DE2238304C3 - (Choleretisch wirksame) Ester bzw. Salze von Dehydrocholsäure, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate - Google Patents
(Choleretisch wirksame) Ester bzw. Salze von Dehydrocholsäure, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende ArzneipräparateInfo
- Publication number
- DE2238304C3 DE2238304C3 DE2238304A DE2238304A DE2238304C3 DE 2238304 C3 DE2238304 C3 DE 2238304C3 DE 2238304 A DE2238304 A DE 2238304A DE 2238304 A DE2238304 A DE 2238304A DE 2238304 C3 DE2238304 C3 DE 2238304C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dehydrocholic acid
- salts
- esters
- compounds
- 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
- 229960002997 dehydrocholic acid Drugs 0.000 title claims description 23
- OHXPGWPVLFPUSM-KLRNGDHRSA-N 3,7,12-trioxo-5beta-cholanic acid Chemical class C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C OHXPGWPVLFPUSM-KLRNGDHRSA-N 0.000 title claims description 18
- 150000003839 salts Chemical class 0.000 title claims description 17
- 150000002148 esters Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 11
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 4
- 235000013985 cinnamic acid Nutrition 0.000 claims description 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 4
- 229930016911 cinnamic acid Natural products 0.000 claims description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- -1 acyloxy radicals Chemical class 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 210000000941 bile Anatomy 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000001989 choleretic effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940009979 dehydrocholate Drugs 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KSEBMYQBYZTDHS-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940070710 valerate Drugs 0.000 description 2
- MSFXPXIVPZXOKN-UHFFFAOYSA-N 2-acetyloxy-3-phenylprop-2-enoic acid Chemical compound CC(=O)OC(C(O)=O)=CC1=CC=CC=C1 MSFXPXIVPZXOKN-UHFFFAOYSA-N 0.000 description 1
- IHKNVZISLLDMOR-UHFFFAOYSA-N 3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(C=CC(O)=O)=CC=C1OC(C)=O IHKNVZISLLDMOR-UHFFFAOYSA-N 0.000 description 1
- QABZTGNRWBRJBO-UHFFFAOYSA-N 3-(5-bromo-2-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(Br)C=C1C=CC(O)=O QABZTGNRWBRJBO-UHFFFAOYSA-N 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-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
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960005010 orotic acid Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1148471A CH557808A (de) | 1971-08-04 | 1971-08-04 | Verfahren zur herstellung von salzen von gallensaeuredialkylamino-alkylestern mit substituierten zimtsaeuren. |
| CH1408571A CH551998A (de) | 1971-09-28 | 1971-09-28 | Verfahren zur herstellung eines salzes von gallensaeuredialkylaminoalkylestern. |
| CH101272A CH565129A5 (en) | 1972-01-24 | 1972-01-24 | Esters and salts of cholic acid derivs - having choleretic activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2238304A1 DE2238304A1 (de) | 1973-02-15 |
| DE2238304B2 DE2238304B2 (de) | 1980-07-03 |
| DE2238304C3 true DE2238304C3 (de) | 1981-06-19 |
Family
ID=27172602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2238304A Expired DE2238304C3 (de) | 1971-08-04 | 1972-08-03 | (Choleretisch wirksame) Ester bzw. Salze von Dehydrocholsäure, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3846411A (https=) |
| BE (1) | BE786477A (https=) |
| CA (1) | CA969173A (https=) |
| DE (1) | DE2238304C3 (https=) |
| DK (1) | DK135721B (https=) |
| ES (1) | ES405492A1 (https=) |
| FR (1) | FR2148002B1 (https=) |
| GB (1) | GB1388427A (https=) |
| IL (1) | IL39999A0 (https=) |
| NL (1) | NL7210586A (https=) |
| SE (1) | SE378811B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910888A (en) * | 1971-08-04 | 1975-10-07 | Medichemie A G | Choleretically active esters and salts of bile acids |
| US3931256A (en) * | 1972-09-21 | 1976-01-06 | Intellectual Property Development Corporation | Chemical process for production of bile acids |
| US5079240A (en) * | 1990-03-15 | 1992-01-07 | The Regents Of The University Of California | Synthetic conjugated bile acid and method of use thereof |
| JP5283043B2 (ja) * | 2007-06-04 | 2013-09-04 | 学校法人日本大学 | 作用選択的ビタミンｄ受容体作用剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2562350A (en) * | 1945-10-12 | 1951-07-31 | Searle & Co | Basic esters of bile acids |
| US2763645A (en) * | 1955-01-28 | 1956-09-18 | Pfizer & Co C | Amino alcohol esters of etiocholene 17 alpha hydroxy 3 one 17 beta carboxylic acid |
| US3534070A (en) * | 1968-03-12 | 1970-10-13 | Dainippon Pharmaceutical Co | 3,7,12-triketocholanyl-alpha-amino acids |
-
1972
- 1972-07-17 US US00272156A patent/US3846411A/en not_active Expired - Lifetime
- 1972-07-17 SE SE7209401A patent/SE378811B/xx unknown
- 1972-07-18 GB GB3358672A patent/GB1388427A/en not_active Expired
- 1972-07-19 BE BE786477A patent/BE786477A/xx unknown
- 1972-07-20 DK DK359972AA patent/DK135721B/da unknown
- 1972-07-20 FR FR7226261A patent/FR2148002B1/fr not_active Expired
- 1972-07-25 CA CA147,854A patent/CA969173A/en not_active Expired
- 1972-07-26 IL IL39999A patent/IL39999A0/xx unknown
- 1972-08-02 NL NL7210586A patent/NL7210586A/xx not_active Application Discontinuation
- 1972-08-03 DE DE2238304A patent/DE2238304C3/de not_active Expired
- 1972-08-03 ES ES405492A patent/ES405492A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3846411A (en) | 1974-11-05 |
| GB1388427A (en) | 1975-03-26 |
| DK135721B (da) | 1977-06-13 |
| FR2148002B1 (https=) | 1975-10-31 |
| DE2238304B2 (de) | 1980-07-03 |
| SE378811B (https=) | 1975-09-15 |
| ES405492A1 (es) | 1975-07-16 |
| NL7210586A (https=) | 1973-02-06 |
| BE786477A (fr) | 1972-11-16 |
| DK135721C (https=) | 1977-11-14 |
| IL39999A0 (en) | 1972-09-28 |
| FR2148002A1 (https=) | 1973-03-11 |
| DE2238304A1 (de) | 1973-02-15 |
| CA969173A (en) | 1975-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2102172C3 (de) | Neue Mittel zur Behandlung und Pflege der Haut | |
| DE2253750C3 (de) | Apovincaminsaure-alkylester, Verfahren zu ihrer Herstellung und pharmazeutische | |
| DE2238304C3 (de) | (Choleretisch wirksame) Ester bzw. Salze von Dehydrocholsäure, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate | |
| DE2446100C3 (de) | Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2815088A1 (de) | 5-piperazinylsubstituierte derivate von pyrido- eckige klammer auf 2.3-b eckige klammer zu -benzothiazepin(1.5), ihre herstellung und pharmazeutische mittel | |
| DE2427272C3 (de) | 1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum | |
| DE2519059A1 (de) | Neue aminoderivate von 6-phenylpyrazolo(3.4-b)pyridinen | |
| DE2655130C3 (de) | Eine praktisch lösungsmittelfreie Kristallform des Cefacetril-Natriumsalzes | |
| DE2351292C3 (de) | 2,10-Dichlor-6-äthoxycarbonyl-12-methyl-12H-dibenzo[d,g][1,3]dioxocin und Verfahren zu dessen Herstellung sowie diese Verbindung enthaltende Arzneimittel | |
| DE3337925C2 (de) | N-(6-Aminopurinyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazin-3-carboxamid-1,1-dioxid, Verfahren zu dessen Herstellung und seine Verwendung | |
| DE2320945A1 (de) | Neue ester der acetylsalicylsaeure | |
| DE1493618A1 (de) | Cumarinderivate und ein Verfahren zu ihrer Herstellung | |
| AT325789B (de) | Verfahren zur herstellung von neuen salzen von gallensäureestern | |
| DE1595870C3 (de) | Verfahren zur Herstellung von 3-(o-Methoxyphenoxy)-1,2-propandiolnicotinaten und deren Säureadditionssalzen | |
| CH557808A (de) | Verfahren zur herstellung von salzen von gallensaeuredialkylamino-alkylestern mit substituierten zimtsaeuren. | |
| DE1670539C3 (de) | Diacylthiamine und Verfahren zu deren Herstellung | |
| CH653334A5 (de) | Verfahren zur herstellung von vinkaminsaeureestern. | |
| DE724268C (de) | Verfahren zur Herstellung eines reinen ª‡-Tokopherolesters bzw. von reinem ª‡-Tokopherol | |
| AT265243B (de) | Verfahren zur Herstellung von neuen Salzen der p-Chlorphenoxyisobuttersäure | |
| AT239969B (de) | Verfahren zur Herstellung von neuen Estern der Nicotinsäure | |
| AT277249B (de) | Verfahren zur Herstellung von neuen Chinolinderivaten | |
| DE965637C (de) | Verfahren zur Herstellung von 19-Nortestosteron-17-acylaten und bzw. oder deren 3-Enolacylaten | |
| DE825548C (de) | Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen | |
| DE1795680C3 (de) | Verfahren zur Herstellung von N-(1 - Alkyl-2-pyrrolidinylmethyi) -3methoxyindol-2-carboxamiden | |
| CH511847A (de) | Verfahren zur Herstellung von neuen serumlipoidvermindernden Pyridinderivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |