JP2019507177A5 - - Google Patents
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- Publication number
- JP2019507177A5 JP2019507177A5 JP2018546518A JP2018546518A JP2019507177A5 JP 2019507177 A5 JP2019507177 A5 JP 2019507177A5 JP 2018546518 A JP2018546518 A JP 2018546518A JP 2018546518 A JP2018546518 A JP 2018546518A JP 2019507177 A5 JP2019507177 A5 JP 2019507177A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- pyrrolidine
- carbonitrile
- dihydro
- spiro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 19
- -1 cyano, hydroxyl Chemical group 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 230000007812 deficiency Effects 0.000 claims 7
- 208000008955 Mucolipidoses Diseases 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 208000014644 Brain disease Diseases 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 201000000915 Chronic Progressive External Ophthalmoplegia Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 2
- 208000032274 Encephalopathy Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 208000006136 Leigh Disease Diseases 0.000 claims 2
- 208000017507 Leigh syndrome Diseases 0.000 claims 2
- 108010027062 Long-Chain Acyl-CoA Dehydrogenase Proteins 0.000 claims 2
- 102000018653 Long-Chain Acyl-CoA Dehydrogenase Human genes 0.000 claims 2
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 2
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 2
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 2
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000002438 mitochondrial effect Effects 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims 2
- 208000020468 mucolipidosis III alpha/beta Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- RBNHRPZXERKDHR-KRWDZBQOSA-N (3S)-7-(4-fluorophenyl)-2-oxospiro[pyrido[2,3-b][1,4]oxazine-3,3'-pyrrolidine]-1-carbonitrile Chemical compound FC1=CC=C(C=C1)C1=CC2=C(O[C@@]3(CNCC3)C(N2C#N)=O)N=C1 RBNHRPZXERKDHR-KRWDZBQOSA-N 0.000 claims 1
- PBQINQSJWPGZAX-UHFFFAOYSA-N 1,5-dihydro-4,1-benzoxazepin-2-one Chemical compound N1C(=O)COCC2=CC=CC=C21 PBQINQSJWPGZAX-UHFFFAOYSA-N 0.000 claims 1
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 1
- ORNSLMJWQDGQFF-UHFFFAOYSA-N 1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=CC=C2NC(=O)COC2=N1 ORNSLMJWQDGQFF-UHFFFAOYSA-N 0.000 claims 1
- LMORUQRSHZOMKO-UHFFFAOYSA-N 3,4-dihydro-1h-1,5-naphthyridin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=N1 LMORUQRSHZOMKO-UHFFFAOYSA-N 0.000 claims 1
- KLPUJWLQGMDXDV-UHFFFAOYSA-N 3,4-dihydro-1h-1,6-naphthyridin-2-one Chemical compound N1=CC=C2NC(=O)CCC2=C1 KLPUJWLQGMDXDV-UHFFFAOYSA-N 0.000 claims 1
- PWCQRUXZWPUNBG-UHFFFAOYSA-N 3,4-dihydro-1h-1,7-naphthyridin-2-one Chemical compound C1=NC=C2NC(=O)CCC2=C1 PWCQRUXZWPUNBG-UHFFFAOYSA-N 0.000 claims 1
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims 1
- 102000052553 3-Hydroxyacyl CoA Dehydrogenase Human genes 0.000 claims 1
- 108700020831 3-Hydroxyacyl-CoA Dehydrogenase Proteins 0.000 claims 1
- APYXDKYGQKKWDM-UHFFFAOYSA-N 7,8-dihydro-5h-pyrazino[2,3-b]pyrazin-6-one Chemical compound C1=CN=C2NC(=O)CNC2=N1 APYXDKYGQKKWDM-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 201000005943 Barth syndrome Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
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- AUYFWPWADNCLMC-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C1=CC=C(C=C1)C1=CC2=C(OC3(CN(CC3)C#N)C(N2)=O)N=C1 AUYFWPWADNCLMC-UHFFFAOYSA-N 0.000 claims 1
- AUYFWPWADNCLMC-SFHVURJKSA-N C(#N)C1=CC=C(C=C1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 Chemical compound C(#N)C1=CC=C(C=C1)C1=CC2=C(O[C@@]3(CN(CC3)C#N)C(N2)=O)N=C1 AUYFWPWADNCLMC-SFHVURJKSA-N 0.000 claims 1
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| US11059809B2 (en) | 2017-06-20 | 2021-07-13 | Mission Therapeutics Limited | Substituted cyanopyrrolidines with activity as DUB inhibitors |
| US11247987B2 (en) | 2017-10-06 | 2022-02-15 | Forma Therapeutics, Inc. | Inhibiting ubiquitin specific peptidase 30 |
| IL278291B2 (en) | 2018-05-17 | 2023-10-01 | Forma Therapeutics Inc | Fused bicyclic compounds useful as ubiquitin-specific peptidase 30 inhibitors |
| US11572374B2 (en) | 2018-08-14 | 2023-02-07 | Amgen Inc. | N-cyano-7-azanorbornane derivatives and uses thereof |
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| CN115461340A (zh) | 2020-04-08 | 2022-12-09 | 特殊治疗有限公司 | 具有作为usp30抑制剂活性的n-氰基吡咯烷类化合物 |
| WO2021239863A1 (en) | 2020-05-28 | 2021-12-02 | 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 |
| CN115698001A (zh) | 2020-06-04 | 2023-02-03 | 特殊治疗有限公司 | 具有作为usp30抑制剂活性的n-氰基吡咯烷类化合物 |
| FI4161929T3 (fi) | 2020-06-08 | 2025-07-30 | Mission Therapeutics Ltd | 1-(5-(2-syaanipyridin-4-yyli)oksatsoli-2-karbonyyli)-4-metyyliheksahydropyrrolo[3,4-b]pyrroli-5(1h)-karbonitriili usp30-inhibiittorina käytettäväksi mitokondrioiden toimintahäiriön, syövän ja fibroosin hoitamisessa |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| CN116143782B (zh) * | 2021-11-22 | 2024-04-12 | 西南大学 | 一类螺[吡咯烷-2,3'-喹啉]-2'-酮类衍生物的设计合成与应用 |
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| WO2024151847A1 (en) * | 2023-01-13 | 2024-07-18 | The University Of North Carolina At Chapel Hill | Identification of otud7b inhibitor 7bi and its application in reducing growth of nsclc and leukemia cells |
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| EP2752191A1 (en) | 2013-01-07 | 2014-07-09 | Sanofi | Compositions and methods using hdm2 antagonist and mek inhibitor |
| GB201416754D0 (en) * | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| EP3277677B9 (en) | 2015-03-30 | 2021-07-14 | Mission Therapeutics Limited | 1-cyano-pyrrolidine compounds as usp30 inhibitors |
| EP3322702B1 (en) * | 2015-07-14 | 2019-11-20 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
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