ZA907134B - 4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives,salts and esters,process for their preparation,their use as pharmaceuticals,and pharmaceutical preparations and precursors - Google Patents
4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives,salts and esters,process for their preparation,their use as pharmaceuticals,and pharmaceutical preparations and precursorsInfo
- Publication number
- ZA907134B ZA907134B ZA907134A ZA907134A ZA907134B ZA 907134 B ZA907134 B ZA 907134B ZA 907134 A ZA907134 A ZA 907134A ZA 907134 A ZA907134 A ZA 907134A ZA 907134 B ZA907134 B ZA 907134B
- Authority
- ZA
- South Africa
- Prior art keywords
- preparation
- pharmaceutical preparations
- esters
- salts
- hydroxytetrahydropyran
- Prior art date
Links
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical class OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- WMHRYMDGHQIARA-UHFFFAOYSA-N 4-hydroxyoxan-2-one Chemical class OC1CCOC(=O)C1 WMHRYMDGHQIARA-UHFFFAOYSA-N 0.000 title 1
- 239000002243 precursor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229940079593 drug Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/10—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/04—Preparation of quinones by oxidation giving rise to quinoid structures of unsubstituted ring carbon atoms in six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/24—Quinones containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3929913A DE3929913A1 (de) | 1989-09-08 | 1989-09-08 | 4-hydroxytetrahydropyran-2-one sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate sowie vorprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA907134B true ZA907134B (en) | 1991-06-26 |
Family
ID=6388931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA907134A ZA907134B (en) | 1989-09-08 | 1990-09-07 | 4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives,salts and esters,process for their preparation,their use as pharmaceuticals,and pharmaceutical preparations and precursors |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5294724A (hu) |
| EP (1) | EP0418648B1 (hu) |
| JP (1) | JP3053417B2 (hu) |
| KR (1) | KR0162081B1 (hu) |
| AT (1) | ATE116979T1 (hu) |
| AU (1) | AU629977B2 (hu) |
| CA (1) | CA2024849C (hu) |
| DE (2) | DE3929913A1 (hu) |
| DK (1) | DK0418648T3 (hu) |
| ES (1) | ES2067609T3 (hu) |
| FI (1) | FI108642B (hu) |
| GR (1) | GR3015360T3 (hu) |
| HU (1) | HU212103B (hu) |
| IE (1) | IE66106B1 (hu) |
| IL (1) | IL95599A (hu) |
| NO (1) | NO175002C (hu) |
| NZ (1) | NZ235194A (hu) |
| PT (1) | PT95237B (hu) |
| ZA (1) | ZA907134B (hu) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL90249A (en) * | 1988-05-13 | 1994-01-25 | Hoechst Ag | Hydroxytethrahydropyran-2-ones, the corresponding dihydroxycarboxylic acid derivatives and salts, process of preparation and pharmaceutical compositions containing them |
| US5248793A (en) * | 1990-10-17 | 1993-09-28 | Warner-Lambert Company | Process for the synthesis of (4R-cis)-1,1-dimethylethyl 6-iodomethyl or 6-(phenyl-substituted)sulfonyloxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate |
| US5103024A (en) * | 1990-10-17 | 1992-04-07 | Warner-Lambert Company | Process for the synthesis of (4r-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate |
| DE4312034A1 (de) * | 1993-04-13 | 1994-10-20 | Hesch Rolf Dieter Prof Dr Med | Neuartige Androgene und Anabolika |
| IL129871A (en) * | 1994-05-06 | 2003-11-23 | Pharmacia & Upjohn Inc | Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections |
| IL113567A0 (en) * | 1994-05-06 | 1995-08-31 | Upjohn Co | Compounds useful to treat retroviral infections |
| US5925672A (en) * | 1996-12-06 | 1999-07-20 | Neurosciences Research Foundation, Inc. | Methods of treating mental diseases, inflammation and pain |
| US6670398B2 (en) * | 1997-05-14 | 2003-12-30 | Atherogenics, Inc. | Compounds and methods for treating transplant rejection |
| EP1464639B1 (en) * | 1997-05-14 | 2007-03-07 | Atherogenics, Inc. | Succinic acid ester of probucol for the inhibition of the expression of VCAM-1 |
| US6852878B2 (en) * | 1998-05-14 | 2005-02-08 | Atherogenics, Inc. | Thioketals and thioethers for inhibiting the expression of VCAM-1 |
| CZ301985B6 (cs) | 1997-05-14 | 2010-08-25 | Atherogenics, Inc. | Lécivo pro lécení kardiovaskulárního onemocnení na bázi monoesteru probukolu s jantarovou kyselinou |
| KR20010020611A (ko) | 1997-07-01 | 2001-03-15 | 아테로제닉스, 인코포레이티드 | 항산화제에 의한 과증식질병 치료의 향상 |
| US6083497A (en) | 1997-11-05 | 2000-07-04 | Geltex Pharmaceuticals, Inc. | Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers |
| WO1999063994A1 (en) | 1998-06-08 | 1999-12-16 | Advanced Medicine, Inc. | MULTIBINDING INHIBITORS OF HMG-CoA REDUCTASE |
| AU2001247651B2 (en) * | 2000-03-21 | 2007-01-04 | Atherogenics, Inc | Thioketals and thioethers for inhibiting the expression of vcam-1 |
| CA2404044A1 (en) | 2000-04-11 | 2001-10-18 | Atherogenics, Inc. | Compounds and methods to increase plasma hdl cholesterol levels and improve hdl functionality |
| NL1015744C2 (nl) * | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| AU2002320025A1 (en) * | 2001-04-11 | 2002-11-11 | Atherogenics, Inc. | Probucol monoesters and their use to increase plasma hdl cholesterol levels and improve hdl functionality |
| US7273948B2 (en) | 2003-01-13 | 2007-09-25 | Atherogenics, Inc. | Process of preparing esters and ethers of probucol and derivatives thereof |
| US20050113445A1 (en) * | 2003-02-20 | 2005-05-26 | Daniele Piomelli | Methods of treating mental diseases, inflammation and pain |
| US20070260087A1 (en) | 2004-04-20 | 2007-11-08 | Atherogenics, Inc. | Process of Preparing Esters and Ethers of Probucol and Derivatives Thereof |
| US20060194981A1 (en) * | 2005-02-26 | 2006-08-31 | Jass Paul A | Process for preparation of probucol derivatives |
| WO2008118948A1 (en) | 2007-03-26 | 2008-10-02 | Atherogenics, Inc. | Methods and compositions of derivatives of probucol for the treatment of diabetes |
| US20080280985A1 (en) * | 2007-03-27 | 2008-11-13 | Scott Robert A D | Methods and Compositions Using Certain Phenolic Derivatives for the Treatment of Diabetes |
| US20210008084A1 (en) | 2017-10-16 | 2021-01-14 | Tsinghua University | Mevalonate pathway inhibitor and pharmaceutical composition thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077805A (en) | 1974-10-25 | 1978-03-07 | Shirow Asakawa | Light-sensitive composition containing antioxidant |
| EP0216127B1 (de) * | 1985-08-29 | 1990-09-26 | Hoechst Aktiengesellschaft | 6-Phenoxymethyl-4-hydroxytetrahydropyran-2-one, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel, pharmazeutische Präparate und Zwischenprodukte |
| DE3632893A1 (de) * | 1986-09-27 | 1988-04-07 | Hoechst Ag | 4-(r)-hydroxy-6(s)-arylthiomethyl-tetrahydropyran-2-one, deren entsprechende sulfoxide und sulfone, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte |
| US4789682A (en) * | 1987-03-17 | 1988-12-06 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| DE3722809A1 (de) * | 1987-07-10 | 1989-01-19 | Hoechst Ag | 3-desmethyl-4-fluor-mevalonsaeurederivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen, ihre verwendung und zwischenprodukte |
| IT1217402B (it) * | 1988-04-12 | 1990-03-22 | Donegani Guido Ist | Procedimento per la preparazione di difenoli monoesteri sostituiti con gruppi arilici e prodotti cosi' ottenuti |
| DE3819999A1 (de) * | 1988-06-11 | 1989-12-21 | Hoechst Ag | Neue 6-phenoxymethyl-4-hydroxytetrahydropyran-2-one und 6-thiphenoxymethyl-4-hydroxytetrahydropyran-2 -one, sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zur herstellung dieser verbindung, ihre verwendung als arzneimittel, pharmazeutische praeparate und neue phenole sowie thiophenole |
| IL90249A (en) * | 1988-05-13 | 1994-01-25 | Hoechst Ag | Hydroxytethrahydropyran-2-ones, the corresponding dihydroxycarboxylic acid derivatives and salts, process of preparation and pharmaceutical compositions containing them |
| US5093363A (en) * | 1989-08-22 | 1992-03-03 | Shionogi & Co., Ltd. | 2,4,6-substituted phenol derivatives |
-
1989
- 1989-09-08 DE DE3929913A patent/DE3929913A1/de not_active Withdrawn
-
1990
- 1990-09-05 AT AT90117043T patent/ATE116979T1/de not_active IP Right Cessation
- 1990-09-05 EP EP90117043A patent/EP0418648B1/de not_active Expired - Lifetime
- 1990-09-05 ES ES90117043T patent/ES2067609T3/es not_active Expired - Lifetime
- 1990-09-05 DE DE59008238T patent/DE59008238D1/de not_active Expired - Lifetime
- 1990-09-05 DK DK90117043.1T patent/DK0418648T3/da active
- 1990-09-06 US US07/578,240 patent/US5294724A/en not_active Expired - Lifetime
- 1990-09-06 FI FI904395A patent/FI108642B/fi active IP Right Grant
- 1990-09-06 NZ NZ235194A patent/NZ235194A/en unknown
- 1990-09-06 IL IL9559990A patent/IL95599A/en active IP Right Grant
- 1990-09-07 JP JP2235998A patent/JP3053417B2/ja not_active Expired - Lifetime
- 1990-09-07 ZA ZA907134A patent/ZA907134B/xx unknown
- 1990-09-07 HU HU905827A patent/HU212103B/hu unknown
- 1990-09-07 NO NO903911A patent/NO175002C/no not_active IP Right Cessation
- 1990-09-07 AU AU62277/90A patent/AU629977B2/en not_active Expired
- 1990-09-07 CA CA002024849A patent/CA2024849C/en not_active Expired - Lifetime
- 1990-09-07 PT PT95237A patent/PT95237B/pt not_active IP Right Cessation
- 1990-09-07 KR KR1019900014100A patent/KR0162081B1/ko not_active Expired - Lifetime
- 1990-09-07 IE IE326290A patent/IE66106B1/en not_active IP Right Cessation
-
1995
- 1995-03-10 GR GR950400518T patent/GR3015360T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2067609T3 (es) | 1995-04-01 |
| HU905827D0 (en) | 1991-03-28 |
| NZ235194A (en) | 1992-06-25 |
| NO175002C (no) | 1994-08-17 |
| NO903911L (no) | 1991-03-11 |
| ATE116979T1 (de) | 1995-01-15 |
| KR0162081B1 (ko) | 1998-12-01 |
| IE66106B1 (en) | 1995-12-13 |
| PT95237B (pt) | 1997-06-30 |
| AU629977B2 (en) | 1992-10-15 |
| IL95599A (en) | 1999-07-14 |
| IE903262A1 (en) | 1991-03-13 |
| EP0418648A1 (de) | 1991-03-27 |
| NO175002B (no) | 1994-05-09 |
| HU212103B (en) | 1996-02-28 |
| JP3053417B2 (ja) | 2000-06-19 |
| IL95599A0 (en) | 1991-06-30 |
| FI904395A0 (fi) | 1990-09-06 |
| GR3015360T3 (en) | 1995-06-30 |
| DE59008238D1 (de) | 1995-02-23 |
| FI108642B (fi) | 2002-02-28 |
| CA2024849C (en) | 2002-01-01 |
| HUT56085A (en) | 1991-07-29 |
| KR910006263A (ko) | 1991-04-29 |
| CA2024849A1 (en) | 1991-03-09 |
| DE3929913A1 (de) | 1991-04-04 |
| PT95237A (pt) | 1991-05-22 |
| US5294724A (en) | 1994-03-15 |
| NO903911D0 (no) | 1990-09-07 |
| DK0418648T3 (da) | 1995-06-12 |
| AU6227790A (en) | 1991-03-14 |
| JPH0399075A (ja) | 1991-04-24 |
| EP0418648B1 (de) | 1995-01-11 |
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