NL192204C - Werkwijze voor het bereiden van isosilybine-vrij silibinine en farmaceutisch preparaat dat isosilybine-vrij silibinine bevat. - Google Patents

Werkwijze voor het bereiden van isosilybine-vrij silibinine en farmaceutisch preparaat dat isosilybine-vrij silibinine bevat. Download PDF

Info

Publication number: NL192204C
Authority: NL; Netherlands
Prior art keywords: weight; ethyl acetate; parts; hours; isosilybin
Prior art date: 1984-11-22

Application number

NL8503136A

Other languages

English (en)

Dutch (nl)

Other versions

NL8503136A (nl

NL192204B (nl

Original Assignee

Madaus Ag

Priority date (The priority date 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 date listed.)

1984-11-22

Filing date

1985-11-14

Publication date

1997-03-04

1985-11-14 Application filed by Madaus Ag filed Critical Madaus Ag

1986-06-16 Publication of NL8503136A publication Critical patent/NL8503136A/nl

1996-11-01 Publication of NL192204B publication Critical patent/NL192204B/xx

1997-03-04 Application granted granted Critical

1997-03-04 Publication of NL192204C publication Critical patent/NL192204C/nl

Links

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 84
238000000034 method Methods 0.000 title claims description 13
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 85
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 59
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
235000014899 silybin Nutrition 0.000 claims description 48
229950000628 silibinin Drugs 0.000 claims description 40
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
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 18
239000000047 product Substances 0.000 claims description 17
239000002244 precipitate Substances 0.000 claims description 13
239000012141 concentrate Substances 0.000 claims description 12
FDQAOULAVFHKBX-KMRPREKFSA-N (+)-Isosilybin A Natural products 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-KMRPREKFSA-N 0.000 claims description 10
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 10
KDMGQPNVTKUNHV-UHFFFAOYSA-N Isosilybin Natural products C1=C(O)C(OC)=CC=C1C1C(CO)OC2=CC=C(C3C(C(=O)C4=C(O)C=C(O)C=C4O3)O)C=C2O1 KDMGQPNVTKUNHV-UHFFFAOYSA-N 0.000 claims description 10
239000000843 powder Substances 0.000 claims description 10
238000003756 stirring Methods 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
238000009835 boiling Methods 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
238000001035 drying Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
238000001914 filtration Methods 0.000 claims description 6
239000000706 filtrate Substances 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
239000000284 extract Substances 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
230000004083 survival effect Effects 0.000 claims description 4
244000272459 Silybum marianum Species 0.000 claims description 3
235000010841 Silybum marianum Nutrition 0.000 claims description 3
238000001704 evaporation Methods 0.000 claims description 3
230000035987 intoxication Effects 0.000 claims description 3
231100000566 intoxication Toxicity 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 3
241000699670 Mus sp. Species 0.000 claims description 2
230000009172 bursting Effects 0.000 claims description 2
238000009826 distribution Methods 0.000 claims description 2
235000011869 dried fruits Nutrition 0.000 claims description 2
235000013399 edible fruits Nutrition 0.000 claims description 2
230000008020 evaporation Effects 0.000 claims description 2
239000010685 fatty oil Substances 0.000 claims description 2
239000003921 oil Substances 0.000 claims description 2
239000003208 petroleum Substances 0.000 claims description 2
238000003825 pressing Methods 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000011877 solvent mixture Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 1
238000004090 dissolution Methods 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
235000017700 silymarin Nutrition 0.000 description 13
229960004245 silymarin Drugs 0.000 description 11
VLGROHBNWZUINI-UHFFFAOYSA-N Silybin Natural products COc1cc(ccc1O)C2OC3C=C(C=CC3OC2CO)C4Oc5cc(O)cc(O)c5C(=O)C4O VLGROHBNWZUINI-UHFFFAOYSA-N 0.000 description 8
229940043175 silybin Drugs 0.000 description 8
239000000902 placebo Substances 0.000 description 6
229940068196 placebo Drugs 0.000 description 6
210000004185 liver Anatomy 0.000 description 5
231100000572 poisoning Toxicity 0.000 description 5
230000000607 poisoning effect Effects 0.000 description 5
208000019425 cirrhosis of liver Diseases 0.000 description 3
208000019423 liver disease Diseases 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
206010067125 Liver injury Diseases 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000470 constituent Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-UHFFFAOYSA-N 6-(methylamino)hexane-1,2,3,4,5-pentol Chemical class CNCC(O)C(O)C(O)C(O)CO MBBZMMPHUWSWHV-UHFFFAOYSA-N 0.000 description 1
208000022309 Alcoholic Liver disease Diseases 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
102000015790 Asparaginase Human genes 0.000 description 1
108010024976 Asparaginase Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
206010016654 Fibrosis Diseases 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000001929 anti-hepatotoxic effect Effects 0.000 description 1
229960003272 asparaginase Drugs 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000036765 blood level Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
229960001076 chlorpromazine Drugs 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000007882 cirrhosis Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
230000035876 healing Effects 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
231100000753 hepatic injury Toxicity 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
230000000698 schizophrenic effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F16L59/00—Thermal insulation in general
- F16L59/04—Arrangements using dry fillers, e.g. using slag wool

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
General Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Mechanical Engineering (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Plural Heterocyclic Compounds (AREA)
Cephalosporin Compounds (AREA)

NL8503136A 1984-11-22 1985-11-14 Werkwijze voor het bereiden van isosilybine-vrij silibinine en farmaceutisch preparaat dat isosilybine-vrij silibinine bevat. NL192204C (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE3442641		1984-11-22
DE3442641		1984-11-22
DE3537656		1985-10-23
DE19853537656 DE3537656A1 (de)	1984-11-22	1985-10-23	Verfahren zur herstellung von isosilybinfreiem silibinin und arzneimittel, enthaltend silibinin

Publications (3)

Publication Number	Publication Date
NL8503136A NL8503136A (nl)	1986-06-16
NL192204B NL192204B (nl)	1996-11-01
NL192204C true NL192204C (nl)	1997-03-04

Family

ID=25826741

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8503136A NL192204C (nl)	1984-11-22	1985-11-14	Werkwijze voor het bereiden van isosilybine-vrij silibinine en farmaceutisch preparaat dat isosilybine-vrij silibinine bevat.

Country Status (26)

Country	Link
US (1)	US4871763A (xx)
JP (1)	JPH0678228B2 (xx)
AR (1)	AR241268A1 (xx)
AT (1)	AT391315B (xx)
BE (1)	BE903694A (xx)
CA (1)	CA1337125C (xx)
CH (1)	CH660008A5 (xx)
CS (1)	CS271321B2 (xx)
DE (1)	DE3537656A1 (xx)
DK (3)	DK166541B1 (xx)
EG (1)	EG17710A (xx)
ES (2)	ES8609312A1 (xx)
FI (1)	FI84065C (xx)
FR (1)	FR2573426B1 (xx)
GB (1)	GB2167746B (xx)
HU (1)	HU195504B (xx)
IE (1)	IE59209B1 (xx)
IT (1)	IT1207508B (xx)
LU (1)	LU86164A1 (xx)
MX (1)	MX172175B (xx)
NL (1)	NL192204C (xx)
NO (1)	NO160206C (xx)
PL (1)	PL146889B1 (xx)
PT (1)	PT81531B (xx)
SE (1)	SE457957B (xx)
YU (1)	YU43690B (xx)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3357383B2 (ja) *	1991-08-14	2002-12-16	昌宏黒田	低分子化植物性組成物
DE4401902C2 (de) *	1994-01-24	2000-02-03	Madaus Ag	Verwendung von Flavolignanen als Adjuvans in der Tumortherapie
FR2719451B1 (fr) *	1994-05-04	1996-07-26	Apcis Sa	Utilisation de la silybinine dans le gavage des palmipèdes, en vue de l'obtention d'un foie gras de meilleure qualité.
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
US6379714B1 (en)	1995-04-14	2002-04-30	Pharmaprint, Inc.	Pharmaceutical grade botanical drugs
DE69824223T2 (de)	1997-03-19	2004-09-30	Unilever N.V.	Vorrichtung zum Handhaben von Gegenständen
GB2327607B8 (en) *	1997-07-31	2005-03-30	Litton Internat Company Ltd	A process for producing a herbal extract composition
DE10053384A1 (de) *	2000-10-27	2002-05-08	Bionorica Arzneimittel Gmbh	Pharmazeutische Zubereitung aus Mariendistel und Terpenen
US6699900B2 (en) *	2001-04-07	2004-03-02	Jan E. Zielinski	Hydrophilic and lipophilic silibinin pro-forms
DE10360954B3 (de) *	2003-12-23	2005-08-18	Esparma Gmbh	Verwendung von Silibinin, dessen Salzen und/oder dessen Prodrugs zusammen mit α-Liponsäure zur Behandlung chronisch obstruktiver Lungenerkrankungen
BG65997B1 (bg) *	2005-03-29	2010-09-30	"Софарма" Ад	Метод за получаване на силибинин
WO2009062737A1 (en) *	2007-11-15	2009-05-22	Madaus Gmbh	Silibinin component for the treatment of hepatitis
AU2010247716B2 (en) *	2009-05-14	2015-11-05	Madaus Gmbh	Amorphous silibinin for the treatment of viral hepatitis
WO2011051742A1 (en) *	2009-10-28	2011-05-05	Modutech S.A.	Preparation comprising amino acids and plants and its activity in the alcohol detoxification
CN103408539B (zh) *	2013-08-28	2016-04-06	天津泰阳制药有限公司	高纯度水飞蓟宾的生产方法
WO2017121855A1 (en) *	2016-01-15	2017-07-20	Universität Hamburg	Flavonoide-type compounds bearing an o-rhamnosyl residue
EP4232055A4 (en)	2020-09-29	2024-10-02	Munisekhar Medasani	EXTRACTION OF BIOACTIVE COMPOUNDS FROM MILK THISTLE PLANT MATERIALS AND USE

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3773932A (en) *	1968-06-01	1973-11-20	Madaus & Co Dr	Method for recovering silymarin comprising polyhydroxyphenyl chromanones
DE1767666C3 (de) *	1968-06-01	1986-07-31	Dr. Madaus & Co, 5000 Koeln	Pharmazeutische Zubereitung gegen Lebererkrankungen
DE1923082C3 (de) *	1969-05-06	1985-08-22	Dr. Madaus & Co, 5000 Koeln	Verfahren zur Gewinnung von Polyhydroxyphenylchromanonen (Silymarin I-IV) und Arzneimittel enthaltend das Polyhydroxyphenylchromanon (Silymarin I-IV = Silymarin I-IV-Gruppe)Gemisch
DE2416302B2 (de) *	1974-04-04	1978-02-02	Dr. Madaus & Co, 5000 Köln	Dimeres sowie trimeres silybin und deren n-methylglucaminsalz und verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
BE885558A (fr) *	1980-10-07	1981-04-07	Madaus & Co Dr	Procede pour l'extraction de silymarine a partir des plantes silymarine ainsi obtenue et son utilisation en therapeutique
DE3225688A1 (de) *	1982-07-09	1984-01-12	Suschnik Matthias Dr	Verfahren zur gewinnung von silymarin aus silybum marianum

1985
- 1985-10-23 DE DE19853537656 patent/DE3537656A1/de active Granted
- 1985-11-11 GB GB08527809A patent/GB2167746B/en not_active Expired
- 1985-11-12 CH CH4854/85A patent/CH660008A5/de not_active IP Right Cessation
- 1985-11-13 LU LU86164A patent/LU86164A1/de unknown
- 1985-11-14 NL NL8503136A patent/NL192204C/nl not_active IP Right Cessation
- 1985-11-18 FI FI854536A patent/FI84065C/fi not_active IP Right Cessation
- 1985-11-19 AT AT0337285A patent/AT391315B/de not_active IP Right Cessation
- 1985-11-20 YU YU1812/85A patent/YU43690B/xx unknown
- 1985-11-20 CS CS858379A patent/CS271321B2/cs unknown
- 1985-11-20 CA CA000495805A patent/CA1337125C/en not_active Expired - Fee Related
- 1985-11-20 SE SE8505488A patent/SE457957B/sv not_active IP Right Cessation
- 1985-11-21 EG EG741/85A patent/EG17710A/xx active
- 1985-11-21 PT PT81531A patent/PT81531B/pt not_active IP Right Cessation
- 1985-11-21 IT IT8522933A patent/IT1207508B/it active
- 1985-11-21 IE IE292785A patent/IE59209B1/en not_active IP Right Cessation
- 1985-11-21 DK DK537685A patent/DK166541B1/da not_active IP Right Cessation
- 1985-11-21 NO NO854657A patent/NO160206C/no unknown
- 1985-11-21 HU HU854449A patent/HU195504B/hu not_active IP Right Cessation
- 1985-11-21 ES ES549119A patent/ES8609312A1/es not_active Expired
- 1985-11-21 PL PL1985256373A patent/PL146889B1/pl unknown
- 1985-11-22 AR AR85302358A patent/AR241268A1/es active
- 1985-11-22 MX MX009231A patent/MX172175B/es unknown
- 1985-11-22 BE BE2/60851A patent/BE903694A/fr not_active IP Right Cessation
- 1985-11-22 FR FR8517320A patent/FR2573426B1/fr not_active Expired
1986
- 1986-04-16 ES ES554022A patent/ES8704482A1/es not_active Expired
1988
- 1988-03-18 US US07/171,176 patent/US4871763A/en not_active Expired - Fee Related
1991
- 1991-01-29 JP JP3009169A patent/JPH0678228B2/ja not_active Expired - Lifetime
- 1991-11-20 DK DK189491A patent/DK164866C/da not_active IP Right Cessation
1992
- 1992-09-17 DK DK199201145A patent/DK172879B1/da active

Also Published As

Publication number	Publication date
ATA337285A (de)	1990-03-15
IE59209B1 (en)	1994-01-26
DK537685A (da)	1986-05-23
LU86164A1 (de)	1986-03-24
JPH05271071A (ja)	1993-10-19
FI84065B (fi)	1991-06-28
IT8522933A0 (it)	1985-11-21
DK114592A (da)	1992-09-17
PL256373A1 (en)	1986-12-02
PT81531B (pt)	1987-11-11
CA1337125C (en)	1995-09-26
FR2573426A1 (fr)	1986-05-23
CH660008A5 (de)	1987-03-13
FI854536A0 (fi)	1985-11-18
SE457957B (sv)	1989-02-13
AR241268A1 (es)	1992-04-30
US4871763A (en)	1989-10-03
DE3537656A1 (de)	1986-05-22
JPH0678228B2 (ja)	1994-10-05
IT1207508B (it)	1989-05-25
SE8505488D0 (sv)	1985-11-20
DK189491A (da)	1991-11-20
MX172175B (es)	1993-12-07
YU43690B (en)	1989-10-31
DK114592D0 (da)	1992-09-17
ES554022A0 (es)	1987-04-01
NO160206C (no)	1989-03-22
BE903694A (fr)	1986-05-22
YU181285A (en)	1987-12-31
FI84065C (fi)	1991-10-10
NL8503136A (nl)	1986-06-16
DK537685D0 (da)	1985-11-21
DK166541B1 (da)	1993-06-07
DK164866C (da)	1993-01-18
NL192204B (nl)	1996-11-01
AT391315B (de)	1990-09-25
GB8527809D0 (en)	1985-12-18
ES8609312A1 (es)	1986-09-01
PT81531A (de)	1985-12-01
CS271321B2 (en)	1990-09-12
NO160206B (no)	1988-12-12
CS837985A2 (en)	1990-02-12
FI854536A (fi)	1986-05-23
HUT40115A (en)	1986-11-28
SE8505488L (sv)	1986-05-23
DE3537656C2 (xx)	1989-03-16
GB2167746A (en)	1986-06-04
DK164866B (da)	1992-08-31
FR2573426B1 (fr)	1988-06-10
NO854657L (no)	1986-05-23
HU195504B (en)	1988-05-30
ES8704482A1 (es)	1987-04-01
EG17710A (en)	1990-10-30
IE852927L (en)	1986-05-22
DK172879B1 (da)	1999-09-06
DK189491D0 (da)	1991-11-20
PL146889B1 (en)	1989-03-31
GB2167746B (en)	1989-01-11
ES549119A0 (es)	1986-09-01

Publication	Publication Date	Title
NL192204C (nl)	1997-03-04	Werkwijze voor het bereiden van isosilybine-vrij silibinine en farmaceutisch preparaat dat isosilybine-vrij silibinine bevat.
JPS6277390A (ja)	1987-04-09	プロアントシアニジンａ２の製法、医薬組成物およびそれらの治療用途
JPH06507601A (ja)	1994-09-01	セスキテルペンラクトンの抽出方法
JP3075358B2 (ja)	2000-08-14	肝機能改善剤
JPS61143377A (ja)	1986-07-01	シリビニン誘導体、その製法及びこれを含有する火傷、肝臓障害及びキノコ毒の治療剤
KR930003073B1 (ko)	1993-04-17	이소실리빈이 없는 실리비닌의 제조방법
US3873699A (en)	1975-03-25	Pharmacologically active substances isolated from {8 cadia ellisiana {b
JPH0339506B2 (xx)	1991-06-14
US2727891A (en)	1955-12-20	Vegetable
JPS60193996A (ja)	1985-10-02	側柏葉から止血活性物質を抽出する方法、及びそれを含有する止血剤
FI85855B (fi)	1992-02-28	Foerfarande foer framstaellning av isosilybinfri silibin och silibin innehaollande laekemedel.
JPH0212932B2 (xx)	1990-03-30
KR20030064921A (ko)	2003-08-06	혈당강하 및 진통제 조성물
KR20020007302A (ko)	2002-01-26	신규 짐넴산 유도체, 그 제조 방법, 및 그의 약학적 용도
JPS6153330B2 (xx)	1986-11-17
JPS62240621A (ja)	1987-10-21	止血剤
JPS6153333B2 (xx)	1986-11-17
JPS62116521A (ja)	1987-05-28	抗菌剤
NO160207B (no)	1988-12-12	Fremgangsmaate ved fremstilling av isosilybininfritt silibinin.
JPH0859482A (ja)	1996-03-05	アルコール吸収抑制剤
JPS6341889B2 (xx)	1988-08-19
JPS6153329B2 (xx)	1986-11-17
JPH05246869A (ja)	1993-09-24	虚血性疾患改善治療剤

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Date	Code	Title	Description
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1990-08-01	BC	A request for examination has been filed
1990-08-16	CNR	Transfer of rights (patent application after its laying open for public inspection)	Free format text: MADAUS AKTIENGESELLSCHAFT
2002-08-01	V1	Lapsed because of non-payment of the annual fee	Effective date: 20020601