DE3318989A1 - Ss,(gamma)-dihydropolyprenylalkoholderivate und arzneimittel, welche diese enthalten - Google Patents
Ss,(gamma)-dihydropolyprenylalkoholderivate und arzneimittel, welche diese enthaltenInfo
- Publication number
- DE3318989A1 DE3318989A1 DE19833318989 DE3318989A DE3318989A1 DE 3318989 A1 DE3318989 A1 DE 3318989A1 DE 19833318989 DE19833318989 DE 19833318989 DE 3318989 A DE3318989 A DE 3318989A DE 3318989 A1 DE3318989 A1 DE 3318989A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- ing
- dipl
- integer
- active ingredient
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
-
- 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
- A61K31/765—Polymers containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmacology & Pharmacy (AREA)
- Mycology (AREA)
- Food Science & Technology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
H-(CH9-C=CH-CH0-) CH9-CH CH-COOH (V)
5
5
H-(CH0-C=CH-CH0-) CH0-CH CH-COOR (IV)
30
~ 6-Methylheptan-2-on
COOC2H5
ii) Decarboxylierung
20
Berechnet %: | C | 82 | ,46 | H | 11 | ,60 |
Gefunden %: | 82 | ,45 | 11 | ,60 |
15
Berechnet %: | C | 84 | ,37 | H | 10 | ,85 |
Gefunden %: | 84 | ,38 | 10 | ,83 |
Geprüfte Verbindung |
A | Dosierung | mg/kg | Überlebensrate nach 1 Woche; Anzahl der über lebenden/Anzahl der Ver suchstiere |
·* 60 (%) |
Verbindung | B | 100 | mg/kg | 6/10 | -> 60 (%) |
Verbindung | C | 1Θ0 | mg/kg | 6/10 | ■» 70 (%) |
Verbindung | D | 100 | mg/kg | 7/10 | ■> 60 {%) |
Verbindung | E | 100 | mg/kg | 6/10 | -» 90 (%) |
Verbindung | 50 | mg/kg | 9/10 | ·» 100 (%) | |
F | 100 | mg/kg | 10/10 | * 30 (%) | |
Verbindung | G | 100 | mg/kg | 3/10 | * 100 (%) |
Verbindung | H | 100 | mg/kg | 10/10 | ■» 70 (%) |
Verbindung | I | 100 | mg/kg | 7/10 | ·» 90 (%) |
Verbindung | J | 100 | mg/kg . | 9/10 | ± 60 (%) |
Verbindung | 50 | mg/kg | 6/10 | ■» 100 (%) | |
K | 100 | mg/kg | 10/10 | ■*■ 50 (%) | |
Verbindung | 50 | mg/kg | 5/10 | ·* 90 (%) | |
100 | 9/10 | - 1,25 (%) | |||
Blindprobe (nicht be handelt) |
Kontrollver bindung (MDP) |
mg/kg | 1/80 | - 40 (%) | |
3,5 | 4/10 |
Geprüfte Verbindung |
Anzahl der Tiere |
Halbwerts zeit (min:sek) |
Veränderung der Phagocy tosis (%) |
Blindprobe (nicht be handelt) |
48 | 8:01 | 100 |
Verbindung A | 4 | 5:34 | 70 |
Verbindung D | 4 | 5:30 | 69 |
Verbindung E | 4 | 5:18 | 66 |
Verbindung G | 3 | 6:43 | 84 |
Verbindung I | 4 | 5:20 | 67 |
Verbindung J | 4 | 5:15 | 65 |
Verbindung K | 4 | 3:25 | 43 |
Geprüfte Verbindung |
L | Dosis | mg | Uberlebensrate nach 1 Woche; Anzahl der Überlebenden/An zahl der Versuchstiere |
-> 40 (%) |
Verbindung | 50 | mg | 4/10 | -^ 90 (%) | |
M | 100 | mg | 9/10 | -► 80 (%) | |
Verbindung | N | 100 | mg | 8/10 | -» 40 (%) |
Verbindung | 0 | 100 | mg | 4/10 | -» 40 (%) |
Verbindung | P | 100 | mg | 4/10 | ■* 80 (%) |
Verbindung | Q | 100 | mg | 8/10 | -*■ 100 (%) |
Verbindung | R | 100 | mg | 10/10 | ■* 30 (%) |
Verbindung | 100 | 3/10 | -* 1,25 (%) | ||
Blindprobe (unbehan- delt) |
Kontrollver bindung MDP |
mg | 1/80 | -> 40 (%) | |
3,5 | 4/10 |
Geprüfte Verbindung |
Anzahl der Tiere |
Halbwerts zeit {min:sek) |
Veränderung der Phagocy tosis (%) |
Blindprobe (unbehan- delt) Verbindung L Verbindung M |
48 4 4 |
8:01 6:00 7:00 |
100 75 87 |
Geprüfte Verbindung |
Dosis | Überlebensrate nach 1 Woche; Anzahl der über lebenden/Anzahl der Ver suchstiere |
Verbindung S | 100 mg/kg | 10/10 ■» 100 (%) |
Verbindung T | 100 mg/kg | 10/10 ■» 100 (%) |
Verbindung U | 100 mg/kg | 3/10 -» 30 (%) |
Verbindung V | 100 mg/kg | 10/10 -> 100 (%) |
Blindprobe (unbehan- delt) |
1/80 -> 1,25 (%) | |
Kontrollver bindung MDP |
3,5 mg/kg | 4/10 ■» 40 (%) |
Geprüfte Verbindung |
Anzahl der Tiere |
Halbwerts zeit (min:sek) |
Veränderung der Phagocy tosis (%) |
Blindprobe (unbehan- delt) |
48 | 8:01 | 100 |
Verbindung T | 3 | 7:41 | 96 |
Verbindung V | 4 | 5:48 | 72 |
5
5 | g |
80 | g |
20 | g |
22 | g |
3 | g |
gesamt 130 g
5 | 0 | g | |
1 | 0 | 0 | g |
20 | 5 | g | |
1 | 0 | g | |
4 | g | ||
g | |||
1 |
Polyvinylpyrrolidon
Talkum
gesamt 100 g
Zuberextungsbeispiel 5 (Kapseln) | 5 g | |
25 | 80 g | |
Wirkstoff | 20 g | |
mikrokristalline Zellulose | 22 g | |
Maisstärke | 3 cf | |
Laktose- | 130 g | |
30 | Polyvinylpyrrolidon | |
gesamt | ||
Zubereitungsbexspiel 7 (Tabletten) | 5 g |
Wirkstoff | 10 g |
Maisstärke | 20 g |
Laktose | 10 g |
Kalziumcarboxymethylzellulose | 40 g |
mikrokristalline Zellulose | 5 g |
Polyvinylpyrrolidon | 10 g |
Talkum | 100 g |
gesamt | |
37 | g |
2 | g |
9 | g |
40 | g |
100 | ml |
1.000 | ml |
Phosphorsäurepuffer (0,1M, pH 6,0)
5 | g |
10 | g |
20 | g |
10 | g |
40 | g |
5 | g |
10 | g |
Wirkstoff | , pH | 6,0) | 10 | g |
Nikkol HCO-60 | bis | auf | 37 | g |
Sesamöl | 2 | g | ||
Natriumchlorid | 9 | g | ||
Propylenglykol | 40 | g | ||
Phosphatpuffer (0,1M | 100 | ml | ||
destilliertes Wasser | 1.000 | ml | ||
Claims (2)
20
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3348493A DE3348493C2 (de) | 1982-05-28 | 1983-05-25 | Verwendung von Docosanol zur Behandlung und Prophylaxe von durch Immunmangelerscheinungen verursachten Infektionskrankheiten |
DE3348492A DE3348492C2 (de) | 1982-05-28 | 1983-05-25 | Verwendung eines ß,gamma-Dihydropolyprenylalkoholderivats zur Prophylaxe und Therapie von durch Immunmangelerscheinungen verursachten Infektionskrankheiten |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57089806A JPS58206517A (ja) | 1982-05-28 | 1982-05-28 | 免疫機能不全による疾患の予防・治療剤 |
JP10620382A JPS58225014A (ja) | 1982-06-22 | 1982-06-22 | 免疫機能不全による疾患の予防・治療剤 |
JP18364382A JPS5973533A (ja) | 1982-10-21 | 1982-10-21 | β,γ−ジヒドロポリプレニルアルコ−ル誘導体 |
JP18364282A JPS5973513A (ja) | 1982-10-21 | 1982-10-21 | 免疫機能不全による疾患の予防・治療剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3318989A1 true DE3318989A1 (de) | 1983-12-01 |
DE3318989C2 DE3318989C2 (de) | 1996-11-21 |
Family
ID=27467677
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3318989A Expired - Fee Related DE3318989C2 (de) | 1982-05-28 | 1983-05-25 | ß,gamma-Dihydropolyprenylalkoholderivate und diese enthaltende Arzneimittel und deren Verwendung |
DE3348500A Expired - Fee Related DE3348500C2 (de) | 1982-05-28 | 1983-05-25 | beta,gamma-Dihydropolyprenylalkoholderivat |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3348500A Expired - Fee Related DE3348500C2 (de) | 1982-05-28 | 1983-05-25 | beta,gamma-Dihydropolyprenylalkoholderivat |
Country Status (12)
Country | Link |
---|---|
US (3) | US4624966A (de) |
AT (1) | AT389871B (de) |
CA (1) | CA1310660C (de) |
CH (1) | CH654823A5 (de) |
DE (2) | DE3318989C2 (de) |
DK (1) | DK171640B1 (de) |
ES (3) | ES522789A0 (de) |
FR (5) | FR2527597B1 (de) |
GB (7) | GB2122610B (de) |
IT (1) | IT1164256B (de) |
NL (1) | NL194300C (de) |
SE (4) | SE461650B (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0239729A1 (de) * | 1986-01-23 | 1987-10-07 | Eisai Co., Ltd. | Polyprenylalkohol enthaltende Injektionspräparate und ihre Verwendung |
WO1994020080A1 (en) * | 1993-03-03 | 1994-09-15 | The Government Of The United States Of America, Asrepresented By The Secretary Of The Department Of Health And Human Services | Use of monoterpenes, sesquiterpernes and diterpernes for the treatment of cancer |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3318989C2 (de) * | 1982-05-28 | 1996-11-21 | Eisai Co Ltd | ß,gamma-Dihydropolyprenylalkoholderivate und diese enthaltende Arzneimittel und deren Verwendung |
JPS6112622A (ja) * | 1984-06-29 | 1986-01-21 | Kuraray Co Ltd | 造血幹細胞の分化増殖促進剤 |
US5071879A (en) * | 1989-04-28 | 1991-12-10 | Lidak Pharmaceuticals | Systemic antiviral treatment |
US5070107A (en) * | 1989-04-28 | 1991-12-03 | Lidak Pharmaceuticals | Systemic antiviral treatment |
JP3166991B2 (ja) * | 1992-08-17 | 2001-05-14 | 日清製粉株式会社 | (s)−2,3−ジヒドロポリプレノール化合物を有効成分とする癌増殖抑制および/または癌転移抑制剤 |
DK1473031T3 (da) * | 1993-12-13 | 2008-10-20 | Avanir Pharmaceuticals | Sucroseester - C20 til C28 alkoholformuleringer |
TW338042B (en) * | 1995-10-31 | 1998-08-11 | Clary Kk | Process for producing all trans-form polyprenols |
GB2310138A (en) * | 1996-02-19 | 1997-08-20 | Juris Rubens | Immunomodulating plant polyprenols |
US5952392A (en) * | 1996-09-17 | 1999-09-14 | Avanir Pharmaceuticals | Long-chain alcohols, alkanes, fatty acids and amides in the treatment of burns and viral inhibition |
US6440980B1 (en) * | 1996-09-17 | 2002-08-27 | Avanir Pharmaceuticals | Synergistic inhibition of viral replication by long-chain hydrocarbons and nucleoside analogs |
CN1238687A (zh) * | 1996-12-12 | 1999-12-15 | 法玛西雅厄普约翰美国公司 | 一种二氢聚异戊二烯醇的油剂组合物 |
CA2234326C (en) * | 1997-04-25 | 2001-07-31 | Yoshin Tamai | Process for preparing polyprenols |
US6784207B2 (en) * | 2000-08-04 | 2004-08-31 | Roche Vitamins Inc. | Phytanic acid derivative compositions |
WO2003032915A2 (en) * | 2001-10-16 | 2003-04-24 | Avanir Pharmacueticals | Viral inhibition by n-docosanol |
US7015022B2 (en) * | 2002-06-07 | 2006-03-21 | University Of Medicine & Dentistry Of New Jersey | Mammalian catalase-dependent oxidation processes and methods for stimulating oxidative activities |
US20050158329A1 (en) | 2004-01-21 | 2005-07-21 | Ghosh Swapan K. | Novel phytol derived immunoadjuvants and their use in vaccine formulations |
WO2017087539A1 (en) * | 2015-11-16 | 2017-05-26 | O'neil Gregory W | Alkenone-based formulations for topical applications |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2332009A1 (fr) * | 1975-11-18 | 1977-06-17 | Sankyo Co | Nouveaux derives polyprenyliques, leur procede de preparation et leurs applications |
FR2391723A1 (fr) * | 1977-05-26 | 1978-12-22 | Eisai Co Ltd | Composition therapeutique a base de cetone aliphatique pour le traitement des ulceres peptiques |
FR2399993A1 (fr) * | 1977-08-10 | 1979-03-09 | Eisai Co Ltd | Composition pour le traitement de l'hypertension a base d'un alcool polyprenylique ou d'un de ses esters |
US4186211A (en) | 1973-08-29 | 1980-01-29 | Societe Dite: Institut de Recherches Chimiques et Biologiques Appliquees-I.R.C.E.B.A. | Higher alkanol compositions and the use thereof in treatment of prostate disorders |
EP0041235A2 (de) * | 1980-05-30 | 1981-12-09 | Eisai Co., Ltd. | Alpha, beta-dihydropolyprenylderivate zur Behandlung von Leberkrankheiten |
EP0043738A2 (de) * | 1980-07-09 | 1982-01-13 | THE PROCTER & GAMBLE COMPANY | Topische pharmazeutische Präparate mit Tiefenwirkung |
US4325974A (en) * | 1978-12-01 | 1982-04-20 | Eisai Co., Ltd. | β, γ-Dihydropolyprenyl alcohol and hypotensive pharmaceutical composition containing same |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR4055M (de) * | 1964-01-20 | 1966-04-04 | ||
JPS5391137A (en) * | 1977-01-19 | 1978-08-10 | Sumitomo Chem Co Ltd | Stabilization of agrichemicals |
US4199587A (en) * | 1977-08-10 | 1980-04-22 | Eisai Co., Ltd. | Method of treating hypertension with polyprenyl alcohol ester |
FR2443245A1 (fr) * | 1978-12-07 | 1980-07-04 | Nisshin Flour Milling Co | Nouveaux agents anti-ulcere et compositions pharmaceutiques les contenant |
JPS5791932A (en) * | 1980-11-28 | 1982-06-08 | Kuraray Co Ltd | Polyprenyl compound |
DE3163920D1 (en) * | 1980-12-24 | 1984-07-05 | Eisai Co Ltd | Pharmaceutical preparations comprising polyprenyl compounds, especially as anti-cancer agents, and pharmaceutical compositions for the prevention and treatment of cancer and skin diseases |
JPS57106618A (en) * | 1980-12-24 | 1982-07-02 | Eisai Co Ltd | Anticancer agent consisting of polyprenyl compound |
DE3318989C2 (de) * | 1982-05-28 | 1996-11-21 | Eisai Co Ltd | ß,gamma-Dihydropolyprenylalkoholderivate und diese enthaltende Arzneimittel und deren Verwendung |
DE69325935T2 (de) * | 1992-03-17 | 2000-01-20 | Eisai Co Ltd | Hautbleichendes Mittel enthaltend Teprenone |
-
1983
- 1983-05-25 DE DE3318989A patent/DE3318989C2/de not_active Expired - Fee Related
- 1983-05-25 GB GB08314419A patent/GB2122610B/en not_active Expired
- 1983-05-25 DE DE3348500A patent/DE3348500C2/de not_active Expired - Fee Related
- 1983-05-27 NL NL8301892A patent/NL194300C/nl not_active IP Right Cessation
- 1983-05-27 CA CA000429108A patent/CA1310660C/en not_active Expired - Fee Related
- 1983-05-27 DK DK239483A patent/DK171640B1/da not_active IP Right Cessation
- 1983-05-27 CH CH2902/83A patent/CH654823A5/fr not_active IP Right Cessation
- 1983-05-27 SE SE8303013A patent/SE461650B/sv unknown
- 1983-05-27 ES ES522789A patent/ES522789A0/es active Granted
- 1983-05-30 IT IT21364/83A patent/IT1164256B/it active
- 1983-05-30 FR FR838308941A patent/FR2527597B1/fr not_active Expired
- 1983-05-30 AT AT0197283A patent/AT389871B/de not_active IP Right Cessation
- 1983-10-27 FR FR8317169A patent/FR2532843A1/fr active Pending
- 1983-10-27 FR FR8317170A patent/FR2532848B1/fr not_active Expired
- 1983-10-27 FR FR8317171A patent/FR2532844B1/fr not_active Expired
-
1984
- 1984-02-15 ES ES529754A patent/ES8507444A1/es not_active Expired
- 1984-02-15 ES ES529753A patent/ES529753A0/es active Granted
-
1985
- 1985-03-29 GB GB08508218A patent/GB2159711B/en not_active Expired
- 1985-03-29 GB GB08508219A patent/GB2159712B/en not_active Expired
- 1985-03-29 GB GB08508216A patent/GB2159055B/en not_active Expired
- 1985-03-29 GB GB08508220A patent/GB2159713A/en not_active Withdrawn
- 1985-03-29 GB GB08508214A patent/GB2159054B/en not_active Expired
- 1985-03-29 GB GB08508217A patent/GB2159710B/en not_active Expired
- 1985-07-29 US US06/760,221 patent/US4624966A/en not_active Expired - Lifetime
- 1985-09-02 FR FR858513026A patent/FR2569108B1/fr not_active Expired - Lifetime
-
1988
- 1988-04-22 SE SE8801513A patent/SE502922C2/sv unknown
- 1988-04-22 SE SE8801515A patent/SE502924C2/sv unknown
- 1988-04-22 SE SE8801514A patent/SE502923C2/sv unknown
-
1996
- 1996-01-11 US US08/584,145 patent/US6111131A/en not_active Expired - Fee Related
- 1996-02-14 US US08/601,489 patent/US6288128B1/en not_active Expired - Fee Related
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US4186211A (en) | 1973-08-29 | 1980-01-29 | Societe Dite: Institut de Recherches Chimiques et Biologiques Appliquees-I.R.C.E.B.A. | Higher alkanol compositions and the use thereof in treatment of prostate disorders |
FR2332009A1 (fr) * | 1975-11-18 | 1977-06-17 | Sankyo Co | Nouveaux derives polyprenyliques, leur procede de preparation et leurs applications |
FR2391723A1 (fr) * | 1977-05-26 | 1978-12-22 | Eisai Co Ltd | Composition therapeutique a base de cetone aliphatique pour le traitement des ulceres peptiques |
FR2399993A1 (fr) * | 1977-08-10 | 1979-03-09 | Eisai Co Ltd | Composition pour le traitement de l'hypertension a base d'un alcool polyprenylique ou d'un de ses esters |
US4325974A (en) * | 1978-12-01 | 1982-04-20 | Eisai Co., Ltd. | β, γ-Dihydropolyprenyl alcohol and hypotensive pharmaceutical composition containing same |
EP0041235A2 (de) * | 1980-05-30 | 1981-12-09 | Eisai Co., Ltd. | Alpha, beta-dihydropolyprenylderivate zur Behandlung von Leberkrankheiten |
EP0043738A2 (de) * | 1980-07-09 | 1982-01-13 | THE PROCTER & GAMBLE COMPANY | Topische pharmazeutische Präparate mit Tiefenwirkung |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0239729A1 (de) * | 1986-01-23 | 1987-10-07 | Eisai Co., Ltd. | Polyprenylalkohol enthaltende Injektionspräparate und ihre Verwendung |
WO1994020080A1 (en) * | 1993-03-03 | 1994-09-15 | The Government Of The United States Of America, Asrepresented By The Secretary Of The Department Of Health And Human Services | Use of monoterpenes, sesquiterpernes and diterpernes for the treatment of cancer |
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