CH641774A5 - Medicaments mucolytiques a base de benzamidoalkyl-mercaptans. - Google Patents
Medicaments mucolytiques a base de benzamidoalkyl-mercaptans. Download PDFInfo
- Publication number
- CH641774A5 CH641774A5 CH716979A CH716979A CH641774A5 CH 641774 A5 CH641774 A5 CH 641774A5 CH 716979 A CH716979 A CH 716979A CH 716979 A CH716979 A CH 716979A CH 641774 A5 CH641774 A5 CH 641774A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound according
- hydrochloride
- contain
- acid
- inhalation
- Prior art date
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- 229940066491 mucolytics Drugs 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 210000003097 mucus Anatomy 0.000 claims description 8
- VQLAUZQBHULEDZ-UHFFFAOYSA-N n-(2-sulfanylethyl)benzamide Chemical compound SCCNC(=O)C1=CC=CC=C1 VQLAUZQBHULEDZ-UHFFFAOYSA-N 0.000 claims description 7
- 206010037368 Pulmonary congestion Diseases 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- TWTVLBCKCXYHPV-UHFFFAOYSA-N 4-chloro-n-(2-sulfanylethyl)benzamide Chemical compound SCCNC(=O)C1=CC=C(Cl)C=C1 TWTVLBCKCXYHPV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ZWUHJFCTWYZUIY-UHFFFAOYSA-N 4-methoxy-n-(2-sulfanylethyl)benzamide Chemical compound COC1=CC=C(C(=O)NCCS)C=C1 ZWUHJFCTWYZUIY-UHFFFAOYSA-N 0.000 claims description 3
- VGHWCTAIXNVUJL-UHFFFAOYSA-N 4-methyl-n-(2-sulfanylethyl)benzamide Chemical compound CC1=CC=C(C(=O)NCCS)C=C1 VGHWCTAIXNVUJL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003172 expectorant agent Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- -1 amino, carboxy Chemical group 0.000 description 24
- 239000000203 mixture Substances 0.000 description 12
- 230000000510 mucolytic effect Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 210000002784 stomach Anatomy 0.000 description 8
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YGAPOICUMNPIPF-UHFFFAOYSA-N 4-methoxybenzenecarbothioic s-acid Chemical compound COC1=CC=C(C(S)=O)C=C1 YGAPOICUMNPIPF-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- SYRDMPUJUIXSPL-UHFFFAOYSA-N 4-amino-N-(2-sulfanylethyl)benzamide Chemical compound SCCNC(C1=CC=C(C=C1)N)=O SYRDMPUJUIXSPL-UHFFFAOYSA-N 0.000 description 4
- PJHWTWHVCOZCPU-UHFFFAOYSA-N 4-methylbenzenecarbothioic s-acid Chemical compound CC1=CC=C(C(O)=S)C=C1 PJHWTWHVCOZCPU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
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- DJJIBYYAHJOUMY-UHFFFAOYSA-N 2-aminopropane-1-thiol Chemical compound CC(N)CS DJJIBYYAHJOUMY-UHFFFAOYSA-N 0.000 description 2
- NQKUVVLYLMBAEP-UHFFFAOYSA-N 3,4,5-trimethoxybenzenecarbothioic s-acid Chemical compound COC1=CC(C(S)=O)=CC(OC)=C1OC NQKUVVLYLMBAEP-UHFFFAOYSA-N 0.000 description 2
- HMDHOFNCICZZPD-UHFFFAOYSA-N 3,4-dimethylbenzenecarbothioic s-acid Chemical compound CC1=CC=C(C(O)=S)C=C1C HMDHOFNCICZZPD-UHFFFAOYSA-N 0.000 description 2
- GMEDUXHKSSWXSL-UHFFFAOYSA-N 3-sulfanylpropylazanium;chloride Chemical compound Cl.NCCCS GMEDUXHKSSWXSL-UHFFFAOYSA-N 0.000 description 2
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- LODPBQFMFWUQFE-UHFFFAOYSA-N 2-chloro-N-(3-sulfanylpropyl)benzamide Chemical compound ClC1=C(C(=O)NCCCS)C=CC=C1 LODPBQFMFWUQFE-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- MRPINLYTPGPSAX-UHFFFAOYSA-N 3,4,5-trichloro-N-(2-sulfanylethyl)benzamide Chemical compound ClC=1C=C(C(=O)NCCS)C=C(C1Cl)Cl MRPINLYTPGPSAX-UHFFFAOYSA-N 0.000 description 1
- SRYGWCIQJICGNH-UHFFFAOYSA-N 3,4,5-trichloro-N-(3-sulfanylpropyl)benzamide Chemical compound ClC=1C=C(C(=O)NCCCS)C=C(C1Cl)Cl SRYGWCIQJICGNH-UHFFFAOYSA-N 0.000 description 1
- ICUICNRYLHKQGS-UHFFFAOYSA-N 3,4,5-trichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 ICUICNRYLHKQGS-UHFFFAOYSA-N 0.000 description 1
- ULSJLEJQDPUSKY-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-sulfanylethyl)benzamide Chemical compound COC1=CC(C(=O)NCCS)=CC(OC)=C1OC ULSJLEJQDPUSKY-UHFFFAOYSA-N 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- RGAKSNQOIIYQRM-UHFFFAOYSA-N 3,4-dimethylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1C RGAKSNQOIIYQRM-UHFFFAOYSA-N 0.000 description 1
- OQVKGSDRYMYQKF-UHFFFAOYSA-N 3-(trifluoromethyl)benzenecarbothioic s-acid Chemical compound OC(=S)C1=CC=CC(C(F)(F)F)=C1 OQVKGSDRYMYQKF-UHFFFAOYSA-N 0.000 description 1
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
- PWCDFLBEHVHREU-UHFFFAOYSA-N 4-(2-sulfanylethylcarbamoyl)benzoic acid Chemical compound C(=O)(O)C1=CC=C(C(=O)NCCS)C=C1 PWCDFLBEHVHREU-UHFFFAOYSA-N 0.000 description 1
- REOIAZFOEPNVFL-UHFFFAOYSA-N 4-amino-N-(2-chloroethyl)benzamide Chemical compound ClCCNC(C1=CC=C(C=C1)N)=O REOIAZFOEPNVFL-UHFFFAOYSA-N 0.000 description 1
- SZSBCGVLFJPZRC-UHFFFAOYSA-N 4-bromo-N-(3-sulfanylpropyl)benzamide Chemical compound BrC1=CC=C(C(=O)NCCCS)C=C1 SZSBCGVLFJPZRC-UHFFFAOYSA-N 0.000 description 1
- WCFCNBNAVBPKBV-UHFFFAOYSA-N 4-bromo-n-(2-sulfanylethyl)benzamide Chemical compound SCCNC(=O)C1=CC=C(Br)C=C1 WCFCNBNAVBPKBV-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- OYEQKMASMPBQMP-UHFFFAOYSA-N 4-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(Cl)=O)C=C1 OYEQKMASMPBQMP-UHFFFAOYSA-N 0.000 description 1
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- SREWEYBSNAIRAI-UHFFFAOYSA-N 4-fluoro-N-(3-sulfanylpropyl)benzamide Chemical compound FC1=CC=C(C(=O)NCCCS)C=C1 SREWEYBSNAIRAI-UHFFFAOYSA-N 0.000 description 1
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- ZGWQSLHLLDAMNS-UHFFFAOYSA-N 4-methoxy-N-(3-sulfanylpropyl)benzamide Chemical compound COC1=CC=C(C(=O)NCCCS)C=C1 ZGWQSLHLLDAMNS-UHFFFAOYSA-N 0.000 description 1
- DTVKYSKUTKSXJJ-UHFFFAOYSA-N 4-methyl-N-(3-sulfanylpropyl)benzamide Chemical compound CC1=CC=C(C(=O)NCCCS)C=C1 DTVKYSKUTKSXJJ-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93274878A | 1978-08-10 | 1978-08-10 | |
| US462479A | 1979-01-18 | 1979-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641774A5 true CH641774A5 (fr) | 1984-03-15 |
Family
ID=26673255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH716979A CH641774A5 (fr) | 1978-08-10 | 1979-08-03 | Medicaments mucolytiques a base de benzamidoalkyl-mercaptans. |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL57859A (en) * | 1978-08-10 | 1983-02-23 | Robins Co Inc A H | Salts of benzene and thiophenecarbothioic acid 2-aminoalkyl esters and pharmaceutical compositions containing them |
| JPS63290860A (ja) * | 1987-05-22 | 1988-11-28 | Sanraku Inc | アミノエチルシステイン誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005222A (en) * | 1975-05-21 | 1977-01-25 | Mead Johnson & Company | Mucolytic mercaptoacylamidobenzoic and benzenesulfonic acid compounds and process |
-
1979
- 1979-07-24 IL IL57881A patent/IL57881A/xx unknown
- 1979-08-03 CH CH716979A patent/CH641774A5/fr not_active IP Right Cessation
- 1979-08-08 GB GB7927693A patent/GB2028656B/en not_active Expired
- 1979-08-08 EG EG485/79A patent/EG14415A/xx active
- 1979-08-08 GB GB8204970A patent/GB2098596B/en not_active Expired
- 1979-08-08 IE IE1519/79A patent/IE48793B1/en unknown
- 1979-08-09 CA CA333,426A patent/CA1129881A/en not_active Expired
- 1979-08-09 FI FI792475A patent/FI69059C/fi not_active IP Right Cessation
- 1979-08-09 ES ES483270A patent/ES483270A1/es not_active Expired
- 1979-08-09 FR FR7920413A patent/FR2432868A1/fr active Granted
- 1979-08-09 DK DK333979A patent/DK333979A/da not_active Application Discontinuation
- 1979-08-09 IT IT68642/79A patent/IT1119136B/it active
- 1979-08-09 DE DE19792932403 patent/DE2932403A1/de active Granted
- 1979-08-10 AU AU49783/79A patent/AU526168B2/en not_active Ceased
- 1979-11-22 ES ES486226A patent/ES486226A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2932403C2 (enrdf_load_stackoverflow) | 1989-06-29 |
| GB2028656B (en) | 1983-03-09 |
| IL57881A (en) | 1982-12-31 |
| AU526168B2 (en) | 1982-12-23 |
| IE48793B1 (en) | 1985-05-15 |
| ES486226A1 (es) | 1980-06-16 |
| AU4978379A (en) | 1980-02-14 |
| FI69059B (fi) | 1985-08-30 |
| IL57881A0 (en) | 1979-11-30 |
| IE791519L (en) | 1980-02-10 |
| FR2432868A1 (fr) | 1980-03-07 |
| GB2028656A (en) | 1980-03-12 |
| ES483270A1 (es) | 1980-04-16 |
| FI792475A7 (fi) | 1980-02-11 |
| DE2932403A1 (de) | 1980-02-21 |
| FI69059C (fi) | 1985-12-10 |
| DK333979A (da) | 1980-02-11 |
| GB2098596A (en) | 1982-11-24 |
| FR2432868B1 (enrdf_load_stackoverflow) | 1981-07-17 |
| IT1119136B (it) | 1986-03-03 |
| EG14415A (en) | 1983-09-30 |
| IT7968642A0 (it) | 1979-08-09 |
| GB2098596B (en) | 1983-06-02 |
| CA1129881A (en) | 1982-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |