JP2019515906A5 - - Google Patents
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- Publication number
- JP2019515906A5 JP2019515906A5 JP2018554539A JP2018554539A JP2019515906A5 JP 2019515906 A5 JP2019515906 A5 JP 2019515906A5 JP 2018554539 A JP2018554539 A JP 2018554539A JP 2018554539 A JP2018554539 A JP 2018554539A JP 2019515906 A5 JP2019515906 A5 JP 2019515906A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- ethanol
- vol
- water
- item
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 229940126214 compound 3 Drugs 0.000 claims description 10
- 229940125782 compound 2 Drugs 0.000 claims description 9
- ZXERDUOLZKYMJM-ZWECCWDJSA-N obeticholic acid Chemical compound 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)CCC(O)=O)CC[C@H]21 ZXERDUOLZKYMJM-ZWECCWDJSA-N 0.000 claims description 9
- 229960001601 obeticholic acid Drugs 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 229940125898 compound 5 Drugs 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- -1 sodium triacetoxyborohydride Chemical compound 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 6
- 150000004692 metal hydroxides Chemical class 0.000 claims description 6
- DXOCDBGWDZAYRQ-UHFFFAOYSA-N (3alpha,5beta)-3-Hydroxy-7-oxocholan-24 -oic acid Natural products C1CC(O)CC2CC(=O)C3C4CCC(C(CCC(O)=O)C)C4(C)CCC3C21C DXOCDBGWDZAYRQ-UHFFFAOYSA-N 0.000 claims description 4
- DXOCDBGWDZAYRQ-AURDAFMXSA-N 7-oxolithocholic acid Chemical compound C1C[C@@H](O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)CC[C@@H]3[C@]21C DXOCDBGWDZAYRQ-AURDAFMXSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229940125904 compound 1 Drugs 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 2
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 claims 2
- 229960003868 paraldehyde Drugs 0.000 claims 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662324405P | 2016-04-19 | 2016-04-19 | |
| US62/324,405 | 2016-04-19 | ||
| PCT/US2017/028130 WO2017184598A1 (en) | 2016-04-19 | 2017-04-18 | Methods for the preparation of obeticholic acid and derivatives thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019515906A JP2019515906A (ja) | 2019-06-13 |
| JP2019515906A5 true JP2019515906A5 (https=) | 2020-05-28 |
Family
ID=60116337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018554539A Ceased JP2019515906A (ja) | 2016-04-19 | 2017-04-18 | オベチコール酸およびその誘導体の調製方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10550146B2 (https=) |
| EP (1) | EP3445370B1 (https=) |
| JP (1) | JP2019515906A (https=) |
| KR (1) | KR20180134405A (https=) |
| CN (1) | CN109069517A (https=) |
| AR (1) | AR108237A1 (https=) |
| AU (1) | AU2017254480A1 (https=) |
| BR (1) | BR112018071441A2 (https=) |
| CA (1) | CA3021322A1 (https=) |
| ES (1) | ES2907425T3 (https=) |
| IL (1) | IL262405A (https=) |
| MX (1) | MX374550B (https=) |
| TW (1) | TW201738254A (https=) |
| WO (1) | WO2017184598A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299539B (zh) * | 2018-03-09 | 2021-07-06 | 中山百灵生物技术股份有限公司 | 利用连续流微反应器生产6-亚乙基鹅去氧胆酸的方法 |
| CN110204587B (zh) * | 2019-07-19 | 2020-05-12 | 中山百灵生物技术有限公司 | 一种奥贝胆酸的合成方法 |
| CN113387992A (zh) * | 2020-03-11 | 2021-09-14 | 成都倍特药业股份有限公司 | 奥贝胆酸杂质及其制备方法和检测方法 |
| KR20230044603A (ko) | 2021-09-27 | 2023-04-04 | (주) 테라베스트 | 약물 이합체를 포함하는 나노입자 및 이의 용도 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1895945A (en) * | 1928-12-20 | 1933-01-31 | Goodrich Co B F | Method of making aldehyde-amines |
| 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 |
| ITMI20050912A1 (it) * | 2005-05-19 | 2006-11-20 | Erregierre Spa | Processo di preparazione di acidi 3-a-ya(b)-diidrossi-6-a(b)-alchil-5b-colanici |
| SI3336097T1 (sl) * | 2012-06-19 | 2021-07-30 | Intercept Pharmaceuticals, Inc. | Priprava nekristalinične oblike obetiholne kisline |
| SG11201503247UA (en) | 2012-10-26 | 2015-06-29 | Intercept Pharmaceuticals Inc | Process for preparing bile acid derivatives |
| 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 |
| CN106046095B (zh) * | 2016-06-06 | 2017-02-22 | 南京理工大学 | 奥贝胆酸的合成方法 |
-
2017
- 2017-04-14 TW TW106112531A patent/TW201738254A/zh unknown
- 2017-04-18 KR KR1020187033097A patent/KR20180134405A/ko not_active Withdrawn
- 2017-04-18 ES ES17786465T patent/ES2907425T3/es active Active
- 2017-04-18 CN CN201780029699.6A patent/CN109069517A/zh active Pending
- 2017-04-18 AU AU2017254480A patent/AU2017254480A1/en not_active Abandoned
- 2017-04-18 MX MX2018012777A patent/MX374550B/es active IP Right Grant
- 2017-04-18 CA CA3021322A patent/CA3021322A1/en not_active Abandoned
- 2017-04-18 US US16/094,535 patent/US10550146B2/en active Active
- 2017-04-18 JP JP2018554539A patent/JP2019515906A/ja not_active Ceased
- 2017-04-18 EP EP17786465.9A patent/EP3445370B1/en active Active
- 2017-04-18 BR BR112018071441A patent/BR112018071441A2/pt not_active Application Discontinuation
- 2017-04-18 WO PCT/US2017/028130 patent/WO2017184598A1/en not_active Ceased
- 2017-04-19 AR ARP170100999A patent/AR108237A1/es unknown
-
2018
- 2018-10-16 IL IL262405A patent/IL262405A/en unknown
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