DK168666B1 - 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidinderivater, fremgangsmåde til deres fremstilling samt farmaceutiske præparater indeholdende disse - Google Patents
5,6,7,8-tetrahydropyrido[2,3-d]pyrimidinderivater, fremgangsmåde til deres fremstilling samt farmaceutiske præparater indeholdende disse Download PDFInfo
- Publication number
- DK168666B1 DK168666B1 DK472186A DK472186A DK168666B1 DK 168666 B1 DK168666 B1 DK 168666B1 DK 472186 A DK472186 A DK 472186A DK 472186 A DK472186 A DK 472186A DK 168666 B1 DK168666 B1 DK 168666B1
- Authority
- DK
- Denmark
- Prior art keywords
- amino
- cyano
- hydroxy
- tetrahydropyrido
- formula
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- RKYBOAKGTWOIFJ-UHFFFAOYSA-N 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine Chemical class C1=NC=C2CCCNC2=N1 RKYBOAKGTWOIFJ-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
- -1 2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido [2,3-d] pyrimidin-6-yl Chemical group 0.000 claims description 32
- 206010028980 Neoplasm Diseases 0.000 claims description 10
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
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- NNQBBVZQFURSBR-UHFFFAOYSA-N 4-[2-(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)ethenyl]benzoic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2C=C1C=CC1=CC=C(C(O)=O)C=C1 NNQBBVZQFURSBR-UHFFFAOYSA-N 0.000 description 1
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- WSEQLMQNPBNMSL-FJXQXJEOSA-N diethyl (2s)-2-aminopentanedioate;hydron;chloride Chemical compound Cl.CCOC(=O)CC[C@H](N)C(=O)OCC WSEQLMQNPBNMSL-FJXQXJEOSA-N 0.000 description 1
- 239000003166 dihydrofolate reductase inhibitor Substances 0.000 description 1
- OZRNSSUDZOLUSN-LBPRGKRZSA-N dihydrofolic acid Chemical compound N=1C=2C(=O)NC(N)=NC=2NCC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OZRNSSUDZOLUSN-LBPRGKRZSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- VGZATOQZANGXEW-UHFFFAOYSA-N ethyl 4-[2-(6-amino-5-cyanopyridin-3-yl)ethenyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C=CC1=CN=C(N)C(C#N)=C1 VGZATOQZANGXEW-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
- 235000008191 folinic acid Nutrition 0.000 description 1
- 239000011672 folinic acid Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000370 gamma-poly(glutamate) polymer Polymers 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960001691 leucovorin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
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- 208000020816 lung neoplasm Diseases 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- 230000010534 mechanism of action Effects 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 239000012452 mother liquor Substances 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- ZUQYQPGYEFBITH-UHFFFAOYSA-N n-[chloro(phenoxy)phosphoryl]aniline Chemical compound C=1C=CC=CC=1OP(=O)(Cl)NC1=CC=CC=C1 ZUQYQPGYEFBITH-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003552 other antineoplastic agent in atc Drugs 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SRADMCLQPRJPPR-UHFFFAOYSA-N tert-butyl 4-[1-[5-cyano-6-(4-nitrophenyl)sulfanylpyridin-3-yl]but-1-en-2-yl]benzoate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1C(CC)=CC(C=C1C#N)=CN=C1SC1=CC=C([N+]([O-])=O)C=C1 SRADMCLQPRJPPR-UHFFFAOYSA-N 0.000 description 1
- WDYIIWBTXZPPLK-UHFFFAOYSA-N tert-butyl 4-[2-(6-amino-5-cyanopyridin-3-yl)ethenyl]benzoate Chemical compound C1=CC(C(=O)OC(C)(C)C)=CC=C1C=CC1=CN=C(N)C(C#N)=C1 WDYIIWBTXZPPLK-UHFFFAOYSA-N 0.000 description 1
- QXQXBZLXIAUIBG-UHFFFAOYSA-N tert-butyl 4-acetylbenzoate Chemical compound CC(=O)C1=CC=C(C(=O)OC(C)(C)C)C=C1 QXQXBZLXIAUIBG-UHFFFAOYSA-N 0.000 description 1
- DUNFNBQQWYQKFE-UHFFFAOYSA-N tert-butyl 4-formylbenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C=O)C=C1 DUNFNBQQWYQKFE-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000005460 tetrahydrofolate Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70962285A | 1985-03-08 | 1985-03-08 | |
| US70962285 | 1985-03-08 | ||
| PCT/US1986/000368 WO1986005181A1 (fr) | 1985-03-08 | 1986-02-24 | DERIVES DE PYRIDO AD2,3-d BDPYRIMIDINE |
| US8600368 | 1986-02-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK472186D0 DK472186D0 (da) | 1986-10-02 |
| DK472186A DK472186A (da) | 1986-12-19 |
| DK168666B1 true DK168666B1 (da) | 1994-05-16 |
Family
ID=24850641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK472186A DK168666B1 (da) | 1985-03-08 | 1986-10-02 | 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidinderivater, fremgangsmåde til deres fremstilling samt farmaceutiske præparater indeholdende disse |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0215063B1 (fr) |
| JP (2) | JPH0822860B2 (fr) |
| KR (1) | KR940002952B1 (fr) |
| CN (1) | CN1016174B (fr) |
| AT (1) | ATE96790T1 (fr) |
| AU (1) | AU578813B2 (fr) |
| CA (1) | CA1276637C (fr) |
| DE (1) | DE3689250T2 (fr) |
| DK (1) | DK168666B1 (fr) |
| EG (1) | EG18371A (fr) |
| ES (2) | ES8704167A1 (fr) |
| GR (1) | GR860592B (fr) |
| HU (1) | HU196202B (fr) |
| IE (1) | IE63653B1 (fr) |
| IL (1) | IL78059A (fr) |
| MX (1) | MX9203357A (fr) |
| NZ (1) | NZ215404A (fr) |
| PH (1) | PH23136A (fr) |
| PT (1) | PT82149B (fr) |
| SU (1) | SU1676449A3 (fr) |
| WO (1) | WO1986005181A1 (fr) |
| ZA (1) | ZA861235B (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ219971A (en) * | 1986-06-06 | 1989-08-29 | Univ Princeton | Tetrahydropyrido (2,3-d pyrimidine derivatives and pharmaceutical compositions |
| IE60038B1 (en) * | 1986-06-30 | 1994-05-18 | Univ Princeton | 4(3H)-oxo-5, 6, 7, 8-tetrahydropyrido-[2, 3-d]pyrimidine derivatives |
| US4818819A (en) * | 1986-10-20 | 1989-04-04 | The Trustees Of Princeton University | Process for the preparation of fused pyridine compounds |
| GB8702758D0 (en) * | 1987-02-06 | 1987-03-11 | Wellcome Found | Treatment of disease |
| AU598093B2 (en) * | 1987-02-07 | 1990-06-14 | Wellcome Foundation Limited, The | Pyridopyrimidines, methods for their preparation and pharmaceutical formulations thereof |
| EP0305667A3 (fr) * | 1987-09-03 | 1989-10-25 | American Cyanamid Company | Procédé de préparation de l'acide 5,10-dideaza (5,6,7,8)-tétrahydrofolique |
| US4895946A (en) * | 1987-10-26 | 1990-01-23 | The Trustees Of Princeton University | Process for the preparation of fused pyridine compounds |
| US4889859A (en) * | 1988-02-05 | 1989-12-26 | The Trustees Of Princeton University | Pyrido[2,3-d]pyrimidine derivatives |
| DK172753B1 (da) * | 1988-05-25 | 1999-06-28 | Lilly Co Eli | N-(5,6,7,8-tetrahydropyrido[2,3--d]pyrimidin-6-yl-alkanoyl)-glutaminsyrederivater, deres anvendelse, farmaceutiske præparat |
| JPH03173890A (ja) * | 1989-09-21 | 1991-07-29 | Takeda Chem Ind Ltd | ピロロ［２，３―ｄ］ピリミジン誘導体，その製造法，用途及び中間体 |
| CA2066898A1 (fr) * | 1991-04-29 | 1992-10-30 | Chuan Shih | Composes pharmaceutiques |
| US5196424A (en) * | 1992-03-24 | 1993-03-23 | Eli Lilly And Company | N-[2-amino-4-substituted[[(pyrrollo or pyrido)[2,3-d]pyrimidinyl]-alkyl]benzoyl]-L-glutamic acids |
| WO1993020075A1 (fr) * | 1992-04-01 | 1993-10-14 | The University Of Sydney | N5-desazapterines substituees en position 8, utilisees comme antifolates |
| ZA932731B (en) * | 1992-04-23 | 1994-10-19 | Lilly Co Eli | Method of treating gar-transformylase-dependent tumors |
| AU4220193A (en) * | 1992-04-29 | 1993-11-29 | Sri International | Deazaaminopterins for treatment of inflammation |
| ATE201877T1 (de) * | 1993-01-29 | 2001-06-15 | Agouron Pharma | Kondensierte heterocyclische glutaminsäurederivate als antiproliferative mittel |
| US5594139A (en) * | 1993-01-29 | 1997-01-14 | Agouron Pharmaceuticals, Inc. | Processes for preparing antiproliferative garft-inhibiting compounds |
| CN1053448C (zh) * | 1994-07-28 | 2000-06-14 | 阿格罗尼制药公司 | 用作抗增殖药物及garft抑制剂的化合物 |
| ATE242253T1 (de) * | 1994-07-28 | 2003-06-15 | Agouron Pharma | Verbindungen die als antiproliferierende mittel und garft inhibitoren verwendbar sind |
| US5831100A (en) * | 1995-06-07 | 1998-11-03 | Agouron Pharmaceuticals, Inc. | Syntheses of optically pure compounds useful as GARFT inhibitors and their intermediates |
| CN1191861C (zh) | 1999-05-24 | 2005-03-09 | 三共株式会社 | 含有抗Fas抗体的药物组合物 |
| AU2009293140A1 (en) | 2008-09-17 | 2010-03-25 | Endocyte, Inc. | Folate receptor binding conjugates of antifolates |
| CN116333411B (zh) * | 2023-05-29 | 2023-08-11 | 石家庄启宏新材料制品有限公司 | 一种阻燃eva保温材料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4512992A (en) * | 1980-06-13 | 1985-04-23 | Burroughs Wellcome Co. | Treatment with dialkoxy pyridopyrimidine compounds |
| US4431805A (en) * | 1981-09-25 | 1984-02-14 | Southern Research Institute | Pyrido[2,3-d]-pyrimidines |
| US4526964A (en) * | 1982-01-11 | 1985-07-02 | Southern Research Institute | 2,4-Diamino-6-(hydroxymethyl)pyrido[2,3-d]pyrimidine |
| US4536575A (en) * | 1982-01-11 | 1985-08-20 | Southern Research Institute | 2-Amino-4(3H)-oxopyrido[2,3-d]pyrimidino |
| US4532241A (en) * | 1982-08-26 | 1985-07-30 | Sri International | 8,10-Dideazaminopterins |
| US4460591A (en) * | 1982-08-26 | 1984-07-17 | Sri International | 8,10-Dideazaminopterins |
| US4432981A (en) * | 1982-11-05 | 1984-02-21 | Sterling Drug Inc. | 2-(Pyridinyl or hydroxyphenyl)-8-substituted pyrido[2,3-d]pyrimidin-5(8H)-ones |
| JPS61500845A (ja) * | 1983-12-27 | 1986-05-01 | エス・ア−ル・アイ・インタ−ナシヨナル | ８，１０―ジデアザミノプテリン及び抗白血病剤組成物 |
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1986
- 1986-02-19 ZA ZA861235A patent/ZA861235B/xx unknown
- 1986-02-24 KR KR1019860700771A patent/KR940002952B1/ko not_active Expired - Fee Related
- 1986-02-24 DE DE86901675T patent/DE3689250T2/de not_active Expired - Fee Related
- 1986-02-24 EP EP86901675A patent/EP0215063B1/fr not_active Expired - Lifetime
- 1986-02-24 WO PCT/US1986/000368 patent/WO1986005181A1/fr not_active Ceased
- 1986-02-24 AU AU55108/86A patent/AU578813B2/en not_active Ceased
- 1986-02-24 JP JP61501296A patent/JPH0822860B2/ja not_active Expired - Fee Related
- 1986-02-24 AT AT86901675T patent/ATE96790T1/de not_active IP Right Cessation
- 1986-02-24 HU HU862011A patent/HU196202B/hu not_active IP Right Cessation
- 1986-03-03 IE IE56186A patent/IE63653B1/en not_active IP Right Cessation
- 1986-03-03 GR GR860592A patent/GR860592B/el unknown
- 1986-03-05 ES ES552684A patent/ES8704167A1/es not_active Expired
- 1986-03-06 EG EG107/86A patent/EG18371A/xx active
- 1986-03-06 IL IL78059A patent/IL78059A/xx unknown
- 1986-03-06 PT PT82149A patent/PT82149B/pt not_active IP Right Cessation
- 1986-03-07 CA CA000503509A patent/CA1276637C/fr not_active Expired - Lifetime
- 1986-03-07 NZ NZ215404A patent/NZ215404A/xx unknown
- 1986-03-07 PH PH33489A patent/PH23136A/en unknown
- 1986-03-08 CN CN86101475A patent/CN1016174B/zh not_active Expired
- 1986-10-02 DK DK472186A patent/DK168666B1/da not_active IP Right Cessation
- 1986-10-31 ES ES557174A patent/ES8801268A1/es not_active Expired
- 1986-11-03 SU SU864028461A patent/SU1676449A3/ru active
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1992
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1995
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