GB1046566A - Glycyrrhetinic acid esters and the method of preparation thereof - Google Patents
Glycyrrhetinic acid esters and the method of preparation thereofInfo
- Publication number
- GB1046566A GB1046566A GB20087/65A GB2008765A GB1046566A GB 1046566 A GB1046566 A GB 1046566A GB 20087/65 A GB20087/65 A GB 20087/65A GB 2008765 A GB2008765 A GB 2008765A GB 1046566 A GB1046566 A GB 1046566A
- Authority
- GB
- United Kingdom
- Prior art keywords
- preparation
- stearoyl
- stearyl
- glycyrrhetinic acid
- oleoyl
- 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 5
- 238000002360 preparation method Methods 0.000 title abstract 3
- -1 oleoyl ester Chemical class 0.000 abstract 3
- 125000004079 stearyl group Chemical group [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])C([H])([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 abstract 3
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 abstract 2
- 229960003720 enoxolone Drugs 0.000 abstract 2
- MPDGHEJMBKOTSU-WFJWTYAKSA-N (2s,4as,6as,6br,10s,12as)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid Chemical class C12C(=O)C=C3C4C[C@@](C)(C(O)=O)CC[C@]4(C)CC[C@@]3(C)[C@]1(C)CCC1[C@]2(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-WFJWTYAKSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 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 abstract 1
- 125000001117 oleyl group Chemical group [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])=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 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000003696 stearoyl 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])([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])C([H])([H])[H] 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises glycyrrhetinic esters of the formula <FORM:1046566/C2/1> wherein R is a stearyl or oleyl group and R1 is hydrogen or a stearoyl or oleoyl group and their preparation by reacting glycyrrhetinic acid or its 3-stearoyl or oleoyl ester with a stearyl or oleyl halide or by esterifying glycyrrhetinic acid or its 3-stearoyl or oleoyl ester with stearyl or oroleyl alcohol in the presence of an acid esterification accelerator. Pharmaceutical preparations having anti-inflammatory activity comprise the above compounds and an inert carrier, suitably in the form of an oil, salve, emulsion or sticklike preparation.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2691364 | 1964-05-14 | ||
| JP4842664 | 1964-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1046566A true GB1046566A (en) | 1966-10-26 |
Family
ID=26364768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20087/65A Expired GB1046566A (en) | 1964-05-14 | 1965-05-12 | Glycyrrhetinic acid esters and the method of preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3405152A (en) |
| GB (1) | GB1046566A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004009038A2 (en) * | 2002-07-18 | 2004-01-29 | Cognis Deutschland Gmbh & Co. Kg | Cosmetic preparations with antibacterial properties comprising glycyrrhetinic acid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB894265A (en) * | 1960-03-04 | 1962-04-18 | Biorex Laboratories Ltd | Glycyrrhetinic acid esters |
-
1965
- 1965-05-10 US US454566A patent/US3405152A/en not_active Expired - Lifetime
- 1965-05-12 GB GB20087/65A patent/GB1046566A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004009038A2 (en) * | 2002-07-18 | 2004-01-29 | Cognis Deutschland Gmbh & Co. Kg | Cosmetic preparations with antibacterial properties comprising glycyrrhetinic acid |
| WO2004009038A3 (en) * | 2002-07-18 | 2004-05-06 | Cognis Deutschland Gmbh | Cosmetic preparations with antibacterial properties comprising glycyrrhetinic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| US3405152A (en) | 1968-10-08 |
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