JP2019504009A5 - - Google Patents
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- JP2019504009A5 JP2019504009A5 JP2018531219A JP2018531219A JP2019504009A5 JP 2019504009 A5 JP2019504009 A5 JP 2019504009A5 JP 2018531219 A JP2018531219 A JP 2018531219A JP 2018531219 A JP2018531219 A JP 2018531219A JP 2019504009 A5 JP2019504009 A5 JP 2019504009A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- cyanopyrrolidin
- carboxamide
- compound
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 230000007812 deficiency Effects 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 7
- -1 cyano, hydroxyl Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 208000011580 syndromic disease Diseases 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 208000008955 Mucolipidoses Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 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
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 2
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 claims 2
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 2
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000035772 mutation Effects 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 102000045222 parkin Human genes 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 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
- 125000006714 (C3-C10) heterocyclyl group Chemical group 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
- 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
- ZFIDAESINVCFIU-LLVKDONJSA-N 3-(3-chlorophenyl)-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1,2-oxazole-5-carboxamide Chemical compound ClC=1C=C(C=CC=1)C1=NOC(=C1)C(=O)NC[C@@H]1CN(CC1)C#N ZFIDAESINVCFIU-LLVKDONJSA-N 0.000 claims 1
- JHHBWYNMUIATMU-LLVKDONJSA-N 3-(4-chlorophenyl)-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]-1,2-oxazole-5-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=NOC(=C1)C(=O)NC[C@@H]1CN(CC1)C#N JHHBWYNMUIATMU-LLVKDONJSA-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
- 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
- MJYAYUHQVOKQOU-UHFFFAOYSA-N 3-[[(5-phenylpyridin-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C=CC(=NC=1)NCC1CN(CC1)C#N MJYAYUHQVOKQOU-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
- OKPFVCAOSFLUBO-UHFFFAOYSA-N 3-[[(6-phenylpyridin-2-yl)amino]methyl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=CC(=N1)NCC1CN(CC1)C#N OKPFVCAOSFLUBO-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
- 208000009270 3-hydroxyacyl-CoA dehydrogenase deficiency Diseases 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
- DBDLNSFTJIEYFE-SNVBAGLBSA-N 6-chloro-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound ClC1=CN2C=C(N=C2C=C1)C(=O)NC[C@H]1CCN(C1)C#N DBDLNSFTJIEYFE-SNVBAGLBSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- GXBHHKRJFXMETN-SNVBAGLBSA-N 7-chloro-N-[[(3R)-1-cyanopyrrolidin-3-yl]methyl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound ClC1=CC2=NC(=CN2C=C1)C(=O)NC[C@H]1CCN(C1)C#N GXBHHKRJFXMETN-SNVBAGLBSA-N 0.000 claims 1
- 102100026882 Alpha-synuclein Human genes 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 201000005943 Barth syndrome Diseases 0.000 claims 1
- 102000051485 Bcl-2 family Human genes 0.000 claims 1
- 108700038897 Bcl-2 family Proteins 0.000 claims 1
- 208000014644 Brain disease Diseases 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
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 201000000915 Chronic Progressive External Ophthalmoplegia Diseases 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims 1
- 102000015782 Electron Transport Complex III Human genes 0.000 claims 1
- 108010024882 Electron Transport Complex III Proteins 0.000 claims 1
- 208000032274 Encephalopathy Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101000804964 Homo sapiens DNA polymerase subunit gamma-1 Proteins 0.000 claims 1
- 101000595929 Homo sapiens POLG alternative reading frame Proteins 0.000 claims 1
- 101000605835 Homo sapiens Serine/threonine-protein kinase PINK1, mitochondrial Proteins 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 102100030358 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Human genes 0.000 claims 1
- 101710150008 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Proteins 0.000 claims 1
- 208000006136 Leigh Disease Diseases 0.000 claims 1
- 208000017507 Leigh syndrome Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims 1
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims 1
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000010428 Muscle Weakness Diseases 0.000 claims 1
- 206010028372 Muscular weakness Diseases 0.000 claims 1
- 208000036572 Myoclonic epilepsy Diseases 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
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| 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 |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| JP6959252B2 (ja) | 2016-03-24 | 2021-11-02 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
| 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 |
| JP7208931B2 (ja) * | 2017-06-20 | 2023-01-19 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての活性をもつ置換シアノピロリジン類 |
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2015
- 2015-12-17 GB GBGB1522267.2A patent/GB201522267D0/en not_active Ceased
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2016
- 2016-12-16 SG SG11201804934PA patent/SG11201804934PA/en unknown
- 2016-12-16 JP JP2018531219A patent/JP6898327B2/ja active Active
- 2016-12-16 RU RU2018123779A patent/RU2734256C2/ru active
- 2016-12-16 US US15/781,615 patent/US11130748B2/en active Active
- 2016-12-16 ES ES16816365T patent/ES2929376T3/es active Active
- 2016-12-16 EP EP22195076.9A patent/EP4122929A1/en not_active Withdrawn
- 2016-12-16 WO PCT/GB2016/053971 patent/WO2017103614A1/en not_active Ceased
- 2016-12-16 EP EP16816365.7A patent/EP3390391B1/en active Active
- 2016-12-16 BR BR112018007208-7A patent/BR112018007208B1/pt active IP Right Grant
- 2016-12-16 MX MX2018007449A patent/MX387482B/es unknown
- 2016-12-16 KR KR1020187020277A patent/KR102663994B1/ko active Active
- 2016-12-16 CN CN201680073270.2A patent/CN108368089B/zh active Active
- 2016-12-16 CA CA3008747A patent/CA3008747C/en active Active
- 2016-12-16 MY MYPI2018000546A patent/MY196729A/en unknown
- 2016-12-16 MA MA044050A patent/MA44050A/fr unknown
- 2016-12-16 AU AU2016373533A patent/AU2016373533B2/en active Active
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2018
- 2018-03-28 IL IL258444A patent/IL258444B/en active IP Right Grant
- 2018-06-18 CO CONC2018/0006299A patent/CO2018006299A2/es unknown
- 2018-07-16 ZA ZA2018/04739A patent/ZA201804739B/en unknown
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2021
- 2021-08-16 US US17/402,802 patent/US11958833B2/en active Active
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