SK281661B6 - Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents
Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDFInfo
- 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
Links
- 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
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 208000019622 heart disease Diseases 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 39
- -1 glycol ethers Chemical class 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 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
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 210000004351 coronary vessel Anatomy 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010021143 Hypoxia Diseases 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229960001922 sodium perborate Drugs 0.000 description 4
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010011086 Coronary artery occlusion Diseases 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010047289 Ventricular extrasystoles Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229940033134 talc Drugs 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- YGYZEHXIHONBML-UHFFFAOYSA-N 4-chloro-2-methyl-5-methylsulfonylbenzoic acid Chemical compound CC1=CC(Cl)=C(S(C)(=O)=O)C=C1C(O)=O YGYZEHXIHONBML-UHFFFAOYSA-N 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 206010020880 Hypertrophy Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 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 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 206010020718 hyperplasia Diseases 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- VSMNDEVKXSFANU-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-methylsulfonyl-5-(trifluoromethyl)benzamide Chemical compound CCC1=CC(S(C)(=O)=O)=C(C(F)(F)F)C=C1C(=O)N=C(N)N VSMNDEVKXSFANU-UHFFFAOYSA-N 0.000 description 2
- JEUISQARJSGKEP-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-methylsulfonyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(S(C)(=O)=O)=C(C(F)(F)F)C=C1C(=O)N=C(N)N JEUISQARJSGKEP-UHFFFAOYSA-N 0.000 description 2
- LLTFJYFYTCTLPJ-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-propan-2-ylsulfonylbenzamide Chemical compound CC(C)S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O LLTFJYFYTCTLPJ-UHFFFAOYSA-N 0.000 description 2
- DGKMXPXRRLZVOA-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-propylsulfonylbenzamide Chemical compound CCCS(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O DGKMXPXRRLZVOA-UHFFFAOYSA-N 0.000 description 2
- MFFFQRDCIAMSRC-UHFFFAOYSA-N n-(diaminomethylidene)-4-ethylsulfonyl-2-methyl-5-methylsulfonylbenzamide Chemical compound CCS(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O MFFFQRDCIAMSRC-UHFFFAOYSA-N 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- SMKPAXGERKCGOA-UHFFFAOYSA-N 2-ethyl-4,5-bis(methylsulfinyl)benzoyl chloride Chemical compound CCC1=CC(S(C)=O)=C(S(C)=O)C=C1C(Cl)=O SMKPAXGERKCGOA-UHFFFAOYSA-N 0.000 description 1
- HDYDDSWMJUYTIY-UHFFFAOYSA-N 2-ethyl-4,5-bis(methylsulfonyl)benzoyl chloride Chemical compound CCC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(Cl)=O HDYDDSWMJUYTIY-UHFFFAOYSA-N 0.000 description 1
- UIONEPMVMSTGMS-UHFFFAOYSA-N 2-ethyl-4-ethylsulfinyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC1=CC(S(=O)CC)=C(S(C)(=O)=O)C=C1C(Cl)=O UIONEPMVMSTGMS-UHFFFAOYSA-N 0.000 description 1
- DHSDXSLBILCTDZ-UHFFFAOYSA-N 2-ethyl-4-ethylsulfonyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCC1=CC(S(=O)(=O)CC)=C(C(F)(F)F)C=C1C(Cl)=O DHSDXSLBILCTDZ-UHFFFAOYSA-N 0.000 description 1
- RDXPBFLZJZBPEF-UHFFFAOYSA-N 2-ethyl-4-ethylsulfonyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC1=CC(S(=O)(=O)CC)=C(S(C)(=O)=O)C=C1C(Cl)=O RDXPBFLZJZBPEF-UHFFFAOYSA-N 0.000 description 1
- HXWFPVYVDNRMSN-UHFFFAOYSA-N 2-ethyl-4-propan-2-ylsulfonyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCC1=CC(S(=O)(=O)C(C)C)=C(C(F)(F)F)C=C1C(Cl)=O HXWFPVYVDNRMSN-UHFFFAOYSA-N 0.000 description 1
- IEBNXQVVXMHWTK-UHFFFAOYSA-N 2-ethyl-4-propylsulfonyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCCS(=O)(=O)C1=CC(CC)=C(C(Cl)=O)C=C1C(F)(F)F IEBNXQVVXMHWTK-UHFFFAOYSA-N 0.000 description 1
- AFZFYAOHNJDVKR-UHFFFAOYSA-N 2-ethyl-5-methylsulfonyl-4-propan-2-ylsulfinylbenzoyl chloride Chemical compound CCC1=CC(S(=O)C(C)C)=C(S(C)(=O)=O)C=C1C(Cl)=O AFZFYAOHNJDVKR-UHFFFAOYSA-N 0.000 description 1
- NWZFHWYOHZFKRY-UHFFFAOYSA-N 2-ethyl-5-methylsulfonyl-4-propan-2-ylsulfonylbenzoyl chloride Chemical compound CCC1=CC(S(=O)(=O)C(C)C)=C(S(C)(=O)=O)C=C1C(Cl)=O NWZFHWYOHZFKRY-UHFFFAOYSA-N 0.000 description 1
- PMNGJTCCPGTBGA-UHFFFAOYSA-N 2-ethyl-5-methylsulfonyl-4-propylsulfinylbenzoyl chloride Chemical compound CCCS(=O)C1=CC(CC)=C(C(Cl)=O)C=C1S(C)(=O)=O PMNGJTCCPGTBGA-UHFFFAOYSA-N 0.000 description 1
- ZVUKEVDYLNCTQL-UHFFFAOYSA-N 2-ethyl-5-methylsulfonyl-4-propylsulfonylbenzoyl chloride Chemical compound CCCS(=O)(=O)C1=CC(CC)=C(C(Cl)=O)C=C1S(C)(=O)=O ZVUKEVDYLNCTQL-UHFFFAOYSA-N 0.000 description 1
- KBPZKRMZEPBEBY-UHFFFAOYSA-N 2-methyl-4,5-bis(methylsulfonyl)benzoyl chloride Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(Cl)=O KBPZKRMZEPBEBY-UHFFFAOYSA-N 0.000 description 1
- QVDRDNNSPJEVBB-UHFFFAOYSA-N 2-methyl-4-methylsulfinyl-5-methylsulfonylbenzoyl chloride Chemical compound CC1=CC(S(C)=O)=C(S(C)(=O)=O)C=C1C(Cl)=O QVDRDNNSPJEVBB-UHFFFAOYSA-N 0.000 description 1
- KJCHEWNTFHPPCH-UHFFFAOYSA-N 2-methyl-4-methylsulfonyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CC1=CC(S(C)(=O)=O)=C(C(F)(F)F)C=C1C(Cl)=O KJCHEWNTFHPPCH-UHFFFAOYSA-N 0.000 description 1
- LZFBXTDGTKFCKI-UHFFFAOYSA-N 2-methyl-4-propan-2-ylsulfonyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CC(C)S(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1C(F)(F)F LZFBXTDGTKFCKI-UHFFFAOYSA-N 0.000 description 1
- ILQHEVIJPXVGMH-UHFFFAOYSA-N 2-methyl-4-propylsulfonyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCCS(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1C(F)(F)F ILQHEVIJPXVGMH-UHFFFAOYSA-N 0.000 description 1
- CEWHISACMDWMLT-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-4-propan-2-ylsulfinylbenzoyl chloride Chemical compound CC(C)S(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O CEWHISACMDWMLT-UHFFFAOYSA-N 0.000 description 1
- XBTIWVMBDCAHHQ-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-4-propan-2-ylsulfonylbenzoyl chloride Chemical compound CC(C)S(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O XBTIWVMBDCAHHQ-UHFFFAOYSA-N 0.000 description 1
- OKZQBMULBQASQM-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-4-propylsulfinylbenzoyl chloride Chemical compound CCCS(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O OKZQBMULBQASQM-UHFFFAOYSA-N 0.000 description 1
- LOHFLUQDLKNYFP-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-4-propylsulfonylbenzoyl chloride Chemical compound CCCS(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O LOHFLUQDLKNYFP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XYSZLWJJRHBKFT-UHFFFAOYSA-N 4-(2-bromophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC=CC=2)Br)=C1C(F)(F)F XYSZLWJJRHBKFT-UHFFFAOYSA-N 0.000 description 1
- FMNNGLMVAHQKCH-UHFFFAOYSA-N 4-(2-bromophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C(=CC=CC=2)Br)=C1C(F)(F)F FMNNGLMVAHQKCH-UHFFFAOYSA-N 0.000 description 1
- ZDYYVELZPVPPEF-UHFFFAOYSA-N 4-(2-bromophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C(=CC=CC=2)Br)=C1S(C)(=O)=O ZDYYVELZPVPPEF-UHFFFAOYSA-N 0.000 description 1
- NQIPMLWRUTZHDN-UHFFFAOYSA-N 4-(2-bromophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC=CC=2)Br)=C1C(F)(F)F NQIPMLWRUTZHDN-UHFFFAOYSA-N 0.000 description 1
- LESYMIIGTKFHCF-UHFFFAOYSA-N 4-(2-bromophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC=CC=2)Br)=C1S(C)(=O)=O LESYMIIGTKFHCF-UHFFFAOYSA-N 0.000 description 1
- XONWSICSROPLFA-UHFFFAOYSA-N 4-(2-bromophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C(=CC=CC=2)Br)=C1C(F)(F)F XONWSICSROPLFA-UHFFFAOYSA-N 0.000 description 1
- QYRQNDWBWNFIJU-UHFFFAOYSA-N 4-(2-bromophenyl)sulfonyl-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)Br)=C1S(C)(=O)=O QYRQNDWBWNFIJU-UHFFFAOYSA-N 0.000 description 1
- ZFQYCQJDHRTWOF-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC=CC=2)Cl)=C1C(F)(F)F ZFQYCQJDHRTWOF-UHFFFAOYSA-N 0.000 description 1
- WSNHEYIHPZOCCB-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C(=CC=CC=2)Cl)=C1C(F)(F)F WSNHEYIHPZOCCB-UHFFFAOYSA-N 0.000 description 1
- CRTOQYSLMKNLKB-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C(=CC=CC=2)Cl)=C1S(C)(=O)=O CRTOQYSLMKNLKB-UHFFFAOYSA-N 0.000 description 1
- CQXWKBCHKYKFGY-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC=CC=2)Cl)=C1C(F)(F)F CQXWKBCHKYKFGY-UHFFFAOYSA-N 0.000 description 1
- CJZCLOPPQQCJCS-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC=CC=2)Cl)=C1S(C)(=O)=O CJZCLOPPQQCJCS-UHFFFAOYSA-N 0.000 description 1
- VANANSSALJAPQU-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C(=CC=CC=2)Cl)=C1C(F)(F)F VANANSSALJAPQU-UHFFFAOYSA-N 0.000 description 1
- VBHMDTPNHQOTRW-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfonyl-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)Cl)=C1S(C)(=O)=O VBHMDTPNHQOTRW-UHFFFAOYSA-N 0.000 description 1
- DKWRJMZVTHJGMF-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=C(Cl)C=CC=2)=C1C(F)(F)F DKWRJMZVTHJGMF-UHFFFAOYSA-N 0.000 description 1
- QVTQRXNGUSJAMB-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=C(Cl)C=CC=2)=C1S(C)(=O)=O QVTQRXNGUSJAMB-UHFFFAOYSA-N 0.000 description 1
- NLOYBLWGXCKBGO-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=C(Cl)C=CC=2)=C1C(F)(F)F NLOYBLWGXCKBGO-UHFFFAOYSA-N 0.000 description 1
- SOJGMGQDBKUTIX-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=C(Cl)C=CC=2)=C1S(C)(=O)=O SOJGMGQDBKUTIX-UHFFFAOYSA-N 0.000 description 1
- AOIKTKSFQFQGQX-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1C(F)(F)F AOIKTKSFQFQGQX-UHFFFAOYSA-N 0.000 description 1
- UHAPPMIPCULYQN-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1S(C)(=O)=O UHAPPMIPCULYQN-UHFFFAOYSA-N 0.000 description 1
- UBAOOMHQTFTXCE-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1C(F)(F)F UBAOOMHQTFTXCE-UHFFFAOYSA-N 0.000 description 1
- RGDDIAWVTJHLCQ-UHFFFAOYSA-N 4-(3-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1S(C)(=O)=O RGDDIAWVTJHLCQ-UHFFFAOYSA-N 0.000 description 1
- MDGYSFFRJRWMAN-UHFFFAOYSA-N 4-(4-bromophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(Br)=CC=2)=C1C(F)(F)F MDGYSFFRJRWMAN-UHFFFAOYSA-N 0.000 description 1
- GCYFBMZDUHRHAY-UHFFFAOYSA-N 4-(4-bromophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(Br)=CC=2)=C1S(C)(=O)=O GCYFBMZDUHRHAY-UHFFFAOYSA-N 0.000 description 1
- VNIZJMLQMKUHDD-UHFFFAOYSA-N 4-(4-bromophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=CC(Br)=CC=2)=C1C(F)(F)F VNIZJMLQMKUHDD-UHFFFAOYSA-N 0.000 description 1
- PEBJMPYLIDMXCV-UHFFFAOYSA-N 4-(4-bromophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=CC(Br)=CC=2)=C1S(C)(=O)=O PEBJMPYLIDMXCV-UHFFFAOYSA-N 0.000 description 1
- VPTOICNYQLNCBP-UHFFFAOYSA-N 4-(4-bromophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC(Br)=CC=2)=C1C(F)(F)F VPTOICNYQLNCBP-UHFFFAOYSA-N 0.000 description 1
- ZMIYWRQZLJXPFI-UHFFFAOYSA-N 4-(4-bromophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC(Br)=CC=2)=C1S(C)(=O)=O ZMIYWRQZLJXPFI-UHFFFAOYSA-N 0.000 description 1
- DGTLYVRVCPAPQL-UHFFFAOYSA-N 4-(4-bromophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=CC(Br)=CC=2)=C1C(F)(F)F DGTLYVRVCPAPQL-UHFFFAOYSA-N 0.000 description 1
- VEFSAVMLGAJRPA-UHFFFAOYSA-N 4-(4-bromophenyl)sulfonyl-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(Br)=CC=2)=C1S(C)(=O)=O VEFSAVMLGAJRPA-UHFFFAOYSA-N 0.000 description 1
- BBGKTOXUBAEVBO-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(Cl)=CC=2)=C1C(F)(F)F BBGKTOXUBAEVBO-UHFFFAOYSA-N 0.000 description 1
- AVHYCJAWBXEECZ-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(Cl)=CC=2)=C1S(C)(=O)=O AVHYCJAWBXEECZ-UHFFFAOYSA-N 0.000 description 1
- PRBUZWYLLPZYTP-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=CC(Cl)=CC=2)=C1C(F)(F)F PRBUZWYLLPZYTP-UHFFFAOYSA-N 0.000 description 1
- ZNKLNCXPMYJVTF-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=CC(Cl)=CC=2)=C1S(C)(=O)=O ZNKLNCXPMYJVTF-UHFFFAOYSA-N 0.000 description 1
- WVRPNRMSHUKSFA-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1C(F)(F)F WVRPNRMSHUKSFA-UHFFFAOYSA-N 0.000 description 1
- XTXOWRVUNDQGHU-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1S(C)(=O)=O XTXOWRVUNDQGHU-UHFFFAOYSA-N 0.000 description 1
- UKUGDFLLGWUTJJ-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1C(F)(F)F UKUGDFLLGWUTJJ-UHFFFAOYSA-N 0.000 description 1
- NQCGVQWOXIBGTJ-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-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(Cl)=CC=2)=C1S(C)(=O)=O NQCGVQWOXIBGTJ-UHFFFAOYSA-N 0.000 description 1
- BYZHTFSJKCHNLI-UHFFFAOYSA-N 4-(benzenesulfinyl)-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound C1=C(C(Cl)=O)C(CC)=CC(S(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O BYZHTFSJKCHNLI-UHFFFAOYSA-N 0.000 description 1
- LVONYDILVCESTB-UHFFFAOYSA-N 4-(benzenesulfinyl)-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound C1=C(C(Cl)=O)C(C)=CC(S(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O LVONYDILVCESTB-UHFFFAOYSA-N 0.000 description 1
- GKDDGQHRIGJDPE-UHFFFAOYSA-N 4-(benzenesulfinyl)-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O GKDDGQHRIGJDPE-UHFFFAOYSA-N 0.000 description 1
- BSUOYZCZPWILKA-UHFFFAOYSA-N 4-(benzenesulfinyl)-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O BSUOYZCZPWILKA-UHFFFAOYSA-N 0.000 description 1
- MCAOLDRYUUMGKP-UHFFFAOYSA-N 4-(benzenesulfonyl)-2-ethyl-5-(trifluoromethyl)benzoyl chloride Chemical compound C1=C(C(Cl)=O)C(CC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1C(F)(F)F MCAOLDRYUUMGKP-UHFFFAOYSA-N 0.000 description 1
- JGVBMPKEHCVWGC-UHFFFAOYSA-N 4-(benzenesulfonyl)-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound C1=C(C(Cl)=O)C(CC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O JGVBMPKEHCVWGC-UHFFFAOYSA-N 0.000 description 1
- BQCILOSYSMLCQQ-UHFFFAOYSA-N 4-(benzenesulfonyl)-2-methyl-5-(trifluoromethyl)benzoyl chloride Chemical compound C1=C(C(Cl)=O)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1C(F)(F)F BQCILOSYSMLCQQ-UHFFFAOYSA-N 0.000 description 1
- PGUZTKPFBISXDT-UHFFFAOYSA-N 4-(benzenesulfonyl)-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound C1=C(C(Cl)=O)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O PGUZTKPFBISXDT-UHFFFAOYSA-N 0.000 description 1
- RXQQYKGQHQPLOV-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1C(F)(F)F RXQQYKGQHQPLOV-UHFFFAOYSA-N 0.000 description 1
- CPDPNVZXQCSQMH-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O CPDPNVZXQCSQMH-UHFFFAOYSA-N 0.000 description 1
- VPTDAIZTXCJIFS-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1C(F)(F)F VPTDAIZTXCJIFS-UHFFFAOYSA-N 0.000 description 1
- RNBBECVBMDDUMB-UHFFFAOYSA-N 4-butan-2-ylsulfinyl-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC(C)S(=O)C1=CC(CC)=C(C(Cl)=O)C=C1S(C)(=O)=O RNBBECVBMDDUMB-UHFFFAOYSA-N 0.000 description 1
- SVWXYTXSCWZUMV-UHFFFAOYSA-N 4-butan-2-ylsulfinyl-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC(C)S(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O SVWXYTXSCWZUMV-UHFFFAOYSA-N 0.000 description 1
- RQXWSRRXRIMEMG-UHFFFAOYSA-N 4-butan-2-ylsulfinyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound CCC(C)S(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O RQXWSRRXRIMEMG-UHFFFAOYSA-N 0.000 description 1
- YBDWXQFITDAHMX-UHFFFAOYSA-N 4-butan-2-ylsulfinyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CCC(C)S(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O YBDWXQFITDAHMX-UHFFFAOYSA-N 0.000 description 1
- MSBYSMFGWUAMLK-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-2-ethyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCC(C)S(=O)(=O)C1=CC(CC)=C(C(Cl)=O)C=C1C(F)(F)F MSBYSMFGWUAMLK-UHFFFAOYSA-N 0.000 description 1
- BAALMDWAYXXRFA-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC(C)S(=O)(=O)C1=CC(CC)=C(C(Cl)=O)C=C1S(C)(=O)=O BAALMDWAYXXRFA-UHFFFAOYSA-N 0.000 description 1
- RVGNYRNDRKNAFB-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-2-methyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCC(C)S(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1C(F)(F)F RVGNYRNDRKNAFB-UHFFFAOYSA-N 0.000 description 1
- BDHZHTJSIXLNHQ-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC(C)S(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O BDHZHTJSIXLNHQ-UHFFFAOYSA-N 0.000 description 1
- ZQXPYSFTRRTILV-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound CCC(C)S(=O)(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1C(F)(F)F ZQXPYSFTRRTILV-UHFFFAOYSA-N 0.000 description 1
- VIHVTMSWZFFCBZ-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound CCC(C)S(=O)(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O VIHVTMSWZFFCBZ-UHFFFAOYSA-N 0.000 description 1
- ZCGCWZMKTAOAHX-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CCC(C)S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F ZCGCWZMKTAOAHX-UHFFFAOYSA-N 0.000 description 1
- KCOFSBLMWIYMIU-UHFFFAOYSA-N 4-butan-2-ylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CCC(C)S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O KCOFSBLMWIYMIU-UHFFFAOYSA-N 0.000 description 1
- ACJJNBOSTPMLOB-UHFFFAOYSA-N 4-butylsulfinyl-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound CCCCS(=O)C1=CC(CC)=C(C(Cl)=O)C=C1S(C)(=O)=O ACJJNBOSTPMLOB-UHFFFAOYSA-N 0.000 description 1
- DGUORFFHIDKKHP-UHFFFAOYSA-N 4-butylsulfinyl-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound CCCCS(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O DGUORFFHIDKKHP-UHFFFAOYSA-N 0.000 description 1
- SGBNGKXBWRSTOT-UHFFFAOYSA-N 4-butylsulfinyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound CCCCS(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O SGBNGKXBWRSTOT-UHFFFAOYSA-N 0.000 description 1
- OPFJUHXEKSXOHE-UHFFFAOYSA-N 4-butylsulfinyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CCCCS(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O OPFJUHXEKSXOHE-UHFFFAOYSA-N 0.000 description 1
- LNQUCMDRRPQNDH-UHFFFAOYSA-N 4-butylsulfonyl-2-ethyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCCCS(=O)(=O)C1=CC(CC)=C(C(Cl)=O)C=C1C(F)(F)F LNQUCMDRRPQNDH-UHFFFAOYSA-N 0.000 description 1
- LCHRORFQYWTIMU-UHFFFAOYSA-N 4-butylsulfonyl-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound CCCCS(=O)(=O)C1=CC(CC)=C(C(Cl)=O)C=C1S(C)(=O)=O LCHRORFQYWTIMU-UHFFFAOYSA-N 0.000 description 1
- BAMNUZNBMKZBLB-UHFFFAOYSA-N 4-butylsulfonyl-2-methyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCCCS(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1C(F)(F)F BAMNUZNBMKZBLB-UHFFFAOYSA-N 0.000 description 1
- FENOGTCTQCIGFQ-UHFFFAOYSA-N 4-butylsulfonyl-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound CCCCS(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1S(C)(=O)=O FENOGTCTQCIGFQ-UHFFFAOYSA-N 0.000 description 1
- KIKMASVRRYRTRK-UHFFFAOYSA-N 4-butylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound CCCCS(=O)(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1C(F)(F)F KIKMASVRRYRTRK-UHFFFAOYSA-N 0.000 description 1
- JXOZDMLXHWSCCM-UHFFFAOYSA-N 4-butylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound CCCCS(=O)(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O JXOZDMLXHWSCCM-UHFFFAOYSA-N 0.000 description 1
- CNXSQSRKLKHAFF-UHFFFAOYSA-N 4-butylsulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CCCCS(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F CNXSQSRKLKHAFF-UHFFFAOYSA-N 0.000 description 1
- SIGFIJJIADKXRX-UHFFFAOYSA-N 4-butylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CCCCS(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O SIGFIJJIADKXRX-UHFFFAOYSA-N 0.000 description 1
- ZGUGPLGUEUXEHN-UHFFFAOYSA-N 4-chloro-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound CC1=CC(Cl)=C(S(C)(=O)=O)C=C1C(Cl)=O ZGUGPLGUEUXEHN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FVWOOEHVCQPTOL-UHFFFAOYSA-N 4-ethylsulfonyl-2-methyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCS(=O)(=O)C1=CC(C)=C(C(Cl)=O)C=C1C(F)(F)F FVWOOEHVCQPTOL-UHFFFAOYSA-N 0.000 description 1
- OTZYPFJWGHIHEC-UHFFFAOYSA-N 4-tert-butylsulfinyl-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC1=CC(S(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(Cl)=O OTZYPFJWGHIHEC-UHFFFAOYSA-N 0.000 description 1
- IRFWLBKILKWAQP-UHFFFAOYSA-N 4-tert-butylsulfinyl-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound CC1=CC(S(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(Cl)=O IRFWLBKILKWAQP-UHFFFAOYSA-N 0.000 description 1
- MJNHJPVMRXVDMO-UHFFFAOYSA-N 4-tert-butylsulfinyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound CCC1=CC(S(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N MJNHJPVMRXVDMO-UHFFFAOYSA-N 0.000 description 1
- FPUVSAIPKICWRP-UHFFFAOYSA-N 4-tert-butylsulfinyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(S(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N FPUVSAIPKICWRP-UHFFFAOYSA-N 0.000 description 1
- QRNRCDJDDHZWDJ-UHFFFAOYSA-N 4-tert-butylsulfonyl-2-ethyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CCC1=CC(S(=O)(=O)C(C)(C)C)=C(C(F)(F)F)C=C1C(Cl)=O QRNRCDJDDHZWDJ-UHFFFAOYSA-N 0.000 description 1
- OQRLLRHSZRBINF-UHFFFAOYSA-N 4-tert-butylsulfonyl-2-ethyl-5-methylsulfonylbenzoyl chloride Chemical compound CCC1=CC(S(=O)(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(Cl)=O OQRLLRHSZRBINF-UHFFFAOYSA-N 0.000 description 1
- YXPVISBVUXWMFJ-UHFFFAOYSA-N 4-tert-butylsulfonyl-2-methyl-5-(trifluoromethyl)benzoyl chloride Chemical compound CC1=CC(S(=O)(=O)C(C)(C)C)=C(C(F)(F)F)C=C1C(Cl)=O YXPVISBVUXWMFJ-UHFFFAOYSA-N 0.000 description 1
- SECKEYQHIBKUHN-UHFFFAOYSA-N 4-tert-butylsulfonyl-2-methyl-5-methylsulfonylbenzoyl chloride Chemical compound CC1=CC(S(=O)(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(Cl)=O SECKEYQHIBKUHN-UHFFFAOYSA-N 0.000 description 1
- DLCLBPJZLJCIBI-UHFFFAOYSA-N 4-tert-butylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound CCC1=CC(S(=O)(=O)C(C)(C)C)=C(C(F)(F)F)C=C1C(=O)N=C(N)N DLCLBPJZLJCIBI-UHFFFAOYSA-N 0.000 description 1
- ZCHYXBUDYXRZSU-UHFFFAOYSA-N 4-tert-butylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound CCC1=CC(S(=O)(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N ZCHYXBUDYXRZSU-UHFFFAOYSA-N 0.000 description 1
- ZCSDWETVZOLGNU-UHFFFAOYSA-N 4-tert-butylsulfonyl-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(S(=O)(=O)C(C)(C)C)=C(C(F)(F)F)C=C1C(=O)N=C(N)N ZCSDWETVZOLGNU-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- BDZWBAXWSIXLNY-UHFFFAOYSA-N C(C)C1=C(C(=O)Cl)C=C(C(=C1)S(=O)(=O)C)C(F)(F)F Chemical compound C(C)C1=C(C(=O)Cl)C=C(C(=C1)S(=O)(=O)C)C(F)(F)F BDZWBAXWSIXLNY-UHFFFAOYSA-N 0.000 description 1
- KNSXGHIXGXHBPB-UHFFFAOYSA-N CC1=C(C(=O)Cl)C=C(C(=C1)S(=O)(=O)CC)S(=O)(=O)C Chemical compound CC1=C(C(=O)Cl)C=C(C(=C1)S(=O)(=O)CC)S(=O)(=O)C KNSXGHIXGXHBPB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 208000001778 Coronary Occlusion Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001061 Dunnett's test Methods 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020852 Hypertonia Diseases 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 241000282887 Suidae Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
- 229960002576 amiloride Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- NZLBHDRPUJLHCE-UHFFFAOYSA-N aprindine Chemical compound C1C2=CC=CC=C2CC1N(CCCN(CC)CC)C1=CC=CC=C1 NZLBHDRPUJLHCE-UHFFFAOYSA-N 0.000 description 1
- 229960004957 aprindine Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000006752 brain edema Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000003293 cardioprotective effect Effects 0.000 description 1
- IWXNYAIICFKCTM-UHFFFAOYSA-N cariporide Chemical compound CC(C)C1=CC=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O IWXNYAIICFKCTM-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000001727 in vivo Methods 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
- 230000003601 intercostal effect Effects 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
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 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
- 239000000314 lubricant 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
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- IFCDUZRSIQZRLO-UHFFFAOYSA-N methyl 4-bromo-2-methyl-5-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(C(F)(F)F)=C(Br)C=C1C IFCDUZRSIQZRLO-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical group [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 208000031225 myocardial ischemia Diseases 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
- BGOLKQXTCYCUIF-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(2-methylphenyl)sulfanyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC=CC=2)C)=C1C(F)(F)F BGOLKQXTCYCUIF-UHFFFAOYSA-N 0.000 description 1
- OFKOBOIPPPOWCK-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(2-methylphenyl)sulfanyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC=CC=2)C)=C1S(C)(=O)=O OFKOBOIPPPOWCK-UHFFFAOYSA-N 0.000 description 1
- WAVHUXYXLXUWFJ-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(2-methylphenyl)sulfonyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC=CC=2)C)=C1C(F)(F)F WAVHUXYXLXUWFJ-UHFFFAOYSA-N 0.000 description 1
- VSKMOLNRGZDOMO-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(2-methylphenyl)sulfonyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC=CC=2)C)=C1S(C)(=O)=O VSKMOLNRGZDOMO-UHFFFAOYSA-N 0.000 description 1
- DVQHSORRSSSOAU-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(3-methylphenyl)sulfanyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=C(C)C=CC=2)=C1C(F)(F)F DVQHSORRSSSOAU-UHFFFAOYSA-N 0.000 description 1
- ZNZUOWWMNRVRMO-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(3-methylphenyl)sulfanyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=C(C)C=CC=2)=C1S(C)(=O)=O ZNZUOWWMNRVRMO-UHFFFAOYSA-N 0.000 description 1
- ZOHCNAWCIPYFJP-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(3-methylphenyl)sulfonyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=C(C)C=CC=2)=C1S(C)(=O)=O ZOHCNAWCIPYFJP-UHFFFAOYSA-N 0.000 description 1
- WKZUUYHFCKRABV-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(4-methylphenyl)sulfanyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(C)=CC=2)=C1C(F)(F)F WKZUUYHFCKRABV-UHFFFAOYSA-N 0.000 description 1
- KWDBJLVSGAUINU-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(4-methylphenyl)sulfanyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(C)=CC=2)=C1S(C)(=O)=O KWDBJLVSGAUINU-UHFFFAOYSA-N 0.000 description 1
- DFYAPTJDUUPNMX-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC(C)=CC=2)=C1C(F)(F)F DFYAPTJDUUPNMX-UHFFFAOYSA-N 0.000 description 1
- AEORHAHFYBQWPK-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(4-methylphenyl)sulfonyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC(C)=CC=2)=C1S(C)(=O)=O AEORHAHFYBQWPK-UHFFFAOYSA-N 0.000 description 1
- GGFZINWUYVBDSX-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-ethylsulfinyl-5-methylsulfonylbenzamide Chemical compound CCC1=CC(S(=O)CC)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N GGFZINWUYVBDSX-UHFFFAOYSA-N 0.000 description 1
- FBYZJFVOLANJOO-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-ethylsulfonyl-5-methylsulfonylbenzamide Chemical compound CCC1=CC(S(=O)(=O)CC)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N FBYZJFVOLANJOO-UHFFFAOYSA-N 0.000 description 1
- ZZRXOUNVYPAURI-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-propan-2-ylsulfonyl-5-(trifluoromethyl)benzamide Chemical compound CCC1=CC(S(=O)(=O)C(C)C)=C(C(F)(F)F)C=C1C(=O)N=C(N)N ZZRXOUNVYPAURI-UHFFFAOYSA-N 0.000 description 1
- NFPBSAWATDHIFI-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-propylsulfonyl-5-(trifluoromethyl)benzamide Chemical compound CCCS(=O)(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1C(F)(F)F NFPBSAWATDHIFI-UHFFFAOYSA-N 0.000 description 1
- PMKJQTRDHXYZIT-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)-4-[2-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC=CC=2)C(F)(F)F)=C1C(F)(F)F PMKJQTRDHXYZIT-UHFFFAOYSA-N 0.000 description 1
- IAUNMFUEUNNPPL-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)-4-[3-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=C(C=CC=2)C(F)(F)F)=C1C(F)(F)F IAUNMFUEUNNPPL-UHFFFAOYSA-N 0.000 description 1
- CIDSBDYWIVGQJB-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)-4-[3-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C(F)(F)F CIDSBDYWIVGQJB-UHFFFAOYSA-N 0.000 description 1
- ZBOGPNGYAAISPV-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(=CC=2)C(F)(F)F)=C1C(F)(F)F ZBOGPNGYAAISPV-UHFFFAOYSA-N 0.000 description 1
- CGSVORHSABROOF-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-[2-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC=CC=2)C(F)(F)F)=C1S(C)(=O)=O CGSVORHSABROOF-UHFFFAOYSA-N 0.000 description 1
- NLAKFJKSRVDTTE-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-[2-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1S(C)(=O)=O NLAKFJKSRVDTTE-UHFFFAOYSA-N 0.000 description 1
- JXHMIJVSEQUJMD-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-[3-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1S(C)(=O)=O JXHMIJVSEQUJMD-UHFFFAOYSA-N 0.000 description 1
- PIODXQNAHOFCDO-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-[4-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C=CC(=CC=2)C(F)(F)F)=C1S(C)(=O)=O PIODXQNAHOFCDO-UHFFFAOYSA-N 0.000 description 1
- SURATTFJSRZJCQ-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-[4-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1S(C)(=O)=O SURATTFJSRZJCQ-UHFFFAOYSA-N 0.000 description 1
- RUPJVEZPFCHRIN-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-propan-2-ylsulfinylbenzamide Chemical compound CCC1=CC(S(=O)C(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N RUPJVEZPFCHRIN-UHFFFAOYSA-N 0.000 description 1
- DUFOWOOFOBFCBZ-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-propan-2-ylsulfonylbenzamide Chemical compound CCC1=CC(S(=O)(=O)C(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N DUFOWOOFOBFCBZ-UHFFFAOYSA-N 0.000 description 1
- GHPFUNFPEZFVFF-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-propylsulfinylbenzamide Chemical compound CCCS(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O GHPFUNFPEZFVFF-UHFFFAOYSA-N 0.000 description 1
- SLQUHRGHMVPDEH-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-5-methylsulfonyl-4-propylsulfonylbenzamide Chemical compound CCCS(=O)(=O)C1=CC(CC)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O SLQUHRGHMVPDEH-UHFFFAOYSA-N 0.000 description 1
- GHODGTCDTVIHKD-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(2-methylphenyl)sulfanyl-5-methylsulfonylbenzamide Chemical compound CC1=CC=CC=C1SC1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O GHODGTCDTVIHKD-UHFFFAOYSA-N 0.000 description 1
- KLSKIFLUZKHKKS-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(2-methylphenyl)sulfonyl-5-methylsulfonylbenzamide Chemical compound CC1=CC=CC=C1S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O KLSKIFLUZKHKKS-UHFFFAOYSA-N 0.000 description 1
- FQKABLRTVXECCX-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(3-methylphenyl)sulfanyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC=CC(SC=2C(=CC(=C(C)C=2)C(=O)N=C(N)N)C(F)(F)F)=C1 FQKABLRTVXECCX-UHFFFAOYSA-N 0.000 description 1
- YXKZMFDPYDQZPR-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(3-methylphenyl)sulfanyl-5-methylsulfonylbenzamide Chemical compound CC1=CC=CC(SC=2C(=CC(=C(C)C=2)C(=O)N=C(N)N)S(C)(=O)=O)=C1 YXKZMFDPYDQZPR-UHFFFAOYSA-N 0.000 description 1
- RHNPJXIMJKIMKP-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(3-methylphenyl)sulfonyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC=CC(S(=O)(=O)C=2C(=CC(=C(C)C=2)C(=O)N=C(N)N)C(F)(F)F)=C1 RHNPJXIMJKIMKP-UHFFFAOYSA-N 0.000 description 1
- WFCYVNPEVCJQJO-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(4-methylphenyl)sulfanyl-5-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1SC1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F WFCYVNPEVCJQJO-UHFFFAOYSA-N 0.000 description 1
- RBMRAKNGISWPKG-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(4-methylphenyl)sulfanyl-5-methylsulfonylbenzamide Chemical compound C1=CC(C)=CC=C1SC1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O RBMRAKNGISWPKG-UHFFFAOYSA-N 0.000 description 1
- FYQCXACRBCASKV-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F FYQCXACRBCASKV-UHFFFAOYSA-N 0.000 description 1
- UXNFLIFWRHSGKR-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(4-methylphenyl)sulfonyl-5-methylsulfonylbenzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O UXNFLIFWRHSGKR-UHFFFAOYSA-N 0.000 description 1
- GBGFGZQDQKPPLQ-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-methylsulfinyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(S(C)=O)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N GBGFGZQDQKPPLQ-UHFFFAOYSA-N 0.000 description 1
- HXDXMJMDMDLWGO-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-methylsulfonyl-5-nitrobenzamide Chemical compound CC1=CC(S(C)(=O)=O)=C([N+]([O-])=O)C=C1C(=O)N=C(N)N HXDXMJMDMDLWGO-UHFFFAOYSA-N 0.000 description 1
- OFDNDURIILCNPJ-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-propan-2-ylsulfonyl-5-(trifluoromethyl)benzamide Chemical compound CC(C)S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F OFDNDURIILCNPJ-UHFFFAOYSA-N 0.000 description 1
- PRYJTVPLVGDHDJ-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-propylsulfonyl-5-(trifluoromethyl)benzamide Chemical compound CCCS(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F PRYJTVPLVGDHDJ-UHFFFAOYSA-N 0.000 description 1
- GFQZDBKIZCGXCF-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)-4-[2-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C(=CC=CC=2)C(F)(F)F)=C1C(F)(F)F GFQZDBKIZCGXCF-UHFFFAOYSA-N 0.000 description 1
- ZSBJVEGLTCQNCK-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)-4-[3-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=C(C=CC=2)C(F)(F)F)=C1C(F)(F)F ZSBJVEGLTCQNCK-UHFFFAOYSA-N 0.000 description 1
- CFDZGCQPSOBMTI-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=CC(=CC=2)C(F)(F)F)=C1C(F)(F)F CFDZGCQPSOBMTI-UHFFFAOYSA-N 0.000 description 1
- ZQLOUGOUCHMKHV-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1C(F)(F)F ZQLOUGOUCHMKHV-UHFFFAOYSA-N 0.000 description 1
- MYTFLWAIHRGAPE-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[2-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C(=CC=CC=2)C(F)(F)F)=C1S(C)(=O)=O MYTFLWAIHRGAPE-UHFFFAOYSA-N 0.000 description 1
- CDOUFVAURAXMMH-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[2-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1S(C)(=O)=O CDOUFVAURAXMMH-UHFFFAOYSA-N 0.000 description 1
- NFZMWSDZYXFMLH-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[3-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=C(C=CC=2)C(F)(F)F)=C1S(C)(=O)=O NFZMWSDZYXFMLH-UHFFFAOYSA-N 0.000 description 1
- WVZNBVWOMAPNAW-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[3-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1S(C)(=O)=O WVZNBVWOMAPNAW-UHFFFAOYSA-N 0.000 description 1
- VAHSYQRAUVRLJY-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[4-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=CC(=CC=2)C(F)(F)F)=C1S(C)(=O)=O VAHSYQRAUVRLJY-UHFFFAOYSA-N 0.000 description 1
- ZFVIMWBMDDQEEY-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-propan-2-ylsulfinylbenzamide Chemical compound CC(C)S(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O ZFVIMWBMDDQEEY-UHFFFAOYSA-N 0.000 description 1
- SPVMMRALAJYBSX-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-propylsulfinylbenzamide Chemical compound CCCS(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O SPVMMRALAJYBSX-UHFFFAOYSA-N 0.000 description 1
- GTOYOXDESAEYOG-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-nitro-4-propan-2-ylsulfonylbenzamide Chemical compound CC(C)S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1[N+]([O-])=O GTOYOXDESAEYOG-UHFFFAOYSA-N 0.000 description 1
- CFLLWKVNYSULCQ-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfanyl-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC(C)=CC=2)C)=C1C(F)(F)F CFLLWKVNYSULCQ-UHFFFAOYSA-N 0.000 description 1
- XEFOFHWFNFZJGG-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfanyl-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC(C)=CC=2)C)=C1S(C)(=O)=O XEFOFHWFNFZJGG-UHFFFAOYSA-N 0.000 description 1
- SYHWZGMHTGKSEP-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfanyl-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1SC1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F SYHWZGMHTGKSEP-UHFFFAOYSA-N 0.000 description 1
- UUBNPEYIPPEJQQ-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC(C)=CC=2)C)=C1C(F)(F)F UUBNPEYIPPEJQQ-UHFFFAOYSA-N 0.000 description 1
- FAFYOAANLIJPSH-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC(C)=CC=2)C)=C1S(C)(=O)=O FAFYOAANLIJPSH-UHFFFAOYSA-N 0.000 description 1
- IJDATBYDQVJVRG-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F IJDATBYDQVJVRG-UHFFFAOYSA-N 0.000 description 1
- PTJVDVWCWUYBKI-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O PTJVDVWCWUYBKI-UHFFFAOYSA-N 0.000 description 1
- GELRCTZDSRLROA-UHFFFAOYSA-N n-(diaminomethylidene)-4-ethylsulfinyl-2-methyl-5-methylsulfonylbenzamide Chemical compound CCS(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O GELRCTZDSRLROA-UHFFFAOYSA-N 0.000 description 1
- REACOYHFNDUUHP-UHFFFAOYSA-N n-(diaminomethylidene)-4-ethylsulfonyl-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CCS(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F REACOYHFNDUUHP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 208000017497 prostate disease Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 230000010410 reperfusion 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
- 238000000926 separation method Methods 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 229960004793 sucrose Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000012360 testing method Methods 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 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
- 229960002622 triacetin Drugs 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
- 238000009423 ventilation Methods 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
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07C317/26—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
- C07C317/34—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 having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—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 having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (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)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Pulmonology (AREA)
- Reproductive Health (AREA)
- Gastroenterology & Hepatology (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)
- Measuring Leads Or Probes (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19529612A DE19529612A1 (de) | 1995-08-11 | 1995-08-11 | Sulfonyl- oder Sulfinyl-benzoylguanidin-Derivate |
Publications (2)
Publication Number | Publication Date |
---|---|
SK103396A3 SK103396A3 (en) | 1997-03-05 |
SK281661B6 true SK281661B6 (sk) | 2001-06-11 |
Family
ID=7769293
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1033-96A SK281661B6 (sk) | 1995-08-11 | 1996-08-07 | Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje |
Country Status (25)
Country | Link |
---|---|
US (1) | US5744641A (ru) |
EP (1) | EP0758644B1 (ru) |
JP (1) | JP3901766B2 (ru) |
KR (1) | KR100447111B1 (ru) |
CN (1) | CN1071743C (ru) |
AR (1) | AR004677A1 (ru) |
AT (1) | ATE252075T1 (ru) |
AU (1) | AU709800B2 (ru) |
BR (1) | BR9603377B1 (ru) |
CA (1) | CA2183050C (ru) |
CZ (1) | CZ292974B6 (ru) |
DE (2) | DE19529612A1 (ru) |
DK (1) | DK0758644T3 (ru) |
ES (1) | ES2206534T3 (ru) |
HU (1) | HU226134B1 (ru) |
MX (1) | MX9603300A (ru) |
NO (1) | NO306858B1 (ru) |
PL (1) | PL184320B1 (ru) |
PT (1) | PT758644E (ru) |
RU (1) | RU2159232C2 (ru) |
SI (1) | SI0758644T1 (ru) |
SK (1) | SK281661B6 (ru) |
TW (1) | TW432039B (ru) |
UA (1) | UA45965C2 (ru) |
ZA (1) | ZA966773B (ru) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4328352A1 (de) | 1993-08-24 | 1995-03-02 | Hoechst Ag | Substituierte N,N'-Di-benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
DE19833118C2 (de) * | 1998-07-23 | 2000-07-27 | Merck Patent Gmbh | Verfahren zur Herstellung von orthoalkylierten Benzoesäurederivaten |
DE19903275A1 (de) * | 1999-01-28 | 2000-08-03 | Merck Patent Gmbh | Lyophilisate mit verbesserter Rekonstituierbarkeit |
DE19951418A1 (de) | 1999-10-26 | 2001-05-03 | Merck Patent Gmbh | Verfahren zur Herstellung von N-(4,5-Bismethansulfonyl-2-methyl-benzoyl) -guanidin, Hydrochlorid |
DE10001879A1 (de) * | 2000-01-19 | 2001-07-19 | Aventis Pharma Gmbh | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
DE10023405A1 (de) | 2000-05-12 | 2001-11-15 | Merck Patent Gmbh | Verfahren zur Herstellung von Sulfonyl-benzoylguanidinum-Salzen |
KR100643561B1 (ko) * | 2000-12-08 | 2006-11-10 | 엘지.필립스 엘시디 주식회사 | 액정표시장치용 어레이기판과 어레이기판의 제조방법 |
DE10305070A1 (de) * | 2003-02-07 | 2004-08-26 | Merck Patent Gmbh | Verwendung von N-(4,5-Methansulfonyl-2-methyl-benzoyl)-guanidin |
US7629493B2 (en) * | 2003-05-06 | 2009-12-08 | Merck Patent Gmbh | Process for the crystallisation of guandinium salts |
DE102004045825A1 (de) * | 2004-09-22 | 2006-03-23 | Merck Patent Gmbh | Lyophilisat enthaltend N-Diaminomethylen-2-methyl-4,5-di-(methylsulfonyl)-benzamid |
AU2009243749B2 (en) | 2008-05-09 | 2013-11-21 | Merck Patent Gmbh | Pharmaceutical composition comprising rimeporide for treating diseases associated with insulin resistance and beta-cell dysfunction |
US8822449B2 (en) | 2008-09-02 | 2014-09-02 | Sanofi | Substituted aminoindanes and analogs thereof, and the pharmaceutical use thereof |
FR2948028B1 (fr) | 2009-07-17 | 2011-12-02 | Merck Sante Sas | Association d'un inhibiteur de l'echangeur sodium-proton et d'un derive amine de dihydro-1,3,5-triazine |
MX2018009558A (es) * | 2016-02-08 | 2018-09-06 | Merck Patent Gmbh | Modificaciones cristalinas de clorhidrato de n-(4,5-bismetansulfon il-2-metilbenzoil)guanidina y sales de n-(4,5-bismetansulfonil-2-m etilbenzoil)guanidina. |
EP4230196A1 (en) | 2022-02-21 | 2023-08-23 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of dystrophinopathies |
Family Cites Families (4)
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 |
EP0589336B1 (de) * | 1992-09-22 | 1997-01-08 | Hoechst Aktiengesellschaft | Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika |
EP0604852A1 (de) * | 1992-12-28 | 1994-07-06 | Hoechst Aktiengesellschaft | 2,4-Substituierte 5-(N-substituierte-Sulfamoyl)-Benzoylguanidine, als Antiarrythmika, Inhibitoren der Proliferationen von Zellen, und Inhibitoren des Natrium-Protonen-Antiporters |
DE4430916A1 (de) * | 1994-08-31 | 1996-03-07 | Merck Patent Gmbh | Alkyl-benzoylguanidin-Derivate |
-
1995
- 1995-08-11 DE DE19529612A patent/DE19529612A1/de not_active Withdrawn
-
1996
- 1996-07-16 TW TW085108613A patent/TW432039B/zh not_active IP Right Cessation
- 1996-08-02 ES ES96112498T patent/ES2206534T3/es not_active Expired - Lifetime
- 1996-08-02 PT PT96112498T patent/PT758644E/pt unknown
- 1996-08-02 DK DK96112498T patent/DK0758644T3/da active
- 1996-08-02 DE DE59610773T patent/DE59610773D1/de not_active Expired - Lifetime
- 1996-08-02 AT AT96112498T patent/ATE252075T1/de active
- 1996-08-02 SI SI9630659T patent/SI0758644T1/xx unknown
- 1996-08-02 EP EP96112498A patent/EP0758644B1/de not_active Expired - Lifetime
- 1996-08-05 CZ CZ19962312A patent/CZ292974B6/cs not_active IP Right Cessation
- 1996-08-05 AU AU61917/96A patent/AU709800B2/en not_active Expired
- 1996-08-07 SK SK1033-96A patent/SK281661B6/sk not_active IP Right Cessation
- 1996-08-08 UA UA96083195A patent/UA45965C2/uk unknown
- 1996-08-08 ZA ZA9606773A patent/ZA966773B/xx unknown
- 1996-08-08 JP JP22459596A patent/JP3901766B2/ja not_active Expired - Lifetime
- 1996-08-09 BR BRPI9603377-0A patent/BR9603377B1/pt not_active IP Right Cessation
- 1996-08-09 RU RU96115459/04A patent/RU2159232C2/ru active
- 1996-08-09 AR ARP960103933A patent/AR004677A1/es active IP Right Grant
- 1996-08-09 CA CA002183050A patent/CA2183050C/en not_active Expired - Lifetime
- 1996-08-09 NO NO963340A patent/NO306858B1/no not_active IP Right Cessation
- 1996-08-09 KR KR1019960033207A patent/KR100447111B1/ko not_active IP Right Cessation
- 1996-08-09 CN CN96109414A patent/CN1071743C/zh not_active Expired - Lifetime
- 1996-08-09 MX MX9603300A patent/MX9603300A/es unknown
- 1996-08-09 US US08/699,053 patent/US5744641A/en not_active Expired - Lifetime
- 1996-08-09 PL PL96315611A patent/PL184320B1/pl unknown
- 1996-08-09 HU HU9602196A patent/HU226134B1/hu not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
PT667341E (pt) | 4-amino-1-peperidilbenzoilguanidinas como inibidores do antiporte na+/h+ | |
SK281661B6 (sk) | Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
SK281446B6 (sk) | Heterocyklylbenzoylguanidín, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
SK282202B6 (sk) | Derivát kyseliny benzoovej substituovanej v orto polohe, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
RU2142940C1 (ru) | Производные алкилбензоилгуанидинов, способ их получения и фармацевтическая композиция на их основе | |
US5807896A (en) | Arylbenzoylguanidines | |
SK282052B6 (sk) | Derivát benzoylguanidínu obsahujúceho fluór, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
SK281198B6 (sk) | Derivát 4-aminobenzoylguanidínu, spôsob jeho prípravy a farmaceutický prostriedok, ktorý ho obsahuje | |
US5700839A (en) | Alkyl-5-methylsulfonylbenzoylguanidine derivatives | |
US5731351A (en) | Alkenyl-benzoylguanidine derivatives | |
AU706843B2 (en) | 4-mercaptobenzoylguanidine derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK4A | Patent expired |
Expiry date: 20160807 |