ES2086388T3 - Procedimiento para la produccion de acido quenodesoxicolico. - Google Patents
Procedimiento para la produccion de acido quenodesoxicolico.Info
- Publication number
- ES2086388T3 ES2086388T3 ES90402879T ES90402879T ES2086388T3 ES 2086388 T3 ES2086388 T3 ES 2086388T3 ES 90402879 T ES90402879 T ES 90402879T ES 90402879 T ES90402879 T ES 90402879T ES 2086388 T3 ES2086388 T3 ES 2086388T3
- Authority
- ES
- Spain
- Prior art keywords
- acid
- alpha
- preparation
- alkali metal
- oxocholanates
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 238000002360 preparation method Methods 0.000 abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 229910001513 alkali metal bromide Inorganic materials 0.000 abstract 2
- -1 alkali metal hypochlorite Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000002812 cholic acid derivative Substances 0.000 abstract 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- RVGVSOKFBAOUCH-JDCDKZKASA-N (4r)-4-[(8r,9s,10s,13r,14s,17r)-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)=O)C)[C@@]1(C)C(=O)C2 RVGVSOKFBAOUCH-JDCDKZKASA-N 0.000 abstract 1
- ZKGCEXPUCJDWMB-ZPMVHPDISA-N (4r)-4-[(8r,9s,10s,13r,14s,17r)-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical class C1CCCC2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)CC[C@@H]3[C@]21C ZKGCEXPUCJDWMB-ZPMVHPDISA-N 0.000 abstract 1
- IOOKJGQHLHXYEF-FFFIEFPASA-N 3,7-Diketocholanic acid Chemical compound C1CC(=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 IOOKJGQHLHXYEF-FFFIEFPASA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 abstract 1
- 229960001091 chenodeoxycholic acid Drugs 0.000 abstract 1
- 150000001801 chenodeoxycholic acids Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 abstract 1
- 150000003674 ursodeoxycholic acids Chemical class 0.000 abstract 1
- 229960001661 ursodiol Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE DESCRIBE UNOS PERFECCIONAMIENTOS DE LAS ETAPAS DEL PROCESO CONVENCIONAL DE PREPARACION DE LOS ACIDOS QUENODESOXICOLICO Y URSODESOXICOLICO QUE COMPRENDEN: LA PREPARACION DE 3(ALFA), 7(ALFA)-DIACETOXI-12(ALFA)-HIDROXI-5(BETA)-COLANATOS DE METILO POR ACETILACION DE LOS COLATOS DE ALQUILO CORRESPONDIENTES, CON LA CANTIDAD ESTEQUIOMETRICA DE ANHIDRIDO ACETICO EN UN DISOLVENTE ORGANCIO EN PRESENCIA DE UNA CANTIDAD CATALITICA DE UNA N,N-DIALQUILANILINA O DE UNA 4-DIALQUILAMINOPIRIDINA Y DE UNA CANTIDAD DE AMINA TERCIARIA INFERIOR DE UN MOL POR MOL DE PRODUCTO DE PARTIDA; LA PREPARACION DE 12-OXOCOLANATOS A PARTIR DE COLATOS DE ALQUILO 3,7-DIACETATO POR OXIDACION CON UN HIPOCLORITO ALCALINO Y ACIDO ACETICO EN CANTIDADES ESTEQUIOMETRICAS EN PRESENCIA DE UN BROMURO ALCALINO Y A UNA TEMPERATURA INFERIOR A 40 C; LA REDUCCION DEL ACIDO 3(ALFA), 7(ALFA)-DIHIDROXI-12-OXO-5(BETA)-COLANICO CON LA HIDRAZINA Y UNA BASE MINERAL OPERANDO EN UN DISOLVENTE ACUOSO-ORGANICO Y ELIMINANDO DESPUES EL AGUA POR DESTILACION; Y LA PREPARACION DE 7-OXOCOLANATOS, PRODUCTOS INTERMEDIOS EN LA PREPARACION DEL ACIDO URSODESOXICOLICO, POR OXIDACION DEL ACIDO QUENODESOXICOLICO CON UN HIPOCLORITO ALCALINO Y ACIDO ACETICO EN CANTIDADES ESTEQUIOMETRICAS EN PRESENCIA DE UN BROMURO ALCALINO Y A UNA TEMPERATURA INFERIOR A 40 C, SEGUIDA POR UNA REDUCCION EVENTUAL DEL ACIDO 3,7-DIOXOCOLANICO.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8913569A FR2653126B1 (fr) | 1989-10-17 | 1989-10-17 | Procede pour la preparation de diacetoxycholanates. |
| FR8913572A FR2653129B1 (fr) | 1989-10-17 | 1989-10-17 | Procede pour la preparation de 7-oxocholanates. |
| FR8913570A FR2653127B1 (fr) | 1989-10-17 | 1989-10-17 | Procede pour la preparation de 12-oxocholanates. |
| FR8913571A FR2653128B1 (fr) | 1989-10-17 | 1989-10-17 | Procede pour la preparation de l'acide chenodesoxycholique. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2086388T3 true ES2086388T3 (es) | 1996-07-01 |
Family
ID=27446720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES90402879T Expired - Lifetime ES2086388T3 (es) | 1989-10-17 | 1990-10-16 | Procedimiento para la produccion de acido quenodesoxicolico. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0424232B1 (es) |
| AT (1) | ATE134378T1 (es) |
| DE (1) | DE69025449T2 (es) |
| DK (1) | DK0424232T3 (es) |
| ES (1) | ES2086388T3 (es) |
| GR (1) | GR3019857T3 (es) |
| IE (1) | IE73449B1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2105500A1 (de) | 2008-03-26 | 2009-09-30 | Pharmazell GmbH | Neue 12alpha-Hydroxysteroiddehydrogenasen, deren Herstellung und deren Verwendung |
| CN101215311B (zh) * | 2008-01-10 | 2010-10-27 | 辽宁百隆生物工程有限公司 | 用含量86%的鹅去氧胆酸生产熊去氧胆酸的生产方法 |
| EP2333101A1 (de) | 2009-12-11 | 2011-06-15 | PharmaZell GmbH | NAD(P)+-Cofaktorregenerierungssystem und dessen Anwendungen |
| CN102060902A (zh) * | 2011-01-21 | 2011-05-18 | 郑州大学 | 一种鹅去氧胆酸的合成方法 |
| ITMI20110534A1 (it) | 2011-03-31 | 2012-10-01 | Prodotti Chimici Alimentari | "nuovo processo per l'ossidazione selettiva di acidi biliari, loro sali o derivati" |
| WO2017207648A1 (en) | 2016-05-31 | 2017-12-07 | Bionice, S.L.U | Process and intermediates for the preparation of obeticholic acid and derivatives thereof |
| EP3431486A1 (en) | 2017-07-18 | 2019-01-23 | Bionice, S.L.U. | Process and intermediates for the synthesis of obeticholic acid and derivatives thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4360470A (en) * | 1980-10-22 | 1982-11-23 | Hoffmann-La Roche Inc. | Process and intermediates for the synthesis of Vitamin D3 metabolites and chenodeoxycholic acid |
| IT1137459B (it) * | 1981-04-14 | 1986-09-10 | Erregierre Spa | Prodesso per la preparazione di acido ursodeossicolico ad alta purezza |
| IT1167478B (it) * | 1981-07-24 | 1987-05-13 | Carlo Scolastico | Derivati dell'acido ursodesossicolico |
| FR2511007A1 (fr) * | 1981-08-07 | 1983-02-11 | Roussel Uclaf | Procede de preparation de l'acide ursodesoxycholique a partir de l'acide 3a, 7b, 12a-trihydroxycholanique et produit intermediaire utilises |
| JPS5842878B2 (ja) * | 1981-12-02 | 1983-09-22 | 名糖産業株式会社 | 12−オキソコラン酸トシルヒドラゾン化合物、その製法ならびに利用 |
| JPS58155098A (ja) * | 1982-03-09 | 1983-09-14 | Yakult Honsha Co Ltd | 微生物によるウルソデオキシコ−ル酸の製造法 |
| IT1204429B (it) * | 1986-01-09 | 1989-03-01 | Blaschim Spa | Riduzione stereoselettiva in acidi biliari |
-
1990
- 1990-10-16 ES ES90402879T patent/ES2086388T3/es not_active Expired - Lifetime
- 1990-10-16 DK DK90402879.2T patent/DK0424232T3/da active
- 1990-10-16 AT AT90402879T patent/ATE134378T1/de not_active IP Right Cessation
- 1990-10-16 IE IE370190A patent/IE73449B1/en not_active IP Right Cessation
- 1990-10-16 EP EP90402879A patent/EP0424232B1/fr not_active Expired - Lifetime
- 1990-10-16 DE DE69025449T patent/DE69025449T2/de not_active Expired - Lifetime
-
1996
- 1996-05-07 GR GR960401242T patent/GR3019857T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0424232A3 (en) | 1992-05-20 |
| EP0424232B1 (fr) | 1996-02-21 |
| IE73449B1 (en) | 1997-06-04 |
| GR3019857T3 (en) | 1996-08-31 |
| ATE134378T1 (de) | 1996-03-15 |
| EP0424232A2 (fr) | 1991-04-24 |
| DE69025449D1 (de) | 1996-03-28 |
| DK0424232T3 (da) | 1996-06-17 |
| IE903701A1 (en) | 1991-04-24 |
| DE69025449T2 (de) | 1996-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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