FI56968C - Foerfarande foer framstaellning av hoegren kristallisk kenodesoxicholsyra - Google Patents
Foerfarande foer framstaellning av hoegren kristallisk kenodesoxicholsyra Download PDFInfo
- Publication number
- FI56968C FI56968C FI770934A FI770934A FI56968C FI 56968 C FI56968 C FI 56968C FI 770934 A FI770934 A FI 770934A FI 770934 A FI770934 A FI 770934A FI 56968 C FI56968 C FI 56968C
- Authority
- FI
- Finland
- Prior art keywords
- chenodeoxycholic acid
- acid
- crude
- crystals
- kenodesoxicholsyra
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title description 8
- 238000005057 refrigeration Methods 0.000 title 1
- 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 description 35
- 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 description 35
- 229960001091 chenodeoxycholic acid Drugs 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 3
- 239000004380 Cholic acid Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 229960002471 cholic acid Drugs 0.000 description 3
- 235000019416 cholic acid Nutrition 0.000 description 3
- 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 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000003613 bile acid Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 159000000008 strontium salts Chemical class 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 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 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)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 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
- 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 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 201000001883 cholelithiasis Diseases 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 208000001130 gallstones Diseases 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 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 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2613346 | 1976-03-29 | ||
| DE2613346A DE2613346C3 (de) | 1976-03-29 | 1976-03-29 | Monoklin kristalline Chenodesoxycholsäure und Verfahren zu ihrer Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI770934A7 FI770934A7 (en, 2012) | 1977-09-30 |
| FI56968B FI56968B (fi) | 1980-01-31 |
| FI56968C true FI56968C (fi) | 1980-05-12 |
Family
ID=5973753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI770934A FI56968C (fi) | 1976-03-29 | 1977-03-24 | Foerfarande foer framstaellning av hoegren kristallisk kenodesoxicholsyra |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4163017A (en, 2012) |
| JP (1) | JPS52139053A (en, 2012) |
| CA (1) | CA1098898A (en, 2012) |
| CH (1) | CH631722A5 (en, 2012) |
| DE (1) | DE2613346C3 (en, 2012) |
| FI (1) | FI56968C (en, 2012) |
| FR (1) | FR2346370A1 (en, 2012) |
| GB (1) | GB1539154A (en, 2012) |
| NL (1) | NL7703369A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2446293A1 (fr) * | 1978-12-11 | 1980-08-08 | Roussel Uclaf | Procede de purification de l'acide chenodesoxycholique |
| IT1165253B (it) * | 1979-07-12 | 1987-04-22 | Blasinachim Spa | Procedimento di fabbricazione di acido chenodesossicolico cristallino puro |
| IT1165251B (it) * | 1979-07-12 | 1987-04-22 | Blasinachim Spa | Metodo di furificazione dell'acido chenodesossicolico |
| US5036099A (en) * | 1987-02-02 | 1991-07-30 | Pfizer Inc. | Anhydrous, crystalline sodium salt of 5-chloro-3-(2-thenoyl)-2-oxindole-1-carboxamide |
| CN103044512A (zh) * | 2012-12-19 | 2013-04-17 | 四川大熊生物技术有限公司 | 鹅去氧胆酸粗品的精制方法 |
| CN115181149A (zh) * | 2021-04-01 | 2022-10-14 | 苏州恩泰新材料科技有限公司 | 鹅去氧胆酸新晶型及制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1360354A (en) * | 1972-01-20 | 1974-07-17 | Union International Co Ltd | Chenodeoxycholic acid |
| GB1532413A (en) * | 1974-12-23 | 1978-11-15 | Union International Co Ltd | Chenodeoxycholic acid |
| DE2404102C2 (de) * | 1974-01-25 | 1975-11-06 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Reinigung roher Chenodesoxycholsäure |
-
1976
- 1976-03-29 DE DE2613346A patent/DE2613346C3/de not_active Expired
-
1977
- 1977-03-22 CH CH356077A patent/CH631722A5/de not_active IP Right Cessation
- 1977-03-24 FI FI770934A patent/FI56968C/fi not_active IP Right Cessation
- 1977-03-28 US US05/782,080 patent/US4163017A/en not_active Expired - Lifetime
- 1977-03-28 GB GB12864/77A patent/GB1539154A/en not_active Expired
- 1977-03-28 CA CA274,952A patent/CA1098898A/en not_active Expired
- 1977-03-29 FR FR7709305A patent/FR2346370A1/fr active Granted
- 1977-03-29 JP JP3406077A patent/JPS52139053A/ja active Granted
- 1977-03-29 NL NL7703369A patent/NL7703369A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1098898A (en) | 1981-04-07 |
| GB1539154A (en) | 1979-01-31 |
| DE2613346B2 (de) | 1980-07-17 |
| FI56968B (fi) | 1980-01-31 |
| JPS619319B2 (en, 2012) | 1986-03-22 |
| US4163017A (en) | 1979-07-31 |
| FR2346370B1 (en, 2012) | 1980-08-29 |
| FI770934A7 (en, 2012) | 1977-09-30 |
| DE2613346A1 (de) | 1977-10-06 |
| NL7703369A (nl) | 1977-10-03 |
| CH631722A5 (de) | 1982-08-31 |
| JPS52139053A (en) | 1977-11-19 |
| DE2613346C3 (de) | 1981-07-23 |
| FR2346370A1 (fr) | 1977-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Weisenborn et al. | Synthesis of A-norsteroids | |
| CZ54495A3 (en) | Process for preparing and/or purification of clavulanic acid | |
| US2729654A (en) | 10-hydroxy-3-ketosteroids | |
| KR870001944B1 (ko) | 퀴놀린 카르복실산 유도체의 제조방법 | |
| FI56968B (fi) | Foerfarande foer framstaellning av hoegren kristallisk kenodesoxicholsyra | |
| CA1185233A (en) | Process for preparing high purity ursodeoxycholic acid | |
| DE2821403C2 (de) | Decahydronaphthalin-1-spiro-2'-dihydrobenzofurane, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel | |
| WO2004055025A1 (en) | Pure levofloxacin hemihydrate and processes for preparation thereof | |
| EP0228625B1 (de) | Peptid-Derivate mit inhibitorischer Wirkung auf hydroxylierende Enzyme, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und ihre Verwendung | |
| US3133940A (en) | Process for the separation of delta-1, 4-3-keto steroid compounds from mixtures thereof with other 3-keto steroids | |
| US4337206A (en) | Process for preparing high purity ursodeoxycholic acid | |
| US3836550A (en) | Chenodeoxycholic acid | |
| NO118262B (en, 2012) | ||
| Bolt | O‐hetero‐analogues of steroids | |
| UA120030C2 (uk) | Фармацевтичні склади, які містять 3-(4-цинаміл-1-піперазиніл)амінопохідні 3-формілрифаміцину s та їх застосування | |
| US2880213A (en) | 6alpha-alkyl-4, 16-pregnadiene-3, 20-diones | |
| AU629061B2 (en) | Process for the preparation of heme/hemin | |
| US3169958A (en) | 3-oxygenated-5alpha-halogen-6beta:19-oxido-pregnanes | |
| Zissis et al. | The preparation and properties of some 2-acetamido-2-deoxyhexonic acids | |
| US2924610A (en) | 17alpha-bromo-6alpha-fluoroprogesterone | |
| KR100433566B1 (ko) | (11β,16β)-21-(3-카르복시-3-옥소프로폭시)-11-히드록시-2'-메틸-5'H-프레그나-1,4-디에노[17,16d]옥사졸-3,20-디온의제조방법 | |
| US3004995A (en) | Steroid compounds | |
| EP2402362A2 (en) | Crystalline forms of smilagenin | |
| WO2024236459A1 (en) | Process for the preparation of naldemedine | |
| KR20230043128A (ko) | 소디움 타우로디옥시콜레이트의 대량 생산 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DIAMALT AG |