FR2460962A1 - Procede pour la purification de l'acide chenodesoxycholique - Google Patents
Procede pour la purification de l'acide chenodesoxycholique Download PDFInfo
- Publication number
- FR2460962A1 FR2460962A1 FR8015140A FR8015140A FR2460962A1 FR 2460962 A1 FR2460962 A1 FR 2460962A1 FR 8015140 A FR8015140 A FR 8015140A FR 8015140 A FR8015140 A FR 8015140A FR 2460962 A1 FR2460962 A1 FR 2460962A1
- Authority
- FR
- France
- Prior art keywords
- acid
- water
- solvent
- filtration
- chenodesoxycholic
- 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.)
- Granted
Links
- 229960001091 chenodeoxycholic acid Drugs 0.000 title claims abstract description 23
- 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 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims description 12
- 238000000746 purification Methods 0.000 title description 5
- 239000002904 solvent Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 239000012535 impurity Substances 0.000 claims abstract description 7
- 238000002425 crystallisation Methods 0.000 claims abstract description 6
- 230000008025 crystallization Effects 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 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 19
- 239000002253 acid Substances 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- -1 POLY-HALOGEN ALIPHATIC HYDROCARBONS Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 description 10
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[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 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000001883 cholelithiasis Diseases 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic 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)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 208000001130 gallstones Diseases 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000003219 lithocholic acid group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT24315/79A IT1165251B (it) | 1979-07-12 | 1979-07-12 | Metodo di furificazione dell'acido chenodesossicolico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2460962A1 true FR2460962A1 (fr) | 1981-01-30 |
| FR2460962B1 FR2460962B1 (enExample) | 1983-08-05 |
Family
ID=11213068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8015140A Granted FR2460962A1 (fr) | 1979-07-12 | 1980-07-08 | Procede pour la purification de l'acide chenodesoxycholique |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4331607A (enExample) |
| JP (1) | JPS5632498A (enExample) |
| FR (1) | FR2460962A1 (enExample) |
| IT (1) | IT1165251B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20061735A1 (it) * | 2006-09-12 | 2008-03-13 | Dipharma Spa | Procedimento per la preparazione di acidi colanici |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2346370A1 (fr) * | 1976-03-29 | 1977-10-28 | Diamalt Ag | Acide chenodesoxycholique cristallin de grande purete, et son procede de preparation |
| EP0012640A1 (fr) * | 1978-12-11 | 1980-06-25 | Roussel-Uclaf | Procédé de purification de l'acide chénodésoxycholique et produits obtenus par ce procédé |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931256A (en) * | 1972-09-21 | 1976-01-06 | Intellectual Property Development Corporation | Chemical process for production of bile acids |
| GB1532413A (en) * | 1974-12-23 | 1978-11-15 | Union International Co Ltd | Chenodeoxycholic acid |
-
1979
- 1979-07-12 IT IT24315/79A patent/IT1165251B/it active
-
1980
- 1980-07-08 FR FR8015140A patent/FR2460962A1/fr active Granted
- 1980-07-10 JP JP9338580A patent/JPS5632498A/ja active Granted
- 1980-07-11 US US06/167,470 patent/US4331607A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2346370A1 (fr) * | 1976-03-29 | 1977-10-28 | Diamalt Ag | Acide chenodesoxycholique cristallin de grande purete, et son procede de preparation |
| EP0012640A1 (fr) * | 1978-12-11 | 1980-06-25 | Roussel-Uclaf | Procédé de purification de l'acide chénodésoxycholique et produits obtenus par ce procédé |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6116279B2 (enExample) | 1986-04-28 |
| FR2460962B1 (enExample) | 1983-08-05 |
| JPS5632498A (en) | 1981-04-01 |
| IT1165251B (it) | 1987-04-22 |
| US4331607A (en) | 1982-05-25 |
| IT7924315A0 (it) | 1979-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH647523A5 (fr) | Solvats d'ethers alicycliques et d'un acide cephem-4-carboxylique, leur preparation et leur utilisation pour l'obtention de l'acide et de ses sels. | |
| JPH08134055A (ja) | ３−ｏ−置換アスコルビン酸の製造方法 | |
| EP0210156B1 (fr) | Complexes moléculaires formés d'un dérivé de benzofuranne et de chlorure d'aluminium, leur préparation et leur utilisation | |
| FR2460962A1 (fr) | Procede pour la purification de l'acide chenodesoxycholique | |
| JP4817496B2 (ja) | 精製テレフタル酸及びイソフタル酸を混合キシレンから製造する方法 | |
| KR100371241B1 (ko) | O,s-디메틸n-아세틸포스포르아미도티오에이트의정제방법 | |
| Major et al. | Preparation and Properties of Pentaacetyl-2-keto-d-glucoheptonic Acid | |
| EP0012640A1 (fr) | Procédé de purification de l'acide chénodésoxycholique et produits obtenus par ce procédé | |
| US4526727A (en) | Process for preparation of an S-alpha-cyano S-alpha-isopropylphenylacetate | |
| FR2938541A1 (fr) | Pentasaccharide cristallise,son procede d'obtention et son utilisation pour la preparation d'idraparinux | |
| AU776674B2 (en) | Method for preparing and isolating 9-deoxo-9(Z)-hydroxyiminoerythromycin | |
| US4698432A (en) | Process for the resolution of (±) 2-[2'-(p-fluorophenyl)-5'-benzoxazolyl]-propionic acid | |
| EP2155189A2 (fr) | Dissolution directe du docetaxel dans un solvant dans le poly sorbate 80 | |
| JP4853691B2 (ja) | α，ω−ジヒドロキシ−δ，（ω−３）−アルカンジオン、ω−ヒドロキシ−（ω−３）−ケト脂肪酸およびその塩、ジカルボン酸およびその塩の分離回収方法 | |
| CH647525A5 (fr) | Solvats cristallins du 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate de 4'-nitrobenzyle et de son sulfoxyde, et leur preparation. | |
| JP4694018B2 (ja) | メバロラクトンメタクリル酸エステルの精製方法 | |
| CH508590A (fr) | Procédé de préparation des esters d'alcoyle inférieurs de l'a-L-aspartyl-L-phénylalanine | |
| BE520416A (enExample) | ||
| AU2009261666A1 (en) | Method for purifying 4-(nitrooxy)butyl(2S)-2-(6-methoxy-2-naphthyl)propanoate | |
| FR2622579A1 (fr) | Acryloylamino-2 methoxy-2 acetate de methyle cristallise pur et son procede d'obtention | |
| FR2653765A1 (fr) | Procede pour la preparation enantioselective de 2-aminotetralines. | |
| BE466504A (enExample) | ||
| BE438280A (enExample) | ||
| BE572697A (enExample) | ||
| CH598285A5 (en) | Steroid 21-(4-acetamidomethylcyclohexane carboxylates) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |