IL260701B - Use of certain sgc stimulators and salts thereof in the preparation of medicaments for the treatment of nonalcoholic steatohepatitis (nash) - Google Patents
Use of certain sgc stimulators and salts thereof in the preparation of medicaments for the treatment of nonalcoholic steatohepatitis (nash)Info
- Publication number
- IL260701B IL260701B IL260701A IL26070118A IL260701B IL 260701 B IL260701 B IL 260701B IL 260701 A IL260701 A IL 260701A IL 26070118 A IL26070118 A IL 26070118A IL 260701 B IL260701 B IL 260701B
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- ring
- pharmaceutically acceptable
- acceptable salt
- sgc stimulator
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 127
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 title claims description 103
- 238000011282 treatment Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 13
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 title description 100
- 239000000021 stimulant Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 215
- 150000001875 compounds Chemical class 0.000 claims description 154
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 137
- 229940127296 soluble guanylate cyclase stimulator Drugs 0.000 claims description 136
- 229910052736 halogen Inorganic materials 0.000 claims description 133
- 150000002367 halogens Chemical group 0.000 claims description 130
- -1 meglinatide Chemical compound 0.000 claims description 119
- 239000003814 drug Substances 0.000 claims description 106
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 102
- 125000001931 aliphatic group Chemical group 0.000 claims description 102
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 239000001257 hydrogen Substances 0.000 claims description 90
- 210000004185 liver Anatomy 0.000 claims description 68
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 66
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 65
- 229940124597 therapeutic agent Drugs 0.000 claims description 65
- 239000008194 pharmaceutical composition Substances 0.000 claims description 54
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
- 206010016654 Fibrosis Diseases 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 230000009467 reduction Effects 0.000 claims description 26
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 229940079593 drug Drugs 0.000 claims description 23
- 230000007882 cirrhosis Effects 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 231100000240 steatosis hepatitis Toxicity 0.000 claims description 17
- 239000003112 inhibitor Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
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- 230000002159 abnormal effect Effects 0.000 claims description 13
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- YSDQQAXHVYUZIW-QCIJIYAXSA-N Liraglutide Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)CC[C@H](NC(=O)CCCCCCCCCCCCCCC)C(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 YSDQQAXHVYUZIW-QCIJIYAXSA-N 0.000 claims description 7
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
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- 239000000194 fatty acid Substances 0.000 claims description 7
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
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- 230000004580 weight loss Effects 0.000 claims description 6
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 5
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- HTQBXNHDCUEHJF-XWLPCZSASA-N Exenatide Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 HTQBXNHDCUEHJF-XWLPCZSASA-N 0.000 claims description 5
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| US10844064B2 (en) * | 2014-09-17 | 2020-11-24 | Cyclerion Therapeutics, Inc. | sGC stimulators |
| WO2017107052A1 (en) | 2015-12-22 | 2017-06-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase stimulators |
| US11357777B2 (en) | 2016-02-01 | 2022-06-14 | Cyclerion Therapeutics, Inc. | Use of sGC stimulators for the treatment of nonalcoholic steatohepatitis (NASH) |
| CN110831593A (zh) * | 2017-06-14 | 2020-02-21 | 特维娜有限公司 | 用于调节s1p1活性的化合物及其使用方法 |
| WO2019055859A1 (en) * | 2017-09-14 | 2019-03-21 | Ironwood Pharmaceuticals, Inc. | TREATMENT OF METABOLIC SYNDROME BY SGC STIMULATOR |
| US12220414B2 (en) * | 2018-07-11 | 2025-02-11 | Tisento Therapeutics Inc. | Use of sGC stimulators for the treatment of mitochondrial disorders |
| AU2019301887A1 (en) * | 2018-07-12 | 2021-01-07 | Boehringer Ingelheim International Gmbh | Alkoxy pyrazoles as soluble guanylate cyclase activators |
| WO2021073643A1 (zh) * | 2019-10-18 | 2021-04-22 | 正大天晴药业集团股份有限公司 | 用于治疗非酒精性脂肪性肝炎的药物 |
| MX2022005766A (es) | 2019-11-19 | 2022-08-08 | Trevena Inc | Compuestos y métodos para la preparación de compuestos moduladores de esfingosina 1-fosfato tipo 1 (s1p1). |
| CA3170507A1 (en) * | 2020-02-21 | 2021-08-26 | Universiteit Maastricht | Use of a soluble guanylate cyclase (sgc) stimulator or of a combination of a sgc stimulator and an sgc activator for conditions wherein the heme group of sgc is oxidized or wherein sgc is deficient in heme |
| CN118525022A (zh) * | 2022-01-27 | 2024-08-20 | 西藏海思科制药有限公司 | 一种氮杂并环衍生物及其在医药上的应用 |
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| WO2011056511A2 (en) * | 2009-10-26 | 2011-05-12 | Auspex Pharmaceuticals, Inc. | 4,6-diaminopyrimidine stimulators of soluble guanylate cyclase |
| WO2016014463A1 (en) * | 2014-07-22 | 2016-01-28 | Boehringer Ingelheim International Gmbh | Heterocyclic carboxylic acids as activators of soluble guanylate cyclase |
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| DE10109861A1 (de) | 2001-03-01 | 2002-09-05 | Bayer Ag | Neuartige seitenkettenhalogenierte Aminodicarbonsäurederivate |
| WO2008124505A2 (en) * | 2007-04-05 | 2008-10-16 | Ironwood Pharmaceuticals,Inc. | Soluble guanylate cyclase (sgc) modulators for treatment of lipid related disorders |
| CN102056907B (zh) | 2008-04-04 | 2014-12-31 | 武田药品工业株式会社 | 杂环衍生物及其用途 |
| DE102010021637A1 (de) * | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| ES2549979T3 (es) | 2010-05-26 | 2015-11-03 | Adverio Pharma Gmbh | El uso de estimuladores de la sGC, activadores de la sGC, solos y en combinaciones con inhibidores de la PDE5 para el tratamiento de esclerosis sistémica (EcS) |
| US8569339B2 (en) | 2011-03-10 | 2013-10-29 | Boehringer Ingelheim International Gmbh | Soluble guanylate cyclase activators |
| CN102164320B (zh) | 2011-04-11 | 2016-06-22 | 北京数字太和科技有限责任公司 | 一种改进的基于条件接收技术的终端 |
| ES2911276T3 (es) * | 2013-03-15 | 2022-05-18 | Cyclerion Therapeutics Inc | Estimuladores de sGC |
| WO2015106268A1 (en) * | 2014-01-13 | 2015-07-16 | Ironwood Pharmaceuticals, Inc. | USE OF sGC STIMULATORS FOR THE TREATMENT OF NEUROMUSCULAR DISORDERS |
| US9663527B2 (en) * | 2014-02-11 | 2017-05-30 | Merck Sharp & Dohme Corp. | Factor XIa inhibitors |
| BR112018011154B1 (pt) * | 2015-11-30 | 2023-09-26 | Cyclerion Therapeutics, Inc | Dispersões sólidas compreendendo um estimulador de sgc |
| US11357777B2 (en) | 2016-02-01 | 2022-06-14 | Cyclerion Therapeutics, Inc. | Use of sGC stimulators for the treatment of nonalcoholic steatohepatitis (NASH) |
| US10925876B2 (en) | 2016-05-18 | 2021-02-23 | Merck Sharp & Dohme Corp. | Methods for using triazolo-pyrazinyl soluble guanylate cyclase activators in fibrotic disorders |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011056511A2 (en) * | 2009-10-26 | 2011-05-12 | Auspex Pharmaceuticals, Inc. | 4,6-diaminopyrimidine stimulators of soluble guanylate cyclase |
| WO2016014463A1 (en) * | 2014-07-22 | 2016-01-28 | Boehringer Ingelheim International Gmbh | Heterocyclic carboxylic acids as activators of soluble guanylate cyclase |
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| EP3411026A1 (en) | 2018-12-12 |
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| JP7098214B2 (ja) | 2022-07-11 |
| AU2017216429B2 (en) | 2022-10-06 |
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