BG63301B1 - Арилтио съединения като антибактериални и антивирусни агенти - Google Patents
Арилтио съединения като антибактериални и антивирусни агенти Download PDFInfo
- Publication number
- BG63301B1 BG63301B1 BG101189A BG10118997A BG63301B1 BG 63301 B1 BG63301 B1 BG 63301B1 BG 101189 A BG101189 A BG 101189A BG 10118997 A BG10118997 A BG 10118997A BG 63301 B1 BG63301 B1 BG 63301B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- dithiobis
- methyl
- compound
- phenyl
- phenyldisulfanyl
- Prior art date
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- 239000003443 antiviral agent Substances 0.000 title claims abstract description 11
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 10
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 7
- 125000005110 aryl thio group Chemical group 0.000 title description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 444
- -1 arylthio compound Chemical class 0.000 claims description 202
- SDNJNDFHCODQDQ-UHFFFAOYSA-N n-(2-ethylphenyl)-2-[[2-[(2-ethylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=CC=C1CC SDNJNDFHCODQDQ-UHFFFAOYSA-N 0.000 claims description 150
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 99
- 239000000203 mixture Substances 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 208000036142 Viral infection Diseases 0.000 claims description 11
- 230000009385 viral infection Effects 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 230000000840 anti-viral effect Effects 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229960003767 alanine Drugs 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 230000001580 bacterial effect Effects 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine group Chemical group NO AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- VKPLPDIMEREJJF-UHFFFAOYSA-N 3-methoxybenzamide Chemical compound COC1=CC=CC(C(N)=O)=C1 VKPLPDIMEREJJF-UHFFFAOYSA-N 0.000 claims description 3
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 3
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 3
- IRWATDVXASEANM-UHFFFAOYSA-N [2-[(2-benzoylphenyl)disulfanyl]phenyl]-phenylmethanone Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 IRWATDVXASEANM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229960001153 serine Drugs 0.000 claims description 3
- AOIXPIZWAMYLHK-UHFFFAOYSA-N 2-(2,3-dihydroxypropyldisulfanyl)-n-(4-sulfamoylphenyl)benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)C1=CC=CC=C1SSCC(O)CO AOIXPIZWAMYLHK-UHFFFAOYSA-N 0.000 claims description 2
- MUMMHDPLNMLLKB-UHFFFAOYSA-N 2-[(3-methoxybenzoyl)amino]-4-methylpentanoic acid Chemical compound COC1=CC=CC(C(=O)NC(CC(C)C)C(O)=O)=C1 MUMMHDPLNMLLKB-UHFFFAOYSA-N 0.000 claims description 2
- ZXKZUNBMWOKLHT-UHFFFAOYSA-N 2-[[2-[(4-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]benzoic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O ZXKZUNBMWOKLHT-UHFFFAOYSA-N 0.000 claims description 2
- BZHLQRVJOXSEKT-UHFFFAOYSA-N 2-[[2-[(4-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]propanoic acid Chemical compound OC(=O)C(C)SSC1=CC=CC=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 BZHLQRVJOXSEKT-UHFFFAOYSA-N 0.000 claims description 2
- QTDKOIPCIFSLQY-UHFFFAOYSA-N 2-acetamido-3-[[2-[(4-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]propanoic acid Chemical compound CC(=O)NC(C(O)=O)CSSC1=CC=CC=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 QTDKOIPCIFSLQY-UHFFFAOYSA-N 0.000 claims description 2
- KHVHVWDBXPTKLT-UHFFFAOYSA-N 2-amino-3-methyl-3-[[2-[(4-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]butanoic acid Chemical compound OC(=O)C(N)C(C)(C)SSC1=CC=CC=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 KHVHVWDBXPTKLT-UHFFFAOYSA-N 0.000 claims description 2
- YAVWQKBYOBKXCR-UHFFFAOYSA-N 2-benzamidohexanedioic acid Chemical compound OC(=O)CCCC(C(O)=O)NC(=O)C1=CC=CC=C1 YAVWQKBYOBKXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- ZTVZLYBCZNMWCF-UHFFFAOYSA-N homocystine Chemical compound [O-]C(=O)C([NH3+])CCSSCCC([NH3+])C([O-])=O ZTVZLYBCZNMWCF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- ZUZHNBSWCVOLLK-UHFFFAOYSA-N n-(3-sulfamoylphenyl)benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 ZUZHNBSWCVOLLK-UHFFFAOYSA-N 0.000 claims description 2
- LCZVKKUAUWQDPX-UHFFFAOYSA-N tert-butyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl]amino]acetate Chemical compound CC(=O)OC1=CC=CC=C1CN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1=CC=CC=C1OC(C)=O LCZVKKUAUWQDPX-UHFFFAOYSA-N 0.000 claims description 2
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- VTMLTNXBIUAXRJ-UHFFFAOYSA-N 2-[2-[[2-[(4-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]propanoylamino]acetic acid Chemical compound OC(=O)CNC(=O)C(C)SSC1=CC=CC=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 VTMLTNXBIUAXRJ-UHFFFAOYSA-N 0.000 claims 1
- FPLPKFVXDOMXHH-UHFFFAOYSA-N 2-[[2-[(2-acetamido-2-carboxyethyl)disulfanyl]benzoyl]amino]-3-methylpentanoic acid Chemical compound CCC(C)C(C(O)=O)NC(=O)C1=CC=CC=C1SSCC(NC(C)=O)C(O)=O FPLPKFVXDOMXHH-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- GKTFLKJXZOYBRW-UHFFFAOYSA-N 2-ethylbenzamide Chemical compound CCC1=CC=CC=C1C(N)=O GKTFLKJXZOYBRW-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- WGRPQCFFBRDZFV-UHFFFAOYSA-N 3-methylbenzamide Chemical compound CC1=CC=CC(C(N)=O)=C1 WGRPQCFFBRDZFV-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- KDGXQBKQOABANB-LSLKUGRBSA-N C(=O)(O)C(CC(=O)O)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)N[C@H](C(=O)O)CC(=O)O)C=CC=C1 Chemical compound C(=O)(O)C(CC(=O)O)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)N[C@H](C(=O)O)CC(=O)O)C=CC=C1 KDGXQBKQOABANB-LSLKUGRBSA-N 0.000 claims 1
- IURAMYCAJMCTKF-VYRBHSGPSA-N C(=O)(O)C(CCC(=O)O)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)N[C@H](C(=O)O)CCC(=O)O)C=CC=C1 Chemical compound C(=O)(O)C(CCC(=O)O)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)N[C@H](C(=O)O)CCC(=O)O)C=CC=C1 IURAMYCAJMCTKF-VYRBHSGPSA-N 0.000 claims 1
- 239000001263 FEMA 3042 Substances 0.000 claims 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- SPAHAZQJLHDHFY-UHFFFAOYSA-N methyl 2-[[2-[(4-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 SPAHAZQJLHDHFY-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- FLCWYEUDIOQXEB-UHFFFAOYSA-N morpholin-4-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCOCC1 FLCWYEUDIOQXEB-UHFFFAOYSA-N 0.000 claims 1
- NMNPQVUDXPNPRE-UHFFFAOYSA-N n-(2-hydroxy-1-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1C(CO)NC(=O)C1=CC=CC=C1 NMNPQVUDXPNPRE-UHFFFAOYSA-N 0.000 claims 1
- CWUUKGVTFGECDV-UHFFFAOYSA-N n-(4-sulfamoylphenyl)pyridine-3-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)C1=CC=CN=C1 CWUUKGVTFGECDV-UHFFFAOYSA-N 0.000 claims 1
- IASIJDXUZOLTAH-UHFFFAOYSA-N n-cyclopropylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CC1 IASIJDXUZOLTAH-UHFFFAOYSA-N 0.000 claims 1
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- YUFWGGKEIRULTL-VIFPVBQESA-N tert-butyl (2s)-4-methyl-2-(methylamino)pentanoate Chemical compound CC(C)C[C@H](NC)C(=O)OC(C)(C)C YUFWGGKEIRULTL-VIFPVBQESA-N 0.000 description 1
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- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cereal-Derived Products (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/286,816 US5463122A (en) | 1994-08-05 | 1994-08-05 | Arylthio compounds |
US08/446,917 US5734081A (en) | 1994-08-05 | 1995-06-01 | Arylthio compounds |
PCT/US1995/008802 WO1996004242A1 (en) | 1994-08-05 | 1995-07-11 | Arylthio compounds as antibacterial and antiviral agents |
Publications (2)
Publication Number | Publication Date |
---|---|
BG101189A BG101189A (en) | 1998-03-31 |
BG63301B1 true BG63301B1 (bg) | 2001-09-28 |
Family
ID=26964088
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG101189A BG63301B1 (bg) | 1994-08-05 | 1997-02-04 | Арилтио съединения като антибактериални и антивирусни агенти |
Country Status (27)
Country | Link |
---|---|
US (3) | US5734081A (ro) |
EP (1) | EP0775110B1 (ro) |
JP (1) | JPH10504292A (ro) |
KR (1) | KR20040004371A (ro) |
AT (1) | ATE305923T1 (ro) |
AU (1) | AU710806B2 (ro) |
BG (1) | BG63301B1 (ro) |
CA (1) | CA2193845A1 (ro) |
CZ (1) | CZ26297A3 (ro) |
DE (1) | DE69534502D1 (ro) |
FI (1) | FI970417A (ro) |
HR (1) | HRP950429A2 (ro) |
HU (1) | HUT77653A (ro) |
IS (1) | IS1806B (ro) |
MX (1) | MX9700249A (ro) |
MY (1) | MY113732A (ro) |
NO (1) | NO308656B1 (ro) |
NZ (1) | NZ300073A (ro) |
OA (1) | OA10467A (ro) |
PL (1) | PL181425B1 (ro) |
RO (1) | RO119193B1 (ro) |
RU (1) | RU2156236C2 (ro) |
SK (1) | SK15497A3 (ro) |
SV (1) | SV1995000048A (ro) |
TW (1) | TW313565B (ro) |
UA (1) | UA52588C2 (ro) |
WO (1) | WO1996004242A1 (ro) |
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FR2736914B1 (fr) * | 1995-07-21 | 1997-08-22 | Adir | Nouveaux derives d'acide aminophenylphosphonique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
IL123903A0 (en) * | 1995-12-15 | 1998-10-30 | Warner Lambert Co | Method of making [S-(R*,R*]-3- methyl-2- (2-oxo-3H- benzo [d] isothiazol-2-yl) pentanoic acid |
ZA974703B (en) * | 1996-05-30 | 1997-12-30 | Bayer Ag | Substituted sulfonylamino(thio)carbonyl compounds. |
CA2285446A1 (en) * | 1997-03-13 | 1998-09-17 | Smithkline Beecham P.L.C. | Pyrrolidine and thiazole derivatives with metallo-beta-lactamase inhibitory properties |
DE19735120A1 (de) | 1997-08-13 | 1999-02-18 | Peter Hans Prof D Hofschneider | Verwendung von Thiolverbindungen zur Inaktivierung von Viren |
FR2779430B1 (fr) * | 1998-05-25 | 2001-07-13 | Pasteur Institut | Dithio-bis-nitrobenzenes substitues et leurs applications |
ATE336483T1 (de) * | 1998-06-19 | 2006-09-15 | Us Health | Thiolester und ihre anwendungen |
US6706729B1 (en) | 1998-06-19 | 2004-03-16 | The United States Of America As Represented By The Department Of Health And Human Services | Thiolesters and uses thereof |
UA74781C2 (en) * | 1999-04-02 | 2006-02-15 | Abbott Lab | Antiinflammatory and immumosuppressive compounds inhibiting cell adhesion |
US6372802B2 (en) | 2000-05-19 | 2002-04-16 | Alcon Universal Ltd. | Aniline disulfide derivatives for treating allergic diseases |
PT1282599E (pt) | 2000-05-19 | 2006-08-31 | Alcon Inc | Derivados dissulfureto uteis para tratar doencas alergicas |
ATE302601T1 (de) | 2000-05-19 | 2005-09-15 | Alcon Inc | Zusammensetzungen enthaltend ein benzamiddisulfid-derivat zur behandlung allergischer krankheiten |
WO2002056819A2 (en) * | 2000-12-21 | 2002-07-25 | Polymer Group Inc. | Absorbent articles with odor control |
US8163776B2 (en) * | 2001-01-10 | 2012-04-24 | Grassetti Family Trust | Method of immunomodulation using thione-forming disulfides |
EP1390029B1 (en) | 2001-04-11 | 2009-12-16 | Idenix (Cayman) Limited | Phenylindoles for the treatment of hiv |
AU2002367173A1 (en) * | 2001-12-21 | 2003-07-15 | Achillion Pharmaceuticals, Inc. | Antifungal compositions |
US7101676B2 (en) * | 2002-01-11 | 2006-09-05 | Douglas Buechter | Methods for identifying compounds which inhibit binding of nucleocapsid 7 protein to HIV-1 RNA |
US7365090B2 (en) * | 2002-08-07 | 2008-04-29 | Idenix Pharmaceuticals, Inc. | Substituted phenylindoles for the treatment of HIV |
MXPA05006196A (es) * | 2002-12-10 | 2006-01-27 | Virochem Pharma Inc | Compuestos y metodos para el tratamiento o prevencion de infecciones por flavivirus. |
WO2004056766A1 (en) * | 2002-12-19 | 2004-07-08 | Vertex Pharmaceuticals Incorporated | Inhibitors of tace |
EP1620407A2 (en) * | 2003-04-28 | 2006-02-01 | Idenix (Cayman) Limited | Oxo-pyrimidine compounds |
ES2711313T3 (es) * | 2003-12-26 | 2019-05-03 | Masatoshi Hagiwara | Método de regulación de la fosforilación de la proteína SR y agentes antivirales que comprenden el regulador de la actividad de la proteína SR como ingrediente activo |
NZ554232A (en) * | 2004-09-17 | 2010-09-30 | Idenix Pharmaceuticals Inc | Phosphoindoles as HIV inhibitors |
US20060185098A1 (en) * | 2004-12-03 | 2006-08-24 | Sylvain Kravtchenko | Composition for bleaching and simultaneously dyeing keratin fibers, comprising 7-(6'-methylphenylazo)-1-acetamido-3,6-disulfo-8-hydroxynaphthalene |
JP2010504978A (ja) * | 2006-09-29 | 2010-02-18 | アイデニクス ファーマシューティカルズ,インコーポレーテッド | Hiv阻害剤としての鏡像異性的に純粋なホスホインドール |
EP1911451A1 (en) * | 2006-10-10 | 2008-04-16 | INSERM (Institut National de la Santé et de la Recherche Medicale) | Protein-kinase CK2 inhibitors and their therapeutic applications |
JP2010509205A (ja) | 2006-11-07 | 2010-03-25 | プロテオロジクス リミテッド | Posh及びposh−ap阻害剤としてのピリミジン誘導体 |
WO2008112939A2 (en) * | 2007-03-13 | 2008-09-18 | Board Of Regents, The University Of Texas System | Composition and method for making oligo-benzamide compounds |
JP2013528174A (ja) | 2010-05-28 | 2013-07-08 | ザ ボード オブ リージェンツ オブ ザ ユニバーシティー オブ テキサス システム | オリゴベンズアミド化合物およびそれらの使用 |
US8835493B2 (en) | 2011-11-23 | 2014-09-16 | Board Of Regents, The University Of Texas System | Oligo-benzamide compounds for use in treating cancers |
WO2013078277A1 (en) | 2011-11-23 | 2013-05-30 | The Board Of Regents Of The University Of Texas System | Oligo-benzamide compounds and their use in treating cancers |
US10730828B2 (en) | 2015-10-19 | 2020-08-04 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as nitroxyl donors |
JP6814312B1 (ja) * | 2020-02-05 | 2021-01-13 | 株式会社タイショーテクノス | 抗ウイルス剤及び物品に抗ウイルス性を付与する方法 |
CN111647034B (zh) * | 2020-05-13 | 2021-05-28 | 山东大学 | 2-巯基苯甲酰胺硫酯类化合物及其制备方法和应用 |
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DE724034C (de) * | 1938-11-04 | 1942-08-17 | Algemeene Kunstvezel Mij N V | Verfahren zum Erzeugen farbiger Glasfasern |
US3012039A (en) * | 1958-03-14 | 1961-12-05 | Ici Ltd | 2-p-chlorobenzyl-1, 2-benzisothiazolone |
US3517022A (en) * | 1967-10-03 | 1970-06-23 | Rohm & Haas | Certain 2-carbamoyl-1,2-benzisothiazolones |
US3574858A (en) * | 1968-07-09 | 1971-04-13 | Fmc Corp | Microbiocide for controlling bacteria in water |
US3736280A (en) * | 1969-10-13 | 1973-05-29 | Sherwin Williams Co | Fungicidal compositions and methods of prohibiting the growth thereof |
US3663616A (en) * | 1969-10-13 | 1972-05-16 | Sherwin Williams Co | Bis(2-carbamylphenyl)disulfides |
GB1306493A (en) * | 1970-04-27 | 1973-02-14 | Sherwin Williams Co | Aromatic sulphenamides the preparation thereof and cyclization thereof |
US3661974A (en) * | 1970-04-27 | 1972-05-09 | Sherwin Williams Co | 2-carbalkoxy-phenyl sulfenamides |
US3761489A (en) * | 1971-12-20 | 1973-09-25 | Sherwin Williams Co | Substituted n-alkyl benzisothiazolinones |
US3786150A (en) * | 1971-12-27 | 1974-01-15 | Fmc Corp | Fungicidal use of certain benz(d)isothiazoles |
US3965107A (en) * | 1974-07-08 | 1976-06-22 | Rohm And Haas Company | Isothiazolopyridinones |
GB1532984A (en) * | 1975-04-10 | 1978-11-22 | Ici Ltd | Method for the control of micro-organisms |
DE2602643C2 (de) * | 1976-01-24 | 1984-12-20 | Bayer Ag, 5090 Leverkusen | 1,2-Benzisothiazolinone-3, Verfahren zu ihrer Herstellung sowie Arzneimittel |
GB1560726A (en) * | 1976-04-28 | 1980-02-06 | Beecham Group Ltd | Isothiazolo-pyridines |
EP0006227B1 (en) * | 1978-06-16 | 1984-12-27 | Kyowa Hakko Kogyo Co., Ltd | Antithrombotic pharmaceutical preparation containing 2,2'-dithiobis benzamide derivatives and new 2,2'-dithiobis benzamide derivatives |
US4479950A (en) * | 1982-11-05 | 1984-10-30 | Usv Pharmaceutical Corporation | Aroylaminoacid disulfides |
DE3411385A1 (de) * | 1984-03-28 | 1985-10-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von o,o'-dithiobenzamiden |
US4975367A (en) * | 1986-04-04 | 1990-12-04 | Miles Inc. | Catalytic test composition intended to produce a range of colors |
JPH0477476A (ja) * | 1990-07-19 | 1992-03-11 | Sankyo Co Ltd | 抗潰瘍剤 |
IE913697A1 (en) * | 1990-10-22 | 1992-04-22 | Res Corp Technologies Inc | Aryl and heteroaryl, compounds having anti-retrovirus¹activity |
PT100914A (pt) * | 1991-09-30 | 1993-10-29 | Jess G Thoene | Uso de compostos capazes de sofrer uma permuta mista com dissulfureto, com uma ligacao dissulfureto, no tratamento de infeccao por hiv |
-
1995
- 1995-06-01 US US08/446,917 patent/US5734081A/en not_active Expired - Fee Related
- 1995-06-07 US US08/474,875 patent/US5668291A/en not_active Expired - Fee Related
- 1995-07-11 AU AU30087/95A patent/AU710806B2/en not_active Ceased
- 1995-07-11 MX MX9700249A patent/MX9700249A/es unknown
- 1995-07-11 NZ NZ300073A patent/NZ300073A/xx unknown
- 1995-07-11 PL PL95318540A patent/PL181425B1/pl not_active IP Right Cessation
- 1995-07-11 KR KR10-2003-7003049A patent/KR20040004371A/ko not_active Application Discontinuation
- 1995-07-11 RO RO97-00227A patent/RO119193B1/ro unknown
- 1995-07-11 EP EP95926276A patent/EP0775110B1/en not_active Expired - Lifetime
- 1995-07-11 WO PCT/US1995/008802 patent/WO1996004242A1/en not_active Application Discontinuation
- 1995-07-11 HU HU9700349A patent/HUT77653A/hu unknown
- 1995-07-11 SK SK154-97A patent/SK15497A3/sk unknown
- 1995-07-11 RU RU97103207/04A patent/RU2156236C2/ru not_active IP Right Cessation
- 1995-07-11 DE DE69534502T patent/DE69534502D1/de not_active Expired - Lifetime
- 1995-07-11 JP JP8506523A patent/JPH10504292A/ja not_active Abandoned
- 1995-07-11 CA CA002193845A patent/CA2193845A1/en not_active Abandoned
- 1995-07-11 AT AT95926276T patent/ATE305923T1/de not_active IP Right Cessation
- 1995-07-11 CZ CZ97262A patent/CZ26297A3/cs unknown
- 1995-07-25 TW TW084107669A patent/TW313565B/zh active
- 1995-07-26 HR HR08/446,917A patent/HRP950429A2/hr not_active Application Discontinuation
- 1995-08-04 MY MYPI95002289A patent/MY113732A/en unknown
- 1995-08-07 SV SV1995000048A patent/SV1995000048A/es unknown
- 1995-11-07 UA UA97020486A patent/UA52588C2/uk unknown
-
1996
- 1996-12-13 OA OA60937A patent/OA10467A/en unknown
-
1997
- 1997-01-31 FI FI970417A patent/FI970417A/fi not_active IP Right Cessation
- 1997-02-03 IS IS4425A patent/IS1806B/is unknown
- 1997-02-04 BG BG101189A patent/BG63301B1/bg unknown
- 1997-02-04 NO NO970495A patent/NO308656B1/no not_active IP Right Cessation
- 1997-05-15 US US08/857,116 patent/US5929114A/en not_active Expired - Fee Related
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