GB1024802A - New derivatives of glycyrrhetinic acid - Google Patents
New derivatives of glycyrrhetinic acidInfo
- Publication number
- GB1024802A GB1024802A GB21601/63A GB2160163A GB1024802A GB 1024802 A GB1024802 A GB 1024802A GB 21601/63 A GB21601/63 A GB 21601/63A GB 2160163 A GB2160163 A GB 2160163A GB 1024802 A GB1024802 A GB 1024802A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- alkyl ester
- hydrogen atoms
- further bond
- dehydrobrominating
- 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
- 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 title abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (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 formula <FORM:1024802/C2/1> wherein E and F and G and H each represent a further bond, or E and F represent a further bond while G and H are hydrogen atoms, or E is a bromine atom and F, G and H are hydrogen atoms and W is an alkoxy group, the two rings Y and Z being in cis- or trans-relationship to one another. The compounds are prepared (a) in the case where G and H are hydrogen atoms, by brominating a 3,11-diketo-18a - or 18b -olean-12-ene-30-oic acid or its alkyl ester to give the 2-bromo-compound, optionally dehydrobrominating to give the 1,1Z-diene and, if the starting material is the free acid, esterifying to give the alkyl ester; or (b) in the case where G and H form a further bond, brominating a 3,11-diketo-18a - or 18b -olean-12-ene-30-oic acid or its alkyl ester to give the 2,12,13-tribromo-compound, dehydrobrominating to give the 1, 12, 18-triene, and if necessary converting to the alkyl ester. The esterification is suitably carried out by reaction with an alkanol or a diazo-alkane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21601/63A GB1024802A (en) | 1963-05-30 | 1963-05-30 | New derivatives of glycyrrhetinic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21601/63A GB1024802A (en) | 1963-05-30 | 1963-05-30 | New derivatives of glycyrrhetinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1024802A true GB1024802A (en) | 1966-04-06 |
Family
ID=10165669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21601/63A Expired GB1024802A (en) | 1963-05-30 | 1963-05-30 | New derivatives of glycyrrhetinic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1024802A (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 |
-
1963
- 1963-05-30 GB GB21601/63A patent/GB1024802A/en not_active Expired
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 |
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