SK281661B6 - Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

Info

Publication number

SK281661B6

SK281661B6 SK1033-96A SK103396A SK281661B6 SK 281661 B6 SK281661 B6 SK 281661B6 SK 103396 A SK103396 A SK 103396A SK 281661 B6 SK281661 B6 SK 281661B6

Authority

SK

Slovakia

Prior art keywords

diaminomethylene

formula

methyl

ethyl

methylsulfonylbenzamide

Prior art date

1995-08-11

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 14
• XOFVXSMENNKBRH-UHFFFAOYSA-N n-[amino-(sulfinylamino)methylidene]benzamide Chemical class O=S=NC(N)=NC(=O)C1=CC=CC=C1 XOFVXSMENNKBRH-UHFFFAOYSA-N 0.000 title claims abstract description 13
• 238000002360 preparation method Methods 0.000 title claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 79
• 238000011282 treatment Methods 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 238000004519 manufacturing process Methods 0.000 claims abstract description 11
• LAGJGWGBDKKIQX-UHFFFAOYSA-N n-[amino-(sulfonylamino)methylidene]benzamide Chemical compound O=S(=O)=NC(N)=NC(=O)C1=CC=CC=C1 LAGJGWGBDKKIQX-UHFFFAOYSA-N 0.000 claims abstract description 11
• 201000010099 disease Diseases 0.000 claims abstract description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
• 102000003669 Antiporters Human genes 0.000 claims abstract description 6
• 108090000084 Antiporters Proteins 0.000 claims abstract description 6
• 206010003119 arrhythmia Diseases 0.000 claims abstract description 6
• 230000008569 process Effects 0.000 claims abstract description 5
• 230000006793 arrhythmia Effects 0.000 claims abstract description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 20
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 16
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 16
• 239000000460 chlorine Substances 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 206010061216 Infarction Diseases 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 230000007574 infarction Effects 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• GROMEQPXDKRRIE-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4,5-bis(methylsulfonyl)benzamide Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N GROMEQPXDKRRIE-UHFFFAOYSA-N 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• RSKNQTWLPWOKCV-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O RSKNQTWLPWOKCV-UHFFFAOYSA-N 0.000 claims description 3
• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 239000011630 iodine Substances 0.000 claims description 3
• 238000001465 metallisation Methods 0.000 claims description 3
• 238000011321 prophylaxis Methods 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• BJWRCFVWJBOFDD-UHFFFAOYSA-N 4-tert-butylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(S(=O)(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N BJWRCFVWJBOFDD-UHFFFAOYSA-N 0.000 claims description 2
• 238000010306 acid treatment Methods 0.000 claims description 2
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
• 238000006478 transmetalation reaction Methods 0.000 claims description 2
• UJURHIFLDARYMY-UHFFFAOYSA-N 4-cyclohexylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C2CCCCC2)=C1S(C)(=O)=O UJURHIFLDARYMY-UHFFFAOYSA-N 0.000 claims 1
• XNFHCESYDYHGSU-UHFFFAOYSA-N 4-cyclopentylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C2CCCC2)=C1S(C)(=O)=O XNFHCESYDYHGSU-UHFFFAOYSA-N 0.000 claims 1
• MDDZBMOWENBNCP-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-4-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(C)(=O)=O)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 MDDZBMOWENBNCP-UHFFFAOYSA-N 0.000 claims 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
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• -1 glycol ethers Chemical class 0.000 description 20
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
• 239000000203 mixture Substances 0.000 description 12
• 239000000243 solution Substances 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 241000700159 Rattus Species 0.000 description 9
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000003814 drug Substances 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• FNDLQABGYJQJPH-UHFFFAOYSA-N n-(diaminomethylidene)-3-methylsulfonyl-4-propan-2-ylbenzamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC(C)C1=CC=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O FNDLQABGYJQJPH-UHFFFAOYSA-N 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
• 239000002585 base Substances 0.000 description 8
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 125000002252 acyl group Chemical group 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([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
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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• 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 4
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• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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