SK81598A3 - Cyclic sulfone derivative, preparation thereof and pharmaceutical composition containing the same - Google Patents
Cyclic sulfone derivative, preparation thereof and pharmaceutical composition containing the same Download PDFInfo
- Publication number
- SK81598A3 SK81598A3 SK815-98A SK81598A SK81598A3 SK 81598 A3 SK81598 A3 SK 81598A3 SK 81598 A SK81598 A SK 81598A SK 81598 A3 SK81598 A3 SK 81598A3
- Authority
- SK
- Slovakia
- Prior art keywords
- dioxide
- carboxamide
- diaminomethylene
- benzothiophene
- methyl
- Prior art date
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- -1 Cyclic sulfone Chemical class 0.000 title claims description 209
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 238000011282 treatment Methods 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 7
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000006793 arrhythmia Effects 0.000 claims description 5
- 206010003119 arrhythmia Diseases 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- BERFJTJYXHNHBH-UHFFFAOYSA-N n-(diaminomethylidene)-3-hydroxy-3,5-dimethyl-1,1-dioxo-2h-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)CC2(C)O BERFJTJYXHNHBH-UHFFFAOYSA-N 0.000 claims description 2
- NSYLKEYRQBPJBL-UHFFFAOYSA-N n-(diaminomethylidene)-3-methoxy-3,5-dimethyl-1,1-dioxo-2h-1-benzothiophene-6-carboxamide Chemical compound NC(N)=NC(=O)C1=C(C)C=C2C(OC)(C)CS(=O)(=O)C2=C1 NSYLKEYRQBPJBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 230000001413 cellular effect Effects 0.000 abstract description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 91
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- VMGLLMDIYIPVHX-UHFFFAOYSA-N 1-benzothiophene-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=CSC2=C1 VMGLLMDIYIPVHX-UHFFFAOYSA-N 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 206010021143 Hypoxia Diseases 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 229960004198 guanidine Drugs 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 230000007717 exclusion Effects 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- JSOOPQZKEUZXLH-UHFFFAOYSA-N 2H-1,4-benzothiazine-7-carboxylic acid Chemical compound S1C2=C(N=CC1)C=CC(=C2)C(=O)O JSOOPQZKEUZXLH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229960000789 guanidine hydrochloride Drugs 0.000 description 4
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 4
- 238000007327 hydrogenolysis reaction Methods 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
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-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 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010061216 Infarction Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
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- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- QZRXGEXAXNVNDY-UHFFFAOYSA-N 2H-1,2-benzothiazine-7-carboxylic acid Chemical compound S1NC=CC2=C1C=C(C=C2)C(=O)O QZRXGEXAXNVNDY-UHFFFAOYSA-N 0.000 description 2
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- ZKPGRIGFYCELDS-UHFFFAOYSA-N n-(diaminomethylidene)-5-fluoro-2,2-dimethyl-1,1-dioxo-3h-1-benzothiophene-6-carboxamide Chemical compound FC1=C(C(=O)N=C(N)N)C=C2S(=O)(=O)C(C)(C)CC2=C1 ZKPGRIGFYCELDS-UHFFFAOYSA-N 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 210000003734 kidney Anatomy 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- MSMKDNYOZOAJAG-UHFFFAOYSA-N methyl 1',1'-dioxo-5'-(trifluoromethyl)spiro[1,3-dioxolane-2,3'-2h-1-benzothiophene]-6'-carboxylate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC(S(C2)(=O)=O)=C1C12OCCO1 MSMKDNYOZOAJAG-UHFFFAOYSA-N 0.000 description 1
- ZIOSIHAQWWWCTO-UHFFFAOYSA-N methyl 1,1-dioxo-3-phenyl-1-benzothiophene-6-carboxylate Chemical compound C=1S(=O)(=O)C2=CC(C(=O)OC)=CC=C2C=1C1=CC=CC=C1 ZIOSIHAQWWWCTO-UHFFFAOYSA-N 0.000 description 1
- XCDQIUIOQIOHFF-UHFFFAOYSA-N methyl 1-benzothiophene-5-carboxylate Chemical compound COC(=O)C1=CC=C2SC=CC2=C1 XCDQIUIOQIOHFF-UHFFFAOYSA-N 0.000 description 1
- LUAQLMFNQYOVPQ-UHFFFAOYSA-N methyl 1-benzothiophene-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CSC2=C1 LUAQLMFNQYOVPQ-UHFFFAOYSA-N 0.000 description 1
- MHZSHSJCALJOSG-UHFFFAOYSA-N methyl 2,2-dimethyl-1,1-dioxo-3h-1,3-benzothiazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2S(=O)(=O)C(C)(C)NC2=C1 MHZSHSJCALJOSG-UHFFFAOYSA-N 0.000 description 1
- GXXBTIDNLAFATC-UHFFFAOYSA-N methyl 2,3-dimethyl-1,1-dioxo-2h-1,3-benzothiazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2S(=O)(=O)C(C)N(C)C2=C1 GXXBTIDNLAFATC-UHFFFAOYSA-N 0.000 description 1
- OOMFGAFEAHPOTB-UHFFFAOYSA-N methyl 2,6-dimethyl-1,1-dioxo-4h-thiochromene-7-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1CC=C(C)S2(=O)=O OOMFGAFEAHPOTB-UHFFFAOYSA-N 0.000 description 1
- RNZYRGDWQOMLAO-UHFFFAOYSA-N methyl 2,6-dimethyl-3,3-dioxo-1,3$l^{6}-benzoxathiole-5-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1OC(C)S2(=O)=O RNZYRGDWQOMLAO-UHFFFAOYSA-N 0.000 description 1
- BFVCJWPYJBHKMT-UHFFFAOYSA-N methyl 2,7-dimethyl-4,4-dioxo-2,3-dihydro-1,4$l^{6}-benzoxathiine-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1OC(C)CS2(=O)=O BFVCJWPYJBHKMT-UHFFFAOYSA-N 0.000 description 1
- JADJHXXHLNHYJX-UHFFFAOYSA-N methyl 2-methyl-1,1-dioxo-2,3-dihydro-1,3-benzothiazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2S(=O)(=O)C(C)NC2=C1 JADJHXXHLNHYJX-UHFFFAOYSA-N 0.000 description 1
- YNTKEFFVEPDYNP-UHFFFAOYSA-N methyl 2-methyl-1,1-dioxo-4h-3,1$l^{6}-benzoxathiine-7-carboxylate Chemical compound C1OC(C)S(=O)(=O)C2=CC(C(=O)OC)=CC=C21 YNTKEFFVEPDYNP-UHFFFAOYSA-N 0.000 description 1
- ZEQOASNYYUBBED-UHFFFAOYSA-N methyl 3-cyano-5-methyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1C(C#N)CS2(=O)=O ZEQOASNYYUBBED-UHFFFAOYSA-N 0.000 description 1
- RSZLLVSHOHCFOG-UHFFFAOYSA-N methyl 3-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxylate Chemical compound COC(=O)C1=CC=C2C(O)CS(=O)(=O)C2=C1 RSZLLVSHOHCFOG-UHFFFAOYSA-N 0.000 description 1
- AEADBCDBWQJZFP-UHFFFAOYSA-N methyl 3-hydroxy-5-methyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1C(O)CS2(=O)=O AEADBCDBWQJZFP-UHFFFAOYSA-N 0.000 description 1
- XKEQQVDMMFZTFX-UHFFFAOYSA-N methyl 3-methyl-1,1-dioxo-2,4-dihydro-1$l^{6},3-benzothiazine-7-carboxylate Chemical compound C1N(C)CS(=O)(=O)C2=CC(C(=O)OC)=CC=C21 XKEQQVDMMFZTFX-UHFFFAOYSA-N 0.000 description 1
- FAOYNQVHPFYPFW-UHFFFAOYSA-N methyl 4,4-dioxo-2,3-dihydro-1,4$l^{6}-benzoxathiine-6-carboxylate Chemical compound O1CCS(=O)(=O)C2=CC(C(=O)OC)=CC=C21 FAOYNQVHPFYPFW-UHFFFAOYSA-N 0.000 description 1
- GFZOWGXSQHCLTP-UHFFFAOYSA-N methyl 5-ethyl-2,3-dimethyl-1,1-dioxo-2,4-dihydro-1,3-benzothiazole-5-carboxylate Chemical compound C1=CC(CC)(C(=O)OC)CC2=C1S(=O)(=O)C(C)N2C GFZOWGXSQHCLTP-UHFFFAOYSA-N 0.000 description 1
- YJHCAAQIGYTHRX-UHFFFAOYSA-N methyl 5-methyl-1,1-dioxo-1-benzothiophene-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1C=CS2(=O)=O YJHCAAQIGYTHRX-UHFFFAOYSA-N 0.000 description 1
- CDPTYGWKNCJKGP-UHFFFAOYSA-N methyl 5-methyl-1,1-dioxo-2,3-dihydro-1,3-benzothiazole-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1NCS2(=O)=O CDPTYGWKNCJKGP-UHFFFAOYSA-N 0.000 description 1
- SFMDPXNOYCCZTC-UHFFFAOYSA-N methyl 5-methyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1CCS2(=O)=O SFMDPXNOYCCZTC-UHFFFAOYSA-N 0.000 description 1
- ONHFGHSDZWBRQG-UHFFFAOYSA-N methyl 6-ethyl-2,2-dimethyl-3,3-dioxo-1,3$l^{6}-benzoxathiole-5-carboxylate Chemical compound C1=C(C(=O)OC)C(CC)=CC2=C1S(=O)(=O)C(C)(C)O2 ONHFGHSDZWBRQG-UHFFFAOYSA-N 0.000 description 1
- HSHLDMMYXWQXBK-UHFFFAOYSA-N methyl 6-ethyl-2-methyl-1,1-dioxo-2h-thiochromene-7-carboxylate Chemical compound C1=CC(C)S(=O)(=O)C2=C1C=C(CC)C(C(=O)OC)=C2 HSHLDMMYXWQXBK-UHFFFAOYSA-N 0.000 description 1
- WZNIXKOAYKDMMN-UHFFFAOYSA-N methyl 6-ethyl-2-methyl-3,3-dioxo-1,3$l^{6}-benzoxathiole-5-carboxylate Chemical compound C1=C(C(=O)OC)C(CC)=CC2=C1S(=O)(=O)C(C)O2 WZNIXKOAYKDMMN-UHFFFAOYSA-N 0.000 description 1
- LMUYMLQBBXPRNG-UHFFFAOYSA-N methyl 6-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},3-benzothiazine-7-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1CNCS2(=O)=O LMUYMLQBBXPRNG-UHFFFAOYSA-N 0.000 description 1
- WCLDGHNQQXADTG-UHFFFAOYSA-N methyl 6-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},4-benzothiazine-7-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1NCCS2(=O)=O WCLDGHNQQXADTG-UHFFFAOYSA-N 0.000 description 1
- AVDOBVZHXOWEDF-UHFFFAOYSA-N methyl 6-methyl-1,1-dioxo-3,4-dihydro-2h-thiochromene-7-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1CCCS2(=O)=O AVDOBVZHXOWEDF-UHFFFAOYSA-N 0.000 description 1
- SXHRIMILUFAMJD-UHFFFAOYSA-N methyl 6-methyl-1,1-dioxo-4h-3,1$l^{6}-benzoxathiine-7-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1COCS2(=O)=O SXHRIMILUFAMJD-UHFFFAOYSA-N 0.000 description 1
- YSKGHGUSKWXIMZ-UHFFFAOYSA-N methyl 6-methyl-3,3-dioxo-1,3$l^{6}-benzoxathiole-5-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1OCS2(=O)=O YSKGHGUSKWXIMZ-UHFFFAOYSA-N 0.000 description 1
- ZKWXYMPIYKKANP-UHFFFAOYSA-N methyl 7-ethyl-2,4,4-trioxo-1,4$l^{6}-benzoxathiine-6-carboxylate Chemical compound O1C(=O)CS(=O)(=O)C2=C1C=C(CC)C(C(=O)OC)=C2 ZKWXYMPIYKKANP-UHFFFAOYSA-N 0.000 description 1
- RINZZITYDZMEPD-UHFFFAOYSA-N methyl 7-methyl-2,4,4-trioxo-1,4$l^{6}-benzoxathiine-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1OC(=O)CS2(=O)=O RINZZITYDZMEPD-UHFFFAOYSA-N 0.000 description 1
- RYVSRRQCSFTAAD-UHFFFAOYSA-N methyl 7-methyl-4,4-dioxo-2,3-dihydro-1,4$l^{6}-benzoxathiine-6-carboxylate Chemical compound C1=C(C)C(C(=O)OC)=CC2=C1OCCS2(=O)=O RYVSRRQCSFTAAD-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- PCRQQHNTAPAHMK-UHFFFAOYSA-N n-(diaminomethylidene)-1,1,3-trioxo-5-(trifluoromethyl)-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(F)(F)F)C(C(=O)N=C(N)N)=CC2=C1C(=O)CS2(=O)=O PCRQQHNTAPAHMK-UHFFFAOYSA-N 0.000 description 1
- MFUCHHQIDQYIMK-UHFFFAOYSA-N n-(diaminomethylidene)-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxamide Chemical compound NC(N)=NC(=O)C1=CC=C2CCS(=O)(=O)C2=C1 MFUCHHQIDQYIMK-UHFFFAOYSA-N 0.000 description 1
- HQABYSSNPFYRLP-UHFFFAOYSA-N n-(diaminomethylidene)-2,2,5-trimethyl-1,1,3-trioxo-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)C(C)(C)C2=O HQABYSSNPFYRLP-UHFFFAOYSA-N 0.000 description 1
- HMJWJJXUXSNPQE-UHFFFAOYSA-N n-(diaminomethylidene)-2,2,6-trimethyl-1,1-dioxo-3h-1$l^{6},4-benzodithiine-7-carboxamide Chemical compound S1CC(C)(C)S(=O)(=O)C2=C1C=C(C)C(C(=O)N=C(N)N)=C2 HMJWJJXUXSNPQE-UHFFFAOYSA-N 0.000 description 1
- FYWBMYAZYCDHEG-UHFFFAOYSA-N n-(diaminomethylidene)-2,2,6-trimethyl-1,1-dioxo-4h-3,1$l^{6}-benzoxathiine-7-carboxamide Chemical compound C1OC(C)(C)S(=O)(=O)C2=C1C=C(C)C(C(=O)N=C(N)N)=C2 FYWBMYAZYCDHEG-UHFFFAOYSA-N 0.000 description 1
- SDHSHHDPLBJPLZ-UHFFFAOYSA-N n-(diaminomethylidene)-2,2,6-trimethyl-1,1-dioxothiochromene-7-carboxamide Chemical compound C1=CC(C)(C)S(=O)(=O)C2=C1C=C(C)C(C(=O)N=C(N)N)=C2 SDHSHHDPLBJPLZ-UHFFFAOYSA-N 0.000 description 1
- WXBMIFWRKYXZEO-UHFFFAOYSA-N n-(diaminomethylidene)-2,2,7-trimethyl-4,4-dioxo-3h-1,4$l^{6}-benzoxathiine-6-carboxamide Chemical compound O1C(C)(C)CS(=O)(=O)C2=C1C=C(C)C(C(=O)N=C(N)N)=C2 WXBMIFWRKYXZEO-UHFFFAOYSA-N 0.000 description 1
- FVNMQIVZFBZLIJ-UHFFFAOYSA-N n-(diaminomethylidene)-2,2-dimethyl-1,1-dioxothiochromene-7-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=C2S(=O)(=O)C(C)(C)C=CC2=C1 FVNMQIVZFBZLIJ-UHFFFAOYSA-N 0.000 description 1
- JNRJHWAUKKFXNC-UHFFFAOYSA-N n-(diaminomethylidene)-2,2-dimethyl-3,3-dioxo-1,3$l^{6}-benzoxathiole-5-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=C2S(=O)(=O)C(C)(C)OC2=C1 JNRJHWAUKKFXNC-UHFFFAOYSA-N 0.000 description 1
- KMPGVBCTBQTBNS-UHFFFAOYSA-N n-(diaminomethylidene)-2,4,4-trioxo-1,4$l^{6}-benzoxathiine-6-carboxamide Chemical compound O1C(=O)CS(=O)(=O)C2=CC(C(=O)N=C(N)N)=CC=C21 KMPGVBCTBQTBNS-UHFFFAOYSA-N 0.000 description 1
- IAKFSSYFTPRVDH-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-1,1-dioxo-2,3-dihydro-1$l^{6},4-benzodithiine-7-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=C2S(=O)(=O)C(C)CSC2=C1 IAKFSSYFTPRVDH-UHFFFAOYSA-N 0.000 description 1
- CPDYMDNXZSDUHP-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=C2S(=O)(=O)C(C)CC2=C1 CPDYMDNXZSDUHP-UHFFFAOYSA-N 0.000 description 1
- AQQUQTGRGYFODU-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-3,3-dioxo-1,3$l^{6}-benzoxathiole-5-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=C2S(=O)(=O)C(C)OC2=C1 AQQUQTGRGYFODU-UHFFFAOYSA-N 0.000 description 1
- LOEVVCFPYCOPDF-UHFFFAOYSA-N n-(diaminomethylidene)-3,3,5-trimethyl-1,1-dioxo-2h-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)CC2(C)C LOEVVCFPYCOPDF-UHFFFAOYSA-N 0.000 description 1
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- MSFYKAIYDUFTNA-UHFFFAOYSA-N n-(diaminomethylidene)-3-hydroxy-5-methyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)CC2O MSFYKAIYDUFTNA-UHFFFAOYSA-N 0.000 description 1
- KETXFEVMJKNQDV-UHFFFAOYSA-N n-(diaminomethylidene)-3-hydroxyimino-2,2,5-trimethyl-1,1-dioxo-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)C(C)(C)C2=NO KETXFEVMJKNQDV-UHFFFAOYSA-N 0.000 description 1
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- LHRQVMCVQUJLDN-UHFFFAOYSA-N n-(diaminomethylidene)-3-methoxyimino-1,1-dioxo-1-benzothiophene-6-carboxamide Chemical compound NC(N)=NC(=O)C1=CC=C2C(=NOC)CS(=O)(=O)C2=C1 LHRQVMCVQUJLDN-UHFFFAOYSA-N 0.000 description 1
- GULFTNWMBQBESD-UHFFFAOYSA-N n-(diaminomethylidene)-3-methoxyimino-5-methyl-1,1-dioxo-1-benzothiophene-6-carboxamide Chemical compound NC(N)=NC(=O)C1=C(C)C=C2C(=NOC)CS(=O)(=O)C2=C1 GULFTNWMBQBESD-UHFFFAOYSA-N 0.000 description 1
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- UUGQCUUMEFOYSY-UHFFFAOYSA-N n-(diaminomethylidene)-4,6-dimethyl-1,1-dioxo-3,4-dihydro-2h-thiochromene-7-carboxamide Chemical compound NC(N)=NC(=O)C1=C(C)C=C2C(C)CCS(=O)(=O)C2=C1 UUGQCUUMEFOYSY-UHFFFAOYSA-N 0.000 description 1
- CVFFBMWKRDCXEO-UHFFFAOYSA-N n-(diaminomethylidene)-5'-ethyl-1',1'-dioxospiro[1,3-dioxolane-2,3'-2h-1-benzothiophene]-6'-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC2=C1S(=O)(=O)CC21OCCO1 CVFFBMWKRDCXEO-UHFFFAOYSA-N 0.000 description 1
- KCZRYMAJJHFPSK-UHFFFAOYSA-N n-(diaminomethylidene)-5'-fluoro-1',1'-dioxospiro[1,3-dioxolane-2,3'-2h-1-benzothiophene]-6'-carboxamide Chemical compound C1=C(F)C(C(=O)N=C(N)N)=CC(S(C2)(=O)=O)=C1C12OCCO1 KCZRYMAJJHFPSK-UHFFFAOYSA-N 0.000 description 1
- RGMZCEYXLNCXKJ-UHFFFAOYSA-N n-(diaminomethylidene)-5'-methyl-1',1'-dioxospiro[1,3-dioxolane-2,3'-2h-1-benzothiophene]-6'-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)CC21OCCO1 RGMZCEYXLNCXKJ-UHFFFAOYSA-N 0.000 description 1
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- KWQAHKWQKRXLGQ-UHFFFAOYSA-N n-(diaminomethylidene)-5-methyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)CC2 KWQAHKWQKRXLGQ-UHFFFAOYSA-N 0.000 description 1
- SEYBCQCNILYQAU-UHFFFAOYSA-N n-(diaminomethylidene)-5-methyl-1,1-dioxo-3-propan-2-yl-2,3-dihydro-1-benzothiophene-6-carboxamide Chemical compound NC(N)=NC(=O)C1=C(C)C=C2C(C(C)C)CS(=O)(=O)C2=C1 SEYBCQCNILYQAU-UHFFFAOYSA-N 0.000 description 1
- MGXBNCFMMJQDBN-UHFFFAOYSA-N n-(diaminomethylidene)-5-methyl-3-methylidene-1,1-dioxo-1-benzothiophene-6-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC2=C1S(=O)(=O)CC2=C MGXBNCFMMJQDBN-UHFFFAOYSA-N 0.000 description 1
- LDYDOWFHGQAVQP-UHFFFAOYSA-N n-(diaminomethylidene)-6-ethyl-1,1-dioxo-4h-thiochromene-7-carboxamide Chemical compound C1C=CS(=O)(=O)C2=C1C=C(CC)C(C(=O)N=C(N)N)=C2 LDYDOWFHGQAVQP-UHFFFAOYSA-N 0.000 description 1
- LKMAZLMEXRMSMB-UHFFFAOYSA-N n-(diaminomethylidene)-6-ethyl-2,2-dimethyl-1,1-dioxothiochromene-7-carboxamide Chemical compound C1=CC(C)(C)S(=O)(=O)C2=C1C=C(CC)C(C(=O)N=C(N)N)=C2 LKMAZLMEXRMSMB-UHFFFAOYSA-N 0.000 description 1
- CYHCXUIUKSWCJX-UHFFFAOYSA-N n-(diaminomethylidene)-6-ethyl-2-methyl-1,1-dioxo-4h-3,1$l^{6}-benzoxathiine-7-carboxamide Chemical compound C1OC(C)S(=O)(=O)C2=C1C=C(CC)C(C(=O)N=C(N)N)=C2 CYHCXUIUKSWCJX-UHFFFAOYSA-N 0.000 description 1
- WATHIYIVRJMUBY-UHFFFAOYSA-N n-(diaminomethylidene)-6-ethyl-2-methyl-1,1-dioxo-4h-thiochromene-7-carboxamide Chemical compound C1C=C(C)S(=O)(=O)C2=C1C=C(CC)C(C(=O)N=C(N)N)=C2 WATHIYIVRJMUBY-UHFFFAOYSA-N 0.000 description 1
- ZZIDRZDOQYHWDJ-UHFFFAOYSA-N n-(diaminomethylidene)-6-ethyl-3,3-dioxo-1,3$l^{6}-benzoxathiole-5-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC2=C1S(=O)(=O)CO2 ZZIDRZDOQYHWDJ-UHFFFAOYSA-N 0.000 description 1
- XABFWFRSZYNMML-UHFFFAOYSA-N n-(diaminomethylidene)-6-ethyl-4,4-dimethyl-2,3-dihydrothiochromene-7-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC2=C1SCCC2(C)C XABFWFRSZYNMML-UHFFFAOYSA-N 0.000 description 1
- LDQQKNKMCMHRJZ-UHFFFAOYSA-N n-(diaminomethylidene)-7-ethyl-2,2-dimethyl-4,4-dioxo-3h-1,4$l^{6}-benzoxathiine-6-carboxamide Chemical compound O1C(C)(C)CS(=O)(=O)C2=C1C=C(CC)C(C(=O)N=C(N)N)=C2 LDQQKNKMCMHRJZ-UHFFFAOYSA-N 0.000 description 1
- JSPGVOBAXRMRCP-UHFFFAOYSA-N n-(diaminomethylidene)-7-ethyl-4,4-dioxo-2,3-dihydro-1,4$l^{6}-benzoxathiine-6-carboxamide Chemical compound O1CCS(=O)(=O)C2=C1C=C(CC)C(C(=O)N=C(N)N)=C2 JSPGVOBAXRMRCP-UHFFFAOYSA-N 0.000 description 1
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 description 1
- GDJYIXGPYCKDOV-UHFFFAOYSA-N n-phenylthiohydroxylamine Chemical class SNC1=CC=CC=C1 GDJYIXGPYCKDOV-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 208000017497 prostate disease Diseases 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000894 saliuretic effect Effects 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
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 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
- 238000011477 surgical intervention Methods 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
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- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19548708A DE19548708A1 (de) | 1995-12-23 | 1995-12-23 | Cyclische Sulfone |
| PCT/EP1996/005645 WO1997023476A1 (de) | 1995-12-23 | 1996-12-16 | HETEROCYCLYLKONDENSIERTE BENZOYLGUANIDINE, DEREN HERSTELLUNG UND DEREN VERWENDUNG ALS INHIBITOREN DES ZELLULÄREN Na+/H+-ANTIPORTERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK81598A3 true SK81598A3 (en) | 1999-01-11 |
Family
ID=7781400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK815-98A SK81598A3 (en) | 1995-12-23 | 1996-12-16 | Cyclic sulfone derivative, preparation thereof and pharmaceutical composition containing the same |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6028069A (pt) |
| EP (1) | EP0873335A1 (pt) |
| JP (1) | JP2000502663A (pt) |
| KR (1) | KR19990076675A (pt) |
| AR (1) | AR004402A1 (pt) |
| AU (1) | AU710048B2 (pt) |
| BR (1) | BR9612200A (pt) |
| CA (1) | CA2241143A1 (pt) |
| CZ (1) | CZ199798A3 (pt) |
| DE (1) | DE19548708A1 (pt) |
| HU (1) | HUP9802920A3 (pt) |
| NO (1) | NO982906L (pt) |
| PL (1) | PL327186A1 (pt) |
| RU (1) | RU2161616C2 (pt) |
| SK (1) | SK81598A3 (pt) |
| TW (1) | TW381091B (pt) |
| WO (1) | WO1997023476A1 (pt) |
| ZA (1) | ZA9610724B (pt) |
Families Citing this family (4)
| 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 |
| JP2002502414A (ja) * | 1997-06-02 | 2002-01-22 | 藤沢薬品工業株式会社 | 細胞中のＮａ▲上＋▼／Ｈ▲上＋▼交換の阻害剤としてのグアニジン誘導体 |
| US6730697B2 (en) * | 2002-02-07 | 2004-05-04 | Aventis Pharma Deutschland Gmbh | Dihydrothiaphenanthrenecarbonylguanidines: composition, process of making, and use as medicament or diagnostic aid |
| TW200614995A (en) * | 2004-11-10 | 2006-05-16 | Nicholas Piramal India Ltd | Tricyclic guanidine derivatives as sodium-proton exchange inhibitors |
Family Cites Families (15)
| 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 |
| ATE198328T1 (de) * | 1992-09-28 | 2001-01-15 | Hoechst Ag | Antiarrhythmische und cardioprotektive substituierte 1(2h)-isochinoline, verfahren zu deren herstellung, diese enthaltende arzneimittel und ihre anwendung für die herstellung eines arzneimittels zur behandlung von herzinsuffizienzen |
| US5514801A (en) * | 1992-12-29 | 1996-05-07 | Monsanto Company | Cyclic sulfone containing retroviral protease inhibitors |
| CA2121391A1 (en) * | 1993-04-28 | 1994-10-29 | Atsuyuki Kojima | Indoloylguanidine derivatives |
| DE4317076A1 (de) * | 1993-05-21 | 1994-11-24 | Bayer Ag | Benzthiophencarbonsäureamid-S-oxide |
| US5607898A (en) * | 1993-08-02 | 1997-03-04 | Idemitsu Kosan Company, Ltd. | Pyrazole derivatives |
| EP0639573A1 (de) * | 1993-08-03 | 1995-02-22 | Hoechst Aktiengesellschaft | Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament |
| US5627194A (en) * | 1993-11-17 | 1997-05-06 | Allelix Biopharmaceuticals Inc. | Anti-viral guanidino-substituted compounds |
| DE4344550A1 (de) * | 1993-12-24 | 1995-06-29 | Hoechst Ag | Substituierte 1-Oxo-1,2-dihydro-isochinolinoyl- und 1,1-Dioxo-2H-1,2-benzothiazinoylguanidine, Verfahrenzu ihrer Herstellung, ihre Verwendung als Medikamentt oder Diagnostikum sowie sie enthaltendes Medikamen |
| EP0791589B1 (en) * | 1994-04-11 | 2002-03-06 | Chugai Seiyaku Kabushiki Kaisha | 4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENES WHICH INHIBIT LDL OXIDATION |
| DE4412334A1 (de) * | 1994-04-11 | 1995-10-19 | Hoechst Ag | Substituierte N-Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US5863936A (en) * | 1995-04-18 | 1999-01-26 | Geron Corporation | Telomerase inhibitors |
| US5821250A (en) * | 1996-02-01 | 1998-10-13 | The Procter & Gamble Company | Dihydrobenzofuran and related compounds useful as anti-inflammatory agents |
| FR2762598A1 (fr) * | 1997-04-25 | 1998-10-30 | Adir | Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennnent |
-
1995
- 1995-12-23 DE DE19548708A patent/DE19548708A1/de not_active Withdrawn
-
1996
- 1996-10-20 AR ARP960105800A patent/AR004402A1/es unknown
- 1996-11-19 TW TW085114208A patent/TW381091B/zh active
- 1996-12-16 HU HU9802920A patent/HUP9802920A3/hu unknown
- 1996-12-16 WO PCT/EP1996/005645 patent/WO1997023476A1/de not_active Ceased
- 1996-12-16 US US09/091,652 patent/US6028069A/en not_active Expired - Fee Related
- 1996-12-16 JP JP9523281A patent/JP2000502663A/ja active Pending
- 1996-12-16 BR BR9612200A patent/BR9612200A/pt not_active Application Discontinuation
- 1996-12-16 CZ CZ981997A patent/CZ199798A3/cs unknown
- 1996-12-16 RU RU98114077/04A patent/RU2161616C2/ru active
- 1996-12-16 AU AU11960/97A patent/AU710048B2/en not_active Ceased
- 1996-12-16 PL PL96327186A patent/PL327186A1/xx unknown
- 1996-12-16 KR KR1019980704787A patent/KR19990076675A/ko not_active Ceased
- 1996-12-16 CA CA002241143A patent/CA2241143A1/en not_active Abandoned
- 1996-12-16 EP EP96943131A patent/EP0873335A1/de not_active Withdrawn
- 1996-12-16 SK SK815-98A patent/SK81598A3/sk unknown
- 1996-12-19 ZA ZA9610724A patent/ZA9610724B/xx unknown
-
1998
- 1998-06-22 NO NO982906A patent/NO982906L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU1196097A (en) | 1997-07-17 |
| KR19990076675A (ko) | 1999-10-15 |
| CZ199798A3 (cs) | 1998-10-14 |
| AR004402A1 (es) | 1998-11-04 |
| US6028069A (en) | 2000-02-22 |
| WO1997023476A1 (de) | 1997-07-03 |
| RU2161616C2 (ru) | 2001-01-10 |
| JP2000502663A (ja) | 2000-03-07 |
| AU710048B2 (en) | 1999-09-09 |
| BR9612200A (pt) | 1999-07-13 |
| DE19548708A1 (de) | 1997-06-26 |
| HUP9802920A2 (hu) | 2000-05-28 |
| PL327186A1 (en) | 1998-11-23 |
| ZA9610724B (en) | 1997-06-26 |
| HUP9802920A3 (en) | 2000-12-28 |
| NO982906D0 (no) | 1998-06-22 |
| MX9804972A (es) | 1998-09-30 |
| TW381091B (en) | 2000-02-01 |
| EP0873335A1 (de) | 1998-10-28 |
| NO982906L (no) | 1998-06-22 |
| CA2241143A1 (en) | 1997-07-03 |
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