RU2018123779A - Новые соединения - Google Patents
Новые соединения Download PDFInfo
- Publication number
- RU2018123779A RU2018123779A RU2018123779A RU2018123779A RU2018123779A RU 2018123779 A RU2018123779 A RU 2018123779A RU 2018123779 A RU2018123779 A RU 2018123779A RU 2018123779 A RU2018123779 A RU 2018123779A RU 2018123779 A RU2018123779 A RU 2018123779A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- cyanopyrrolidin
- carboxamide
- optionally substituted
- carbonitrile
- Prior art date
Links
- -1 cyano, hydroxyl Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- DSIBSRXKQRYPJP-UHFFFAOYSA-N 1,2-oxazole-5-carboxamide Chemical compound NC(=O)C1=CC=NO1 DSIBSRXKQRYPJP-UHFFFAOYSA-N 0.000 claims 2
- KINAZPSFJPPTNP-UHFFFAOYSA-N 1-benzyl-N-[(1-cyanopyrrolidin-3-yl)methyl]indazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=C(C2=CC=CC=C12)C(=O)NCC1CN(CC1)C#N KINAZPSFJPPTNP-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- BEHYAANJUKYBTH-UHFFFAOYSA-N imidazo[1,2-a]pyridine-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CN21 BEHYAANJUKYBTH-UHFFFAOYSA-N 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- XRKWRSYZFZXPNK-GFCCVEGCSA-N (3R)-3-[[(5-phenyl-1,3-thiazol-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CN=C(S1)NC[C@@H]1CN(CC1)C#N XRKWRSYZFZXPNK-GFCCVEGCSA-N 0.000 claims 1
- QTAQRVFBNSFBTI-GFCCVEGCSA-N (3R)-3-[[[7-(1H-pyrazol-4-yl)quinazolin-2-yl]amino]methyl]pyrrolidine-1-carbonitrile Chemical compound N1N=CC(=C1)C1=CC=C2C=NC(=NC2=C1)NC[C@@H]1CN(CC1)C#N QTAQRVFBNSFBTI-GFCCVEGCSA-N 0.000 claims 1
- CZPJNEFJNYKUES-ZDUSSCGKSA-N (3S)-3-[[(4-phenylpyrimidin-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NC(=NC=C1)NC[C@H]1CN(CC1)C#N CZPJNEFJNYKUES-ZDUSSCGKSA-N 0.000 claims 1
- XRKWRSYZFZXPNK-LBPRGKRZSA-N (3S)-3-[[(5-phenyl-1,3-thiazol-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CN=C(S1)NC[C@H]1CN(CC1)C#N XRKWRSYZFZXPNK-LBPRGKRZSA-N 0.000 claims 1
- VYAVKGQLSHJAKT-STQMWFEESA-N (3aR,6aS)-4-oxo-5-(5-phenyl-1,3-thiazol-2-yl)-3,3a,6,6a-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-2-carbonitrile Chemical compound O=C1[C@@H]2[C@H](CN1C=1SC(=CN=1)C1=CC=CC=C1)CN(C2)C#N VYAVKGQLSHJAKT-STQMWFEESA-N 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- JZUCLLKLEMMQAS-HWKANZROSA-N (E)-N-[(1-cyanopyrrolidin-3-yl)methyl]-3-(2-fluoro-4-methoxyphenyl)prop-2-enamide Chemical compound C(#N)N1CC(CC1)CNC(\C=C\C1=C(C=C(C=C1)OC)F)=O JZUCLLKLEMMQAS-HWKANZROSA-N 0.000 claims 1
- ITRNJIHJJWXGBV-UHFFFAOYSA-N 1-(3-benzylphenyl)-3-[(1-cyanopyrrolidin-3-yl)methyl]urea Chemical compound C(C1=CC=CC=C1)C=1C=C(C=CC=1)NC(=O)NCC1CN(CC1)C#N ITRNJIHJJWXGBV-UHFFFAOYSA-N 0.000 claims 1
- WOLDJIHMNJCNBH-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[(1-cyanopyrrolidin-3-yl)methyl]urea Chemical compound ClC=1C=C(C=CC=1)NC(=O)NCC1CN(CC1)C#N WOLDJIHMNJCNBH-UHFFFAOYSA-N 0.000 claims 1
- KPIDBNWWWTWMBH-CQSZACIVSA-N 1-(3-cyanophenyl)-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]imidazole-4-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)N1C=NC(=C1)C(=O)NC[C@@H]1CN(CC1)C#N KPIDBNWWWTWMBH-CQSZACIVSA-N 0.000 claims 1
- GUDNWIAYUBLOGW-CQSZACIVSA-N 1-(4-cyanophenyl)-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]imidazole-4-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)N1C=NC(=C1)C(=O)NC[C@@H]1CN(CC1)C#N GUDNWIAYUBLOGW-CQSZACIVSA-N 0.000 claims 1
- GBJREHGFNWGHMH-UHFFFAOYSA-N 1-[(1-cyanopyrrolidin-3-yl)methyl]-3-(2,4-dichlorophenyl)urea Chemical compound C(#N)N1CC(CC1)CNC(=O)NC1=C(C=C(C=C1)Cl)Cl GBJREHGFNWGHMH-UHFFFAOYSA-N 0.000 claims 1
- QNPZPLVZKIOXGN-UHFFFAOYSA-N 1-[(1-cyanopyrrolidin-3-yl)methyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound C(#N)N1CC(CC1)CNC(=O)NC1=C(C=CC(=C1)C)F QNPZPLVZKIOXGN-UHFFFAOYSA-N 0.000 claims 1
- RWLCHIZFNSNKED-UHFFFAOYSA-N 1-[(1-cyanopyrrolidin-3-yl)methyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C(#N)N1CC(CC1)CNC(=O)NC1=CC=C(C=C1)C(F)(F)F RWLCHIZFNSNKED-UHFFFAOYSA-N 0.000 claims 1
- IOBLTEUPRJUINX-UHFFFAOYSA-N 1-benzyl-N-[(1-cyanopyrrolidin-3-yl)methyl]-5-methylpyrazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=C(C=C1C)C(=O)NCC1CN(CC1)C#N IOBLTEUPRJUINX-UHFFFAOYSA-N 0.000 claims 1
- KESUWHZQFPDSAF-OAHLLOKOSA-N 1-benzyl-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]imidazole-4-carboxamide Chemical compound C(C1=CC=CC=C1)N1C=NC(=C1)C(=O)NC[C@@H]1CN(CC1)C#N KESUWHZQFPDSAF-OAHLLOKOSA-N 0.000 claims 1
- ZXVWNENATYDNBQ-UHFFFAOYSA-N 2-[1-(1-cyanopyrrolidin-3-yl)ethylamino]-1,3-benzothiazole-6-carbonitrile Chemical compound C(#N)N1CC(CC1)C(C)NC=1SC2=C(N=1)C=CC(=C2)C#N ZXVWNENATYDNBQ-UHFFFAOYSA-N 0.000 claims 1
- KEYYINNTTKJMNJ-UHFFFAOYSA-N 2h-1,4-oxazine-6-carboxamide Chemical compound NC(=O)C1=CN=CCO1 KEYYINNTTKJMNJ-UHFFFAOYSA-N 0.000 claims 1
- KKOVOFAIBOKHBV-LLVKDONJSA-N 3-(2-chlorophenyl)-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1,2-oxazole-5-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NOC(=C1)C(=O)NC[C@@H]1CN(CC1)C#N KKOVOFAIBOKHBV-LLVKDONJSA-N 0.000 claims 1
- HXYBWEWPHAZVBG-UHFFFAOYSA-N 3-[(1,3-benzothiazol-2-ylamino)-cyanomethyl]pyrrolidine-1-carbonitrile Chemical compound S1C(=NC2=C1C=CC=C2)NC(C1CN(CC1)C#N)C#N HXYBWEWPHAZVBG-UHFFFAOYSA-N 0.000 claims 1
- UCGYLXZVQNTFRU-UHFFFAOYSA-N 3-[(1-cyanopyrrolidin-3-yl)methylamino]-N-methylisoquinoline-6-carboxamide Chemical compound C(#N)N1CC(CC1)CNC=1N=CC2=CC=C(C=C2C=1)C(=O)NC UCGYLXZVQNTFRU-UHFFFAOYSA-N 0.000 claims 1
- UEBMHGLLMLHGJO-UHFFFAOYSA-N 3-[(1-cyanopyrrolidin-3-yl)methylamino]isoquinoline-6-carbonitrile Chemical compound C(#N)N1CC(CC1)CNC=1N=CC2=CC=C(C=C2C=1)C#N UEBMHGLLMLHGJO-UHFFFAOYSA-N 0.000 claims 1
- PYUGKMVIOCPOBN-UHFFFAOYSA-N 3-[(isoquinolin-1-ylamino)methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=NC=CC2=CC=CC=C12)NCC1CN(CC1)C#N PYUGKMVIOCPOBN-UHFFFAOYSA-N 0.000 claims 1
- YOKSHJPDBNAERK-UHFFFAOYSA-N 3-[(quinolin-2-ylamino)methyl]pyrrolidine-1-carbonitrile Chemical compound N1=C(C=CC2=CC=CC=C12)NCC1CN(CC1)C#N YOKSHJPDBNAERK-UHFFFAOYSA-N 0.000 claims 1
- YBGZQHXEUGOVCC-UHFFFAOYSA-N 3-[1-(1-cyanopyrrolidin-3-yl)ethylamino]isoquinoline-6-carbonitrile Chemical compound C(#N)N1CC(CC1)C(C)NC=1N=CC2=CC=C(C=C2C=1)C#N YBGZQHXEUGOVCC-UHFFFAOYSA-N 0.000 claims 1
- JYYXDFOTOBXNPH-UHFFFAOYSA-N 3-[1-(isoquinolin-3-ylamino)ethyl]pyrrolidine-1-carbonitrile Chemical compound C1=NC(=CC2=CC=CC=C12)NC(C)C1CN(CC1)C#N JYYXDFOTOBXNPH-UHFFFAOYSA-N 0.000 claims 1
- NNGLYZOCCYHEFK-UHFFFAOYSA-N 3-[1-[[6-(1H-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]ethyl]pyrrolidine-1-carbonitrile Chemical compound N1N=CC(=C1)C1=CC2=C(N=C(S2)NC(C)C2CN(CC2)C#N)C=C1 NNGLYZOCCYHEFK-UHFFFAOYSA-N 0.000 claims 1
- UOADHNIYFIKIMN-UHFFFAOYSA-N 3-[1-[[6-(5-methyl-1,2-oxazol-4-yl)-1,3-benzothiazol-2-yl]amino]ethyl]pyrrolidine-1-carbonitrile Chemical compound CC1=C(C=NO1)C1=CC2=C(N=C(S2)NC(C)C2CN(CC2)C#N)C=C1 UOADHNIYFIKIMN-UHFFFAOYSA-N 0.000 claims 1
- JZUUVVQTEQTTBW-UHFFFAOYSA-N 3-[[(3-phenylpyridin-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C(=NC=CC=1)NCC1CN(CC1)C#N JZUUVVQTEQTTBW-UHFFFAOYSA-N 0.000 claims 1
- FOFOVGZDYKHDMB-UHFFFAOYSA-N 3-[[(4-phenylpyridin-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC(=NC=C1)NCC1CN(CC1)C#N FOFOVGZDYKHDMB-UHFFFAOYSA-N 0.000 claims 1
- CZPJNEFJNYKUES-UHFFFAOYSA-N 3-[[(4-phenylpyrimidin-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NC(=NC=C1)NCC1CN(CC1)C#N CZPJNEFJNYKUES-UHFFFAOYSA-N 0.000 claims 1
- LARDRORDJPWVJU-UHFFFAOYSA-N 3-[[(6-fluoro-1,3-benzothiazol-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound FC1=CC2=C(N=C(S2)NCC2CN(CC2)C#N)C=C1 LARDRORDJPWVJU-UHFFFAOYSA-N 0.000 claims 1
- BONIFODIXPLUFS-UHFFFAOYSA-N 3-[[3-(1,3-dimethylpyrazol-4-yl)anilino]methyl]pyrrolidine-1-carbonitrile Chemical compound CN1N=C(C(=C1)C=1C=C(C=CC=1)NCC1CN(CC1)C#N)C BONIFODIXPLUFS-UHFFFAOYSA-N 0.000 claims 1
- KUWMGOCZBMTZLF-UHFFFAOYSA-N 3-[[4-(1,3-dimethylpyrazol-4-yl)-2-fluoroanilino]methyl]pyrrolidine-1-carbonitrile Chemical compound CN1N=C(C(=C1)C1=CC(=C(C=C1)NCC1CN(CC1)C#N)F)C KUWMGOCZBMTZLF-UHFFFAOYSA-N 0.000 claims 1
- XMWFANXRRULTGY-UHFFFAOYSA-N 3-[[4-(1,3-dimethylpyrazol-4-yl)anilino]methyl]pyrrolidine-1-carbonitrile Chemical compound CN1N=C(C(=C1)C1=CC=C(C=C1)NCC1CN(CC1)C#N)C XMWFANXRRULTGY-UHFFFAOYSA-N 0.000 claims 1
- RRIKZZZOBXOTDM-UHFFFAOYSA-N 3-[[[2-(1,3-dihydroisoindol-2-yl)pyridin-4-yl]amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1N(CC2=CC=CC=C12)C1=NC=CC(=C1)NCC1CN(CC1)C#N RRIKZZZOBXOTDM-UHFFFAOYSA-N 0.000 claims 1
- VJVXZMAKWGNQQY-UHFFFAOYSA-N 3-[[[6-(1H-pyrazol-4-yl)-1,3-benzothiazol-2-yl]amino]methyl]pyrrolidine-1-carbonitrile Chemical compound N1N=CC(=C1)C1=CC2=C(N=C(S2)NCC2CN(CC2)C#N)C=C1 VJVXZMAKWGNQQY-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- QNYCWDMDRKCZIS-GFCCVEGCSA-N 5-(3-cyanophenyl)-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1,3,4-oxadiazole-2-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)C1=NN=C(O1)C(=O)NC[C@@H]1CN(CC1)C#N QNYCWDMDRKCZIS-GFCCVEGCSA-N 0.000 claims 1
- QNYCWDMDRKCZIS-LBPRGKRZSA-N 5-(3-cyanophenyl)-N-[[(3S)-1-cyanopyrrolidin-3-yl]methyl]-1,3,4-oxadiazole-2-carboxamide Chemical compound O=C(NC[C@@H]1CCN(C1)C#N)C1=NN=C(O1)C1=CC(=CC=C1)C#N QNYCWDMDRKCZIS-LBPRGKRZSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- FVJOTUZVSOJFAZ-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-2-phenyl-1,3-oxazole-5-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C1=CN=C(O1)C1=CC=CC=C1 FVJOTUZVSOJFAZ-UHFFFAOYSA-N 0.000 claims 1
- SYQCTYIQOGDDGP-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-2-phenyl-1,3-thiazole-4-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C=1N=C(SC=1)C1=CC=CC=C1 SYQCTYIQOGDDGP-UHFFFAOYSA-N 0.000 claims 1
- ODNGJGWYCUPHDI-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-3-(2-fluorophenyl)-1H-pyrazole-5-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C1=CC(=NN1)C1=C(C=CC=C1)F ODNGJGWYCUPHDI-UHFFFAOYSA-N 0.000 claims 1
- YADVBEWRFDVFJO-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-3-(2-methylphenyl)-1H-pyrazole-5-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C1=CC(=NN1)C1=C(C=CC=C1)C YADVBEWRFDVFJO-UHFFFAOYSA-N 0.000 claims 1
- INMAXULWSCWODX-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-3-phenyl-1,2-oxazole-5-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C1=CC(=NO1)C1=CC=CC=C1 INMAXULWSCWODX-UHFFFAOYSA-N 0.000 claims 1
- ICGHGMIENXBPDK-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-3-phenyl-1H-pyrazole-5-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C1=NNC(=C1)C1=CC=CC=C1 ICGHGMIENXBPDK-UHFFFAOYSA-N 0.000 claims 1
- XSXXCNSCJZUFFB-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-4-[5-(trifluoromethyl)pyridin-2-yl]oxybenzenesulfonamide Chemical compound FC(F)(F)c1ccc(Oc2ccc(cc2)S(=O)(=O)NCC2CCN(C2)C#N)nc1 XSXXCNSCJZUFFB-UHFFFAOYSA-N 0.000 claims 1
- QYDVNMCMIBEURQ-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-4-methyl-3-oxo-1,4-benzoxazine-6-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C1=CC2=C(OCC(N2C)=O)C=C1 QYDVNMCMIBEURQ-UHFFFAOYSA-N 0.000 claims 1
- TXVLWXPZJTWCGI-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-4-pyridin-4-ylbenzamide Chemical compound C(#N)N1CC(CC1)CNC(C1=CC=C(C=C1)C1=CC=NC=C1)=O TXVLWXPZJTWCGI-UHFFFAOYSA-N 0.000 claims 1
- IHMFMCZUAYSYLG-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-4-pyrrolidin-1-ylpyridine-2-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(C1=NC=CC(=C1)N1CCCC1)=O IHMFMCZUAYSYLG-UHFFFAOYSA-N 0.000 claims 1
- UJSOQMOYAGSTKL-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-5-(4-fluorophenyl)pyridine-3-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(C1=CN=CC(=C1)C1=CC=C(C=C1)F)=O UJSOQMOYAGSTKL-UHFFFAOYSA-N 0.000 claims 1
- WNAHDZPGZVLNKT-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-5-phenyl-1,3-oxazole-2-carboxamide Chemical compound C(#N)N1CC(CC1)CNC(=O)C=1OC(=CN=1)C1=CC=CC=C1 WNAHDZPGZVLNKT-UHFFFAOYSA-N 0.000 claims 1
- IJTIBKOLPGKNJJ-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-N-methyl-2-(4-phenylphenyl)acetamide Chemical compound C1(=CC=C(C=C1)CC(=O)N(C)CC1CN(CC1)C#N)C1=CC=CC=C1 IJTIBKOLPGKNJJ-UHFFFAOYSA-N 0.000 claims 1
- VTSBHEBQFJJENU-UHFFFAOYSA-N N-[(1-cyanopyrrolidin-3-yl)methyl]-N-methyl-3-(2-methyl-1,3-thiazol-4-yl)benzenesulfonamide Chemical compound C(#N)N1CC(CC1)CN(S(=O)(=O)C1=CC(=CC=C1)C=1N=C(SC=1)C)C VTSBHEBQFJJENU-UHFFFAOYSA-N 0.000 claims 1
- BKHZFTFJDYOETK-CYBMUJFWSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1-(2-methoxyphenyl)imidazole-4-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1N=CN(C=1)C1=C(C=CC=C1)OC BKHZFTFJDYOETK-CYBMUJFWSA-N 0.000 claims 1
- MIIUXEYSUBINKP-CYBMUJFWSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1-(3-methoxyphenyl)imidazole-4-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1N=CN(C=1)C1=CC(=CC=C1)OC MIIUXEYSUBINKP-CYBMUJFWSA-N 0.000 claims 1
- ZMYDRZWNHZKCMN-GFCCVEGCSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1-(cyclopropylmethyl)imidazole-4-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1N=CN(C=1)CC1CC1 ZMYDRZWNHZKCMN-GFCCVEGCSA-N 0.000 claims 1
- YYDACHPLTYKYGE-CYBMUJFWSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1-phenylimidazole-4-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1N=CN(C=1)C1=CC=CC=C1 YYDACHPLTYKYGE-CYBMUJFWSA-N 0.000 claims 1
- XTUZBRUXFUDTMK-CYBMUJFWSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1-phenylpyrazole-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C1=NN(C=C1)C1=CC=CC=C1 XTUZBRUXFUDTMK-CYBMUJFWSA-N 0.000 claims 1
- ALQSOZZAXIRFNS-SNVBAGLBSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1H-benzimidazole-2-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C1=NC2=C(N1)C=CC=C2 ALQSOZZAXIRFNS-SNVBAGLBSA-N 0.000 claims 1
- ZDVWDVSXNULHLW-GFCCVEGCSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-2-phenyl-1H-imidazole-5-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C1=CN=C(N1)C1=CC=CC=C1 ZDVWDVSXNULHLW-GFCCVEGCSA-N 0.000 claims 1
- WXEFVGNMFMNWIM-GFCCVEGCSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-4-phenyl-1,3-thiazole-2-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1SC=C(N=1)C1=CC=CC=C1 WXEFVGNMFMNWIM-GFCCVEGCSA-N 0.000 claims 1
- NGPOEDGDLYCPHF-CQSZACIVSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-4-phenylpyridine-2-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(C1=NC=CC(=C1)C1=CC=CC=C1)=O NGPOEDGDLYCPHF-CQSZACIVSA-N 0.000 claims 1
- WZQZWLZAOZXBGK-GFCCVEGCSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-5-phenyl-1,2-oxazole-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C1=NOC(=C1)C1=CC=CC=C1 WZQZWLZAOZXBGK-GFCCVEGCSA-N 0.000 claims 1
- NXWSDHWYAPPKQT-GFCCVEGCSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-5-phenyl-1,3-thiazole-2-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1SC(=CN=1)C1=CC=CC=C1 NXWSDHWYAPPKQT-GFCCVEGCSA-N 0.000 claims 1
- LJLVDKFFRRWCNQ-CQSZACIVSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-5-phenylpyridine-2-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(C1=NC=C(C=C1)C1=CC=CC=C1)=O LJLVDKFFRRWCNQ-CQSZACIVSA-N 0.000 claims 1
- ARRJGAKIYIHNTR-GFCCVEGCSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-7-cyclopropylimidazo[1,2-a]pyridine-2-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1N=C2N(C=CC(=C2)C2CC2)C=1 ARRJGAKIYIHNTR-GFCCVEGCSA-N 0.000 claims 1
- WGISYTVANPICRV-GFCCVEGCSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]isoquinoline-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C=1N=CC2=CC=CC=C2C=1 WGISYTVANPICRV-GFCCVEGCSA-N 0.000 claims 1
- RUXMZIXKJFUCQK-LLVKDONJSA-N N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]pyrazolo[1,5-a]pyridine-2-carboxamide Chemical compound C(#N)N1C[C@H](CC1)CNC(=O)C1=NN2C(C=CC=C2)=C1 RUXMZIXKJFUCQK-LLVKDONJSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
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- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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Claims (113)
1. Соединение формулы (I):
или его фармацевтически приемлемая соль, где:
каждый из R1b, R1c, R1d, R1e независимо представляет собой водород или возможно замещенный C1-С6алкил, или R1b связан с R1a или R1c с образованием возможно замещенного циклоалкильного кольца, или R1e связан с R1d или R1f с образованием возможно замещенного циклоалкильного кольца;
каждый из R1a и R1g независимо представляет собой водород, фтор, циано, гидроксил, амино, возможно замещенный C1-С6алкил или возможно замещенный C1-С6алкокси, или R1a и R1g вместе образуют возможно замещенное циклоалкильное кольцо, или R1a связан с R1b с образованием возможно замещенного циклоалкильного кольца, или R1g связан с R1f с образованием возможно замещенного циклоалкильного кольца;
R1f представляет собой водород, фтор, циано, гидроксил, амино, возможно замещенный C1-С6алкил, возможно замещенный C1-С6алкокси, или R1f связан с R1g или R1e с образованием возможно замещенного циклоалкильного кольца, или R вместе с R2 образует возможно дополнительно замещенное гетероциклическое кольцо;
R2 представляет собой водород, возможно замещенный C1-С6алкил, или R2 вместе с R1f образуют возможно дополнительно замещенное гетероциклическое кольцо;
X представляет собой C(R3)(R4), где каждый из R3 и R4 независимо представляет собой водород, циано, возможно замещенный C1-С6алкил, 5 или 6-членное гетероарильное или арильное кольцо, или R3 и R4 вместе образуют 3-6-членное гетероалкильное или циклоалкильное кольцо;
L представляет собой ковалентную связь, -SO-, -SO2-, -С(О)-, -С(O)O-, -CONR5-, -SO2NR5-, -С(O)-С1-С6алкилен, -С(O)-С2-С6алкенилен, С1-С6алкилен-С(O)-, С2-С6алкенилен-С(O)-, -C1-C6aлкилeн-NR5CO-, -C1-C6алкилен-CONR5-, возможно замещенный C1-С6алкилен или возможно замещенный -С2-С6алкенилен;
А представляет собой замещенное моноциклическое гетероарильное или арильное кольцо или возможно замещенное бициклическое гетероарильное или арильное кольцо;
R5 представляет собой водород или возможно замещенный C1-С6алкил.
2. Соединение по п. 1, где кольцо А представляет собой 5-10-членное кольцо, выбранное из оксазолила, изоксазолила, пиразолила, тиазолила, пиридинила, хинолинила, бензотиазолила, изохинолинила, пиримидинила, фенила, бензоморфолинила, индазолила, имидазопиридинила, хиназолинила, пиразолопиридинила, бензимидазолила, имидазолила и оксадиазолила.
3. Соединение по любому из пп. 1-2, где кольцо А замещенно одной или более чем одной группой -Q1-(R6)n, где в каждом случае группы -Q1-(R6)n являются одинаковым или различными, где:
n представляет собой 0 или 1;
Q1 представляет собой галоген, циано, оксо, нитро, -OR7, -SR7, -NR7R8, -CONR7R8, -NR7COR8, -NR7CONR8R9, -COR7, -C(O)OR7, -SO2R7, -SO2NR7R8, -NR7SO2R8, NR7SO2NR8R9, -NR7C(O)OR8, возможно замещенный -С1-С6алкил, возможно замещенный -C1-С6алкокси, возможно замещенный -С2-С6алкенил, возможно замещенный -С2-С6алкинил, ковалентную связь, атом кислорода, атом серы, -SO-, -SO2-, -С(О)-, -С(O)O-, -CONR7-, -NR7-, -NR7CO-, -NR7CONR8-, -SO2NR7-, -NR7SO2-, -NR7SO2NR8-, -NR7C(O)O-, -NR7C(O)OR8-, возможно замещенный C1-С6алкилен или возможно замещенный -С2-С6алкенилен;
R6 представляет собой возможно замещенное 3-10-членное кольцо;
каждый из R7, R8 и R9 независимо представляет собой водород, возможно замещенный C1-С6алкил или возможно замещенный C1-С6алкилен.
4. Соединение по п. 3, где R6 представляет собой 3-10-членное гетероциклическое, циклоалкильное, арильное или гетероарильное кольцо, выбранное из фенила, тиазолила, пиридинила, пирролидинила, пиразолила, изоиндолила, изоксазолила и циклопропила.
5. Соединение по п. 3 или 4, где R6 замещен одним или более заместителями, выбранными из галогена, циано, оксо, нитро, -OR10, -SR10, -NR10R11, -CONR10R11, -NR10COR11, -NR10CONR11R12, -COR10, -C(O)OR10, -SO2R10, -SO2NR10R11, -NR10SO2R11, NR10SO2NR11R12, -NR10C(O)OR11, возможно замещенного -С1-С6алкила, возможно замещенного -C1-С6алкокси, возможно замещенного -С2-С6алкенила, возможно замещенного -С2-С6алкинила, групп -Q2-R10, -Q2-NR10CONR11R12, -Q2-NR10R11, -Q2-COR10, -Q2-NR10COR11, -Q2-NR10C(O)OR11, -Q2-SO2R10, Q2-CONR10R11, -Q2-CO2R10, -Q2-SO2NR10R11, -Q2-NR10SO2R11 и -Q2-NR10SO2NR11R12;
Q2 представляет собой ковалентную связь, атом кислорода, атом серы, -SO-, -SO2-, -СО-, возможно замещенный C1-С6алкилен или возможно замещенный С2-С6алкенилен; и
каждый из R10, R11, R12 независимо представляет собой водород, возможно замещенный C1-С6алкил, возможно замещенный гетероциклил, возможно замещенный гетероарил, возможно замещенный арил или возможно замещенный циклоалкил.
6. Соединение по п. 5, где R6 замещен галогеном, циано, С1-С4алкилом, С1-С4алкокси, где указанные алкил и алкокси возможно замещены одним или более фтором.
7. Соединение по любому из пп. 1-6, где R2 представляет собой водород или метил.
8. Соединение по любому из пп. 1-7, где каждый из C1-С6алкила, С1-С6алкокси, С2-С6алкенила, С2-С6алкинила, C1-С6алкилена, С2-С6алкенилена независимо возможно замещен одним или более заместителями, выбранными из галогена, гидроксила, тиола, циано, амино, нитро и SF5.
9. Соединение по любому из пп. 1-8, где каждый из R1a, R1b, R1c, R1d, R1e, R1f и R1g представляет собой водород.
10. Соединение формулы (I) по п. 1, выбранное из группы, состоящей из:
3-((хинолин-2-иламино)метил)пирролидин-1-карбонитрила,
3-(((6-фторбензо[d]тиазол-2-ил)амино)метил)пирролидин-1-карбонитрила,
3-((изохинолин-1-иламино)метил)пирролидин-1-карбонитрила,
3-(((3-фенилпиридин-2-ил)амино)метил)пирролидин-1-карбонитрила,
3-(((4-фенилпиридин-2-ил)амино)метил)пирролидин-1-карбонитрила,
3-(((5-фенилпиридин-2-ил)амино)метил)пиррол идин-1-карбонитрила,
3-(((6-фенилпиридин-2-ил)амино)метил)пиррол идин-1-карбонитрила,
3-(((4-фенилпиримидин-2-ил)амино)метил)пирролидин-1-карбонитрила,
(R)-3-(((5-фенилтиазол-2-ил)амино)метил)пирролидин-1-карбонитрила,
(S)-3-(((5-фенилтиазол-2-ил)амино)метил)пирролидин-1-карбонитрила,
3-(((6-(1Н-пиразол-4-ил)бензо[d]тиазол-2-ил)амино)метил)пирролидин-1-карбонитрила,
(R)-3-(((7-(1Н-пиразол-4-ил)хиназолин-2-ил)амино)метил)пирролидин-1-карбонитрила,
3-(((3-(1,3-диметил-1Н-пиразол-4-ил)фенил)амино)метил)пирролидин-1-карбонитрила,
3-(((4-(1,3-диметил-1Н-пиразол-4-ил)фенил)амино)метил)пирролидин-1-карбонитрила,
3-(((4-(1,3-диметил-1Н-пиразол-4-ил)-2-фторфенил)амино)метил)пирролидин-1-карбонитрила,
3-(((1-цианопирролидин-3-ил)метил)амино)изохинолин-6-карбонитрила,
3-(((1-цианопирролидин-3-ил)метил)амино)-N-метилизохинолин-6-карбоксамида,
3-(((2-(изоиндолин-2-ил)пиридин-4-ил)амино)метил)пирролидин-1-карбонитрила,
(S)-3-(((4-фенилпиримидин-2-ил)амино)метил)пирролидин-1-карбонитрила,
N-((1-цианопирролидин-3-ил)метил)-2-фенилоксазол-5-карбоксамида,
N-((1-цианопирролидин-3-ил)метил)-3-фенилизоксазол-5-карбоксамида,
N-((1-цианопирролидин-3-ил)метил)-5-фенил-1Н-пиразол-3-карбоксамида,
N-((1-цианопирролидин-3-ил)метил)-4-метил-3-оксо-3,4-дигидро-2Н-бензо[b][1,4]оксазин-6-карбоксамида,
N-((1-цианопирролидин-3-ил)метил)-4-(пиридин-4-ил)бензамида,
N-((1-цианопирролидин-3-ил)метил)-3-(о-толил)-1Н-пиразол-5-карбоксамида,
N-((1-цианопирролидин-3-ил)метил)-2-фенилтиазол-4-карбоксамида,
N-((1-цианопирролидин-3-ил)метил)-4-(пирролидин-1-ил)пиколинамида,
N-((1-цианопирролидин-3-ил)метил)-1-(2,4-дихлорбензил)-1Н-индазол-3-карбоксамида,
1-бензил-N-((1-цианопирролидин-3-ил)метил)-1Н-индазол-3-карбоксамида,
N-((1-циaнoпиppoлидин-3-ил)мeтил)-4-(N-фeнилcyльфaмoил)бeнзaмидa,
N-((1-цианопирролидин-3-ил)метил)-3-(2-фторфенил)-1Н-пиразол-5-карбоксамида,
(Е)-N-((1-цианопирролидин-3-ил)метил)-3-(2-фтор-4-метоксифенил)акриламида,
N-((1-цианопирролидин-3-ил)метил)-5-(4-фторфенил)никотинамида,
(S)-N-((1-цианопирролидин-3-ил)метил)-3-оксо-3,4-дигидро-2Н-бензо[b][1,4]оксазин-6-карбоксамида,
(R)-6-хлор-N-((1-цианопирролидин-3-ил)метил)имидазо[1,2-а]пиридин-2-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)пиразоло[1,5-а]пиридин-2-карбоксамида,
2-([1,1'-бифенил]-4-ил)-N-((1-цианопирролидин-3-ил)метил)-N-метилацетамида,
N-((1-цианопирролидин-3-ил)метил)-5-фенилоксазол-2-карбоксамида,
N-((1-циaнoпиppoлидин-3-ил)мeтил)-6-(1-мeтил-1H-пиpaзoл-4-ил)имидaзo[1,2-a]пиpидин-2-карбоксамида,
1-бензил-N-((1-цианопирролидин-3-ил)метил)-5-метил-1Н-пиразол-3-карбоксамида,
1-(3-хлорфенил)-3-((1-цианопирролидин-3-ил)метил)мочевины,
1-((1-цианопирролидин-3-ил)метил)-3-(2-фтор-5-метилфенил)мочевины,
1-(3-бензилфенил)-3-((1-цианопирролидин-3-ил)метил)мочевины,
1-((1-цианопирролидин-3-ил)метил)-3-(2,4-дихлорфенил)мочевины,
1-((1-цианопирролидин-3-ил)метил)-3-(4-(трифторметил)фенил)мочевины,
N-((1-цианопирролидин-3-ил)метил)-N-метил-3-(2-метилтиазол-4-ил)бензолсульфонамида,
N-((1-цианопирролидин-3-ил)метил)-N-метил-4-((5-(трифторметил)пиридин-2-ил)окси)бензолсульфонамида,
3-(1-((6-(5-метилизоксазол-4-ил)бензо[d]тиазол-2-ил)амино)этил)пирролидин-1-карбонитрила,
3-(1-((6-(1Н-пиразол-4-ил)бензо[d]тиазол-2-ил)амино)этил)пирролидин-1-карбонитрила,
3-(1-(изохинолин-3-иламино)этил)пирролидин-1-карбонитрила,
3-((1-(1-цианопирролидин-3-ил)этил)амино)изохинолин-6-карбонитрила,
3-((бензо[d]тиазол-2-иламино)(циано)метил)пирролидин-1-карбонитрила,
2-((1-(1-цианопирролидин-3-ил)этил)амино)бензо[d]тиазол-6-карбонитрила,
(3аR,6аS)-4-оксо-5-(5-фенилтиазол-2-ил)гексагидропирроло[3,4-с]пиррол-2(1Н)-карбонитрила,
(R)-3-(3-хлорфенил)-Н-((1-цианопирролидин-3-ил)метил)изоксазол-5-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-1Н-бензо[d]имидазол-2-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)изохинолин-3-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-5-фенилизоксазол-3-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-4-фенилпиколинамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-5-фенилпиколинамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-5-фенилтиазол-2-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-4-фенилтиазол-2-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-1-фенил-1H-пиразол-3-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-2-фенил-1Н-имидазол-5-карбоксамида,
(R)-7-хлор-N-((1-цианопирролидин-3-ил)метил)имидазо[1,2-а]пиридин-2-карбоксамида,
(R)-3-(2-хлорфенил)-N-((1-цианопирролидин-3-ил)метил)изоксазол-5-карбоксамида,
(R)-3-(4-хлорфенил)-N-((1-цианопирролидин-3-ил)метил)изоксазол-5-карбоксамида,
(R)-5-(3-цианофенил)-N-((1-цианопирролидин-3-ил)метил)-1,3,4-оксадиазол-2-карбоксамида,
(S)-5-(3-цианофенил)-N-((1-цианопирролидин-3-ил)метил)-1,3,4-оксадиазол-2-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-1-фенил-1Н-имидазол-4-карбоксамида,
(R)-1-(3-цианофенил)-N-((1-цианопирролидин-3-ил)метил)-1Н-имидазол-4-карбоксамида,
(R)-1-(4-цианофенил)-N-((1-цианопирролидин-3-ил)метил)-1Н-имидазол-4-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-1-(2-метоксифенил)-1Н-имидазол-4-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-1-(3-метоксифенил)-1Н-имидазол-4-карбоксамида,
(R)-N-((1-циaнoпиppoлидин-3-ил)мeтил)-6-(1H-пиpaзoл-4-ил)имидaзo[1,2-a]пиpидин-2-карбоксамида,
(R)-N-((1-циaнoпиppoлидин-3-ил)мeтил)-6-(1H-пиpaзoл-3-ил)имидaзo[1,2-a]пиpидин-2-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-7-циклопропилимидазо[1,2-а]пиридин-2-карбоксамида,
(R)-1-бензил-N-((1-цианопирролидин-3-ил)метил)-1Н-имидазол-4-карбоксамида,
(R)-N-((1-цианопирролидин-3-ил)метил)-1-(циклопропилметил)-1Н-имидазол-4-карбоксамида,
или его фармацевтически приемлемые соли.
11. Способ получения соединения формулы (I) или его фармацевтически приемлемой соли по п. 1, включающий стадии приведения во взаимодействие амина формулы (V) с бромцианом:
где R1a, R1b, R1c, R1d, R1e, R1f, R1g, R2, кольцо A, L и X такие, как определено в п. 1.
12. Соединение по любому из пп. 1-10 для применения в лечении состояния, связанного с митохондриальной дисфункцией.
13. Соединение для применения по п. 12, где состояние, связанное с митохондриальной дисфункцией, представляет собой расстройство центральной нервной системы.
14. Соединение по любому из пп. 1-10 для применения в лечении рака.
15. Фармацевтическая композиция, содержащая соединение по любому из пп. 1-10 вместе с одним или более чем одним фармацевтически приемлемым эксципиентом.
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IL298710A (en) * | 2020-06-04 | 2023-02-01 | Mission Therapeutics Ltd | N-cyanopyrrolidines with activity as usp30 inhibitors |
AU2021286831A1 (en) | 2020-06-08 | 2023-02-02 | Mission Therapeutics Limited | 1-(5-(2-cyanopyridin-4-yl)oxazole-2-carbonyl)-4- methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carbonitrile as USP30 inhibitor for use in the treatment of mitochondrial dysfunction, cancer and fibrosis |
GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
JP2024544660A (ja) | 2021-12-01 | 2024-12-03 | ミッション セラピューティクス リミティド | Usp30阻害剤としての活性を有する置換n-シアノピロリジン |
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WO2001077073A1 (en) * | 2000-04-06 | 2001-10-18 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
MX2009010491A (es) * | 2007-04-11 | 2009-11-09 | Kissei Pharmaceutical | Derivado heterociclico de 5 miembros y su uso para propositos medicos. |
EP2565186A1 (en) * | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
US9963444B2 (en) | 2014-05-19 | 2018-05-08 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (NAAA) inhibitors and their use thereof |
GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
BR112017020900B1 (pt) | 2015-03-30 | 2023-02-23 | Mission Therapeutics Limited | Compostos de 1-ciano-pirrolidina como inibidores de usp30 e seu uso, composição farmacêutica |
US10669234B2 (en) | 2015-07-14 | 2020-06-02 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
GB201521109D0 (en) | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
GB201522267D0 (en) * | 2015-12-17 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
GB201522768D0 (en) | 2015-12-23 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
GB201602854D0 (en) * | 2016-02-18 | 2016-04-06 | Mission Therapeutics Ltd | Novel compounds |
GB201603779D0 (en) | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
MA43753A (fr) | 2016-03-24 | 2018-11-28 | Mission Therapeutics Ltd | Dérivés 1-cyano-pyrrolidine comme inhibiteurs de dbu |
ES2850349T3 (es) | 2016-09-27 | 2021-08-27 | Mission Therapeutics Ltd | Derivados de cianopirrolidina con actividad como inhibidores de USP30 |
GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
GB201616627D0 (en) | 2016-09-30 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
US11059809B2 (en) * | 2017-06-20 | 2021-07-13 | Mission Therapeutics Limited | Substituted cyanopyrrolidines with activity as DUB inhibitors |
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