JP2015533852A5 - - Google Patents
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- JP2015533852A5 JP2015533852A5 JP2015539862A JP2015539862A JP2015533852A5 JP 2015533852 A5 JP2015533852 A5 JP 2015533852A5 JP 2015539862 A JP2015539862 A JP 2015539862A JP 2015539862 A JP2015539862 A JP 2015539862A JP 2015533852 A5 JP2015533852 A5 JP 2015533852A5
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- JP
- Japan
- Prior art keywords
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- item
- comprises reacting
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 121
- 238000000034 method Methods 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 241000872931 Myoporum sandwicense Species 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- -1 C23 carboxylic acid Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000007248 oxidative elimination reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261718966P | 2012-10-26 | 2012-10-26 | |
| US61/718,966 | 2012-10-26 | ||
| PCT/US2013/066917 WO2014066819A1 (en) | 2012-10-26 | 2013-10-25 | Process for preparing bile acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015533852A JP2015533852A (ja) | 2015-11-26 |
| JP2015533852A5 true JP2015533852A5 (enExample) | 2016-12-08 |
| JP6272888B2 JP6272888B2 (ja) | 2018-01-31 |
Family
ID=50545344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015539862A Expired - Fee Related JP6272888B2 (ja) | 2012-10-26 | 2013-10-25 | 胆汁酸誘導体を調製するためのプロセス |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US9777038B2 (enExample) |
| EP (1) | EP2912013B1 (enExample) |
| JP (1) | JP6272888B2 (enExample) |
| KR (1) | KR102068381B1 (enExample) |
| CN (2) | CN105102425B (enExample) |
| AU (1) | AU2013334122B2 (enExample) |
| BR (1) | BR112015009395A2 (enExample) |
| CA (1) | CA2889592A1 (enExample) |
| CY (1) | CY1119731T1 (enExample) |
| DK (1) | DK2912013T3 (enExample) |
| ES (1) | ES2655034T3 (enExample) |
| HK (1) | HK1253301A1 (enExample) |
| HU (1) | HUE036887T2 (enExample) |
| IL (1) | IL238454B (enExample) |
| MX (1) | MX361653B (enExample) |
| NO (1) | NO2968302T3 (enExample) |
| NZ (2) | NZ745013A (enExample) |
| PL (1) | PL2912013T3 (enExample) |
| PT (1) | PT2912013T (enExample) |
| SG (1) | SG11201503247UA (enExample) |
| SM (1) | SMT201700602T1 (enExample) |
| WO (1) | WO2014066819A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2912013B1 (en) | 2012-10-26 | 2017-10-11 | Intercept Pharmaceuticals, Inc. | Process for preparing bile acid derivatives |
| FI3626725T3 (fi) * | 2014-05-29 | 2023-03-16 | Bar Pharmaceuticals S R L | Kolaanijohdannaisia käytettäväksi FXR:n ja TGR5:n/GPBAR1:n välittämien sairauksien hoidossa ja/tai ennaltaehkäisyssä |
| CN107108687B (zh) | 2014-11-19 | 2019-10-29 | Nzp英国有限公司 | 作为制备类固醇FXR调节剂的中间体的5β-6-烷基-7-羟基-3-酮类固醇 |
| CA2968310A1 (en) | 2014-11-19 | 2016-05-26 | NZP UK Limited | 6.alpha.-alkyl-6,7-dione steroids as intermediates for the production of steroidal fxr modulators |
| TWI690536B (zh) | 2014-11-19 | 2020-04-11 | 英商Ｎｚｐ英國有限公司 | 化合物（一） |
| KR102546748B1 (ko) | 2014-11-19 | 2023-06-22 | 엔제트피 유케이 리미티드 | 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-3,7-다이온 스테로이드 |
| 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 |
| US11311557B2 (en) | 2015-02-06 | 2022-04-26 | Intercept Pharmaceuticals, Inc. | Pharmaceutical compositions for combination therapy |
| EP3353189A4 (en) | 2015-09-24 | 2019-06-19 | Intercept Pharmaceuticals, Inc. | METHOD AND INTERMEDIATE PRODUCTS FOR THE PREPARATION OF GALLENIC 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 |
| US10369160B2 (en) | 2016-04-13 | 2019-08-06 | 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 |
| GB201608777D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
| GB201608776D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| CA3038534A1 (en) * | 2016-09-30 | 2018-04-05 | Intercept Pharmaceuticals, Inc. | Crystalline forms of a bile acid derivative |
| MX2020000873A (es) | 2017-07-24 | 2020-07-22 | Intercept Pharmaceuticals Inc | Derivados de ácidos biliares marcados isotópicamente. |
| CN110869381B (zh) * | 2017-07-26 | 2021-11-19 | 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 |
| CA3142358A1 (en) | 2019-05-30 | 2020-12-03 | Intercept Pharmaceuticals, Inc. | Pharmaceutical compositions comprising a fxr agonist and a fibrate for use in the treatment of cholestatic liver disease |
| WO2021071837A1 (en) | 2019-10-07 | 2021-04-15 | Kallyope, Inc. | Gpr119 agonists |
| TW202140440A (zh) | 2020-02-28 | 2021-11-01 | 美商克力歐普股份有限公司 | Gpr40激動劑 |
| UY39222A (es) | 2020-05-19 | 2021-11-30 | Kallyope Inc | Activadores de la ampk |
| AU2021297323A1 (en) | 2020-06-26 | 2023-02-16 | Kallyope, Inc. | AMPK activators |
| JP7583398B2 (ja) | 2020-09-18 | 2024-11-14 | ソウル大学校産学協力団 | タウロデオキシコール酸ナトリウムの大量生産方法 |
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 |
| CA2656320C (en) | 2006-06-27 | 2015-04-28 | Intercept Pharmaceuticals, Inc. | Bile acid derivatives as fxr ligands for the prevention or treatment of fxr-mediated diseases or conditions |
| WO2010036427A1 (en) * | 2008-06-17 | 2010-04-01 | Brigham Young University | Cationic steroid antimicrobial diagnostic, detection, screening and imaging methods |
| AU2009276507B2 (en) * | 2008-07-30 | 2015-11-19 | Intercept Pharmaceuticals, Inc. | TGR5 modulators and methods of use thereof |
| CN106380502A (zh) * | 2008-11-19 | 2017-02-08 | 英特塞普特医药品公司 | G蛋白偶联受体5(tgr5)调节剂及其使用方法 |
| EP2912013B1 (en) | 2012-10-26 | 2017-10-11 | Intercept Pharmaceuticals, Inc. | Process for preparing bile acid derivatives |
-
2013
- 2013-10-25 EP EP13849263.2A patent/EP2912013B1/en not_active Not-in-force
- 2013-10-25 NZ NZ745013A patent/NZ745013A/en not_active IP Right Cessation
- 2013-10-25 BR BR112015009395A patent/BR112015009395A2/pt not_active Application Discontinuation
- 2013-10-25 WO PCT/US2013/066917 patent/WO2014066819A1/en not_active Ceased
- 2013-10-25 SG SG11201503247UA patent/SG11201503247UA/en unknown
- 2013-10-25 ES ES13849263.2T patent/ES2655034T3/es active Active
- 2013-10-25 KR KR1020157012805A patent/KR102068381B1/ko not_active Expired - Fee Related
- 2013-10-25 HU HUE13849263A patent/HUE036887T2/hu unknown
- 2013-10-25 CA CA2889592A patent/CA2889592A1/en not_active Abandoned
- 2013-10-25 SM SM20170602T patent/SMT201700602T1/it unknown
- 2013-10-25 CN CN201380068062.XA patent/CN105102425B/zh not_active Expired - Fee Related
- 2013-10-25 PL PL13849263T patent/PL2912013T3/pl unknown
- 2013-10-25 US US14/438,323 patent/US9777038B2/en active Active
- 2013-10-25 NZ NZ707389A patent/NZ707389A/en not_active IP Right Cessation
- 2013-10-25 DK DK13849263.2T patent/DK2912013T3/en active
- 2013-10-25 MX MX2015005286A patent/MX361653B/es active IP Right Grant
- 2013-10-25 AU AU2013334122A patent/AU2013334122B2/en not_active Ceased
- 2013-10-25 JP JP2015539862A patent/JP6272888B2/ja not_active Expired - Fee Related
- 2013-10-25 PT PT138492632T patent/PT2912013T/pt unknown
- 2013-10-25 CN CN201810282054.XA patent/CN108250264A/zh active Pending
-
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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