JP2018510183A5 - - Google Patents
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- JP2018510183A5 JP2018510183A5 JP2017551189A JP2017551189A JP2018510183A5 JP 2018510183 A5 JP2018510183 A5 JP 2018510183A5 JP 2017551189 A JP2017551189 A JP 2017551189A JP 2017551189 A JP2017551189 A JP 2017551189A JP 2018510183 A5 JP2018510183 A5 JP 2018510183A5
- Authority
- JP
- Japan
- Prior art keywords
- cyanopyrrolidin
- carboxamide
- alkylene
- methyl
- pyrazol
- 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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- -1 cyano, hydroxyl Chemical group 0.000 claims 70
- 150000001875 compounds Chemical class 0.000 claims 51
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 37
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 17
- 229910052731 fluorine Inorganic materials 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 13
- 125000001153 fluoro group Chemical group F* 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 208000011580 syndromic disease Diseases 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 230000007812 deficiency Effects 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 8
- 125000004450 alkenylene group Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 208000008955 Mucolipidoses Diseases 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 4
- 208000014644 Brain disease Diseases 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 206010058892 Carnitine deficiency Diseases 0.000 claims 4
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 4
- 208000032274 Encephalopathy Diseases 0.000 claims 4
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 4
- 235000010290 biphenyl Nutrition 0.000 claims 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
- 208000006443 lactic acidosis Diseases 0.000 claims 4
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 4
- 230000002438 mitochondrial effect Effects 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 4
- 150000003573 thiols Chemical class 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- UCOHKZKRNWNULS-UHFFFAOYSA-N aminocyanamide Chemical compound NNC#N UCOHKZKRNWNULS-UHFFFAOYSA-N 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 210000003205 muscle Anatomy 0.000 claims 3
- 230000035772 mutation Effects 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 208000009270 3-hydroxyacyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 208000019932 Aciduria Diseases 0.000 claims 2
- 206010003591 Ataxia Diseases 0.000 claims 2
- 201000005943 Barth syndrome Diseases 0.000 claims 2
- 208000031229 Cardiomyopathies Diseases 0.000 claims 2
- 108700005857 Carnitine palmitoyl transferase 1A deficiency Proteins 0.000 claims 2
- 208000005359 Carnitine palmitoyl transferase 1A deficiency Diseases 0.000 claims 2
- 108700005858 Carnitine palmitoyl transferase 2 deficiency Proteins 0.000 claims 2
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 2
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims 2
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims 2
- 102000015782 Electron Transport Complex III Human genes 0.000 claims 2
- 108010024882 Electron Transport Complex III Proteins 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 201000008892 GM1 Gangliosidosis Diseases 0.000 claims 2
- 208000032087 Hereditary Leber Optic Atrophy Diseases 0.000 claims 2
- 101000804964 Homo sapiens DNA polymerase subunit gamma-1 Proteins 0.000 claims 2
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 claims 2
- 101000595929 Homo sapiens POLG alternative reading frame Proteins 0.000 claims 2
- 102100030358 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Human genes 0.000 claims 2
- 101710150008 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Proteins 0.000 claims 2
- 201000000639 Leber hereditary optic neuropathy Diseases 0.000 claims 2
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 2
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 2
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 2
- 208000035032 Multiple sulfatase deficiency Diseases 0.000 claims 2
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims 2
- 102100035196 POLG alternative reading frame Human genes 0.000 claims 2
- 206010033799 Paralysis Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000013234 Pearson syndrome Diseases 0.000 claims 2
- 208000002009 Pyruvate Dehydrogenase Complex Deficiency Disease Diseases 0.000 claims 2
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims 2
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 2
- 206010057644 Testis cancer Diseases 0.000 claims 2
- 201000004010 carnitine palmitoyltransferase I deficiency Diseases 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000007547 defect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 2
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims 2
- 208000020468 mucolipidosis III alpha/beta Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- 230000001537 neural effect Effects 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 102000045222 parkin Human genes 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 230000000750 progressive effect Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 201000006473 pyruvate decarboxylase deficiency Diseases 0.000 claims 2
- 208000015445 pyruvate dehydrogenase deficiency Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 201000003120 testicular cancer Diseases 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- NUXIWBUQKROULG-CJNGLKHVSA-N (3aR,6aR)-1-(1-phenylimidazole-4-carbonyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound C1(=CC=CC=C1)N1C=NC(=C1)C(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N NUXIWBUQKROULG-CJNGLKHVSA-N 0.000 claims 1
- DYMWDTUJPDRKIQ-HIFRSBDPSA-N (3aR,6aR)-1-(2,3-dihydroindole-1-carbonyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound N1(CCC2=CC=CC=C12)C(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N DYMWDTUJPDRKIQ-HIFRSBDPSA-N 0.000 claims 1
- CSQVJQNXYCHHTK-QQPKSGGNSA-N (3aR,6aR)-1-(3-phenoxyazetidine-1-carbonyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile N-(1-cyanopiperidin-3-yl)-3-phenylbenzamide Chemical compound O=C(NC1CCCN(C1)C#N)c1cccc(c1)-c1ccccc1.O=C(N1CC(C1)Oc1ccccc1)N1CC[C@@H]2CN(C[C@H]12)C#N CSQVJQNXYCHHTK-QQPKSGGNSA-N 0.000 claims 1
- CMMRNABFYAATQI-HIFRSBDPSA-N (3aR,6aR)-1-(3-phenyl-1,2-oxazole-5-carbonyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NOC(=C1)C(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N CMMRNABFYAATQI-HIFRSBDPSA-N 0.000 claims 1
- JHHSTONZRLHGMH-CJNGLKHVSA-N (3aR,6aR)-1-(3-phenyl-1H-pyrazole-5-carbonyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NNC(=C1)C(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N JHHSTONZRLHGMH-CJNGLKHVSA-N 0.000 claims 1
- OUGVBBDEQQIAEA-QAPCUYQASA-N (3aR,6aR)-1-(4-fluoro-3-pyridin-4-ylbenzoyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound FC1=C(C=C(C(=O)N2[C@@H]3[C@H](CC2)CN(C3)C#N)C=C1)C1=CC=NC=C1 OUGVBBDEQQIAEA-QAPCUYQASA-N 0.000 claims 1
- LVLDVEIEEYCFQX-CJNGLKHVSA-N (3aR,6aR)-1-[3-(4-methoxyphenyl)-1,2-oxazole-5-carbonyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound COC1=CC=C(C=C1)C1=NOC(=C1)C(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N LVLDVEIEEYCFQX-CJNGLKHVSA-N 0.000 claims 1
- IHVYISFJPUVGPN-DYVFJYSZSA-N (3aR,6aR)-1-[3-(4-methoxyphenyl)-1H-pyrazole-5-carbonyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound COC1=CC=C(C=C1)C1=NNC(=C1)C(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N IHVYISFJPUVGPN-DYVFJYSZSA-N 0.000 claims 1
- QKSAQXTVNSAFHP-PBHICJAKSA-N (3aR,6aR)-1-[3-methoxy-4-(1-methylpyrazol-4-yl)benzoyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound COC=1C=C(C(=O)N2[C@@H]3[C@H](CC2)CN(C3)C#N)C=CC=1C=1C=NN(C=1)C QKSAQXTVNSAFHP-PBHICJAKSA-N 0.000 claims 1
- XISMVCGRSIDEMH-KDOFPFPSSA-N (3aR,6aR)-1-[4-(3-chloropyridin-4-yl)-3-methoxybenzoyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound ClC=1C=NC=CC=1C1=C(C=C(C(=O)N2[C@@H]3[C@H](CC2)CN(C3)C#N)C=C1)OC XISMVCGRSIDEMH-KDOFPFPSSA-N 0.000 claims 1
- KWDLHMCDAUEXPE-DYVFJYSZSA-N (3aR,6aR)-1-[4-fluoro-3-(1-methylpyrazol-4-yl)benzoyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound FC1=C(C=C(C(=O)N2[C@@H]3[C@H](CC2)CN(C3)C#N)C=C1)C=1C=NN(C=1)C KWDLHMCDAUEXPE-DYVFJYSZSA-N 0.000 claims 1
- QLSFKZAGQZHUKY-RISCZKNCSA-N (3aR,6aR)-5-cyano-N-(4-cyano-2-fluorophenyl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound FC1=C(NC(=O)N2CC[C@@H]3CN(C[C@H]23)C#N)C=CC(=C1)C#N QLSFKZAGQZHUKY-RISCZKNCSA-N 0.000 claims 1
- YPTROWCJXWUAJD-NEPJUHHUSA-N (3aR,6aR)-5-cyano-N-(5-methylpyridin-2-yl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound CC1=CN=C(C=C1)NC(=O)N2CC[C@H]3[C@@H]2CN(C3)C#N YPTROWCJXWUAJD-NEPJUHHUSA-N 0.000 claims 1
- ORRROJOQVQBSPY-APWZRJJASA-N (3aR,6aR)-5-cyano-N-[2-fluoro-4-(2-methylpyridin-4-yl)phenyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound C(#N)N1C[C@@H]2N(CC[C@@H]2C1)C(=O)NC1=C(C=C(C=C1)C1=CC(=NC=C1)C)F ORRROJOQVQBSPY-APWZRJJASA-N 0.000 claims 1
- DDFGJQDAKCUHFI-RNCFNFMXSA-N (3aR,6aR)-5-cyano-N-[2-fluoro-4-(trifluoromethoxy)phenyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound FC1=C(NC(=O)N2CC[C@@H]3CN(C[C@H]23)C#N)C=CC(OC(F)(F)F)=C1 DDFGJQDAKCUHFI-RNCFNFMXSA-N 0.000 claims 1
- NKSQYNVJOYRSIC-RNCFNFMXSA-N (3aR,6aR)-5-cyano-N-[2-fluoro-4-(trifluoromethyl)phenyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound FC1=C(NC(=O)N2CC[C@@H]3CN(C[C@H]23)C#N)C=CC(=C1)C(F)(F)F NKSQYNVJOYRSIC-RNCFNFMXSA-N 0.000 claims 1
- RNGVIKCHXWALJA-RNCFNFMXSA-N (3aR,6aR)-5-cyano-N-[2-fluoro-5-(trifluoromethyl)phenyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound FC1=C(NC(=O)N2CC[C@@H]3CN(C[C@H]23)C#N)C=C(C=C1)C(F)(F)F RNGVIKCHXWALJA-RNCFNFMXSA-N 0.000 claims 1
- HYNKWSOOZFQERY-MJGOQNOKSA-N (3aR,6aR)-5-cyano-N-[3-(2-methylpyridin-4-yl)phenyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound CC1=NC=CC(=C1)C1=CC=CC(NC(=O)N2CC[C@@H]3CN(C[C@H]23)C#N)=C1 HYNKWSOOZFQERY-MJGOQNOKSA-N 0.000 claims 1
- SVUMILBXHLHUDA-MJGOQNOKSA-N (3aR,6aR)-5-cyano-N-[4-(2-methylpyridin-4-yl)phenyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-1-carboxamide Chemical compound CC1=NC=CC(=C1)C1=CC=C(NC(=O)N2CC[C@@H]3CN(C[C@H]23)C#N)C=C1 SVUMILBXHLHUDA-MJGOQNOKSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- IEVPIDPBYIXIQS-UHFFFAOYSA-N 1-(1-cyanopyrrolidin-3-yl)-1-(2-methoxyethyl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C(#N)N1CC(CC1)N(C(=O)NC1=CC=C(C=C1)C(F)(F)F)CCOC IEVPIDPBYIXIQS-UHFFFAOYSA-N 0.000 claims 1
- IKBBDBCYLOYWSA-UHFFFAOYSA-N 1-(1-cyanopyrrolidin-3-yl)-1-methyl-3-(3-phenoxyphenyl)urea 1-(1-cyanopyrrolidin-3-yl)-1-methyl-3-(4-phenylphenyl)urea Chemical compound CN(C1CCN(C1)C#N)C(=O)Nc1ccc(cc1)-c1ccccc1.CN(C1CCN(C1)C#N)C(=O)Nc1cccc(Oc2ccccc2)c1 IKBBDBCYLOYWSA-UHFFFAOYSA-N 0.000 claims 1
- HWGCIUXHGRINBV-HLIUPHQXSA-N 1-[(3R)-1-cyanopyrrolidin-3-yl]-1-methyl-3-[4-(1-methylpyrazol-4-yl)phenyl]urea 1-[(3R)-1-cyanopyrrolidin-3-yl]-1-methyl-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C(#N)N1C[C@@H](CC1)N(C(=O)NC1=CC=C(C=C1)C(F)(F)F)C.C(#N)N1C[C@@H](CC1)N(C(=O)NC1=CC=C(C=C1)C=1C=NN(C1)C)C HWGCIUXHGRINBV-HLIUPHQXSA-N 0.000 claims 1
- LSJPCGONGCTFFW-SNVBAGLBSA-N 2-(2-chlorophenyl)-N-[(3R)-1-cyanopyrrolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound ClC1=C(C=CC=C1)C=1SC(=CN=1)C(=O)N[C@H]1CN(CC1)C#N LSJPCGONGCTFFW-SNVBAGLBSA-N 0.000 claims 1
- ZUYGZLCUQVYYHF-UHFFFAOYSA-N 2-(4-acetyl-1,4-diazepan-1-yl)-N-(1-cyanopyrrolidin-3-yl)pyridine-4-carboxamide Chemical compound C(C)(=O)N1CCN(CCC1)C=1C=C(C(=O)NC2CN(CC2)C#N)C=CN=1 ZUYGZLCUQVYYHF-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- GLFISEMLNCKZKB-GFCCVEGCSA-N 3-(1H-benzimidazol-2-yl)-N-[(3R)-1-cyanopyrrolidin-3-yl]azetidine-1-carboxamide Chemical compound N1C(=NC2=C1C=CC=C2)C1CN(C1)C(=O)N[C@H]1CN(CC1)C#N GLFISEMLNCKZKB-GFCCVEGCSA-N 0.000 claims 1
- PRSXVLVCZRHGOR-UHFFFAOYSA-N 3-(3-benzylphenyl)-1-(1-cyanopyrrolidin-3-yl)-1-methylurea 3-(3-chlorophenyl)-1-(1-cyanopyrrolidin-3-yl)-1-methylurea 1-(1-cyanopyrrolidin-3-yl)-3-(3-phenoxyphenyl)urea Chemical compound CN(C1CCN(C1)C#N)C(=O)Nc1cccc(Cl)c1.O=C(NC1CCN(C1)C#N)Nc1cccc(Oc2ccccc2)c1.CN(C1CCN(C1)C#N)C(=O)Nc1cccc(Cc2ccccc2)c1 PRSXVLVCZRHGOR-UHFFFAOYSA-N 0.000 claims 1
- ZCLHBFLSTMSYFI-UHFFFAOYSA-N 3-(3-chlorophenyl)-N-(1-cyanopyrrolidin-3-yl)-1,2-oxazole-5-carboxamide Chemical compound ClC=1C=C(C=CC=1)C1=NOC(=C1)C(=O)NC1CN(CC1)C#N ZCLHBFLSTMSYFI-UHFFFAOYSA-N 0.000 claims 1
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- WALBHSXBGAUZKG-GFCCVEGCSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-2-fluoro-4-pyrrolidin-1-ylbenzamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=C(C=C(C=C1)N1CCCC1)F)=O WALBHSXBGAUZKG-GFCCVEGCSA-N 0.000 claims 1
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- NCQUDMJRPXRBPA-CYBMUJFWSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-(1-pyrazin-2-ylpyrazol-3-yl)azetidine-1-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)N1CC(C1)C1=NN(C=C1)C1=NC=CN=C1 NCQUDMJRPXRBPA-CYBMUJFWSA-N 0.000 claims 1
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- ZIVSOTIVNKAORH-GFCCVEGCSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-(3-methoxyphenyl)-1,2-oxazole-5-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C1=CC(=NO1)C1=CC(=CC=C1)OC ZIVSOTIVNKAORH-GFCCVEGCSA-N 0.000 claims 1
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- HRRKEFUZNGSJAZ-CQSZACIVSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-(4-methoxyphenyl)azetidine-1-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)N1CC(C1)C1=CC=C(C=C1)OC HRRKEFUZNGSJAZ-CQSZACIVSA-N 0.000 claims 1
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- KAZVRNMRUXHFSH-OAHLLOKOSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-fluoro-5-(1-methylindazol-5-yl)pyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1F)C=1C=C2C=NN(C2=CC=1)C)=O KAZVRNMRUXHFSH-OAHLLOKOSA-N 0.000 claims 1
- SCWRPIOZZNFBHK-OAHLLOKOSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-fluoro-5-(1-methylpyrrolo[2,3-b]pyridin-5-yl)pyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1F)C=1C=C2C(=NC=1)N(C=C2)C)=O SCWRPIOZZNFBHK-OAHLLOKOSA-N 0.000 claims 1
- MHWJCAWDDYVIMN-CQSZACIVSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-fluoro-5-imidazo[1,2-a]pyridin-6-ylpyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1F)C=1C=CC=2N(C=1)C=CN=2)=O MHWJCAWDDYVIMN-CQSZACIVSA-N 0.000 claims 1
- LORIXYUTELMIGV-GFCCVEGCSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-fluoro-5-pyrazolo[1,5-a]pyrimidin-5-ylpyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1F)C1=NC=2N(C=C1)N=CC=2)=O LORIXYUTELMIGV-GFCCVEGCSA-N 0.000 claims 1
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- PVTURUFYCWXEGM-GOSISDBHSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-methoxy-4-(2-morpholin-4-ylpyridin-4-yl)benzamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=CC(=C(C=C1)C1=CC(=NC=C1)N1CCOCC1)OC)=O PVTURUFYCWXEGM-GOSISDBHSA-N 0.000 claims 1
- SFLXXHOKGMCFIS-CYBMUJFWSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-methoxy-4-(pyrimidin-2-ylamino)benzamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=CC(=C(C=C1)NC1=NC=CC=N1)OC)=O SFLXXHOKGMCFIS-CYBMUJFWSA-N 0.000 claims 1
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- SDSHASIAJMQRNK-SNVBAGLBSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-pyridin-2-yl-1,2-oxazole-5-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C1=CC(=NO1)C1=NC=CC=C1 SDSHASIAJMQRNK-SNVBAGLBSA-N 0.000 claims 1
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- YZDDSFXRMVHPRG-LLVKDONJSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-pyridin-3-yl-1,2-oxazole-5-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C1=CC(=NO1)C=1C=NC=CC=1 YZDDSFXRMVHPRG-LLVKDONJSA-N 0.000 claims 1
- HCGZNXDPBZKYNW-LLVKDONJSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-pyridin-3-yl-1H-pyrazole-5-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C1=NNC(=C1)C=1C=NC=CC=1 HCGZNXDPBZKYNW-LLVKDONJSA-N 0.000 claims 1
- VSOICVQVGNRJGO-LLVKDONJSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-3-pyridin-4-yl-1,2-oxazole-5-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C1=CC(=NO1)C1=CC=NC=C1 VSOICVQVGNRJGO-LLVKDONJSA-N 0.000 claims 1
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- LVATWXODBSHCTF-MRXNPFEDSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-4-(4-cyclopropylpyrimidin-2-yl)-2,3-dihydro-1,4-benzoxazine-7-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C=1C=CC2=C(OCCN2C2=NC=CC(=N2)C2CC2)C=1 LVATWXODBSHCTF-MRXNPFEDSA-N 0.000 claims 1
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- QDVVFAZLEFMOHY-CQSZACIVSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-4-fluoro-3-pyridin-4-ylbenzamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=CC(=C(C=C1)F)C1=CC=NC=C1)=O QDVVFAZLEFMOHY-CQSZACIVSA-N 0.000 claims 1
- LFGKFGRTXYUMGM-CYBMUJFWSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-5-(1,3-dimethylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1)C=1C(=NN(C=1)C)C)=O LFGKFGRTXYUMGM-CYBMUJFWSA-N 0.000 claims 1
- UKXYUWAVQXPACQ-CYBMUJFWSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-5-(1-methylpyrazol-4-yl)pyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1)C=1C=NN(C=1)C)=O UKXYUWAVQXPACQ-CYBMUJFWSA-N 0.000 claims 1
- GUPSFTJGPXXICE-OAHLLOKOSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-5-(4-fluorophenyl)pyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1)C1=CC=C(C=C1)F)=O GUPSFTJGPXXICE-OAHLLOKOSA-N 0.000 claims 1
- PHNYTORUZVDISA-OAHLLOKOSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-5-phenylpyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=NC=C(C=C1)C1=CC=CC=C1)=O PHNYTORUZVDISA-OAHLLOKOSA-N 0.000 claims 1
- HTVXMORNGLJXTB-CYBMUJFWSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(1,3-dimethylpyrazol-4-yl)-3-fluoroimidazo[1,2-a]pyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C=1N=C2N(C=C(C=C2)C=2C(=NN(C=2)C)C)C=1F HTVXMORNGLJXTB-CYBMUJFWSA-N 0.000 claims 1
- IYBSDASRAHMSFO-CQSZACIVSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(1,3-dimethylpyrazol-4-yl)imidazo[1,2-a]pyridine-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C=1N=C2N(C=C(C=C2)C=2C(=NN(C=2)C)C)C=1 IYBSDASRAHMSFO-CQSZACIVSA-N 0.000 claims 1
- JQSPDRKSPNCYJM-CQSZACIVSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C=1C=NN2C=1C=CC(=C2)C=1C=NN(C=1)C JQSPDRKSPNCYJM-CQSZACIVSA-N 0.000 claims 1
- QLKZFMMKSCFPSU-CYBMUJFWSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(1-methylpyrazol-4-yl)pyridine-3-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(C1=CN=C(C=C1)C=1C=NN(C=1)C)=O QLKZFMMKSCFPSU-CYBMUJFWSA-N 0.000 claims 1
- GPFMOHHORSUPPX-QGZVFWFLSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-methylpropyl)indazole-3-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)NC(=O)C1=NN(C2=CC(=CC=C12)C=1C(=NOC=1C)C)CC(C)C GPFMOHHORSUPPX-QGZVFWFLSA-N 0.000 claims 1
- OWJRHEASECNJSY-CYBMUJFWSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-3-fluoroimidazo[1,2-a]pyridine-2-carboxamide Chemical compound CC1=C(C(C)=NO1)C1=CN2C(F)=C(N=C2C=C1)C(=O)N[C@@H]1CCN(C1)C#N OWJRHEASECNJSY-CYBMUJFWSA-N 0.000 claims 1
- IJTONWPTRNPZBZ-CQSZACIVSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-N-methyl-1H-benzimidazole-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)N(C(=O)C1=NC2=C(N1)C=C(C=C2)C=1C(=NOC=1C)C)C IJTONWPTRNPZBZ-CQSZACIVSA-N 0.000 claims 1
- ZVTXOPLNDAQZDV-MRXNPFEDSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-N-methyl-1H-indole-2-carboxamide Chemical compound C(#N)N1C[C@@H](CC1)N(C(=O)C=1NC2=CC(=CC=C2C=1)C=1C(=NOC=1C)C)C ZVTXOPLNDAQZDV-MRXNPFEDSA-N 0.000 claims 1
- SKZLISRSNCWYST-MRXNPFEDSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-6-(3-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1CN(C[C@@H]1NC(=O)C2=C3C=CC(=CN3N=C2)C4=CC(=CC=C4)F)C#N SKZLISRSNCWYST-MRXNPFEDSA-N 0.000 claims 1
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| WO2016019237A2 (en) | 2014-07-31 | 2016-02-04 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| WO2016021629A1 (ja) | 2014-08-06 | 2016-02-11 | 塩野義製薬株式会社 | ＴｒｋＡ阻害活性を有する複素環および炭素環誘導体 |
| GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| MY188957A (en) * | 2015-03-30 | 2022-01-14 | Mission Therapeutics Ltd | 1-cyano-pyrrolidine compounds as usp30 inhibitors |
| 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 |
| 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 |
| WO2017163078A1 (en) | 2016-03-24 | 2017-09-28 | Mission Therapeutics Limited | 1-cyano-pyrrolidine derivatives as dbu inhibitors |
| JP6959332B2 (ja) * | 2016-09-27 | 2021-11-02 | ミッション セラピューティクス リミティド | Ｕｓｐ３０の阻害剤としての活性を有するシアノピロリジン誘導体 |
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