RU2009117701A - Производные пирролидина в качестве ингибиторов iap - Google Patents
Производные пирролидина в качестве ингибиторов iap Download PDFInfo
- Publication number
- RU2009117701A RU2009117701A RU2009117701/04A RU2009117701A RU2009117701A RU 2009117701 A RU2009117701 A RU 2009117701A RU 2009117701/04 A RU2009117701/04 A RU 2009117701/04A RU 2009117701 A RU2009117701 A RU 2009117701A RU 2009117701 A RU2009117701 A RU 2009117701A
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- RU
- Russia
- Prior art keywords
- methylaminopropionamide
- pyrrolidin
- cyclohexyl
- oxoethyl
- alkyl
- Prior art date
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 31
- 125000003118 aryl group Chemical group 0.000 claims abstract 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract 10
- 150000002367 halogens Chemical class 0.000 claims abstract 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000004429 atom Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- -1 C 1 -C 6 alkyl Chemical class 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 6
- 125000005135 aryl sulfinyl group Chemical class 0.000 claims 6
- 230000004663 cell proliferation Effects 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical class 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001041 indolyl 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-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
- 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 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
- 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
- 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
- XGAQLJAHEOQJEK-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-(5-indazol-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=N2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 XGAQLJAHEOQJEK-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
- 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
- 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
- PMGJRUUGMSDLFS-UHFFFAOYSA-N n-[1-cyclohexyl-2-[2-[2-(2,3-dihydropyrrolo[2,3-b]pyridin-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=NC=CC=C3CC2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 PMGJRUUGMSDLFS-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
- 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
- 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
- GGHKCRDLESCNGK-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-[5-(2-oxo-1,3-benzoxazol-3-yl)pyridin-3-yl]pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C(OC3=CC=CC=C32)=O)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 GGHKCRDLESCNGK-UHFFFAOYSA-N 0.000 claims 1
- ZQMPLQQWXYDNJH-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-[5-(3-propan-2-ylphenyl)pyridin-3-yl]pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=C(C=CC=2)C(C)C)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ZQMPLQQWXYDNJH-UHFFFAOYSA-N 0.000 claims 1
- DLNBEQXNSYLYKC-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-[5-[2-(trifluoromethyl)phenyl]pyridin-3-yl]pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C(=CC=CC=2)C(F)(F)F)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 DLNBEQXNSYLYKC-UHFFFAOYSA-N 0.000 claims 1
- JQAJJOGXEKNMMF-UHFFFAOYSA-N n-[1-cyclohexyl-2-oxo-2-[2-[5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]pyrrolidin-1-yl]ethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=C(C=CC=2)C(F)(F)F)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JQAJJOGXEKNMMF-UHFFFAOYSA-N 0.000 claims 1
- UIXOHZCIPPMIAW-UHFFFAOYSA-N n-[2-[2-[2-(benzimidazol-1-yl)-3-fluoropyridin-4-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C(=C(N=CC=2)N2C3=CC=CC=C3N=C2)F)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 UIXOHZCIPPMIAW-UHFFFAOYSA-N 0.000 claims 1
- VGEUVMOYDOVSKH-UHFFFAOYSA-N n-[2-[2-[2-(benzimidazol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=CC=C3N=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 VGEUVMOYDOVSKH-UHFFFAOYSA-N 0.000 claims 1
- OZDXQKDLPZELCL-UHFFFAOYSA-N n-[2-[2-[2-(benzotriazol-1-yl)pyridin-4-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(N=CC=2)N2C3=CC=CC=C3N=N2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 OZDXQKDLPZELCL-UHFFFAOYSA-N 0.000 claims 1
- HKXOCRAKLRXQOB-UHFFFAOYSA-N n-[2-[2-[2-chloro-5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C(=NC=C(C=2)C=2C=C(C=CC=2)C(F)(F)F)Cl)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 HKXOCRAKLRXQOB-UHFFFAOYSA-N 0.000 claims 1
- ACQFZFNGNCKJHL-UHFFFAOYSA-N n-[2-[2-[5-(1,3-benzodioxol-5-yl)pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=C3OCOC3=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 ACQFZFNGNCKJHL-UHFFFAOYSA-N 0.000 claims 1
- SMZDINRQEPZNIY-UHFFFAOYSA-N n-[2-[2-[5-(1-benzofuran-3-yl)pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C3=CC=CC=C3OC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 SMZDINRQEPZNIY-UHFFFAOYSA-N 0.000 claims 1
- QDQITGHOZJQRQR-UHFFFAOYSA-N n-[2-[2-[5-(4-tert-butylphenyl)pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=CC(=CC=2)C(C)(C)C)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 QDQITGHOZJQRQR-UHFFFAOYSA-N 0.000 claims 1
- HQGGADGIAMAXHB-UHFFFAOYSA-N n-[2-[2-[5-(5-chloro-2-methoxyphenyl)pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C(=CC=C(Cl)C=2)OC)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 HQGGADGIAMAXHB-UHFFFAOYSA-N 0.000 claims 1
- JYUHHFYRRYWOIZ-UHFFFAOYSA-N n-[2-[2-[5-(benzimidazol-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=CC=C3N=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 JYUHHFYRRYWOIZ-UHFFFAOYSA-N 0.000 claims 1
- DCLLXJGAQAKDMU-UHFFFAOYSA-N n-[2-[2-[5-(benzotriazol-1-yl)pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)N2C3=CC=CC=C3N=N2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 DCLLXJGAQAKDMU-UHFFFAOYSA-N 0.000 claims 1
- WIGFJCSIQUDLNY-UHFFFAOYSA-N n-[2-[2-[5-[3,5-bis(trifluoromethyl)phenyl]pyridin-3-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2C=C(C=NC=2)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 WIGFJCSIQUDLNY-UHFFFAOYSA-N 0.000 claims 1
- IUAUCCYLKAXYHM-UHFFFAOYSA-N n-[2-[2-[6-(1,3-benzodioxol-5-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)C=2C=C3OCOC3=CC=2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 IUAUCCYLKAXYHM-UHFFFAOYSA-N 0.000 claims 1
- QZJCOEWYUFESAM-UHFFFAOYSA-N n-[2-[2-[6-(benzimidazol-1-yl)-2-methylpyrimidin-4-yl]pyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-2-(methylamino)propanamide Chemical compound C1CCC(C=2N=C(C)N=C(C=2)N2C3=CC=CC=C3N=C2)N1C(=O)C(NC(=O)C(C)NC)C1CCCCC1 QZJCOEWYUFESAM-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 abstract 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 abstract 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82923406P | 2006-10-12 | 2006-10-12 | |
| US60/829,234 | 2006-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2009117701A true RU2009117701A (ru) | 2010-11-20 |
Family
ID=38984426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009117701/04A RU2009117701A (ru) | 2006-10-12 | 2007-10-10 | Производные пирролидина в качестве ингибиторов iap |
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 (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2007007195A (es) | 2004-12-20 | 2007-10-08 | Genentech Inc | Inhibidores de pirrolidina de iap. |
| WO2006122408A1 (en) | 2005-05-18 | 2006-11-23 | Aegera Therapeutics Inc. | Bir domain binding compounds |
| AU2006308453B9 (en) | 2005-10-25 | 2011-12-01 | Pharmascience Inc. | IAP BIR domain binding compounds |
| WO2007106192A2 (en) | 2005-12-19 | 2007-09-20 | Genentech, Inc. | Inhibitors of iap |
| TWI504597B (zh) | 2006-03-16 | 2015-10-21 | Pharmascience Inc | 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 |
| BRPI0711591A2 (pt) | 2006-05-16 | 2011-11-16 | Aegera Therapeutics, Inc. | composto de ligação de domìnio bir da iap |
| PE20110217A1 (es) * | 2006-08-02 | 2011-04-01 | Novartis Ag | DERIVADOS DE 2-OXO-ETIL-AMINO-PROPIONAMIDA-PIRROLIDIN-2-IL-SUSTITUIDOS COMO INHIBIDORES DEL ENLACE DE LA PROTEINA Smac AL INHIBIDOR DE LA PROTEINA DE APOPTOSIS |
| CN101605786A (zh) * | 2006-12-19 | 2009-12-16 | 健泰科生物技术公司 | 细胞凋亡抑制剂的咪唑并吡啶抑制剂 |
| NZ598890A (en) * | 2007-04-30 | 2013-10-25 | Genentech Inc | Inhibitors of iap |
| EP2296650B1 (en) | 2008-05-16 | 2020-05-06 | Novartis AG | Immunomodulation by iap inhibitors |
| US8835393B2 (en) | 2008-08-02 | 2014-09-16 | Genentech, Inc. | Inhibitors of IAP |
| BRPI0916576A2 (pt) | 2008-08-04 | 2017-06-27 | Chdi Inc | pelo menos uma entidade química, composição farmacêutica, e, método para tratar uma condição ou distúrbio. |
| JP2012500272A (ja) * | 2008-08-16 | 2012-01-05 | ジェネンテック， インコーポレイテッド | Ｉａｐのアザインドールインヒビター |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| MX2011001872A (es) * | 2008-08-18 | 2011-05-23 | Univ Yale | Moduladores de mif. |
| 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 |
| UY32826A (es) | 2009-08-04 | 2011-02-28 | Takeda Pharmaceutical | Compuestos heterocíclicos |
| MY159958A (en) | 2009-12-18 | 2017-02-15 | 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 |
| US8835458B2 (en) * | 2010-08-31 | 2014-09-16 | Hanmi Science Co., Ltd | Quinoline or quinazoline derivatives with apoptosis inducing activity on cells |
| JP2014501235A (ja) | 2010-12-13 | 2014-01-20 | ノバルティス アーゲー | 二量体ｉａｐ阻害剤 |
| 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 |
| PH12014500239A1 (en) * | 2011-07-28 | 2014-03-31 | Chdi Foundation Inc | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| WO2013033068A1 (en) | 2011-08-30 | 2013-03-07 | Stephen Martin Courtney | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| SG2014012926A (en) | 2011-08-30 | 2014-06-27 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| NO2755614T3 (enExample) | 2012-01-03 | 2018-03-31 | ||
| GB201218864D0 (en) * | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218862D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| 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 |
| US9980973B2 (en) | 2012-10-19 | 2018-05-29 | Astex Therapeutics Limited | 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 |
| CN115368356B (zh) | 2013-12-20 | 2025-05-09 | 阿斯特克斯治疗有限公司 | 双环杂环化合物及其治疗用途 |
| WO2015109391A1 (en) | 2014-01-24 | 2015-07-30 | Children's Hospital Of Eastern Ontario Research Institute Inc. | Smc combination therapy for the treatment of cancer |
| MX372995B (es) | 2014-07-17 | 2020-04-13 | Chdi Foundation Inc | Metodos 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 |
| CN111247161B (zh) * | 2017-11-13 | 2021-12-31 | 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 |
| WO2020027225A1 (ja) | 2018-07-31 | 2020-02-06 | ファイメクス株式会社 | 複素環化合物 |
| US20220175917A1 (en) * | 2019-03-07 | 2022-06-09 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Combination of iap inhibitor and immune checkpoint inhibitor |
| WO2020228642A1 (zh) * | 2019-05-10 | 2020-11-19 | 正大天晴药业集团股份有限公司 | 一种用作iap抑制剂的smac模拟物的结晶及其制备方法 |
| 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 |
| US20230056604A1 (en) | 2020-01-20 | 2023-02-23 | 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 |
|---|---|---|---|---|
| NZ516918A (en) | 2000-05-23 | 2004-06-25 | Vertex Pharma | Caspase inhibitors and uses thereof |
| WO2004007529A2 (en) * | 2002-07-15 | 2004-01-22 | The Trustees Of Princeton University | Iap binding compounds |
| CA2491041A1 (en) | 2002-07-02 | 2004-01-15 | Novartis Ag | Peptide inhibitors of smac protein binding to inhibitor of apoptosis proteins (iap) |
| PL2253614T3 (pl) | 2004-04-07 | 2013-03-29 | Novartis Ag | Inhibitory IAP |
| KR100926203B1 (ko) * | 2004-07-02 | 2009-11-09 | 제넨테크, 인크. | Ｉａｐ의 억제제 |
| MX2007007195A (es) * | 2004-12-20 | 2007-10-08 | Genentech Inc | Inhibidores de pirrolidina de iap. |
| WO2007106192A2 (en) * | 2005-12-19 | 2007-09-20 | Genentech, Inc. | Inhibitors of iap |
-
2007
- 2007-10-10 AU AU2007307763A patent/AU2007307763A1/en not_active Abandoned
- 2007-10-10 RU RU2009117701/04A patent/RU2009117701A/ru not_active Application Discontinuation
- 2007-10-10 WO PCT/US2007/080875 patent/WO2008045905A1/en not_active Ceased
- 2007-10-10 BR BRPI0719221-5A patent/BRPI0719221A2/pt not_active Application Discontinuation
- 2007-10-10 EP EP07844058.3A patent/EP2102229B1/en not_active Not-in-force
- 2007-10-10 MX MX2009003834A patent/MX2009003834A/es unknown
- 2007-10-10 JP JP2009532544A patent/JP5190062B2/ja not_active Expired - Fee Related
- 2007-10-10 CN CNA2007800458268A patent/CN101595121A/zh active Pending
- 2007-10-10 CA CA002666112A patent/CA2666112A1/en not_active Abandoned
- 2007-10-10 KR KR1020097009617A patent/KR20090065548A/ko not_active Withdrawn
- 2007-10-10 US US12/445,435 patent/US8044209B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP5190062B2 (ja) | 2013-04-24 |
| KR20090065548A (ko) | 2009-06-22 |
| US20110015232A1 (en) | 2011-01-20 |
| EP2102229A1 (en) | 2009-09-23 |
| US8044209B2 (en) | 2011-10-25 |
| CN101595121A (zh) | 2009-12-02 |
| BRPI0719221A2 (pt) | 2014-03-18 |
| CA2666112A1 (en) | 2008-04-17 |
| JP2010506847A (ja) | 2010-03-04 |
| AU2007307763A1 (en) | 2008-04-17 |
| WO2008045905A1 (en) | 2008-04-17 |
| MX2009003834A (es) | 2009-04-22 |
| EP2102229B1 (en) | 2014-03-26 |
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