SK282202B6 - Derivát kyseliny benzoovej substituovanej v orto polohe, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents
Derivát kyseliny benzoovej substituovanej v orto polohe, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDFInfo
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- SK282202B6 SK282202B6 SK1054-95A SK105495A SK282202B6 SK 282202 B6 SK282202 B6 SK 282202B6 SK 105495 A SK105495 A SK 105495A SK 282202 B6 SK282202 B6 SK 282202B6
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- Prior art keywords
- acid
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- formula
- chloro
- methyl
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- 150000001558 benzoic acid derivatives Chemical class 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000005711 Benzoic acid Substances 0.000 claims abstract 2
- 235000010233 benzoic acid Nutrition 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 COA Chemical group 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 58
- 238000011282 treatment Methods 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 102000003669 Antiporters Human genes 0.000 claims description 7
- 108090000084 Antiporters Proteins 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000000543 intermediate Substances 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 230000003449 preventive effect Effects 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000003797 solvolysis reaction Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 230000006793 arrhythmia Effects 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 2
- YNYSKRCZLQPSHY-UHFFFAOYSA-N 4-bromo-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(Br)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N YNYSKRCZLQPSHY-UHFFFAOYSA-N 0.000 claims description 2
- XJOYGWNOFSHSAG-UHFFFAOYSA-N 4-chloro-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(Cl)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N XJOYGWNOFSHSAG-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- PBZXNBOUKGUDDT-UHFFFAOYSA-N 4-chloro-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound CCC1=CC(Cl)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N PBZXNBOUKGUDDT-UHFFFAOYSA-N 0.000 claims 1
- QLWBIUBEALCZGB-UHFFFAOYSA-N 4-cyano-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(C#N)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N QLWBIUBEALCZGB-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 238000005957 chlorosulfonylation reaction Methods 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- RZIVXSRWYPNDGP-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-fluoro-5-methylsulfonylbenzamide Chemical compound CCC1=CC(F)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N RZIVXSRWYPNDGP-UHFFFAOYSA-N 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 241000972349 Ocoa Species 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 30
- 150000004702 methyl esters Chemical class 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 5
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- ODSUNGPMHBSXNU-UHFFFAOYSA-N 2,4-dichloro-5-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1Cl ODSUNGPMHBSXNU-UHFFFAOYSA-N 0.000 description 4
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 230000007654 ischemic lesion Effects 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
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- HYZINPTYZLTBOR-UHFFFAOYSA-N methyl 2,4-dichloro-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(Cl)C=C1Cl HYZINPTYZLTBOR-UHFFFAOYSA-N 0.000 description 1
- VCRWILYAWSRHBN-UHFFFAOYSA-N methyl 2,4-dichlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1Cl VCRWILYAWSRHBN-UHFFFAOYSA-N 0.000 description 1
- KYYNJKIBAXJQBU-UHFFFAOYSA-N methyl 2,4-difluoro-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(F)C=C1F KYYNJKIBAXJQBU-UHFFFAOYSA-N 0.000 description 1
- KYIVIIGLHCFLJV-UHFFFAOYSA-N methyl 2-(difluoromethyl)-4-formyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(C=O)C=C1C(F)F KYIVIIGLHCFLJV-UHFFFAOYSA-N 0.000 description 1
- PYBNOKXWYDPAMR-UHFFFAOYSA-N methyl 2-(fluoromethyl)-4-formyl-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(C=O)C=C1CF PYBNOKXWYDPAMR-UHFFFAOYSA-N 0.000 description 1
- JCUWFYRXNNSGLJ-UHFFFAOYSA-N methyl 2-bromo-4-fluoro-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(F)C=C1Br JCUWFYRXNNSGLJ-UHFFFAOYSA-N 0.000 description 1
- DKZHZXXFAJQUCP-UHFFFAOYSA-N methyl 2-bromo-4-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(C)C=C1Br DKZHZXXFAJQUCP-UHFFFAOYSA-N 0.000 description 1
- SZXDOVSDZDQXJW-UHFFFAOYSA-N methyl 2-cyano-4-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(C)C=C1C#N SZXDOVSDZDQXJW-UHFFFAOYSA-N 0.000 description 1
- RZGPEDXYULNBSB-UHFFFAOYSA-N methyl 2-ethyl-4-fluoro-5-methylsulfonylbenzoate Chemical compound CCC1=CC(F)=C(S(C)(=O)=O)C=C1C(=O)OC RZGPEDXYULNBSB-UHFFFAOYSA-N 0.000 description 1
- GHDGXTVEHXMNMV-UHFFFAOYSA-N methyl 2-ethyl-4-fluoro-5-sulfamoylbenzoate Chemical compound CCC1=CC(F)=C(S(N)(=O)=O)C=C1C(=O)OC GHDGXTVEHXMNMV-UHFFFAOYSA-N 0.000 description 1
- REEOKSUGNPPFEO-UHFFFAOYSA-N methyl 2-ethynyl-4-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(C)C=C1C#C REEOKSUGNPPFEO-UHFFFAOYSA-N 0.000 description 1
- IDXRFFZXEIWTLY-UHFFFAOYSA-N methyl 4-bromo-2-ethyl-5-methylsulfonylbenzoate Chemical compound CCC1=CC(Br)=C(S(C)(=O)=O)C=C1C(=O)OC IDXRFFZXEIWTLY-UHFFFAOYSA-N 0.000 description 1
- SXLHIYDNPUMCIC-UHFFFAOYSA-N methyl 4-bromo-2-ethyl-5-sulfamoylbenzoate Chemical compound CCC1=CC(Br)=C(S(N)(=O)=O)C=C1C(=O)OC SXLHIYDNPUMCIC-UHFFFAOYSA-N 0.000 description 1
- YLMYKTNVIPVWKR-UHFFFAOYSA-N methyl 4-bromo-2-methoxy-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(Br)C=C1OC YLMYKTNVIPVWKR-UHFFFAOYSA-N 0.000 description 1
- XGPLNHHOOREOPD-UHFFFAOYSA-N methyl 4-bromo-2-methyl-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(Br)C=C1C XGPLNHHOOREOPD-UHFFFAOYSA-N 0.000 description 1
- POQSLNRGPHUGIM-UHFFFAOYSA-N methyl 4-bromo-2-nitro-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(Br)C=C1[N+]([O-])=O POQSLNRGPHUGIM-UHFFFAOYSA-N 0.000 description 1
- FZEWAYVVHAMCCB-UHFFFAOYSA-N methyl 4-bromo-2-propyl-5-sulfamoylbenzoate Chemical compound CCCC1=CC(Br)=C(S(N)(=O)=O)C=C1C(=O)OC FZEWAYVVHAMCCB-UHFFFAOYSA-N 0.000 description 1
- ZPXDXHKNAFIQTG-UHFFFAOYSA-N methyl 4-chloro-2-(difluoromethyl)-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(Cl)C=C1C(F)F ZPXDXHKNAFIQTG-UHFFFAOYSA-N 0.000 description 1
- RIFVYMHJOXBNJI-UHFFFAOYSA-N methyl 4-chloro-2-cyano-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1C#N RIFVYMHJOXBNJI-UHFFFAOYSA-N 0.000 description 1
- NZQFZGFJDFKWNO-UHFFFAOYSA-N methyl 4-chloro-2-methoxy-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(Cl)C=C1OC NZQFZGFJDFKWNO-UHFFFAOYSA-N 0.000 description 1
- PPULCCHGLQOQQW-UHFFFAOYSA-N methyl 4-chloro-2-propan-2-yl-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1C(C)C PPULCCHGLQOQQW-UHFFFAOYSA-N 0.000 description 1
- IPQHNKPCTMMTLI-UHFFFAOYSA-N methyl 4-chloro-3-sulfamoylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 IPQHNKPCTMMTLI-UHFFFAOYSA-N 0.000 description 1
- PUDQBGQCWOZCGP-UHFFFAOYSA-N methyl 4-fluoro-2-(1,1,2,2,2-pentafluoroethyl)-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(F)C=C1C(F)(F)C(F)(F)F PUDQBGQCWOZCGP-UHFFFAOYSA-N 0.000 description 1
- QOGWKVLBWXCHPD-UHFFFAOYSA-N methyl 4-fluoro-2-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(F)C=C1C QOGWKVLBWXCHPD-UHFFFAOYSA-N 0.000 description 1
- YBAZOLISUXINHV-UHFFFAOYSA-N methyl 4-fluoro-2-nitrobenzoate Chemical compound COC(=O)C1=CC=C(F)C=C1[N+]([O-])=O YBAZOLISUXINHV-UHFFFAOYSA-N 0.000 description 1
- DGXXWVYWUSEYGO-UHFFFAOYSA-N methyl 4-fluoro-2-propan-2-yl-5-sulfamoylbenzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(F)C=C1C(C)C DGXXWVYWUSEYGO-UHFFFAOYSA-N 0.000 description 1
- JALZDNAUFWCHBV-UHFFFAOYSA-N methyl 4-fluoro-5-sulfamoyl-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(S(N)(=O)=O)=C(F)C=C1C(F)(F)F JALZDNAUFWCHBV-UHFFFAOYSA-N 0.000 description 1
- LSILKKYOSCLZRW-UHFFFAOYSA-N methyl 5-(benzenesulfonyl)-4-chloro-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1Cl LSILKKYOSCLZRW-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- IFCXSOAGVXFIJI-UHFFFAOYSA-N n-(diaminomethylidene)-4-fluoro-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(F)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N IFCXSOAGVXFIJI-UHFFFAOYSA-N 0.000 description 1
- COPUVNKZAUGSHL-UHFFFAOYSA-N n-(diaminomethylidene)-4-fluoro-5-methylsulfonyl-2-(1,1,2,2,2-pentafluoroethyl)benzamide Chemical compound CS(=O)(=O)C1=CC(C(=O)N=C(N)N)=C(C(F)(F)C(F)(F)F)C=C1F COPUVNKZAUGSHL-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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- 230000003204 osmotic effect Effects 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000037921 secondary disease Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
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- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C317/50—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4430212A DE4430212A1 (de) | 1994-08-28 | 1994-08-28 | Ortho-substituierte Benzoesäure-Derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK105495A3 SK105495A3 (en) | 1996-03-06 |
| SK282202B6 true SK282202B6 (sk) | 2001-12-03 |
Family
ID=6526569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1054-95A SK282202B6 (sk) | 1994-08-28 | 1995-08-25 | Derivát kyseliny benzoovej substituovanej v orto polohe, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5849796A (cs) |
| EP (1) | EP0704431B1 (cs) |
| JP (1) | JPH0859602A (cs) |
| KR (1) | KR100406686B1 (cs) |
| CN (1) | CN1068587C (cs) |
| AT (1) | ATE193282T1 (cs) |
| AU (1) | AU703633B2 (cs) |
| BR (1) | BR9503817A (cs) |
| CA (1) | CA2156959A1 (cs) |
| CZ (1) | CZ289492B6 (cs) |
| DE (2) | DE4430212A1 (cs) |
| DK (1) | DK0704431T3 (cs) |
| ES (1) | ES2147810T3 (cs) |
| GR (1) | GR3033989T3 (cs) |
| HU (1) | HUT74946A (cs) |
| NO (1) | NO305794B1 (cs) |
| PL (1) | PL181183B1 (cs) |
| PT (1) | PT704431E (cs) |
| RU (1) | RU2125981C1 (cs) |
| SK (1) | SK282202B6 (cs) |
| TW (1) | TW406067B (cs) |
| UA (1) | UA44238C2 (cs) |
| ZA (1) | ZA957161B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19713427A1 (de) * | 1997-04-01 | 1998-10-08 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19919349A1 (de) * | 1999-04-28 | 2000-11-02 | Merck Patent Gmbh | Verfahren zur Herstellung eines Benzoylguanidinderivates |
| AU2001293555A1 (en) * | 2000-09-21 | 2002-04-02 | Novation Pharmaceuticals Inc. | Benzoic acid derivatives and uses thereof |
| HUP0401963A3 (en) * | 2001-08-09 | 2006-01-30 | Ono Pharmaceutical Co | Carboxylic acid derivative compounds and drugs comprising these compounds as the active ingredient |
| US8980952B2 (en) * | 2002-03-20 | 2015-03-17 | University Of Maryland, Baltimore | Methods for treating brain swelling with a compound that blocks a non-selective cation channel |
| SI2438913T1 (sl) | 2002-03-20 | 2020-10-30 | University Of Maryland, Baltimore | Neselektivni kationski kanal v nevralnih celicah in spojine, ki blokirajo kanal, za uporabo pri zdravljenju otekanja možganov |
| EP2359832A3 (en) * | 2004-09-18 | 2011-11-23 | University of Maryland, Baltimore | Therapeutic agents targeting the NCCA-ATP channel and methods of use thereof |
| EP1799227B1 (en) | 2004-09-18 | 2010-11-10 | University of Maryland, Baltimore | Therapeutic agents targeting the nc ca-atp channel and methods of use thereof |
| EP1893612B1 (en) * | 2005-06-22 | 2011-08-03 | Plexxikon, Inc. | Pyrrolo [2, 3-b]pyridine derivatives as protein kinase inhibitors |
| EP3103451A1 (en) * | 2007-01-12 | 2016-12-14 | University of Maryland, Baltimore | Targetting ncca-atp channel for organ protection following ischemic episode |
| WO2008098160A1 (en) * | 2007-02-09 | 2008-08-14 | University Of Maryland, Baltimore | Antagonists of a non-selective cation channel in neural cells |
| CA2974689C (en) | 2007-06-22 | 2020-02-25 | The United States Of America As Represented By The Department Of Veters Affairs | Inhibitors of ncca-atp channels for therapy |
| LT6401B (lt) * | 2015-07-28 | 2017-06-12 | Vilniaus Universitetas | Karboanhidrazės selektyvūs inhibitoriai |
| CN105732357A (zh) * | 2016-03-23 | 2016-07-06 | 叶芳 | 2-氯-4氟苯甲酸及其制备方法 |
| CN106892852B (zh) * | 2017-03-21 | 2019-07-09 | 重庆医科大学 | 具有抗流感病毒活性的胍基类似物及其制备方法 |
| CN111116395B (zh) * | 2019-12-27 | 2023-04-07 | 湖北工业大学 | 多碘代芳香酸类化合物及其在抗腺病毒7型中的应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3929582A1 (de) * | 1989-09-06 | 1991-03-07 | Hoechst Ag | Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament |
| ES2108144T3 (es) * | 1992-02-15 | 1997-12-16 | Hoechst Ag | Benzoilguanidinas sustituidas en orto, procedimiento para su preparacion, su utilizacion como medicamento o agente de diagnostico, asi como medicamento que las contiene. |
| ATE139526T1 (de) * | 1992-02-15 | 1996-07-15 | Hoechst Ag | 3,5-substituierte benzoylguanidine, mit antiarrythmischer wirkung und inhibierender wirkung auf die proliferationen von zellen |
| ES2092729T3 (es) * | 1992-07-01 | 1996-12-01 | Hoechst Ag | Benzoilguanidinas 3,4,5-sustituidas, procedimiento para su preparacion, su empleo como medicamento o agente de diagnostico, asi como medicamento que las contiene. |
| EP0589336B1 (de) * | 1992-09-22 | 1997-01-08 | Hoechst Aktiengesellschaft | Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika |
| TW250479B (cs) * | 1992-12-15 | 1995-07-01 | Hoechst Ag | |
| DE4404183A1 (de) * | 1994-02-10 | 1995-08-17 | Merck Patent Gmbh | 4-Amino-1-piperidylbenzoylguanidine |
| DE4422685A1 (de) * | 1994-06-29 | 1996-01-04 | Hoechst Ag | Ortho-amino-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1994
- 1994-08-28 DE DE4430212A patent/DE4430212A1/de not_active Withdrawn
-
1995
- 1995-07-25 TW TW084107705A patent/TW406067B/zh not_active IP Right Cessation
- 1995-08-18 EP EP95112998A patent/EP0704431B1/de not_active Expired - Lifetime
- 1995-08-18 AT AT95112998T patent/ATE193282T1/de not_active IP Right Cessation
- 1995-08-18 DE DE59508383T patent/DE59508383D1/de not_active Expired - Fee Related
- 1995-08-18 PT PT95112998T patent/PT704431E/pt unknown
- 1995-08-18 ES ES95112998T patent/ES2147810T3/es not_active Expired - Lifetime
- 1995-08-18 DK DK95112998T patent/DK0704431T3/da active
- 1995-08-21 AU AU30145/95A patent/AU703633B2/en not_active Ceased
- 1995-08-23 UA UA95083919A patent/UA44238C2/uk unknown
- 1995-08-25 HU HU9502500A patent/HUT74946A/hu unknown
- 1995-08-25 ZA ZA957161A patent/ZA957161B/xx unknown
- 1995-08-25 CN CN95116623A patent/CN1068587C/zh not_active Expired - Fee Related
- 1995-08-25 RU RU95114389/04A patent/RU2125981C1/ru not_active IP Right Cessation
- 1995-08-25 NO NO953352A patent/NO305794B1/no not_active IP Right Cessation
- 1995-08-25 CA CA002156959A patent/CA2156959A1/en not_active Abandoned
- 1995-08-25 PL PL95310192A patent/PL181183B1/pl not_active IP Right Cessation
- 1995-08-25 CZ CZ19952181A patent/CZ289492B6/cs not_active IP Right Cessation
- 1995-08-25 SK SK1054-95A patent/SK282202B6/sk unknown
- 1995-08-28 KR KR1019950026798A patent/KR100406686B1/ko not_active Expired - Fee Related
- 1995-08-28 BR BR9503817A patent/BR9503817A/pt not_active IP Right Cessation
- 1995-08-28 JP JP7240500A patent/JPH0859602A/ja active Pending
- 1995-08-28 US US08/520,340 patent/US5849796A/en not_active Expired - Fee Related
-
2000
- 2000-07-21 GR GR20000401675T patent/GR3033989T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU3014595A (en) | 1996-03-14 |
| CN1068587C (zh) | 2001-07-18 |
| PT704431E (pt) | 2000-10-31 |
| DE4430212A1 (de) | 1996-02-29 |
| CA2156959A1 (en) | 1996-03-01 |
| EP0704431A3 (de) | 1997-01-29 |
| PL181183B1 (pl) | 2001-06-29 |
| NO305794B1 (no) | 1999-07-26 |
| PL310192A1 (en) | 1996-03-04 |
| EP0704431B1 (de) | 2000-05-24 |
| UA44238C2 (uk) | 2002-02-15 |
| NO953352D0 (no) | 1995-08-25 |
| DK0704431T3 (da) | 2000-09-11 |
| ZA957161B (en) | 1996-04-17 |
| KR100406686B1 (ko) | 2004-07-19 |
| SK105495A3 (en) | 1996-03-06 |
| DE59508383D1 (de) | 2000-06-29 |
| ES2147810T3 (es) | 2000-10-01 |
| CN1125722A (zh) | 1996-07-03 |
| GR3033989T3 (en) | 2000-11-30 |
| EP0704431A2 (de) | 1996-04-03 |
| BR9503817A (pt) | 1996-04-16 |
| JPH0859602A (ja) | 1996-03-05 |
| HU9502500D0 (en) | 1995-10-30 |
| HUT74946A (en) | 1997-03-28 |
| CZ289492B6 (cs) | 2002-02-13 |
| ATE193282T1 (de) | 2000-06-15 |
| AU703633B2 (en) | 1999-03-25 |
| RU2125981C1 (ru) | 1999-02-10 |
| NO953352L (no) | 1996-02-29 |
| US5849796A (en) | 1998-12-15 |
| CZ218195A3 (en) | 1996-03-13 |
| KR960007539A (ko) | 1996-03-22 |
| TW406067B (en) | 2000-09-21 |
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