-06 | 주식회사유한양행 | 다이아미노피리미딘 유도체 및 그의 제조방법 |
| EA027982B1 (ru) | 2012-07-17 | 2017-09-29 | Санофи | Применение ингибиторов vegfr-3 для лечения гепатоклеточной карциномы |
| WO2014027199A1 (en) * | 2012-08-14 | 2014-02-20 | Cancer Therapeutics Crc Pty Ltd | Fak and flt3 inhibitors |
| US9238644B2 (en) * | 2012-08-17 | 2016-01-19 | 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 |
-
2013
- 2013-08-16 JP JP2015526835A patent/JP2015524825A/ja active Pending
- 2013-08-16 US US13/968,932 patent/US9266864B2/en not_active Expired - Fee Related
- 2013-08-16 CA CA2882270A patent/CA2882270A1/en not_active Abandoned
- 2013-08-16 WO PCT/AU2013/000912 patent/WO2014026242A1/en not_active Ceased
- 2013-08-16 US US14/422,084 patent/US20150225377A1/en not_active Abandoned
- 2013-08-16 HK HK15109686.3A patent/HK1209104A1/xx unknown
- 2013-08-16 AU AU2013302319A patent/AU2013302319A1/en not_active Abandoned
- 2013-08-16 EP EP13829826.0A patent/EP2885292A4/en not_active Withdrawn
- 2013-08-16 CN CN201380052157.2A patent/CN104837835A/zh active Pending
- 2013-08-16 CN CN201710144110.9A patent/CN106986832A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015524825A (ja) | 2015-08-27 |
| EP2885292A4 (en) | 2015-07-01 |
| US9266864B2 (en) | 2016-02-23 |
| CN104837835A (zh) | 2015-08-12 |
| CN106986832A (zh) | 2017-07-28 |
| US20150225377A1 (en) | 2015-08-13 |
| US20140080798A1 (en) | 2014-03-20 |
| WO2014026242A1 (en) | 2014-02-20 |
| HK1209104A1 (en) | 2016-03-24 |
| AU2013302319A1 (en) | 2015-02-26 |
| EP2885292A1 (en) | 2015-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180816 |