JPS60224697A - チゴゲニンセロビオシドおよび医薬 - Google Patents
チゴゲニンセロビオシドおよび医薬Info
- Publication number
- JPS60224697A JPS60224697A JP59153899A JP15389984A JPS60224697A JP S60224697 A JPS60224697 A JP S60224697A JP 59153899 A JP59153899 A JP 59153899A JP 15389984 A JP15389984 A JP 15389984A JP S60224697 A JPS60224697 A JP S60224697A
- Authority
- JP
- Japan
- Prior art keywords
- tigogenin
- formula
- compound
- anomer
- cellobioside
- 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.)
- Granted
Links
- RTMWIZOXNKJHRE-UHFFFAOYSA-N Tigogenin Natural products CC1COC2CC(C)(OC12)C3CCC4C5CCC6CC(O)CCC6(C)C5CCC34C RTMWIZOXNKJHRE-UHFFFAOYSA-N 0.000 title description 58
- GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 title description 53
- 239000003814 drug Substances 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 18
- WOTQVEKSRLZRSX-HYSGBLIFSA-N [(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1 WOTQVEKSRLZRSX-HYSGBLIFSA-N 0.000 claims description 15
- WOTQVEKSRLZRSX-UHFFFAOYSA-N beta-D-cellobioside octaacetate Natural products CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1 WOTQVEKSRLZRSX-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 11
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- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 80
- 235000012000 cholesterol Nutrition 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
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- 241000700159 Rattus Species 0.000 description 10
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 108010023302 HDL Cholesterol Proteins 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 4
- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 4
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 4
- WXMARHKAXWRNDM-GAMIEDRGSA-N diosgenin 3-O-beta-D-glucoside Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WXMARHKAXWRNDM-GAMIEDRGSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
- 102000007330 LDL Lipoproteins Human genes 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 239000008297 liquid dosage form Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229940075610 mercuric cyanide Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
- 230000004903 negative regulation of intestinal cholesterol absorption Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008136 water-miscible vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
- A61M15/0001—Details of inhalators; Constructional features thereof
- A61M15/0013—Details of inhalators; Constructional features thereof with inhalation check valves
- A61M15/0015—Details of inhalators; Constructional features thereof with inhalation check valves located upstream of the dispenser, i.e. not traversed by the product
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
- A61M15/0001—Details of inhalators; Constructional features thereof
- A61M15/0013—Details of inhalators; Constructional features thereof with inhalation check valves
- A61M15/0016—Details of inhalators; Constructional features thereof with inhalation check valves located downstream of the dispenser, i.e. traversed by the product
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
- A61M15/0086—Inhalation chambers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
- A61M15/009—Inhalators using medicine packages with incorporated spraying means, e.g. aerosol cans
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Biochemistry (AREA)
- Vascular Medicine (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cephalosporin Compounds (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US602298 | 1984-04-20 | ||
| US06/602,298 US4602005A (en) | 1982-05-17 | 1984-04-20 | Tigogenin cellobioside for treating hypercholesterolemia and atherosclerosis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60224697A true JPS60224697A (ja) | 1985-11-09 |
| JPH0456840B2 JPH0456840B2 (enExample) | 1992-09-09 |
Family
ID=24410793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59153899A Granted JPS60224697A (ja) | 1984-04-20 | 1984-07-23 | チゴゲニンセロビオシドおよび医薬 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4602005A (enExample) |
| EP (1) | EP0159431B1 (enExample) |
| JP (1) | JPS60224697A (enExample) |
| KR (1) | KR940002114B1 (enExample) |
| AT (1) | ATE42959T1 (enExample) |
| AU (1) | AU580005B2 (enExample) |
| CA (1) | CA1246544A (enExample) |
| DE (1) | DE3478114D1 (enExample) |
| DK (2) | DK165839C (enExample) |
| ES (1) | ES8601233A1 (enExample) |
| FI (2) | FI82253C (enExample) |
| HU (1) | HUT37802A (enExample) |
| IE (1) | IE58015B1 (enExample) |
| NO (1) | NO842990L (enExample) |
| NZ (1) | NZ208961A (enExample) |
| ZA (1) | ZA845690B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07504921A (ja) * | 1992-06-26 | 1995-06-01 | フアイザー・インコーポレイテツド | 高コレステロール血症を治療するためのステロイドグリコシド |
| JP2007515466A (ja) * | 2003-12-22 | 2007-06-14 | ビーティージー・インターナショナル・リミテッド | コア２ＧｌｃＮＡｃ−Ｔ阻害剤 |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4602005A (en) * | 1982-05-17 | 1986-07-22 | Medical Research Foundation Of Oregon | Tigogenin cellobioside for treating hypercholesterolemia and atherosclerosis |
| US4865850A (en) * | 1986-09-08 | 1989-09-12 | See/Shell Biotechnology, Inc. | Dietary fat reduction |
| US5010185A (en) * | 1989-06-13 | 1991-04-23 | Pfizer Inc. | Processes for tigogenin beta-cellobioside |
| US5091192A (en) * | 1990-01-16 | 1992-02-25 | Natur-All Systems, Inc. | Bile salts permanently bound to insoluble cellulose as a dietary supplement |
| EP0607245B1 (en) * | 1991-10-04 | 1998-04-22 | The Procter & Gamble Company | Cholesterol lowering compounds and process for making them |
| CA2079544A1 (en) * | 1991-10-04 | 1993-04-05 | Adam Weislaw Mazur | Cholesterol lowering compounds |
| WO1993011150A1 (en) * | 1991-11-25 | 1993-06-10 | Pfizer Inc. | Method for making steroidal peracyl glycosides |
| US5294703A (en) * | 1992-05-01 | 1994-03-15 | Eastman Kodak Company | Process for preparing α-D-cellobiose octaacetate |
| FI946081A0 (fi) * | 1992-06-26 | 1994-12-23 | Pfizer | Steroidaalinen beta-0-sellobiosidihepta-alkanoaattimenetelmä |
| FI946082L (fi) * | 1992-06-26 | 1994-12-23 | Pfizer | Menetelmä steroidisten perasyyliglykosidien valmistamiseksi |
| US5530107A (en) * | 1992-10-15 | 1996-06-25 | Pfizer Inc. | Method for making steroidal peracyl glycosides |
| WO1994025479A1 (en) * | 1993-04-28 | 1994-11-10 | Pfizer Inc. | Spirostanyl glycosidal crystalline monohydrate |
| US5502038A (en) * | 1993-06-21 | 1996-03-26 | Medical Research Foundation Of Oregon | Cholesterol sequestrant glycosides that inhibit intestinal cholesterol absorption |
| WO1995000158A1 (en) * | 1993-06-25 | 1995-01-05 | Bio-Sphere Technology | Dietary supplement incorporating beta-sitosterol and pectin |
| ES2074006B1 (es) * | 1993-07-05 | 1996-03-16 | Pfizer | Glicosidos esteroidales para tratar hipercolesterolemia. |
| AU7948494A (en) * | 1993-12-28 | 1995-07-17 | Pfizer Inc. | Steroidal glycosides |
| US5607841A (en) * | 1994-06-20 | 1997-03-04 | Lipinski; Boguslaw | Preparation and proteolytic degradation of a macromolecular protein complex from fibrinogen |
| US5807834A (en) * | 1994-09-20 | 1998-09-15 | Pfizer Inc. | Combination of a cholesterol absorption inhibitor and a cholesterol synthesis inhibitor |
| WO1996038466A1 (en) * | 1995-05-29 | 1996-12-05 | Pfizer Inc. | Steroidal glycosides |
| US5698527A (en) * | 1995-08-08 | 1997-12-16 | Merck & Co., Inc. | Steroidal glycosides as antihyperlipidemic agents |
| US5756470A (en) * | 1996-10-29 | 1998-05-26 | Schering Corporation | Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents |
| GB9923076D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| DK1066042T3 (da) * | 1998-03-26 | 2006-12-18 | Phytopharm Plc | Steroidale saponiner til behandling af Alzheimers sygdom |
| GB9923078D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB9923077D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB0000228D0 (en) * | 2000-01-06 | 2000-03-01 | Phytopharm Plc | Fluoro substituted sapogenins and their use |
| US6982251B2 (en) * | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
| KR20040025890A (ko) * | 2001-01-26 | 2004-03-26 | 쉐링 코포레이션 | 혈관성 질환을 치료하기 위한 스테롤 흡수 억제제와 혈액조절제의 조합물 |
| EP1413331B1 (en) * | 2001-01-26 | 2007-10-03 | Schering Corporation | Combinations of the peroxisome proliferator-activated receptor (PPAR) activator fenofibrate with sterol absorption inhibitor ezetimibe for vascular indications |
| MXPA03006727A (es) * | 2001-01-26 | 2003-10-24 | Schering Corp | Combinaciones de acido nicotinico y derivados del mismo con inhibidor(es) de la absorcion de los esteroles, y tratamiento para indicaciones vasculares. |
| DK1385548T3 (da) * | 2001-01-26 | 2007-09-10 | Schering Corp | Kombinationer af sterolabsorptionsinhibitor(er) med (et eller flere) kardiovaskulære midler til behandling af vaskulære tilstande |
| KR20070120617A (ko) * | 2001-01-26 | 2007-12-24 | 쉐링 코포레이션 | 치환된 아제티딘온 화합물을 포함하는 약제학적 조성물 |
| EP1785144A3 (en) * | 2001-01-26 | 2007-05-23 | Shering Corporation | Combinations of bile acid sequestrant(s) and sterol absorption inhibitor(s) and treatments for vascular indications |
| US7071181B2 (en) * | 2001-01-26 | 2006-07-04 | Schering Corporation | Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors |
| GB0107822D0 (en) * | 2001-03-28 | 2001-05-23 | Phytopharm Plc | Sapogenin derivatives their synthesis and use methods based upon their use |
| ATE345792T1 (de) * | 2001-05-25 | 2006-12-15 | Schering Corp | Verwendung von mit azetidinon substituierten derivaten bei der behandlung der alzheimer- krankheit |
| US7053080B2 (en) * | 2001-09-21 | 2006-05-30 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors |
| DE60216300T2 (de) * | 2001-09-21 | 2007-06-28 | Schering Corp. | Behandlung von xanthom mittels azetidinon-derivate als hemmer der sterol absorption |
| US7056906B2 (en) * | 2001-09-21 | 2006-06-06 | Schering Corporation | Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women |
| NZ531060A (en) * | 2001-09-21 | 2006-06-30 | Schering Corp | Methods for treating or preventing vascular inflammation using sterol absorption inhibitor(s) |
| US20030119808A1 (en) * | 2001-09-21 | 2003-06-26 | Schering Corporation | Methods of treating or preventing cardiovascular conditions while preventing or minimizing muscular degeneration side effects |
| CN102727501A (zh) * | 2002-03-27 | 2012-10-17 | 菲特法姆股份有限公司 | 皂角苷配基及其衍生物的用途 |
| US20050130948A1 (en) * | 2002-03-27 | 2005-06-16 | Daryl Rees | Therapeutic methods and uses of sapogenins and their derivatives |
| CA2504916A1 (en) * | 2002-11-06 | 2004-05-27 | Schering Corporation | Cholesterol absorptions inhibitors for the treatment of autoimmune disorders |
| DE602004018617D1 (de) | 2003-03-07 | 2009-02-05 | Schering Corp | Substituierte azetidinon-derivate, deren pharmazeutische formulierungen und deren verwendung zur behandlung von hypercholesterolemia |
| US7459442B2 (en) | 2003-03-07 | 2008-12-02 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
| CA2517573C (en) * | 2003-03-07 | 2011-12-06 | Schering Corporation | Substituted azetidinone compounds, formulations and uses thereof for the treatment of hypercholesterolemia |
| MXPA05009503A (es) | 2003-03-07 | 2005-10-18 | Schering Corp | Compuestos de azetidinona sustituidos, formulaciones y usos de los mismos para el tratamiento de hipercolesterolemia. |
| JP2007510659A (ja) * | 2003-11-05 | 2007-04-26 | シェーリング コーポレイション | 脂質調節剤および置換アゼチジノンの組み合わせならびに血管状態の処置 |
| WO2005063790A1 (en) * | 2003-12-31 | 2005-07-14 | Council Of Scientific & Industrial Research | Isolation of tigogenin pentaglycoside from chlorophytum nimonii |
| US7160866B2 (en) | 2004-03-22 | 2007-01-09 | Council Of Scientific And Industrial Research | Isolation of tigogenin pentaglycoside from Chlorophytum nimonii |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2759171A1 (de) * | 1977-12-31 | 1979-07-12 | Roecar Holdings Nv | Arzneimittel mit wirkung als prostaglandinsynthetaseninhibitor |
| DE2926463A1 (de) * | 1978-07-05 | 1980-01-24 | Roecar Holdings Nv | Spiroketaline und ihre verwendung |
| US4260603A (en) * | 1979-01-02 | 1981-04-07 | Pegel Karl H | Sterol glycoside with activity as prostaglandin synthetase inhibitor |
| US4242502A (en) * | 1979-04-20 | 1980-12-30 | United States Of America | Enhancement of cholesterol combining properties of saponins |
| US4602005A (en) * | 1982-05-17 | 1986-07-22 | Medical Research Foundation Of Oregon | Tigogenin cellobioside for treating hypercholesterolemia and atherosclerosis |
| 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 |
-
1984
- 1984-04-20 US US06/602,298 patent/US4602005A/en not_active Expired - Lifetime
- 1984-07-20 NZ NZ208961A patent/NZ208961A/en unknown
- 1984-07-23 AT AT84304993T patent/ATE42959T1/de not_active IP Right Cessation
- 1984-07-23 AU AU30977/84A patent/AU580005B2/en not_active Ceased
- 1984-07-23 HU HU842837A patent/HUT37802A/hu unknown
- 1984-07-23 NO NO842990A patent/NO842990L/no unknown
- 1984-07-23 KR KR1019840004369A patent/KR940002114B1/ko not_active Expired - Fee Related
- 1984-07-23 DK DK361084A patent/DK165839C/da not_active IP Right Cessation
- 1984-07-23 CA CA000459491A patent/CA1246544A/en not_active Expired
- 1984-07-23 DE DE8484304993T patent/DE3478114D1/de not_active Expired
- 1984-07-23 EP EP84304993A patent/EP0159431B1/en not_active Expired
- 1984-07-23 ZA ZA845690A patent/ZA845690B/xx unknown
- 1984-07-23 JP JP59153899A patent/JPS60224697A/ja active Granted
- 1984-07-23 ES ES534553A patent/ES8601233A1/es not_active Expired
- 1984-07-23 IE IE190484A patent/IE58015B1/en not_active IP Right Cessation
- 1984-07-23 FI FI842935A patent/FI82253C/fi not_active IP Right Cessation
-
1990
- 1990-02-02 FI FI900531A patent/FI87792C/fi not_active IP Right Cessation
-
1992
- 1992-02-06 DK DK014892A patent/DK166213C/da not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07504921A (ja) * | 1992-06-26 | 1995-06-01 | フアイザー・インコーポレイテツド | 高コレステロール血症を治療するためのステロイドグリコシド |
| JP2007515466A (ja) * | 2003-12-22 | 2007-06-14 | ビーティージー・インターナショナル・リミテッド | コア２ＧｌｃＮＡｃ−Ｔ阻害剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| FI82253B (fi) | 1990-10-31 |
| DK361084A (da) | 1985-10-21 |
| AU3097784A (en) | 1985-10-24 |
| DK14892D0 (da) | 1992-02-06 |
| US4602005A (en) | 1986-07-22 |
| DK361084D0 (da) | 1984-07-23 |
| DE3478114D1 (en) | 1989-06-15 |
| FI900531A0 (fi) | 1990-02-02 |
| ES534553A0 (es) | 1985-11-16 |
| FI842935A0 (fi) | 1984-07-23 |
| DK165839C (da) | 1993-06-21 |
| FI82253C (fi) | 1991-02-11 |
| CA1246544A (en) | 1988-12-13 |
| JPH0456840B2 (enExample) | 1992-09-09 |
| NO842990L (no) | 1985-10-21 |
| HUT37802A (en) | 1986-02-28 |
| FI87792B (fi) | 1992-11-13 |
| EP0159431A2 (en) | 1985-10-30 |
| EP0159431A3 (en) | 1986-01-08 |
| KR850007432A (ko) | 1985-12-04 |
| EP0159431B1 (en) | 1989-05-10 |
| ES8601233A1 (es) | 1985-11-16 |
| ZA845690B (en) | 1986-03-26 |
| ATE42959T1 (de) | 1989-05-15 |
| FI842935L (fi) | 1985-10-21 |
| DK166213C (da) | 1993-08-16 |
| DK14892A (da) | 1992-02-06 |
| DK165839B (da) | 1993-01-25 |
| DK166213B (da) | 1993-03-22 |
| KR940002114B1 (ko) | 1994-03-17 |
| IE841904L (en) | 1985-10-20 |
| IE58015B1 (en) | 1993-06-16 |
| AU580005B2 (en) | 1988-12-22 |
| FI87792C (fi) | 1993-02-25 |
| NZ208961A (en) | 1988-01-08 |
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