PL146890B1 - Process for preparing novel derivatives of silibinin - Google Patents
Process for preparing novel derivatives of silibinin Download PDFInfo
- Publication number
- PL146890B1 PL146890B1 PL1985256374A PL25637485A PL146890B1 PL 146890 B1 PL146890 B1 PL 146890B1 PL 1985256374 A PL1985256374 A PL 1985256374A PL 25637485 A PL25637485 A PL 25637485A PL 146890 B1 PL146890 B1 PL 146890B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- silibinin
- alk
- animals
- sili
- Prior art date
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- 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 title claims description 44
- 238000004519 manufacturing process Methods 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 43
- 241001465754 Metazoa Species 0.000 claims description 36
- 235000014899 silybin Nutrition 0.000 claims description 31
- 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 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 229950000628 silibinin Drugs 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
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- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
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- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 231100000152 severe skin burn Toxicity 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- SEBFKMXJBCUCAI-DBMPWETRSA-N silybin Chemical compound C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-DBMPWETRSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 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
- 230000035899 viability Effects 0.000 description 1
- 239000002699 waste material 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Dermatology (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 (2)
| Publication Number | Publication Date |
|---|---|
| PL256374A1 PL256374A1 (en) | 1986-12-02 |
| PL146890B1 true PL146890B1 (en) | 1989-03-31 |
Family
ID=6250903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1985256374A PL146890B1 (en) | 1984-11-22 | 1985-11-21 | Process for preparing novel derivatives of silibinin |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS61143377A (hu) |
| KR (1) | KR870001020B1 (hu) |
| AR (1) | AR240931A1 (hu) |
| AT (1) | AT393268B (hu) |
| BE (1) | BE903693A (hu) |
| CA (1) | CA1337124C (hu) |
| CH (1) | CH659473A5 (hu) |
| CS (1) | CS273610B2 (hu) |
| DD (1) | DD259191A1 (hu) |
| DE (1) | DE3442639A1 (hu) |
| DK (1) | DK164865C (hu) |
| EG (1) | EG19424A (hu) |
| ES (1) | ES8609311A1 (hu) |
| FI (1) | FI84064C (hu) |
| FR (1) | FR2573427B1 (hu) |
| GB (1) | GB2167414B (hu) |
| HU (1) | HU195503B (hu) |
| IE (1) | IE58791B1 (hu) |
| IT (1) | IT1190426B (hu) |
| LU (1) | LU86163A1 (hu) |
| MX (1) | MX168415B (hu) |
| NL (1) | NL192387C (hu) |
| NO (1) | NO160205C (hu) |
| PL (1) | PL146890B1 (hu) |
| PT (1) | PT81532B (hu) |
| SE (1) | SE465676B (hu) |
| SU (1) | SU1436875A3 (hu) |
| YU (1) | YU43689B (hu) |
| ZA (1) | ZA858951B (hu) |
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 |
| NZ560633A (en) * | 2005-03-11 | 2011-08-26 | Neuprotect Pty Ltd | Flavonoid compounds and uses thereof |
| RU2482844C2 (ru) * | 2007-11-15 | 2013-05-27 | Мадаус Гмбх | Силибининовый компонент для лечения гепатита |
| MX2010005107A (es) * | 2007-11-15 | 2010-05-27 | Madaus Gmbh | Componente de silibinina para tratamiento contra hepatitis. |
| CA2761656C (en) | 2009-05-14 | 2017-02-07 | Lucio Claudio Rovati | Amorphous silibinin for the treatment of viral hepatitis |
| CN108355136B (zh) | 2012-07-05 | 2021-12-07 | 纽崔玛氏科技有限责任公司 | 包含莱菔硫烷或莱菔硫烷前体和蕈类提取物或粉末的组合物 |
| 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 CS CS837885A patent/CS273610B2/cs unknown
- 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
- 1985-11-21 ZA ZA858951A patent/ZA858951B/xx unknown
- 1985-11-21 IT IT22932/85A patent/IT1190426B/it active
- 1985-11-21 PL PL1985256374A patent/PL146890B1/pl unknown
- 1985-11-21 NO NO854655A patent/NO160205C/no not_active IP Right Cessation
- 1985-11-21 EG EG74085A patent/EG19424A/xx active
- 1985-11-21 DK DK537785A patent/DK164865C/da not_active IP Right Cessation
- 1985-11-21 ES ES549116A patent/ES8609311A1/es not_active Expired
- 1985-11-21 HU HU854448A patent/HU195503B/hu not_active IP Right Cessation
- 1985-11-21 PT PT81532A patent/PT81532B/pt not_active IP Right Cessation
- 1985-11-21 SU SU853985401A patent/SU1436875A3/ru active
- 1985-11-22 JP JP60261629A patent/JPS61143377A/ja active Granted
- 1985-11-22 FR FR858517321A patent/FR2573427B1/fr not_active Expired
- 1985-11-22 MX MX009022A patent/MX168415B/es unknown
- 1985-11-22 KR KR1019850008733A patent/KR870001020B1/ko not_active IP Right Cessation
- 1985-11-22 BE BE2/60850A patent/BE903693A/fr not_active IP Right Cessation
Also Published As
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