NL8300598A - N-acyl-n-carbamoyloxyureums met anti-neoplastische werking. - Google Patents
N-acyl-n-carbamoyloxyureums met anti-neoplastische werking. Download PDFInfo
- Publication number
- NL8300598A NL8300598A NL8300598A NL8300598A NL8300598A NL 8300598 A NL8300598 A NL 8300598A NL 8300598 A NL8300598 A NL 8300598A NL 8300598 A NL8300598 A NL 8300598A NL 8300598 A NL8300598 A NL 8300598A
- Authority
- NL
- Netherlands
- Prior art keywords
- compounds
- compound
- acetamide
- methylene chloride
- isocyanate
- Prior art date
Links
- 230000000118 anti-neoplastic effect Effects 0.000 title description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
- 208000032839 leukemia Diseases 0.000 claims abstract description 7
- 201000009030 Carcinoma Diseases 0.000 claims abstract description 6
- 230000012010 growth Effects 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
- -1 (1,1-dimethylethyl) aminocarbonyl Chemical group 0.000 description 25
- 239000000203 mixture Substances 0.000 description 20
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 5
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZZRODMXZJNLQGD-UHFFFAOYSA-N ONS(=O)=O Chemical compound ONS(=O)=O ZZRODMXZJNLQGD-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- YKSVNSKYIUPAKW-UHFFFAOYSA-N n-hydroxymethanesulfonamide Chemical compound CS(=O)(=O)NO YKSVNSKYIUPAKW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 210000004885 white matter Anatomy 0.000 description 3
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006748 scratching Methods 0.000 description 2
- 230000002393 scratching effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- MMPOTNFPDMJTRR-UHFFFAOYSA-N OOOOOOOOOOO Chemical compound OOOOOOOOOOO MMPOTNFPDMJTRR-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- CYWMOWCOOYBYKZ-UHFFFAOYSA-N [acetyl(cyclohexylcarbamoyl)amino] n-cyclohexylcarbamate Chemical compound C1CCCCC1NC(=O)N(C(=O)C)OC(=O)NC1CCCCC1 CYWMOWCOOYBYKZ-UHFFFAOYSA-N 0.000 description 1
- JURAJLFHWXNPHG-UHFFFAOYSA-N [acetyl(methylcarbamoyl)amino] n-methylcarbamate Chemical compound CNC(=O)ON(C(C)=O)C(=O)NC JURAJLFHWXNPHG-UHFFFAOYSA-N 0.000 description 1
- FYYNYTLWTNFHAS-UHFFFAOYSA-N [acetyl(propan-2-ylcarbamoyl)amino] n-propan-2-ylcarbamate Chemical compound CC(C)NC(=O)ON(C(C)=O)C(=O)NC(C)C FYYNYTLWTNFHAS-UHFFFAOYSA-N 0.000 description 1
- BSFZTEHBSPCPTF-UHFFFAOYSA-N [benzoyl(propan-2-ylcarbamoyl)amino] n-propan-2-ylcarbamate Chemical compound CC(C)NC(=O)ON(C(=O)NC(C)C)C(=O)C1=CC=CC=C1 BSFZTEHBSPCPTF-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 1
- 229960001171 acetohydroxamic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- JCHMFMSWRWHRFI-HMMYKYKNSA-N ethyl (2e)-2-[(2,5-dichlorophenyl)hydrazinylidene]-2-(2,6-dimethylmorpholin-4-yl)acetate Chemical compound C1C(C)OC(C)CN1/C(C(=O)OCC)=N/NC1=CC(Cl)=CC=C1Cl JCHMFMSWRWHRFI-HMMYKYKNSA-N 0.000 description 1
- LDDOSDVZPSGLFZ-UHFFFAOYSA-N ethyl cyclopropanecarboxylate Chemical compound CCOC(=O)C1CC1 LDDOSDVZPSGLFZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- DFUXHKDPVJEPOX-UHFFFAOYSA-N hydroxycarbamoyl acetate Chemical compound CC(=O)OC(=O)NO DFUXHKDPVJEPOX-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Public Health (AREA)
- Hematology (AREA)
- Oncology (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)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
- Pressure Welding/Diffusion-Bonding (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34950282 | 1982-02-17 | ||
| US06/349,502 US4413009A (en) | 1982-02-17 | 1982-02-17 | N-((Alkylamino)carbonyl)-N-(((alkylamino)carbonyl)oxy)acylamides with antineoplastic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8300598A true NL8300598A (nl) | 1983-09-16 |
Family
ID=23372667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8300598A NL8300598A (nl) | 1982-02-17 | 1983-02-17 | N-acyl-n-carbamoyloxyureums met anti-neoplastische werking. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4413009A (https=) |
| EP (1) | EP0086492B1 (https=) |
| JP (1) | JPS58152858A (https=) |
| AT (2) | AT387962B (https=) |
| BE (1) | BE895923A (https=) |
| CA (1) | CA1196007A (https=) |
| CH (1) | CH653014A5 (https=) |
| DE (2) | DE3305107A1 (https=) |
| FR (1) | FR2521555A1 (https=) |
| GB (1) | GB2115414B (https=) |
| IT (1) | IT1199988B (https=) |
| NL (1) | NL8300598A (https=) |
| SE (1) | SE8300854L (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100228318B1 (ko) * | 1997-03-14 | 1999-11-01 | 윤종용 | 다중 펄스코드 변조데이터 합성회로 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3786088A (en) * | 1968-12-05 | 1974-01-15 | Velsicol Chemical Corp | N,o-dicarbamoyl-n-phenylhydroxylamines |
| US3836572A (en) * | 1973-04-02 | 1974-09-17 | Monsanto Co | Dicarbamoyl hydroxamates |
| US3957867A (en) * | 1973-04-11 | 1976-05-18 | Hercules Incorporated | Certain oximinyl allophanates and their use as herbicides |
| US4030912A (en) * | 1973-04-11 | 1977-06-21 | Hercules Incorporated | Certain oximinyl allophanates and their use as herbicides |
| US4207091A (en) * | 1976-02-09 | 1980-06-10 | Ciba-Geigy Corporation | Method of preventing plants from damage by frost |
-
1982
- 1982-02-17 US US06/349,502 patent/US4413009A/en not_active Expired - Lifetime
-
1983
- 1983-02-14 CH CH811/83A patent/CH653014A5/de not_active IP Right Cessation
- 1983-02-14 CA CA000421553A patent/CA1196007A/en not_active Expired
- 1983-02-14 AT AT0049483A patent/AT387962B/de not_active IP Right Cessation
- 1983-02-15 DE DE19833305107 patent/DE3305107A1/de not_active Withdrawn
- 1983-02-15 JP JP58022245A patent/JPS58152858A/ja active Granted
- 1983-02-15 AT AT83101435T patent/ATE22071T1/de not_active IP Right Cessation
- 1983-02-15 EP EP83101435A patent/EP0086492B1/en not_active Expired
- 1983-02-15 GB GB08304146A patent/GB2115414B/en not_active Expired
- 1983-02-15 DE DE8383101435T patent/DE3365949D1/de not_active Expired
- 1983-02-16 BE BE0/210127A patent/BE895923A/fr not_active IP Right Cessation
- 1983-02-16 IT IT19608/83A patent/IT1199988B/it active
- 1983-02-16 SE SE8300854A patent/SE8300854L/xx not_active Application Discontinuation
- 1983-02-17 NL NL8300598A patent/NL8300598A/nl not_active Application Discontinuation
- 1983-02-17 FR FR8302605A patent/FR2521555A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1196007A (en) | 1985-10-29 |
| IT8319608A0 (it) | 1983-02-16 |
| EP0086492B1 (en) | 1986-09-10 |
| FR2521555B1 (https=) | 1985-05-17 |
| DE3365949D1 (en) | 1986-10-16 |
| US4413009A (en) | 1983-11-01 |
| DE3305107A1 (de) | 1983-08-18 |
| EP0086492A2 (en) | 1983-08-24 |
| GB2115414A (en) | 1983-09-07 |
| GB8304146D0 (en) | 1983-03-16 |
| GB2115414B (en) | 1985-09-18 |
| CH653014A5 (de) | 1985-12-13 |
| SE8300854L (sv) | 1983-08-18 |
| JPH0359898B2 (https=) | 1991-09-12 |
| ATE22071T1 (de) | 1986-09-15 |
| AT387962B (de) | 1989-04-10 |
| BE895923A (fr) | 1983-08-16 |
| FR2521555A1 (fr) | 1983-08-19 |
| ATA49483A (de) | 1988-09-15 |
| IT1199988B (it) | 1989-01-05 |
| JPS58152858A (ja) | 1983-09-10 |
| SE8300854D0 (sv) | 1983-02-16 |
| EP0086492A3 (en) | 1984-06-06 |
| IT8319608A1 (it) | 1984-08-16 |
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