NO853935L - Fremgangsm¨te ved fremstilling av 2-pyridin-thiolderivater - Google Patents
Fremgangsm¨te ved fremstilling av 2-pyridin-thiolderivaterInfo
- Publication number
- NO853935L NO853935L NO853935A NO853935A NO853935L NO 853935 L NO853935 L NO 853935L NO 853935 A NO853935 A NO 853935A NO 853935 A NO853935 A NO 853935A NO 853935 L NO853935 L NO 853935L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- pyridine
- compounds
- defined above
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000002253 acid Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- -1 thiol compound Chemical class 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 150000005749 2-halopyridines Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 30
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
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- 241001465754 Metazoa Species 0.000 description 8
- LVWFHYWRBSIXMC-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-phenylmethanone Chemical compound NCCSC1=NC=CC=C1C(=O)C1=CC=CC=C1 LVWFHYWRBSIXMC-UHFFFAOYSA-N 0.000 description 8
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 8
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HPNCVUBDPCPUDK-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)-6-propylpyridin-4-yl]-phenylmethanone Chemical group NCCSC1=NC(CCC)=CC(C(=O)C=2C=CC=CC=2)=C1 HPNCVUBDPCPUDK-UHFFFAOYSA-N 0.000 description 4
- KYYDUQIIPZUYPO-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-(2,5-dimethylphenyl)methanone Chemical compound CC1=CC=C(C)C(C(=O)C=2C(=NC=CC=2)SCCN)=C1 KYYDUQIIPZUYPO-UHFFFAOYSA-N 0.000 description 4
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- FOQYDURHXZVLFT-UHFFFAOYSA-N 2-phenyl-2-pyridin-2-ylethanethioamide Chemical compound C=1C=CC=NC=1C(C(=S)N)C1=CC=CC=C1 FOQYDURHXZVLFT-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CVIGZBUHEDENIJ-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-(4-chlorophenyl)methanone Chemical compound NCCSC1=NC=CC=C1C(=O)C1=CC=C(Cl)C=C1 CVIGZBUHEDENIJ-UHFFFAOYSA-N 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
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- KKJGMDXUAOTRBW-UHFFFAOYSA-N (2-chloropyridin-3-yl)-phenylmethanone Chemical compound ClC1=NC=CC=C1C(=O)C1=CC=CC=C1 KKJGMDXUAOTRBW-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- NUNIXMWDTUKSTG-UHFFFAOYSA-N 2-methoxy-n-methyl-2-pyridin-2-ylethanethioamide Chemical compound CNC(=S)C(OC)C1=CC=CC=N1 NUNIXMWDTUKSTG-UHFFFAOYSA-N 0.000 description 2
- AIMIAJHGOMWBQG-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound NC(=S)C1CCCC2=CC(C)=CN=C21 AIMIAJHGOMWBQG-UHFFFAOYSA-N 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- OGLIEZKGUPAGHK-UHFFFAOYSA-N phenyl-(2-sulfanylidene-1h-pyridin-3-yl)methanone Chemical compound C=1C=CNC(=S)C=1C(=O)C1=CC=CC=C1 OGLIEZKGUPAGHK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- MQDVUDAZJMZQMF-UHFFFAOYSA-N pyridin-2-ylurea Chemical class NC(=O)NC1=CC=CC=N1 MQDVUDAZJMZQMF-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229950005250 tiquinamide Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU843775A HU192875B (en) | 1984-10-05 | 1984-10-05 | Process for preparing 2-pyridinethiol derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO853935L true NO853935L (no) | 1986-04-07 |
Family
ID=10965437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO853935A NO853935L (no) | 1984-10-05 | 1985-10-04 | Fremgangsm¨te ved fremstilling av 2-pyridin-thiolderivater |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4713388A (es) |
| EP (1) | EP0177907B1 (es) |
| JP (1) | JPS6191172A (es) |
| KR (1) | KR860003212A (es) |
| CN (1) | CN85107284A (es) |
| AT (1) | ATE34739T1 (es) |
| AU (1) | AU579665B2 (es) |
| DD (1) | DD238384A5 (es) |
| DE (1) | DE3563048D1 (es) |
| DK (1) | DK455285A (es) |
| ES (1) | ES8704460A1 (es) |
| FI (1) | FI853866L (es) |
| GR (1) | GR852409B (es) |
| HU (1) | HU192875B (es) |
| IL (1) | IL76577A0 (es) |
| IN (1) | IN162570B (es) |
| NO (1) | NO853935L (es) |
| PH (1) | PH21435A (es) |
| PL (1) | PL146371B1 (es) |
| PT (1) | PT81255B (es) |
| SU (1) | SU1346042A3 (es) |
| YU (1) | YU158385A (es) |
| ZA (1) | ZA857676B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1339423C (en) * | 1988-09-14 | 1997-09-02 | Yuji Ono | Pyridine compounds and pharmaceutical use thereof |
| DE69209576D1 (de) * | 1991-05-10 | 1996-05-09 | Takeda Chemical Industries Ltd | Pyridinderivate, deren Herstellung und Anwendung |
| AR029289A1 (es) * | 2000-07-05 | 2003-06-18 | Ishihara Sangyo Kaisha | Derivado de benzoilpiridina o su sal, fungicida que lo contiene como un ingrediente activo, su proceso de produccion e intermediario para producirlo |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| PL1656372T3 (pl) | 2003-07-30 | 2013-08-30 | Rigel Pharmaceuticals Inc | Związki 2,4-pirymidynodiaminy do stosowania w leczeniu lub zapobieganiu chorobom autoimmunologicznym |
| WO2006050480A2 (en) * | 2004-10-29 | 2006-05-11 | Rigel Pharmaceuticals, Inc. | Substituted pyridines with activity on syk kinase |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT238200B (de) * | 1962-03-27 | 1965-01-25 | Degussa | Verfahren zur Herstellung von neuen Pyridinderivaten |
| JPS552920A (en) * | 1978-06-23 | 1980-01-10 | Natl Res Inst For Metals | Method of detecting surface dfect of non-magnetic material |
| US4304781A (en) * | 1978-11-30 | 1981-12-08 | John Wyeth & Brother Limited | Treatment of ulcers and hypertension |
| HU194830B (en) * | 1984-10-05 | 1988-03-28 | Richter Gedeon Vegyeszet | Process for the production of derivatives of piridine |
-
1984
- 1984-10-05 HU HU843775A patent/HU192875B/hu not_active IP Right Cessation
-
1985
- 1985-09-24 PH PH32832A patent/PH21435A/en unknown
- 1985-10-03 US US06/783,875 patent/US4713388A/en not_active Expired - Fee Related
- 1985-10-04 AT AT85112599T patent/ATE34739T1/de not_active IP Right Cessation
- 1985-10-04 JP JP60221714A patent/JPS6191172A/ja active Pending
- 1985-10-04 EP EP85112599A patent/EP0177907B1/de not_active Expired
- 1985-10-04 YU YU01583/85A patent/YU158385A/xx unknown
- 1985-10-04 CN CN198585107284A patent/CN85107284A/zh active Pending
- 1985-10-04 PT PT81255A patent/PT81255B/pt unknown
- 1985-10-04 SU SU853959903A patent/SU1346042A3/ru active
- 1985-10-04 NO NO853935A patent/NO853935L/no unknown
- 1985-10-04 ZA ZA857676A patent/ZA857676B/xx unknown
- 1985-10-04 PL PL1985255643A patent/PL146371B1/pl unknown
- 1985-10-04 GR GR852409A patent/GR852409B/el unknown
- 1985-10-04 IL IL76577A patent/IL76577A0/xx unknown
- 1985-10-04 FI FI853866A patent/FI853866L/fi not_active Application Discontinuation
- 1985-10-04 DK DK455285A patent/DK455285A/da not_active Application Discontinuation
- 1985-10-04 AU AU48328/85A patent/AU579665B2/en not_active Expired - Fee Related
- 1985-10-04 DE DE8585112599T patent/DE3563048D1/de not_active Expired
- 1985-10-04 IN IN778/MAS/85A patent/IN162570B/en unknown
- 1985-10-04 DD DD85281464A patent/DD238384A5/de unknown
- 1985-10-04 ES ES547604A patent/ES8704460A1/es not_active Expired
- 1985-10-05 KR KR1019850007352A patent/KR860003212A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| YU158385A (en) | 1988-04-30 |
| DK455285D0 (da) | 1985-10-04 |
| ATE34739T1 (de) | 1988-06-15 |
| DD238384A5 (de) | 1986-08-20 |
| HUT38907A (en) | 1986-07-28 |
| US4713388A (en) | 1987-12-15 |
| HU192875B (en) | 1987-07-28 |
| AU579665B2 (en) | 1988-12-01 |
| ZA857676B (en) | 1986-06-25 |
| EP0177907B1 (de) | 1988-06-01 |
| DK455285A (da) | 1986-04-06 |
| AU4832885A (en) | 1986-04-10 |
| PL146371B1 (en) | 1989-01-31 |
| IL76577A0 (en) | 1986-02-28 |
| PT81255B (en) | 1987-03-23 |
| PT81255A (en) | 1985-11-01 |
| FI853866A0 (fi) | 1985-10-04 |
| EP0177907A1 (de) | 1986-04-16 |
| SU1346042A3 (ru) | 1987-10-15 |
| ES8704460A1 (es) | 1987-04-01 |
| KR860003212A (ko) | 1986-05-21 |
| IN162570B (es) | 1988-06-11 |
| ES547604A0 (es) | 1987-04-01 |
| FI853866L (fi) | 1986-04-06 |
| GR852409B (es) | 1986-02-04 |
| CN85107284A (zh) | 1986-06-10 |
| PH21435A (en) | 1987-10-15 |
| JPS6191172A (ja) | 1986-05-09 |
| PL255643A1 (en) | 1987-01-12 |
| DE3563048D1 (en) | 1988-07-07 |
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