CS195689B2 - Method of producing novel derivatives of nitroimidazole - Google Patents
Method of producing novel derivatives of nitroimidazole Download PDFInfo
- Publication number
- CS195689B2 CS195689B2 CS746554A CS655474A CS195689B2 CS 195689 B2 CS195689 B2 CS 195689B2 CS 746554 A CS746554 A CS 746554A CS 655474 A CS655474 A CS 655474A CS 195689 B2 CS195689 B2 CS 195689B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- methyl
- formula
- treated
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 150000004957 nitroimidazoles Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 50
- -1 imidazole compound Chemical class 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- RSOPCRYPVDDVAX-UHFFFAOYSA-N 1-methyl-2-methylsulfonyl-5-nitroimidazole Chemical compound CN1C([N+]([O-])=O)=CN=C1S(C)(=O)=O RSOPCRYPVDDVAX-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- GBDVZLHCKQDABB-UHFFFAOYSA-N 1-methyl-4-methylsulfonyl-5-nitroimidazole Chemical compound CN1C=NC(S(C)(=O)=O)=C1[N+]([O-])=O GBDVZLHCKQDABB-UHFFFAOYSA-N 0.000 claims 1
- UIQNTKKFJXHGIL-UHFFFAOYSA-N 2-methylsulfonyl-5-nitro-1h-imidazole Chemical compound CS(=O)(=O)C1=NC=C([N+]([O-])=O)N1 UIQNTKKFJXHGIL-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 150000001351 alkyl iodides Chemical class 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- LRDXJLPHTXEZMI-UHFFFAOYSA-N n,n-dimethyl-2-oxoimidazolidine-1-carboxamide Chemical compound CN(C)C(=O)N1CCNC1=O LRDXJLPHTXEZMI-UHFFFAOYSA-N 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 11
- 230000000845 anti-microbial effect Effects 0.000 abstract description 3
- 241000224483 Coccidia Species 0.000 abstract description 2
- 241000242678 Schistosoma Species 0.000 abstract description 2
- 239000004599 antimicrobial Substances 0.000 abstract description 2
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 241001502500 Trichomonadida Species 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019730 animal feed additive Nutrition 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000000813 microbial effect Effects 0.000 abstract 1
- XMWZWFFVDSIGJD-UHFFFAOYSA-N n-methyl-3-(1-methyl-5-nitroimidazol-2-yl)-2-oxoimidazolidine-1-carbothioamide Chemical compound O=C1N(C(=S)NC)CCN1C1=NC=C([N+]([O-])=O)N1C XMWZWFFVDSIGJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000011368 organic material Substances 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 63
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 239000007858 starting material Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000725 suspension Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000155 melt Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 16
- 239000012312 sodium hydride Substances 0.000 description 16
- 229910000104 sodium hydride Inorganic materials 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 13
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
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- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 4
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- OWWASHBXVFOTDF-UHFFFAOYSA-N n-methyl-1h-imidazole-2-carboxamide Chemical compound CNC(=O)C1=NC=CN1 OWWASHBXVFOTDF-UHFFFAOYSA-N 0.000 description 2
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960000654 sulfafurazole Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- 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
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS774703A CS195690B2 (cs) | 1973-09-24 | 1977-07-14 | Způsob výroby nových derivátů nitroimidazolu |
| CS774704A CS195691B2 (en) | 1973-09-24 | 1977-07-14 | Method of producing novel derivatives of nitroimidazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1366773A CH592653A5 (OSRAM) | 1973-09-24 | 1973-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195689B2 true CS195689B2 (en) | 1980-02-29 |
Family
ID=4394325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS746554A CS195689B2 (en) | 1973-09-24 | 1974-09-24 | Method of producing novel derivatives of nitroimidazole |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5910347B2 (OSRAM) |
| AR (2) | AR212578A1 (OSRAM) |
| AT (1) | AT337692B (OSRAM) |
| BE (1) | BE820206A (OSRAM) |
| BG (2) | BG22823A3 (OSRAM) |
| CH (1) | CH592653A5 (OSRAM) |
| CS (1) | CS195689B2 (OSRAM) |
| DD (1) | DD114814A5 (OSRAM) |
| DE (1) | DE2444070A1 (OSRAM) |
| DK (1) | DK447474A (OSRAM) |
| DO (1) | DOP1981002973A (OSRAM) |
| ES (1) | ES430352A1 (OSRAM) |
| FI (1) | FI62293C (OSRAM) |
| FR (1) | FR2244498A1 (OSRAM) |
| HU (1) | HU171562B (OSRAM) |
| IE (1) | IE40003B1 (OSRAM) |
| IL (1) | IL45536A (OSRAM) |
| NL (1) | NL7412482A (OSRAM) |
| NO (1) | NO141895C (OSRAM) |
| OA (1) | OA04828A (OSRAM) |
| PH (1) | PH13743A (OSRAM) |
| PL (3) | PL96510B1 (OSRAM) |
| RO (1) | RO70190A (OSRAM) |
| SE (1) | SE416300B (OSRAM) |
| SU (3) | SU542473A3 (OSRAM) |
| YU (3) | YU37337B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5956254U (ja) * | 1982-10-05 | 1984-04-12 | 住友金属鉱山株式会社 | 擁壁ブロツク |
| DE4426757A1 (de) * | 1994-07-28 | 1996-02-01 | Bayer Ag | 2-Imidazolidinon-Derivate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2944061A (en) * | 1957-09-20 | 1960-07-05 | Acyl derivatives and process | |
| IL39283A (en) * | 1971-05-03 | 1976-01-30 | Ciba Geigy Ag | Substituted 2-oxo or thioxo-3-(5-nitro-imidazol-2-yl)-tetrahydroimidazoles and their manufacture |
| BE795068A (fr) * | 1972-02-08 | 1973-08-07 | Ciba Geigy | Nouveaux 4- ou 5-nitro-inmidazoles et procedes pour leur preparation |
-
1973
- 1973-09-24 CH CH1366773A patent/CH592653A5/xx not_active IP Right Cessation
-
1974
- 1974-08-21 DK DK447474A patent/DK447474A/da not_active Application Discontinuation
- 1974-08-22 IE IE1746/74A patent/IE40003B1/xx unknown
- 1974-08-26 IL IL45536A patent/IL45536A/xx unknown
- 1974-09-06 SE SE7411296A patent/SE416300B/xx not_active IP Right Cessation
- 1974-09-12 FI FI2669/74A patent/FI62293C/fi active
- 1974-09-14 DE DE2444070A patent/DE2444070A1/de not_active Ceased
- 1974-09-18 FR FR7431471A patent/FR2244498A1/fr active Granted
- 1974-09-20 NO NO743395A patent/NO141895C/no unknown
- 1974-09-20 NL NL7412482A patent/NL7412482A/xx not_active Application Discontinuation
- 1974-09-21 OA OA55302A patent/OA04828A/xx unknown
- 1974-09-23 PL PL1974174285A patent/PL96510B1/pl unknown
- 1974-09-23 AR AR255685A patent/AR212578A1/es active
- 1974-09-23 PL PL1974185100A patent/PL95689B1/pl unknown
- 1974-09-23 RO RO7487513A patent/RO70190A/ro unknown
- 1974-09-23 AT AT762174A patent/AT337692B/de not_active IP Right Cessation
- 1974-09-23 PL PL1974185103A patent/PL95691B1/pl unknown
- 1974-09-23 SU SU2063056A patent/SU542473A3/ru active
- 1974-09-23 BE BE148776A patent/BE820206A/xx not_active IP Right Cessation
- 1974-09-23 PH PH16324A patent/PH13743A/en unknown
- 1974-09-23 DD DD181273A patent/DD114814A5/xx unknown
- 1974-09-23 BG BG027754A patent/BG22823A3/xx unknown
- 1974-09-23 YU YU2559/74A patent/YU37337B/xx unknown
- 1974-09-23 BG BG029300A patent/BG22813A3/xx unknown
- 1974-09-24 ES ES430352A patent/ES430352A1/es not_active Expired
- 1974-09-24 JP JP49110385A patent/JPS5910347B2/ja not_active Expired
- 1974-09-24 HU HU74CI00001509A patent/HU171562B/hu unknown
- 1974-09-24 CS CS746554A patent/CS195689B2/cs unknown
-
1975
- 1975-01-01 AR AR258970A patent/AR207980A1/es active
- 1975-07-02 SU SU7502149413A patent/SU564812A3/ru active
- 1975-07-02 SU SU7502149414A patent/SU571191A3/ru active
-
1980
- 1980-11-24 YU YU2983/80A patent/YU37339B/xx unknown
- 1980-11-24 YU YU2982/80A patent/YU37338B/xx unknown
-
1981
- 1981-02-09 DO DO1981002973A patent/DOP1981002973A/es unknown
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