CA1289563C - Antiarrhythmic imidazoliums, intermediates thereto and method of use - Google Patents
Antiarrhythmic imidazoliums, intermediates thereto and method of useInfo
- Publication number
- CA1289563C CA1289563C CA000458676A CA458676A CA1289563C CA 1289563 C CA1289563 C CA 1289563C CA 000458676 A CA000458676 A CA 000458676A CA 458676 A CA458676 A CA 458676A CA 1289563 C CA1289563 C CA 1289563C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- phenyl
- chloride
- butyl
- imidazolium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003416 antiarrhythmic agent Substances 0.000 title claims abstract description 8
- 230000003288 anthiarrhythmic effect Effects 0.000 title claims description 3
- 238000000034 method Methods 0.000 title abstract description 15
- 239000000543 intermediate Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 172
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
- -1 cyano, nitro, carbamoyl Chemical group 0.000 claims abstract description 44
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 230000006793 arrhythmia Effects 0.000 claims abstract description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 8
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- OXBOABAOQWBSIV-UHFFFAOYSA-N [N]S(N)(=O)=O Chemical compound [N]S(N)(=O)=O OXBOABAOQWBSIV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002905 alkanoylamido group Chemical group 0.000 claims abstract description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 3
- 125000005281 alkyl ureido group Chemical group 0.000 claims abstract description 3
- 125000000958 aryl methylene group Chemical group 0.000 claims abstract description 3
- 125000005605 benzo group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims description 60
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 11
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical group 0.000 claims 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 claims description 8
- VWUCIBOKNZGWLX-UHFFFAOYSA-N 1h-imidazol-1-ium;bromide Chemical compound [Br-].C1=C[NH+]=CN1 VWUCIBOKNZGWLX-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- MHDLDFFDVQDCBT-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-3-pentylimidazol-3-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CCCCCN1C=C[N+](CCCCC=2C=CC(Cl)=CC=2)=C1 MHDLDFFDVQDCBT-UHFFFAOYSA-M 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- PRXAZEUNDFUTNI-UHFFFAOYSA-M dihydrogen phosphate;1-(4,4-diphenylbutyl)-3-heptylimidazol-1-ium Chemical compound OP(O)([O-])=O.CCCCCCCN1C=C[N+](CCCC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 PRXAZEUNDFUTNI-UHFFFAOYSA-M 0.000 claims description 3
- VGVXNRWNPUIDPO-UHFFFAOYSA-M dihydrogen phosphate;1-[4-(4-fluorophenyl)butyl]-3-heptylimidazol-3-ium Chemical compound OP(O)([O-])=O.CCCCCCCN1C=C[N+](CCCCC=2C=CC(F)=CC=2)=C1 VGVXNRWNPUIDPO-UHFFFAOYSA-M 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- SJSRRYHMNQEFCT-UHFFFAOYSA-N n-[4-(1-hydroxy-2-imidazol-1-ylethyl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(O)CN1C=NC=C1 SJSRRYHMNQEFCT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- KGWYOZLMAPDSFT-UHFFFAOYSA-M 1,3-bis[4-(4-chlorophenyl)butyl]imidazol-1-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.C1=CC(Cl)=CC=C1CCCCN1C=[N+](CCCCC=2C=CC(Cl)=CC=2)C=C1 KGWYOZLMAPDSFT-UHFFFAOYSA-M 0.000 claims description 2
- JNCAYPMXKLFYDP-WVLIHFOGSA-M 1-[(e)-4-(4-chlorophenyl)but-2-enyl]-3-heptylimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCCN1C=C[N+](C\C=C\CC=2C=CC(Cl)=CC=2)=C1 JNCAYPMXKLFYDP-WVLIHFOGSA-M 0.000 claims description 2
- HSPARVTWRINLHT-UHFFFAOYSA-M 1-[3-(4-chlorophenyl)propyl]-3-heptylimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCCN1C=C[N+](CCCC=2C=CC(Cl)=CC=2)=C1 HSPARVTWRINLHT-UHFFFAOYSA-M 0.000 claims description 2
- AHZYRJVPPFLQEH-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-2,3-dimethylimidazol-3-ium;chloride Chemical compound [Cl-].CN1C=C[N+](CCCCC=2C=CC(Cl)=CC=2)=C1C AHZYRJVPPFLQEH-UHFFFAOYSA-M 0.000 claims description 2
- VTRWCITVMNSSSF-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-3-(2-phenylethyl)imidazol-1-ium;chloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1CCCC[N+]1=CN(CCC=2C=CC=CC=2)C=C1 VTRWCITVMNSSSF-UHFFFAOYSA-M 0.000 claims description 2
- JHXPEZQZDHPLLS-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-3-(cyclohexylmethyl)imidazol-3-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.C1=CC(Cl)=CC=C1CCCC[N+]1=CN(CC2CCCCC2)C=C1 JHXPEZQZDHPLLS-UHFFFAOYSA-M 0.000 claims description 2
- ZWGDYVUUDBSFFJ-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-3-heptylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCCN1C=C[N+](CCCCC=2C=CC(Cl)=CC=2)=C1 ZWGDYVUUDBSFFJ-UHFFFAOYSA-M 0.000 claims description 2
- HQOVFEXUDGCEMQ-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CN1C=C[N+](CCCCC=2C=CC(Cl)=CC=2)=C1 HQOVFEXUDGCEMQ-UHFFFAOYSA-M 0.000 claims description 2
- MRXOGBBMMQKAQB-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-3-propylimidazol-3-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CCCN1C=C[N+](CCCCC=2C=CC(Cl)=CC=2)=C1 MRXOGBBMMQKAQB-UHFFFAOYSA-M 0.000 claims description 2
- HFRATIAZJJFIHH-UHFFFAOYSA-M 1-[5-(4-chlorophenyl)pentyl]-3-heptylimidazol-1-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CCCCCCCN1C=C[N+](CCCCCC=2C=CC(Cl)=CC=2)=C1 HFRATIAZJJFIHH-UHFFFAOYSA-M 0.000 claims description 2
- LRMLFVXHDNGEGV-UHFFFAOYSA-M 1-butyl-3-[4-(4-chlorophenyl)butyl]imidazol-3-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.C1=[N+](CCCC)C=CN1CCCCC1=CC=C(Cl)C=C1 LRMLFVXHDNGEGV-UHFFFAOYSA-M 0.000 claims description 2
- CSRQQIUPGRWNNW-UHFFFAOYSA-M 1-heptyl-3-(4-phenylbutyl)imidazol-1-ium;chloride Chemical compound [Cl-].C1=[N+](CCCCCCC)C=CN1CCCCC1=CC=CC=C1 CSRQQIUPGRWNNW-UHFFFAOYSA-M 0.000 claims description 2
- XABQAESTGRTRPP-UHFFFAOYSA-M 1-heptyl-3-[4-(4-methoxyphenyl)butyl]-2,4,5-trimethylimidazol-1-ium;bromide Chemical compound [Br-].CC1=[N+](CCCCCCC)C(C)=C(C)N1CCCCC1=CC=C(OC)C=C1 XABQAESTGRTRPP-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims description 2
- PWZNQVNCSLDRIJ-UHFFFAOYSA-M n-(2,6-dimethylphenyl)-2-(3-heptylimidazol-3-ium-1-yl)ethanesulfonamide;bromide Chemical compound [Br-].CCCCCCCN1C=C[N+](CCS(=O)(=O)NC=2C(=CC=CC=2C)C)=C1 PWZNQVNCSLDRIJ-UHFFFAOYSA-M 0.000 claims description 2
- VDEDEXVPAUUOQM-UHFFFAOYSA-N n-[4-[2-(3-ethyl-1,2-dihydroimidazol-1-ium-1-yl)acetyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=C[NH+](CC)CN1CC(=O)C1=CC=C(NS(C)(=O)=O)C=C1 VDEDEXVPAUUOQM-UHFFFAOYSA-N 0.000 claims description 2
- BLRBSWOMJJNFBZ-UHFFFAOYSA-N n-[4-[4-(3-heptylimidazol-3-ium-1-yl)butyl]phenyl]acetamide;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCN1C=C[N+](CCCCC=2C=CC(NC(C)=O)=CC=2)=C1 BLRBSWOMJJNFBZ-UHFFFAOYSA-N 0.000 claims description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 2
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 claims description 2
- 230000001629 suppression Effects 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- XDKIMKJLTFGYJC-UHFFFAOYSA-N n-[4-[1-hydroxy-2-(3-methyl-1,2-dihydroimidazol-1-ium-1-yl)ethyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=CN(C)C[NH+]1CC(O)C1=CC=C(NS(C)(=O)=O)C=C1 XDKIMKJLTFGYJC-UHFFFAOYSA-N 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QRMNVYHFJCGDDI-UHFFFAOYSA-N 1-(4-aminophenyl)-2-imidazol-1-ylethanone Chemical compound C1=CC(N)=CC=C1C(=O)CN1C=NC=C1 QRMNVYHFJCGDDI-UHFFFAOYSA-N 0.000 claims 1
- VDRGBHGQZVADFK-MLBSPLJJSA-M 1-[(e)-4-(4-chlorophenyl)but-3-enyl]-3-heptylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCCN1C=C[N+](CC\C=C\C=2C=CC(Cl)=CC=2)=C1 VDRGBHGQZVADFK-MLBSPLJJSA-M 0.000 claims 1
- PFNNVFMMLQSFLJ-PHZXCRFESA-M 1-[(z)-4-(4-chlorophenyl)but-2-enyl]-3-heptylimidazol-1-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CCCCCCCN1C=C[N+](C\C=C/CC=2C=CC(Cl)=CC=2)=C1 PFNNVFMMLQSFLJ-PHZXCRFESA-M 0.000 claims 1
- AFVNBJWKGIWPNY-UHFFFAOYSA-N 1-[2-(4-nitrophenyl)ethyl]imidazole;hydrochloride Chemical compound Cl.C1=CC([N+](=O)[O-])=CC=C1CCN1C=NC=C1 AFVNBJWKGIWPNY-UHFFFAOYSA-N 0.000 claims 1
- SLQKOGOLCPRPET-UHFFFAOYSA-M 1-[4-(2,3-dichlorophenyl)but-2-enyl]-3-heptylimidazol-1-ium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCN1C=C[N+](CC=CCC=2C(=C(Cl)C=CC=2)Cl)=C1 SLQKOGOLCPRPET-UHFFFAOYSA-M 0.000 claims 1
- JYVOYXQCCSHLQU-UHFFFAOYSA-M 1-[4-(2-chlorophenyl)but-2-enyl]-3-heptylimidazol-1-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CCCCCCCN1C=C[N+](CC=CCC=2C(=CC=CC=2)Cl)=C1 JYVOYXQCCSHLQU-UHFFFAOYSA-M 0.000 claims 1
- YSGFQQUUQWATFB-UHFFFAOYSA-M 1-[4-(2-chlorophenyl)butyl]-3-heptylimidazol-3-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CCCCCCCN1C=C[N+](CCCCC=2C(=CC=CC=2)Cl)=C1 YSGFQQUUQWATFB-UHFFFAOYSA-M 0.000 claims 1
- QYUYEJWHMHSCGS-UHFFFAOYSA-M 1-[4-(4-chlorophenyl)butyl]-3-heptyl-2-methylimidazol-3-ium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CCCCCCCN1C=C[N+](CCCCC=2C=CC(Cl)=CC=2)=C1C QYUYEJWHMHSCGS-UHFFFAOYSA-M 0.000 claims 1
- QLYILMSWAFDPHM-UHFFFAOYSA-N 1-[4-(4-nitrophenyl)butyl]imidazole;hydrochloride Chemical compound Cl.C1=CC([N+](=O)[O-])=CC=C1CCCCN1C=NC=C1 QLYILMSWAFDPHM-UHFFFAOYSA-N 0.000 claims 1
- PPMFYXOKYRKJLZ-UHFFFAOYSA-M 1-[5-(4-chlorophenyl)pentan-2-yl]-3-heptylimidazol-3-ium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCN1C=C[N+](C(C)CCCC=2C=CC(Cl)=CC=2)=C1 PPMFYXOKYRKJLZ-UHFFFAOYSA-M 0.000 claims 1
- VCWLKTIOIFNUKB-UHFFFAOYSA-M 1-butyl-3-[3-(4-methoxyphenyl)propyl]imidazol-3-ium;bromide Chemical compound [Br-].C1=[N+](CCCC)C=CN1CCCC1=CC=C(OC)C=C1 VCWLKTIOIFNUKB-UHFFFAOYSA-M 0.000 claims 1
- DEKSMSKFLWGVGF-UHFFFAOYSA-M 1-heptyl-3-[3-(4-methoxyphenyl)propyl]imidazol-3-ium;bromide Chemical compound [Br-].C1=[N+](CCCCCCC)C=CN1CCCC1=CC=C(OC)C=C1 DEKSMSKFLWGVGF-UHFFFAOYSA-M 0.000 claims 1
- YVCRYMWTIWGBMO-UHFFFAOYSA-M 1-heptyl-3-[4-(4-methoxyphenyl)butyl]-2-methylimidazol-1-ium;bromide Chemical compound [Br-].CC1=[N+](CCCCCCC)C=CN1CCCCC1=CC=C(OC)C=C1 YVCRYMWTIWGBMO-UHFFFAOYSA-M 0.000 claims 1
- ZVIHNCZGSKQKDH-UHFFFAOYSA-M 1-heptyl-3-[4-(4-methoxyphenyl)butyl]imidazol-1-ium;bromide Chemical compound [Br-].C1=[N+](CCCCCCC)C=CN1CCCCC1=CC=C(OC)C=C1 ZVIHNCZGSKQKDH-UHFFFAOYSA-M 0.000 claims 1
- NCSHDJZAOSCRPM-UHFFFAOYSA-N 2-imidazol-1-yl-1-(4-nitrophenyl)ethanol Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)CN1C=CN=C1 NCSHDJZAOSCRPM-UHFFFAOYSA-N 0.000 claims 1
- UWMYYVKXEQTENE-UHFFFAOYSA-N 2-imidazol-1-yl-1-(4-nitrophenyl)ethanone;hydrochloride Chemical compound [Cl-].C1=CC([N+](=O)[O-])=CC=C1C(=O)C[NH+]1C=NC=C1 UWMYYVKXEQTENE-UHFFFAOYSA-N 0.000 claims 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- 230000002763 arrhythmic effect Effects 0.000 claims 1
- DWBSIOQWXMDIGW-UHFFFAOYSA-M dihydrogen phosphate;n-[4-[4-(3-heptylimidazol-3-ium-1-yl)butyl]phenyl]methanesulfonamide Chemical compound OP(O)([O-])=O.C1=[N+](CCCCCCC)C=CN1CCCCC1=CC=C(NS(C)(=O)=O)C=C1 DWBSIOQWXMDIGW-UHFFFAOYSA-M 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- ZPCJNANSSQAFKD-UHFFFAOYSA-M n-(2,6-dimethylphenyl)-3-(3-heptylimidazol-1-ium-1-yl)propane-1-sulfonamide;chloride Chemical compound [Cl-].CCCCCCCN1C=C[N+](CCCS(=O)(=O)NC=2C(=CC=CC=2C)C)=C1 ZPCJNANSSQAFKD-UHFFFAOYSA-M 0.000 claims 1
- BFYOQCIUAUMPRK-UHFFFAOYSA-N n-[4-(2-imidazol-1-ylacetyl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(=O)CN1C=NC=C1 BFYOQCIUAUMPRK-UHFFFAOYSA-N 0.000 claims 1
- VBRDUUVTHASFTO-UHFFFAOYSA-N n-[4-(2-imidazol-1-ylethyl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCN1C=NC=C1 VBRDUUVTHASFTO-UHFFFAOYSA-N 0.000 claims 1
- ZORXVZAGXWYGBJ-UHFFFAOYSA-N n-[4-[1-hydroxy-2-(3-methyl-1,2-dihydroimidazol-1-ium-1-yl)ethyl]phenyl]ethanesulfonamide;chloride Chemical compound [Cl-].C1=CC(NS(=O)(=O)CC)=CC=C1C(O)C[NH+]1C=CN(C)C1 ZORXVZAGXWYGBJ-UHFFFAOYSA-N 0.000 claims 1
- MWCVHGFYPKZHOA-UHFFFAOYSA-N n-[4-[1-hydroxy-2-(3-propan-2-yl-1,2-dihydroimidazol-1-ium-1-yl)ethyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=CN(C(C)C)C[NH+]1CC(O)C1=CC=C(NS(C)(=O)=O)C=C1 MWCVHGFYPKZHOA-UHFFFAOYSA-N 0.000 claims 1
- ULECSXIQXHLADX-UHFFFAOYSA-N n-[4-[1-hydroxy-3-(3-methyl-1,2-dihydroimidazol-1-ium-1-yl)propyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=CN(C)C[NH+]1CCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ULECSXIQXHLADX-UHFFFAOYSA-N 0.000 claims 1
- HPYZLMULICSEAY-UHFFFAOYSA-N n-[4-[2-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)ethyl]phenyl]methanesulfonamide;iodide Chemical compound [I-].C1=C[NH+](C)CN1CCC1=CC=C(NS(C)(=O)=O)C=C1 HPYZLMULICSEAY-UHFFFAOYSA-N 0.000 claims 1
- RFRBQKRDLOOEIQ-UHFFFAOYSA-N n-[4-[2-(2,3-dimethyl-1,2-dihydroimidazol-1-ium-1-yl)acetyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=C[NH+](C)C(C)N1CC(=O)C1=CC=C(NS(C)(=O)=O)C=C1 RFRBQKRDLOOEIQ-UHFFFAOYSA-N 0.000 claims 1
- WHSUDQRJNHLTSW-UHFFFAOYSA-N n-[4-[2-(3-methyl-1,2-dihydroimidazol-1-ium-1-yl)acetyl]phenyl]ethanesulfonamide;chloride Chemical compound [Cl-].C1=CC(NS(=O)(=O)CC)=CC=C1C(=O)C[NH+]1C=CN(C)C1 WHSUDQRJNHLTSW-UHFFFAOYSA-N 0.000 claims 1
- FNIDTTSCZVNZOP-UHFFFAOYSA-N n-[4-[2-(3-propan-2-ylimidazol-1-ium-1-yl)acetyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=[N+](C(C)C)C=CN1CC(=O)C1=CC=C(NS(C)(=O)=O)C=C1 FNIDTTSCZVNZOP-UHFFFAOYSA-N 0.000 claims 1
- WVMJEUYEKVCBPC-UHFFFAOYSA-N n-[4-[3-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)propanoyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=C[NH+](C)CN1CCC(=O)C1=CC=C(NS(C)(=O)=O)C=C1 WVMJEUYEKVCBPC-UHFFFAOYSA-N 0.000 claims 1
- NRGBKENLRKIKRI-UHFFFAOYSA-N n-[4-[3-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)propyl]phenyl]methanesulfonamide;chloride Chemical compound [Cl-].C1=C[NH+](C)CN1CCCC1=CC=C(NS(C)(=O)=O)C=C1 NRGBKENLRKIKRI-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
- C07C33/483—Monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Gas Separation By Absorption (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/513,143 US4581370A (en) | 1983-07-12 | 1983-07-12 | Antiarrhythmic imidazoliums |
| US513,143 | 1983-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1289563C true CA1289563C (en) | 1991-09-24 |
Family
ID=24042059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000458676A Expired - Lifetime CA1289563C (en) | 1983-07-12 | 1984-07-11 | Antiarrhythmic imidazoliums, intermediates thereto and method of use |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4581370A (enExample) |
| EP (1) | EP0131302B1 (enExample) |
| JP (1) | JPH08815B2 (enExample) |
| AT (1) | ATE72238T1 (enExample) |
| AU (1) | AU582538B2 (enExample) |
| CA (1) | CA1289563C (enExample) |
| DE (1) | DE3485488D1 (enExample) |
| DK (1) | DK339184A (enExample) |
| FI (1) | FI90232C (enExample) |
| GR (1) | GR82282B (enExample) |
| IE (1) | IE59337B1 (enExample) |
| IL (1) | IL72354A (enExample) |
| NO (1) | NO168300C (enExample) |
| NZ (1) | NZ208831A (enExample) |
| ZA (1) | ZA845410B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0149976A3 (de) * | 1983-12-30 | 1986-12-10 | Ciba-Geigy Ag | Substituierte Imidazole |
| US4609670A (en) * | 1984-11-13 | 1986-09-02 | Eli Lilly And Company | Imidazolium hypoglycemic agents |
| EP0200947B1 (de) * | 1985-04-26 | 1990-09-12 | F. Hoffmann-La Roche Ag | 1,3-Disubstituierte Imidazoliumsalze |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| GB8609331D0 (en) * | 1986-04-16 | 1986-05-21 | Pfizer Ltd | Anti-arrythmia agents |
| GB8707120D0 (en) * | 1987-03-25 | 1987-04-29 | Pfizer Ltd | Antiarrhythmic agents |
| EP0291172B1 (en) * | 1987-04-14 | 1992-11-19 | Glaxo Group Limited | Ketone derivatives |
| GB8720693D0 (en) * | 1987-09-03 | 1987-10-07 | Glaxo Group Ltd | Chemical compounds |
| HU221317B1 (en) * | 1991-08-14 | 2002-09-28 | Procter & Gamble Pharma | 2,4-imidazolidinedione derivatives and antiarrhythmic and antifibrillatory compositions containing them, and process for producing them |
| CZ283323B6 (cs) * | 1991-08-14 | 1998-02-18 | Procter And Gamble Pharmaceuticals, Inc. | Cyklické urethany použitelné jako antiarytmická a antifibrilační činidla a farmaceutické přípravky, které je obsahují |
| JPH06509803A (ja) * | 1991-08-14 | 1994-11-02 | プロクター、エンド、ギャンブル、ファーマスーティカルズ、インコーポレーテッド | 抗不整脈及び抗細動剤として有用な新規環状尿素類 |
| US5635521A (en) * | 1991-09-23 | 1997-06-03 | Sandoz Ltd. | Imidazolylmethyl-pyridines |
| ZA929788B (en) * | 1991-12-18 | 1993-06-22 | Schering Corp | Imidazolyl or imidazoylalkyl substituted with a four or five membered nitrogen containing heterocyclic ring. |
| GB9127304D0 (en) * | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| US5183813A (en) * | 1992-02-19 | 1993-02-02 | Sterling Winthrop Inc. | Antiarrhythmic agents |
| US6031109A (en) * | 1993-06-22 | 2000-02-29 | Knoll Aktiengesellschaft | Phenoxy-, phenylthio-, benzoyl-alkyleneaminoalkylene-imidazole derivatives as therapeutic agents |
| GB9312893D0 (en) * | 1993-06-22 | 1993-08-04 | Boots Co Plc | Therapeutic agents |
| FR2766178B1 (fr) * | 1997-07-16 | 2000-03-17 | Oreal | Nouvelles bases d'oxydation cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture |
| FR2766179B1 (fr) * | 1997-07-16 | 2000-03-17 | Oreal | Nouvelles bases d'oxydation cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture |
| FR2782718B1 (fr) * | 1998-09-02 | 2000-11-10 | Oreal | Nouveaux composes cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture |
| FR2782719B1 (fr) * | 1998-09-02 | 2000-11-10 | Oreal | Nouvelles orthophenylenediamines cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture |
| JP4620286B2 (ja) * | 2001-06-05 | 2011-01-26 | 富士フイルム株式会社 | 電解質組成物、光電変換素子及び光電気化学電池 |
| BR0309014A (pt) | 2002-04-08 | 2005-01-11 | Glaxo Group Ltd | ácido(2-((2-alcóxi)-fenil)-ciclopent-1-enil)carbo e heterocìclico aromático e derivados |
| GB0225548D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| JP2008133248A (ja) * | 2006-10-24 | 2008-06-12 | Sanyo Chem Ind Ltd | イミダゾリウム塩の製造方法 |
| RU2373934C1 (ru) * | 2008-03-19 | 2009-11-27 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Применение производных глутаровой кислоты или их фармацевтически приемлемых солей в качестве противоаритмических средств |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2493318A (en) * | 1945-07-14 | 1950-01-03 | Lilly Co Eli | Imidazolium compounds |
| FR8357M (enExample) * | 1966-09-08 | 1971-02-08 | ||
| SE7600674L (sv) * | 1975-02-05 | 1976-08-06 | Rohm & Haas | Fungicider |
| DE2510525C3 (de) * | 1975-03-11 | 1978-03-30 | Th. Goldschmidt Ag, 4300 Essen | Quartäre 2-Alkylimidazoliumsalze |
| AT370095B (de) * | 1977-10-19 | 1983-02-25 | Wellcome Found | Verfahren zum herstellen von neuen 1-aryl-alkyl-imidazolderivaten und deren salzen |
| JPS5479278A (en) * | 1977-12-05 | 1979-06-25 | Nippon Soda Co Ltd | Imidazolium halide |
| IT1097314B (it) * | 1978-07-26 | 1985-08-31 | Recordati Chem Pharm | Derivati dell'imidazolo ad attivita' anticonvulsivante |
| FR2486079A1 (fr) * | 1980-07-07 | 1982-01-08 | Rhone Poulenc Agrochimie | Sels quaternaires d'alcoyl-1-imidazolium de l'acide phosphoreux ou ses monoesters, procedes pour les preparer et compositions fongicides les contenant |
| JPS5838261A (ja) * | 1981-08-29 | 1983-03-05 | Kissei Pharmaceut Co Ltd | 新規な１，３−二置換イミダゾ−ル誘導体及びその製造方法 |
| JPS5855466A (ja) * | 1981-09-28 | 1983-04-01 | Kissei Pharmaceut Co Ltd | 新規な１，３−二置換イミダゾ−ル誘導体及びその製造方法 |
| DE3319845A1 (de) * | 1983-06-01 | 1984-12-06 | Basf Ag, 6700 Ludwigshafen | Arylalkylimidazolium- und -triazoliumsalze, verfahren zu ihrer herstellung und ihre verwendung als mikrozide |
-
1983
- 1983-07-12 US US06/513,143 patent/US4581370A/en not_active Expired - Fee Related
-
1984
- 1984-07-09 AT AT84108015T patent/ATE72238T1/de not_active IP Right Cessation
- 1984-07-09 IL IL72354A patent/IL72354A/xx not_active IP Right Cessation
- 1984-07-09 DE DE8484108015T patent/DE3485488D1/de not_active Expired - Lifetime
- 1984-07-09 NZ NZ208831A patent/NZ208831A/xx unknown
- 1984-07-09 EP EP84108015A patent/EP0131302B1/en not_active Expired - Lifetime
- 1984-07-10 DK DK339184A patent/DK339184A/da not_active Application Discontinuation
- 1984-07-10 FI FI842760A patent/FI90232C/fi not_active IP Right Cessation
- 1984-07-11 CA CA000458676A patent/CA1289563C/en not_active Expired - Lifetime
- 1984-07-11 IE IE177484A patent/IE59337B1/en not_active IP Right Cessation
- 1984-07-11 NO NO842835A patent/NO168300C/no unknown
- 1984-07-11 GR GR75280A patent/GR82282B/el unknown
- 1984-07-12 JP JP59143414A patent/JPH08815B2/ja not_active Expired - Lifetime
- 1984-07-12 AU AU30543/84A patent/AU582538B2/en not_active Ceased
- 1984-07-12 ZA ZA845410A patent/ZA845410B/xx unknown
-
1986
- 1986-07-03 US US06/881,760 patent/US4689341A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0131302A2 (en) | 1985-01-16 |
| IE841774L (en) | 1985-01-12 |
| IL72354A0 (en) | 1984-11-30 |
| JPS6038366A (ja) | 1985-02-27 |
| US4581370A (en) | 1986-04-08 |
| NO842835L (no) | 1985-01-14 |
| NO168300C (no) | 1992-02-05 |
| DE3485488D1 (de) | 1992-03-12 |
| NO168300B (no) | 1991-10-28 |
| EP0131302A3 (en) | 1987-06-16 |
| ZA845410B (en) | 1985-02-27 |
| IE59337B1 (en) | 1994-02-09 |
| NZ208831A (en) | 1988-09-29 |
| EP0131302B1 (en) | 1992-01-29 |
| DK339184A (da) | 1985-01-13 |
| IL72354A (en) | 1988-11-30 |
| AU582538B2 (en) | 1989-04-06 |
| DK339184D0 (da) | 1984-07-10 |
| ATE72238T1 (de) | 1992-02-15 |
| FI842760A0 (fi) | 1984-07-10 |
| AU3054384A (en) | 1985-01-17 |
| GR82282B (enExample) | 1984-12-13 |
| FI842760A7 (fi) | 1985-01-13 |
| FI90232C (fi) | 1994-01-10 |
| US4689341A (en) | 1987-08-25 |
| FI90232B (fi) | 1993-09-30 |
| JPH08815B2 (ja) | 1996-01-10 |
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Legal Events
| Date | Code | Title | Description |
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| MKLA | Lapsed |