DE3225528C2 - 7-Acyl-ursodesoxycholsäuren und diese Verbindungen enthaltende Arzneimittel - Google Patents
7-Acyl-ursodesoxycholsäuren und diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE3225528C2 DE3225528C2 DE3225528A DE3225528A DE3225528C2 DE 3225528 C2 DE3225528 C2 DE 3225528C2 DE 3225528 A DE3225528 A DE 3225528A DE 3225528 A DE3225528 A DE 3225528A DE 3225528 C2 DE3225528 C2 DE 3225528C2
- Authority
- DE
- Germany
- Prior art keywords
- ursodeoxycholic acid
- formula
- udc
- acid
- acyl
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 6
- 239000003814 drug Substances 0.000 title description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 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 description 26
- 229960001661 ursodiol Drugs 0.000 abstract description 23
- 201000001883 cholelithiasis Diseases 0.000 abstract description 5
- 208000001130 gallstones Diseases 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 238000002560 therapeutic procedure Methods 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 208000006575 hypertriglyceridemia Diseases 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical class 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 description 22
- 208000015924 Lithiasis Diseases 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000037213 diet Effects 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000002779 inactivation Effects 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229960001091 chenodeoxycholic acid Drugs 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 description 3
- 241000398985 Cricetidae Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229940049918 linoleate Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 230000000927 lithogenic effect Effects 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- UYVVLXVBEQAATF-UHFFFAOYSA-N 4-(1,3,7,12-tetrahydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic acid Chemical compound OC1CC2CC(O)CC(O)C2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 UYVVLXVBEQAATF-UHFFFAOYSA-N 0.000 description 1
- KPRGOTLNGIBVFL-GINZOMEDSA-N 7-ketodehydroepiandrosterone Chemical group C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C(=O)C=C21 KPRGOTLNGIBVFL-GINZOMEDSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002690 anti-lithiasic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 231100000334 hepatotoxic Toxicity 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005303 weighing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23108/81A IT1167478B (it) | 1981-07-24 | 1981-07-24 | Derivati dell'acido ursodesossicolico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3225528A1 DE3225528A1 (de) | 1983-02-10 |
| DE3225528C2 true DE3225528C2 (de) | 1985-03-28 |
Family
ID=11203856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3225528A Expired DE3225528C2 (de) | 1981-07-24 | 1982-07-08 | 7-Acyl-ursodesoxycholsäuren und diese Verbindungen enthaltende Arzneimittel |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4440688A (enExample) |
| JP (1) | JPS5824597A (enExample) |
| DE (1) | DE3225528C2 (enExample) |
| FR (1) | FR2510583B1 (enExample) |
| GB (1) | GB2105722B (enExample) |
| IT (1) | IT1167478B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19645044A1 (de) * | 1996-10-31 | 1998-05-07 | Falk Pharma Gmbh | Verwendung von Ursodeoxycholsäure zur topischen Behandlung von Entzündungserkrankungen der Schleimhäute |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8417895D0 (en) * | 1984-07-13 | 1984-08-15 | Marples B A | Pharmaceutical anti-fungal composition |
| US4892868A (en) * | 1984-08-17 | 1990-01-09 | Gipharmex, S.P.A. | Derivatives of biliary acids, process for the production thereof and corresponding pharmaceutical compositions |
| IT1199843B (it) * | 1986-12-05 | 1989-01-05 | Gipharmex Spa | Complesso di prodotti per il trattamento rapido e non invasivo della calcolosi biliare |
| IE73449B1 (en) * | 1989-10-17 | 1997-06-04 | Sanofi Sa | Process for the production of chenodeoxycholic |
| FR2653126B1 (fr) * | 1989-10-17 | 1994-12-09 | Sanofi Sa | Procede pour la preparation de diacetoxycholanates. |
| NZ245504A (en) * | 1991-12-20 | 1995-08-28 | Hoechst Ag | Bile acid derivatives containing an ethylenically unsaturated grouping |
| IL123998A (en) * | 1998-04-08 | 2004-09-27 | Galmed Int Ltd | Conjugates of bile salts and pharmaceutical preparations containing them |
| IL142650A (en) * | 1998-04-08 | 2007-06-03 | Galmed Int Ltd | Use of bile acid or bile salt fatty acids conjugates for the preparation of pharmaceutical compositions for reducing cholesterol, treating fatty liver and treating hyperglycemia and diabetes |
| US8975246B2 (en) | 2001-04-17 | 2015-03-10 | Galmed Research And Development Ltd. | Bile acid or bile salt fatty acid conjugates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3833620A (en) * | 1972-11-16 | 1974-09-03 | Intellectual Property Dev Corp | Production of chenodeoxycholic acid |
| FR2457302A1 (fr) * | 1979-05-23 | 1980-12-19 | Roussel Uclaf | Nouveau procede de purification de l'acide ursodesoxycholique |
| IT1165252B (it) * | 1979-07-12 | 1987-04-22 | Blasinachim Spa | Procedimento di purificazione dell'acido ursodesossicolico attraverso nuovi derivati |
-
1981
- 1981-07-24 IT IT23108/81A patent/IT1167478B/it active
-
1982
- 1982-06-24 GB GB08218300A patent/GB2105722B/en not_active Expired
- 1982-06-28 US US06/392,634 patent/US4440688A/en not_active Expired - Fee Related
- 1982-07-08 DE DE3225528A patent/DE3225528C2/de not_active Expired
- 1982-07-17 JP JP57124985A patent/JPS5824597A/ja active Granted
- 1982-07-23 FR FR8212949A patent/FR2510583B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19645044A1 (de) * | 1996-10-31 | 1998-05-07 | Falk Pharma Gmbh | Verwendung von Ursodeoxycholsäure zur topischen Behandlung von Entzündungserkrankungen der Schleimhäute |
Also Published As
| Publication number | Publication date |
|---|---|
| US4440688A (en) | 1984-04-03 |
| DE3225528A1 (de) | 1983-02-10 |
| IT8123108A1 (it) | 1983-01-24 |
| IT1167478B (it) | 1987-05-13 |
| GB2105722B (en) | 1985-06-26 |
| JPS5824597A (ja) | 1983-02-14 |
| FR2510583A1 (fr) | 1983-02-04 |
| JPS6246554B2 (enExample) | 1987-10-02 |
| IT8123108A0 (it) | 1981-07-24 |
| FR2510583B1 (fr) | 1985-08-30 |
| GB2105722A (en) | 1983-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |