GB887011A - Glycyrrhetinic acid derivatives - Google Patents
Glycyrrhetinic acid derivativesInfo
- Publication number
- GB887011A GB887011A GB25564/59A GB2556459A GB887011A GB 887011 A GB887011 A GB 887011A GB 25564/59 A GB25564/59 A GB 25564/59A GB 2556459 A GB2556459 A GB 2556459A GB 887011 A GB887011 A GB 887011A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- chloride
- ethinylcarbonyl
- acyloxyacetyl
- derivative
- 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
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical class C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 238000010306 acid treatment Methods 0.000 abstract 1
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/28—Unsaturated compounds polycyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises glycyrrhetinic acid derivatives of the general formula <FORM:0887011/IV (b)/1> in which A and B and/or C and D can together represent a further bond and X is hydroxy, ethinyl or acyloxymethyl and in which rings Y and Z are cis- or trans-relationship, together with their preparation by brominating the corresponding 3,11-diketo-18a - or 18b -olean-12-ene 20-carboxylic acid to give the corresponding 2-bromo or 2,12,13-tribromo compound, dehydrobrominating to the corresponding 1,12-diene or 1,12,18-triene, and then, if desired, forming the acid chloride and converting it into the corresponding ethinylcarbonyl or acyloxyacetyl derivative. The latter steps are carried out by treatment with thionyl chloride or oxalyl chloride to form the acid chloride, followed by reaction with sodium acetylide to form the ethinylcarbonyl derivatives, or with diazomethane followed by acid treatment of the resulting diazoketone to give the acyloxyacetyl derivative. Detailed examples are given. Specifications 798,655, 843,132, 843,133 and 843,137 are referred to.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25564/59A GB887011A (en) | 1959-07-24 | 1959-07-24 | Glycyrrhetinic acid derivatives |
| ES0259841A ES259841A1 (en) | 1959-07-24 | 1960-07-23 | Glycyrrhetinic acid derivatives |
| ES0259842A ES259842A1 (en) | 1959-07-24 | 1960-07-23 | Glycyrrhetinic acid derivatives |
| SE01476/67A SE329845B (en) | 1959-07-24 | 1960-07-25 | |
| FR841942A FR727M (en) | 1959-07-24 | 1960-10-22 | |
| SE1514/62A SE305209B (en) | 1959-07-24 | 1962-02-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25564/59A GB887011A (en) | 1959-07-24 | 1959-07-24 | Glycyrrhetinic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB887011A true GB887011A (en) | 1962-01-10 |
Family
ID=10229734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25564/59A Expired GB887011A (en) | 1959-07-24 | 1959-07-24 | Glycyrrhetinic acid derivatives |
Country Status (4)
| Country | Link |
|---|---|
| ES (2) | ES259842A1 (en) |
| FR (1) | FR727M (en) |
| GB (1) | GB887011A (en) |
| SE (2) | SE329845B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008000070A1 (en) * | 2006-06-27 | 2008-01-03 | Wellington Laboratories Inc. | Glycyrrhetinic acid derivatives |
-
1959
- 1959-07-24 GB GB25564/59A patent/GB887011A/en not_active Expired
-
1960
- 1960-07-23 ES ES0259842A patent/ES259842A1/en not_active Expired
- 1960-07-23 ES ES0259841A patent/ES259841A1/en not_active Expired
- 1960-07-25 SE SE01476/67A patent/SE329845B/xx unknown
- 1960-10-22 FR FR841942A patent/FR727M/fr active Active
-
1962
- 1962-02-12 SE SE1514/62A patent/SE305209B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008000070A1 (en) * | 2006-06-27 | 2008-01-03 | Wellington Laboratories Inc. | Glycyrrhetinic acid derivatives |
| US8389573B2 (en) | 2006-06-27 | 2013-03-05 | Wellington Laboratories Inc. | Glycyrrhetinic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| SE329845B (en) | 1970-10-26 |
| ES259841A1 (en) | 1960-11-01 |
| ES259842A1 (en) | 1961-02-01 |
| FR727M (en) | 1961-08-07 |
| SE305209B (en) | 1968-10-21 |
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