DE2613346C3 - Monoklin kristalline Chenodesoxycholsäure und Verfahren zu ihrer Herstellung - Google Patents
Monoklin kristalline Chenodesoxycholsäure und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2613346C3 DE2613346C3 DE2613346A DE2613346A DE2613346C3 DE 2613346 C3 DE2613346 C3 DE 2613346C3 DE 2613346 A DE2613346 A DE 2613346A DE 2613346 A DE2613346 A DE 2613346A DE 2613346 C3 DE2613346 C3 DE 2613346C3
- Authority
- DE
- Germany
- Prior art keywords
- chenodeoxycholic acid
- acid
- preparation
- chenodeoxycholic
- acetonitrile
- 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
Links
- 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 title claims description 30
- 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 description 30
- 229960001091 chenodeoxycholic acid Drugs 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000002329 infrared spectrum Methods 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000013078 crystal 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 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
- 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
- 239000005909 Kieselgur Substances 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
- 239000013543 active substance Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 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
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000001816 cooling Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 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
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 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
- 230000007056 liver toxicity Effects 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010583 slow cooling 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
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2613346A DE2613346C3 (de) | 1976-03-29 | 1976-03-29 | Monoklin kristalline Chenodesoxycholsäure und Verfahren zu ihrer Herstellung |
| CH356077A CH631722A5 (de) | 1976-03-29 | 1977-03-22 | Verfahren zur herstellung hochreiner, kristalliner chenodesoxycholsaeure. |
| FI770934A FI56968C (fi) | 1976-03-29 | 1977-03-24 | Foerfarande foer framstaellning av hoegren kristallisk kenodesoxicholsyra |
| CA274,952A CA1098898A (en) | 1976-03-29 | 1977-03-28 | Highly pure crystalline chenodesoxycholic acid and process for its preparation |
| GB12864/77A GB1539154A (en) | 1976-03-29 | 1977-03-28 | Very pure crystalline chenodeoxycholic acid and process for its preparation |
| US05/782,080 US4163017A (en) | 1976-03-29 | 1977-03-28 | High purity chenodeoxycholic acid and method for obtaining same |
| FR7709305A FR2346370A1 (fr) | 1976-03-29 | 1977-03-29 | Acide chenodesoxycholique cristallin de grande purete, et son procede de preparation |
| NL7703369A NL7703369A (nl) | 1976-03-29 | 1977-03-29 | Werkwijze voor de bereiding van zeer zuiver kristallijn chenodesoxycholzuur. |
| JP3406077A JPS52139053A (en) | 1976-03-29 | 1977-03-29 | High purity crystalline kenodeoxycholic acid and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2613346A DE2613346C3 (de) | 1976-03-29 | 1976-03-29 | Monoklin kristalline Chenodesoxycholsäure und Verfahren zu ihrer Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2613346A1 DE2613346A1 (de) | 1977-10-06 |
| DE2613346B2 DE2613346B2 (de) | 1980-07-17 |
| DE2613346C3 true DE2613346C3 (de) | 1981-07-23 |
Family
ID=5973753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2613346A Expired DE2613346C3 (de) | 1976-03-29 | 1976-03-29 | Monoklin kristalline Chenodesoxycholsäure und Verfahren zu ihrer Herstellung |
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 |
| FI56968C (fi) | 1980-05-12 |
| 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 |
| FR2346370A1 (fr) | 1977-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |