PH26257A - Novel 6-phenoxymethyl-4- hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2- ones and the corresponding dihydroxycarboxylic acid derivatives salts and esters processes for the preparation of these compounds their use as pharmaceuticals pharmaceutical preparations and novel phenols and thiophenols - Google Patents
Novel 6-phenoxymethyl-4- hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2- ones and the corresponding dihydroxycarboxylic acid derivatives salts and esters processes for the preparation of these compounds their use as pharmaceuticals pharmaceutical preparations and novel phenols and thiophenols Download PDFInfo
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- PH26257A PH26257A PH38636A PH38636A PH26257A PH 26257 A PH26257 A PH 26257A PH 38636 A PH38636 A PH 38636A PH 38636 A PH38636 A PH 38636A PH 26257 A PH26257 A PH 26257A
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- hydroxytetrahydropyran
- ones
- compounds
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- 150000001875 compounds Chemical class 0.000 title claims description 64
- -1 dihydroxycarboxylic acid derivatives salts Chemical class 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 13
- 150000002148 esters Chemical class 0.000 title claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 8
- 230000008569 process Effects 0.000 title description 7
- 150000002989 phenols Chemical class 0.000 title description 6
- 239000003814 drug Substances 0.000 title description 2
- WWRUMEPVBDVWTM-UHFFFAOYSA-N 4-hydroxy-6-(phenoxymethyl)oxan-2-one Chemical class O1C(=O)CC(O)CC1COC1=CC=CC=C1 WWRUMEPVBDVWTM-UHFFFAOYSA-N 0.000 title 1
- KUWPQLRPLIACDU-UHFFFAOYSA-N 4-hydroxy-6-(phenylsulfanylmethyl)oxan-2-one Chemical class S(C1=CC=CC=C1)CC1CC(CC(O1)=O)O KUWPQLRPLIACDU-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011593 sulfur Substances 0.000 claims description 2
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- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 241000238370 Sepia Species 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 210000004027 cell Anatomy 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical class OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
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- 239000011780 sodium chloride Substances 0.000 description 4
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical class OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 3
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- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 2
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- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
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- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
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- GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 description 1
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- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
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- 238000012353 t test Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- 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
-
- 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
- C07C323/01—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3816388A DE3816388A1 (de) | 1988-05-13 | 1988-05-13 | Neue-6-phenoxymethyl-4-hydroxytetrahydropyran-2-one und 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2-one, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und neue phenole sowie thiophenole |
| DE19883819999 DE3819999A1 (de) | 1988-06-11 | 1988-06-11 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26257A true PH26257A (en) | 1992-04-01 |
Family
ID=25868078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH38636A PH26257A (en) | 1988-05-13 | 1989-05-11 | Novel 6-phenoxymethyl-4- hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2- ones and the corresponding dihydroxycarboxylic acid derivatives salts and esters processes for the preparation of these compounds their use as pharmaceuticals pharmaceutical preparations and novel phenols and thiophenols |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0341681B1 (pt) |
| JP (1) | JP2833779B2 (pt) |
| KR (1) | KR900018062A (pt) |
| AU (1) | AU615060B2 (pt) |
| CA (1) | CA1338018C (pt) |
| DE (1) | DE58906520D1 (pt) |
| DK (1) | DK235389A (pt) |
| ES (1) | ES2061779T3 (pt) |
| FI (1) | FI96684C (pt) |
| HU (1) | HU206312B (pt) |
| IE (1) | IE63298B1 (pt) |
| IL (1) | IL90249A (pt) |
| NO (1) | NO172538C (pt) |
| NZ (1) | NZ229083A (pt) |
| PH (1) | PH26257A (pt) |
| PT (1) | PT90532B (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3929913A1 (de) * | 1989-09-08 | 1991-04-04 | Hoechst Ag | 4-hydroxytetrahydropyran-2-one sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate sowie vorprodukte |
| KR950005791A (ko) * | 1993-08-09 | 1995-03-20 | 후꾸야마 마사루 | 카르복실산 에스테르-유도체의 제조방법 및 그 방법에 사용되는 4- 플루오로비페닐 유도체 |
| US9045684B2 (en) * | 2012-07-30 | 2015-06-02 | Jnc Corporation | Liquid crystal composition, antioxidant and liquid crystal display device |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3530798A1 (de) * | 1985-08-29 | 1987-03-05 | Hoechst Ag | 6-phenoxymethyl-4-hydroxytetrahydropyran-2-one, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte |
| DE3674521D1 (de) * | 1985-08-29 | 1990-10-31 | Hoechst Ag | 6-phenoxymethyl-4-hydroxytetrahydropyran-2-one, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate 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 |
| DE3929913A1 (de) * | 1989-09-08 | 1991-04-04 | Hoechst Ag | 4-hydroxytetrahydropyran-2-one sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate sowie vorprodukte |
-
1989
- 1989-05-09 IL IL9024989A patent/IL90249A/en not_active IP Right Cessation
- 1989-05-10 DE DE89108378T patent/DE58906520D1/de not_active Expired - Lifetime
- 1989-05-10 EP EP89108378A patent/EP0341681B1/de not_active Expired - Lifetime
- 1989-05-10 ES ES89108378T patent/ES2061779T3/es not_active Expired - Lifetime
- 1989-05-11 FI FI892291A patent/FI96684C/fi not_active IP Right Cessation
- 1989-05-11 PT PT90532A patent/PT90532B/pt not_active IP Right Cessation
- 1989-05-11 NZ NZ229083A patent/NZ229083A/en unknown
- 1989-05-11 PH PH38636A patent/PH26257A/en unknown
- 1989-05-12 AU AU34715/89A patent/AU615060B2/en not_active Ceased
- 1989-05-12 DK DK235389A patent/DK235389A/da not_active Application Discontinuation
- 1989-05-12 NO NO891937A patent/NO172538C/no unknown
- 1989-05-12 HU HU892394A patent/HU206312B/hu not_active IP Right Cessation
- 1989-05-12 IE IE155489A patent/IE63298B1/en not_active IP Right Cessation
- 1989-05-12 CA CA000599613A patent/CA1338018C/en not_active Expired - Fee Related
- 1989-05-12 JP JP1117649A patent/JP2833779B2/ja not_active Expired - Lifetime
- 1989-05-13 KR KR1019890006399A patent/KR900018062A/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| DE58906520D1 (de) | 1994-02-10 |
| DK235389D0 (da) | 1989-05-12 |
| HU206312B (en) | 1992-10-28 |
| IE63298B1 (en) | 1995-04-05 |
| HUT58309A (en) | 1992-02-28 |
| JPH01319472A (ja) | 1989-12-25 |
| IE891554L (en) | 1989-11-13 |
| NO891937D0 (no) | 1989-05-12 |
| AU615060B2 (en) | 1991-09-19 |
| NZ229083A (en) | 1990-12-21 |
| EP0341681A2 (de) | 1989-11-15 |
| NO172538C (no) | 1993-08-04 |
| FI96684B (fi) | 1996-04-30 |
| FI892291A0 (fi) | 1989-05-11 |
| FI892291A (fi) | 1989-11-14 |
| IL90249A0 (en) | 1989-12-15 |
| IL90249A (en) | 1994-01-25 |
| ES2061779T3 (es) | 1994-12-16 |
| EP0341681B1 (de) | 1993-12-29 |
| NO172538B (no) | 1993-04-26 |
| AU3471589A (en) | 1989-12-21 |
| JP2833779B2 (ja) | 1998-12-09 |
| NO891937L (no) | 1989-11-14 |
| PT90532B (pt) | 1994-11-30 |
| KR900018062A (ko) | 1990-12-20 |
| PT90532A (pt) | 1989-11-30 |
| FI96684C (fi) | 1996-08-12 |
| DK235389A (da) | 1989-11-14 |
| CA1338018C (en) | 1996-01-30 |
| EP0341681A3 (en) | 1990-05-16 |
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