PL146890B1 - Process for preparing novel derivatives of silibinin - Google Patents

Process for preparing novel derivatives of silibinin Download PDF

Info

Publication number: PL146890B1
Authority: PL; Poland
Prior art keywords: formula; silibinin; alk; animals; sili
Prior art date: 1984-11-22

Application number

PL1985256374A

Other languages

English (en)

Polish (pl)

Other versions

PL256374A1 (en

Inventor

Reinhard Braatz

Klaus Goerler

Guenter Halbach

Hartwig Soicke

Karlheinz Schmidt

Original Assignee

Madaus & Co Dr

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

1985-11-21

Publication date

1989-03-31

1985-11-21 Application filed by Madaus & Co Dr filed Critical Madaus & Co Dr

1986-12-02 Publication of PL256374A1 publication Critical patent/PL256374A1/xx

1989-03-31 Publication of PL146890B1 publication Critical patent/PL146890B1/pl

Links

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
229920006395 saturated elastomer Polymers 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
238000005406 washing Methods 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
239000008240 homogeneous mixture Substances 0.000 claims description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
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
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
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 description 18
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 15
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150000004665 fatty acids Chemical class 0.000 description 10
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
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KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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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 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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 description 3
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YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
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239000011886 peripheral blood Substances 0.000 description 3
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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239000001384 succinic acid Substances 0.000 description 3
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JVJFIQYAHPMBBX-UHFFFAOYSA-N 4-hydroxynonenal Chemical compound CCCCCC(O)C=CC=O JVJFIQYAHPMBBX-UHFFFAOYSA-N 0.000 description 2
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108091003079 Bovine Serum Albumin Proteins 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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102000004190 Enzymes Human genes 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241000320380 Silybum Species 0.000 description 2
235000010841 Silybum marianum Nutrition 0.000 description 2
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235000012333 Vitis X labruscana Nutrition 0.000 description 2
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WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
-1 alkylene dicarboxylic acids Chemical class 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
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239000008280 blood Substances 0.000 description 2
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239000012894 fetal calf serum Substances 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
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125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
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OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
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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)

PL1985256374A 1984-11-22 1985-11-21 Process for preparing novel derivatives of silibinin PL146890B1 (en)

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 (fi)
KR (1)	KR870001020B1 (fi)
AR (1)	AR240931A1 (fi)
AT (1)	AT393268B (fi)
BE (1)	BE903693A (fi)
CA (1)	CA1337124C (fi)
CH (1)	CH659473A5 (fi)
CS (1)	CS273610B2 (fi)
DD (1)	DD259191A1 (fi)
DE (1)	DE3442639A1 (fi)
DK (1)	DK164865C (fi)
EG (1)	EG19424A (fi)
ES (1)	ES8609311A1 (fi)
FI (1)	FI84064C (fi)
FR (1)	FR2573427B1 (fi)
GB (1)	GB2167414B (fi)
HU (1)	HU195503B (fi)
IE (1)	IE58791B1 (fi)
IT (1)	IT1190426B (fi)
LU (1)	LU86163A1 (fi)
MX (1)	MX168415B (fi)
NL (1)	NL192387C (fi)
NO (1)	NO160205C (fi)
PL (1)	PL146890B1 (fi)
PT (1)	PT81532B (fi)
SE (1)	SE465676B (fi)
SU (1)	SU1436875A3 (fi)
YU (1)	YU43689B (fi)
ZA (1)	ZA858951B (fi)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
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
CA2601028C (en) *	2005-03-11	2014-05-27	Howard Florey Institute Of Experimental Physiology And Medecine	Flavonoid compounds and uses thereof
RU2482844C2 (ru) *	2007-11-15	2013-05-27	Мадаус Гмбх	Силибининовый компонент для лечения гепатита
EP2392326B9 (en) *	2007-11-15	2018-09-05	Madaus GmbH	Silibinin component for the treatment of hepatitis
WO2010130460A1 (en) *	2009-05-14	2010-11-18	Euromed S.A.	Amorphous silibinin for the treatment of viral hepatitis
AU2013286721B2 (en)	2012-07-05	2018-04-26	Nutramax Laboratories, Inc.	Compositions comprising a sulforaphane or a sulforaphane precursor and milk thistle extract or powder
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
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

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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 YU YU1786/85A patent/YU43689B/xx unknown
- 1985-11-14 AR AR302267A patent/AR240931A1/es active
- 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 DD DD85283042A patent/DD259191A1/de not_active IP Right Cessation
- 1985-11-20 CA CA000495804A patent/CA1337124C/en not_active Expired - Fee Related
- 1985-11-20 SE SE8505487A patent/SE465676B/sv not_active IP Right Cessation
- 1985-11-20 CS CS837885A patent/CS273610B2/cs unknown
- 1985-11-21 PT PT81532A patent/PT81532B/pt not_active IP Right Cessation
- 1985-11-21 ES ES549116A patent/ES8609311A1/es not_active Expired
- 1985-11-21 ZA ZA858951A patent/ZA858951B/xx unknown
- 1985-11-21 EG EG74085A patent/EG19424A/xx active
- 1985-11-21 IT IT22932/85A patent/IT1190426B/it active
- 1985-11-21 HU HU854448A patent/HU195503B/hu not_active IP Right Cessation
- 1985-11-21 DK DK537785A patent/DK164865C/da not_active IP Right Cessation
- 1985-11-21 SU SU853985401A patent/SU1436875A3/ru active
- 1985-11-21 PL PL1985256374A patent/PL146890B1/pl unknown
- 1985-11-21 NO NO854655A patent/NO160205C/no not_active IP Right Cessation
- 1985-11-22 KR KR1019850008733A patent/KR870001020B1/ko not_active IP Right Cessation
- 1985-11-22 MX MX009022A patent/MX168415B/es unknown
- 1985-11-22 BE BE2/60850A patent/BE903693A/fr not_active IP Right Cessation
- 1985-11-22 FR FR858517321A patent/FR2573427B1/fr not_active Expired
- 1985-11-22 JP JP60261629A patent/JPS61143377A/ja active Granted

Also Published As

Publication number	Publication date
IE58791B1 (en)	1993-11-17
FI84064B (fi)	1991-06-28
FR2573427A1 (fr)	1986-05-23
BE903693A (fr)	1986-05-22
PT81532A (de)	1985-12-01
NO160205C (no)	1989-03-22
SE8505487L (sv)	1986-05-23
CS273610B2 (en)	1991-03-12
NO160205B (no)	1988-12-12
YU178685A (en)	1988-02-29
SE8505487D0 (sv)	1985-11-20
DE3442639A1 (de)	1986-05-22
HU195503B (en)	1988-05-30
SE465676B (sv)	1991-10-14
LU86163A1 (de)	1986-03-24
YU43689B (en)	1989-10-31
NL192387C (nl)	1997-07-04
EG19424A (en)	1995-02-28
MX168415B (es)	1993-05-24
ES549116A0 (es)	1986-09-01
KR860004056A (ko)	1986-06-16
NL192387B (nl)	1997-03-03
AR240931A2 (es)	1991-03-27
PL256374A1 (en)	1986-12-02
ZA858951B (en)	1986-08-27
IE852808L (en)	1986-05-22
PT81532B (pt)	1987-11-11
GB2167414A (en)	1986-05-29
IT1190426B (it)	1988-02-16
JPS61143377A (ja)	1986-07-01
AR240931A1 (es)	1991-03-27
DK537785D0 (da)	1985-11-21
KR870001020B1 (ko)	1987-05-23
DK537785A (da)	1986-05-23
FI854535A0 (fi)	1985-11-18
CA1337124C (en)	1995-09-26
IT8522932A0 (it)	1985-11-21
JPH0432073B2 (fi)	1992-05-28
DE3442639C2 (fi)	1989-08-10
AT393268B (de)	1991-09-25
SU1436875A3 (ru)	1988-11-07
CS837885A2 (en)	1990-08-14
FI854535A (fi)	1986-05-23
NO854655L (no)	1986-05-23
DD259191A1 (de)	1988-08-17
HUT40114A (en)	1986-11-28
FI84064C (fi)	1991-10-10
NL8503171A (nl)	1986-06-16
DK164865C (da)	1993-01-18
ES8609311A1 (es)	1986-09-01
GB8528226D0 (en)	1985-12-18
DK164865B (da)	1992-08-31
FR2573427B1 (fr)	1989-03-10
ATA337185A (de)	1991-02-15
CH659473A5 (de)	1987-01-30
GB2167414B (en)	1989-01-11

Publication	Publication Date	Title
PL146890B1 (en)	1989-03-31	Process for preparing novel derivatives of silibinin
KR0134376B1 (ko)	1998-04-21	면역 억제제로서 유용한 4-퀴놀린 카르복실산 유도체
CA2372223A1 (en)	2000-11-09	Use of phyllanthus for targeted stimulation of the immune system
FI84065B (fi)	1991-06-28	Foerfarande foer framstaellning av isosilybinfri silibinin.
RU2383537C2 (ru)	2010-03-10	Применение тризамещенных бензопиранонов
KR20000002041A (ko)	2000-01-15	항염증 활성이 있는 길경 추출물
JPH023800B2 (fi)	1990-01-24
IE50062B1 (en)	1986-02-05	Pharmaceutical compositions containing climbing ivy extracts
JPH09262066A (ja)	1997-10-07	高脂血症を抑制するための食品および医薬組成物
SI8511786A8 (sl)	1996-06-30	Postopek za pripravo derivatov silibinina
IL34407A (en)	1973-08-29	Bis(2-carboxychromonyl)compounds,their preparation and pharmaceutical compositions containing them
KR100213897B1 (ko)	1999-08-02	신생혈관유도현상 억제 활성을 갖는 계피 유래의 신남 알데하이드 유도체, 이의 제조방법 및 이를 함유하는 조성물
KR100542323B1 (ko)	2006-01-11	후박나무로부터 세포사멸 유도작용을 갖는 화합물을 분리하는 방법
US3947479A (en)	1976-03-30	Reduction of serum lipid levels, and agents and compositions useful therefor
EP0619817B1 (en)	1999-03-17	Novel pharmaceutically active flavilium compounds
KR0137422B1 (ko)	1998-06-01	아랄로사이드 a를 유효 성분으로 하는 위장 질환 치료제
US4001407A (en)	1977-01-04	Reduction of serum lipid levels and agents and compositions useful therefor
WO1993012079A1 (en)	1993-06-24	Novel phenylsulfonylacrylate ester derivatives
JPH03157347A (ja)	1991-07-05	オクタデセン酸誘導体及びこれを有効成分とする子宮頚癌細胞の殺細胞剤
JPH0517887B2 (fi)	1993-03-10
CS221523B2 (en)	1983-04-29	Method of making the derivative of the 1,4-dioxanaphtalene
MXPA00007136A (en)	2002-03-26	Sea cucumber carotenoid lipid fraction products and methods of use
MXPA01006405A (en)	2001-12-13	Antiprotozoal saponins