FR2463776A1 - Compositions comprenant des composes de coordination cis et cis-trans du platine - Google Patents
Compositions comprenant des composes de coordination cis et cis-trans du platine Download PDFInfo
- Publication number
- FR2463776A1 FR2463776A1 FR8018265A FR8018265A FR2463776A1 FR 2463776 A1 FR2463776 A1 FR 2463776A1 FR 8018265 A FR8018265 A FR 8018265A FR 8018265 A FR8018265 A FR 8018265A FR 2463776 A1 FR2463776 A1 FR 2463776A1
- Authority
- FR
- France
- Prior art keywords
- amino
- groups
- cis
- platinum
- halogen
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 229910052697 platinum Inorganic materials 0.000 title abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims description 16
- -1 hydroxy, carbonyl Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 6
- NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002577 pseudohalo group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000007928 solubilization Effects 0.000 claims description 3
- 238000005063 solubilization Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 20
- 201000011510 cancer Diseases 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 4
- 230000000259 anti-tumor effect Effects 0.000 abstract description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910019032 PtCl2 Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical group 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000017105 transposition Effects 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 208000007093 Leukemia L1210 Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- WHSUQQAOKWCJRE-UHFFFAOYSA-N [Pt]N Chemical compound [Pt]N WHSUQQAOKWCJRE-UHFFFAOYSA-N 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 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
- 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)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7929442 | 1979-08-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2463776A1 true FR2463776A1 (fr) | 1981-02-27 |
| FR2463776B1 FR2463776B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-03-22 |
Family
ID=10507399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8018265A Granted FR2463776A1 (fr) | 1979-08-23 | 1980-08-21 | Compositions comprenant des composes de coordination cis et cis-trans du platine |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0147926A3 (en) * | 1983-10-21 | 1985-08-07 | Johnson Matthey Public Limited Company | Oral anti-cancer compositions |
| FR2563524A1 (fr) * | 1984-04-25 | 1985-10-31 | Inst Obschei I Neoorganichesko | Complexes mixtes carboxylatoplatine (ii) et procede de preparation desdits complexes |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4533502A (en) * | 1983-02-22 | 1985-08-06 | Rochon Fernande D | Platinum (II) compounds and their preparation |
| DE3490640C2 (de) * | 1984-01-23 | 1990-04-19 | Inst Obschei I Neoorganichesko | Platin (II)-Carboxylatokomplexe und Verfahren zu ihrer Herstellung |
| IL74449A (en) * | 1984-03-01 | 1988-07-31 | Us Commerce | Tetrahalo-1,2-cyclohexane-diamino platinum complexes and anti-neoplastic compositions comprising them |
| GB8416048D0 (en) * | 1984-06-22 | 1984-07-25 | Johnson Matthey Plc | Anti-tumour compounds of platinum |
| US4658047A (en) * | 1985-09-27 | 1987-04-14 | The United States Of America As Represented By The Department Of Health And Human Services | Method of preparing 1,2-diaminocyclohexane tetrachloro platinum (IV) isomers |
| GB8806044D0 (en) * | 1988-03-14 | 1988-04-13 | Johnson Matthey Plc | Platinum coordination compounds |
| GB9105037D0 (en) * | 1991-03-09 | 1991-04-24 | Johnson Matthey Plc | Improvements in chemical compounds |
| JP3492763B2 (ja) | 1994-06-03 | 2004-02-03 | エスエス製薬株式会社 | 白金錯体及びこれを含有する悪性腫瘍治療剤 |
| JPH11513318A (ja) * | 1995-10-06 | 1999-11-16 | ローベルト ボツシユ ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 工具ホルダーを装備した手持ち式工作盤とこれに所属した工具 |
| CZ288406B6 (en) * | 1998-05-27 | 2001-06-13 | Lachema Np | Platinum complex of oxidation number II, process for preparing such complex, the complex functioning as medicament and pharmaceutical composition in which the complex is comprised |
| CZ303156B6 (cs) * | 1999-04-13 | 2012-05-09 | Anormed Inc. | Komplex cisplatiny a zpusob jeho prípravy |
| AU775373B2 (en) | 1999-10-01 | 2004-07-29 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| RU2186068C2 (ru) * | 1999-12-02 | 2002-07-27 | Институт химии и химической технологии СО РАН | Способ очистки цис-дихлороамминизопропиламинплатины (ii) |
| GB0011903D0 (en) * | 2000-05-18 | 2000-07-05 | Astrazeneca Ab | Combination chemotherapy |
| US6894049B1 (en) | 2000-10-04 | 2005-05-17 | Anormed, Inc. | Platinum complexes as antitumor agents |
| WO2005077385A2 (en) | 2004-02-18 | 2005-08-25 | Gpc Biotech Ag | Methods for treating resistant or refractory tumors |
| CA2573762A1 (en) * | 2004-07-14 | 2006-02-23 | Gpc Biotech Ag | Variable-dose packaging system |
| RU2323886C2 (ru) * | 2006-03-27 | 2008-05-10 | Институт химии и химической технологии СО РАН (ИХХТ СО РАН) | Способ получения трихлороамминплатината (ii) калия или аммония из тетрахлороплатината (ii) калия |
| RU2309158C1 (ru) * | 2006-03-27 | 2007-10-27 | Институт химии и химической технологии СО РАН (ИХХТ СО РАН) | Способ получения цис-дихлороамминизопропиламинплатины (ii) |
| US8168662B1 (en) | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8168661B2 (en) * | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8178564B2 (en) * | 2006-11-06 | 2012-05-15 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8173686B2 (en) | 2006-11-06 | 2012-05-08 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US20110033528A1 (en) * | 2009-08-05 | 2011-02-10 | Poniard Pharmaceuticals, Inc. | Stabilized picoplatin oral dosage form |
| TW200916094A (en) * | 2007-06-27 | 2009-04-16 | Poniard Pharmaceuticals Inc | Stabilized picoplatin dosage form |
| US20100260832A1 (en) * | 2007-06-27 | 2010-10-14 | Poniard Pharmaceuticals, Inc. | Combination therapy for ovarian cancer |
| US20100310661A1 (en) * | 2007-07-16 | 2010-12-09 | Poniard Pharmaceuticals, Inc. | Oral formulations for picoplatin |
| CN102014624A (zh) * | 2008-02-08 | 2011-04-13 | 帕纳德制药公司 | 治疗肺癌的吡铂和氨柔比星 |
| RU2380319C1 (ru) * | 2008-10-15 | 2010-01-27 | Институт химии и химической технологии СО РАН (ИХХТ СО РАН) | Способ получения цис-дихлораминэтиламинплатины (ii) |
| RU2421231C1 (ru) * | 2010-03-15 | 2011-06-20 | Учреждение Российской академии наук Институт химии и химической технологии Сибирского отделения РАН (ИХХТ СО РАН) | Способ получения стерилизованной микрокристаллической соли цис-дихлороамминэтиламинплатины (ii) |
| RU2569646C2 (ru) * | 2013-11-28 | 2015-11-27 | Федеральное государственное бюджетное учреждение науки Институт неорганической химии им. А.В. Николаева Сибирского отделения Российской академии наук | Способ получения тетрахлороплатоат (ii)-иона и его солей с натрием, калием или аммонием |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2329485A1 (de) * | 1972-06-08 | 1973-12-20 | Research Corp | Platinkoordinationsverbindungen |
| DE2707934A1 (de) * | 1976-02-26 | 1977-09-01 | Rustenburg Platinum Mines Ltd | Gemische von platin enthaltenden stoffen, insbesondere gemische von platin enthaltenden stoffen zur chemotherapeutischen behandlung von krebs |
| DE2845373A1 (de) * | 1977-10-19 | 1979-04-26 | Johnson Matthey Co Ltd | Platin-verbindung und verfahren zu ihrer herstellung sowie anwendung der verbindung |
-
1980
- 1980-08-20 US US06/179,786 patent/US4329299A/en not_active Expired - Lifetime
- 1980-08-20 GB GB8027080A patent/GB2060615B/en not_active Expired
- 1980-08-20 ZA ZA00805101A patent/ZA805101B/xx unknown
- 1980-08-21 FR FR8018265A patent/FR2463776A1/fr active Granted
- 1980-08-21 CA CA000358754A patent/CA1164882A/en not_active Expired
- 1980-08-22 NL NL8004752A patent/NL8004752A/nl not_active Application Discontinuation
- 1980-08-22 JP JP11575380A patent/JPS5653693A/ja active Pending
- 1980-08-22 DE DE19803031732 patent/DE3031732A1/de active Granted
- 1980-08-22 CH CH634880A patent/CH644516A5/fr not_active IP Right Cessation
- 1980-08-22 BE BE0/201835A patent/BE884886A/fr not_active IP Right Cessation
- 1980-08-25 IT IT12631/80A patent/IT1194947B/it active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2329485A1 (de) * | 1972-06-08 | 1973-12-20 | Research Corp | Platinkoordinationsverbindungen |
| DE2707934A1 (de) * | 1976-02-26 | 1977-09-01 | Rustenburg Platinum Mines Ltd | Gemische von platin enthaltenden stoffen, insbesondere gemische von platin enthaltenden stoffen zur chemotherapeutischen behandlung von krebs |
| DE2845373A1 (de) * | 1977-10-19 | 1979-04-26 | Johnson Matthey Co Ltd | Platin-verbindung und verfahren zu ihrer herstellung sowie anwendung der verbindung |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0147926A3 (en) * | 1983-10-21 | 1985-08-07 | Johnson Matthey Public Limited Company | Oral anti-cancer compositions |
| FR2563524A1 (fr) * | 1984-04-25 | 1985-10-31 | Inst Obschei I Neoorganichesko | Complexes mixtes carboxylatoplatine (ii) et procede de preparation desdits complexes |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1164882A (en) | 1984-04-03 |
| IT8012631A0 (it) | 1980-08-25 |
| DE3031732C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-10-29 |
| US4329299A (en) | 1982-05-11 |
| GB2060615B (en) | 1983-06-22 |
| DE3031732A1 (de) | 1981-03-12 |
| JPS5653693A (en) | 1981-05-13 |
| IT1194947B (it) | 1988-09-28 |
| GB2060615A (en) | 1981-05-07 |
| ZA805101B (en) | 1981-08-26 |
| BE884886A (fr) | 1980-12-16 |
| FR2463776B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-03-22 |
| CH644516A5 (fr) | 1984-08-15 |
| NL8004752A (nl) | 1981-02-25 |
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