IE49728B1 - Sterolinhemiesters,process for their preparation and pharmaceutical compositions containing them - Google Patents
Sterolinhemiesters,process for their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IE49728B1 IE49728B1 IE1238/79A IE123879A IE49728B1 IE 49728 B1 IE49728 B1 IE 49728B1 IE 1238/79 A IE1238/79 A IE 1238/79A IE 123879 A IE123879 A IE 123879A IE 49728 B1 IE49728 B1 IE 49728B1
- Authority
- IE
- Ireland
- Prior art keywords
- glucoside
- compounds
- sitosteryl
- hemiester
- steryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 11
- 230000008569 process Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 229930182470 glycoside Natural products 0.000 claims abstract description 21
- 150000002338 glycosides Chemical class 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract 3
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- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 11
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims description 9
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims description 9
- 229950005143 sitosterol Drugs 0.000 claims description 7
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims description 6
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 claims description 6
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 claims description 6
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- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 claims description 6
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 6
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 6
- 235000015500 sitosterol Nutrition 0.000 claims description 6
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- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 claims description 5
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 claims description 5
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 claims description 5
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- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 claims description 5
- HXQRIQXPGMPSRW-UHZRDUGNSA-N Pollinastanol Natural products O[C@@H]1C[C@H]2[C@@]3([C@]4([C@H]([C@@]5(C)[C@@](C)([C@H]([C@H](CCCC(C)C)C)CC5)CC4)CC2)C3)CC1 HXQRIQXPGMPSRW-UHZRDUGNSA-N 0.000 claims description 5
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims description 5
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims description 5
- 235000000431 campesterol Nutrition 0.000 claims description 5
- 235000012000 cholesterol Nutrition 0.000 claims description 5
- ONQRKEUAIJMULO-YBXTVTTCSA-N cycloartenol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]3(C)[C@@H]1CC2 ONQRKEUAIJMULO-YBXTVTTCSA-N 0.000 claims description 5
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- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7828833 | 1978-07-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE791238L IE791238L (en) | 1980-01-05 |
| IE49728B1 true IE49728B1 (en) | 1985-12-11 |
Family
ID=10498259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1238/79A IE49728B1 (en) | 1978-07-05 | 1979-08-08 | Sterolinhemiesters,process for their preparation and pharmaceutical compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4254111A (OSRAM) |
| EP (1) | EP0007474B1 (OSRAM) |
| JP (1) | JPS5942680B2 (OSRAM) |
| AT (1) | ATE11417T1 (OSRAM) |
| AU (1) | AU521669B2 (OSRAM) |
| CA (1) | CA1142510A (OSRAM) |
| DE (1) | DE2967364D1 (OSRAM) |
| DK (1) | DK285679A (OSRAM) |
| ES (1) | ES482241A1 (OSRAM) |
| IE (1) | IE49728B1 (OSRAM) |
| IL (1) | IL57728A (OSRAM) |
| IN (1) | IN152550B (OSRAM) |
| NZ (1) | NZ190914A (OSRAM) |
| PT (1) | PT69874A (OSRAM) |
| SU (1) | SU971103A3 (OSRAM) |
| YU (1) | YU41651B (OSRAM) |
| ZA (1) | ZA793321B (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56113799A (en) * | 1980-02-08 | 1981-09-07 | Nippon Shinyaku Co Ltd | Glucoside derivative |
| JPS5874619A (ja) * | 1981-10-29 | 1983-05-06 | Nippon Shinyaku Co Ltd | リポソ−ム及びその製法 |
| US4602003A (en) * | 1982-05-17 | 1986-07-22 | Medical Research Foundation Of Oregon | Synthetic compounds to inhibit intestinal absorption of cholesterol in the treatment of hypercholesterolemia |
| JPS5948414A (ja) * | 1982-09-10 | 1984-03-19 | Asahi Denka Kogyo Kk | ビタミンｅの水溶性製剤 |
| CA1229636A (en) * | 1983-04-14 | 1987-11-24 | Richard S. Antoszewski | Radial-theta manipulator apparatus |
| DE3401178A1 (de) * | 1984-01-14 | 1985-07-18 | Roecar Holdings (Netherlands Antilles) N.V., Willemstad, Curacao, Niederländische Antillen | Verwendung von phytosterolglykosiden zur behandlung erhoehter 5(6)(alpha)-epoxicholesterolspiegel |
| DE3416112A1 (de) * | 1984-04-30 | 1985-10-31 | Roecar Holdings (Netherlands Antilles) N.V., Willemstad, Curacao, Niederländische Antillen | Verwendung von sterolinen und spiroketalinen als lipoxygenaseregulatoren |
| JPS62180694A (ja) * | 1986-01-27 | 1987-08-07 | ドナルド・ジエイ・イムサンド | ３次元テレビジヨン方式 |
| DE3829641A1 (de) * | 1988-09-01 | 1990-03-15 | Roecar Holdings Nv | Transdermal anwendbare pharmazeutische zubereitungen mit sterolinen und/oder spiroketalinen |
| EP0509656B1 (en) * | 1991-03-28 | 1996-09-18 | Rooperol (Na) Nv | Compositions of phytosterols and phytosterolins as immunmodulators |
| EP0647235B1 (en) * | 1992-06-26 | 1997-09-17 | Pfizer Inc. | Process for steroidal peracyl glycosides |
| AUPN029994A0 (en) * | 1994-12-23 | 1995-01-27 | Ici Australia Operations Proprietary Limited | Alkypolysaccharide derivatives & compositions |
| DE19701264A1 (de) * | 1997-01-16 | 1998-07-23 | Kief Lizenz Verwertungsgesells | Heilmittel, enthaltend Betasitosterin und/oder Phytosterol/Betasitosteringemische |
| WO2001032679A2 (en) * | 1999-11-01 | 2001-05-10 | Forbes Medi-Tech Inc. | Novel glycosides comprising pentose mono-, di-, tri-, or oligosaccharides and phytosterols and/or phytostanols |
| EP1334368B1 (en) | 2000-11-03 | 2015-02-25 | Neurodyn, Inc. | Sterol glucoside toxins |
| EP2030979A1 (en) * | 2003-04-02 | 2009-03-04 | The Government of the United States of America as Represented by The Department of Health and Human Services | Cholesterol-containing compounds and their use as immunogens against borrelia burgdorferi |
| US8338635B2 (en) * | 2007-05-31 | 2012-12-25 | Satomi Niwayama | Synthesis of half esters |
| US20090011060A1 (en) * | 2007-07-06 | 2009-01-08 | Peter Koepke | Campsiandra angustifolia extract and methods of extracting and using such extract |
| US20090017140A1 (en) * | 2007-07-09 | 2009-01-15 | Peter Koepke | Maytenus abenfolia extract and methods of extracting and using such extract |
| KR101038022B1 (ko) | 2007-07-25 | 2011-05-30 | 주식회사 알엔에이 | 신규 당 화합물 |
| US20090035395A1 (en) * | 2007-08-01 | 2009-02-05 | Peter Koepke | Spondias mombin l. extract and methods of extracting and using such extract |
| US7879369B2 (en) * | 2007-09-18 | 2011-02-01 | Selvamedica, Llc | Combretum laurifolium Mart. extract and methods of extracting and using such extract |
| WO2010048710A1 (en) | 2008-10-31 | 2010-05-06 | Neurodyn, Inc. | Neurotoxic sterol glycosides |
| CN103732608A (zh) * | 2011-05-20 | 2014-04-16 | 马来西亚博特拉大学 | 一种包含酰化固醇糖苷的组成物在用于制备一产物中的用途 |
| JP5953490B2 (ja) * | 2012-05-10 | 2016-07-20 | 株式会社タニタ | 浮腫評価装置 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE35018B1 (en) * | 1970-03-18 | 1975-10-15 | Liebenberg R W | Therapeutic agent |
| GB1390683A (en) * | 1972-12-18 | 1975-04-16 | Biorex Laboratories Ltd | Pharmaceutical composition |
| JPS5123254A (en) * | 1974-08-14 | 1976-02-24 | Nippon Shinyaku Co Ltd | Suteriru beetaa dd gurukoshidono parumichinsanesuteruno seizohoho |
| US3963697A (en) * | 1974-08-29 | 1976-06-15 | Curtis Nuclear Corporation | Labelled cardiotonic glycosides for use in radioimmunoassay |
| US4021535A (en) * | 1975-01-14 | 1977-05-03 | Beckman Instruments, Inc. | Reagents used in the radioimmunoassay of digoxin |
| JPS51118817A (en) * | 1975-04-08 | 1976-10-19 | Nippon Shinyaku Co Ltd | A process for preparing absorbable steroid glycoside pharmaceutical |
| FR2312257A1 (fr) * | 1975-05-28 | 1976-12-24 | Nippon Shinyaku Co Ltd | Produits pharmaceutiques a action hemostatique comprenant des steryl-b-d-glucosides et leurs monopalmitates |
-
1979
- 1979-07-02 US US06/053,735 patent/US4254111A/en not_active Expired - Lifetime
- 1979-07-03 ZA ZA793321A patent/ZA793321B/xx unknown
- 1979-07-03 AT AT79102235T patent/ATE11417T1/de not_active IP Right Cessation
- 1979-07-03 DE DE7979102235T patent/DE2967364D1/de not_active Expired
- 1979-07-03 EP EP79102235A patent/EP0007474B1/en not_active Expired
- 1979-07-04 SU SU792788551A patent/SU971103A3/ru active
- 1979-07-04 IL IL57728A patent/IL57728A/xx not_active IP Right Cessation
- 1979-07-04 PT PT69874A patent/PT69874A/pt unknown
- 1979-07-04 CA CA000331143A patent/CA1142510A/en not_active Expired
- 1979-07-04 NZ NZ190914A patent/NZ190914A/xx unknown
- 1979-07-05 YU YU1639/79A patent/YU41651B/xx unknown
- 1979-07-05 AU AU48667/79A patent/AU521669B2/en not_active Ceased
- 1979-07-05 ES ES482241A patent/ES482241A1/es not_active Expired
- 1979-07-05 DK DK285679A patent/DK285679A/da unknown
- 1979-07-05 JP JP54085498A patent/JPS5942680B2/ja not_active Expired
- 1979-07-16 IN IN510/DEL/79A patent/IN152550B/en unknown
- 1979-08-08 IE IE1238/79A patent/IE49728B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL57728A0 (en) | 1979-11-30 |
| AU4866779A (en) | 1980-01-10 |
| EP0007474A1 (en) | 1980-02-06 |
| IN152550B (OSRAM) | 1984-02-11 |
| ATE11417T1 (de) | 1985-02-15 |
| US4254111A (en) | 1981-03-03 |
| DE2967364D1 (en) | 1985-03-07 |
| DK285679A (da) | 1980-01-06 |
| ZA793321B (en) | 1981-03-25 |
| AU521669B2 (en) | 1982-04-22 |
| IL57728A (en) | 1983-06-15 |
| CA1142510A (en) | 1983-03-08 |
| PT69874A (en) | 1979-08-01 |
| JPS5536472A (en) | 1980-03-14 |
| IE791238L (en) | 1980-01-05 |
| EP0007474B1 (en) | 1985-01-23 |
| YU41651B (en) | 1987-12-31 |
| ES482241A1 (es) | 1980-04-01 |
| YU163979A (en) | 1983-04-30 |
| NZ190914A (en) | 1981-05-01 |
| SU971103A3 (ru) | 1982-10-30 |
| JPS5942680B2 (ja) | 1984-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |