CA2666112A1 - Pyrrolydine derivatives as iap inhibitors - Google Patents
Pyrrolydine derivatives as iap inhibitors Download PDFInfo
- Publication number
- CA2666112A1 CA2666112A1 CA002666112A CA2666112A CA2666112A1 CA 2666112 A1 CA2666112 A1 CA 2666112A1 CA 002666112 A CA002666112 A CA 002666112A CA 2666112 A CA2666112 A CA 2666112A CA 2666112 A1 CA2666112 A1 CA 2666112A1
- Authority
- CA
- Canada
- Prior art keywords
- methylamino
- pyrrolidin
- cyclohexyl
- ethyl
- propionamide
- 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
- 239000003112 inhibitor Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 229940080818 propionamide Drugs 0.000 claims description 124
- -1 amino, amino Chemical group 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 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 description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- TXHPORRYUKITDP-UHFFFAOYSA-N sulfamoylsulfamic acid Chemical compound NS(=O)(=O)NS(O)(=O)=O TXHPORRYUKITDP-UHFFFAOYSA-N 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 230000004663 cell proliferation Effects 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- LSMBOQAQZPPBCL-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(1h-indol-3-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C3=CC=CC=C3NC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 LSMBOQAQZPPBCL-UHFFFAOYSA-N 0.000 claims 2
- XAYZUCXGUHTJRQ-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(2-isoquinolin-4-ylpyridin-4-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)C=2C3=CC=CC=C3C=NC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 XAYZUCXGUHTJRQ-UHFFFAOYSA-N 0.000 claims 2
- ZBNJXFRWAFDUEP-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(6-fluoroindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC(F)=CC=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ZBNJXFRWAFDUEP-UHFFFAOYSA-N 0.000 claims 2
- XSBOCMDIRLWEBS-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(2,3-dihydroindol-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 XSBOCMDIRLWEBS-UHFFFAOYSA-N 0.000 claims 2
- FVAHQZJOBROOQE-UHFFFAOYSA-N 2-(methylamino)-n-[3-methyl-1-[2-[2-(3-methylindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-1-oxobutan-2-yl]propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC=NC(N2C3=CC=CC=C3C(C)=C2)=C1 FVAHQZJOBROOQE-UHFFFAOYSA-N 0.000 claims 1
- VXFMMEINZOLOJN-UHFFFAOYSA-N 3-[5-[1-[2-cyclohexyl-2-[2-(methylamino)propanoylamino]acetyl]pyrrolidin-2-yl]pyridin-3-yl]-n,n-dimethylindole-1-carboxamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C3=CC=CC=C3N(C(=O)N(C)C)C=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 VXFMMEINZOLOJN-UHFFFAOYSA-N 0.000 claims 1
- JBCBEGAXTUBSQQ-UHFFFAOYSA-N 3-[6-[1-[2-cyclohexyl-2-[2-(methylamino)propanoylamino]acetyl]pyrrolidin-2-yl]-2-methylpyrimidin-4-yl]-n,n-dimethylindole-1-carboxamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C3=CC=CC=C3N(C(=O)N(C)C)C=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JBCBEGAXTUBSQQ-UHFFFAOYSA-N 0.000 claims 1
- NIXTXVUBGUOWBD-UHFFFAOYSA-N 3-[6-[1-[2-cyclohexyl-2-[2-(methylamino)propanoylamino]acetyl]pyrrolidin-2-yl]pyrimidin-4-yl]-n,n-dimethylindole-1-carboxamide Chemical compound C1CCC(C=2N=CN=C(C=2)C=2C3=CC=CC=C3N(C(=O)N(C)C)C=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 NIXTXVUBGUOWBD-UHFFFAOYSA-N 0.000 claims 1
- 230000009702 cancer cell proliferation Effects 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- XZRIQMPTARXLFZ-UHFFFAOYSA-N n,n-dimethyl-3-[2-methyl-6-[1-[3-methyl-2-[2-(methylamino)propanoylamino]butanoyl]pyrrolidin-2-yl]pyrimidin-4-yl]indole-1-carboxamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC(C=2C3=CC=CC=C3N(C(=O)N(C)C)C=2)=NC(C)=N1 XZRIQMPTARXLFZ-UHFFFAOYSA-N 0.000 claims 1
- ZYPXULRJFLELOT-UHFFFAOYSA-N n-[1-[2-[2-(5-fluoro-3-methylindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC=NC(N2C3=CC=C(F)C=C3C(C)=C2)=C1 ZYPXULRJFLELOT-UHFFFAOYSA-N 0.000 claims 1
- LCOOPRTUFHOWRJ-UHFFFAOYSA-N n-[1-[2-[2-(6-fluoro-2,3-dihydroindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC=NC(N2C3=CC(F)=CC=C3CC2)=C1 LCOOPRTUFHOWRJ-UHFFFAOYSA-N 0.000 claims 1
- LHTMPBRWDGGNAC-UHFFFAOYSA-N n-[1-[2-[2-(6-fluoroindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC=NC(N2C3=CC(F)=CC=C3C=C2)=C1 LHTMPBRWDGGNAC-UHFFFAOYSA-N 0.000 claims 1
- FUQJVCQDMIKMLZ-UHFFFAOYSA-N n-[1-[2-[2-(benzimidazol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC=NC(N2C3=CC=CC=C3N=C2)=C1 FUQJVCQDMIKMLZ-UHFFFAOYSA-N 0.000 claims 1
- YGNOGFTZPWDFEL-UHFFFAOYSA-N n-[1-[2-[6-(1h-indol-3-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC(C=2C3=CC=CC=C3NC=2)=NC(C)=N1 YGNOGFTZPWDFEL-UHFFFAOYSA-N 0.000 claims 1
- WUIKYTVKOGCDQP-UHFFFAOYSA-N n-[1-[2-[6-(5-fluoro-2,3-dihydroindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC(N2C3=CC=C(F)C=C3CC2)=NC(C)=N1 WUIKYTVKOGCDQP-UHFFFAOYSA-N 0.000 claims 1
- BLGAYYJPBQEXRU-UHFFFAOYSA-N n-[1-[2-[6-(5-fluoro-3-methylindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC(N2C3=CC=C(F)C=C3C(C)=C2)=NC(C)=N1 BLGAYYJPBQEXRU-UHFFFAOYSA-N 0.000 claims 1
- SPTPSCCTWROEGR-UHFFFAOYSA-N n-[1-[2-[6-(5-fluoroindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC(N2C3=CC=C(F)C=C3C=C2)=NC(C)=N1 SPTPSCCTWROEGR-UHFFFAOYSA-N 0.000 claims 1
- NPRSHGBTIXFZER-UHFFFAOYSA-N n-[1-[2-[6-(6-fluoro-2,3-dihydroindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(methylamino)propanamide Chemical compound CNC(C)C(=O)NC(C(C)C)C(=O)N1CCCC1C1=CC(N2C3=CC(F)=CC=C3CC2)=NC(C)=N1 NPRSHGBTIXFZER-UHFFFAOYSA-N 0.000 claims 1
- PABVNKBDVGYEGT-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(1h-indol-2-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2NC3=CC=CC=C3C=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 PABVNKBDVGYEGT-UHFFFAOYSA-N 0.000 claims 1
- YWHNNGLUPMDTAP-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(2-indazol-1-ylpyridin-4-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=CC=C3C=N2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 YWHNNGLUPMDTAP-UHFFFAOYSA-N 0.000 claims 1
- PATOBGOPTMOHLX-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(2-methyl-6-naphthalen-1-ylpyrimidin-4-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C3=CC=CC=C3C=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 PATOBGOPTMOHLX-UHFFFAOYSA-N 0.000 claims 1
- AWLUAEQVEIWWFL-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(2-methyl-6-naphthalen-2-ylpyrimidin-4-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C=C3C=CC=CC3=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 AWLUAEQVEIWWFL-UHFFFAOYSA-N 0.000 claims 1
- QEHNETHUVPZVRJ-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(5-indol-1-ylpyridin-3-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=CC=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 QEHNETHUVPZVRJ-UHFFFAOYSA-N 0.000 claims 1
- DARHYVJGJLVNAH-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(5-naphthalen-1-ylpyridin-3-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C3=CC=CC=C3C=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 DARHYVJGJLVNAH-UHFFFAOYSA-N 0.000 claims 1
- NPQDDJGXKMNGIB-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(5-naphthalen-2-ylpyridin-3-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=C3C=CC=CC3=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 NPQDDJGXKMNGIB-UHFFFAOYSA-N 0.000 claims 1
- AUDVJTRXUBJHLX-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(6-indol-1-yl-2-methylpyrimidin-4-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC=CC=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 AUDVJTRXUBJHLX-UHFFFAOYSA-N 0.000 claims 1
- WJJLAEHIBHIQTF-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(6-indol-1-ylpyrimidin-4-yl)pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CN=C(C=2)N2C3=CC=CC=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 WJJLAEHIBHIQTF-UHFFFAOYSA-N 0.000 claims 1
- LPIHHRFIQAGFRE-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(1,3-dihydroisoindol-2-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2CC3=CC=CC=C3C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 LPIHHRFIQAGFRE-UHFFFAOYSA-N 0.000 claims 1
- ISOGQNDYNHXSCT-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(1h-indol-2-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)C=2NC3=CC=CC=C3C=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ISOGQNDYNHXSCT-UHFFFAOYSA-N 0.000 claims 1
- DQHYGMMNYOMVNI-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(1h-indol-3-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)C=2C3=CC=CC=C3NC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 DQHYGMMNYOMVNI-UHFFFAOYSA-N 0.000 claims 1
- CMBQZNRFGUADIY-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(2,3-dihydroindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 CMBQZNRFGUADIY-UHFFFAOYSA-N 0.000 claims 1
- NZSLQMQFLCDMCP-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(3,4-dihydro-1h-isoquinolin-2-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2CC3=CC=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 NZSLQMQFLCDMCP-UHFFFAOYSA-N 0.000 claims 1
- JCQYIQRGFJBRCC-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(3,4-dihydro-2h-quinolin-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=CC=C3CCC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JCQYIQRGFJBRCC-UHFFFAOYSA-N 0.000 claims 1
- FPHOCWUYBACGGJ-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(3-methylindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=CC=C3C(C)=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 FPHOCWUYBACGGJ-UHFFFAOYSA-N 0.000 claims 1
- RYQZLLHAEKDYPO-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(5-fluoro-2,3-dihydroindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=C(F)C=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 RYQZLLHAEKDYPO-UHFFFAOYSA-N 0.000 claims 1
- WNPUMLYEQOCIHY-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(5-fluoro-3-methylindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=C(F)C=C3C(C)=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 WNPUMLYEQOCIHY-UHFFFAOYSA-N 0.000 claims 1
- GAPYLLQYZGTWHG-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(5-fluoroindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=C(F)C=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 GAPYLLQYZGTWHG-UHFFFAOYSA-N 0.000 claims 1
- OBLWQJQGEVUUAC-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(6-fluoro-2,3-dihydroindol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC(F)=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 OBLWQJQGEVUUAC-UHFFFAOYSA-N 0.000 claims 1
- JFTXWJNBANATPA-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(6-fluoro-3,4-dihydro-2h-quinolin-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=C(F)C=C3CCC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JFTXWJNBANATPA-UHFFFAOYSA-N 0.000 claims 1
- JTOWFBKWYKKKGN-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-methyl-6-(2-methylphenyl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C(=CC=CC=2)C)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JTOWFBKWYKKKGN-UHFFFAOYSA-N 0.000 claims 1
- GDTUDVMVTHXQPC-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-methyl-6-(3-methylindol-1-yl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC=CC=C3C(C)=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 GDTUDVMVTHXQPC-UHFFFAOYSA-N 0.000 claims 1
- JWLDFILNJYSUOS-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-methyl-6-(3-propan-2-ylphenyl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C=C(C=CC=2)C(C)C)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JWLDFILNJYSUOS-UHFFFAOYSA-N 0.000 claims 1
- ZSJPHHCRHFYLCJ-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-methyl-6-[3-(trifluoromethyl)phenyl]pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C=C(C=CC=2)C(F)(F)F)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ZSJPHHCRHFYLCJ-UHFFFAOYSA-N 0.000 claims 1
- JDFZCHCBSAUWRF-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[4-(5-fluoro-2,3-dihydroindol-1-yl)pyridin-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CC=C(C=2)N2C3=CC=C(F)C=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JDFZCHCBSAUWRF-UHFFFAOYSA-N 0.000 claims 1
- JAZUTBJYXOAJOE-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[4-(6-fluoro-2,3-dihydroindol-1-yl)pyridin-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CC=C(C=2)N2C3=CC(F)=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JAZUTBJYXOAJOE-UHFFFAOYSA-N 0.000 claims 1
- DUBWCLJMVVUFFK-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(1-ethylindol-3-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C12=CC=CC=C2N(CC)C=C1C(C=1)=CN=CC=1C1CCCN1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 DUBWCLJMVVUFFK-UHFFFAOYSA-N 0.000 claims 1
- OPEHGMFUUJOWFW-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(1h-indol-3-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C3=CC=CC=C3NC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 OPEHGMFUUJOWFW-UHFFFAOYSA-N 0.000 claims 1
- HMIOFHDDBLYHBH-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(2-methylphenyl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C(=CC=CC=2)C)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 HMIOFHDDBLYHBH-UHFFFAOYSA-N 0.000 claims 1
- ZDFXXULSSKPTMS-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(3,4-dihydro-2h-quinolin-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=CC=C3CCC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ZDFXXULSSKPTMS-UHFFFAOYSA-N 0.000 claims 1
- FAWAIFXSDIHOSQ-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(3,4-dihydro-2h-quinolin-1-yl)pyridin-3-yl]pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=CC=C3CCC2)N1CC(NC(=O)C(C)NC)C1CCCCC1 FAWAIFXSDIHOSQ-UHFFFAOYSA-N 0.000 claims 1
- HZJHWCJCYNSURC-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(3,5-dimethylphenyl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=C(C)C=C(C)C=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 HZJHWCJCYNSURC-UHFFFAOYSA-N 0.000 claims 1
- JTBVHUYPCGPJOD-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(3-methylindol-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=CC=C3C(C)=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JTBVHUYPCGPJOD-UHFFFAOYSA-N 0.000 claims 1
- ODAZZDHNXJTOEM-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(3-methylphenyl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=C(C)C=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ODAZZDHNXJTOEM-UHFFFAOYSA-N 0.000 claims 1
- FHVDRECTOYZHFS-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(4-fluorophenyl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=CC(F)=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 FHVDRECTOYZHFS-UHFFFAOYSA-N 0.000 claims 1
- VYSMMNAWNFFIFE-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(4-methylphenyl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=CC(C)=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 VYSMMNAWNFFIFE-UHFFFAOYSA-N 0.000 claims 1
- NXDAGBCECRKCGY-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(5-fluoro-2,3-dihydroindol-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=C(F)C=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 NXDAGBCECRKCGY-UHFFFAOYSA-N 0.000 claims 1
- MHLTVJXWQDPCPU-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(5-fluoro-3-methylindol-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=C(F)C=C3C(C)=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 MHLTVJXWQDPCPU-UHFFFAOYSA-N 0.000 claims 1
- ATTHLCLKEPTOJP-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[5-(5-fluoroindol-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=C(F)C=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ATTHLCLKEPTOJP-UHFFFAOYSA-N 0.000 claims 1
- XQILTTPTKSWFGF-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(1h-indol-3-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C3=CC=CC=C3NC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 XQILTTPTKSWFGF-UHFFFAOYSA-N 0.000 claims 1
- RDQMCTFCOCDMOT-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(1h-indol-3-yl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CN=C(C=2)C=2C3=CC=CC=C3NC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 RDQMCTFCOCDMOT-UHFFFAOYSA-N 0.000 claims 1
- IVMUAGOPSXOMJW-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(2,3-dihydroindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 IVMUAGOPSXOMJW-UHFFFAOYSA-N 0.000 claims 1
- AEOVQBQKSAHDAB-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(2-methylphenyl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CN=C(C=2)C=2C(=CC=CC=2)C)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 AEOVQBQKSAHDAB-UHFFFAOYSA-N 0.000 claims 1
- CXPHSMMOVQTYTM-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(5-fluoro-2,3-dihydroindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC=C(F)C=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 CXPHSMMOVQTYTM-UHFFFAOYSA-N 0.000 claims 1
- OEGRLTUDZRPJQO-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(5-fluoro-2,3-dihydroindol-1-yl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CN=C(C=2)N2C3=CC=C(F)C=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 OEGRLTUDZRPJQO-UHFFFAOYSA-N 0.000 claims 1
- SIRHPGRSGCAACR-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(5-fluoro-3-methylindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC=C(F)C=C3C(C)=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 SIRHPGRSGCAACR-UHFFFAOYSA-N 0.000 claims 1
- YVBPZXAJJFSRPT-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(5-fluoro-3-methylindol-1-yl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CN=C(C=2)N2C3=CC=C(F)C=C3C(C)=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 YVBPZXAJJFSRPT-UHFFFAOYSA-N 0.000 claims 1
- HYXZYJVQSLANBR-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(5-fluoroindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC=C(F)C=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 HYXZYJVQSLANBR-UHFFFAOYSA-N 0.000 claims 1
- PMOKOUHGBMLWHG-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(5-fluoroindol-1-yl)pyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=CN=C(C=2)N2C3=CC=C(F)C=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 PMOKOUHGBMLWHG-UHFFFAOYSA-N 0.000 claims 1
- LMXRCVIBVVSIRR-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[6-(6-fluoro-2,3-dihydroindol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC(F)=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 LMXRCVIBVVSIRR-UHFFFAOYSA-N 0.000 claims 1
- NODCRGNTDODBIR-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[7-(4-fluorophenyl)-1,3-benzothiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2SC3=C(C=4C=CC(F)=CC=4)C=CC=C3N=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 NODCRGNTDODBIR-UHFFFAOYSA-N 0.000 claims 1
- OUHAEMWXPWJNIQ-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(1-phenylisoquinolin-7-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C3C(C=4C=CC=CC=4)=NC=CC3=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 OUHAEMWXPWJNIQ-UHFFFAOYSA-N 0.000 claims 1
- NDMHFSMFOWUWNP-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(5-phenyl-5,6,7,8-tetrahydroquinolin-3-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C3C(C=4C=CC=CC=4)CCCC3=NC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 NDMHFSMFOWUWNP-UHFFFAOYSA-N 0.000 claims 1
- YDIHYDFUZAPBPN-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(5-pyridin-2-ylpyridin-3-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2N=CC=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 YDIHYDFUZAPBPN-UHFFFAOYSA-N 0.000 claims 1
- YEYOELVULLXEEQ-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(5-pyridin-3-ylpyridin-3-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=NC=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 YEYOELVULLXEEQ-UHFFFAOYSA-N 0.000 claims 1
- YWJWJHNKGVKJAA-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(5-pyridin-4-ylpyridin-3-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=CN=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 YWJWJHNKGVKJAA-UHFFFAOYSA-N 0.000 claims 1
- MUAIQVLACXCQPX-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(5-pyrrolo[2,3-b]pyridin-1-ylpyridin-3-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=NC=CC=C3C=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 MUAIQVLACXCQPX-UHFFFAOYSA-N 0.000 claims 1
- GWEGLPWVIJEVOH-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(7-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2SC=3C(CCCC=3N=2)C=2C=CC=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 GWEGLPWVIJEVOH-UHFFFAOYSA-N 0.000 claims 1
- FUQGIYZAECHMLP-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-(7-phenyl-6,7-dihydro-5h-cyclopenta[c]pyridin-4-yl)pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=3CCC(C=3C=NC=2)C=2C=CC=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 FUQGIYZAECHMLP-UHFFFAOYSA-N 0.000 claims 1
- RQSXFKVWIWFHFQ-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-[2-(2-oxo-3,4-dihydroquinolin-1-yl)pyridin-4-yl]pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=CC=C3CCC2=O)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 RQSXFKVWIWFHFQ-UHFFFAOYSA-N 0.000 claims 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000006225 natural substrate Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008823 permeabilization Effects 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000861 pro-apoptotic effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82923406P | 2006-10-12 | 2006-10-12 | |
| US60/829,234 | 2006-10-12 | ||
| PCT/US2007/080875 WO2008045905A1 (en) | 2006-10-12 | 2007-10-10 | Pyrrolydine derivatives as iap inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2666112A1 true CA2666112A1 (en) | 2008-04-17 |
Family
ID=38984426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002666112A Abandoned CA2666112A1 (en) | 2006-10-12 | 2007-10-10 | Pyrrolydine derivatives as iap inhibitors |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8044209B2 (enExample) |
| EP (1) | EP2102229B1 (enExample) |
| JP (1) | JP5190062B2 (enExample) |
| KR (1) | KR20090065548A (enExample) |
| CN (1) | CN101595121A (enExample) |
| AU (1) | AU2007307763A1 (enExample) |
| BR (1) | BRPI0719221A2 (enExample) |
| CA (1) | CA2666112A1 (enExample) |
| MX (1) | MX2009003834A (enExample) |
| RU (1) | RU2009117701A (enExample) |
| WO (1) | WO2008045905A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA019420B1 (ru) | 2004-12-20 | 2014-03-31 | Дженентех, Инк. | Пирролидиновые ингибиторы иап (ингибиторов апоптоза) |
| CA2607940C (en) | 2005-05-18 | 2009-12-15 | Aegera Therapeutics Inc. | Bir domain binding compounds |
| WO2007048224A1 (en) | 2005-10-25 | 2007-05-03 | Aegera Therapeutics Inc. | Iap bir domain binding compounds |
| CN101374829A (zh) | 2005-12-19 | 2009-02-25 | 健泰科生物技术公司 | Iap的抑制剂 |
| TWI543988B (zh) | 2006-03-16 | 2016-08-01 | 科學製藥股份有限公司 | 結合於細胞凋亡抑制蛋白（ｉａｐ）之桿狀病毒ｉａｐ重複序列（ｂｉｒ）區域之化合物 |
| US8110681B2 (en) | 2006-03-17 | 2012-02-07 | The United States Of America As Represented By The Secretary, Department Of Health And Human Services | Compounds for the treatment of spinal muscular atrophy and other uses |
| MY159563A (en) | 2006-05-16 | 2017-01-13 | Pharmascience Inc | Iap bir domain binding compounds |
| PE20110224A1 (es) * | 2006-08-02 | 2011-04-05 | Novartis Ag | PROCEDIMIENTO PARA LA SINTESIS DE UN PEPTIDOMIMETICO DE Smac INHIBIDOR DE IAP, Y COMPUESTOS INTERMEDIARIOS PARA LA SINTESIS DEL MISMO |
| JP2010513561A (ja) * | 2006-12-19 | 2010-04-30 | ジェネンテック， インコーポレイテッド | Ｉａｐのイミダゾピリジンインヒビター |
| AR066348A1 (es) | 2007-04-30 | 2009-08-12 | Genentech Inc | Inhibidores de las iap |
| ES2882855T3 (es) | 2008-05-16 | 2021-12-02 | Dana Farber Cancer Inst Inc | Inmunomodulación por inhibidores de IAP |
| NZ590550A (en) | 2008-08-02 | 2013-05-31 | Genentech Inc | Inhibitors of Apoptosis (IAP) for treating cancer |
| RU2523448C2 (ru) | 2008-08-04 | 2014-07-20 | СиЭйчДиАй ФАУНДЕЙШН, Инк, | Ингибиторы кинуренин-3-монооксигеназы |
| NZ590500A (en) * | 2008-08-16 | 2012-06-29 | Genentech Inc | Azaindole inhibitors of iap |
| JP2012500260A (ja) * | 2008-08-18 | 2012-01-05 | イェール・ユニヴァーシティー | Ｍｉｆモジュレーター |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| US20100317593A1 (en) * | 2009-06-12 | 2010-12-16 | Astrazeneca Ab | 2,3-dihydro-1h-indene compounds |
| US20110034469A1 (en) | 2009-08-04 | 2011-02-10 | Takeda Pharmaceutical Company Limited | Heterocyclic Compound |
| CA2784748A1 (en) | 2009-12-18 | 2011-06-23 | Idenix Pharmaceuticals, Inc. | 5,5-fused arylene or heteroarylene hepatitis c virus inhibitors |
| NZ602368A (en) | 2010-02-12 | 2014-10-31 | Pharmascience Inc | Iap bir domain binding compounds |
| DK2611797T3 (en) * | 2010-08-31 | 2017-02-13 | Hanmi Science Co Ltd | QUINOLINE OR QUINAZOLINE DERIVATIVES WITH APOPTOSE-INducing ACTIVITY ON CELLS |
| CN103261186A (zh) * | 2010-12-13 | 2013-08-21 | 诺瓦提斯公司 | 二聚化iap抑制剂 |
| UY33794A (es) * | 2010-12-13 | 2012-07-31 | Novartis Ag | Inhibidores diméricos de las iap |
| JP2014094886A (ja) * | 2011-02-28 | 2014-05-22 | Nippon Chemiphar Co Ltd | Ｇｐｒ１１９作動薬 |
| GB201106817D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compound |
| CN103841829A (zh) * | 2011-07-28 | 2014-06-04 | Chdi基金会股份有限公司 | 某些犬尿氨酸-3-单加氧酶抑制剂、其药物组合物及其使用方法 |
| CA2844521A1 (en) | 2011-08-30 | 2013-03-07 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| DK2750677T3 (en) | 2011-08-30 | 2017-07-10 | Chdi Foundation Inc | KYNURENIN-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND PROCEDURES FOR USE THEREOF |
| NO2755614T3 (enExample) * | 2012-01-03 | 2018-03-31 | ||
| JP6321020B2 (ja) * | 2012-10-19 | 2018-05-09 | アステックス、セラピューティックス、リミテッドＡｓｔｅｘ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | 二環式複素環化合物およびそれらの治療での使用 |
| GB201218862D0 (en) * | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| JP6324976B2 (ja) * | 2012-10-19 | 2018-05-16 | アステックス、セラピューティックス、リミテッドＡｓｔｅｘ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | 二環式複素環化合物およびそれらの治療での使用 |
| US9980973B2 (en) | 2012-10-19 | 2018-05-29 | Astex Therapeutics Limited | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218864D0 (en) * | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218850D0 (en) * | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| LT3083616T (lt) | 2013-12-20 | 2021-09-10 | Astex Therapeutics Limited | Bicikinių heterociklų junginiai ir jų panaudojimas terapijoje |
| CA2974651A1 (en) | 2014-01-24 | 2015-07-30 | Children's Hospital Of Eastern Ontario Research Institute Inc. | Smc combination therapy for the treatment of cancer |
| CR20170061A (es) | 2014-07-17 | 2017-07-17 | Chdi Foundation Inc | Métodos y composiciones para el tratamiento de trastornos relacionados con vih |
| KR20170004160A (ko) * | 2015-07-01 | 2017-01-11 | 엘지전자 주식회사 | 이동단말기 및 그 제어방법 |
| TWI773657B (zh) | 2015-12-18 | 2022-08-11 | 美商亞德利克斯公司 | 作爲非全身ｔｇｒ５促效劑之經取代之4-苯基吡啶化合物 |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
| CN114685602A (zh) | 2017-11-13 | 2022-07-01 | 正大天晴药业集团股份有限公司 | 用作iap抑制剂的smac模拟物及其用途 |
| EP3831811A4 (en) | 2018-07-31 | 2022-04-20 | Fimecs, Inc. | HETEROCYCLIC COMPOUND |
| EP3936126A4 (en) * | 2019-03-07 | 2022-12-21 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | COMBINATION OF IAP INHIBITOR AND IMMUNE CHECKPOINT INHIBITOR |
| PT3967702T (pt) * | 2019-05-10 | 2024-04-09 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | Cristalização de miméticos de smac utilizados como inibidores de iap e método para a sua preparação |
| JP7764027B2 (ja) | 2019-07-31 | 2025-11-05 | ファイメクス株式会社 | 複素環化合物 |
| CN112521372B (zh) * | 2019-09-18 | 2022-07-08 | 南京华威医药科技集团有限公司 | 一种细胞凋亡蛋白抑制剂及其制备方法和用途 |
| AU2021211871A1 (en) | 2020-01-20 | 2022-09-08 | Astrazeneca Ab | Epidermal growth factor receptor tyrosine kinase inhibitors for the treatment of cancer |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA02000823A (es) | 2000-05-23 | 2002-07-30 | Vertex Pharma | Inhibidores de caspasa y uso de los mismos. |
| US20060128632A1 (en) | 2002-07-02 | 2006-06-15 | Sharma Sushil K | Peptide inhibitors of smac protein binding to inhibitor of apoptosis proteins (iap) |
| DE60324964D1 (de) | 2002-07-15 | 2009-01-08 | Univ Princeton | Iap-bindende verbindungen |
| WO2005097791A1 (en) | 2004-04-07 | 2005-10-20 | Novartis Ag | Inhibitors of iap |
| WO2006014361A1 (en) * | 2004-07-02 | 2006-02-09 | Genentech, Inc. | Inhibitors of iap |
| EA019420B1 (ru) * | 2004-12-20 | 2014-03-31 | Дженентех, Инк. | Пирролидиновые ингибиторы иап (ингибиторов апоптоза) |
| CN101374829A (zh) * | 2005-12-19 | 2009-02-25 | 健泰科生物技术公司 | Iap的抑制剂 |
-
2007
- 2007-10-10 JP JP2009532544A patent/JP5190062B2/ja not_active Expired - Fee Related
- 2007-10-10 US US12/445,435 patent/US8044209B2/en not_active Expired - Fee Related
- 2007-10-10 BR BRPI0719221-5A patent/BRPI0719221A2/pt not_active Application Discontinuation
- 2007-10-10 CA CA002666112A patent/CA2666112A1/en not_active Abandoned
- 2007-10-10 WO PCT/US2007/080875 patent/WO2008045905A1/en not_active Ceased
- 2007-10-10 KR KR1020097009617A patent/KR20090065548A/ko not_active Withdrawn
- 2007-10-10 MX MX2009003834A patent/MX2009003834A/es unknown
- 2007-10-10 CN CNA2007800458268A patent/CN101595121A/zh active Pending
- 2007-10-10 EP EP07844058.3A patent/EP2102229B1/en not_active Not-in-force
- 2007-10-10 RU RU2009117701/04A patent/RU2009117701A/ru not_active Application Discontinuation
- 2007-10-10 AU AU2007307763A patent/AU2007307763A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2102229A1 (en) | 2009-09-23 |
| US20110015232A1 (en) | 2011-01-20 |
| JP2010506847A (ja) | 2010-03-04 |
| JP5190062B2 (ja) | 2013-04-24 |
| EP2102229B1 (en) | 2014-03-26 |
| RU2009117701A (ru) | 2010-11-20 |
| AU2007307763A1 (en) | 2008-04-17 |
| BRPI0719221A2 (pt) | 2014-03-18 |
| KR20090065548A (ko) | 2009-06-22 |
| MX2009003834A (es) | 2009-04-22 |
| US8044209B2 (en) | 2011-10-25 |
| WO2008045905A1 (en) | 2008-04-17 |
| CN101595121A (zh) | 2009-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |