DD152126A5 - Verfahren zur herstellung von neuen 1-substituierten-3-cycloalkyl-sulfonyl-pyrrolidin-2,5-dion-derivaten - Google Patents
Verfahren zur herstellung von neuen 1-substituierten-3-cycloalkyl-sulfonyl-pyrrolidin-2,5-dion-derivaten Download PDFInfo
- Publication number
- DD152126A5 DD152126A5 DD80222669A DD22266980A DD152126A5 DD 152126 A5 DD152126 A5 DD 152126A5 DD 80222669 A DD80222669 A DD 80222669A DD 22266980 A DD22266980 A DD 22266980A DD 152126 A5 DD152126 A5 DD 152126A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dione
- general formula
- pyrrolidine
- sulfonyl
- items
- Prior art date
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- 229920004518 DION® Polymers 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 53
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- FIVIUAMQNIPFDP-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-phenylpyrrolidine-2,5-dione Chemical compound O=C1CC(S(=O)(=O)C2CCCCC2)C(=O)N1C1=CC=CC=C1 FIVIUAMQNIPFDP-UHFFFAOYSA-N 0.000 claims abstract description 4
- CBJXGRDZASYPAO-UHFFFAOYSA-N 3-cyclohexylsulfonylpyrrolidine-2,5-dione Chemical compound O=C1NC(=O)CC1S(=O)(=O)C1CCCCC1 CBJXGRDZASYPAO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 46
- -1 substituted Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical class N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000007259 addition reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- FDAMVVHYWSPPFN-UHFFFAOYSA-N 2-sulfonylpyrrolidine Chemical compound O=S(=O)=C1CCCN1 FDAMVVHYWSPPFN-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 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 group [H]* 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 2
- VNAPSENBXNLIGX-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-cyclohexylsulfonylpyrrolidine-2,5-dione Chemical compound C1=CC(C(=O)C)=CC=C1N1C(=O)C(S(=O)(=O)C2CCCCC2)CC1=O VNAPSENBXNLIGX-UHFFFAOYSA-N 0.000 claims 1
- PWDJKOYIEUMHDJ-UHFFFAOYSA-N 1-cyclohexylsulfonylpyrrolidine Chemical compound C1CCCN1S(=O)(=O)C1CCCCC1 PWDJKOYIEUMHDJ-UHFFFAOYSA-N 0.000 claims 1
- RLRVJYLDFJCQLT-UHFFFAOYSA-N 2-(3-cyclohexylsulfonyl-2,5-dioxopyrrolidin-1-yl)-5-methylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(C)=CC=C1N1C(=O)C(S(=O)(=O)C2CCCCC2)CC1=O RLRVJYLDFJCQLT-UHFFFAOYSA-N 0.000 claims 1
- YEUSKMIQJAFXJZ-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-(3-nitrophenyl)pyrrolidine-2,5-dione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(C(CC2=O)S(=O)(=O)C2CCCCC2)=O)=C1 YEUSKMIQJAFXJZ-UHFFFAOYSA-N 0.000 claims 1
- WFZNBGHXOYVLEK-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-(4-methoxyphenyl)pyrrolidine-2,5-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(S(=O)(=O)C2CCCCC2)CC1=O WFZNBGHXOYVLEK-UHFFFAOYSA-N 0.000 claims 1
- XLUNTZPRMGONDA-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-ethylpyrrolidine-2,5-dione Chemical compound O=C1N(CC)C(=O)CC1S(=O)(=O)C1CCCCC1 XLUNTZPRMGONDA-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
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- 239000011630 iodine Chemical group 0.000 claims 1
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- CFTUCNOBCOZZLE-UHFFFAOYSA-N 1-(1-phenylcyclohexyl)sulfonylpyrrolidine-2,5-dione Chemical compound C1(=CC=CC=C1)C1(CCCCC1)S(=O)(=O)N1C(CCC1=O)=O CFTUCNOBCOZZLE-UHFFFAOYSA-N 0.000 description 1
- CGHHKCYQBCFICS-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-cyclohexylsulfonylpyrrolidine-2,5-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C(S(=O)(=O)C2CCCCC2)CC1=O CGHHKCYQBCFICS-UHFFFAOYSA-N 0.000 description 1
- UKAKAZFRAZNYDY-UHFFFAOYSA-N 1-benzyl-3-cyclohexylsulfonylpyrrolidine-2,5-dione Chemical compound O=C1CC(S(=O)(=O)C2CCCCC2)C(=O)N1CC1=CC=CC=C1 UKAKAZFRAZNYDY-UHFFFAOYSA-N 0.000 description 1
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- OSIAJEVAIYCZCF-UHFFFAOYSA-N 2-acetyloxy-4-(2,5-dioxopyrrolidin-1-yl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC(N2C(CCC2=O)=O)=C1 OSIAJEVAIYCZCF-UHFFFAOYSA-N 0.000 description 1
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- MHPQBXCHLCDQBU-UHFFFAOYSA-N 3-cyclohexylsulfanylpyrrolidine-2,5-dione Chemical compound O=C1NC(=O)CC1SC1CCCCC1 MHPQBXCHLCDQBU-UHFFFAOYSA-N 0.000 description 1
- ROPDHOFDWRERBT-UHFFFAOYSA-N 3-cyclopentylsulfonyl-1-(4-methylphenyl)pyrrolidine-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C(S(=O)(=O)C2CCCC2)CC1=O ROPDHOFDWRERBT-UHFFFAOYSA-N 0.000 description 1
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79CI1951A HU178455B (en) | 1979-07-17 | 1979-07-17 | Process for producing new 1-substituted-3-cycloalkyl-sulfonyl-pyrrolidine-2,5-dione derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD152126A5 true DD152126A5 (de) | 1981-11-18 |
Family
ID=10994755
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80222669A DD152126A5 (de) | 1979-07-17 | 1980-07-16 | Verfahren zur herstellung von neuen 1-substituierten-3-cycloalkyl-sulfonyl-pyrrolidin-2,5-dion-derivaten |
| DD80227898A DD156562A5 (de) | 1979-07-17 | 1980-07-16 | Fungizide mittel |
| DD80227899A DD156572A5 (de) | 1979-07-17 | 1980-07-16 | Verfahren zur herstellung von fungiziden pharmazeutischen praeparaten |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80227898A DD156562A5 (de) | 1979-07-17 | 1980-07-16 | Fungizide mittel |
| DD80227899A DD156572A5 (de) | 1979-07-17 | 1980-07-16 | Verfahren zur herstellung von fungiziden pharmazeutischen praeparaten |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4364958A (no) |
| JP (1) | JPS5639067A (no) |
| AT (1) | AT374177B (no) |
| AU (1) | AU535388B2 (no) |
| BE (1) | BE884353A (no) |
| CA (1) | CA1135707A (no) |
| CH (1) | CH651296A5 (no) |
| CS (1) | CS226015B2 (no) |
| DD (3) | DD152126A5 (no) |
| DE (1) | DE3026755A1 (no) |
| DK (1) | DK159418C (no) |
| ES (1) | ES8106141A1 (no) |
| FI (1) | FI74948C (no) |
| FR (1) | FR2461700A1 (no) |
| GB (1) | GB2054589B (no) |
| GR (1) | GR69590B (no) |
| HU (1) | HU178455B (no) |
| IL (1) | IL60612A (no) |
| IN (1) | IN151488B (no) |
| IT (1) | IT1141606B (no) |
| LU (1) | LU82636A1 (no) |
| NL (1) | NL8004093A (no) |
| NO (1) | NO154493C (no) |
| PL (4) | PL127255B1 (no) |
| SE (1) | SE450831B (no) |
| SU (5) | SU1007555A3 (no) |
| YU (1) | YU41935B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3637507A1 (de) * | 1986-11-04 | 1988-05-05 | Bayer Ag | Neues verfahren zur herstellung von teilweise neuen 3-sulfenylmaleinimiden und ihre verwendung |
| DE3719764A1 (de) * | 1987-06-13 | 1988-12-22 | Bayer Ag | Ionenaustauscherharze beladen mit chinoloncarbonsaeurederivaten, ihre herstellung und verwendung |
| AU9318498A (en) * | 1997-09-18 | 1999-04-05 | Pierce Chemical Company | Sulfo-n-hydroxy succinimide and method of preparation |
| US5892057A (en) | 1997-09-18 | 1999-04-06 | Pierce Chemical Company | Preparation of sulfo-N-hydroxysuccinimide salts |
| US6420415B1 (en) | 1998-09-21 | 2002-07-16 | Takeda Chemical Industries, Ltd. | Thiol compounds, their production and use |
| HU226421B1 (en) * | 1998-11-09 | 2008-12-29 | Sanofi Aventis | Process for racemizing optically active 2-(2-chlorophenyl)-2-(2-(2-thienyl)-ethylamino)-acetamides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538114A (en) * | 1966-08-12 | 1970-11-03 | Basf Ag | N-(substituted-phenyl)-succinimides |
| GB1319772A (en) * | 1969-06-18 | 1973-06-06 | Geistlich Soehne Ag | Succinimides |
| CA950916A (en) * | 1970-09-04 | 1974-07-09 | Shigehiro Ooba | N-phenylsuccinimide derivatives |
| US3804856A (en) * | 1970-09-04 | 1974-04-16 | Sumitomo Chemical Co | N-phenylsuccinimides |
| JPS4833025A (no) * | 1971-08-28 | 1973-05-07 | ||
| JPS5412904B2 (no) * | 1973-05-18 | 1979-05-26 |
-
1979
- 1979-07-17 HU HU79CI1951A patent/HU178455B/hu not_active IP Right Cessation
-
1980
- 1980-07-15 DE DE19803026755 patent/DE3026755A1/de active Granted
- 1980-07-16 NL NL8004093A patent/NL8004093A/nl not_active Application Discontinuation
- 1980-07-16 GR GR62474A patent/GR69590B/el unknown
- 1980-07-16 NO NO802134A patent/NO154493C/no unknown
- 1980-07-16 PL PL1980231602A patent/PL127255B1/pl unknown
- 1980-07-16 GB GB8023219A patent/GB2054589B/en not_active Expired
- 1980-07-16 IL IL60612A patent/IL60612A/xx unknown
- 1980-07-16 YU YU1830/80A patent/YU41935B/xx unknown
- 1980-07-16 SU SU802953400A patent/SU1007555A3/ru active
- 1980-07-16 SU SU802950855A patent/SU1373704A1/ru active
- 1980-07-16 PL PL1980231600A patent/PL127257B1/pl unknown
- 1980-07-16 DD DD80222669A patent/DD152126A5/de not_active IP Right Cessation
- 1980-07-16 AT AT0368480A patent/AT374177B/de not_active IP Right Cessation
- 1980-07-16 DD DD80227898A patent/DD156562A5/de not_active IP Right Cessation
- 1980-07-16 US US06/169,439 patent/US4364958A/en not_active Expired - Lifetime
- 1980-07-16 CH CH5466/80A patent/CH651296A5/de not_active IP Right Cessation
- 1980-07-16 DK DK307580A patent/DK159418C/da not_active IP Right Cessation
- 1980-07-16 PL PL1980231601A patent/PL127256B1/pl unknown
- 1980-07-16 CS CS805047A patent/CS226015B2/cs unknown
- 1980-07-16 LU LU82636A patent/LU82636A1/de unknown
- 1980-07-16 FR FR8015678A patent/FR2461700A1/fr active Granted
- 1980-07-16 IN IN814/CAL/80A patent/IN151488B/en unknown
- 1980-07-16 SE SE8005208A patent/SE450831B/sv not_active IP Right Cessation
- 1980-07-16 DD DD80227899A patent/DD156572A5/de not_active IP Right Cessation
- 1980-07-16 PL PL1980225695A patent/PL127097B1/pl unknown
- 1980-07-17 BE BE0/201435A patent/BE884353A/fr not_active IP Right Cessation
- 1980-07-17 JP JP9813780A patent/JPS5639067A/ja active Granted
- 1980-07-17 CA CA000356425A patent/CA1135707A/en not_active Expired
- 1980-07-17 FI FI802268A patent/FI74948C/fi not_active IP Right Cessation
- 1980-07-17 IT IT68139/80A patent/IT1141606B/it active
- 1980-07-17 AU AU60480/80A patent/AU535388B2/en not_active Ceased
- 1980-07-17 ES ES494310A patent/ES8106141A1/es not_active Expired
-
1981
- 1981-08-12 SU SU813315400A patent/SU1192616A3/ru active
- 1981-08-12 SU SU813322502A patent/SU1165231A3/ru active
- 1981-08-12 SU SU813317073A patent/SU1156594A3/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |