CH659473A5 - Flavolignanderivate, verfahren zu deren herstellung und arzneimittel, die diese verbindungen enthalten. - Google Patents
Flavolignanderivate, verfahren zu deren herstellung und arzneimittel, die diese verbindungen enthalten. Download PDFInfo
- Publication number
- CH659473A5 CH659473A5 CH4935/85A CH493585A CH659473A5 CH 659473 A5 CH659473 A5 CH 659473A5 CH 4935/85 A CH4935/85 A CH 4935/85A CH 493585 A CH493585 A CH 493585A CH 659473 A5 CH659473 A5 CH 659473A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alk
- silybin
- formula
- silibinin
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229940126601 medicinal product Drugs 0.000 title 1
- SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical class C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 claims description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 claims description 35
- 235000014899 silybin Nutrition 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 229950000628 silibinin Drugs 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
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- VLGROHBNWZUINI-UHFFFAOYSA-N Silybin Natural products COc1cc(ccc1O)C2OC3C=C(C=CC3OC2CO)C4Oc5cc(O)cc(O)c5C(=O)C4O VLGROHBNWZUINI-UHFFFAOYSA-N 0.000 claims description 15
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 7
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- FDQAOULAVFHKBX-HKTJVKLFSA-N (2r,3r)-3,5,7-trihydroxy-2-[(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC(=CC=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-HKTJVKLFSA-N 0.000 claims description 2
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- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 235000019643 salty taste Nutrition 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 231100000152 severe skin burn Toxicity 0.000 description 1
- 229950004878 silicristin Drugs 0.000 description 1
- 229950004304 silidianin Drugs 0.000 description 1
- BMLIIPOXVWESJG-LMBCONBSSA-N silychristin Chemical compound C1=C(O)C(OC)=CC([C@H]2[C@@H](C3=C(C(=CC(=C3)[C@@H]3[C@H](C(=O)C4=C(O)C=C(O)C=C4O3)O)O)O2)CO)=C1 BMLIIPOXVWESJG-LMBCONBSSA-N 0.000 description 1
- BMLIIPOXVWESJG-UHFFFAOYSA-N silychristin A Natural products C1=C(O)C(OC)=CC(C2C(C3=C(C(=CC(=C3)C3C(C(=O)C4=C(O)C=C(O)C=C4O3)O)O)O2)CO)=C1 BMLIIPOXVWESJG-UHFFFAOYSA-N 0.000 description 1
- CYGIJEJDYJOUAN-JSGXPVSSSA-N silydianin Chemical compound C1=C(O)C(OC)=CC([C@H]2[C@H]3C=C([C@@H]4[C@@](C3=O)(O)OC[C@@H]42)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 CYGIJEJDYJOUAN-JSGXPVSSSA-N 0.000 description 1
- 229960004245 silymarin Drugs 0.000 description 1
- 235000017700 silymarin Nutrition 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Silicon Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843442639 DE3442639A1 (de) | 1984-11-22 | 1984-11-22 | Flavolignanderivate, verfahren zu deren herstellung und arzneimittel, die diese verbindungen enthalten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH659473A5 true CH659473A5 (de) | 1987-01-30 |
Family
ID=6250903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4935/85A CH659473A5 (de) | 1984-11-22 | 1985-11-19 | Flavolignanderivate, verfahren zu deren herstellung und arzneimittel, die diese verbindungen enthalten. |
Country Status (29)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8716918D0 (en) * | 1987-07-17 | 1987-08-26 | Inverni Della Beffa Spa | Soluble derivatives of silybin |
| US5262439A (en) * | 1992-04-30 | 1993-11-16 | The Regents Of The University Of California | Soluble analogs of probucol |
| ES2552108T3 (es) * | 2005-03-11 | 2015-11-25 | Howard Florey Institute Pty Ltd | Compuestos flavonoides y usos de los mismos |
| WO2009062737A1 (en) * | 2007-11-15 | 2009-05-22 | Madaus Gmbh | Silibinin component for the treatment of hepatitis |
| RU2482844C2 (ru) * | 2007-11-15 | 2013-05-27 | Мадаус Гмбх | Силибининовый компонент для лечения гепатита |
| TWI529167B (zh) | 2009-05-14 | 2016-04-11 | 歐羅梅德股份有限公司 | 用於治療病毒性肝炎之非晶型水飛薊賓 |
| RU2666953C2 (ru) | 2012-07-05 | 2018-09-13 | Нутрамакс Лабораториз, Инк. | Композиции, содержащие сульфорафан или предшественник сульфорафана и экстракт или порошок молочного чертополоха |
| CN103172622B (zh) * | 2013-02-22 | 2015-11-04 | 西安安健药业有限公司 | 水飞蓟宾二偏琥珀酸酯的活性异构体 |
| CN103193768B (zh) * | 2013-02-22 | 2016-03-30 | 西安安健药业有限公司 | 治疗肝病的水飞蓟宾二偏琥珀酸酯异构体 |
| CN103113359B (zh) * | 2013-02-22 | 2016-01-06 | 西安安健药业有限公司 | 水飞蓟宾二偏琥珀酸酯及其药用盐 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1963318A1 (de) * | 1969-12-17 | 1971-06-24 | Schwabe Willmar Gmbh & Co | Silybinhalbester der Bernsteinsaeure und der Phthalsaeure,ihre Salze mit pharmakologisch vertraglichen Basen,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneipraeparaten |
-
1984
- 1984-11-22 DE DE19843442639 patent/DE3442639A1/de active Granted
-
1985
- 1985-11-11 IE IE280885A patent/IE58791B1/en not_active IP Right Cessation
- 1985-11-13 LU LU86163A patent/LU86163A1/de unknown
- 1985-11-14 AR AR302267A patent/AR240931A1/es active
- 1985-11-14 YU YU1786/85A patent/YU43689B/xx unknown
- 1985-11-15 GB GB08528226A patent/GB2167414B/en not_active Expired
- 1985-11-18 FI FI854535A patent/FI84064C/fi not_active IP Right Cessation
- 1985-11-18 NL NL8503171A patent/NL192387C/nl not_active IP Right Cessation
- 1985-11-19 AT AT3371/85A patent/AT393268B/de not_active IP Right Cessation
- 1985-11-19 CH CH4935/85A patent/CH659473A5/de not_active IP Right Cessation
- 1985-11-20 SE SE8505487A patent/SE465676B/sv not_active IP Right Cessation
- 1985-11-20 CA CA000495804A patent/CA1337124C/en not_active Expired - Fee Related
- 1985-11-20 DD DD85283042A patent/DD259191A1/de not_active IP Right Cessation
- 1985-11-20 CS CS837885A patent/CS273610B2/cs unknown
- 1985-11-21 ES ES549116A patent/ES8609311A1/es not_active Expired
- 1985-11-21 PL PL1985256374A patent/PL146890B1/pl unknown
- 1985-11-21 PT PT81532A patent/PT81532B/pt not_active IP Right Cessation
- 1985-11-21 SU SU853985401A patent/SU1436875A3/ru active
- 1985-11-21 HU HU854448A patent/HU195503B/hu not_active IP Right Cessation
- 1985-11-21 ZA ZA858951A patent/ZA858951B/xx unknown
- 1985-11-21 EG EG74085A patent/EG19424A/xx active
- 1985-11-21 NO NO854655A patent/NO160205C/no not_active IP Right Cessation
- 1985-11-21 DK DK537785A patent/DK164865C/da not_active IP Right Cessation
- 1985-11-21 IT IT22932/85A patent/IT1190426B/it active
- 1985-11-22 JP JP60261629A patent/JPS61143377A/ja active Granted
- 1985-11-22 BE BE2/60850A patent/BE903693A/fr not_active IP Right Cessation
- 1985-11-22 MX MX009022A patent/MX168415B/es unknown
- 1985-11-22 FR FR858517321A patent/FR2573427B1/fr not_active Expired
- 1985-11-22 KR KR1019850008733A patent/KR870001020B1/ko not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: MADAUS AG |
|
| PL | Patent ceased |