JP2019532950A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019532950A5 JP2019532950A5 JP2019517227A JP2019517227A JP2019532950A5 JP 2019532950 A5 JP2019532950 A5 JP 2019532950A5 JP 2019517227 A JP2019517227 A JP 2019517227A JP 2019517227 A JP2019517227 A JP 2019517227A JP 2019532950 A5 JP2019532950 A5 JP 2019532950A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- carbonitrile
- substituted
- cyano
- 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
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 20
- -1 nitro, hydroxyl Chemical group 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000002950 monocyclic group Chemical group 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 239000011593 sulfur Chemical group 0.000 claims 8
- 208000011580 syndromic disease Diseases 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 230000007812 deficiency Effects 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 208000008955 Mucolipidoses Diseases 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- UHTNYXUUUZRSQT-UHFFFAOYSA-N 2H-1,4-oxazine-6-carbonitrile Chemical compound O1CC=NC=C1C#N UHTNYXUUUZRSQT-UHFFFAOYSA-N 0.000 claims 2
- YEHKUJCPSAWOMO-UHFFFAOYSA-N 4-[5-(2-cyanopyridin-4-yl)pyridin-2-yl]-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound C(#N)C1=NC=CC(=C1)C=1C=NC(=CC=1)N1C2C(OCC1)CN(C2)C#N YEHKUJCPSAWOMO-UHFFFAOYSA-N 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 2
- 230000002438 mitochondrial effect Effects 0.000 claims 2
- 210000003205 muscle Anatomy 0.000 claims 2
- 230000035772 mutation Effects 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- RLOLPWZMPBNNMD-SNVBAGLBSA-N (3R)-3-[methyl-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]amino]pyrrolidine-1-carbonitrile Chemical compound CN([C@H]1CN(CC1)C#N)C1=NC2=C(N1)C=C(C=C2)C(F)(F)F RLOLPWZMPBNNMD-SNVBAGLBSA-N 0.000 claims 1
- SCXBLWQUUWJKBT-YGRLFVJLSA-N (3aR,6aR)-1-(6-methoxy-1H-benzimidazol-2-yl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound COC=1C=CC2=C(NC(=N2)N2[C@@H]3[C@H](CC2)CN(C3)C#N)C=1 SCXBLWQUUWJKBT-YGRLFVJLSA-N 0.000 claims 1
- IECQERZQLRJDGS-RNCFNFMXSA-N (3aR,6aR)-1-[6-(trifluoromethoxy)-1H-benzimidazol-2-yl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound FC(OC=1C=CC2=C(NC(=N2)N2[C@@H]3[C@H](CC2)CN(C3)C#N)C=1)(F)F IECQERZQLRJDGS-RNCFNFMXSA-N 0.000 claims 1
- FSHHHOJFBYRTAO-UONOGXRCSA-N (3aS,6aS)-1-(5-phenyl-1,3-thiazol-2-yl)-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CN=C(S1)N1[C@H]2[C@@H](CC1)CN(C2)C#N FSHHHOJFBYRTAO-UONOGXRCSA-N 0.000 claims 1
- BXVKKUUGHSZIEN-ZIAGYGMSSA-N (4aR,7aR)-4-(5-phenyl-1,3-thiazol-2-yl)-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@H]2OCCN([C@@H]2C1)C1=NC=C(S1)C1=CC=CC=C1 BXVKKUUGHSZIEN-ZIAGYGMSSA-N 0.000 claims 1
- KUIFFOHZPMMCOQ-SJORKVTESA-N (4aR,7aS)-4-(4-phenylpyridin-2-yl)-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@@H]2OCCN([C@@H]2C1)C1=NC=CC(=C1)C1=CC=CC=C1 KUIFFOHZPMMCOQ-SJORKVTESA-N 0.000 claims 1
- VPYYGJSVILHEFW-CVEARBPZSA-N (4aR,7aS)-4-(4-phenylpyrimidin-2-yl)-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@@H]2OCCN([C@@H]2C1)C1=NC(=CC=N1)C1=CC=CC=C1 VPYYGJSVILHEFW-CVEARBPZSA-N 0.000 claims 1
- GKUCDXCOHJKRQW-SJORKVTESA-N (4aR,7aS)-4-(5-phenylpyridin-2-yl)-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@@H]2OCCN([C@@H]2C1)C1=NC=C(C=C1)C1=CC=CC=C1 GKUCDXCOHJKRQW-SJORKVTESA-N 0.000 claims 1
- MMDPZMJGNSAQNF-NEPJUHHUSA-N (4aR,7aS)-4-(6-fluoro-1,3-benzothiazol-2-yl)-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound FC1=CC=C2N=C(SC2=C1)N1CCO[C@H]2CN(C[C@@H]12)C#N MMDPZMJGNSAQNF-NEPJUHHUSA-N 0.000 claims 1
- YPCMJMDRFRSYQR-CVEARBPZSA-N (4aR,7aS)-4-(6-phenylpyridazin-3-yl)-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@@H]2OCCN([C@@H]2C1)C1=CC=C(N=N1)C1=CC=CC=C1 YPCMJMDRFRSYQR-CVEARBPZSA-N 0.000 claims 1
- KFIIQNCQDKTTBK-SJORKVTESA-N (4aR,7aS)-4-(6-phenylpyridin-2-yl)-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@@H]2OCCN([C@@H]2C1)C1=NC(=CC=C1)C1=CC=CC=C1 KFIIQNCQDKTTBK-SJORKVTESA-N 0.000 claims 1
- OEMBEBBVERQEKM-MSOLQXFVSA-N (4aR,7aS)-4-[3-(3-cyanophenyl)pyridin-2-yl]-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@@H]2OCCN([C@@H]2C1)C1=C(C=CC=N1)C1=CC(=CC=C1)C#N OEMBEBBVERQEKM-MSOLQXFVSA-N 0.000 claims 1
- WPJVPJGNCPMPNU-SJORKVTESA-N (4aR,7aS)-4-[5-(3-cyanophenyl)pyrimidin-2-yl]-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound N#CN1C[C@@H]2OCCN([C@@H]2C1)C1=NC=C(C=N1)C1=CC(=CC=C1)C#N WPJVPJGNCPMPNU-SJORKVTESA-N 0.000 claims 1
- GTTBBELRQHLVCE-UHFFFAOYSA-N 1-(5-phenyl-1,3-thiazol-2-yl)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CN=C(S1)N1C2C(CCC1)CN(C2)C#N GTTBBELRQHLVCE-UHFFFAOYSA-N 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- ZYSDGTUUIZBONB-UHFFFAOYSA-N 1-phenyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carbonitrile Chemical compound C1(=CC=CC=C1)N1C2C(CC1)CN(C2)C#N ZYSDGTUUIZBONB-UHFFFAOYSA-N 0.000 claims 1
- OHUIVSSPUYOFKQ-RISCZKNCSA-N 2-[(3aR,6aR)-5-cyano-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-1-yl]-3H-benzimidazole-5-carbonitrile Chemical compound N#CN1C[C@H]2CCN([C@H]2C1)C1=NC2=CC=C(C=C2N1)C#N OHUIVSSPUYOFKQ-RISCZKNCSA-N 0.000 claims 1
- NGGCAOXWXCYHOJ-UHFFFAOYSA-N 3-[(5-phenyl-1,3-thiazol-2-yl)amino]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CN=C(S1)NC1CN(CC1)C#N NGGCAOXWXCYHOJ-UHFFFAOYSA-N 0.000 claims 1
- SINNBEWNTCHRPX-UHFFFAOYSA-N 3-[methyl-(5-phenyl-1,3-thiazol-2-yl)amino]pyrrolidine-1-carbonitrile Chemical compound CN(C1CN(CC1)C#N)C=1SC(=CN=1)C1=CC=CC=C1 SINNBEWNTCHRPX-UHFFFAOYSA-N 0.000 claims 1
- JBKBOQDILPUBTP-UHFFFAOYSA-N 3-[methyl-(5-phenylpyridin-2-yl)amino]pyrrolidine-1-carbonitrile Chemical compound CN(C1CN(CC1)C#N)C1=NC=C(C=C1)C1=CC=CC=C1 JBKBOQDILPUBTP-UHFFFAOYSA-N 0.000 claims 1
- 208000009270 3-hydroxyacyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- QZIQWVCJKAINRT-UHFFFAOYSA-N 4-[5-(4-cyanopyridin-2-yl)pyridin-2-yl]-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound C(#N)C1=CC(=NC=C1)C=1C=NC(=CC=1)N1C2C(OCC1)CN(C2)C#N QZIQWVCJKAINRT-UHFFFAOYSA-N 0.000 claims 1
- 208000036022 Alpers' disease Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 108700005857 Carnitine palmitoyl transferase 1A deficiency Proteins 0.000 claims 1
- 208000005359 Carnitine palmitoyl transferase 1A deficiency Diseases 0.000 claims 1
- 108700005858 Carnitine palmitoyl transferase 2 deficiency Proteins 0.000 claims 1
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000011518 Danon disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims 1
- 208000012661 Dyskinesia 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
- 208000024658 Epilepsy syndrome Diseases 0.000 claims 1
- 208000002877 Epileptic Syndromes Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000001500 Glycogen Storage Disease Type IIb Diseases 0.000 claims 1
- 208000035148 Glycogen storage disease due to LAMP-2 deficiency Diseases 0.000 claims 1
- 206010053185 Glycogen storage disease type II 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
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin 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
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 241000186660 Lactobacillus Species 0.000 claims 1
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 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
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 1
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 1
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000035032 Multiple sulfatase deficiency Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 102100035196 POLG alternative reading frame Human genes 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000027089 Parkinsonian disease Diseases 0.000 claims 1
- 208000013234 Pearson syndrome Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 claims 1
- 102000013535 Proto-Oncogene Proteins c-bcl-2 Human genes 0.000 claims 1
- 208000002009 Pyruvate Dehydrogenase Complex Deficiency Disease Diseases 0.000 claims 1
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 102100038376 Serine/threonine-protein kinase PINK1, mitochondrial Human genes 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 230000005775 apoptotic pathway Effects 0.000 claims 1
- 210000000601 blood cell Anatomy 0.000 claims 1
- 201000004010 carnitine palmitoyltransferase I deficiency Diseases 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000006443 lactic acidosis Diseases 0.000 claims 1
- 229940039696 lactobacillus Drugs 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 231100000518 lethal Toxicity 0.000 claims 1
- 230000001665 lethal effect Effects 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims 1
- 208000020468 mucolipidosis III alpha/beta Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000003387 muscular Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 208000021090 palsy Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 102000045222 parkin Human genes 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 201000006473 pyruvate decarboxylase deficiency Diseases 0.000 claims 1
- 208000015445 pyruvate dehydrogenase deficiency Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 210000002700 urine Anatomy 0.000 claims 1
- 201000010866 very long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- 0 CN(C(*)(C(*)(C(*)(C1PN1)N(*1)C#N)[Fl]=C)C1(N)I)N Chemical compound CN(C(*)(C(*)(C(*)(C1PN1)N(*1)C#N)[Fl]=C)C1(N)I)N 0.000 description 4
- FEWMOKKABCTJJN-UHFFFAOYSA-N CCCC(CNC)CNC#N Chemical compound CCCC(CNC)CNC#N FEWMOKKABCTJJN-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1616627.4A GB201616627D0 (en) | 2016-09-30 | 2016-09-30 | Novel compounds |
| GB1616627.4 | 2016-09-30 | ||
| PCT/GB2017/052949 WO2018060742A1 (en) | 2016-09-30 | 2017-10-02 | Cyanopyrrolidine derivatives with activity as inhibitors of usp30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019532950A JP2019532950A (ja) | 2019-11-14 |
| JP2019532950A5 true JP2019532950A5 (enExample) | 2020-11-12 |
| JP7084918B2 JP7084918B2 (ja) | 2022-06-15 |
Family
ID=57571070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019517227A Active JP7084918B2 (ja) | 2016-09-30 | 2017-10-02 | 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 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US11084821B2 (enExample) |
| EP (1) | EP3519412B1 (enExample) |
| JP (1) | JP7084918B2 (enExample) |
| CN (1) | CN109790169B (enExample) |
| GB (1) | GB201616627D0 (enExample) |
| MA (1) | MA46339A (enExample) |
| WO (1) | WO2018060742A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| CN110831936B (zh) | 2017-06-20 | 2023-03-28 | 特殊治疗有限公司 | 具有dub抑制剂活性的取代氰基吡咯烷 |
| WO2019071073A1 (en) | 2017-10-06 | 2019-04-11 | Forma Therapeutics, Inc. | INHIBITION OF THE SPECIFIC PEPTIDASE OF UBIQUITIN |
| JP7399870B2 (ja) * | 2018-03-27 | 2023-12-18 | ピーティーシー セラピューティクス， インコーポレイテッド | ハンチントン病を処置するための化合物 |
| ES2988920T3 (es) * | 2018-05-17 | 2024-11-22 | Forma Therapeutics Inc | Compuestos bicíclicos fusionados útiles como inhibidores de la peptidasa 30 específica de ubiquitina |
| JP7434285B2 (ja) * | 2018-08-14 | 2024-02-20 | アムジエン・インコーポレーテツド | Ｎ－シアノ－７－アザノルボルナン誘導体及びその使用 |
| AU2019356011B2 (en) * | 2018-10-05 | 2025-02-06 | Forma Therapeutics, Inc. | Fused pyrrolines which act as Ubiquitin-Specific Protease 30 (USP30) inhibitors |
| CN120698983A (zh) | 2018-12-20 | 2025-09-26 | C4医药公司 | 靶向蛋白降解 |
| GB201905371D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201905375D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201912674D0 (en) | 2019-09-04 | 2019-10-16 | Mission Therapeutics Ltd | Novel compounds |
| MX2022012578A (es) | 2020-04-08 | 2022-11-07 | Mission Therapeutics Ltd | N-cianopirrolidinas con actividad como inhibidores de usp30. |
| EP4157834B1 (en) | 2020-05-28 | 2024-07-03 | Mission Therapeutics Limited | N-(1-cyano-pyrrolidin-3-yl)-5-(3-(trifluoromethyl)phenyl)oxazole-2-carboxamide derivatives and the corresponding oxadiazole derivatives as usp30 inhibitors for the treatment of mitochondrial dysfunction |
| IL298710A (en) | 2020-06-04 | 2023-02-01 | Mission Therapeutics Ltd | N-cyanopyrrolidines with activity as USP30 inhibitors |
| KR20230022215A (ko) | 2020-06-08 | 2023-02-14 | 미션 테라퓨틱스 엘티디 | 미토콘드리아 기능장애, 암 및 섬유증의 치료에 사용하기 위한 USP30 억제제로서 1-(5-(2-시아노피리딘-4-일)옥사졸-2-카보닐)-4-메틸헥사하이드로피롤로[3,4-b]피롤-5(1H)-카보니트릴 |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| CN118834147A (zh) * | 2021-09-22 | 2024-10-25 | 杭州天玑济世生物科技有限公司 | 一类具有萘胺结构的小分子化合物及其应用 |
| WO2023099561A1 (en) | 2021-12-01 | 2023-06-08 | Mission Therapeutics Limited | Substituted n-cyanopyrrolidines with activity as usp30 inhibitors |
| CN114877158B (zh) * | 2022-04-15 | 2023-06-23 | 四川轻化工大学 | 一种非开挖原位修复管道用内衬管表面改性方法 |
| GB202408928D0 (en) | 2024-06-21 | 2024-08-07 | Mission Therapeutics Ltd | Novel compounds |
| GB202411060D0 (en) | 2024-07-29 | 2024-09-11 | Mission Therapeutics Ltd | Novel compounds |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001077073A1 (en) | 2000-04-06 | 2001-10-18 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| EP2152079A4 (en) | 2007-06-04 | 2011-03-09 | Avila Therapeutics Inc | HETEROCYCLIC COMPOUNDS AND USES THEREOF |
| WO2009129370A1 (en) * | 2008-04-18 | 2009-10-22 | Glaxo Group Limited | Cathepsin c inhibitors |
| CL2009000915A1 (es) | 2008-04-18 | 2010-04-16 | Glaxo Group Ltd | Compuestos derivados de 1-ciano-3-pirrolidinil-bencenosulfonamidas, inhibidores de catepsina c; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento de una enfermedad pulmonar obstructiva cronica (copd). |
| AR071369A1 (es) | 2008-04-18 | 2010-06-16 | Glaxo Group Ltd | Compuesto de 1- ciano-3-pirrolidinil-n-sustituido-sulfonamida, su uso para preparar un medicamento util para tratar una enfermedad pulmonar obstructiva cronica y composicion farmaceutica que lo comprende |
| EP2565186A1 (en) | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| CA2883480A1 (en) * | 2012-09-17 | 2014-03-20 | F. Hoffmann-La Roche Ag | Usp30 inhibitors and methods of use |
| BR112015009624A2 (pt) | 2012-11-02 | 2017-11-14 | Pfizer | inibidores de tirosina cinase de bruton |
| GB201309085D0 (en) | 2013-05-20 | 2013-07-03 | Redx Pharma Ltd | Compounds |
| PT3049417T (pt) | 2013-07-31 | 2019-01-24 | Merck Patent Gmbh | Piridinas, pirimidinas e pirazinas, como inibidores de btk e utilizações das mesmas |
| US9868736B2 (en) * | 2013-10-10 | 2018-01-16 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
| RU2019131017A (ru) * | 2013-10-21 | 2019-11-25 | Мерк Патент Гмбх | Соединения гетероарила в качестве ингибиторов btk и их применение |
| GB201404987D0 (en) | 2014-03-20 | 2014-05-07 | Redx Pharma Ltd | Compounds |
| WO2015179190A1 (en) | 2014-05-19 | 2015-11-26 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (naaa) inhibitors and their use thereof |
| WO2016004272A1 (en) * | 2014-07-02 | 2016-01-07 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| WO2016019237A2 (en) | 2014-07-31 | 2016-02-04 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| TN2017000158A1 (en) | 2014-10-24 | 2018-10-19 | Bristol Myers Squibb Co | Carbazole derivatives |
| PT3461821T (pt) * | 2014-10-24 | 2020-08-05 | Bristol Myers Squibb Co | Compostos de indol carboxamida úteis como inibidores de quinase |
| HRP20210791T2 (hr) * | 2015-03-30 | 2021-12-10 | Mission Therapeutics Limited | 1-cijano-pirolidin spojevi kao usp30 inhibitori |
| WO2016192074A1 (en) | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Btk inhibitors |
| CN107849013B (zh) | 2015-07-14 | 2022-03-29 | 特殊治疗有限公司 | 作为dub抑制剂用于治疗癌症的氰基吡咯烷类 |
| 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 |
| 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 |
| TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| CN110831936B (zh) | 2017-06-20 | 2023-03-28 | 特殊治疗有限公司 | 具有dub抑制剂活性的取代氰基吡咯烷 |
-
2016
- 2016-09-30 GB GBGB1616627.4A patent/GB201616627D0/en not_active Ceased
-
2017
- 2017-10-02 MA MA046339A patent/MA46339A/fr unknown
- 2017-10-02 CN CN201780060487.4A patent/CN109790169B/zh active Active
- 2017-10-02 WO PCT/GB2017/052949 patent/WO2018060742A1/en not_active Ceased
- 2017-10-02 JP JP2019517227A patent/JP7084918B2/ja active Active
- 2017-10-02 EP EP17780195.8A patent/EP3519412B1/en active Active
- 2017-10-02 US US16/336,202 patent/US11084821B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019532950A5 (enExample) | ||
| JP2019533659A5 (enExample) | ||
| JP2019532945A5 (enExample) | ||
| KR101686685B1 (ko) | 피라졸로피리미딘 ｊａｋ 억제제 화합물 및 방법 | |
| Balderas-Renteria et al. | Anticancer drug design using scaffolds of β-lactams, sulfonamides, quinoline, quinoxaline and natural products. Drugs advances in clinical trials | |
| JP2019532938A5 (enExample) | ||
| TWI839363B (zh) | 嘧啶化合物及包括其之供預防或治療癌症的藥學組成物 | |
| US9062046B2 (en) | Substituted imidazoquinoline derivatives as kinase inhibitors | |
| JP2019501142A5 (enExample) | ||
| JP2019504009A5 (enExample) | ||
| JP2019509274A5 (enExample) | ||
| JP2018510183A5 (enExample) | ||
| NZ594405A (en) | New adenosine receptor ligands and uses thereof | |
| US11180495B2 (en) | Nitrogen heteroaryl derivative having CSF1R inhibitory activity, and preparation method therefor and application thereof | |
| JP2016514124A (ja) | 変異ｉｄｈの阻害薬としての３−ピリミジン−４−イル−オキサゾリジン−２−オン | |
| TW201014851A (en) | Organic compounds | |
| CA2992981C (en) | Aminonaphthoquinone compounds and pharmaceutical composition for blocking ubiquitination-proteasome system in diseases | |
| US10870639B2 (en) | Pyrimidine compounds and pharmaceutical compositions for preventing or treating cancers including the same | |
| TWI523856B (zh) | BCR-ABL kinase inhibitor and its application | |
| Musumeci et al. | Pyrrolo [2, 3-d] pyrimidines as kinase inhibitors | |
| PH12016502293B1 (en) | Naphthyridinedione derivatives | |
| US10975082B2 (en) | Inhibitor of FLT3 kinase and use thereof | |
| US10266535B2 (en) | Inhibitor of FLT3 kinase and use thereof | |
| Hu et al. | Design, synthesis, and biological activity of 4-(imidazo [1, 2-b] pyridazin-3-yl)-1H-pyrazol-1-yl-phenylbenzamide derivatives as BCR–ABL kinase inhibitors | |
| Zhao et al. | Insights into the structural features essential for JAK2 inhibition and selectivity |