HU188035B - Process for producing new plantinum-diamine complex - Google Patents
Process for producing new plantinum-diamine complex Download PDFInfo
- Publication number
- HU188035B HU188035B HU833623A HU362383A HU188035B HU 188035 B HU188035 B HU 188035B HU 833623 A HU833623 A HU 833623A HU 362383 A HU362383 A HU 362383A HU 188035 B HU188035 B HU 188035B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- defined above
- cis
- platinum
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 46
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 19
- 229910052697 platinum Inorganic materials 0.000 claims description 16
- -1 platinum diamine Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 206010028980 Neoplasm Diseases 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 11
- 208000032839 leukemia Diseases 0.000 description 11
- 201000011510 cancer Diseases 0.000 description 9
- 229910001961 silver nitrate Inorganic materials 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 231100000417 nephrotoxicity Toxicity 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229910021607 Silver chloride Inorganic materials 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 210000003734 kidney Anatomy 0.000 description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 4
- 208000003747 lymphoid leukemia Diseases 0.000 description 4
- 150000003058 platinum compounds Chemical class 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 3
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 201000008228 Ependymoblastoma Diseases 0.000 description 2
- 206010014968 Ependymoma malignant Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 208000029340 primitive neuroectodermal tumor Diseases 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- PJIBBTJBVQZPKJ-UHFFFAOYSA-N 1-trimethylsilylpropane-1-sulfonic acid Chemical compound CCC([Si](C)(C)C)S(O)(=O)=O PJIBBTJBVQZPKJ-UHFFFAOYSA-N 0.000 description 1
- XZVBUSAPGMMCSW-UHFFFAOYSA-L 2-amino-3-methyl-4h-imidazol-5-one;dichloroplatinum Chemical compound Cl[Pt]Cl.CN1CC(=O)N=C1N.CN1CC(=O)N=C1N XZVBUSAPGMMCSW-UHFFFAOYSA-L 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010062237 Renal impairment Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- XZAHJRZBUWYCBM-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1(CN)CCCCC1 XZAHJRZBUWYCBM-UHFFFAOYSA-N 0.000 description 1
- PTGRNMGGKQUEGN-UHFFFAOYSA-N [Pt+2].NCC1CCCCC1 Chemical compound [Pt+2].NCC1CCCCC1 PTGRNMGGKQUEGN-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100001095 no nephrotoxicity Toxicity 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8204067A NL8204067A (nl) | 1982-10-21 | 1982-10-21 | Platina-diaminecomplexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een dergelijk platinadiaminecomplex voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188035B true HU188035B (en) | 1986-03-28 |
Family
ID=19840444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU833623A HU188035B (en) | 1982-10-21 | 1983-10-20 | Process for producing new plantinum-diamine complex |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5993091A (sv) |
| KR (1) | KR910002536B1 (sv) |
| AT (1) | AT390610B (sv) |
| AU (1) | AU562964B2 (sv) |
| BE (1) | BE898058A (sv) |
| CA (1) | CA1229618A (sv) |
| CH (1) | CH658244A5 (sv) |
| CS (1) | CS242888B2 (sv) |
| DD (1) | DD217522A5 (sv) |
| DE (1) | DE3337333A1 (sv) |
| DK (2) | DK483083A (sv) |
| ES (1) | ES526670A0 (sv) |
| FI (1) | FI76351C (sv) |
| FR (1) | FR2534907B1 (sv) |
| GB (1) | GB2128615B (sv) |
| GR (1) | GR79652B (sv) |
| HU (1) | HU188035B (sv) |
| IE (1) | IE56124B1 (sv) |
| IT (1) | IT1169858B (sv) |
| LU (1) | LU85054A1 (sv) |
| NL (1) | NL8204067A (sv) |
| NO (1) | NO171276C (sv) |
| NZ (1) | NZ206018A (sv) |
| PH (1) | PH24077A (sv) |
| PT (1) | PT77542B (sv) |
| SE (1) | SE8305783L (sv) |
| YU (1) | YU43554B (sv) |
| ZA (1) | ZA837857B (sv) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4786725A (en) * | 1982-06-28 | 1988-11-22 | Engelhard Corporation | Solubilized platinum (II) complexes |
| US4758588A (en) * | 1983-06-20 | 1988-07-19 | Research Corporation Technologies | Diaminocyclohexane platinum complexes |
| US4661516A (en) * | 1983-06-20 | 1987-04-28 | Research Corporation | Diaminocyclohexane platinum complexes |
| EP0169645A1 (en) * | 1984-06-27 | 1986-01-29 | Johnson Matthey Public Limited Company | Platinum co-ordination compounds |
| DE3432320A1 (de) * | 1984-09-03 | 1986-03-13 | Behringwerke Ag, 3550 Marburg | Cis-platin-komplexe mit einem pentaerythritderivat als liganden, verfahren zu ihrer herstellung und diese verbindungen enthaltendes pharmazeutisches mittel |
| HU193809B (en) * | 1984-09-12 | 1987-12-28 | Chugai Pharmaceutical Co Ltd | Process for producing new platinum complexes |
| US4737589A (en) * | 1985-08-27 | 1988-04-12 | Nippon Kayaku Kabushiki Kaisha | Platinum Complexes |
| US4760157A (en) * | 1986-01-31 | 1988-07-26 | American Cyanamid Company | (2,2,-bis(aminomethyl)-1,3-propanediol-N,N')platinum complexes |
| US4880790A (en) * | 1986-01-31 | 1989-11-14 | American Cyanamid Company | (Gem-heterocyclodimethanamine-N,N')platinum complexes |
| DE3630497A1 (de) * | 1986-09-08 | 1988-03-10 | Behringwerke Ag | Cis-platin-komplexe, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel |
| EP0262498B1 (de) * | 1986-10-03 | 1990-05-30 | ASTA Pharma Aktiengesellschaft | Diamin-platin (II)-Komplexverbindungen mit einem hydroxylierten 2-Phenyl-Indolring |
| JPS63203692A (ja) * | 1987-02-19 | 1988-08-23 | Nippon Kayaku Co Ltd | 新規白金錯体 |
| AT390065B (de) * | 1987-10-08 | 1990-03-12 | Behringwerke Ag | Cis-platin-komplexe, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel |
| NL8802150A (nl) * | 1988-08-31 | 1990-03-16 | Tno | Platina-(ii)-diaminecomplex, werkwijze voor het bereiden van deze verbinding, preparaat met anti-tumor werking, dat deze verbinding bevat, alsmede gevormde preparaten met anti-tumor werking. |
| NL8802149A (nl) * | 1988-08-31 | 1990-03-16 | Tno | Platina-(iv)diaminecomplex, werkwijze voor het bereiden van deze verbinding, preparaat met anti-tumor werking, dat ten minste een platinaverbinding bevat, alsmede gevormde preparaten met anti-tumor werking. |
| CN102924528B (zh) * | 2012-10-29 | 2015-04-15 | 东南大学 | 抗肿瘤二价铂配合物以及该配合物和其配体的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115418A (en) * | 1976-09-02 | 1978-09-19 | Government Of The United States Of America | 1,2-diaminocyclohexane platinum (ii) complexes having antineoplastic activity |
| US4206226A (en) * | 1977-08-29 | 1980-06-03 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Use of 4-carboxy-phthalato-(1,2-diaminocyclohexane)-platinum(II) and alkali metal salts thereof in alleviating L1210 murine leukemia |
| NL189358C (nl) * | 1978-07-06 | 1993-03-16 | Tno | Werkwijze voor het bereiden van een geneesmiddel voor de behandeling van kanker, alsmede een van een 1,3-alkaandiamine afgeleid platina-diamminecomplex. |
| NL7807334A (nl) * | 1978-07-06 | 1980-01-08 | Tno | Platina-diaminecomplexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een genees- middel met toepassing van een dergelijk platina-dia- minecomplex voor de behandeling van kanker, alsmede al- dus verkregen gevormd geneesmiddel. |
| US4322362A (en) * | 1980-07-28 | 1982-03-30 | Bristol-Myers Company | Salts of 2-hydroxymalonate platinum complexes |
| AU538863B2 (en) * | 1980-05-27 | 1984-08-30 | Bristol-Myers Company | Platinum complex salts have anti-tumor property |
-
1982
- 1982-10-21 NL NL8204067A patent/NL8204067A/nl not_active Application Discontinuation
-
1983
- 1983-10-13 DE DE19833337333 patent/DE3337333A1/de not_active Ceased
- 1983-10-18 AU AU20275/83A patent/AU562964B2/en not_active Ceased
- 1983-10-19 IT IT23359/83A patent/IT1169858B/it active
- 1983-10-19 CA CA000439308A patent/CA1229618A/en not_active Expired
- 1983-10-20 CH CH5718/83A patent/CH658244A5/de not_active IP Right Cessation
- 1983-10-20 FR FR8316715A patent/FR2534907B1/fr not_active Expired
- 1983-10-20 FI FI833842A patent/FI76351C/sv not_active IP Right Cessation
- 1983-10-20 GR GR72754A patent/GR79652B/el unknown
- 1983-10-20 AT AT0373083A patent/AT390610B/de not_active IP Right Cessation
- 1983-10-20 DD DD83255826A patent/DD217522A5/de not_active IP Right Cessation
- 1983-10-20 YU YU2107/83A patent/YU43554B/xx unknown
- 1983-10-20 PT PT77542A patent/PT77542B/pt unknown
- 1983-10-20 LU LU85054A patent/LU85054A1/xx unknown
- 1983-10-20 HU HU833623A patent/HU188035B/hu not_active IP Right Cessation
- 1983-10-20 GB GB08328084A patent/GB2128615B/en not_active Expired
- 1983-10-20 SE SE8305783A patent/SE8305783L/sv not_active Application Discontinuation
- 1983-10-20 NO NO833825A patent/NO171276C/no unknown
- 1983-10-20 DK DK483083A patent/DK483083A/da not_active Application Discontinuation
- 1983-10-20 IE IE2459/83A patent/IE56124B1/en not_active IP Right Cessation
- 1983-10-20 NZ NZ206018A patent/NZ206018A/en unknown
- 1983-10-21 BE BE0/211755A patent/BE898058A/nl not_active IP Right Cessation
- 1983-10-21 JP JP58196286A patent/JPS5993091A/ja active Granted
- 1983-10-21 PH PH29726A patent/PH24077A/en unknown
- 1983-10-21 CS CS837752A patent/CS242888B2/cs unknown
- 1983-10-21 KR KR1019830004987A patent/KR910002536B1/ko not_active IP Right Cessation
- 1983-10-21 ZA ZA837857A patent/ZA837857B/xx unknown
- 1983-10-21 ES ES526670A patent/ES526670A0/es active Granted
-
1992
- 1992-06-09 DK DK075592A patent/DK75592A/da not_active Application Discontinuation
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