CA1150272A - 2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles - Google Patents
2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazolesInfo
- Publication number
- CA1150272A CA1150272A CA000355635A CA355635A CA1150272A CA 1150272 A CA1150272 A CA 1150272A CA 000355635 A CA000355635 A CA 000355635A CA 355635 A CA355635 A CA 355635A CA 1150272 A CA1150272 A CA 1150272A
- Authority
- CA
- Canada
- Prior art keywords
- group
- trimethoxyphenyl
- compound
- peptic ulcer
- ulcer
- 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.)
- Expired
Links
- -1 2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- FCQGHVXXICVSIF-UHFFFAOYSA-N 3,4,5-trimethoxybenzenecarbothioamide Chemical compound COC1=CC(C(N)=S)=CC(OC)=C1OC FCQGHVXXICVSIF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 41
- 208000008469 Peptic Ulcer Diseases 0.000 abstract description 38
- 208000011906 peptic ulcer disease Diseases 0.000 abstract description 37
- 230000002467 anti-pepsin effect Effects 0.000 abstract description 20
- 230000000694 effects Effects 0.000 abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 150000003557 thiazoles Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 63
- 241000700159 Rattus Species 0.000 description 20
- 208000025865 Ulcer Diseases 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 231100000397 ulcer Toxicity 0.000 description 20
- 239000013078 crystal Substances 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- ZPACYDRSPFRDHO-ROBAGEODSA-N Gefarnate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(=O)OC\C=C(/C)CCC=C(C)C ZPACYDRSPFRDHO-ROBAGEODSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
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- 239000000460 chlorine Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
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- HYMSODFAXMRQCU-UHFFFAOYSA-N 1-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazol-5-yl]ethanone Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C)N=2)C(C)=O)=C1 HYMSODFAXMRQCU-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- KBXUOHZHHFXVDI-UHFFFAOYSA-N 2,3,4-trimethoxybenzenecarbothioamide Chemical compound COC1=CC=C(C(N)=S)C(OC)=C1OC KBXUOHZHHFXVDI-UHFFFAOYSA-N 0.000 description 4
- RJAHEEXALIVZOV-UHFFFAOYSA-N 4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C)N=2)C(O)=O)=C1 RJAHEEXALIVZOV-UHFFFAOYSA-N 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 3
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- 238000011888 autopsy Methods 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- GGNMTJKRHHLJHH-UHFFFAOYSA-N 3,4,5-trimethoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 2
- ZJXSVGRFSGXNTC-UHFFFAOYSA-N 4,5-dimethyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(C)=C(C)N=2)=C1 ZJXSVGRFSGXNTC-UHFFFAOYSA-N 0.000 description 2
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- ZTOXCZMCCDLXAA-UHFFFAOYSA-N 4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole Chemical compound COC1=C(OC)C(OC)=CC(C=2SC=C(C)N=2)=C1 ZTOXCZMCCDLXAA-UHFFFAOYSA-N 0.000 description 2
- OXWRIAJMFOSJDJ-UHFFFAOYSA-N 4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C)N=2)C(N)=O)=C1 OXWRIAJMFOSJDJ-UHFFFAOYSA-N 0.000 description 2
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000001175 peptic effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002562 urinalysis Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000417020A CA1158247A (en) | 1979-07-09 | 1982-12-03 | 2,(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP87055/79 | 1979-07-09 | ||
| JP8705579A JPS5612377A (en) | 1979-07-09 | 1979-07-09 | Novel thiazole derivative, its preparation, and drug for ulcer having andigestive action |
| JP6850780A JPS56164175A (en) | 1980-05-23 | 1980-05-23 | Novel thiazole derivative and antipeptic ulcer agent containing the same as active constituent |
| JP68507/80 | 1980-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1150272A true CA1150272A (en) | 1983-07-19 |
Family
ID=26409723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000355635A Expired CA1150272A (en) | 1979-07-09 | 1980-07-07 | 2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4363813A (show.php) |
| CA (1) | CA1150272A (show.php) |
| DE (1) | DE3026054C2 (show.php) |
| ES (2) | ES493650A0 (show.php) |
| FR (1) | FR2465729A1 (show.php) |
| GB (1) | GB2056440B (show.php) |
| IT (1) | IT1131682B (show.php) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5772975A (en) * | 1980-10-24 | 1982-05-07 | Kureha Chem Ind Co Ltd | 2-substituted phenylthiazole derviative, and medicine for peptic ulcer containing said derivative as active component |
| DE3425118A1 (de) * | 1984-07-07 | 1986-01-16 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue redox-indikatoren |
| US4746669A (en) * | 1985-12-23 | 1988-05-24 | Merck & Co., Inc. | Substituted thiazoles as immunoregulants |
| FR2625199B1 (fr) * | 1987-12-23 | 1991-03-22 | Irceba | Derives oxyimino du thiazole, procede de preparation et utilisation en therapeutique |
| DE69122084T2 (de) * | 1990-11-30 | 1997-04-03 | Teijin Ltd., Osaka | 2-arylthiazolderivat sowie dieses enthaltendes arzneimittel |
| EP0600092A4 (en) * | 1992-05-29 | 1994-09-21 | Otsuka Pharma Co Ltd | Thiazole derivative. |
| US5639770A (en) * | 1992-05-29 | 1997-06-17 | Otsuka Pharmaceutical Co., Ltd. | Thiazole derivatives |
| EP1577289A1 (en) * | 2004-03-18 | 2005-09-21 | Revotar Biopharmaceuticals AG | Non-glycosylated/-glycosidic/-peptidic small molecule selectin inhibitors for the treament of inflammatory disorders |
| EP1764095A1 (en) * | 2005-09-20 | 2007-03-21 | Revotar Biopharmaceuticals AG | Novel nitrocatechol derivatives having selectin ligand activity |
| EP1764093A1 (en) * | 2005-09-20 | 2007-03-21 | Revotar Biopharmaceuticals AG | Novel aromatic compounds and their use in medical applications |
| EP1764094A1 (en) * | 2005-09-20 | 2007-03-21 | Revotar Biopharmaceuticals AG | Novel multi-cyclic compounds and their use |
| EP1764096A1 (en) * | 2005-09-20 | 2007-03-21 | Revotar Biopharmaceuticals AG | Novel phloroglucinol derivatives having selectin ligand activity |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1743083A (en) * | 1928-02-03 | 1930-01-07 | Winthrop Chem Co | Catechol thiazoles and process of making the same |
| US1970656A (en) * | 1931-11-04 | 1934-08-21 | Winthrop Chem Co Inc | Thiazole compound and process of producing the same |
| US2030373A (en) * | 1932-08-18 | 1936-02-11 | Winthrop Chem Co Inc | Derivatives of thiazole and process of preparing the same |
| US2014498A (en) * | 1932-08-18 | 1935-09-17 | Winthrop Chem Co Inc | Halogenated derivatives of thiazole and process of preparing the same |
| US4154947A (en) * | 1978-03-13 | 1979-05-15 | American Cyanamid Company | Heterocyclic substituted benzylideneaminoguanidines |
-
1980
- 1980-06-27 US US06/163,507 patent/US4363813A/en not_active Expired - Lifetime
- 1980-07-07 CA CA000355635A patent/CA1150272A/en not_active Expired
- 1980-07-08 FR FR8015210A patent/FR2465729A1/fr active Granted
- 1980-07-08 GB GB8022292A patent/GB2056440B/en not_active Expired
- 1980-07-08 IT IT23315/80A patent/IT1131682B/it active
- 1980-07-09 ES ES493650A patent/ES493650A0/es active Granted
- 1980-07-09 DE DE3026054A patent/DE3026054C2/de not_active Expired
-
1981
- 1981-02-13 ES ES500076A patent/ES8201565A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3026054C2 (de) | 1982-03-11 |
| IT1131682B (it) | 1986-06-25 |
| ES8105987A1 (es) | 1981-07-01 |
| ES500076A0 (es) | 1982-01-01 |
| GB2056440A (en) | 1981-03-18 |
| ES493650A0 (es) | 1981-07-01 |
| FR2465729A1 (fr) | 1981-03-27 |
| GB2056440B (en) | 1983-05-25 |
| ES8201565A1 (es) | 1982-01-01 |
| IT8023315A0 (it) | 1980-07-08 |
| US4363813A (en) | 1982-12-14 |
| FR2465729B1 (show.php) | 1983-03-18 |
| DE3026054A1 (de) | 1981-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |