HRP20200962T1 - Novi spojevi - Google Patents
Novi spojevi Download PDFInfo
- Publication number
- HRP20200962T1 HRP20200962T1 HRP20200962TT HRP20200962T HRP20200962T1 HR P20200962 T1 HRP20200962 T1 HR P20200962T1 HR P20200962T T HRP20200962T T HR P20200962TT HR P20200962 T HRP20200962 T HR P20200962T HR P20200962 T1 HRP20200962 T1 HR P20200962T1
- Authority
- HR
- Croatia
- Prior art keywords
- carboxamide
- cyano
- pyrrolidine
- thiazol
- imidazol
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 25
- -1 deutero Chemical group 0.000 claims 25
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- PEFCHYKDOSEHDB-NSHDSACASA-N C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)C=1C=NC=CC=1 Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)C=1C=NC=CC=1 PEFCHYKDOSEHDB-NSHDSACASA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- MVRYYMDCBUBSGA-JTQLQIEISA-N O=C(NC1=NN2C=CC=CC2=C1)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NN2C=CC=CC2=C1)[C@H]1CCN(C1)C#N MVRYYMDCBUBSGA-JTQLQIEISA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000006323 alkenyl amino group Chemical group 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- JWPYAJITXMNTCJ-JSGCOSHPSA-N (2S,3S)-1-cyano-2-methyl-N-(1-phenylimidazol-4-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC=CC=C1)C JWPYAJITXMNTCJ-JSGCOSHPSA-N 0.000 claims 1
- ZAAXLBBCCFHMOE-AAEUAGOBSA-N (2S,3S)-1-cyano-2-methyl-N-(5-phenyl-1,3-thiazol-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1SC(=CN=1)C1=CC=CC=C1)C ZAAXLBBCCFHMOE-AAEUAGOBSA-N 0.000 claims 1
- ZFKROPSBIISOEE-DZKIICNBSA-N (2S,3S)-1-cyano-2-methyl-N-[1-[(1S)-1-phenylethyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1N=CN(C=1)[C@@H](C)C1=CC=CC=C1)C ZFKROPSBIISOEE-DZKIICNBSA-N 0.000 claims 1
- HNRKXHFKZRSJOY-JQWIXIFHSA-N (2S,3S)-1-cyano-2-methyl-N-[5-(oxan-4-yl)-1,3-thiazol-2-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1SC(=CN=1)C1CCOCC1)C HNRKXHFKZRSJOY-JQWIXIFHSA-N 0.000 claims 1
- VKZXJUBADCMWAN-LRDDRELGSA-N (2S,3S)-1-cyano-N-(6-ethynylisoquinolin-3-yl)-2-methylpyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1N=CC2=CC=C(C=C2C=1)C#C)C VKZXJUBADCMWAN-LRDDRELGSA-N 0.000 claims 1
- GTXJCUXQYGCWEV-GWCFXTLKSA-N (2S,3S)-1-cyano-N-[5-(4-fluorophenyl)-1,3-thiazol-2-yl]-2-methylpyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1SC(=CN=1)C1=CC=C(C=C1)F)C GTXJCUXQYGCWEV-GWCFXTLKSA-N 0.000 claims 1
- CGNVTUFYDMIHFF-GUTXKFCHSA-N (2S,3S)-1-cyano-N-[5-[[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]-1,3-thiazol-2-yl]-2-methylpyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1SC(=CN=1)CN1[C@H](CCC1)COC)C CGNVTUFYDMIHFF-GUTXKFCHSA-N 0.000 claims 1
- JKIARXUZVJRKQO-FZMZJTMJSA-N (2S,3S)-1-cyano-N-[6-(3,5-dimethyl-1,2-oxazol-4-yl)-1,3-benzothiazol-2-yl]-2-methylpyrrolidine-3-carboxamide Chemical compound C(#N)N1[C@H]([C@H](CC1)C(=O)NC=1SC2=C(N=1)C=CC(=C2)C=1C(=NOC=1C)C)C JKIARXUZVJRKQO-FZMZJTMJSA-N 0.000 claims 1
- ADYYUJAQFPJRKX-LLVKDONJSA-N (3R)-1-cyano-N-(5-piperidin-1-yl-1,3-thiazol-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)C(=O)NC=1SC(=CN=1)N1CCCCC1 ADYYUJAQFPJRKX-LLVKDONJSA-N 0.000 claims 1
- TVBNULGJUGAFLS-ZDUSSCGKSA-N (3S)-1-cyano-N-(1-methyl-5-phenylpyrazol-3-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC1=NN(C(=C1)C1=CC=CC=C1)C TVBNULGJUGAFLS-ZDUSSCGKSA-N 0.000 claims 1
- GRMFCQJABOTFOD-LBPRGKRZSA-N (3S)-1-cyano-N-(1-phenylpyrazol-3-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC1=NN(C=C1)C1=CC=CC=C1 GRMFCQJABOTFOD-LBPRGKRZSA-N 0.000 claims 1
- HISADVKXSOJWQN-NSHDSACASA-N (3S)-1-cyano-N-(1-phenyltriazol-4-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=NN(C=1)C1=CC=CC=C1 HISADVKXSOJWQN-NSHDSACASA-N 0.000 claims 1
- VEHXXPUZDSRWPD-NSHDSACASA-N (3S)-1-cyano-N-(1-pyridin-4-ylimidazol-4-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC=NC=C1 VEHXXPUZDSRWPD-NSHDSACASA-N 0.000 claims 1
- BCVKVNZCOIGJHF-ZDUSSCGKSA-N (3S)-1-cyano-N-(1-quinolin-4-ylimidazol-4-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC=NC2=CC=CC=C12 BCVKVNZCOIGJHF-ZDUSSCGKSA-N 0.000 claims 1
- JXDMUQABKUQTRY-LBPRGKRZSA-N (3S)-1-cyano-N-(4-pyrrolidin-1-ylpyridin-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC1=NC=CC(=C1)N1CCCC1 JXDMUQABKUQTRY-LBPRGKRZSA-N 0.000 claims 1
- ONIHSXKWNFYNNS-JTQLQIEISA-N (3S)-1-cyano-N-(5-morpholin-4-yl-1,3-thiazol-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)N1CCOCC1 ONIHSXKWNFYNNS-JTQLQIEISA-N 0.000 claims 1
- ADYYUJAQFPJRKX-NSHDSACASA-N (3S)-1-cyano-N-(5-piperidin-1-yl-1,3-thiazol-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)N1CCCCC1 ADYYUJAQFPJRKX-NSHDSACASA-N 0.000 claims 1
- FQDMRJSSBCLPBF-NSHDSACASA-N (3S)-1-cyano-N-(5-pyrrolidin-1-ylpyrazin-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC1=NC=C(N=C1)N1CCCC1 FQDMRJSSBCLPBF-NSHDSACASA-N 0.000 claims 1
- QHRIRBKMJFOPAT-LBPRGKRZSA-N (3S)-1-cyano-N-(6-propan-2-ylsulfonyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC2=C(CCN(CC2)S(=O)(=O)C(C)C)N=1 QHRIRBKMJFOPAT-LBPRGKRZSA-N 0.000 claims 1
- VRQPLRVXJHXNPY-LBPRGKRZSA-N (3S)-1-cyano-N-(6-pyrrolidin-1-ylpyridin-2-yl)pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC1=NC(=CC=C1)N1CCCC1 VRQPLRVXJHXNPY-LBPRGKRZSA-N 0.000 claims 1
- QGRYUKDLFKWONJ-WUJWULDRSA-N (3S)-1-cyano-N-[1-(1-phenylethyl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C(C)C1=CC=CC=C1 QGRYUKDLFKWONJ-WUJWULDRSA-N 0.000 claims 1
- QAHRIGRXXQSEMT-LBAUFKAWSA-N (3S)-1-cyano-N-[1-(2,3-dihydro-1H-inden-1-yl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1CCC2=CC=CC=C12 QAHRIGRXXQSEMT-LBAUFKAWSA-N 0.000 claims 1
- UGKSAUKCEYCSBS-NSHDSACASA-N (3S)-1-cyano-N-[1-(3-fluorophenyl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC(=CC=C1)F UGKSAUKCEYCSBS-NSHDSACASA-N 0.000 claims 1
- AHRKITYWANBDTM-LBPRGKRZSA-N (3S)-1-cyano-N-[1-(3-methyl-2H-indazol-6-yl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC=C2C(=NNC2=C1)C AHRKITYWANBDTM-LBPRGKRZSA-N 0.000 claims 1
- CINAXXPVGZIKTR-ZDUSSCGKSA-N (3S)-1-cyano-N-[1-(4-cyano-3-methoxyphenyl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC(=C(C=C1)C#N)OC CINAXXPVGZIKTR-ZDUSSCGKSA-N 0.000 claims 1
- IKLNBHUMPKZHFB-AWEZNQCLSA-N (3S)-1-cyano-N-[1-(4-cyano-3-methylphenyl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC(=C(C=C1)C#N)C IKLNBHUMPKZHFB-AWEZNQCLSA-N 0.000 claims 1
- CEKXKMILDLAEME-ZDUSSCGKSA-N (3S)-1-cyano-N-[1-(oxan-4-ylmethyl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)CC1CCOCC1 CEKXKMILDLAEME-ZDUSSCGKSA-N 0.000 claims 1
- OZERNCUBDVXMNL-LBPRGKRZSA-N (3S)-1-cyano-N-[1-(pyridin-2-ylmethyl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)CC1=NC=CC=C1 OZERNCUBDVXMNL-LBPRGKRZSA-N 0.000 claims 1
- WPRCPTDFQMLWIN-ZDUSSCGKSA-N (3S)-1-cyano-N-[1-(pyridin-3-ylmethyl)imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)CC=1C=NC=CC=1 WPRCPTDFQMLWIN-ZDUSSCGKSA-N 0.000 claims 1
- HLFMPNQSSDJNQI-LBPRGKRZSA-N (3S)-1-cyano-N-[1-[2-(methylcarbamoyl)phenyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=C(C=CC=C1)C(NC)=O HLFMPNQSSDJNQI-LBPRGKRZSA-N 0.000 claims 1
- QMAHQDAJVAMPOB-ZDUSSCGKSA-N (3S)-1-cyano-N-[1-[3-(methylcarbamoyl)phenyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC(=CC=C1)C(NC)=O QMAHQDAJVAMPOB-ZDUSSCGKSA-N 0.000 claims 1
- TXNQBQNMJMUZGZ-AWEZNQCLSA-N (3S)-1-cyano-N-[1-[4-(1H-pyrazol-4-yl)phenyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1C=NC(=C1)NC(=O)[C@@H]1CN(CC1)C#N TXNQBQNMJMUZGZ-AWEZNQCLSA-N 0.000 claims 1
- JCAABXZKONDOHJ-ZDUSSCGKSA-N (3S)-1-cyano-N-[1-[4-(methylcarbamoyl)phenyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC=C(C=C1)C(NC)=O JCAABXZKONDOHJ-ZDUSSCGKSA-N 0.000 claims 1
- LVBMADWAZOKRKW-KRWDZBQOSA-N (3S)-1-cyano-N-[1-[4-[1-(2-methoxyethyl)pyrazol-4-yl]phenyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC=C(C=C1)C=1C=NN(C=1)CCOC LVBMADWAZOKRKW-KRWDZBQOSA-N 0.000 claims 1
- KWCFMAUGNUJMAZ-LBPRGKRZSA-N (3S)-1-cyano-N-[1-[4-cyano-3-(trifluoromethoxy)phenyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC(=C(C=C1)C#N)OC(F)(F)F KWCFMAUGNUJMAZ-LBPRGKRZSA-N 0.000 claims 1
- XZIUGCPTDKRVIN-LBPRGKRZSA-N (3S)-1-cyano-N-[1-[4-cyano-3-(trifluoromethyl)phenyl]imidazol-4-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1N=CN(C=1)C1=CC(=C(C=C1)C#N)C(F)(F)F XZIUGCPTDKRVIN-LBPRGKRZSA-N 0.000 claims 1
- FHUCHXUCNQSNGO-AWEZNQCLSA-N (3S)-1-cyano-N-[1-methyl-5-(3-methylphenyl)pyrazol-3-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC1=NN(C(=C1)C=1C=C(C=CC=1)C)C FHUCHXUCNQSNGO-AWEZNQCLSA-N 0.000 claims 1
- WVFXHDTULFMOII-LBPRGKRZSA-N (3S)-1-cyano-N-[5-(1-methyl-2-oxopyridine-3-carbonyl)-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-2-yl]pyrrolidine-3-carboxamide Chemical compound CN1C=CC=C(C(=O)N2CCC3=C(C2)SC(NC(=O)[C@H]2CCN(C2)C#N)=N3)C1=O WVFXHDTULFMOII-LBPRGKRZSA-N 0.000 claims 1
- IVWMBQOZZQIPHT-NWDGAFQWSA-N (3S)-1-cyano-N-[5-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]-1,3-thiazol-2-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)N1[C@H](CCC1)COC IVWMBQOZZQIPHT-NWDGAFQWSA-N 0.000 claims 1
- IVWMBQOZZQIPHT-RYUDHWBXSA-N (3S)-1-cyano-N-[5-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-1,3-thiazol-2-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)N1[C@@H](CCC1)COC IVWMBQOZZQIPHT-RYUDHWBXSA-N 0.000 claims 1
- DLOJFQRZKOZSKI-QWHCGFSZSA-N (3S)-1-cyano-N-[5-[[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]-1,3-thiazol-2-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)CN1[C@H](CCC1)COC DLOJFQRZKOZSKI-QWHCGFSZSA-N 0.000 claims 1
- DLOJFQRZKOZSKI-STQMWFEESA-N (3S)-1-cyano-N-[5-[[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]-1,3-thiazol-2-yl]pyrrolidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC(=CN=1)CN1[C@@H](CCC1)COC DLOJFQRZKOZSKI-STQMWFEESA-N 0.000 claims 1
- FJOMDXXHHMDCQY-QMMMGPOBSA-N (3S)-N-(4-bromo-1,3-benzothiazol-2-yl)-1-cyanopyrrolidine-3-carboxamide Chemical compound BrC1=CC=CC2=C1N=C(S2)NC(=O)[C@@H]1CN(CC1)C#N FJOMDXXHHMDCQY-QMMMGPOBSA-N 0.000 claims 1
- JHYOQDQDNAQVDZ-NSHDSACASA-N (3S)-N-(4-tert-butylpyridin-2-yl)-1-cyanopyrrolidine-3-carboxamide Chemical compound C(C)(C)(C)C1=CC(=NC=C1)NC(=O)[C@@H]1CN(CC1)C#N JHYOQDQDNAQVDZ-NSHDSACASA-N 0.000 claims 1
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- NAMOXXGJPUXREH-AWEZNQCLSA-N O=C(NC1=NC=CC(=C1)C1=CC=CC2=NC=CN12)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NC=CC(=C1)C1=CC=CC2=NC=CN12)[C@H]1CCN(C1)C#N NAMOXXGJPUXREH-AWEZNQCLSA-N 0.000 claims 1
- IRXDFJPQOSHCPR-UHFFFAOYSA-N O=C(NC1=NC=CC(=C1)C1=CC=CC=C1)C1CCN(C1)C#N Chemical compound O=C(NC1=NC=CC(=C1)C1=CC=CC=C1)C1CCN(C1)C#N IRXDFJPQOSHCPR-UHFFFAOYSA-N 0.000 claims 1
- LNXWHMNIPHIQMY-ZDUSSCGKSA-N O=C(NC1=NC=CC(=C1)C1=CC=NC2=CC=NN12)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NC=CC(=C1)C1=CC=NC2=CC=NN12)[C@H]1CCN(C1)C#N LNXWHMNIPHIQMY-ZDUSSCGKSA-N 0.000 claims 1
- MYHFQYPWFHHTBO-ZDUSSCGKSA-N O=C(NC1=NC=CC(=C1)C1=CC=NC2=NC=CN12)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NC=CC(=C1)C1=CC=NC2=NC=CN12)[C@H]1CCN(C1)C#N MYHFQYPWFHHTBO-ZDUSSCGKSA-N 0.000 claims 1
- IKWFVWIBLLXRNA-ZDUSSCGKSA-N O=C(NC1=NC=CC(=C1)C1=CN2C=CN=C2C=N1)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NC=CC(=C1)C1=CN2C=CN=C2C=N1)[C@H]1CCN(C1)C#N IKWFVWIBLLXRNA-ZDUSSCGKSA-N 0.000 claims 1
- JEPOSCFVVCKUAX-ZDUSSCGKSA-N O=C(NC1=NC=CC(=C1)C1=CN2C=CN=C2N=C1)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NC=CC(=C1)C1=CN2C=CN=C2N=C1)[C@H]1CCN(C1)C#N JEPOSCFVVCKUAX-ZDUSSCGKSA-N 0.000 claims 1
- ULTXTBJHKQUZQC-UHFFFAOYSA-N O=C(NC1=NC=CC=C1)C1CCN(C1)C#N Chemical compound O=C(NC1=NC=CC=C1)C1CCN(C1)C#N ULTXTBJHKQUZQC-UHFFFAOYSA-N 0.000 claims 1
- VSNCQVOPJQXXFV-AWEZNQCLSA-N O=C(NC1=NN2CCN(CC2=C1)C1=CC=CC=C1)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NN2CCN(CC2=C1)C1=CC=CC=C1)[C@H]1CCN(C1)C#N VSNCQVOPJQXXFV-AWEZNQCLSA-N 0.000 claims 1
- SATJOCRUOKYVHG-INIZCTEOSA-N O=C(NC1=NN2CCN(CC3=CC=CC=C3)CC2=C1)[C@H]1CCN(C1)C#N Chemical compound O=C(NC1=NN2CCN(CC3=CC=CC=C3)CC2=C1)[C@H]1CCN(C1)C#N SATJOCRUOKYVHG-INIZCTEOSA-N 0.000 claims 1
- HOBDMDYUKBFZLF-UHFFFAOYSA-N O=C(NC1=NN=C(S1)C1=CC=CC=C1)C1CCN(C1)C#N Chemical compound O=C(NC1=NN=C(S1)C1=CC=CC=C1)C1CCN(C1)C#N HOBDMDYUKBFZLF-UHFFFAOYSA-N 0.000 claims 1
- WZGHAPPYTJKYFV-UHFFFAOYSA-N O=C(NC1=NOC(=C1)C1=CC=CC=C1)C1CCN(C1)C#N Chemical compound O=C(NC1=NOC(=C1)C1=CC=CC=C1)C1CCN(C1)C#N WZGHAPPYTJKYFV-UHFFFAOYSA-N 0.000 claims 1
- PKCWBSHISURXPU-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)NC(=O)C1CN(CC1)C#N Chemical compound S1C(=NC2=C1C=CC=C2)NC(=O)C1CN(CC1)C#N PKCWBSHISURXPU-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000005959 diazepanyl group Chemical group 0.000 claims 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- MBJVWMQHKCGMLZ-UHFFFAOYSA-N isoquinoline-6-carboxamide Chemical compound C1=NC=CC2=CC(C(=O)N)=CC=C21 MBJVWMQHKCGMLZ-UHFFFAOYSA-N 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- RFMDUDPGXBMCOU-VIFPVBQESA-N methyl 2-[[(3S)-1-cyanopyrrolidine-3-carbonyl]amino]-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate Chemical compound C(#N)N1C[C@H](CC1)C(=O)NC=1SC=2CN(CCC=2N=1)C(=O)OC RFMDUDPGXBMCOU-VIFPVBQESA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Classifications
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D513/04—Ortho-condensed systems
Claims (18)
1. Spoj formule (I)
[image]
tautomer istog, ili farmaceutski prihvatljiva sol navedenog spoja ili tautomera, naznačen time da:
R1 predstavlja 5 do 10-dijelni heteroarilni prsten;
R2, R3, R4, R5, R6 i R8, svaki zasebno, predstavljaju atom vodika, cijano, C1-C3 alkil, C1-C3 alkoksi skupine, ili R2 je povezan s R8 kako bi oblikovali C3-C4 cikloalkilni prsten, ili R6 je povezan s R7 kako bi oblikovali C3-C4 cikloalkilni prsten;
naznačen time da navedene alkil, alkoksi i cikloalkil skupine mogu opcionalno biti zamijenjene s jednim ili više supstituenata, koji mogu biti isti ili različiti, odabrani od halo, deutero, C1-3 alkil, C1-3 alkoksi, i cijano;
R7 predstavlja atom vodika, atom fluora, cijano, C1-C3 alkil, CF3, C1-C3 alkoksi skupinu ili aril ili heteroarilni prsten ili je povezan s R8 kako bi oblikovao spirocikličnu skupinu ili je povezan s R6 kako bi oblikovao C3-C4 cikloalkilni prsten;
naznačen time da R1 može opcionalno biti zamijenjen s jednim ili više od Q1-(R9)n;
n je 0 ili 1;
Q1 predstavlja atom vodika, halogeni atom, cijano, kovalentnu vezu, -NR10-, -CONR10-, -NR10CO-, atom kisika, okso, nitro, -S(O)m-, C1-C6 alkoksi, C1-C6 haloalkoksi, C1-C6 hidroksialkil, -CO-, -SO2R11, -NR11R12, -NR11COR12, -NR10CONR11R12, -CONR11R12, -CO2R11, -NR11CO2R12, -SO2NR11R12, -C(O)R11, -NR11SO2R12, NR11SO2NR13R14, i SO2NR11, C1-C6 alkilen, -C2-C6 alkenilen, -C1-C6 alkil, ili C1-C2 haloalkilnu skupinu;
m je 0, 1 ili 2;
R9 predstavlja 3 do 10-dijelni heterociklil, heteroaril, aril ili cikloalkilni prsten; i
R10, R11, i R12 svaki zasebno predstavljaju atom vodika, C1-C6 alkil, ili C1-C6 alkilensku skupinu;
naznačen time da R9 može opcionalno biti zamijenjen s jednim ili više supstituenata odabranih od halogena, C1-C6 haloalkila, C1-C6 alkoksi, C1-C6 haloalkoksi, C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, C1-C6 hidroksialkil, okso, cijano, nitro, heterociklil, cikloalkil, heteroaril, aril, -Q2-NR13CONR14R15, -Q2-NR13R14, -Q2-NR13COR14, -Q2-COR13, -Q2-SO2R13, -Q2-CONR13, Q2-CONR13R14, -Q2-CO2R13, -Q2-SO2NR13R14, -Q2-NR13SO2R14, i -Q2-NR13SO2NR14R15;
naznačen time da navedene alkil, alkoksi heteroarilne skupine mogu opcionalno biti zamijenjene s halo, deutero, C1-3 alkil, hidroksi, C1-3 alkoksi, cijano, amino, nitro, okso, aril, heteroaril, heterociklil, C3-C6 cikloalkil, C1-3 alkilamino, C2-6 alkenilamino, di-C1-3 alkilamino, C1-3 acilamino, di-C1-3 acilamino, karboksi, C1-3 alkoksikarbonil, karbamoil, mono-C1-3 karbamoil, di-C1-3 karbamoil ili bilo koji od prethodnih u kojima je hidrokarbilni dio sam zamijenjen s halo;
ili R9 može biti zamijenjen s 3 do 10-dijelnim heterociklil, heteroaril, aril ili cikloalkil prstenom, ili izravno pričvršćenim ili putem povezujuće skupine odabrane od kisika, karbonila, opcionalno zamijenjenog C1-C6 alkilena ili opcionalno zamijenjenog C1-C6 alkilenoksi lanca;
Q2 predstavlja kovalentnu vezu ili C1-C6 alkilen ili C2-C6 alkilen skupinu; i
R13, R14 i R15 svaki zasebno predstavljaju vodik, C1-C6 alkil, heterociklil, heteroaril, aril, ili cikloalkil;
naznačen time da navedena alkil skupina može opcionalno biti zamijenjena s halo, deutero, C1-3 alkil , hidroksi, C1-3 alkoksi, cijano, amino, nitro, okso, aril, heteroaril, heterociklil, C3-C6 cikloalkil, C1-3 alkilamino, C2-6 alkenilamino, di-C1-3 alkilamino, C1-3 akilamino, di-C1-3 akilamino, karboksi, C1-3 alkoksikarbonil, karbamoil, mono-C1-3 karbamoil, di-C1-3 karbamoil ili bilo koji od prethodnih u kojima je hidrokarbilni dio sam zamijenjen s halo.
2. Spoj prema zahtjevu 1, naznačen time da je R1 5 do 10-dijelni monociklični ili biciklični heteroarilni prsten koji se sastoji od 1 do 3 heteroatoma zasebno odabrana od dušika, kisika i sumpora, i koji može opcionalno biti zamijenjen s 1 do 4 Q1-(R9)n.
3. Spoj prema bilo kojem od zahtjeva 1 ili zahtjeva 2, naznačen time da je heteroarilni prsten iz R1 5 ili 6-dijelni heteroarilni prsten ili 9-dijelni biciklični heteroarilni prsten.
4. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time da je prsten iz R1 odabran od tiazolila, piridinila, izoksazolila, tiadiazolila, indazolila, imidazolila, benzotiazolila, benzoimidazolila, pirazolila, piridazinila, pirimidinila, naptiridinila, pirazinila, izokvinolinila, kvinolinila, tetrahidrotiazolopiridinila, imidazopiridinila, triazolila, pirazolopiridinila, tetrahidropirazolopirazinila, tetrahidrotiazoloazepinila i tiazolopiridinila.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time da za svaki Q1-(R9)n, gdje je n 0, svaki Q1 supstituent može biti zasebno odabran od halogenog atoma, C1-C4 alkila, C1-C2 haloalkila, C1-C2 alkoksi, -COR11, -SO2R11, cijano, CONR11R12 i C1-C2 haloalkoksi; i
naznačen time da za svaki Q1-(R9)n, gdje je n 1, svaki Q1 supstituent može biti zasebno odabran od kovalentne veze, -CO-, C1-C6 alkilena, C2-C6 alkilen skupine, i –NR10.
6. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time da R2 predstavlja vodik, cijano, metil, ili metoksi, pri čemu je metil skupina opcionalno zamijenjena s fluoro, kloro ili metoksi.
7. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time da R7 predstavlja vodik, metil, CF3, fenil, piridil, ili pirimidil.
8. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time da R2, R3, R4, R5, R6, R7 i R8 svaki zasebno predstavljaju vodik.
9. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time da R3 predstavlja metil.
10. Spoj prema bilo kojem od zahtjeva 1 do 9, naznačen time da je prsten iz R9 5 ili 6-dijelni monocikličan, ili 9 ili 10-dijelni bicikličan, heterocikličan, arilni, heteroarilni ili cikloalkilni prsten.
11. Spoj prema zahtjevu 10, naznačen time da je prsten iz R9 odabran od morfolinila, piperidnila, pirolidinila, diazepanila, piperazinila, piridazinila, pirazinila, pirazolila, ciklopropila, cikloheksila, ciklopentila, piridinila, imidazolila, indolinila, izoindolinila, pirimidinila, izoksazolila, dihidroidenila, dihidroizokvinolinila, tetrahidropiranila, fenila, oksadiazolila, triazolila, izokvinolinila, indazolila, pirazolopiridinila, pirazolopirimidinila, imidazolpiridinila, imidazopirimidinila, imidazopirazinila, oksazolila i kvinolinila.
12. Spoj prema bilo kojem od zahtjeva 1 do 11, naznačen time da:
R9 može opcionalni biti zamijenjen s jednim ili više supstituenata odabranih od halogena, C1-C6 haloalkil, C1-C6 alkoksi, C1-C6 haloalkoksi, C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, C1-C6 hidroksialkil, okso, cijano, nitro, heterociklil, cikloalkil, heteroaril, aril, -Q2-NR13CONR14R15, -Q2-NR13R14, -Q2-NR13COR14, -Q2-COR13, -Q2-SO2R13, -Q2-CONR13, Q2-CONR13R14, -Q2-CO2R13, -Q2-SO2NR13R14, -Q2-NR13SO2R14 i -Q2-NR13SO2NR14R15; pri čemu navedene alkil, alkoksi i heteroaril skupine mogu opcionalno biti zamijenjene s halo, deutero, C1-3 alkil, hidroksi, C1-3alkoksi, cijano, amino, nitro, ili okso;
ili R9 može biti zamijenjen s 3 do 10-dijelnim heterociklil, heteroaril, aril ili cikloalkil prstenom, ili izravno pričvršćenim ili putem povezujuće skupine odabrane od kisika, karbonila, opcionalno zamijenjenog C1-C6 alkilena ili opcionalno zamijenjenog C1-C6 alkilenoksi lanca;
Q2 predstavlja kovalentnu vezu ili C1-C6 alkilen ili C2-C6 alkenilen skupinu; i
R13, R14 i R15 svaki zasebno predstavljaju vodik, C1-C6 alkil, heterociklil, heteroaril, aril, ili cikloalkil;
pri čemu navedena alkilna skupina može opcionalno biti zamijenjena s halo, deutero, C1-3 alkil, hidroksi, C1-3 alkoksi, cijano, amino, nitro ili okso.
13. Spoj prema zahtjevu 12, naznačen time da R9 može opcionalno biti zamijenjen s 1 do 3 supstituenta, odabrana od halogena, C1-C6 haloalkil, C1-C6 alkoksi, C1-C6 haloalkoksi, C1-C6 alkil, C2-C6 alkinil, okso, cijano, cikloalkil, heteroaril, NR13R14, NR13COR14, CH2NR13COR14, COR13, CONR13R14, SO2NR13R14, i NR13SO2R14;
ili R9 može biti zamijenjen s 3 do 10-dijelnim heterociklil, heteroaril, aril ili cikloalkil prstenom, ili izravno pričvršćenim ili putem povezujuće skupine odabrane od kisika, karbonila, opcionalno zamijenjenog C1-C6 alkilena ili opcionalno zamijenjenog C1-C6 alkilenoksi lanca; i
R13, R14 i R15 svaki zasebno predstavljaju vodik, C1-C6 alkil, ili fenil.
14. Spoj prema bilo kojem od zahtjeva 1 do 13, imajući formulu (IV),
[image]
tautomer istog, ili farmaceutski prihvatljiva sol navedenog spoja ili tautomera; naznačen time da Y predstavlja preostale atome 5 ili 6-dijelnog heteroaril prstena koji može opcionalno biti zamijenjen ili spojen s daljnjim prstenom, koji može dalje opcionalno biti zamijenjen, naznačen time da su navedeni opcionalni supstituenti kao što je određeno u bilo kojem od zahtjeva 1 do 13.
15. Spoj prema zahtjevu 1, koji je odabran od skupine koja se sastoji od:
(S)-1-cijano-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(3-fluorofenil)tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(2-fluorofenil)tiazol-2-il)pirolidin-3-karboksamid;
N-(5-(4-klorofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
N-(5-(3-klorofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
N-(5-(2-klorofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(5-metiltiazol-2-il)pirolidin-3-karboksamid;
N-(5-(tert-butil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(4-feniltiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(2-feniltiazol-5-il)pirolidin-3-karboksamid;
1-cijano-N-(5-fenil-1,3,4-tiadiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-etil-1,3,4-tiadiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(3-fenilizoksazol-5-il)pirolidin-3-karboksamid;
1-cijano-N-(3-(4-metoksifenil)izoksazol-5-il)pirolidin-3-karboksamid;
1-cijano-N-(5-fenilizoksazol-3-il)pirolidin-3-karboksamid;
N-(5-(tert-butil)izoksazol-3-il)-1-cijanopirolidin-3-karboksamid;
N-(3-(tert-butil)-1H-pirazol-5-il)-1-cijanopirolidin-3-karboksamid;
N-(benzo[d]tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(6-metilbenzo[d]tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(6-(trifluorometil)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(6-metoksibenzo[d]tiazol-2-il)pirolidin-3-karboksamid;
N-(6-bromobenzo[d]tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
N-(1H-benzo[d]imidazol-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(piridin-2-il)pirolidin-3-karboksamid;
N-(5-kloropiridin-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(5-metilpiridin-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-metoksipiridin-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-morfolinopiridin-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(piperidin-1-il)piridin-2-il)pirolidin-3-karboksamid;
N-(5-(1H-imidazol-1-il)piridin-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(4-fenilpiridin-2-il)pirolidin-3-karboksamid;
N-([2,3’-bipiridin]-6’-il)-1-cijanopirolidin-3-karboksamid;
N-([3,3’-bipiridin]-6-il)-1-cijanopirolidin-3-karboksamid;
N-([3,4’-bipiridin]-6-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(6-fenilpiridin-3-il)pirolidin-3-karboksamid;
1-cijano-N-(6-fenilpiridazin-3-il)pirolidin-3-karboksamid;
1-cijano-N-(2-fenilpirimidin-5-il)pirolidin-3-karboksamid;
1-cijano-N-(5-cikloheksilpiridin-2-il)pirolidin-3-karboksamid;
N-(1-benzil-1H-indazol-5-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(1-propil-1H-benzo[d]imidazol-5-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-fenil-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-fenil-1H-pirazol-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(tetrahidro-2H-piran-4-il)-1H-pirazol-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-fenil-1H-1,2,3-triazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-fenil-1H-pirazol-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-metilbenzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(7-metilbenzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-N-(4-bromobenzo[d]tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(imidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-N-(7-bromoimidazo[1,2-a]piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(6-bromoimidazo[1,2-a]piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(pirazolo[1,5-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-metoksipiridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-fenilpiridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-fenilpiridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1,8-naftiridin-2-il)pirolidin-3-karboksamid;
(S)-N-(5-benziltiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(izokvinolin-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(tetrahidro-2H-piran-4-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-metil-5-fenil-1H-pirazol-3-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(4-metoksipiperidin-1-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-N-(6-(1H-1,2,3-triazol-1-il)benzo[d]tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(6-(2H-1,2,3-triazol-2-il)benzo[d]tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-(metilkarbamoil)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-metil-5-(morfolinometil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-fluorofenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3,4-difluorofenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-(trifluorometil)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(piridin-4-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(piridin-2-il)tiazol-2-il)pirolidin-3-karboksamid;
(R)-1-cijano-N-(5-fenilpiridin-2-il)pirolidin-3-karboksamid;
(2S,3S)-1-cijano-2-metil-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
(2S,3S)-1-cijano-N-(5-(4-fluorofenil)tiazol-2-il)-2-metilpirolidin-3-karboksamid;
(2S,3S)-1-cijano-2-metil-N-(1-fenil-1H-imidazol-4-il)pirolidin-3-karboksamid;
(2S,3S)-1-cijano-2-metil-N-(5-fenil-1H-pirazol-3-il)pirolidin-3-karboksamid;
(2S,3S)-1-cijano-2-metil-N-(5-(tetrahidro-2H-piran-4-il)tiazol-2-il)pirolidin-3-karboksamid;
(2S,3S)-N-(5-(2-klorofenil)tiazol-2-il)-1-cijano-2-metilpirolidin-3-karboksamid;
1-cijano-3-metil-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
1-cijano-3-metil-N-(1-fenil-1H-imidazol-4-il)pirolidin-3-karboksamid;
1-cijano-3-(metoksimetil)-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
1,3-dicijano-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
(3S,4S)-1-cijano-4-metil-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
(3 S,4S)-1-cijano-4-metil-N-(5-metiltiazol-2-il)pirolidin-3-karboksamid;
(3S,4S)-N-(5-(2-klorofenil)tiazol-2-il)-1-cijano-4-metilpirolidin-3-karboksamid;
(3S,4S)-1-cijano-4-metil-N-(1-fenil-1H-imidazol-4-il)pirolidin-3-karboksamid;
(3S,4S)-1-cijano-4-etil-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
(3S,4S)-1-cijano-4-etil-N-(1-fenil-1H-imidazol-4-il)pirolidin-3-karboksamid;
1-cijano-5-metil-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
1-cijano-5-metil-N-(1-fenil-1H-imidazol-4-il)pirolidin-3-karboksamid;
1-cijano-5-metil-N-(5-fenil-1H-pirazol-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-morfolinotiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(4-metilpiperazin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
N-(5-(2-(acetamidometil)piperidin-1-il)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(5-(metil(fenil)amino)tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(indolin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(piperidin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(izoindolin-2-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3,4-dihidroizokvinolin-2(1H)-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-((R)-2-(metoksimetil)pirolidin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-((S)-2-(metoksimetil)pirolidin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(5-okso-1,4-diazepan-1-il)tiazol-2-il)pirolidin-3-karboksamid;
(R)-1-cijano-N-(5-morfolinotiazol-2-il)pirolidin-3-karboksamid;
(R)-1-cijano-N-(5-(piperidin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
(3S,4S)-1-cijano-4-metil-N-(5-(piperidin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-5-metil-N-(5-(piperidin-1-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(pirolidin-1-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(pirolidin-1-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(pirolidin-1-il)pirazin-2-il)pirolidin-3-karboksamid;
N-(5-(2-aminofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
N-(5-(3-aminofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
N-(5-(4-aminofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(5-(piridin-3-il)tiazol-2-il)pirolidin-3-karboksamid;
(E)-1-cijano-N-(5-(2-ciklopropilvinil)tiazol-2-il)pirolidin-3-karboksamid;
N-(5-(4-acetamidofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
N-(5-(2-acetamidofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
1-cijano-N-(5-(3-(metilsulfonamido)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3-cijanofenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-cijanofenil)tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(3,5-dimetilizoksazol-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(4-metoksifenil)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-fenilbenzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(1-metil-1H-pirazol-5-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(1-metil-1H-pirazol-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetil-1H-pirazol-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(5-metilizoksazol-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(7-(3,5-dimetilizoksazol-4-il)imidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)imidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-ciklopropilimidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid 1-cijano-N-(6-ciklopropilbenzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,6-dimetoksipiridazin-4-il)imidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,6-dimetoksipiridazin-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(2S,3S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)benzo[d]tiazol-2-il)-2-metilpirolidin-3-karboksamid;
1-cijano-N-(5-(p-tolil)piridin-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(m-tolil)piridin-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(o-tolil)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)-5-metilimidazo[1,2-a]piridin-2-il)pirolidin-3 -karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)-7-metilbenzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(7-metil-6-(1-metil-1H-pirazol-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(morfolinometil)tiazol-2-il)pirolidin-3-karboksamid;
1-cijano-N-(5-(pirolidin-1-ilmetil)tiazol-2-il)pirolidin-3-karboksamid;
(3S)-1-cijano-N-(5-((2,6-dimetilmorfolino)metil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(((R)-2-(metoksimetil)pirolidin-1-il)metil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(((S)-2-(metoksimetil)pirolidin-1-il)metil)tiazol-2-il)pirolidin-3-karboksamid;
(2S,3S)-1-cijano-N-(5-(((R)-2-(metoksimetil)pirolidin-1-il)metil)tiazol-2-il)-2-metilpirolidin-3-karboksamid;
(S)-N-(1-benzil-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(1-fenetil-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-izobutil-1H-imidazol-4-il)pirolidin-3-karboksamid;
(2S,3S)-N-(1-benzil-1H-imidazol-4-il)-1-cijano-2-metilpirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-fluorofenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(3-fluorofenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-fluorofenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-(trifluorometil)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(3-(trifluorometil)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-(metilkarbamoil)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(3-(metilkarbamoil)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-(metilkarbamoil)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-((2-metoksietil)karbamoil)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-metoksifenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-metoksifenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(tetrahidro-2H-piran-4-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-cikloheksil-1H-imidazol-4-il)pirolidin-3-karboksamid;
(3S)-1-cijano-N-(1-(2,3-dihidro-1H-inden-1-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2,3-dihidro-1H-inden-2-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-((tetrahidro-2H-piran-4-il)metil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-((S)-1-feniletil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-((R)-1-feniletil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(piridin-2-ilmetil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(piridin-3-ilmetil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(piridin-4-ilmetil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-((3,5-dimetilizoksazol-4-il)metil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(2S,3S)-1-cijano-2-metil-N-(1-((S)-1-feniletil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(3S,4S)-1-cijano-4-metil-N-(1-((S)-1-feniletil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-metilpiridin-2-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(6-metilpiridin-2-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(R)-1-cijano-N-(1-(2-metilpirimidin-4-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijanofenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-N-(1-benzil-2-metil-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-(3,5-dimetilizoksazol-4-il)etil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(3-cijanofenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(piridin-3-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(piridin-4-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(3-metoksifenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(3S)-N-(1-(1-benzoilpiperidin-3-il)-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(3S)-N-(1-(1-benzoilpirolidin-3-il)-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(3S)-N-(1-(1-benzilpiperidin-3-il)-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(3S)-1-cijano-N-(1-(1-metilpiperidin-3-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(3S)-1-cijano-N-(1-(1-metilpirolidin-3-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-N-(5-acetil-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-izobutiril-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-N-(5-benzoil-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(2-metoksibenzoil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-picolinoil-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(1-metil-1H-pirazol-3-karbonil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(1-metil-2-okso-1,2-dihidropiridin-3-karbonil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-nikotinoil-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(dimetilglicil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
metil(S)-2-(1-cijanopirolidin-3-karboksamido)-6,7-dihidrotiazolo[5,4-c]piridin-5(4H)-karboksilat;
2-metoksietil(S)-2-(1-cijanopirolidin-3-karboksamido)-6,7-dihidrotiazolo[5,4-c]piridin-5(4H)-karboksilat;
(S)-1-cijano-N-(5-metil-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-N-(5-benzil-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(metilsulfonil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(izopropilsulfonil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(fenilsulfonil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-etinilfenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3-etinilfenil)tiazol-2-il)pirolidin-3-karboksamid;
(3S)-1-cijano-N-(5-(N-(1-feniletil)sulfamoil)piridin-2-il)pirolidin-3-karboksamid;
(3S)-1-cijano-N-(5-(N-metil-N-(1-feniletil)sulfamoil)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(5-metil-1,2,4-oksadiazol-3-il)imidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid;
(3S,4S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)imidazo[1,2-a]piridin-2-il)-4-(trifluorometil)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(1-metil-1H-pirazol-4-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(N,N-dimetilsulfamoil)-4,5,6,7-tetrahidrotiazolo[5,4-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(piridazin-4-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-cijano-3-fluorofenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-N-(5-(1H-indazol-7-il)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(5-(3-(1H-imidazol-1-il)fenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-(metilsulfonamido)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-N-(5-(3-(1H-pirazol-1-il)fenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-cijano-3-(trifluorometoksi)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-cijano-3-metoksifenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-sulfamoilfenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-N-(5-(1H-indazol-6-il)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(5-(1H-indazol-5-il)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-6-(2-(1-cijanopirolidin-3-karboksamido)tiazol-5-il)-N-metilpicolinamid;
(S)-6-(2-(1-cijanopirolidin-3-karboksamido)tiazol-5-il)-N-etilpicolinamid;
(S)-1-cijano-N-(5-(1-metil-1H-indazol-5-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(1-(2-metoksietil)-1H-indazol-5-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(2-oksoindolin-7-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3-metil-1H-indazol-5-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-N-(5-(1H-indazol-4-il)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(4-fluoro-3-(metilkarbamoil)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-N-(5-(3-karbamoilfenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3-(metilkarbamoil)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3-(etilkarbamoil)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3-(dimetilkarbamoil)fenil)tiazol-2-il)pirolidin-3-karboksamid;
(S)-N-(5-(3-karbamoil-4-fluorofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(5-(3-karbamoil-4-klorofenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(5-(4-kloro-3-(metilkarbamoil)fenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(5-(4-kloro-3-(prop-2-in-1-ilkarbamoil)fenil)tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(izopropilsulfonil)-4,5,6,7-tetrahidropirazolo[1,5-a]pirazin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-fenil-4,5,6,7-tetrahidropirazolo[1,5-a]pirazin-2-il)pirolidin-3-karboksamid;
(S)-N-(5-benzil-4,5,6,7-tetrahidropirazolo[1,5-a]pirazin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-(2-metoksietoksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-cijano-5-(2-metoksietoksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-(3-morfolinopropoksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-cijano-5-(3-morfolinopropoksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-(((S)-tetrahidrofuran-3-il)oksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-cijano-5-(((S)-tetrahidrofuran-3-il)oksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-(oksetan-3-iloksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(2-cijano-5-(oksetan-3-iloksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(pirazolo[1,5-a]pirimidin-7-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(imidazo[1,2-a]pirimidin-5-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(imidazo[1,2-a]piridin-5-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(imidazo[1,2-a]pirazin-6-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(imidazo[1,2-a]pirimidin-6-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1,7-naftiridin-6-il)pirolidin-3-karboksamid;
(S)-N-(6-(3-klorofenil)pirimidin-4-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(2’-amino-[4,4’-bipiridin]-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(2’-(metilamino)-[4,4’-bipiridin]-2-il)pirolidin-3-karboksamid;
(S)-3-(1-cijanopirolidin-3-karboksamido)-N-metilizokvinolin-6-karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)izokvinolin-3-il)pirolidin-3-karboksamid;
(S)-N-(4-(1H-indazol-4-il)piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(6-etinilizokvinolin-3-il)pirolidin-3-karboksamid ;
(2S,3S)-1-cijano-N-(6- etinilizokvinolin-3-il)-2-metilpirolidin-3-karboksamid;
(S)-3-(1-cijanopirolidin-3-karboksamido) izokvinolin-6-karboksamid;
(2S,3S)-N-(6-(1H-pirazol-4-il)izokvinolin-3-il)-1-cijano-2-metilpirolidin-3-karboksamid;
(S)-1-cijano-N-(pirazolo[1,5-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-fenilpiridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(piridin-3-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(piridin-3-il)tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(trifluorometil)imidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-metil-5-(m-tolil)-1H-pirazol-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(kvinolin-3-il)pirolidin-3-karboksamid;
(S)-N-(4-(tert-butil)piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(piridin-4-il)pirimidin-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-fenilpiridazin-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(oksazol-5-il)imidazo[1,2-a]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(izopropilsulfonil)-5,6,7,8-tetrahidro-4H-tiazolo[4,5-d]azepin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-(1-(2-metoksietil)-1H-pirazol-4-il)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
3-cijano-N-(5-feniltiazol-2-il)-3-azabiciklo[3.1.0]heksan-1-karboksamid;
2-cijano-N-(5-feniltiazol-2-il)-2-azabiciklo[3.1.0]heksan-4-karboksamid;
(3S,4S)-1-cijano-N-(5-feniltiazol-2-il)-4-(trifluorometil)pirolidin-3-karboksamid;
(3S,4R)-1-cijano-N-(5-feniltiazol-2-il)-4-(piridin-3-il)pirolidin-3-karboksamid;
(3S,4R)-1-cijano-N-(5-feniltiazol-2-il)-4-(pirimidin-5-il)pirolidin-3-karboksamid;
1-cijano-3-metoksi-N-(5-feniltiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)tiazolo[4,5-b]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(5-(3,5-dimetilizoksazol-4-il)tiazolo[5,4-b]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(2,6-dimetilfenil)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(1,3-dimetil-1H-pirazol-4-il)benzo[d]tiazol-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(5-(trifluorometil)-1H-pirazol-4-il)izokvinolin-3-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(3-(5-metilizoksazol-4-il)fenil)piridin-2-il)pirolidin-3-karboksamid;
(S)-N-(4-(1H-pirazol-4-il)piridin-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(6-(1H-pirazol-4-il)benzo[d]tiazol-2-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(1-(4-(1H-pirazol-4-il)fenil)-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(4-(5-metil-1H-pirazol-4-il)piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(6-(3,5-dimetilizoksazol-4-il)tiazolo[4,5-c]piridin-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(2’-(5-metilizoksazol-4-il)-[4,4’-bipiridin]-2-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(1,3-dimetil-1H-indazol-5-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(3-metil-1H-indazol-6-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-5-il)-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(S)-N-(1-(1H-indazol-6-il)-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-fluoro-3-metoksifenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-N-(1-(1H-indazol-4-il)-1H-imidazol-4-il)-1-cijanopirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-ciklopropilfenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(kvinolin-4-il)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-metil-N-(4-(4-(metilkarbamoil)fenil)tiazol-2-il)pirolidin-2-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-metoksifenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-metilfenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
(S)-1-cijano-N-(1-(4-cijano-3-(trifluorometil)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid; i
(S)-1-cijano-N-(1-(4-cijano-3-(trifluorometoksi)fenil)-1H-imidazol-4-il)pirolidin-3-karboksamid;
tautomer istog, ili farmaceutski prihvatljiva sol navedenog spoja ili tautomera.
16. Spoj prema bilo kojem od zahtjeva 1 do 15, tautomer istog, ili farmaceutski prihvatljiva sol navedenog spoja ili tautomera, za korištenje kao lijek.
17. Spoj prema bilo kojem od zahtjeva 1 do 15, tautomer istog, ili farmaceutski prihvatljiva sol navedenog spoja ili tautomera, za korištenje u liječenju raka, neurodegenerativnih poremećaja, COPD, upala, virusnih ili bakterijskih infekcija ili poremećaja metabolizma.
18. Farmaceutski sastav koji sadrži spoj formule (I) kao što je određen u bilo kojem od zahtjeva 1 do 15, tautomer istog, ili farmaceutski prihvatljiva sol navedenog spoja ili tautomera, zajedno s jednom ili više farmaceutski prihvatljivih pomoćnih tvari.
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GBGB1416754.8A GB201416754D0 (en) | 2014-09-23 | 2014-09-23 | Novel compounds |
EP15774652.0A EP3197883B1 (en) | 2014-09-23 | 2015-09-22 | Novel compounds |
PCT/GB2015/052729 WO2016046530A1 (en) | 2014-09-23 | 2015-09-22 | Novel compounds |
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HRP20200962T1 true HRP20200962T1 (hr) | 2020-10-02 |
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HRP20200962TT HRP20200962T1 (hr) | 2014-09-23 | 2020-06-17 | Novi spojevi |
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EP (2) | EP3828179A1 (hr) |
JP (3) | JP6549703B2 (hr) |
KR (1) | KR102493967B1 (hr) |
CN (2) | CN111592534B (hr) |
AU (1) | AU2015323572B2 (hr) |
CA (1) | CA2958262C (hr) |
CY (1) | CY1122983T1 (hr) |
DK (1) | DK3197883T3 (hr) |
ES (1) | ES2798473T3 (hr) |
GB (1) | GB201416754D0 (hr) |
HR (1) | HRP20200962T1 (hr) |
HU (1) | HUE050732T2 (hr) |
IL (1) | IL250345B (hr) |
LT (1) | LT3197883T (hr) |
MX (1) | MX2017003358A (hr) |
PL (1) | PL3197883T3 (hr) |
PT (1) | PT3197883T (hr) |
RS (1) | RS60468B1 (hr) |
RU (1) | RU2691389C2 (hr) |
SG (1) | SG11201700847YA (hr) |
SI (1) | SI3197883T1 (hr) |
WO (1) | WO2016046530A1 (hr) |
Families Citing this family (55)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112016029662B1 (pt) | 2014-06-19 | 2023-10-24 | Takeda Pharmaceutical Company Limited | COMPOSTO DE FÓRMULA Bf OU UMA FORMA FARMACEUTICAMENTE ACEITÁVEL DO MESMO, COMPOSIÇÃO FARMACÊUTICA COMPREENDENDO O MESMO E SEU USO |
GB201416754D0 (en) * | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
WO2016156816A1 (en) * | 2015-03-30 | 2016-10-06 | Mission Therapeutics Limited | 1-cyano-pyrrolidine compounds as usp30 inhibitors |
US10807945B2 (en) * | 2015-06-22 | 2020-10-20 | Sumitomo Dainippon Pharma Co., Ltd. | 1,4-disubstituted imidazole derivative |
EP3800186A1 (en) * | 2015-07-14 | 2021-04-07 | 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 |
EP3433246B1 (en) | 2016-03-24 | 2022-05-04 | Mission Therapeutics Limited | 1-cyano-pyrrolidine derivatives as dbu inhibitors |
WO2017184751A1 (en) * | 2016-04-20 | 2017-10-26 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Compositions and methods for treating and preventing hypertension |
AR108325A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
AR108326A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
WO2018060689A1 (en) * | 2016-09-27 | 2018-04-05 | Mission Therapeutics Limited | Cyanopyrrolidine derivatives with activity as inhibitors of 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 |
CN110198937A (zh) * | 2017-02-14 | 2019-09-03 | 华东理工大学 | N-(5-吗啉代噻唑-2-基)甲酰胺类化合物及其制备方法和用途 |
WO2018209132A1 (en) | 2017-05-10 | 2018-11-15 | Cortexyme, Inc. | Aminopyridine compounds and methods for the preparation and use thereof |
GB201708652D0 (en) * | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
AR112027A1 (es) | 2017-06-15 | 2019-09-11 | Biocryst Pharm Inc | Inhibidores de alk 2 quinasa que contienen imidazol |
US11059809B2 (en) | 2017-06-20 | 2021-07-13 | Mission Therapeutics Limited | Substituted cyanopyrrolidines with activity as DUB inhibitors |
HRP20230251T1 (hr) * | 2017-08-01 | 2023-04-14 | Merck Patent Gmbh | Derivati tiazolopridina kao antagonisti adenozinskih receptora |
CN107445981B (zh) * | 2017-08-25 | 2018-06-22 | 牡丹江医学院 | 一种用于防治***的活性化合物 |
CN111148743B (zh) | 2017-10-06 | 2023-12-15 | 福马治疗有限公司 | 抑制泛素特异性肽酶30 |
WO2019079626A1 (en) * | 2017-10-19 | 2019-04-25 | Samumed, Llc | 6- (HETEROARYL 5-CHAIN) ISOQUINOLIN-3-YL CARBOXAMIDES, THEIR PREPARATION AND THEIR USE |
US10413537B2 (en) | 2017-10-27 | 2019-09-17 | Samumed, Llc | 6-(5-membered heteroaryl)isoquinolin-3-yl-(5-membered heteroaryl) carboxamides and preparation and use thereof |
WO2019084497A1 (en) * | 2017-10-27 | 2019-05-02 | Samumed, Llc | 6- (HETEROARYL AND ARYL WITH 6 CHAINS) ISOQUINOLIN-3-YL CARBOXAMIDES, THEIR PREPARATION AND THEIR USE |
US10703748B2 (en) | 2017-10-31 | 2020-07-07 | Samumed, Llc | Diazanaphthalen-3-yl carboxamides and preparation and use thereof |
AR114422A1 (es) | 2018-03-30 | 2020-09-02 | Syngenta Participations Ag | Compuestos herbicidas |
JP7449242B2 (ja) * | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス,インコーポレイテッド | ユビキチン特異的ペプチダーゼ30(usp30)阻害剤として有用な縮合二環化合物 |
JP2021534122A (ja) * | 2018-08-09 | 2021-12-09 | ヴァロ アーリー ディスカバリー, インコーポレイテッド | 脱ユビキチン化酵素usp25及びusp28の阻害 |
EP3837262A1 (en) | 2018-08-14 | 2021-06-23 | Amgen Inc. | N-cyano-7-azanorbornane derivatives and uses thereof |
US11612606B2 (en) | 2018-10-03 | 2023-03-28 | Genentech, Inc. | 8-aminoisoquinoline compounds and uses thereof |
CA3110113A1 (en) | 2018-10-05 | 2020-04-09 | Forma Therapeutics, Inc. | Fused pyrrolines which act as ubiquitin-specific protease 30 (usp30) inhibitors |
UY38435A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas urea 6,7-dihidro-4h-pirazol[1,5-a] pirazinas activas contra el virus de la hepatitis b (vhb) |
UY38434A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas 6,7-dihidro-4h-pirazolo[1,5-a]pirazin indol-2-carboxamidas activas contra el virus de la hepatitis b (hbv) |
CN113453679A (zh) | 2018-12-20 | 2021-09-28 | C4医药公司 | 靶向蛋白降解 |
GB201905375D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
GB201905371D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
KR102397752B1 (ko) * | 2019-06-19 | 2022-05-16 | 주식회사 엘지화학 | 인돌 또는 인다졸 화합물의 제조방법 |
GB201912674D0 (en) | 2019-09-04 | 2019-10-16 | Mission Therapeutics Ltd | Novel compounds |
AU2021253617A1 (en) | 2020-04-08 | 2022-12-01 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as USP30 inhibitors |
BR112022020644A2 (pt) | 2020-05-28 | 2022-12-06 | Mission Therapeutics Ltd | Derivados de n-(1-ciano-pirrolidin-3-il)-5-(3-(trifluorometil)fenil) oxazol-2-carboxamida e os correspondentes derivados de oxadiazol como inibidores de usp30 para o tratamento de disfunção mitocondrial |
US20230234967A1 (en) * | 2020-05-28 | 2023-07-27 | Senda Biosciences, Inc. | Fused Azole Heterocycles as AHR Antagonists |
EP4161920A1 (en) | 2020-06-04 | 2023-04-12 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
CA3186148A1 (en) | 2020-06-08 | 2021-12-16 | Mission Therapeutics Limited | 1-(5-(2-cyanopyridin-4-yl)oxazole-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyr role-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 |
TW202402754A (zh) * | 2021-03-04 | 2024-01-16 | 美商美國禮來大藥廠 | Fgfr3抑制劑化合物 |
CA3224123A1 (en) * | 2021-07-26 | 2023-02-02 | James Griffin | Small molecule inhibition of deubiquitinating enzyme josephin domain containing 1 (josd1) as a targeted therapy for leukemias with mutant janus kinase 2 (jak2) |
WO2023099561A1 (en) | 2021-12-01 | 2023-06-08 | Mission Therapeutics Limited | Substituted n-cyanopyrrolidines with activity as usp30 inhibitors |
WO2023107714A2 (en) * | 2021-12-10 | 2023-06-15 | Prothena Biosciences Limited | Methods for treating neurological disorders |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
US6410561B1 (en) | 1998-03-26 | 2002-06-25 | Japan Tobacco Inc. | Amide derivatives and nociceptin antagonists |
WO2001077073A1 (en) * | 2000-04-06 | 2001-10-18 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
JP2007529496A (ja) | 2004-03-19 | 2007-10-25 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 抗菌剤としてのイミダゾピリジン及びイミダゾピリミジン誘導体 |
US20090182140A1 (en) | 2005-12-02 | 2009-07-16 | Mitsubishi Tanabe Pharma Corporation | Alicyclic Heterocyclic Compound |
TWI332501B (en) * | 2006-07-14 | 2010-11-01 | Lg Life Sciences Ltd | Melanocortin receptor agonists |
WO2010052222A1 (en) | 2008-11-07 | 2010-05-14 | Evotec Neurosciences Gmbh | (dihydro)naphthyridinone derivatives as histamine h3 receptor antagonists |
JP5743897B2 (ja) | 2008-11-20 | 2015-07-01 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーGlaxoSmithKline LLC | 化合物 |
WO2012040527A2 (en) * | 2010-09-24 | 2012-03-29 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
WO2012174312A2 (en) | 2011-06-15 | 2012-12-20 | Glaxosmithkline Llc | Benzimidazole derivatives as antiviral agents |
SG11201401608PA (en) * | 2011-10-19 | 2014-07-30 | Vivolux Ab | Method for inhibition of deubiquitinating activity |
JP6397407B2 (ja) | 2012-07-19 | 2018-09-26 | ドレクセル ユニバーシティ | 細胞タンパク質ホメオスタシスを調節するためのシグマ受容体リガンド |
JP2016523517A (ja) | 2013-05-02 | 2016-08-12 | イー3エックス バイオ インコーポレイテッド | ユビキチンリガーゼのモジュレーターを同定するための方法 |
GB201416754D0 (en) * | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
WO2016156816A1 (en) | 2015-03-30 | 2016-10-06 | Mission Therapeutics Limited | 1-cyano-pyrrolidine compounds as usp30 inhibitors |
EP3800186A1 (en) | 2015-07-14 | 2021-04-07 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
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