DD220025A5 - Verfahren zur herstellung von benzamidin-derivaten - Google Patents
Verfahren zur herstellung von benzamidin-derivaten Download PDFInfo
- Publication number
- DD220025A5 DD220025A5 DD84265830A DD26583084A DD220025A5 DD 220025 A5 DD220025 A5 DD 220025A5 DD 84265830 A DD84265830 A DD 84265830A DD 26583084 A DD26583084 A DD 26583084A DD 220025 A5 DD220025 A5 DD 220025A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- compound
- derivatives
- water
- direct bond
- Prior art date
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- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical class NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 230000009471 action Effects 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000008359 benzonitriles Chemical class 0.000 claims abstract description 5
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 150000003937 benzamidines Chemical class 0.000 claims abstract description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract 3
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- VEVZSMAEJFVWIL-UHFFFAOYSA-O cyanidin cation Chemical compound [O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC=C(O)C(O)=C1 VEVZSMAEJFVWIL-UHFFFAOYSA-O 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 235000007336 cyanidin Nutrition 0.000 claims 1
- -1 aniline derivatives sodium nitrite Chemical class 0.000 abstract description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 45
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- 239000000243 solution Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 22
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- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LJWKFGGDMBPPAZ-UHFFFAOYSA-N ethoxyethane;toluene Chemical group CCOCC.CC1=CC=CC=C1 LJWKFGGDMBPPAZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- BPWMEBANYHWZOV-UHFFFAOYSA-N methyl(2-methyltetradecan-2-yl)carbamic acid Chemical compound CCCCCCCCCCCCC(C)(C)N(C)C(O)=O BPWMEBANYHWZOV-UHFFFAOYSA-N 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 231100000046 skin rash Toxicity 0.000 description 1
- 231100000370 skin sensitisation Toxicity 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/19—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8312824A FR2550192B1 (fr) | 1983-08-03 | 1983-08-03 | Nouveaux derives de la benzamidine a activite antimicrobienne, leur procede de preparation, leur utilisation en tant que medicaments desinfectants ou conservateurs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD220025A5 true DD220025A5 (de) | 1985-03-20 |
Family
ID=9291379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84265830A DD220025A5 (de) | 1983-08-03 | 1984-07-31 | Verfahren zur herstellung von benzamidin-derivaten |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4720581A (cs) |
| EP (1) | EP0136195B1 (cs) |
| JP (1) | JPS6054351A (cs) |
| KR (1) | KR920000373B1 (cs) |
| AR (1) | AR242556A1 (cs) |
| AT (1) | ATE27952T1 (cs) |
| AU (1) | AU563648B2 (cs) |
| CA (1) | CA1238922A (cs) |
| CS (1) | CS246088B2 (cs) |
| DD (1) | DD220025A5 (cs) |
| DE (1) | DE3464362D1 (cs) |
| DK (1) | DK158662C (cs) |
| ES (1) | ES534828A0 (cs) |
| FI (1) | FI77020C (cs) |
| FR (1) | FR2550192B1 (cs) |
| GR (1) | GR82449B (cs) |
| HU (1) | HU192567B (cs) |
| IL (1) | IL72480A (cs) |
| MA (1) | MA20180A1 (cs) |
| NO (1) | NO157618C (cs) |
| NZ (1) | NZ209092A (cs) |
| PT (1) | PT79003B (cs) |
| SU (1) | SU1319784A3 (cs) |
| YU (1) | YU127684A (cs) |
| ZA (1) | ZA845682B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2504361Y2 (ja) * | 1990-12-14 | 1996-07-10 | 大和ハウス工業株式会社 | 建物の配管固定構造 |
| DE4424713A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Substituierte Benzamidine, ihre Herstellung und Verwendung als Arnzneistoffe |
| DE4447361A1 (de) * | 1994-12-21 | 1996-06-27 | Schuelke & Mayr Gmbh | Biozide Alkohole, ihre Herstellung und ihre Verwendung |
| DE19515500A1 (de) * | 1995-04-27 | 1996-10-31 | Thomae Gmbh Dr K | Substituierte Phenylamidine, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| RU2142939C1 (ru) * | 1996-10-28 | 1999-12-20 | Эл Джи Кемикал Лтд. | Избирательно действующие ингибиторы тромбина и фармацевтическая композиция на их основе |
| TW523504B (en) * | 1997-11-20 | 2003-03-11 | Teijin Ltd | Biphenylamidine derivatives |
| AU2004218187C1 (en) * | 2003-02-19 | 2011-04-07 | Eisai R&D Management Co., Ltd. | Methods for producing cyclic benzamidine derivatives |
| CN1980905B (zh) * | 2004-07-05 | 2010-04-21 | 同和药品株式会社 | 制备n-羟基-4-{5-[4-(5-异丙基-2-甲基-1,3-噻唑-4-基)-苯氧基]-戊氧基}-苄脒的改进方法 |
| CN111362834B (zh) * | 2020-02-26 | 2021-04-02 | 湖南大学 | 一种具有抗耐药性的抗菌脒类低聚物及其制作方法和用途 |
| CN114773250A (zh) * | 2021-08-02 | 2022-07-22 | 湖南大学 | 具有抗耐药性的抗菌脒类低聚物及其制作方法和用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2934438A (en) * | 1958-03-20 | 1960-04-26 | Michener Harold David | Preservation process with alkyl guanidines |
| US3769427A (en) * | 1970-10-01 | 1973-10-30 | Armour Pharma | Pharmaceutical compositions and methods of using same |
| IT1153988B (it) * | 1981-10-05 | 1987-01-21 | Medea Res Srl | Composizioni ad attivita' antimicrobica |
-
1983
- 1983-08-03 FR FR8312824A patent/FR2550192B1/fr not_active Expired
-
1984
- 1984-07-13 AT AT84401494T patent/ATE27952T1/de not_active IP Right Cessation
- 1984-07-13 EP EP84401494A patent/EP0136195B1/fr not_active Expired
- 1984-07-13 DE DE8484401494T patent/DE3464362D1/de not_active Expired
- 1984-07-17 US US06/631,753 patent/US4720581A/en not_active Expired - Fee Related
- 1984-07-17 CA CA000459095A patent/CA1238922A/en not_active Expired
- 1984-07-18 AU AU30790/84A patent/AU563648B2/en not_active Ceased
- 1984-07-19 YU YU01276/84A patent/YU127684A/xx unknown
- 1984-07-20 IL IL72480A patent/IL72480A/xx unknown
- 1984-07-20 MA MA20404A patent/MA20180A1/fr unknown
- 1984-07-23 ZA ZA845682A patent/ZA845682B/xx unknown
- 1984-07-24 DK DK362384A patent/DK158662C/da not_active IP Right Cessation
- 1984-07-30 CS CS845841A patent/CS246088B2/cs unknown
- 1984-07-31 GR GR75458A patent/GR82449B/el unknown
- 1984-07-31 DD DD84265830A patent/DD220025A5/de not_active IP Right Cessation
- 1984-07-31 PT PT79003A patent/PT79003B/pt not_active IP Right Cessation
- 1984-08-01 HU HU842938A patent/HU192567B/hu not_active IP Right Cessation
- 1984-08-01 KR KR1019840004587A patent/KR920000373B1/ko not_active Expired
- 1984-08-01 JP JP59160306A patent/JPS6054351A/ja active Pending
- 1984-08-02 NO NO843114A patent/NO157618C/no unknown
- 1984-08-02 NZ NZ209092A patent/NZ209092A/en unknown
- 1984-08-02 FI FI843061A patent/FI77020C/fi not_active IP Right Cessation
- 1984-08-02 ES ES534828A patent/ES534828A0/es active Granted
- 1984-08-02 AR AR84297437A patent/AR242556A1/es active
- 1984-08-03 SU SU843781801A patent/SU1319784A3/ru active
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| Date | Code | Title | Description |
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| ENJ | Ceased due to non-payment of renewal fee |