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 (33)
| 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 |
| 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 |
| MA43753A (fr) | 2016-03-24 | 2018-11-28 | Mission Therapeutics Ltd | Dérivés 1-cyano-pyrrolidine comme inhibiteurs de dbu |
| ES2850349T3 (es) | 2016-09-27 | 2021-08-27 | Mission Therapeutics Ltd | Derivados de cianopirrolidina con actividad como inhibidores de USP30 |
| GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| 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 |
| 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 |
| AU2018346597B2 (en) | 2017-10-06 | 2023-07-13 | Forma Therapeutics, Inc. | Inhibiting Ubiquitin Specific Peptidase 30 |
| BR112020019373A2 (pt) * | 2018-03-27 | 2020-12-29 | Ptc Therapeutics, Inc. | Compostos para o tratamento da doença de hutington |
| IL278291B2 (en) | 2018-05-17 | 2023-10-01 | Forma Therapeutics Inc | Condensed bicyclic compounds are useful as ubiquitin-specific peptidase 30 inhibitors |
| EP3837262B1 (en) | 2018-08-14 | 2026-06-17 | Amgen Inc. | N-cyano-7-azanorbornane derivatives and uses thereof |
| EP4218934B1 (en) * | 2018-10-05 | 2025-06-18 | Forma Therapeutics, Inc. | Inhibiting ubiquitin-specific protease 30 (usp30) |
| EP3897631A4 (en) | 2018-12-20 | 2022-11-23 | C4 Therapeutics, Inc. | TARGETED PROTEIN BREAKDOWN |
| 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 |
| 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. |
| KR20230016674A (ko) | 2020-05-28 | 2023-02-02 | 미션 테라퓨틱스 엘티디 | 미토콘드리아 기능장애의 치료를 위한 usp30 억제제로서 n-(1-시아노피롤리딘-3-일)-5-(3-(트라이플루오로메틸)페닐)옥사졸-2-카복스아미드 유도체 및 상응하는 옥사다이아졸 유도체 |
| WO2021245186A1 (en) | 2020-06-04 | 2021-12-09 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
| RS67140B1 (sr) | 2020-06-08 | 2025-09-30 | Mission Therapeutics Ltd | 1-(5-(2-cijanopiridin-4-il)oksazol-2-karbonil)-4-metilheksahidropirolo[3,4-b]pirol-5(1h)-karbonitril kao usp30 inhibitor za primenu u lečenju mitohondrijske disfunkcije, kancera i fibroze |
| 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 |
| GB202500610D0 (en) | 2025-01-16 | 2025-03-05 | Mission Therapeutics Ltd | Novel compounds |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003530384A (ja) | 2000-04-06 | 2003-10-14 | メルク フロスト カナダ アンド カンパニー | カテプシンシステインプロテアーゼ阻害薬 |
| US8242271B2 (en) | 2007-06-04 | 2012-08-14 | Avila Therapeutics, Inc. | Heterocyclic compounds and uses thereof |
| UY31771A1 (es) | 2008-04-18 | 2009-09-30 | Inhibidores de catepsina c | |
| WO2009129370A1 (en) * | 2008-04-18 | 2009-10-22 | Glaxo Group Limited | Cathepsin c inhibitors |
| UY31770A1 (es) | 2008-04-18 | 2009-09-30 | Inhibidores de catepsina c | |
| EP2565186A1 (en) | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| CN110317811A (zh) * | 2012-09-17 | 2019-10-11 | 霍夫曼-拉罗奇有限公司 | Usp30抑制剂及其使用方法 |
| US20150291554A1 (en) | 2012-11-02 | 2015-10-15 | Pfizer Inc. | Bruton's Tyrosine Kinase Inhibitors |
| GB201309085D0 (en) | 2013-05-20 | 2013-07-03 | Redx Pharma Ltd | Compounds |
| JP6612751B2 (ja) | 2013-07-31 | 2019-11-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｂｔｋの阻害剤としてのピリジン、ピリミジン及びピラジンならびにその使用 |
| US9868736B2 (en) * | 2013-10-10 | 2018-01-16 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
| US10329270B2 (en) * | 2013-10-21 | 2019-06-25 | Merck Patent Gmbh | Heteroaryl compounds as BTK inhibitors and uses thereof |
| GB201404987D0 (en) | 2014-03-20 | 2014-05-07 | Redx Pharma Ltd | Compounds |
| US9963444B2 (en) | 2014-05-19 | 2018-05-08 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (NAAA) inhibitors and their use thereof |
| WO2016004305A2 (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 |
| TWI676618B (zh) | 2014-10-24 | 2019-11-11 | 美商必治妥美雅史谷比公司 | 三環化合物 |
| MX393057B (es) | 2014-10-24 | 2025-03-24 | Bristol Myers Squibb Co | Compuestos de indol carboxamida útiles como inhibidores de cinasas. |
| LT3277677T (lt) * | 2015-03-30 | 2021-05-25 | Mission Therapeutics Limited | 1-ciano-pirolidino junginiai kaip usp30 inhibitoriai |
| WO2016192074A1 (en) | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Btk inhibitors |
| EP3322702B1 (en) | 2015-07-14 | 2019-11-20 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
| GB201521109D0 (en) * | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
| GB201522267D0 (en) * | 2015-12-17 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201522768D0 (en) * | 2015-12-23 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201602854D0 (en) | 2016-02-18 | 2016-04-06 | Mission Therapeutics Ltd | Novel compounds |
| GB201603779D0 (en) | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201604647D0 (en) * | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| MA43753A (fr) * | 2016-03-24 | 2018-11-28 | Mission Therapeutics Ltd | Dérivés 1-cyano-pyrrolidine comme inhibiteurs de dbu |
| ES2850349T3 (es) | 2016-09-27 | 2021-08-27 | Mission Therapeutics Ltd | Derivados de cianopirrolidina con actividad como inhibidores de USP30 |
| GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| 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 |
| 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 |
-
2016
- 2016-09-30 GB GBGB1616627.4A patent/GB201616627D0/en not_active Ceased
-
2017
- 2017-10-02 JP JP2019517227A patent/JP7084918B2/ja active Active
- 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 EP EP17780195.8A patent/EP3519412B1/en active Active
- 2017-10-02 US US16/336,202 patent/US11084821B2/en active Active
- 2017-10-02 MA MA046339A patent/MA46339A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019533659A5 (enExample) | ||
| JP2019532945A5 (enExample) | ||
| Balderas-Renteria et al. | Anticancer drug design using scaffolds of β-lactams, sulfonamides, quinoline, quinoxaline and natural products. Drugs advances in clinical trials | |
| KR101686685B1 (ko) | 피라졸로피리미딘 ｊａｋ 억제제 화합물 및 방법 | |
| 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 | |
| SG11202110502PA (en) | Protein tyrosine phosphatase inhibitors | |
| JP2019532938A5 (enExample) | ||
| JP5199882B2 (ja) | 高−増殖性障害及び脈管形成と関連する疾患の処置のために有用な置換４−アミノ−ピロロトリアジン誘導体 | |
| US9062046B2 (en) | Substituted imidazoquinoline derivatives as kinase inhibitors | |
| JP2019501142A5 (enExample) | ||
| JP2019504009A5 (enExample) | ||
| JP2019509274A5 (enExample) | ||
| JP2018510183A5 (enExample) | ||
| NZ608718A (en) | Imidazo[1,2-b]pyridazine and imidazo[4,5-b]pyridine derivatives as jak inhibitors | |
| NZ594405A (en) | New adenosine receptor ligands and uses thereof | |
| US10266535B2 (en) | Inhibitor of FLT3 kinase and use thereof | |
| CA2992981C (en) | Aminonaphthoquinone compounds and pharmaceutical composition for blocking ubiquitination-proteasome system in diseases | |
| JP2018525375A5 (enExample) | ||
| JP2019532950A (ja) | 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 | |
| CA2828478A1 (en) | Serine/threonine kinase inhibitors | |
| 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 | |
| Musumeci et al. | Pyrrolo [2, 3-d] pyrimidines as kinase inhibitors | |
| PH12016502293B1 (en) | Naphthyridinedione derivatives | |
| WO2015058661A1 (zh) | Bcr-abl激酶抑制剂及其应用 |