JP2019532938A5 - - Google Patents
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- Publication number
- JP2019532938A5 JP2019532938A5 JP2019516193A JP2019516193A JP2019532938A5 JP 2019532938 A5 JP2019532938 A5 JP 2019532938A5 JP 2019516193 A JP2019516193 A JP 2019516193A JP 2019516193 A JP2019516193 A JP 2019516193A JP 2019532938 A5 JP2019532938 A5 JP 2019532938A5
- Authority
- JP
- Japan
- Prior art keywords
- cyanopyrrolidine
- acetamide
- alkoxy
- azetidine
- alkyl
- 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
- -1 nitro, hydroxyl Chemical group 0.000 claims 52
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 208000011580 syndromic disease Diseases 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 230000007812 deficiency Effects 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 208000008955 Mucolipidoses Diseases 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 206010009944 Colon cancer 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
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 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
- 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
- 125000003003 spiro group Chemical group 0.000 claims 2
- UUQDJBKHLYLCFD-CZUORRHYSA-N (3S)-3-[(2R)-1-[3-(4-cyanophenyl)azetidin-1-yl]-1-oxopropan-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1CN(C1)C([C@H](C)[C@H]1CN(CC1)C#N)=O UUQDJBKHLYLCFD-CZUORRHYSA-N 0.000 claims 1
- UUQDJBKHLYLCFD-XJKSGUPXSA-N (3S)-3-[(2S)-1-[3-(4-cyanophenyl)azetidin-1-yl]-1-oxopropan-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1CN(C1)C([C@@H](C)[C@H]1CN(CC1)C#N)=O UUQDJBKHLYLCFD-XJKSGUPXSA-N 0.000 claims 1
- OBYZNAAMRLKAHI-LBPRGKRZSA-N (3S)-3-[2-[3-(2-fluoro-3-methoxyphenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound FC1=C(C=CC=C1OC)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O OBYZNAAMRLKAHI-LBPRGKRZSA-N 0.000 claims 1
- IVOTXJWFZYQFCO-AWEZNQCLSA-N (3S)-3-[2-[3-(3-cyanophenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O IVOTXJWFZYQFCO-AWEZNQCLSA-N 0.000 claims 1
- NLUWQVAMHXXCDH-AWEZNQCLSA-N (3S)-3-[2-[3-(4-cyano-3-methylphenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=C(C=C(C=C1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O)C NLUWQVAMHXXCDH-AWEZNQCLSA-N 0.000 claims 1
- HREHZCZXJKQSKD-AWEZNQCLSA-N (3S)-3-[2-[3-(4-cyanophenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O HREHZCZXJKQSKD-AWEZNQCLSA-N 0.000 claims 1
- ORKDWGOHENYQPI-ZDUSSCGKSA-N (3S)-3-[2-[3-(4-methoxyphenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound COC1=CC=C(C=C1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O ORKDWGOHENYQPI-ZDUSSCGKSA-N 0.000 claims 1
- KMZSCDNRMLSZIP-HNNXBMFYSA-N (3S)-3-[2-[3-[4-(2-methoxyethoxy)phenyl]azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound COCCOC1=CC=C(C=C1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O KMZSCDNRMLSZIP-HNNXBMFYSA-N 0.000 claims 1
- QWGFQAKJRWIWLU-AWEZNQCLSA-N (3S)-3-[2-[3-[4-methoxy-3-(1H-pyrazol-5-yl)phenyl]azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound COC1=C(C=C(C=C1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O)C1=CC=NN1 QWGFQAKJRWIWLU-AWEZNQCLSA-N 0.000 claims 1
- HUYIBNKTKQMJBQ-HNNXBMFYSA-N (3S)-3-[2-[3-[4-methoxy-3-(2-methylpyrazol-3-yl)phenyl]azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound COC1=C(C=C(C=C1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O)C1=CC=NN1C HUYIBNKTKQMJBQ-HNNXBMFYSA-N 0.000 claims 1
- VUEWGNVFAGRIAI-AWEZNQCLSA-N (3S)-3-[2-oxo-2-[3-(5-propan-2-yloxypyridin-2-yl)azetidin-1-yl]ethyl]pyrrolidine-1-carbonitrile Chemical compound C(C)(C)OC=1C=CC(=NC=1)C1CN(C1)C(C[C@H]1CN(CC1)C#N)=O VUEWGNVFAGRIAI-AWEZNQCLSA-N 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 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
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims 1
- SRASKPJBHKNSRL-UHFFFAOYSA-N 2-(1-cyanopyrrolidin-3-yl)-N-(2-phenylethyl)acetamide Chemical compound C(#N)N1CC(CC1)CC(=O)NCCC1=CC=CC=C1 SRASKPJBHKNSRL-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- ZPKYHZNBILANFJ-UHFFFAOYSA-N 3-[2-[3-(2-methylpyridin-4-yl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound CC1=NC=CC(=C1)C1CN(C1)C(CC1CN(CC1)C#N)=O ZPKYHZNBILANFJ-UHFFFAOYSA-N 0.000 claims 1
- XLKWTKAHXKPHGV-UHFFFAOYSA-N 3-[2-[3-(3,4-difluorophenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound FC=1C=C(C=CC=1F)C1CN(C1)C(CC1CN(CC1)C#N)=O XLKWTKAHXKPHGV-UHFFFAOYSA-N 0.000 claims 1
- KIXBWBXOMKSLCW-UHFFFAOYSA-N 3-[2-[3-(3-methoxyphenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound COC=1C=C(C=CC=1)C1CN(C1)C(CC1CN(CC1)C#N)=O KIXBWBXOMKSLCW-UHFFFAOYSA-N 0.000 claims 1
- YNVVVXSPWFMQKP-UHFFFAOYSA-N 3-[2-[3-(4-hydroxyphenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound OC1=CC=C(C=C1)C1CN(C1)C(CC1CN(CC1)C#N)=O YNVVVXSPWFMQKP-UHFFFAOYSA-N 0.000 claims 1
- ORKDWGOHENYQPI-UHFFFAOYSA-N 3-[2-[3-(4-methoxyphenyl)azetidin-1-yl]-2-oxoethyl]pyrrolidine-1-carbonitrile Chemical compound COC1=CC=C(C=C1)C1CN(C1)C(CC1CN(CC1)C#N)=O ORKDWGOHENYQPI-UHFFFAOYSA-N 0.000 claims 1
- MSTJQLWIQKLIBX-UHFFFAOYSA-N 3-[2-[3-(4-methoxyphenyl)azetidin-1-yl]-2-oxoethylidene]pyrrolidine-1-carbonitrile Chemical compound COC1=CC=C(C=C1)C1CN(C1)C(C=C1CN(CC1)C#N)=O MSTJQLWIQKLIBX-UHFFFAOYSA-N 0.000 claims 1
- LOOVWGPXPRGBFR-UHFFFAOYSA-N 3-[2-oxo-2-(3-phenoxyazetidin-1-yl)ethyl]pyrrolidine-1-carbonitrile Chemical compound O=C(CC1CN(CC1)C#N)N1CC(C1)OC1=CC=CC=C1 LOOVWGPXPRGBFR-UHFFFAOYSA-N 0.000 claims 1
- LWKQVPPTSGJAQD-UHFFFAOYSA-N 3-[2-oxo-2-(3-phenylazetidin-1-yl)ethylidene]pyrrolidine-1-carbonitrile Chemical compound O=C(C=C1CN(CC1)C#N)N1CC(C1)C1=CC=CC=C1 LWKQVPPTSGJAQD-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 208000009270 3-hydroxyacyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- JUWHJTKPALEDBO-AWEZNQCLSA-N 4-[1-[2-[(3S)-1-cyanopyrrolidin-3-yl]acetyl]azetidin-3-yl]-N,N-dimethylbenzamide Chemical compound C(#N)N1C[C@@H](CC1)CC(=O)N1CC(C1)C1=CC=C(C(=O)N(C)C)C=C1 JUWHJTKPALEDBO-AWEZNQCLSA-N 0.000 claims 1
- DXTDIMLMAZSPBY-LBPRGKRZSA-N 6-[1-[2-[(3S)-1-cyanopyrrolidin-3-yl]acetyl]azetidin-3-yl]pyridine-3-carbonitrile Chemical compound C(#N)N1C[C@@H](CC1)CC(=O)N1CC(C1)C1=NC=C(C#N)C=C1 DXTDIMLMAZSPBY-LBPRGKRZSA-N 0.000 claims 1
- 208000023434 Alpers-Huttenlocher syndrome Diseases 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
- 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
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 206010058892 Carnitine deficiency 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
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms 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
- 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
- 208000009796 Gangliosidoses 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
- 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
- 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
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 1
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000021908 Myocardial disease Diseases 0.000 claims 1
- OBNZTEUSEIKFEG-UHFFFAOYSA-N N-(1,3-benzothiazol-2-yl)-2-(1-cyanopyrrolidin-3-ylidene)-N-methylacetamide Chemical compound S1C(=NC2=C1C=CC=C2)N(C(C=C1CN(CC1)C#N)=O)C OBNZTEUSEIKFEG-UHFFFAOYSA-N 0.000 claims 1
- BACDKUJPGLDBGQ-UHFFFAOYSA-N N-(1-cyanopyrrolidin-3-yl)acetamide Chemical compound C(C)(=O)NC1CN(CC1)C#N BACDKUJPGLDBGQ-UHFFFAOYSA-N 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
- 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
- 201000007737 Retinal degeneration 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
- 208000006011 Stroke Diseases 0.000 claims 1
- 102000005262 Sulfatase Human genes 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 108090000185 alpha-Synuclein Proteins 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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 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
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 230000007423 decrease Effects 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
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
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- 239000000835 fiber Substances 0.000 claims 1
- 201000006440 gangliosidosis Diseases 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 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
- 201000005202 lung cancer Diseases 0.000 claims 1
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- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 230000008774 maternal effect Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 1
- 201000011540 mitochondrial DNA depletion syndrome 4a Diseases 0.000 claims 1
- 230000004065 mitochondrial dysfunction Effects 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
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- 230000000750 progressive effect Effects 0.000 claims 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 201000006473 pyruvate decarboxylase deficiency Diseases 0.000 claims 1
- 208000015445 pyruvate dehydrogenase deficiency Diseases 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
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- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 208000014001 urinary system disease Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1616348.7 | 2016-09-27 | ||
| GBGB1616348.7A GB201616348D0 (en) | 2016-09-27 | 2016-09-27 | Novel compounds |
| GBGB1709919.3A GB201709919D0 (en) | 2017-06-21 | 2017-06-21 | Novel compounds |
| GB1709919.3 | 2017-06-21 | ||
| PCT/GB2017/052880 WO2018060689A1 (en) | 2016-09-27 | 2017-09-27 | Cyanopyrrolidine derivatives with activity as inhibitors of usp30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019532938A JP2019532938A (ja) | 2019-11-14 |
| JP2019532938A5 true JP2019532938A5 (cg-RX-API-DMAC7.html) | 2020-11-12 |
| JP6959332B2 JP6959332B2 (ja) | 2021-11-02 |
Family
ID=60020244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019516193A Active JP6959332B2 (ja) | 2016-09-27 | 2017-09-27 | 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 (6)
| Country | Link |
|---|---|
| US (1) | US11014912B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3519385B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6959332B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN109790112B (cg-RX-API-DMAC7.html) |
| ES (1) | ES2850349T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2018060689A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6708661B2 (ja) | 2015-03-30 | 2020-06-10 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての１−シアノ−ピロリジン化合物 |
| GB201521109D0 (en) | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
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| SMT202500343T1 (it) | 2020-06-08 | 2025-11-10 | Mission Therapeutics Ltd | 1-(5-(2-cianopiridin-4-il)ossazol-2-carbonil)-4-metilesaidropirrolo[3,4-b]pirrol-5(1h)-carbonitrile come inibitore di usp30 per l’uso nel trattamento di disfunzione mitocondriale, cancro e fibrosi |
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| 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 |
| US11014912B2 (en) | 2016-09-27 | 2021-05-25 | Mission Therapeutics Limited | Cyanopyrrolidine derivatives with activity as inhibitors of USP30 |
| GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| GB201616627D0 (en) | 2016-09-30 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| EP3642196B1 (en) | 2017-06-20 | 2022-08-17 | Mission Therapeutics Limited | Substituted cyanopyrrolidines with activity as dub inhibitors |
-
2017
- 2017-09-27 US US16/334,836 patent/US11014912B2/en active Active
- 2017-09-27 EP EP17780147.9A patent/EP3519385B1/en active Active
- 2017-09-27 WO PCT/GB2017/052880 patent/WO2018060689A1/en not_active Ceased
- 2017-09-27 JP JP2019516193A patent/JP6959332B2/ja active Active
- 2017-09-27 ES ES17780147T patent/ES2850349T3/es active Active
- 2017-09-27 CN CN201780059123.4A patent/CN109790112B/zh active Active
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