ES2655034T3 - Proceso para preparar derivados del ácido biliar - Google Patents
Proceso para preparar derivados del ácido biliar Download PDFInfo
- Publication number
- ES2655034T3 ES2655034T3 ES13849263.2T ES13849263T ES2655034T3 ES 2655034 T3 ES2655034 T3 ES 2655034T3 ES 13849263 T ES13849263 T ES 13849263T ES 2655034 T3 ES2655034 T3 ES 2655034T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- preparing
- salt
- pharmaceutically acceptable
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title abstract 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical class C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 68
- 150000003839 salts Chemical class 0.000 abstract description 40
- 238000004519 manufacturing process Methods 0.000 abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 12
- 239000001257 hydrogen Substances 0.000 abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- 239000012453 solvate Substances 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 229910019891 RuCl3 Inorganic materials 0.000 abstract description 5
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 abstract description 5
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- 239000003586 protic polar solvent Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000003880 polar aprotic solvent Substances 0.000 description 16
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical group O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011877 solvent mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical group O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- HGBGABMSTHQFNJ-UHFFFAOYSA-N 1,4-dioxane;sulfur trioxide Chemical compound O=S(=O)=O.C1COCCO1 HGBGABMSTHQFNJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical compound CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- -1 s-pentyl Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261718966P | 2012-10-26 | 2012-10-26 | |
| US201261718966P | 2012-10-26 | ||
| PCT/US2013/066917 WO2014066819A1 (en) | 2012-10-26 | 2013-10-25 | Process for preparing bile acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2655034T3 true ES2655034T3 (es) | 2018-02-16 |
Family
ID=50545344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13849263.2T Active ES2655034T3 (es) | 2012-10-26 | 2013-10-25 | Proceso para preparar derivados del ácido biliar |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US9777038B2 (https=) |
| EP (1) | EP2912013B1 (https=) |
| JP (1) | JP6272888B2 (https=) |
| KR (1) | KR102068381B1 (https=) |
| CN (2) | CN105102425B (https=) |
| AU (1) | AU2013334122B2 (https=) |
| BR (1) | BR112015009395A2 (https=) |
| CA (1) | CA2889592A1 (https=) |
| CY (1) | CY1119731T1 (https=) |
| DK (1) | DK2912013T3 (https=) |
| ES (1) | ES2655034T3 (https=) |
| HK (1) | HK1253301A1 (https=) |
| HU (1) | HUE036887T2 (https=) |
| IL (1) | IL238454B (https=) |
| MX (1) | MX361653B (https=) |
| NO (1) | NO2968302T3 (https=) |
| NZ (2) | NZ707389A (https=) |
| PL (1) | PL2912013T3 (https=) |
| PT (1) | PT2912013T (https=) |
| SG (1) | SG11201503247UA (https=) |
| SM (1) | SMT201700602T1 (https=) |
| WO (1) | WO2014066819A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201503247UA (en) | 2012-10-26 | 2015-06-29 | Intercept Pharmaceuticals Inc | Process for preparing bile acid derivatives |
| SMT202000070T1 (it) * | 2014-05-29 | 2020-03-13 | Bar Pharmaceuticals S R L | Derivati del colano per l'uso del trattamento e/o la prevenzione di malattie mediate da fxr e tgr5/gpbar1 |
| EA033445B1 (ru) | 2014-11-19 | 2019-10-31 | Nzp Uk Ltd | 5-бета-6-алкил-7-гидрокси-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| KR102546748B1 (ko) | 2014-11-19 | 2023-06-22 | 엔제트피 유케이 리미티드 | 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-3,7-다이온 스테로이드 |
| KR102527821B1 (ko) | 2014-11-19 | 2023-05-02 | 엔제트피 유케이 리미티드 | 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-6,7-다이온 스테로이드 |
| CN107207559B (zh) | 2014-11-19 | 2019-10-25 | Nzp英国有限公司 | 作为制备类固醇fxr调节剂的中间体的6-烷基-7-羟基-4-烯-3-酮类固醇 |
| CN104672290B (zh) * | 2015-01-05 | 2017-06-06 | 北京普禄德医药科技有限公司 | 一种用于预防或治疗fxr‑介导的疾病的药物及其制备方法和用途 |
| TW201628625A (zh) | 2015-02-06 | 2016-08-16 | 英特賽普醫藥品公司 | 組合療法醫藥組成物 |
| AU2016325619A1 (en) | 2015-09-24 | 2018-04-12 | Intercept Pharmaceuticals, Inc. | Methods and intermediates for the preparation bile acid derivatives |
| AU2016350690C1 (en) * | 2015-11-06 | 2020-04-23 | Intercept Pharmaceuticals, Inc. | Methods for the preparation of obeticholic acid and derivatives thereof |
| US20200262865A1 (en) * | 2016-02-15 | 2020-08-20 | Alexander Khoruts | Compositions and methods for treating clostridium associated diseases |
| WO2017180577A1 (en) | 2016-04-13 | 2017-10-19 | Intercept Pharmaceuticals, Inc. | Methods of treating cancer |
| TW201738254A (zh) * | 2016-04-19 | 2017-11-01 | 英特賽普醫藥品公司 | 奧貝膽酸及其衍生物之製備方法 |
| GB201608776D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| GB201608777D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
| KR20190057108A (ko) * | 2016-09-30 | 2019-05-27 | 인터셉트 파마슈티컬즈, 인크. | 담즙산 유도체의 결정형 |
| CA3070837A1 (en) * | 2017-07-24 | 2019-01-31 | Intercept Pharmaceuticals, Inc. | Isotopically labeled bile acid derivatives |
| WO2019020067A1 (zh) * | 2017-07-26 | 2019-01-31 | 正大天晴药业集团股份有限公司 | 甾体类衍生物fxr激动剂的制备方法 |
| GB201812382D0 (en) | 2018-07-30 | 2018-09-12 | Nzp Uk Ltd | Compounds |
| CN114144185A (zh) | 2019-05-30 | 2022-03-04 | 英特塞普特医药品公司 | 用于治疗胆汁淤积性肝病的包含fxr激动剂和贝特类的药物组合物 |
| JP2022552655A (ja) | 2019-10-07 | 2022-12-19 | キャリーオペ，インク． | Ｇｐｒ１１９アゴニスト |
| IL295825A (en) | 2020-02-28 | 2022-10-01 | Kallyope Inc | gpr40 agonists |
| WO2021236617A1 (en) | 2020-05-19 | 2021-11-25 | Kallyope, Inc. | Ampk activators |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
| CN116249536A (zh) | 2020-09-18 | 2023-06-09 | 首尔大学校产学协力团 | 牛磺脱氧胆酸钠的批量生产方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5216015A (en) * | 1991-02-05 | 1993-06-01 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having hypocholesterolemic properties |
| ES2248581T3 (es) | 2001-03-12 | 2006-03-16 | Intercept Pharmaceuticals, Inc. | Esteroides como agonistas de fxr. |
| EP1568706A1 (en) | 2004-02-26 | 2005-08-31 | Intercept Pharmaceuticals, Inc. | Novel steroid agonist for FXR |
| US7932244B2 (en) * | 2006-06-27 | 2011-04-26 | Intercept Pharmaceuticals, Inc. | Bile acid derivatives as FXR ligands for the prevention or treatment of FXR-mediated diseases or conditions |
| US9943614B2 (en) | 2008-06-17 | 2018-04-17 | Brigham Young University | Cationic steroid antimicrobial diagnostic, detection, screening and imaging methods |
| WO2010014836A2 (en) * | 2008-07-30 | 2010-02-04 | Intercept Pharmaceuticals, Inc. | Tgr5 modulators and methods of use thereof |
| ES2774368T3 (es) * | 2008-11-19 | 2020-07-20 | Intercept Pharmaceuticals Inc | Moduladores de TGR5 y métodos de uso de los mismos |
| SG11201503247UA (en) | 2012-10-26 | 2015-06-29 | Intercept Pharmaceuticals Inc | Process for preparing bile acid derivatives |
-
2013
- 2013-10-25 SG SG11201503247UA patent/SG11201503247UA/en unknown
- 2013-10-25 WO PCT/US2013/066917 patent/WO2014066819A1/en not_active Ceased
- 2013-10-25 US US14/438,323 patent/US9777038B2/en active Active
- 2013-10-25 CN CN201380068062.XA patent/CN105102425B/zh not_active Expired - Fee Related
- 2013-10-25 NZ NZ707389A patent/NZ707389A/en not_active IP Right Cessation
- 2013-10-25 BR BR112015009395A patent/BR112015009395A2/pt not_active Application Discontinuation
- 2013-10-25 AU AU2013334122A patent/AU2013334122B2/en not_active Ceased
- 2013-10-25 SM SM20170602T patent/SMT201700602T1/it unknown
- 2013-10-25 CA CA2889592A patent/CA2889592A1/en not_active Abandoned
- 2013-10-25 PL PL13849263T patent/PL2912013T3/pl unknown
- 2013-10-25 NZ NZ745013A patent/NZ745013A/en not_active IP Right Cessation
- 2013-10-25 CN CN201810282054.XA patent/CN108250264A/zh active Pending
- 2013-10-25 KR KR1020157012805A patent/KR102068381B1/ko not_active Expired - Fee Related
- 2013-10-25 EP EP13849263.2A patent/EP2912013B1/en not_active Not-in-force
- 2013-10-25 HU HUE13849263A patent/HUE036887T2/hu unknown
- 2013-10-25 DK DK13849263.2T patent/DK2912013T3/en active
- 2013-10-25 ES ES13849263.2T patent/ES2655034T3/es active Active
- 2013-10-25 MX MX2015005286A patent/MX361653B/es active IP Right Grant
- 2013-10-25 JP JP2015539862A patent/JP6272888B2/ja not_active Expired - Fee Related
- 2013-10-25 PT PT138492632T patent/PT2912013T/pt unknown
-
2014
- 2014-03-14 NO NO14725812A patent/NO2968302T3/no unknown
-
2015
- 2015-04-26 IL IL238454A patent/IL238454B/en active IP Right Grant
-
2016
- 2016-02-24 HK HK18112593.6A patent/HK1253301A1/zh unknown
-
2017
- 2017-08-21 US US15/681,609 patent/US10202414B2/en not_active Expired - Fee Related
-
2018
- 2018-01-03 CY CY20181100003T patent/CY1119731T1/el unknown
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