HU189371B - Process for production of new triciclophosphasene derivates and pharmaceutical preparations containing them as active agents - Google Patents
Process for production of new triciclophosphasene derivates and pharmaceutical preparations containing them as active agents Download PDFInfo
- Publication number
- HU189371B HU189371B HU834053A HU405383A HU189371B HU 189371 B HU189371 B HU 189371B HU 834053 A HU834053 A HU 834053A HU 405383 A HU405383 A HU 405383A HU 189371 B HU189371 B HU 189371B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- injection
- spirodiam
- reacting
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000008569 process Effects 0.000 title claims abstract description 14
- 239000013543 active substance Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 8
- 230000000259 anti-tumor effect Effects 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical group CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005700 Putrescine Substances 0.000 claims description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- -1 1-aziridinyl Chemical group 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract 1
- 238000002347 injection Methods 0.000 description 50
- 239000007924 injection Substances 0.000 description 50
- 206010028980 Neoplasm Diseases 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- IQMLWPPOVFMTOU-UHFFFAOYSA-N 1,3,3,5,5-pentakis(aziridin-1-yl)-1$l^{6}-thia-2,4,6-triaza-3$l^{5},5$l^{5}-diphosphacyclohexa-1,3,5-triene 1-oxide Chemical compound N=1S(=O)(N2CC2)=NP(N2CC2)(N2CC2)=NP=1(N1CC1)N1CC1 IQMLWPPOVFMTOU-UHFFFAOYSA-N 0.000 description 7
- PXZAWHSJYIECNQ-UHFFFAOYSA-N apholate Chemical compound C1CN1P1(N2CC2)=NP(N2CC2)(N2CC2)=NP(N2CC2)(N2CC2)=N1 PXZAWHSJYIECNQ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 231100001274 therapeutic index Toxicity 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000007972 injectable composition Substances 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 201000006512 mast cell neoplasm Diseases 0.000 description 2
- 208000006971 mastocytoma Diseases 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 201000008228 Ependymoblastoma Diseases 0.000 description 1
- 206010014968 Ependymoma malignant Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 208000009916 Yoshida Sarcoma Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940121657 clinical drug Drugs 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 201000002313 intestinal cancer Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100001160 nonlethal Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000029340 primitive neuroectodermal tumor Diseases 0.000 description 1
- FHEWYCSXRQZLOJ-UHFFFAOYSA-N prop-1-ene;dihydrochloride Chemical compound Cl.Cl.CC=C FHEWYCSXRQZLOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- 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)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8219768A FR2536751B1 (fr) | 1982-11-25 | 1982-11-25 | Nouveaux derives de tricyclophosphazenes, procede pour leur preparation et leur application en tant que medicament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT34038A HUT34038A (en) | 1985-01-28 |
| HU189371B true HU189371B (en) | 1986-06-30 |
Family
ID=9279519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU834053A HU189371B (en) | 1982-11-25 | 1983-11-25 | Process for production of new triciclophosphasene derivates and pharmaceutical preparations containing them as active agents |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4595682A (https=) |
| EP (1) | EP0112743B1 (https=) |
| JP (1) | JPS59108794A (https=) |
| AT (1) | ATE25849T1 (https=) |
| CA (1) | CA1244455A (https=) |
| DE (1) | DE3370157D1 (https=) |
| FR (1) | FR2536751B1 (https=) |
| HU (1) | HU189371B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2595360B1 (fr) * | 1986-03-06 | 1988-07-01 | Centre Nat Rech Scient | Composes du type cyclophosphazene, procede de preparation et composition pharmaceutique les contenant |
| FR2642427B1 (fr) * | 1989-01-31 | 1991-08-30 | Pf Medicament | Procede de preparation diazo spiro cyclotriphosphazenes |
| FR2643080B1 (fr) * | 1989-02-10 | 1991-09-13 | Centre Nat Rech Scient | Composes oxodiaminocyclotriphosphazenes, leur preparation et leurs applications |
| FR2668152B1 (fr) * | 1990-10-23 | 1994-05-27 | Pf Medicament | Derives n,o spirocycliques de cyclotriphosphazenes, leur preparation et leur application en therapeutique. |
| FR2705347A1 (fr) * | 1993-05-18 | 1994-11-25 | Pf Medicament | Nouveaux dérivés d'aziridino spirooxaazaalkylcyclotriphosphazènes substitués, leur procédé de préparation et leur application en tant que médicament. |
| FR2706463A1 (fr) * | 1993-06-15 | 1994-12-23 | Pf Medicament | Nouveaux dérivés d'aziridino spirodiazaalkylcyclotriphosphazènes substitués leur procédé de préparation et leur utilisation en tant que médicament. |
| FR2706464A1 (fr) * | 1993-06-18 | 1994-12-23 | Pf Medicament | Nouveaux dérivés de spirodiaza ou spirooxaaza alkylcyclotriphosphazènes substitués par des méthyl ou diméthyl aziridines, leur préparation et leur utilisation en tant que médicament. |
| US5451637A (en) * | 1994-05-10 | 1995-09-19 | Hercules Incorporated | Organosilicon compositions prepared from unsaturated elastomeric polymers |
| KR100363394B1 (ko) * | 2000-08-21 | 2002-12-05 | 한국과학기술연구원 | 온도감응성을 갖는 포스파젠삼량체-백금착물 복합체, 그의제조방법 및 그를 함유하는 항암제 조성물 |
| CN102171338B (zh) | 2008-10-10 | 2014-08-13 | 东洋纺织株式会社 | 具有果糖基缬氨酰基组氨酸氧化酶活性的蛋白质及其修饰产物以及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3311622A (en) * | 1961-05-17 | 1967-03-28 | Shulton Inc | Substituted phosphonitrilic trimers |
| US3197464A (en) * | 1962-05-18 | 1965-07-27 | Olin Mathieson | Aziridinyl phosphonitriles |
| US3299128A (en) * | 1964-07-10 | 1967-01-17 | American Cyanamid Co | Substituted cyclic phosphonitrilic compounds and methods of preparing same |
| FR2104915A1 (en) * | 1970-09-04 | 1972-04-28 | Inst Im Ordzho Ik | Cyclotriphosphazatriene derivs - with cytostatic activity |
| FR2460303A1 (fr) * | 1979-07-04 | 1981-01-23 | Anvar | Nouveaux composes a cycle inorganique utiles comme medicaments et procede pour leur preparation |
| NL8007107A (nl) * | 1980-12-30 | 1982-07-16 | Rijksuniversiteit Broerstraat | Fosfazeengroep bevattend ringsysteem of een door aminolyse daaruit bereide verbinding, alsmede werkwijze ter bereiding van een onvolledig door een aminozuurderivaat, in het bijzonder glycinederivaat, gesubstitueerd fosfazeenringsysteem of fosfazeenachtig ringsysteem. |
-
1982
- 1982-11-25 FR FR8219768A patent/FR2536751B1/fr not_active Expired
-
1983
- 1983-11-23 DE DE8383402256T patent/DE3370157D1/de not_active Expired
- 1983-11-23 AT AT83402256T patent/ATE25849T1/de not_active IP Right Cessation
- 1983-11-23 US US06/554,812 patent/US4595682A/en not_active Expired - Fee Related
- 1983-11-23 EP EP83402256A patent/EP0112743B1/fr not_active Expired
- 1983-11-24 CA CA000441842A patent/CA1244455A/fr not_active Expired
- 1983-11-25 HU HU834053A patent/HU189371B/hu not_active IP Right Cessation
- 1983-11-25 JP JP58221952A patent/JPS59108794A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0112743B1 (fr) | 1987-03-11 |
| CA1244455A (fr) | 1988-11-08 |
| DE3370157D1 (en) | 1987-04-16 |
| JPH0410474B2 (https=) | 1992-02-25 |
| FR2536751A1 (fr) | 1984-06-01 |
| FR2536751B1 (fr) | 1986-04-25 |
| HUT34038A (en) | 1985-01-28 |
| ATE25849T1 (de) | 1987-03-15 |
| JPS59108794A (ja) | 1984-06-23 |
| US4595682A (en) | 1986-06-17 |
| EP0112743A1 (fr) | 1984-07-04 |
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