IE45647B1 - 2,3-alkylene bis (oxy) benzoic acids - Google Patents
2,3-alkylene bis (oxy) benzoic acidsInfo
- Publication number
- IE45647B1 IE45647B1 IE2409/80A IE240980A IE45647B1 IE 45647 B1 IE45647 B1 IE 45647B1 IE 2409/80 A IE2409/80 A IE 2409/80A IE 240980 A IE240980 A IE 240980A IE 45647 B1 IE45647 B1 IE 45647B1
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- substd
- opt
- carboxylic acid
- benzodioxane
- Prior art date
Links
- 235000010233 benzoic acid Nutrition 0.000 title claims description 3
- 150000001559 benzoic acids Chemical class 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- -1 cycloalkenylalkyl Chemical group 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 7
- 150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 4
- 125000003441 thioacyl group Chemical group 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 14
- 229910052736 halogen Inorganic materials 0.000 abstract description 9
- 150000002367 halogens Chemical class 0.000 abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 7
- VCLSWKVAHAJSFL-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=CC=C2C(=O)O VCLSWKVAHAJSFL-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 abstract description 2
- 125000002541 furyl group Chemical group 0.000 abstract description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000003474 anti-emetic effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 230000002903 catalepsic effect Effects 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 44
- 239000000243 solution Substances 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
- 239000002244 precipitate Substances 0.000 description 33
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- NCSFGFOXYGSSSH-UHFFFAOYSA-N 7-chlorosulfonyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(Cl)(=O)=O)C=C2C(=O)O NCSFGFOXYGSSSH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LKYLYFSTNNVQNS-UHFFFAOYSA-N 5-amino-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=CC=C2N LKYLYFSTNNVQNS-UHFFFAOYSA-N 0.000 description 3
- SXCQEJNBRGOPDI-UHFFFAOYSA-N 6-nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=CC=C([N+]([O-])=O)C(C(=O)O)=C21 SXCQEJNBRGOPDI-UHFFFAOYSA-N 0.000 description 3
- AVKRNLXCZBBZMD-UHFFFAOYSA-N 7-nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C([N+]([O-])=O)C=C2C(=O)O AVKRNLXCZBBZMD-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- RHTLNBSAROMJMO-UHFFFAOYSA-N 5-chloro-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(Cl)=CC=C2C(=O)O RHTLNBSAROMJMO-UHFFFAOYSA-N 0.000 description 2
- PWJRPWPPVFPUQD-UHFFFAOYSA-N 5-methoxy-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=CC=C2OC PWJRPWPPVFPUQD-UHFFFAOYSA-N 0.000 description 2
- YAQJEXMCCBHATG-UHFFFAOYSA-N 6,7-dibromo-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(Br)C(Br)=C2C(=O)O YAQJEXMCCBHATG-UHFFFAOYSA-N 0.000 description 2
- QFTQYWNNATXJGG-UHFFFAOYSA-N 6-chlorosulfonyl-5-methoxy-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C(C(O)=O)C=C(S(Cl)(=O)=O)C(OC)=C21 QFTQYWNNATXJGG-UHFFFAOYSA-N 0.000 description 2
- MVYGNUFUGOZHQE-UHFFFAOYSA-N 66411-18-5 Chemical compound O1CCOC2=C1C([N+]([O-])=O)=C(Br)C(Br)=C2C(=O)O MVYGNUFUGOZHQE-UHFFFAOYSA-N 0.000 description 2
- HWNSSYIJNHERQA-UHFFFAOYSA-N 7-(1-adamantylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound C1C(C2)CC(C3)CC2CC13NS(=O)(=O)C(C=C1C(=O)O)=CC2=C1OCCO2 HWNSSYIJNHERQA-UHFFFAOYSA-N 0.000 description 2
- FSRYNXDRMYDGKD-UHFFFAOYSA-N 7-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(N)C=C2C(O)=O FSRYNXDRMYDGKD-UHFFFAOYSA-N 0.000 description 2
- RNNLXFYGDGETIY-UHFFFAOYSA-N 7-ethylsulfanyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(SCC)C=C2C(O)=O RNNLXFYGDGETIY-UHFFFAOYSA-N 0.000 description 2
- ICGQFSSFYCENOY-UHFFFAOYSA-N 7-sulfanyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S)C=C2C(=O)O ICGQFSSFYCENOY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- DMLRSJNZORFCBD-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-5-amine Chemical compound O1CCOC2=C1C=CC=C2N DMLRSJNZORFCBD-UHFFFAOYSA-N 0.000 description 1
- JWZQJTGQFHIRFQ-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carboxylic acid Chemical compound O1CCOC2=CC(C(=O)O)=CC=C21 JWZQJTGQFHIRFQ-UHFFFAOYSA-N 0.000 description 1
- YGDRPEIHNMXLJM-UHFFFAOYSA-N 2,3-dihydroxy-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(O)=C1O YGDRPEIHNMXLJM-UHFFFAOYSA-N 0.000 description 1
- HHUFQIXCVKJSHC-UHFFFAOYSA-N 2-chlorosulfonyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound ClS(=O)(=O)C1COC2=C(O1)C=CC=C2C(=O)O HHUFQIXCVKJSHC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- XUXFXVMZIJMUIO-UHFFFAOYSA-N 3,4-dihydro-2h-1,5-benzodioxepine-6-carboxylic acid Chemical compound O1CCCOC2=C1C=CC=C2C(=O)O XUXFXVMZIJMUIO-UHFFFAOYSA-N 0.000 description 1
- LYCFLVALOZTFDX-UHFFFAOYSA-N 5-acetamido-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=CC=C2NC(=O)C LYCFLVALOZTFDX-UHFFFAOYSA-N 0.000 description 1
- OZGDSSXESIMADL-UHFFFAOYSA-N 5-acetamido-6-nitro-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C(C(O)=O)C=C([N+]([O-])=O)C(NC(=O)C)=C21 OZGDSSXESIMADL-UHFFFAOYSA-N 0.000 description 1
- DAZVOZDOZMSYIL-UHFFFAOYSA-N 5-methoxy-6-sulfamoyl-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C(C(O)=O)C=C(S(N)(=O)=O)C(OC)=C21 DAZVOZDOZMSYIL-UHFFFAOYSA-N 0.000 description 1
- VDMSNVFYPCEJBP-UHFFFAOYSA-N 6,7-diamino-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid dihydrochloride Chemical compound Cl.Cl.NC1=C(C2=C(OCCO2)C=C1N)C(=O)O VDMSNVFYPCEJBP-UHFFFAOYSA-N 0.000 description 1
- KTGMPWDZMLQBHX-UHFFFAOYSA-N 6,7-dinitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=CC([N+]([O-])=O)=C([N+]([O-])=O)C(C(=O)O)=C21 KTGMPWDZMLQBHX-UHFFFAOYSA-N 0.000 description 1
- PDUIYXZLRIYDTB-UHFFFAOYSA-N 6-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C(C(O)=O)C(N)=CC=C21 PDUIYXZLRIYDTB-UHFFFAOYSA-N 0.000 description 1
- AYXQAJKNYRJXCB-UHFFFAOYSA-N 7-(cyclohexylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound C=1C=2OCCOC=2C(C(=O)O)=CC=1S(=O)(=O)NC1CCCCC1 AYXQAJKNYRJXCB-UHFFFAOYSA-N 0.000 description 1
- CJPGSUPNJOCTCY-UHFFFAOYSA-N 7-(diethylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)N(CC)CC)C=C2C(O)=O CJPGSUPNJOCTCY-UHFFFAOYSA-N 0.000 description 1
- ZRISRDUHJZSFSK-UHFFFAOYSA-N 7-(dimethylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)N(C)C)C=C2C(O)=O ZRISRDUHJZSFSK-UHFFFAOYSA-N 0.000 description 1
- NQEQVGJQJCYZNI-UHFFFAOYSA-N 7-(methylsulfamoyl)-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)NC)C=C2C(O)=O NQEQVGJQJCYZNI-UHFFFAOYSA-N 0.000 description 1
- JMIKCDZBVNZHGZ-UHFFFAOYSA-N 7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(Cl)C=C2C(=O)O JMIKCDZBVNZHGZ-UHFFFAOYSA-N 0.000 description 1
- ZHWMIKHMSOYRBC-UHFFFAOYSA-N 7-ethylsulfonyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)CC)C=C2C(O)=O ZHWMIKHMSOYRBC-UHFFFAOYSA-N 0.000 description 1
- GPKDBCCYRICYKP-UHFFFAOYSA-N 7-sulfamoyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=C(S(=O)(=O)N)C=C2C(O)=O GPKDBCCYRICYKP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HCXGTVQTCVPNPQ-UHFFFAOYSA-N 8-acetamido-6-nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=C([N+]([O-])=O)C=C2NC(=O)C HCXGTVQTCVPNPQ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- DOAJWTSNTNAEIY-UHFFFAOYSA-N methyl 2,3-dihydroxybenzoate Chemical compound COC(=O)C1=CC=CC(O)=C1O DOAJWTSNTNAEIY-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7623835A FR2360305A1 (fr) | 1976-08-04 | 1976-08-04 | Nouveaux 2,3-alkylene bis (oxy)benzamides substitues, leurs derives et leurs procedes de preparation |
| IE1600/77A IE45646B1 (en) | 1976-08-04 | 1977-08-02 | Novel substituted 2,3-alkylene bis (oxy) benzamides, their derivatives and processes for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE802409L IE802409L (en) | 1978-02-04 |
| IE45647B1 true IE45647B1 (en) | 1982-10-20 |
Family
ID=9176558
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1600/77A IE45646B1 (en) | 1976-08-04 | 1977-08-02 | Novel substituted 2,3-alkylene bis (oxy) benzamides, their derivatives and processes for the preparation thereof |
| IE2409/80A IE45647B1 (en) | 1976-08-04 | 1977-08-02 | 2,3-alkylene bis (oxy) benzoic acids |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1600/77A IE45646B1 (en) | 1976-08-04 | 1977-08-02 | Novel substituted 2,3-alkylene bis (oxy) benzamides, their derivatives and processes for the preparation thereof |
Country Status (37)
| Country | Link |
|---|---|
| JP (1) | JPS57167914A (sv) |
| AR (1) | AR219709A1 (sv) |
| AT (1) | AT358034B (sv) |
| AU (1) | AU516033B2 (sv) |
| BE (1) | BE857350A (sv) |
| BG (1) | BG36496A3 (sv) |
| CA (1) | CA1114371A (sv) |
| CH (1) | CH629198A5 (sv) |
| CS (1) | CS216246B2 (sv) |
| DD (1) | DD133237A5 (sv) |
| DE (1) | DE2760414C2 (sv) |
| DK (1) | DK152366C (sv) |
| EG (1) | EG12716A (sv) |
| ES (1) | ES461175A1 (sv) |
| FI (1) | FI63938C (sv) |
| GR (1) | GR61351B (sv) |
| HK (2) | HK40382A (sv) |
| HU (1) | HU179064B (sv) |
| IE (2) | IE45646B1 (sv) |
| IL (2) | IL52644A0 (sv) |
| IN (1) | IN145473B (sv) |
| LU (1) | LU77897A1 (sv) |
| MC (1) | MC1154A1 (sv) |
| MW (1) | MW2077A1 (sv) |
| NL (1) | NL172063C (sv) |
| NO (1) | NO152133C (sv) |
| NZ (1) | NZ184816A (sv) |
| OA (1) | OA05728A (sv) |
| PH (3) | PH22114A (sv) |
| PL (1) | PL111071B1 (sv) |
| PT (1) | PT66865B (sv) |
| RO (1) | RO72963A (sv) |
| SE (2) | SE440776B (sv) |
| SU (1) | SU716523A3 (sv) |
| YU (1) | YU40005B (sv) |
| ZA (1) | ZA774701B (sv) |
| ZM (1) | ZM6077A1 (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9027098D0 (en) * | 1990-12-13 | 1991-02-06 | Beecham Group Plc | Pharmaceuticals |
| US10083697B2 (en) | 2015-05-27 | 2018-09-25 | Google Llc | Local persisting of data for selectively offline capable voice action in a voice-enabled electronic device |
| JP6452575B2 (ja) * | 2015-08-19 | 2019-01-16 | 株式会社トクヤマ | ミルタザピンの製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1473829A (fr) * | 1964-06-09 | 1967-03-24 | Ile De France | Nu-(tertiaire-aminoalkyl)-méthylène dioxybenzamides et leur préparation |
-
1977
- 1977-07-11 MC MC771250A patent/MC1154A1/xx unknown
- 1977-07-29 ES ES461175A patent/ES461175A1/es not_active Expired
- 1977-07-29 IN IN1165/CAL/77A patent/IN145473B/en unknown
- 1977-07-29 BG BG3704777A patent/BG36496A3/xx unknown
- 1977-07-29 DE DE19772760414 patent/DE2760414C2/de not_active Expired - Fee Related
- 1977-07-29 GR GR54066A patent/GR61351B/el unknown
- 1977-07-29 PT PT6686577A patent/PT66865B/pt unknown
- 1977-08-01 BE BE1008313A patent/BE857350A/xx not_active IP Right Cessation
- 1977-08-01 AU AU27507/77A patent/AU516033B2/en not_active Expired
- 1977-08-01 OA OA56243A patent/OA05728A/xx unknown
- 1977-08-01 YU YU188277A patent/YU40005B/xx unknown
- 1977-08-02 IE IE1600/77A patent/IE45646B1/en not_active IP Right Cessation
- 1977-08-02 LU LU77897A patent/LU77897A1/xx unknown
- 1977-08-02 EG EG45577A patent/EG12716A/xx active
- 1977-08-02 IE IE2409/80A patent/IE45647B1/en not_active IP Right Cessation
- 1977-08-02 AT AT569677A patent/AT358034B/de not_active IP Right Cessation
- 1977-08-02 RO RO9124577A patent/RO72963A/ro unknown
- 1977-08-03 HU HUSO001195 patent/HU179064B/hu not_active IP Right Cessation
- 1977-08-03 DD DD20042077A patent/DD133237A5/xx not_active IP Right Cessation
- 1977-08-03 CH CH956277A patent/CH629198A5/fr not_active IP Right Cessation
- 1977-08-03 NZ NZ18481677A patent/NZ184816A/xx unknown
- 1977-08-03 MW MW2077A patent/MW2077A1/xx unknown
- 1977-08-03 IL IL52644A patent/IL52644A0/xx not_active IP Right Cessation
- 1977-08-03 NO NO772739A patent/NO152133C/no unknown
- 1977-08-03 ZA ZA00774701A patent/ZA774701B/xx unknown
- 1977-08-03 SE SE7708849A patent/SE440776B/sv not_active IP Right Cessation
- 1977-08-03 DK DK346977A patent/DK152366C/da not_active IP Right Cessation
- 1977-08-03 NL NL7708616A patent/NL172063C/xx not_active IP Right Cessation
- 1977-08-03 CA CA283,994A patent/CA1114371A/en not_active Expired
- 1977-08-04 ZM ZM6077A patent/ZM6077A1/xx unknown
- 1977-08-04 CS CS775179A patent/CS216246B2/cs unknown
- 1977-08-04 FI FI772362A patent/FI63938C/fi not_active IP Right Cessation
- 1977-08-04 PL PL1977200066A patent/PL111071B1/pl not_active IP Right Cessation
- 1977-08-04 PH PH20078A patent/PH22114A/en unknown
- 1977-08-04 SU SU772507701A patent/SU716523A3/ru active
- 1977-08-08 AR AR26867377A patent/AR219709A1/es active
-
1981
- 1981-03-25 PH PH25426-AA patent/PH18629A/en unknown
- 1981-08-07 PH PH26025A patent/PH17710A/en unknown
-
1982
- 1982-03-19 JP JP4547682A patent/JPS57167914A/ja active Granted
- 1982-06-25 IL IL66138A patent/IL66138A0/xx not_active IP Right Cessation
- 1982-09-16 HK HK40382A patent/HK40382A/xx unknown
- 1982-09-16 HK HK40482A patent/HK40482A/xx unknown
- 1982-11-17 SE SE8206546A patent/SE453390B/sv not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |