DD277274A5 - Verfahren zur herstellung von alkoxybenzonitrilderivaten - Google Patents
Verfahren zur herstellung von alkoxybenzonitrilderivaten Download PDFInfo
- Publication number
- DD277274A5 DD277274A5 DD88324296A DD32429688A DD277274A5 DD 277274 A5 DD277274 A5 DD 277274A5 DD 88324296 A DD88324296 A DD 88324296A DD 32429688 A DD32429688 A DD 32429688A DD 277274 A5 DD277274 A5 DD 277274A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- benzonitrile
- propyl
- amino
- ethyl
- compound
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000000203 mixture Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005905 mesyloxy group Chemical group 0.000 claims description 3
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims 5
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 5
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- -1 4-cyanophenoxy Chemical group 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- 239000002775 capsule Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
- ZMHOBBKJBYLXFR-BPNWFJGMSA-N 4-[(2r)-3-[ethyl(3-propylsulfinylpropyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCCS(=O)CCCN(CC)C[C@@H](O)COC1=CC=C(C#N)C=C1 ZMHOBBKJBYLXFR-BPNWFJGMSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000007903 gelatin capsule Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- WREXVDPOLDOXJL-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)benzonitrile Chemical compound C1=CC(C#N)=CC=C1OCC1OC1 WREXVDPOLDOXJL-UHFFFAOYSA-N 0.000 description 4
- JWYAJJXJGHRSJC-UHFFFAOYSA-N 4-[3-(2-hydroxyethylamino)propoxy]benzonitrile Chemical compound OCCNCCCOC1=CC=C(C#N)C=C1 JWYAJJXJGHRSJC-UHFFFAOYSA-N 0.000 description 4
- BNIJSWPESWZPCF-UHFFFAOYSA-N 4-[3-[ethyl(3-propylsulfanylpropyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCCSCCCN(CC)CC(O)COC1=CC=C(C#N)C=C1 BNIJSWPESWZPCF-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 description 3
- QJQHYOZSXUTNLN-UHFFFAOYSA-N 3-propylsulfanylpropan-1-amine Chemical compound CCCSCCCN QJQHYOZSXUTNLN-UHFFFAOYSA-N 0.000 description 3
- RMRHEPZUTYXELS-UHFFFAOYSA-N 6-hydroxybenzo[d][1,3,2]benzodioxaphosphepine 6-oxide Chemical compound O1P(O)(=O)OC2=CC=CC=C2C2=CC=CC=C21 RMRHEPZUTYXELS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000036982 action potential Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 2
- LJMRNIWYGSYMSF-UHFFFAOYSA-N 3-propylsulfanylpropanenitrile Chemical compound CCCSCCC#N LJMRNIWYGSYMSF-UHFFFAOYSA-N 0.000 description 2
- DMVZVOUWLINXLP-SECBINFHSA-N 4-[(2r)-2,3-dihydroxypropoxy]benzonitrile Chemical compound OC[C@@H](O)COC1=CC=C(C#N)C=C1 DMVZVOUWLINXLP-SECBINFHSA-N 0.000 description 2
- DUPRFZGZOUOFDM-UHFFFAOYSA-N 4-[3-(ethylamino)-2-hydroxypropoxy]benzonitrile Chemical compound CCNCC(O)COC1=CC=C(C#N)C=C1 DUPRFZGZOUOFDM-UHFFFAOYSA-N 0.000 description 2
- MXRZNBPFJXURCU-UHFFFAOYSA-N 4-[3-[2-hydroxyethyl(3-methylsulfinylpropyl)amino]propoxy]benzonitrile Chemical compound CS(=O)CCCN(CCO)CCCOC1=CC=C(C#N)C=C1 MXRZNBPFJXURCU-UHFFFAOYSA-N 0.000 description 2
- JOTFXCNLTLKZHO-UHFFFAOYSA-N 4-[3-[2-hydroxyethyl(3-propylsulfanylpropyl)amino]propoxy]benzonitrile Chemical compound CCCSCCCN(CCO)CCCOC1=CC=C(C#N)C=C1 JOTFXCNLTLKZHO-UHFFFAOYSA-N 0.000 description 2
- VLSOPGVLYPUIKR-UHFFFAOYSA-N 5-propylsulfanylpentanamide Chemical compound CCCSCCCCC(N)=O VLSOPGVLYPUIKR-UHFFFAOYSA-N 0.000 description 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 101150046432 Tril gene Proteins 0.000 description 2
- WZMVRBZTVVOICZ-JTQLQIEISA-N [(2s)-3-(4-cyanophenoxy)-2-hydroxypropyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](O)COC1=CC=C(C#N)C=C1 WZMVRBZTVVOICZ-JTQLQIEISA-N 0.000 description 2
- UJWNJVRQCIHBNL-UHFFFAOYSA-M [3-(4-cyanophenoxy)-2-hydroxypropyl]-diethyl-(3-propylsulfinylpropyl)azanium;iodide Chemical compound [I-].CCCS(=O)CCC[N+](CC)(CC)CC(O)COC1=CC=C(C#N)C=C1 UJWNJVRQCIHBNL-UHFFFAOYSA-M 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 230000000297 inotrophic effect Effects 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- SAJHWCCWVHBKJR-UHFFFAOYSA-N n-ethyl-3-propylsulfanylpropan-1-amine Chemical compound CCCSCCCNCC SAJHWCCWVHBKJR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002336 repolarization Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- DFMOYZCKOYEADZ-UHFFFAOYSA-N 1-bromo-2-fluoropropane Chemical compound CC(F)CBr DFMOYZCKOYEADZ-UHFFFAOYSA-N 0.000 description 1
- GNHPNQQIVWCDEU-UHFFFAOYSA-N 1-bromo-3-methylsulfanylpropane Chemical compound CSCCCBr GNHPNQQIVWCDEU-UHFFFAOYSA-N 0.000 description 1
- BJVPBQFEKHPWSD-UHFFFAOYSA-N 1-bromo-3-propylsulfanylpropane Chemical compound CCCSCCCBr BJVPBQFEKHPWSD-UHFFFAOYSA-N 0.000 description 1
- KUYSPBAZAAOWOF-UHFFFAOYSA-N 1-bromo-3-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCCBr KUYSPBAZAAOWOF-UHFFFAOYSA-N 0.000 description 1
- CGTGMRIOAZJUQA-UHFFFAOYSA-N 2-(3-bromopropoxy)benzonitrile Chemical compound BrCCCOC1=CC=CC=C1C#N CGTGMRIOAZJUQA-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BNIJSWPESWZPCF-KRWDZBQOSA-N 4-[(2s)-3-[ethyl(3-propylsulfanylpropyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCCSCCCN(CC)C[C@H](O)COC1=CC=C(C#N)C=C1 BNIJSWPESWZPCF-KRWDZBQOSA-N 0.000 description 1
- ZMHOBBKJBYLXFR-KEJDIYNNSA-N 4-[(2s)-3-[ethyl(3-propylsulfinylpropyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCCS(=O)CCCN(CC)C[C@H](O)COC1=CC=C(C#N)C=C1 ZMHOBBKJBYLXFR-KEJDIYNNSA-N 0.000 description 1
- KPVLJDRAWXBQBG-UHFFFAOYSA-N 4-[2-hydroxy-3-(3-propylsulfanylpropylamino)propoxy]benzonitrile Chemical compound CCCSCCCNCC(O)COC1=CC=C(C#N)C=C1 KPVLJDRAWXBQBG-UHFFFAOYSA-N 0.000 description 1
- FACYNKBJXTXHFD-UHFFFAOYSA-N 4-[2-hydroxy-3-(methylamino)propoxy]benzonitrile Chemical compound CNCC(O)COC1=CC=C(C#N)C=C1 FACYNKBJXTXHFD-UHFFFAOYSA-N 0.000 description 1
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- UFYHJPWSKQCHPR-UHFFFAOYSA-N 4-[3-[ethyl(4-ethylsulfanylbutyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCSCCCCN(CC)CC(O)COC1=CC=C(C#N)C=C1 UFYHJPWSKQCHPR-UHFFFAOYSA-N 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- 238000002560 therapeutic procedure Methods 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8705150A SE8705150D0 (sv) | 1987-12-23 | 1987-12-23 | Novel antiarrhythmic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD277274A5 true DD277274A5 (de) | 1990-03-28 |
Family
ID=20370706
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88324296A DD277274A5 (de) | 1987-12-23 | 1988-12-28 | Verfahren zur herstellung von alkoxybenzonitrilderivaten |
| DD89329730A DD295353A5 (de) | 1987-12-23 | 1989-06-19 | Verfahren zur herstellung von benzonitrilderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89329730A DD295353A5 (de) | 1987-12-23 | 1989-06-19 | Verfahren zur herstellung von benzonitrilderivaten |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US5034411A (fi) |
| EP (2) | EP0322390B1 (fi) |
| JP (2) | JPH0637458B2 (fi) |
| KR (2) | KR900700441A (fi) |
| CN (3) | CN1033804A (fi) |
| AR (1) | AR247729A1 (fi) |
| AT (2) | ATE81848T1 (fi) |
| AU (4) | AU625872B2 (fi) |
| DD (2) | DD277274A5 (fi) |
| DE (2) | DE3875934T2 (fi) |
| DK (2) | DK404789A (fi) |
| EG (1) | EG18681A (fi) |
| ES (2) | ES2043891T3 (fi) |
| FI (2) | FI92192C (fi) |
| GR (2) | GR3006241T3 (fi) |
| HU (3) | HU913679D0 (fi) |
| IE (2) | IE883859L (fi) |
| IL (2) | IL88749A (fi) |
| IS (1) | IS1558B (fi) |
| LT (4) | LTIP1687A (fi) |
| LV (1) | LV10250A (fi) |
| MX (1) | MX174084B (fi) |
| MY (1) | MY103945A (fi) |
| NO (2) | NO171724C (fi) |
| NZ (1) | NZ227381A (fi) |
| PH (2) | PH25526A (fi) |
| PL (2) | PL157747B1 (fi) |
| PT (2) | PT89311B (fi) |
| RU (3) | RU2024503C1 (fi) |
| SE (1) | SE8705150D0 (fi) |
| WO (3) | WO1989005794A1 (fi) |
| YU (2) | YU47580B (fi) |
| ZA (2) | ZA889424B (fi) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8705150D0 (sv) * | 1987-12-23 | 1987-12-23 | Haessle Ab | Novel antiarrhythmic agents |
| SE8902235D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel cyclodextrin inclusion complexes |
| SE8902237D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel stereoisomers |
| SE8902236D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel polystyrenesulfonate |
| SE9003902D0 (sv) * | 1990-12-07 | 1990-12-07 | Astra Ab | Solid dosage forms of a drug |
| US5084463A (en) * | 1989-12-11 | 1992-01-28 | American Home Products Corporation | N-quinolinyl alkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing class III antiarrhythmic activity |
| US5619274A (en) * | 1990-09-10 | 1997-04-08 | Starsight Telecast, Inc. | Television schedule information transmission and utilization system and process |
| UA26190C2 (uk) * | 1992-07-28 | 1999-07-19 | Сейфтек Ай Лімітед | Шприц |
| US5679706A (en) * | 1994-09-30 | 1997-10-21 | Bristol-Myers Squibb Company | Combination of a potassium channel activator and an antiarrhythmic agent |
| US6143569A (en) * | 1998-08-31 | 2000-11-07 | The United States Of America As Represented By The Secretary Of The Navy | Chelators exhibiting triple fluorescence |
| GB0123961D0 (en) * | 2001-10-05 | 2001-11-28 | Astrazeneca Ab | Process and intermediates |
| WO2004113305A2 (en) | 2003-06-16 | 2004-12-29 | Vertex Pharmaceuticals Incorporated | Diamino substituted quinazoline derivatives as promoters of smn2 |
| US7356365B2 (en) * | 2003-07-09 | 2008-04-08 | Glucolight Corporation | Method and apparatus for tissue oximetry |
| RU2631231C1 (ru) * | 2016-12-01 | 2017-09-19 | Научно-производственная ассоциация "Технопарк Авиационных Технологий" | Способ получения заготовки лопатки газотурбинного двигателя для линейной сварки трением |
| CN115417973B (zh) * | 2022-11-03 | 2023-03-24 | 广东粤港澳大湾区黄埔材料研究院 | 抗菌聚氨酯材料及其制备方法和应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3149147A (en) * | 1961-03-16 | 1964-09-15 | Smith Kline French Lab | Novel substituted phenylalkylamines |
| FR152F (fi) * | 1962-01-24 | |||
| GB1069345A (en) * | 1963-07-19 | 1967-05-17 | Ici Ltd | New alkanolamine derivatives |
| DE1593771A1 (de) * | 1967-04-06 | 1970-04-30 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von 1-Phenoxy-2-amino-alkanen |
| BE757005A (fr) * | 1969-10-02 | 1971-04-02 | Bristol Myers Co | Phenethanolamines substituees et procede pour leur preparation |
| GB1457876A (en) * | 1972-12-15 | 1976-12-08 | Ici Ltd | Alkanolamine derivatives device for use in |
| SE404793B (sv) * | 1973-05-25 | 1978-10-30 | Boehringer Sohn Ingelheim | Forfarande for framstellning av vissa angivna nitrilsubstituerade 1-fenoxi-2-hydroxi-3-lagalkylaminopropaner |
| GB1433920A (en) * | 1973-10-01 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
| FR2280376A1 (fr) * | 1974-08-02 | 1976-02-27 | Sogeras | Nouveaux derives du piperidine-4 ethanol |
| DE2503222A1 (de) * | 1975-01-27 | 1976-07-29 | Boehringer Sohn Ingelheim | Verfahren zur herstellung von 1-aryl- oxy-3-n-substituierten aminopropanderivaten |
| SE421123B (sv) * | 1976-08-25 | 1981-11-30 | Boehringer Sohn Ingelheim | Forfarande for framstellning av vissa angivna nitrilsubstituerade 1-fenoxi-2-hydroxi-3-alkylaminopropaner |
| US4283534A (en) * | 1979-04-11 | 1981-08-11 | Basf Aktiengesellschaft | Reductive alkylation of nitrogen heterocycles |
| US4544654A (en) * | 1984-03-20 | 1985-10-01 | Schering A.G. | Substituted sulfonamidobenzamides, antiarrhythmic agents and compositions thereof |
| US4614746A (en) * | 1985-03-21 | 1986-09-30 | American Cyanamid Company | 5-fluorobenzonitrile derivatives for increasing the lean meat to fat ratio and/or enhancing the growth rate of warm-blooded animals |
| CA1267416A (en) * | 1985-06-17 | 1990-04-03 | Ila Sircar | 1,4-dihydropyridine derivatives useful for the treatment of cardiovascular disorders |
| EG18188A (en) * | 1986-05-01 | 1992-09-30 | Pfizer Ltd | Process for preparation anti-arhythmia agents |
| SE8705150D0 (sv) * | 1987-12-23 | 1987-12-23 | Haessle Ab | Novel antiarrhythmic agents |
| SE8902236D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel polystyrenesulfonate |
| SE8902237D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel stereoisomers |
-
1987
- 1987-12-23 SE SE8705150A patent/SE8705150D0/xx unknown
-
1988
- 1988-12-15 ZA ZA889424A patent/ZA889424B/xx unknown
- 1988-12-19 NZ NZ227381A patent/NZ227381A/en unknown
- 1988-12-20 AT AT88850427T patent/ATE81848T1/de not_active IP Right Cessation
- 1988-12-20 DE DE8888850428T patent/DE3875934T2/de not_active Expired - Fee Related
- 1988-12-20 HU HU913679A patent/HU913679D0/hu unknown
- 1988-12-20 EP EP88850428A patent/EP0322390B1/en not_active Expired - Lifetime
- 1988-12-20 AU AU28241/89A patent/AU625872B2/en not_active Ceased
- 1988-12-20 WO PCT/SE1988/000691 patent/WO1989005794A1/en active IP Right Grant
- 1988-12-20 ES ES88850427T patent/ES2043891T3/es not_active Expired - Lifetime
- 1988-12-20 AT AT88850428T patent/ATE82257T1/de not_active IP Right Cessation
- 1988-12-20 JP JP50046888A patent/JPH0637458B2/ja not_active Expired - Lifetime
- 1988-12-20 WO PCT/SE1988/000692 patent/WO1989005795A1/en active Application Filing
- 1988-12-20 EP EP88850427A patent/EP0322389B1/en not_active Expired - Lifetime
- 1988-12-20 AU AU28244/89A patent/AU2824489A/en active Granted
- 1988-12-20 ES ES88850428T patent/ES2045189T3/es not_active Expired - Lifetime
- 1988-12-20 HU HU89359A patent/HU205895B/hu not_active IP Right Cessation
- 1988-12-20 HU HU89361A patent/HUT54346A/hu unknown
- 1988-12-20 AU AU28244/89A patent/AU625774B2/en not_active Ceased
- 1988-12-20 JP JP1500469A patent/JPH02502726A/ja active Pending
- 1988-12-20 DE DE8888850427T patent/DE3875600T2/de not_active Expired - Fee Related
- 1988-12-21 IL IL8874988A patent/IL88749A/en not_active IP Right Cessation
- 1988-12-21 PH PH37959A patent/PH25526A/en unknown
- 1988-12-21 PH PH37960A patent/PH26828A/en unknown
- 1988-12-21 IS IS3425A patent/IS1558B/is unknown
- 1988-12-21 IL IL10374188A patent/IL103741A/en not_active IP Right Cessation
- 1988-12-22 IE IE883859A patent/IE883859L/xx unknown
- 1988-12-22 PT PT89311A patent/PT89311B/pt not_active IP Right Cessation
- 1988-12-22 IE IE883860A patent/IE883860L/xx unknown
- 1988-12-22 PT PT89312A patent/PT89312B/pt not_active IP Right Cessation
- 1988-12-22 EG EG653/88A patent/EG18681A/xx active
- 1988-12-22 MX MX014310A patent/MX174084B/es unknown
- 1988-12-22 US US07/289,630 patent/US5034411A/en not_active Expired - Fee Related
- 1988-12-22 AU AU29103/89A patent/AU2910389A/en not_active Abandoned
- 1988-12-22 MY MYPI88001510A patent/MY103945A/en unknown
- 1988-12-22 AR AR88312835A patent/AR247729A1/es active
- 1988-12-22 WO PCT/SE1988/000697 patent/WO1989005806A1/en unknown
- 1988-12-23 YU YU234088A patent/YU47580B/sh unknown
- 1988-12-23 CN CN88108941A patent/CN1033804A/zh active Pending
- 1988-12-23 PL PL1988276698A patent/PL157747B1/pl unknown
- 1988-12-23 PL PL1988287936A patent/PL159551B1/pl unknown
- 1988-12-28 DD DD88324296A patent/DD277274A5/de not_active IP Right Cessation
-
1989
- 1989-06-12 ZA ZA894441A patent/ZA894441B/xx unknown
- 1989-06-19 DD DD89329730A patent/DD295353A5/de not_active IP Right Cessation
- 1989-06-22 CN CN89104335A patent/CN1048214A/zh active Pending
- 1989-08-17 DK DK404789A patent/DK404789A/da not_active Application Discontinuation
- 1989-08-17 DK DK404889A patent/DK404889A/da unknown
- 1989-08-22 NO NO893375A patent/NO171724C/no unknown
- 1989-08-22 KR KR1019890701579A patent/KR900700441A/ko not_active Application Discontinuation
- 1989-08-22 FI FI893936A patent/FI92192C/fi not_active IP Right Cessation
- 1989-08-22 FI FI893937A patent/FI893937A0/fi not_active Application Discontinuation
- 1989-08-22 RU SU894614813A patent/RU2024503C1/ru active
- 1989-08-22 RU SU894614909A patent/RU1836342C/ru active
- 1989-08-22 NO NO893376A patent/NO171784C/no unknown
- 1989-08-23 KR KR1019890701592A patent/KR900700442A/ko not_active Application Discontinuation
-
1990
- 1990-02-02 YU YU00196/90A patent/YU19690A/xx unknown
-
1991
- 1991-01-18 US US07/643,161 patent/US5155133A/en not_active Expired - Fee Related
- 1991-04-22 RU SU914895329A patent/RU1836343C/ru active
-
1992
- 1992-11-12 GR GR920402579T patent/GR3006241T3/el unknown
-
1993
- 1993-01-28 GR GR930400159T patent/GR3006912T3/el unknown
- 1993-06-30 LV LV930851A patent/LV10250A/xx unknown
- 1993-12-28 LT LTIP1687A patent/LTIP1687A/xx not_active Application Discontinuation
- 1993-12-28 LT LTIP1688A patent/LTIP1688A/xx not_active Application Discontinuation
- 1993-12-30 LT LTIP1720A patent/LTIP1720A/xx not_active Application Discontinuation
- 1993-12-31 LT LTIP1752A patent/LTIP1752A/xx not_active Application Discontinuation
-
1994
- 1994-05-31 CN CN94105497A patent/CN1097736A/zh active Pending
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