NO763197L - Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-benzimidazolderivater. - Google Patents
Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-benzimidazolderivater.Info
- Publication number
- NO763197L NO763197L NO763197A NO763197A NO763197L NO 763197 L NO763197 L NO 763197L NO 763197 A NO763197 A NO 763197A NO 763197 A NO763197 A NO 763197A NO 763197 L NO763197 L NO 763197L
- Authority
- NO
- Norway
- Prior art keywords
- carbomethoxyamino
- benzothiadiazine
- benzimidazole
- ester
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 6
- 230000000694 effects Effects 0.000 title description 4
- -1 1-4 C-atom alkoxy Chemical class 0.000 claims description 21
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- NLXPDNKIQMAKCH-UHFFFAOYSA-N 1h-2,1,4-benzothiadiazine Chemical class C1=CC=C2NSC=NC2=C1 NLXPDNKIQMAKCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000000354 decomposition reaction Methods 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000013543 active substance Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000007658 benzothiadiazines Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- LPGZJNUYYNQUCX-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3,4-dichlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 LPGZJNUYYNQUCX-UHFFFAOYSA-N 0.000 description 2
- ISBOUSHXNPQEJV-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3,5-dichlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 ISBOUSHXNPQEJV-UHFFFAOYSA-N 0.000 description 2
- OAXIPAMEOHCMKW-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-chlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(Cl)=C1 OAXIPAMEOHCMKW-UHFFFAOYSA-N 0.000 description 2
- HFXWMGNCZMWMRA-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-methylbenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(C)=C1 HFXWMGNCZMWMRA-UHFFFAOYSA-N 0.000 description 2
- LKUIZYHKNRHFFZ-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 4-chlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 LKUIZYHKNRHFFZ-UHFFFAOYSA-N 0.000 description 2
- MWPQFRBSPKPQEU-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1 MWPQFRBSPKPQEU-UHFFFAOYSA-N 0.000 description 2
- USQXMRHUAONQBW-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC(C)C)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 USQXMRHUAONQBW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 244000000013 helminth Species 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALKQQCLVJCSDJA-UHFFFAOYSA-N (2-nitrophenyl)carbamothioylcarbamic acid Chemical compound C1=CC=C(C(=C1)NC(=S)NC(=O)O)[N+](=O)[O-] ALKQQCLVJCSDJA-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
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- 108010010803 Gelatin Proteins 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
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- 241000244174 Strongyloides Species 0.000 description 1
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- QQJXCDUBIAECTE-UHFFFAOYSA-N [3-(butoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OCCCC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1 QQJXCDUBIAECTE-UHFFFAOYSA-N 0.000 description 1
- KNSMAFVMAGPLCD-UHFFFAOYSA-N [3-(ethoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OCC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 KNSMAFVMAGPLCD-UHFFFAOYSA-N 0.000 description 1
- WNCNJIMAODCZCH-UHFFFAOYSA-N [3-(ethoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] benzenesulfonate Chemical compound C1=C2NSC(NC(=O)OCC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1 WNCNJIMAODCZCH-UHFFFAOYSA-N 0.000 description 1
- ILOHHNAACFCVAK-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 2-bromobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1Br ILOHHNAACFCVAK-UHFFFAOYSA-N 0.000 description 1
- HSQIOBWCNDTNBK-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 2-chloro-4-methylbenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(C)C=C1Cl HSQIOBWCNDTNBK-UHFFFAOYSA-N 0.000 description 1
- DXSMOLNVJMYSSA-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 2-chloro-6-methylbenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=C(C)C=CC=C1Cl DXSMOLNVJMYSSA-UHFFFAOYSA-N 0.000 description 1
- FPUWRIHKPGHAMY-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 2-chlorobenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1Cl FPUWRIHKPGHAMY-UHFFFAOYSA-N 0.000 description 1
- UUGCEJKKTVSZRR-UHFFFAOYSA-N [3-(methoxycarbonylamino)-1h-2,1,4-benzothiadiazin-7-yl] 2-methylbenzenesulfonate Chemical compound C1=C2NSC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1C UUGCEJKKTVSZRR-UHFFFAOYSA-N 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- UFEJXQWSRLAIOY-UHFFFAOYSA-N phenyl 1h-benzimidazole-2-sulfonate Chemical compound N=1C2=CC=CC=C2NC=1S(=O)(=O)OC1=CC=CC=C1 UFEJXQWSRLAIOY-UHFFFAOYSA-N 0.000 description 1
- FNKPQMSVJJSRBP-UHFFFAOYSA-N phenyl 2-(butoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OCCCC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 FNKPQMSVJJSRBP-UHFFFAOYSA-N 0.000 description 1
- YVPYMPMYOGQFIW-UHFFFAOYSA-N phenyl 2-(ethoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 YVPYMPMYOGQFIW-UHFFFAOYSA-N 0.000 description 1
- JMVOTQMMWZCLEX-UHFFFAOYSA-N phenyl 2-(methoxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 JMVOTQMMWZCLEX-UHFFFAOYSA-N 0.000 description 1
- BWJKYQSSWVHQEG-UHFFFAOYSA-N phenyl 2-(propan-2-yloxycarbonylamino)-3h-benzimidazole-5-sulfonate Chemical compound C1=C2NC(NC(=O)OC(C)C)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 BWJKYQSSWVHQEG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000035938 sexual maturation Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752541751 DE2541751A1 (de) | 1975-09-19 | 1975-09-19 | Anthelminthisch wirksame 2-carbalkoxyamino-benzimidazolderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO763197L true NO763197L (no) | 1977-03-22 |
Family
ID=5956861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO763197A NO763197L (no) | 1975-09-19 | 1976-09-17 | Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-benzimidazolderivater. |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT356651B (xx) |
| CA (1) | CA1069908A (xx) |
| CH (1) | CH605822A5 (xx) |
| DE (1) | DE2541751A1 (xx) |
| DK (1) | DK419976A (xx) |
| EG (1) | EG12507A (xx) |
| ES (1) | ES451512A1 (xx) |
| FI (1) | FI762654A (xx) |
| GR (1) | GR70297B (xx) |
| HU (1) | HU172248B (xx) |
| LU (1) | LU75816A1 (xx) |
| MX (1) | MX3567E (xx) |
| NL (1) | NL7610191A (xx) |
| NO (1) | NO763197L (xx) |
| PT (1) | PT65608B (xx) |
| SE (1) | SE7610311L (xx) |
-
1975
- 1975-09-19 DE DE19752541751 patent/DE2541751A1/de active Pending
-
1976
- 1976-09-11 EG EG76551A patent/EG12507A/xx active
- 1976-09-14 MX MX764928U patent/MX3567E/es unknown
- 1976-09-14 ES ES451512A patent/ES451512A1/es not_active Expired
- 1976-09-14 NL NL7610191A patent/NL7610191A/xx not_active Application Discontinuation
- 1976-09-16 LU LU75816A patent/LU75816A1/xx unknown
- 1976-09-16 SE SE7610311A patent/SE7610311L/xx unknown
- 1976-09-16 HU HU76HO00001928A patent/HU172248B/hu unknown
- 1976-09-16 FI FI762654A patent/FI762654A/fi not_active Application Discontinuation
- 1976-09-17 AT AT690976A patent/AT356651B/de not_active IP Right Cessation
- 1976-09-17 PT PT65608A patent/PT65608B/pt unknown
- 1976-09-17 CA CA261,424A patent/CA1069908A/en not_active Expired
- 1976-09-17 DK DK419976A patent/DK419976A/da not_active Application Discontinuation
- 1976-09-17 NO NO763197A patent/NO763197L/no unknown
- 1976-09-17 CH CH1182276A patent/CH605822A5/xx not_active IP Right Cessation
- 1976-09-18 GR GR51722A patent/GR70297B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7610191A (nl) | 1977-03-22 |
| DK419976A (da) | 1977-03-20 |
| FI762654A (xx) | 1977-03-20 |
| HU172248B (hu) | 1978-07-28 |
| CH605822A5 (xx) | 1978-10-13 |
| CA1069908A (en) | 1980-01-15 |
| ATA690976A (de) | 1979-10-15 |
| PT65608A (de) | 1976-10-01 |
| MX3567E (es) | 1981-03-13 |
| AT356651B (de) | 1980-05-12 |
| PT65608B (de) | 1978-05-10 |
| LU75816A1 (xx) | 1977-05-13 |
| ES451512A1 (es) | 1977-12-16 |
| GR70297B (xx) | 1982-09-06 |
| SE7610311L (sv) | 1977-03-20 |
| EG12507A (en) | 1978-12-31 |
| DE2541751A1 (de) | 1977-03-24 |
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