FI69849C - Foerfarande foer framstaellning av nya oxazafosforin-4-tio-alkansulfonsyror och deras neutrala salter - Google Patents
Foerfarande foer framstaellning av nya oxazafosforin-4-tio-alkansulfonsyror och deras neutrala salter Download PDFInfo
- Publication number
- FI69849C FI69849C FI821021A FI821021A FI69849C FI 69849 C FI69849 C FI 69849C FI 821021 A FI821021 A FI 821021A FI 821021 A FI821021 A FI 821021A FI 69849 C FI69849 C FI 69849C
- Authority
- FI
- Finland
- Prior art keywords
- cation
- hydrogen
- formula
- chloroethyl
- oxazaphosphorin
- Prior art date
Links
- 241000277284 Salvelinus fontinalis Species 0.000 title 1
- 150000001768 cations Chemical class 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 2-methanesulfonyloxyethyl Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 3
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
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- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
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- LRIMZGPWMZRRNL-UHFFFAOYSA-N cyclohexanamine;3-sulfanylpropane-1-sulfonic acid Chemical compound [NH3+]C1CCCCC1.[O-]S(=O)(=O)CCCS LRIMZGPWMZRRNL-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- MFFFLTFYDPAEMX-UHFFFAOYSA-M lithium;2-sulfanylethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)CCS MFFFLTFYDPAEMX-UHFFFAOYSA-M 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- ODCRXSAVEXGPAA-UHFFFAOYSA-L magnesium;2-[[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-yl]sulfanyl]ethanesulfonate Chemical compound [Mg+2].[O-]S(=O)(=O)CCSC1CCOP(=O)(N(CCCl)CCCl)N1.[O-]S(=O)(=O)CCSC1CCOP(=O)(N(CCCl)CCCl)N1 ODCRXSAVEXGPAA-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HHWSNFZZGOJQCT-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-(2-hydroxysulfonothioylethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound OS(=O)(=S)CCC1CCOP(=O)(N(CCCl)CCCl)N1 HHWSNFZZGOJQCT-UHFFFAOYSA-N 0.000 description 1
- WBVDYFWHGAIKCG-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-ethoxy-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound CCOC1CCOP(=O)(N(CCCl)CCCl)N1 WBVDYFWHGAIKCG-UHFFFAOYSA-N 0.000 description 1
- SYTRPFOIUVLVTB-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-methoxy-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound COC1CCOP(=O)(N(CCCl)CCCl)N1 SYTRPFOIUVLVTB-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000065 noncytotoxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229930010796 primary metabolite Natural products 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VSOPDDIBJHHIBT-UHFFFAOYSA-M sodium;3-[[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-yl]sulfanyl]propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCSC1CCOP(=O)(N(CCCl)CCCl)N1 VSOPDDIBJHHIBT-UHFFFAOYSA-M 0.000 description 1
- PXRGAUOLIWDZSW-UHFFFAOYSA-M sodium;6-sulfanylhexane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCCCCS PXRGAUOLIWDZSW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- XHJZXCYPSJOWPV-UHFFFAOYSA-N sulfanyl ethanesulfonate Chemical compound CCS(=O)(=O)OS XHJZXCYPSJOWPV-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 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
- C07F9/6584—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 having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
- C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
-
- 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)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3111428 | 1981-03-24 | ||
| DE19813111428 DE3111428A1 (de) | 1981-03-24 | 1981-03-24 | Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI821021A0 FI821021A0 (fi) | 1982-03-23 |
| FI821021L FI821021L (fi) | 1982-09-25 |
| FI69849B FI69849B (fi) | 1985-12-31 |
| FI69849C true FI69849C (fi) | 1986-05-26 |
Family
ID=6128090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI821021A FI69849C (fi) | 1981-03-24 | 1982-03-23 | Foerfarande foer framstaellning av nya oxazafosforin-4-tio-alkansulfonsyror och deras neutrala salter |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US4623742A (nl) |
| JP (1) | JPS57169496A (nl) |
| AT (1) | AT381317B (nl) |
| AU (1) | AU544493B2 (nl) |
| BE (1) | BE892589A (nl) |
| BG (1) | BG38489A3 (nl) |
| CA (1) | CA1194479A (nl) |
| CH (1) | CH648852A5 (nl) |
| DD (1) | DD201799A5 (nl) |
| DE (1) | DE3111428A1 (nl) |
| DK (1) | DK171843B1 (nl) |
| EG (1) | EG15703A (nl) |
| ES (1) | ES8303440A1 (nl) |
| FI (1) | FI69849C (nl) |
| FR (1) | FR2502626B1 (nl) |
| GB (1) | GB2095256B (nl) |
| GR (1) | GR75533B (nl) |
| HU (1) | HU186915B (nl) |
| IE (1) | IE53054B1 (nl) |
| IL (1) | IL65255A (nl) |
| IT (1) | IT1150499B (nl) |
| LU (1) | LU84032A1 (nl) |
| NL (1) | NL192741C (nl) |
| NO (1) | NO163692C (nl) |
| PL (1) | PL129426B1 (nl) |
| PT (1) | PT74641B (nl) |
| RO (1) | RO84661B (nl) |
| SE (1) | SE452159B (nl) |
| SU (1) | SU1318167A3 (nl) |
| YU (1) | YU61582A (nl) |
| ZA (1) | ZA821637B (nl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3111428A1 (de) * | 1981-03-24 | 1982-10-07 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| DE3279834D1 (en) * | 1981-12-31 | 1989-08-31 | Asta Pharma Ag | 4-sulfido-oxaza phosphorines and their use in the treatment of cancer, and in immunosuppression |
| ZA851062B (en) * | 1984-03-01 | 1985-11-27 | Asta Werke Ag Chem Fab | Salts of oxazaphosphorine derivatives and process for their production |
| DE3569737D1 (en) * | 1984-03-01 | 1989-06-01 | Asta Pharma Ag | Salts of oxazaphosphorine derivatives |
| DE3415726A1 (de) * | 1984-04-27 | 1985-10-31 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Verfahren zur herstellung von in 4-stellung substituierten oxazaphosphorin-derivaten |
| FR2567129B1 (fr) * | 1984-07-06 | 1986-12-05 | Adir | Nouveaux derives de l'oxaazaphosphorine, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| US5204335A (en) * | 1986-10-31 | 1993-04-20 | Asta Pharma Aktiengesellschaft | Ifosfamide lyophilisate and process for its preparation |
| ES2040394T3 (es) * | 1988-03-19 | 1993-10-16 | Asta Medica Aktiengesellschaft | Procedimiento para preparar un material liofilizado de ifosfamida y mesna. |
| US5190929A (en) * | 1988-05-25 | 1993-03-02 | Research Corporation Technologies, Inc. | Cyclophosphamide analogs useful as anti-tumor agents |
| RO113611B1 (ro) * | 1990-08-03 | 1998-09-30 | Asta Pharma Ag | Preparate solide de ifosfamida, administrate oral si procedeu de obtinere |
| US5661188A (en) * | 1995-06-07 | 1997-08-26 | Medical Research Foundation and Infrastructure Development for Health Services--Nahariya Hospital Branch | Therapeutic uses for sodium 2-mercaptoethanesulphonate (mesna) |
| US20080223826A1 (en) * | 2007-03-13 | 2008-09-18 | Stephen Mazur | Reagent Delivery using a Membrane-Mediated Process |
| FR2968662B1 (fr) | 2010-12-10 | 2013-11-22 | Roussy Inst Gustave | Nouveaux derives d'oxazaphosphorines pre-activees, utilisation et methode de preparation |
| GB2626789A (en) * | 2023-02-03 | 2024-08-07 | Exactmer Ltd | Deprotection processes and cation scavengers for use in the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2107936C3 (de) * | 1971-02-19 | 1978-06-08 | Asta-Werke Ag Chemische Fabrik, 4800 Bielefeld | Alkylsulfonsäureester von 2-Oxo-13,2-oxazaphosphorinanen und diese enthaltende pharmazeutische Präparate |
| DE1645921C3 (de) * | 1966-07-11 | 1978-10-12 | Asta-Werke Ag Chemische Fabrik, 4800 Bielefeld | 2-Oxo-13,2-osazaphosphorinane, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| DE2201675A1 (de) * | 1972-01-14 | 1973-07-19 | Asta Werke Ag Chem Fab | Alkylsulfonsaeureester 1,3,2-oxazaphospha-cyclischer verbindungen, verfahren zu ihrer herstellung und pharmazeutische praeparate |
| JPS5159886A (nl) * | 1974-11-20 | 1976-05-25 | Shionogi Seiyaku Kk | |
| JPS54157580A (en) | 1978-05-29 | 1979-12-12 | Otsuka Pharmaceut Co Ltd | Optically active oxazaphosphorine derivative |
| JPS5826919B2 (ja) | 1978-11-07 | 1983-06-06 | 大塚製薬株式会社 | シクロ↓−１，３，２↓−オキサアザホスホル誘導体の製造法 |
| JPS55154984A (en) * | 1979-05-24 | 1980-12-02 | Shionogi & Co Ltd | Novel 4-substituted-2h-1,3,2-oxaazaphospholine-2-oxide derivative |
| DE3220672A1 (de) | 1981-03-24 | 1983-12-08 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Cis-oxazaphosphorin-4-thio-alkansulfonsaeuren, ihre neutralen salze, verfahren zur herstellung derselben und diese enthaltenden pharmazeutischen praeparate |
| DE3111428A1 (de) | 1981-03-24 | 1982-10-07 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Oxazaphosphorin-4-thio-alkansulfonsaeuren und deren neutrale salze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| DE3220432A1 (de) | 1981-03-24 | 1983-12-01 | Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld | Oxazaphosphorin-4-thio-alkansulfonsaeure, ihre neutralen salze, verfahren zur herstellung derselben und diese enthaltenden pharmazeutischen praeparate |
-
1981
- 1981-03-24 DE DE19813111428 patent/DE3111428A1/de active Granted
-
1982
- 1982-03-08 CH CH1390/82A patent/CH648852A5/de not_active IP Right Cessation
- 1982-03-09 IE IE531/82A patent/IE53054B1/en unknown
- 1982-03-11 ZA ZA821637A patent/ZA821637B/xx unknown
- 1982-03-12 AU AU81344/82A patent/AU544493B2/en not_active Ceased
- 1982-03-12 GB GB8207375A patent/GB2095256B/en not_active Expired
- 1982-03-15 IL IL65255A patent/IL65255A/xx unknown
- 1982-03-17 AT AT0106382A patent/AT381317B/de not_active IP Right Cessation
- 1982-03-17 GR GR67621A patent/GR75533B/el unknown
- 1982-03-22 FR FR8204823A patent/FR2502626B1/fr not_active Expired
- 1982-03-22 RO RO106989A patent/RO84661B/ro unknown
- 1982-03-22 SE SE8201807A patent/SE452159B/sv not_active IP Right Cessation
- 1982-03-22 YU YU00615/82A patent/YU61582A/xx unknown
- 1982-03-23 CA CA000399098A patent/CA1194479A/en not_active Expired
- 1982-03-23 ES ES510677A patent/ES8303440A1/es not_active Expired
- 1982-03-23 SU SU823414100A patent/SU1318167A3/ru active
- 1982-03-23 IT IT20351/82A patent/IT1150499B/it active
- 1982-03-23 JP JP57044779A patent/JPS57169496A/ja active Granted
- 1982-03-23 PT PT74641A patent/PT74641B/pt unknown
- 1982-03-23 NO NO820957A patent/NO163692C/no not_active IP Right Cessation
- 1982-03-23 DD DD82238374A patent/DD201799A5/de unknown
- 1982-03-23 EG EG82156A patent/EG15703A/xx active
- 1982-03-23 HU HU82879A patent/HU186915B/hu unknown
- 1982-03-23 BE BE2/59642A patent/BE892589A/fr not_active IP Right Cessation
- 1982-03-23 FI FI821021A patent/FI69849C/fi not_active IP Right Cessation
- 1982-03-23 DK DK129882A patent/DK171843B1/da not_active IP Right Cessation
- 1982-03-24 NL NL8201227A patent/NL192741C/nl not_active IP Right Cessation
- 1982-03-24 LU LU84032A patent/LU84032A1/de unknown
- 1982-03-24 BG BG055941A patent/BG38489A3/xx unknown
- 1982-08-24 PL PL1982235606A patent/PL129426B1/pl unknown
-
1984
- 1984-12-19 US US06/683,374 patent/US4623742A/en not_active Expired - Lifetime
-
1988
- 1988-02-02 US US07/149,954 patent/US4929607A/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: ASTA-WERKE AKTIENGESELLSCHAFT CHEMISCHE |