JP2020521730A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020521730A5 JP2020521730A5 JP2019561718A JP2019561718A JP2020521730A5 JP 2020521730 A5 JP2020521730 A5 JP 2020521730A5 JP 2019561718 A JP2019561718 A JP 2019561718A JP 2019561718 A JP2019561718 A JP 2019561718A JP 2020521730 A5 JP2020521730 A5 JP 2020521730A5
- Authority
- JP
- Japan
- Prior art keywords
- cyanopyrrolidine
- carbonitrile
- sulfonyl
- pyrrolidine
- benzenesulfonamide
- 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 cyano, hydroxy Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 206010016654 Fibrosis Diseases 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 230000004761 fibrosis Effects 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 208000011580 syndromic disease Diseases 0.000 claims 6
- 230000007812 deficiency Effects 0.000 claims 5
- 230000003176 fibrotic effect Effects 0.000 claims 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 3
- 239000005977 Ethylene Substances 0.000 claims 3
- 208000008955 Mucolipidoses Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 230000035772 mutation Effects 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 231100000241 scar Toxicity 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- BEEMGCAOXBWJIO-ZIAGYGMSSA-N (4aR,7aR)-4-(4-methylphenyl)sulfonyl-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound C(#N)N1C[C@@H]2[C@H](N(S(=O)(=O)C3=CC=C(C=C3)C)CCO2)C1 BEEMGCAOXBWJIO-ZIAGYGMSSA-N 0.000 claims 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- QDICTGLHTPMYLM-UHFFFAOYSA-N 1-cyano-N-(4-phenylphenyl)pyrrolidine-3-sulfonamide Chemical compound C1(=CC=C(C=C1)NS(=O)(=O)C1CN(CC1)C#N)C1=CC=CC=C1 QDICTGLHTPMYLM-UHFFFAOYSA-N 0.000 claims 2
- JIFYKOUMBCOVFM-UHFFFAOYSA-N 4-[(4-methylphenyl)methylsulfonyl]-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazine-6-carbonitrile Chemical compound CC1=CC=C(CS(=O)(=O)N2C3C(OCC2)CN(C3)C#N)C=C1 JIFYKOUMBCOVFM-UHFFFAOYSA-N 0.000 claims 2
- QTDYBTUZXLRWQJ-UHFFFAOYSA-N C(#N)N1CC(CC1)NS(=O)(=O)C1=CC=C(C=C1)C(C)C Chemical compound C(#N)N1CC(CC1)NS(=O)(=O)C1=CC=C(C=C1)C(C)C QTDYBTUZXLRWQJ-UHFFFAOYSA-N 0.000 claims 2
- SIJCHMWGIWVJAH-UHFFFAOYSA-N C(#N)N1CC(CC1)NS(=O)(=O)C1=NC=C(C=C1)C1=CC=CC=C1 Chemical compound C(#N)N1CC(CC1)NS(=O)(=O)C1=NC=C(C=C1)C1=CC=CC=C1 SIJCHMWGIWVJAH-UHFFFAOYSA-N 0.000 claims 2
- IGCJSGQUBIYSSD-UHFFFAOYSA-N C(#N)N1CC(CC1)NS(=O)(=O)C=1C=NC(=CC=1)OC1=CC=CC=C1 Chemical compound C(#N)N1CC(CC1)NS(=O)(=O)C=1C=NC(=CC=1)OC1=CC=CC=C1 IGCJSGQUBIYSSD-UHFFFAOYSA-N 0.000 claims 2
- HBAOUZBEZQZDDA-UHFFFAOYSA-N C(C1=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N Chemical compound C(C1=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N HBAOUZBEZQZDDA-UHFFFAOYSA-N 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 208000032544 Cicatrix Diseases 0.000 claims 2
- GOUNALIZYDVKHO-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N Chemical compound ClC1=CC=C(C=C1)C1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N GOUNALIZYDVKHO-UHFFFAOYSA-N 0.000 claims 2
- GOUNALIZYDVKHO-INIZCTEOSA-N ClC1=CC=C(C=C1)C1CCN(CC1)S(=O)(=O)[C@@H]1CN(CC1)C#N Chemical compound ClC1=CC=C(C=C1)C1CCN(CC1)S(=O)(=O)[C@@H]1CN(CC1)C#N GOUNALIZYDVKHO-INIZCTEOSA-N 0.000 claims 2
- GOUNALIZYDVKHO-MRXNPFEDSA-N ClC1=CC=C(C=C1)C1CCN(CC1)S(=O)(=O)[C@H]1CN(CC1)C#N Chemical compound ClC1=CC=C(C=C1)C1CCN(CC1)S(=O)(=O)[C@H]1CN(CC1)C#N GOUNALIZYDVKHO-MRXNPFEDSA-N 0.000 claims 2
- WRCNLCVEVZQITB-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1CN(C1)S(=O)(=O)C1CN(CC1)C#N Chemical compound ClC1=CC=C(C=C1)C1CN(C1)S(=O)(=O)C1CN(CC1)C#N WRCNLCVEVZQITB-UHFFFAOYSA-N 0.000 claims 2
- WRCNLCVEVZQITB-AWEZNQCLSA-N ClC1=CC=C(C=C1)C1CN(C1)S(=O)(=O)[C@@H]1CN(CC1)C#N Chemical compound ClC1=CC=C(C=C1)C1CN(C1)S(=O)(=O)[C@@H]1CN(CC1)C#N WRCNLCVEVZQITB-AWEZNQCLSA-N 0.000 claims 2
- WRCNLCVEVZQITB-CQSZACIVSA-N ClC1=CC=C(C=C1)C1CN(C1)S(=O)(=O)[C@H]1CN(CC1)C#N Chemical compound ClC1=CC=C(C=C1)C1CN(C1)S(=O)(=O)[C@H]1CN(CC1)C#N WRCNLCVEVZQITB-CQSZACIVSA-N 0.000 claims 2
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 2
- LWHZBVOWIRURSN-UHFFFAOYSA-N FC1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N Chemical compound FC1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N LWHZBVOWIRURSN-UHFFFAOYSA-N 0.000 claims 2
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- YCPRYUOSAYYWAH-UHFFFAOYSA-N N-(1-cyanopyrrolidin-3-yl)-2-phenylbenzenesulfonamide Chemical compound C(#N)N1CC(CC1)NS(=O)(=O)C=1C(=CC=CC=1)C1=CC=CC=C1 YCPRYUOSAYYWAH-UHFFFAOYSA-N 0.000 claims 2
- CWHZUYIHGGINNU-UHFFFAOYSA-N N-(1-cyanopyrrolidin-3-yl)-4-phenylbenzenesulfonamide Chemical compound C(#N)N1CC(CC1)NS(=O)(=O)C1=CC=C(C=C1)C1=CC=CC=C1 CWHZUYIHGGINNU-UHFFFAOYSA-N 0.000 claims 2
- CWHZUYIHGGINNU-MRXNPFEDSA-N N-[(3R)-1-cyanopyrrolidin-3-yl]-4-phenylbenzenesulfonamide Chemical compound C(#N)N1C[C@@H](CC1)NS(=O)(=O)C1=CC=C(C=C1)C1=CC=CC=C1 CWHZUYIHGGINNU-MRXNPFEDSA-N 0.000 claims 2
- CWHZUYIHGGINNU-INIZCTEOSA-N N-[(3S)-1-cyanopyrrolidin-3-yl]-4-phenylbenzenesulfonamide Chemical compound C(#N)N1C[C@H](CC1)NS(=O)(=O)C1=CC=C(C=C1)C1=CC=CC=C1 CWHZUYIHGGINNU-INIZCTEOSA-N 0.000 claims 2
- TWONXSWEDQMNGI-UHFFFAOYSA-N N1=C(C=CC=C1)N1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N Chemical compound N1=C(C=CC=C1)N1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N TWONXSWEDQMNGI-UHFFFAOYSA-N 0.000 claims 2
- ZSDGNUMYZTWCOB-UHFFFAOYSA-N N1=C(N=CC=C1)N1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N Chemical compound N1=C(N=CC=C1)N1CCN(CC1)S(=O)(=O)C1CN(CC1)C#N ZSDGNUMYZTWCOB-UHFFFAOYSA-N 0.000 claims 2
- TYDQESZKNCOCEH-AEFFLSMTSA-N N1=CC(=CC=C1)C1=CC=C(C=C1)S(=O)(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N Chemical compound N1=CC(=CC=C1)C1=CC=C(C=C1)S(=O)(=O)N1[C@@H]2[C@H](CC1)CN(C2)C#N TYDQESZKNCOCEH-AEFFLSMTSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 230000002438 mitochondrial effect Effects 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 102000045222 parkin Human genes 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 230000037387 scars Effects 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical group 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 208000009270 3-hydroxyacyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- 208000012260 Accidental injury Diseases 0.000 claims 1
- 208000010444 Acidosis Diseases 0.000 claims 1
- 208000007848 Alcoholism 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
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- OFYYIEBCBXHERS-UHFFFAOYSA-N C(#N)N1CC(CC1)NS(=O)(=O)C=1C=CC(=NC=1)NC(=O)C1=CC=NN1C Chemical compound C(#N)N1CC(CC1)NS(=O)(=O)C=1C=CC(=NC=1)NC(=O)C1=CC=NN1C OFYYIEBCBXHERS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 208000029147 Collagen-vascular disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims 1
- 208000011518 Danon disease Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies 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
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 201000008892 GM1 Gangliosidosis 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
- 206010019799 Hepatitis viral 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
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 241000186660 Lactobacillus Species 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000035177 MELAS Diseases 0.000 claims 1
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims 1
- 208000025370 Middle East respiratory syndrome 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
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 1
- 208000035032 Multiple sulfatase deficiency Diseases 0.000 claims 1
- KSZCMXYSKOXULY-UHFFFAOYSA-N N-(1-cyanopyrrolidin-3-yl)-4-(4-fluorophenyl)benzenesulfonamide Chemical compound C(#N)N1CC(CC1)NS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F KSZCMXYSKOXULY-UHFFFAOYSA-N 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
- 208000031481 Pathologic Constriction Diseases 0.000 claims 1
- 206010034665 Peritoneal fibrosis Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 208000032056 Radiation Fibrosis Syndrome Diseases 0.000 claims 1
- 201000007737 Retinal degeneration Diseases 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 102100038376 Serine/threonine-protein kinase PINK1, mitochondrial Human genes 0.000 claims 1
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000007950 acidosis Effects 0.000 claims 1
- 208000026545 acidosis disease Diseases 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 108090000185 alpha-Synuclein Proteins 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 201000004010 carnitine palmitoyltransferase I deficiency Diseases 0.000 claims 1
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 230000007850 degeneration 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
- 206010015037 epilepsy Diseases 0.000 claims 1
- 210000002744 extracellular matrix Anatomy 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 230000002068 genetic effect Effects 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 230000001969 hypertrophic effect Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 229940039696 lactobacillus Drugs 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
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 1
- 230000007625 mitochondrial abnormality Effects 0.000 claims 1
- 208000012268 mitochondrial disease Diseases 0.000 claims 1
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims 1
- 208000020468 mucolipidosis III alpha/beta Diseases 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- GJZYCLAGVCDSAQ-UHFFFAOYSA-N n-(1-cyanopyrrolidin-3-yl)-5-fluoro-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(F)C=C1S(=O)(=O)NC1CN(C#N)CC1 GJZYCLAGVCDSAQ-UHFFFAOYSA-N 0.000 claims 1
- FXILBKWGQQHVJE-UHFFFAOYSA-N n-(1-cyanopyrrolidin-3-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1CCN(C#N)C1 FXILBKWGQQHVJE-UHFFFAOYSA-N 0.000 claims 1
- FXILBKWGQQHVJE-SNVBAGLBSA-N n-[(3r)-1-cyanopyrrolidin-3-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N[C@@H]1CCN(C#N)C1 FXILBKWGQQHVJE-SNVBAGLBSA-N 0.000 claims 1
- FXILBKWGQQHVJE-JTQLQIEISA-N n-[(3s)-1-cyanopyrrolidin-3-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N[C@H]1CCN(C#N)C1 FXILBKWGQQHVJE-JTQLQIEISA-N 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 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
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 210000000574 retroperitoneal space Anatomy 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000004409 schistosomiasis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 208000037804 stenosis Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 230000007838 tissue remodeling Effects 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 230000000472 traumatic effect Effects 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 201000010866 very long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- 201000001862 viral hepatitis Diseases 0.000 claims 1
- 0 CB*C(C)(C)*IS(N(*)C(C*(C1)I)CN1C#N)(=O)=O Chemical compound CB*C(C)(C)*IS(N(*)C(C*(C1)I)CN1C#N)(=O)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1708652.1A GB201708652D0 (en) | 2017-05-31 | 2017-05-31 | Novel compounds and uses |
| GB1708652.1 | 2017-05-31 | ||
| PCT/GB2018/051454 WO2018220355A1 (en) | 2017-05-31 | 2018-05-30 | Sulfonamide-substituted cyanopyrrolidines with activity as dub inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020521730A JP2020521730A (ja) | 2020-07-27 |
| JP2020521730A5 true JP2020521730A5 (enExample) | 2021-07-26 |
| JP7221217B2 JP7221217B2 (ja) | 2023-02-13 |
Family
ID=59270941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019561718A Active JP7221217B2 (ja) | 2017-05-31 | 2018-05-30 | Ｄｕｂ阻害剤としての活性を有するスルホンアミド置換シアノピロリジン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US11414402B2 (enExample) |
| EP (1) | EP3630096A1 (enExample) |
| JP (1) | JP7221217B2 (enExample) |
| CN (1) | CN110678176B (enExample) |
| GB (1) | GB201708652D0 (enExample) |
| MA (1) | MA48765A (enExample) |
| WO (1) | WO2018220355A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| SG11202001684PA (en) | 2017-10-06 | 2020-03-30 | Forma Therapeutics Inc | Inhibiting ubiquitin specific peptidase 30 |
| ES2988920T3 (es) | 2018-05-17 | 2024-11-22 | Forma Therapeutics Inc | Compuestos bicíclicos fusionados útiles como inhibidores de la peptidasa 30 específica de ubiquitina |
| PL3860989T3 (pl) | 2018-10-05 | 2023-07-10 | Forma Therapeutics, Inc. | Sprzężone piroliny, które działają jako inhibitory proteazy 30 swoistej dla ubikwityny (usp30) |
| JP7473565B2 (ja) | 2019-01-28 | 2024-04-23 | ミトコンドリア エモーション， インク． | マイトフュージン活性化物質及びその使用方法 |
| JP7734917B2 (ja) | 2019-01-28 | 2025-09-08 | ミトコンドリア エモーション， インク． | トランス－４－ヒドロキシシクロヘキシルフェニルアミドマイトフュージン活性化物質及びその使用方法 |
| 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 |
| BR112022020058A2 (pt) | 2020-04-08 | 2022-11-22 | Mission Therapeutics Ltd | N-cianopirrolidinas com atividade como inibidores de usp30 |
| BR112022020644A2 (pt) | 2020-05-28 | 2022-12-06 | Mission Therapeutics Ltd | Derivados de n-(1-ciano-pirrolidin-3-il)-5-(3-(trifluorometil)fenil) oxazol-2-carboxamida e os correspondentes derivados de oxadiazol como inibidores de usp30 para o tratamento de disfunção mitocondrial |
| JP7796047B2 (ja) | 2020-06-04 | 2026-01-08 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての活性を有するｎ－シアノピロリジン |
| DK4161929T3 (da) | 2020-06-08 | 2025-08-18 | Mission Therapeutics Ltd | 1-(5-(2-cyanopyridin-4-yl)oxazol-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyrrol-5(1h)-carbonitril som usp30-hæmmer til anvendelse i behandling af mitokondriedysfunktion, cancer og fibrose |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| WO2022159566A1 (en) * | 2021-01-21 | 2022-07-28 | Icahn School Of Medicine At Mount Sinai | Benzenesulfonamide agonists of trap1 for treating organ fibrosis |
| JP2024544660A (ja) | 2021-12-01 | 2024-12-03 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての活性を有する置換ｎ－シアノピロリジン |
| 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 (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001077073A1 (en) * | 2000-04-06 | 2001-10-18 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| US6867221B2 (en) | 2001-08-30 | 2005-03-15 | Kowa Co., Ltd. | Cyclic amine compounds and pharmaceutical composition containing the same |
| EP1948597A1 (en) | 2005-10-21 | 2008-07-30 | Vertex Pharmaceuticals Incorporated | Derivatives for modulation of ion channels |
| EP2152079A4 (en) | 2007-06-04 | 2011-03-09 | Avila Therapeutics Inc | HETEROCYCLIC COMPOUNDS AND USES THEREOF |
| PE20090606A1 (es) | 2007-08-20 | 2009-06-17 | Glaxo Group Ltd | Nuevos inhibidores de catepsina c y uso |
| WO2009129370A1 (en) * | 2008-04-18 | 2009-10-22 | Glaxo Group Limited | Cathepsin c inhibitors |
| AR071480A1 (es) * | 2008-04-18 | 2010-06-23 | Glaxo Group Ltd | Compuesto de 1- ciano -3- pirrolidinil -bencenosulfonamida composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para tratar la enfermedad pulmonar obstructiva cronica (copd ) |
| PE20091888A1 (es) * | 2008-04-18 | 2010-01-17 | Glaxo Group Ltd | Inhibidores de catepsina c |
| EP2565186A1 (en) | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| CN103183673B (zh) | 2011-12-30 | 2016-09-14 | 浙江新和成股份有限公司 | (s,s)-2,8-二氮杂双环[4,3,0]壬烷的合成方法 |
| MX367085B (es) | 2013-07-31 | 2019-08-05 | Merck Patent Gmbh | Piridinas, pirimidinas y pirazinas como inhibidores de tirosina cinasa de bruton e inhibidores y usos de las mismas. |
| EP3145505A4 (en) | 2014-05-19 | 2018-02-28 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (naaa) inhibitors and their use thereof |
| EP3148572A4 (en) | 2014-05-27 | 2017-12-27 | Pharmakea, Inc. | Compositions and methods of delivery of deubiquitinase inhibitors |
| 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 |
| 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 |
| 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 |
| 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 |
-
2017
- 2017-05-31 GB GBGB1708652.1A patent/GB201708652D0/en not_active Ceased
-
2018
- 2018-05-30 MA MA048765A patent/MA48765A/fr unknown
- 2018-05-30 EP EP18730047.0A patent/EP3630096A1/en active Pending
- 2018-05-30 JP JP2019561718A patent/JP7221217B2/ja active Active
- 2018-05-30 WO PCT/GB2018/051454 patent/WO2018220355A1/en not_active Ceased
- 2018-05-30 CN CN201880035657.8A patent/CN110678176B/zh active Active
- 2018-05-30 US US16/615,040 patent/US11414402B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10435389B2 (en) | Octahydrocyclopenta[c]pyrrole allosteric inhibitors of SHP2 | |
| JP7644139B2 (ja) | インダゾール系化合物及び関連使用方法 | |
| JP7721270B2 (ja) | Ｂｒｍ標的化化合物および関連使用方法 | |
| JP2019504009A5 (enExample) | ||
| US10676479B2 (en) | Imidazolepyridine compounds and uses thereof | |
| TWI694076B (zh) | 三唑并嘧啶化合物及其用途 | |
| US8486951B2 (en) | Cyclopropane amides and analogs exhibiting anti-cancer and anti-proliferative activities | |
| JP6387360B2 (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 | |
| JP2018524367A5 (enExample) | ||
| JP2019501142A5 (enExample) | ||
| 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 | |
| JP2022550437A (ja) | Ｂｒｍ標的化化合物および関連使用方法 | |
| TW201831464A (zh) | 作為激酶抑制劑之雜環醯胺 | |
| JP2019513135A5 (enExample) | ||
| JP2019532945A5 (enExample) | ||
| EP4121167A1 (en) | Selective modulators of mutant lrrk2 proteolysis and associated methods of use | |
| US9744169B2 (en) | Compounds for treatment of fibrosis diseases | |
| CN110234646A (zh) | 靶向PROTAC的Tau蛋白及相关使用方法 | |
| JP2017508766A5 (enExample) | ||
| KR20170094263A (ko) | Ｎａｄｐｈ 옥시다제 억제제인 아미도 티아디아졸 유도체 | |
| RU2008116575A (ru) | Производные 3-циклил-2-(4-сульфамоилфенил)-n-циклилпропионамида, применимые для лечения нарушенной переносимости глюкозы и диабета | |
| JP2018510183A5 (enExample) | ||
| RU2016102137A (ru) | Первичные карбоксамиды в качестве ингибиторов bik | |
| KR20120097512A (ko) | 키나제 조절을 위한 화합물 및 방법, 및 그에 대한 적응증 | |
| JP2014037426A5 (enExample) |