NO782404L - Fremgangsmaate for fremstilling av oksadiazolderivater - Google Patents
Fremgangsmaate for fremstilling av oksadiazolderivaterInfo
- Publication number
- NO782404L NO782404L NO782404A NO782404A NO782404L NO 782404 L NO782404 L NO 782404L NO 782404 A NO782404 A NO 782404A NO 782404 A NO782404 A NO 782404A NO 782404 L NO782404 L NO 782404L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- compounds
- oxadiazole
- solution
- dichloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 5
- 150000004866 oxadiazoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 description 31
- -1 alkyl radical Chemical class 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- DXAYHBRZHFYCBA-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methyl]-1,2,4-oxadiazol-3-amine Chemical compound NC1=NOC(CC=2C(=CC=CC=2Cl)Cl)=N1 DXAYHBRZHFYCBA-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- MGWHFRGJEDODLL-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methyl]-3-(4-methylpiperazin-1-yl)-1,2,4-oxadiazole Chemical compound C1CN(C)CCN1C1=NOC(CC=2C(=CC=CC=2Cl)Cl)=N1 MGWHFRGJEDODLL-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- LSSHIYBDALPHTL-UHFFFAOYSA-N ethyl n-[5-[(2,6-dichlorophenyl)methyl]-1,2,4-oxadiazol-3-yl]methanimidate Chemical compound CCOC=NC1=NOC(CC=2C(=CC=CC=2Cl)Cl)=N1 LSSHIYBDALPHTL-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- UTKBKGSHXKTACH-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-2-isothiocyanatoethanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)CN=C=S UTKBKGSHXKTACH-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- SFAILOOQFZNOAU-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetic acid Chemical compound OC(=O)CC1=C(Cl)C=CC=C1Cl SFAILOOQFZNOAU-UHFFFAOYSA-N 0.000 description 1
- VFRDBQGBQYINBH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=C(Cl)C=CC=C1Cl VFRDBQGBQYINBH-UHFFFAOYSA-N 0.000 description 1
- YYNYPRVLHIOAGG-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methyl]-n-methyl-1,2,4-oxadiazol-3-amine Chemical compound CNC1=NOC(CC=2C(=CC=CC=2Cl)Cl)=N1 YYNYPRVLHIOAGG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 201000004239 Secondary hypertension Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7721447A FR2397408A1 (fr) | 1977-07-12 | 1977-07-12 | Derives d'oxadiazole, leur preparation et leur application en therapeutique |
| FR7817114A FR2428034A2 (fr) | 1978-06-08 | 1978-06-08 | Derives d'oxadiazole-1,2,4, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782404L true NO782404L (no) | 1979-01-15 |
Family
ID=26220123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782404A NO782404L (no) | 1977-07-12 | 1978-07-10 | Fremgangsmaate for fremstilling av oksadiazolderivater |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US4261994A (es) |
| EP (1) | EP0000452B1 (es) |
| JP (1) | JPS5834473B2 (es) |
| AR (1) | AR222310A1 (es) |
| AT (1) | AT362367B (es) |
| AU (1) | AU515506B2 (es) |
| CA (1) | CA1130806A (es) |
| DE (1) | DE2860691D1 (es) |
| DK (1) | DK307378A (es) |
| ES (2) | ES471609A1 (es) |
| FI (1) | FI782220A (es) |
| GR (1) | GR64924B (es) |
| IL (1) | IL55104A (es) |
| IT (1) | IT1096906B (es) |
| NO (1) | NO782404L (es) |
| NZ (1) | NZ187825A (es) |
| PT (1) | PT68267A (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625877B2 (es) * | 1973-06-19 | 1981-06-15 | ||
| DE2860691D1 (en) * | 1977-07-12 | 1981-08-13 | Synthelabo | 1,2,4-oxadiazol derivatives, their preparation and application in pharmaceutical compositions |
| US5180731A (en) * | 1986-06-03 | 1993-01-19 | Sumitomo Pharmaceuticals Company, Limited | Aminoazole derivatives and their production and use |
| US4914112A (en) * | 1986-06-03 | 1990-04-03 | Sumitomo Pharmaceuticals Company, Limited | Aminoazole derivatives and their production and use |
| AT395853B (de) * | 1991-01-31 | 1993-03-25 | Chem Pharm Forsch Gmbh | Neue imidazolderivate, verfahren zu ihrer herstellung und ihre verwendung |
| WO1993009106A1 (en) * | 1991-10-28 | 1993-05-13 | Tsentr Po Khimii Lekarstvennykh Sredstv | Derivatives of 5-phenoxymethyl-1,2,4-oxadiazol, their salts, method of obtaining them and a pharmaceutical preparation with antihypertensive, antianginal, antiarrhythmic and antiglaucomatomic properties based on them |
| BR9608229A (pt) * | 1995-05-09 | 1998-12-29 | Bayer Ag | Cetoenóis alquil-dihalogenofenil-substituídos |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1053825A (es) * | 1963-03-22 | |||
| US3564608A (en) * | 1965-07-30 | 1971-02-16 | Olin Corp | Selected n-acylsubstituted-n'-hydroxyguanidines |
| DE1670338A1 (de) * | 1966-03-14 | 1972-08-10 | Heyden Chem Fab | Verfahren zur Herstellung von antimikrobiell wirksamen Nitrofuranderivaten |
| FR1559629A (es) * | 1966-09-23 | 1969-03-14 | ||
| US3452035A (en) * | 1966-12-23 | 1969-06-24 | American Cyanamid Co | 2 - amino - 5 - (5 - nitro - 1 - substituted-2 - imidazolyl) - 1,3,4 - thiadiazoles and oxadiazoles |
| US3720685A (en) * | 1970-07-15 | 1973-03-13 | Squibb & Sons Inc | 3-amino-5-benzyl-1,2,4-oxadiazoles |
| GB1314427A (en) * | 1970-07-17 | 1973-04-26 | Beecham Group Ltd | Amino acid esters of 2,2-dialkyl-4-4-pyridyl-2h-7-substituted- chromen-5-ols |
| DE2054342A1 (de) * | 1970-11-05 | 1972-05-10 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Neue 1,2,4-Oxdiazole |
| US3879407A (en) * | 1973-02-09 | 1975-04-22 | Johnson & Son Inc S C | 1,2,4-Oxadiazole and thiadiazole esters and compositions containing same |
| HU169666B (es) * | 1973-12-29 | 1977-02-28 | ||
| DE2860691D1 (en) * | 1977-07-12 | 1981-08-13 | Synthelabo | 1,2,4-oxadiazol derivatives, their preparation and application in pharmaceutical compositions |
-
1978
- 1978-06-20 DE DE7878400026T patent/DE2860691D1/de not_active Expired
- 1978-06-20 EP EP78400026A patent/EP0000452B1/fr not_active Expired
- 1978-07-07 IL IL55104A patent/IL55104A/xx unknown
- 1978-07-07 DK DK783073A patent/DK307378A/da not_active Application Discontinuation
- 1978-07-07 US US05/922,527 patent/US4261994A/en not_active Expired - Lifetime
- 1978-07-10 GR GR56739A patent/GR64924B/el unknown
- 1978-07-10 NZ NZ187825A patent/NZ187825A/xx unknown
- 1978-07-10 IT IT25497/78A patent/IT1096906B/it active
- 1978-07-10 CA CA307,090A patent/CA1130806A/en not_active Expired
- 1978-07-10 AU AU37909/78A patent/AU515506B2/en not_active Expired
- 1978-07-10 NO NO782404A patent/NO782404L/no unknown
- 1978-07-10 PT PT68267A patent/PT68267A/pt unknown
- 1978-07-11 ES ES471609A patent/ES471609A1/es not_active Expired
- 1978-07-11 FI FI782220A patent/FI782220A/fi not_active Application Discontinuation
- 1978-07-11 JP JP53085017A patent/JPS5834473B2/ja not_active Expired
- 1978-07-12 AR AR272930A patent/AR222310A1/es active
- 1978-07-12 AT AT505378A patent/AT362367B/de not_active IP Right Cessation
-
1979
- 1979-03-12 ES ES478527A patent/ES478527A1/es not_active Expired
- 1979-04-27 US US06/034,197 patent/US4242352A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GR64924B (en) | 1980-06-09 |
| FI782220A (fi) | 1979-01-13 |
| ES471609A1 (es) | 1979-09-16 |
| EP0000452B1 (fr) | 1981-05-06 |
| US4242352A (en) | 1980-12-30 |
| CA1130806A (en) | 1982-08-31 |
| DE2860691D1 (en) | 1981-08-13 |
| IT7825497A0 (it) | 1978-07-10 |
| JPS5419978A (en) | 1979-02-15 |
| IT1096906B (it) | 1985-08-26 |
| NZ187825A (en) | 1980-03-05 |
| JPS5834473B2 (ja) | 1983-07-27 |
| IL55104A0 (en) | 1978-09-29 |
| DK307378A (da) | 1979-01-13 |
| IL55104A (en) | 1982-07-30 |
| AT362367B (de) | 1981-05-11 |
| PT68267A (fr) | 1978-08-01 |
| AU515506B2 (en) | 1981-04-09 |
| AR222310A1 (es) | 1981-05-15 |
| US4261994A (en) | 1981-04-14 |
| EP0000452A1 (fr) | 1979-01-24 |
| ES478527A1 (es) | 1979-05-16 |
| ATA505378A (de) | 1980-10-15 |
| AU3790978A (en) | 1980-01-17 |
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