CZ292832B6 - Způsob přípravy silymarinu se zvýšenou rozpustností - Google Patents
Způsob přípravy silymarinu se zvýšenou rozpustností Download PDFInfo
- Publication number
- CZ292832B6 CZ292832B6 CZ20013153A CZ20013153A CZ292832B6 CZ 292832 B6 CZ292832 B6 CZ 292832B6 CZ 20013153 A CZ20013153 A CZ 20013153A CZ 20013153 A CZ20013153 A CZ 20013153A CZ 292832 B6 CZ292832 B6 CZ 292832B6
- Authority
- CZ
- Czechia
- Prior art keywords
- silymarin
- solution
- parts
- flavanolignans
- water
- Prior art date
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- SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound 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 66
- 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 title claims description 56
- 229960004245 silymarin Drugs 0.000 title claims description 38
- 235000017700 silymarin Nutrition 0.000 title claims description 38
- 230000001747 exhibiting effect Effects 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000243 solution Substances 0.000 claims abstract description 43
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- 239000012738 dissolution medium Substances 0.000 claims abstract description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000284 extract Substances 0.000 claims abstract description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract 2
- 229920001519 homopolymer Polymers 0.000 claims abstract 2
- 150000002576 ketones Chemical class 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- FDQAOULAVFHKBX-UHFFFAOYSA-N Isosilybin A Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC(=CC=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-UHFFFAOYSA-N 0.000 claims description 16
- 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 16
- 229940043175 silybin Drugs 0.000 claims description 16
- 235000014899 silybin Nutrition 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
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- 238000002360 preparation method Methods 0.000 claims description 11
- CYGIJEJDYJOUAN-UHFFFAOYSA-N Isosilychristin Natural products C1=C(O)C(OC)=CC(C2C3C=C(C4C(C3=O)(O)OCC42)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 CYGIJEJDYJOUAN-UHFFFAOYSA-N 0.000 claims description 10
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- 239000000600 sorbitol Substances 0.000 claims description 8
- 235000010356 sorbitol Nutrition 0.000 claims description 8
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 7
- 241000320380 Silybum Species 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 229930195725 Mannitol Natural products 0.000 claims description 6
- MZBGBHVFCYCYLX-UHFFFAOYSA-N Silydianin Natural products COc1cc(ccc1O)C2C3COC4(O)C3C=C(C5Oc6cc(O)cc(O)c6C(=O)C5O)C2C4=O MZBGBHVFCYCYLX-UHFFFAOYSA-N 0.000 claims description 6
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- FDQAOULAVFHKBX-DBMPWETRSA-N isosilybin Chemical compound C1=C(O)C(OC)=CC(C2C(OC3=CC(=CC=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-DBMPWETRSA-N 0.000 claims description 5
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- 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 claims description 3
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- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000004213 low-fat Nutrition 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 229960005502 α-amanitin Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
- A61K31/787—Polymers containing nitrogen containing heterocyclic rings having nitrogen as a ring hetero atom
- A61K31/79—Polymers of vinyl pyrrolidone
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20013153A CZ292832B6 (cs) | 2001-08-30 | 2001-08-30 | Způsob přípravy silymarinu se zvýšenou rozpustností |
| US10/487,651 US7384919B2 (en) | 2001-08-30 | 2002-08-30 | Increased solubility flavanolignan preparations |
| NZ531429A NZ531429A (en) | 2001-08-30 | 2002-08-30 | Increased solubility flavanolignan preparations |
| CA002458963A CA2458963A1 (en) | 2001-08-30 | 2002-08-30 | Increased solubility flavanolignan preparations |
| PCT/US2002/027713 WO2003020291A1 (en) | 2001-08-30 | 2002-08-30 | Increased solubility flavanolignan preparations |
| JP2003524598A JP2005519863A (ja) | 2001-08-30 | 2002-08-30 | 溶解性に優れたフラバノリグナン調製物 |
| AU2002323517A AU2002323517B2 (en) | 2001-08-30 | 2002-08-30 | Increased solubility flavanolignan preparations |
| KR10-2004-7002975A KR20040074052A (ko) | 2001-08-30 | 2002-08-30 | 증가된 용해도를 갖는 플라바노리그난 제제 |
| MXPA04001700A MXPA04001700A (es) | 2001-08-30 | 2002-08-30 | Preparaciones flavanolignano de solubilidad incrementada. |
| DE60224202T DE60224202T2 (de) | 2001-08-30 | 2002-08-30 | Erhöhte löslichkeit von flavanolignanzubereitungen |
| EP02757502A EP1420802B1 (en) | 2001-08-30 | 2002-08-30 | Increased solubility flavanolignan preparations |
| CNA028188268A CN1582159A (zh) | 2001-08-30 | 2002-08-30 | 增加了溶解度的黄烷醇木脂体制备物 |
| AT02757502T ATE381340T1 (de) | 2001-08-30 | 2002-08-30 | Erhöhte löslichkeit von flavanolignan- zubereitungen |
| TW091121077A TWI238065B (en) | 2001-08-30 | 2002-09-13 | Increased solubility flavanolignan preparations |
| NO20041300A NO20041300L (no) | 2001-08-30 | 2004-03-29 | Flavanolignanpreparater med okt loselighet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20013153A CZ292832B6 (cs) | 2001-08-30 | 2001-08-30 | Způsob přípravy silymarinu se zvýšenou rozpustností |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ20013153A3 CZ20013153A3 (cs) | 2003-04-16 |
| CZ292832B6 true CZ292832B6 (cs) | 2003-12-17 |
Family
ID=5473538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20013153A CZ292832B6 (cs) | 2001-08-30 | 2001-08-30 | Způsob přípravy silymarinu se zvýšenou rozpustností |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7384919B2 (https=) |
| EP (1) | EP1420802B1 (https=) |
| JP (1) | JP2005519863A (https=) |
| KR (1) | KR20040074052A (https=) |
| CN (1) | CN1582159A (https=) |
| AT (1) | ATE381340T1 (https=) |
| AU (1) | AU2002323517B2 (https=) |
| CA (1) | CA2458963A1 (https=) |
| CZ (1) | CZ292832B6 (https=) |
| DE (1) | DE60224202T2 (https=) |
| MX (1) | MXPA04001700A (https=) |
| NO (1) | NO20041300L (https=) |
| NZ (1) | NZ531429A (https=) |
| TW (1) | TWI238065B (https=) |
| WO (1) | WO2003020291A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009155887A1 (en) | 2008-06-26 | 2009-12-30 | Agra Group, A.S. | Composition of flavanolignan and amino acid with improved water solubility |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005026755A1 (de) * | 2005-06-09 | 2006-12-14 | Basf Ag | Herstellung von festen Lösungen schwerlöslicher Wirkstoffe durch Kurzzeitüberhitzung und schnelle Trocknung |
| WO2009052246A1 (en) | 2007-10-17 | 2009-04-23 | Ovokaitys, Todd, F. | Process for the modification of the solid state of a compound and co-amorphous compositions produced with same |
| DE102008039271A1 (de) * | 2007-12-23 | 2009-06-25 | Euromed Sa | Neuer Mariendistelextrakt, Verfahren zur Herstellung und Verwendung |
| JP5841048B2 (ja) * | 2009-05-14 | 2016-01-06 | エウロメッド・エセ・ア | ウイルス性肝炎の治療のための非晶質シリビニン |
| JP5698663B2 (ja) * | 2009-05-19 | 2015-04-08 | サントリーホールディングス株式会社 | フロフラン型リグナン４位グルコース転移酵素、及びそれをコードするポリヌクレオチド |
| CN102228430B (zh) * | 2011-06-14 | 2015-12-09 | 中国中医科学院中药研究所 | 水飞蓟宾磷脂复合物的纳米混悬剂及其制备方法 |
| US8877259B2 (en) | 2012-02-09 | 2014-11-04 | Mary Kay Inc. | Cosmetic formulation |
| ITMI20121317A1 (it) * | 2012-07-27 | 2014-01-28 | Indena Spa | Composizioni per il trattamento della fatica oncologica |
| JP2015113332A (ja) * | 2013-12-16 | 2015-06-22 | 花王株式会社 | 生薬粉体 |
| US10202598B2 (en) | 2014-05-30 | 2019-02-12 | Todd Frank Ovokaitys | Methods and systems for generation, use, and delivery of activated stem cells |
| US10384985B2 (en) | 2014-06-06 | 2019-08-20 | B.K. Consultants, Inc. | Methods and compositions for increasing the yield of, and beneficial chemical composition of, certain plants |
| US10040728B2 (en) | 2014-06-06 | 2018-08-07 | Todd Frank Ovokaitys | Methods and compositions for increasing the bioactivity of nutrients |
| JP6348024B2 (ja) * | 2014-09-03 | 2018-06-27 | 株式会社ファンケル | 水分散性の良いシリマリン含有組成物 |
| KR101598752B1 (ko) | 2015-01-28 | 2016-02-29 | 순천향대학교 산학협력단 | 표면적 및/또는 다공성이 조절된 당알콜을 담체로 이용한 리포솜 조성물 및 그의 제조방법 |
| ES2706008B8 (es) * | 2017-09-22 | 2021-07-12 | Euromed S A | Procedimiento para la preparacion de una composicion a partir del cardo mariano y composicion obtenida |
| WO2022126109A1 (en) | 2020-12-08 | 2022-06-16 | Ovokaitys Todd Frank | Methods and systems for increased production of stem cells |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1554662A (en) * | 1976-05-05 | 1979-10-24 | Inverni Della Beffa Spa | Polyhydroxyphenylchromanones |
| IT1215291B (it) * | 1985-07-17 | 1990-01-31 | Inverni Della Beffa Spa | Complessi di flavanolignani con fosfolipidi, loro preparazione e relative composizioni farmaceutiche. |
| US4767508A (en) * | 1986-02-27 | 1988-08-30 | Nippon Mining Co., Ltd. | Strike plating solution useful in applying primer plating to electronic parts |
| IT1222012B (it) * | 1987-07-10 | 1990-08-31 | Indena Spa | Composizioni farmaceutiche e cosmetiche contenenti complessi di flavonolignani con fosfolipidi |
| GB8716918D0 (en) * | 1987-07-17 | 1987-08-26 | Inverni Della Beffa Spa | Soluble derivatives of silybin |
| US5019562A (en) * | 1988-01-19 | 1991-05-28 | The Trustees Of The University Of Pennsylvania/Childrens Hospital Corporation | Growth inhibiting agent and the use thereof |
| IT1241673B (it) * | 1989-10-09 | 1994-01-27 | Istituto Biochimico Italiano | Complessi di inclusione di silibinina con ciclodestrina, loro preparazione e composizioni farmaceutiche che li contengono. |
| US5196448A (en) * | 1991-01-22 | 1993-03-23 | Stiefel Laboratories, Inc. | Antiinflammatory compositions and method of use |
| DE19501266A1 (de) * | 1995-01-18 | 1996-07-25 | Madaus Ag | Verfahren zur Herstellung von Flavano-Lignan-Zubereitungen mit verbesserter Freisetzung und Resorbierbarkeit danach erhältliche Zubereitungen und deren Verwendung zur Herstellung von Arzneimitteln |
| CZ287657B6 (cs) | 1996-06-12 | 2001-01-17 | Mikrobiologický Ústav Av Čr | Glykosidy silybininu a způsob jejich výroby |
| DE19744459A1 (de) | 1997-10-08 | 1999-04-15 | Schwabe Willmar Gmbh & Co | Flavonolignan-Zubereitungen, insbesondere Silymarin-Zubereitungen |
-
2001
- 2001-08-30 CZ CZ20013153A patent/CZ292832B6/cs not_active IP Right Cessation
-
2002
- 2002-08-30 CA CA002458963A patent/CA2458963A1/en not_active Abandoned
- 2002-08-30 DE DE60224202T patent/DE60224202T2/de not_active Expired - Lifetime
- 2002-08-30 JP JP2003524598A patent/JP2005519863A/ja active Pending
- 2002-08-30 EP EP02757502A patent/EP1420802B1/en not_active Expired - Lifetime
- 2002-08-30 WO PCT/US2002/027713 patent/WO2003020291A1/en not_active Ceased
- 2002-08-30 KR KR10-2004-7002975A patent/KR20040074052A/ko not_active Ceased
- 2002-08-30 CN CNA028188268A patent/CN1582159A/zh active Pending
- 2002-08-30 MX MXPA04001700A patent/MXPA04001700A/es active IP Right Grant
- 2002-08-30 AU AU2002323517A patent/AU2002323517B2/en not_active Expired - Fee Related
- 2002-08-30 AT AT02757502T patent/ATE381340T1/de not_active IP Right Cessation
- 2002-08-30 US US10/487,651 patent/US7384919B2/en not_active Expired - Fee Related
- 2002-08-30 NZ NZ531429A patent/NZ531429A/en not_active IP Right Cessation
- 2002-09-13 TW TW091121077A patent/TWI238065B/zh not_active IP Right Cessation
-
2004
- 2004-03-29 NO NO20041300A patent/NO20041300L/no not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009155887A1 (en) | 2008-06-26 | 2009-12-30 | Agra Group, A.S. | Composition of flavanolignan and amino acid with improved water solubility |
| US8426459B2 (en) | 2008-06-26 | 2013-04-23 | Agra Group, A.S. | Composition of flavanolignan and amino acid with improved water solubility |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050101546A1 (en) | 2005-05-12 |
| CZ20013153A3 (cs) | 2003-04-16 |
| DE60224202D1 (de) | 2008-01-31 |
| EP1420802A1 (en) | 2004-05-26 |
| WO2003020291A1 (en) | 2003-03-13 |
| US7384919B2 (en) | 2008-06-10 |
| DE60224202T2 (de) | 2008-12-04 |
| NO20041300L (no) | 2004-03-29 |
| EP1420802A4 (en) | 2005-02-09 |
| JP2005519863A (ja) | 2005-07-07 |
| AU2002323517B2 (en) | 2009-12-10 |
| CA2458963A1 (en) | 2003-03-13 |
| EP1420802B1 (en) | 2007-12-19 |
| MXPA04001700A (es) | 2005-04-11 |
| TWI238065B (en) | 2005-08-21 |
| CN1582159A (zh) | 2005-02-16 |
| KR20040074052A (ko) | 2004-08-21 |
| NZ531429A (en) | 2005-11-25 |
| ATE381340T1 (de) | 2008-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20070830 |