DE1768337C2 - 2-Phenylbenzo eckige Klammer auf b eckige Klammer zu -thiophen- und 2-Phenylnaphtho eckige Klammer auf 2,3b eckige Klammer zu -thiophen-3 (2H)on-1,1-dioxide und Verfahren zu ihrer Herstellung - Google Patents
2-Phenylbenzo eckige Klammer auf b eckige Klammer zu -thiophen- und 2-Phenylnaphtho eckige Klammer auf 2,3b eckige Klammer zu -thiophen-3 (2H)on-1,1-dioxide und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1768337C2 DE1768337C2 DE1768337A DE1768337A DE1768337C2 DE 1768337 C2 DE1768337 C2 DE 1768337C2 DE 1768337 A DE1768337 A DE 1768337A DE 1768337 A DE1768337 A DE 1768337A DE 1768337 C2 DE1768337 C2 DE 1768337C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- thiophene
- mixture
- water
- square bracket
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 24
- 238000002360 preparation method Methods 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 49
- 239000000243 solution Substances 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- -1 C1-substituted phenyl Chemical group 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- AFXHYPLRPZTVDW-UHFFFAOYSA-N C1(=CC=CC=C1)C1C(C2=C(S1(=O)=O)C=C1C=CC=CC1=C2)=O Chemical class C1(=CC=CC=C1)C1C(C2=C(S1(=O)=O)C=C1C=CC=CC1=C2)=O AFXHYPLRPZTVDW-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 108010094028 Prothrombin Proteins 0.000 description 6
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- 241000700159 Rattus Species 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
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- 239000007787 solid Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- CHGIHNHFMQGPDX-UHFFFAOYSA-N 1,1-dioxothiophen-3-one Chemical compound O=C1CS(=O)(=O)C=C1 CHGIHNHFMQGPDX-UHFFFAOYSA-N 0.000 description 5
- XLFFYDFFAKJIEN-UHFFFAOYSA-N 3-sulfanylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C=C(S)C(C(=O)O)=CC2=C1 XLFFYDFFAKJIEN-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- ZGUXUDQCPNXZSF-UHFFFAOYSA-N 1,1-dioxo-2-phenyl-1-benzothiophen-3-one Chemical class O=S1(=O)C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 ZGUXUDQCPNXZSF-UHFFFAOYSA-N 0.000 description 4
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 238000005245 sintering Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UGIFXPKISZRMOD-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylsulfonyl]-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1S(=O)(=O)CC1=CC=C(Cl)C=C1 UGIFXPKISZRMOD-UHFFFAOYSA-N 0.000 description 3
- LCISFYAQKHOWBP-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(Cl)C(C#N)=C1 LCISFYAQKHOWBP-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000023555 blood coagulation Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000002085 enols Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003613 toluenes Chemical class 0.000 description 3
- 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 2
- HGQXABDABPJWSP-UHFFFAOYSA-N 2-benzylbenzenecarbothioic s-acid Chemical compound OC(=S)C1=CC=CC=C1CC1=CC=CC=C1 HGQXABDABPJWSP-UHFFFAOYSA-N 0.000 description 2
- JJFQTKHGJJWAJZ-UHFFFAOYSA-N 2-benzylsulfanyl-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(C(F)(F)F)=CC=C1SCC1=CC=CC=C1 JJFQTKHGJJWAJZ-UHFFFAOYSA-N 0.000 description 2
- ZUUSJUMOXCIBBW-UHFFFAOYSA-N 2-benzylsulfanyl-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1SCC1=CC=CC=C1 ZUUSJUMOXCIBBW-UHFFFAOYSA-N 0.000 description 2
- LZEFKLWKUPAQMV-UHFFFAOYSA-N 2-benzylsulfonyl-5-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)CC1=CC=CC=C1 LZEFKLWKUPAQMV-UHFFFAOYSA-N 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 2
- VWIXUROTJVJZOL-UHFFFAOYSA-N 2-phenyl-1-benzothiophen-3-one Chemical compound S1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 VWIXUROTJVJZOL-UHFFFAOYSA-N 0.000 description 2
- LBMHPHUSGIEGHJ-UHFFFAOYSA-N 2-phenyl-1-benzothiophene Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=C1 LBMHPHUSGIEGHJ-UHFFFAOYSA-N 0.000 description 2
- XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-amino-2-naphthoic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-UHFFFAOYSA-N 0.000 description 2
- SYMBQOXLZUDQRT-UHFFFAOYSA-N 3-benzylsulfonylnaphthalene-2-carboxylic acid Chemical class C(C1=CC=CC=C1)S(=O)(=O)C=1C(=CC2=CC=CC=C2C=1)C(=O)O SYMBQOXLZUDQRT-UHFFFAOYSA-N 0.000 description 2
- PKYWFLCUINZGET-UHFFFAOYSA-N 5-methyl-2-[(3-nitrophenyl)methylsulfonyl]benzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1S(=O)(=O)CC1=CC=CC([N+]([O-])=O)=C1 PKYWFLCUINZGET-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 1
- PNAZUQUHTIOEHF-UHFFFAOYSA-N (3-methylphenyl)methanethiol Chemical compound CC1=CC=CC(CS)=C1 PNAZUQUHTIOEHF-UHFFFAOYSA-N 0.000 description 1
- LXCYNALXWGQUIK-UHFFFAOYSA-N 1,1-dioxo-1-benzothiophen-3-one Chemical class C1=CC=C2C(=O)CS(=O)(=O)C2=C1 LXCYNALXWGQUIK-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- XGASTRVQNVVYIZ-UHFFFAOYSA-N 1-(chloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CCl)=C1 XGASTRVQNVVYIZ-UHFFFAOYSA-N 0.000 description 1
- APGGSERFJKEWFG-UHFFFAOYSA-N 1-(chloromethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CCl)=C1 APGGSERFJKEWFG-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- AVSVJSGDSPDFLH-UHFFFAOYSA-N 2,2,2-trifluoroethylbenzene Chemical class FC(F)(F)CC1=CC=CC=C1 AVSVJSGDSPDFLH-UHFFFAOYSA-N 0.000 description 1
- BDNYKXUZUFMWEP-UHFFFAOYSA-N 2-(3-methylphenyl)-5-nitro-1,1-dioxo-1-benzothiophen-3-one Chemical compound [N+](=O)([O-])C1=CC2=C(S(C(C2=O)C=2C=C(C=CC2)C)(=O)=O)C=C1 BDNYKXUZUFMWEP-UHFFFAOYSA-N 0.000 description 1
- GDYQRXYRQKCJEU-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methyl-1,1-dioxo-1-benzothiophen-3-one Chemical compound CC1=CC2=C(S(C(C2=O)C2=CC=C(C=C2)Cl)(=O)=O)C=C1 GDYQRXYRQKCJEU-UHFFFAOYSA-N 0.000 description 1
- NNJYLDAQMJZAQL-UHFFFAOYSA-N 2-[(3-methylphenyl)methylsulfanyl]-5-nitrobenzoic acid Chemical compound CC1=CC=CC(CSC=2C(=CC(=CC=2)[N+]([O-])=O)C(O)=O)=C1 NNJYLDAQMJZAQL-UHFFFAOYSA-N 0.000 description 1
- LPIOTOJTKOCLMF-UHFFFAOYSA-N 2-[(3-methylphenyl)methylsulfonyl]-5-(trifluoromethyl)benzoic acid Chemical compound CC=1C=C(CS(=O)(=O)C2=C(C(=O)O)C=C(C=C2)C(F)(F)F)C=CC1 LPIOTOJTKOCLMF-UHFFFAOYSA-N 0.000 description 1
- PGABZDURYXXCOM-UHFFFAOYSA-N 2-[(3-methylphenyl)methylsulfonyl]-5-nitrobenzoic acid Chemical compound CC1=CC=CC(CS(=O)(=O)C2=C(C=C(C=C2)[N+]([O-])=O)C(O)=O)=C1 PGABZDURYXXCOM-UHFFFAOYSA-N 0.000 description 1
- CHKXFIAAFVOWCM-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]-1-benzothiophene Chemical compound FC(F)(F)C1=CC=CC(C=2SC3=CC=CC=C3C=2)=C1 CHKXFIAAFVOWCM-UHFFFAOYSA-N 0.000 description 1
- GLCQUPLYYXSPQB-UHFFFAOYSA-N 2-amino-5-(trifluoromethyl)benzoic acid Chemical compound NC1=CC=C(C(F)(F)F)C=C1C(O)=O GLCQUPLYYXSPQB-UHFFFAOYSA-N 0.000 description 1
- ZLCIALUBLCAXPL-UHFFFAOYSA-N 2-amino-5-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C(F)(F)F)C=C1C#N ZLCIALUBLCAXPL-UHFFFAOYSA-N 0.000 description 1
- WSZZROXSWHOXRS-UHFFFAOYSA-N 2-benzylsulfanyl-5-(trifluoromethyl)benzonitrile Chemical compound N#CC1=CC(C(F)(F)F)=CC=C1SCC1=CC=CC=C1 WSZZROXSWHOXRS-UHFFFAOYSA-N 0.000 description 1
- LCVQODRQKCOTDJ-UHFFFAOYSA-N 2-benzylsulfanylbenzonitrile Chemical class N#CC1=CC=CC=C1SCC1=CC=CC=C1 LCVQODRQKCOTDJ-UHFFFAOYSA-N 0.000 description 1
- KECKPXWTGMZKGN-UHFFFAOYSA-N 2-benzylsulfonyl-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1S(=O)(=O)CC1=CC=CC=C1 KECKPXWTGMZKGN-UHFFFAOYSA-N 0.000 description 1
- GMVRFXQEJYYRMJ-UHFFFAOYSA-N 2-benzylsulfonylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1S(=O)(=O)CC1=CC=CC=C1 GMVRFXQEJYYRMJ-UHFFFAOYSA-N 0.000 description 1
- QADWHSDYQFHZPU-UHFFFAOYSA-N 2-hydroxy-5-methylbenzenecarbothioic s-acid Chemical compound CC1=CC=C(O)C(C(S)=O)=C1 QADWHSDYQFHZPU-UHFFFAOYSA-N 0.000 description 1
- LWJQGKJCZOGGPJ-UHFFFAOYSA-N 2-methylsulfanylbenzoic acid Chemical compound CSC1=CC=CC=C1C(O)=O LWJQGKJCZOGGPJ-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- QUEKGYQTRJVEQC-UHFFFAOYSA-N 2516-96-3 Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl QUEKGYQTRJVEQC-UHFFFAOYSA-N 0.000 description 1
- ONYMMSMPASZDFM-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylsulfanyl]naphthalene-2-carboxylic acid Chemical compound OC(=O)c1cc2ccccc2cc1SCc1ccc(Cl)cc1 ONYMMSMPASZDFM-UHFFFAOYSA-N 0.000 description 1
- XZBHRTQKLCGAGU-UHFFFAOYSA-N 3-benzylsulfanylnaphthalene-2-carboxylic acid Chemical compound C(C1=CC=CC=C1)SC=1C(=CC2=CC=CC=C2C=1)C(=O)O XZBHRTQKLCGAGU-UHFFFAOYSA-N 0.000 description 1
- WLPAZXIPZOCUEX-UHFFFAOYSA-N 3-sulfinonaphthalene-2-carboxylic acid Chemical compound S(=O)(O)C=1C(=CC2=CC=CC=C2C1)C(=O)O WLPAZXIPZOCUEX-UHFFFAOYSA-N 0.000 description 1
- VTEQAIYDWOIFDA-UHFFFAOYSA-N 5-methyl-2-[[3-(trifluoromethyl)phenyl]methylsulfanyl]benzoic acid Chemical compound CC=1C=CC(=C(C(=O)O)C1)SCC1=CC(=CC=C1)C(F)(F)F VTEQAIYDWOIFDA-UHFFFAOYSA-N 0.000 description 1
- AYVSGNMNBGVVAE-UHFFFAOYSA-N 5-methyl-2-[[3-(trifluoromethyl)phenyl]methylsulfonyl]benzoyl chloride Chemical compound CC=1C=CC(=C(C(=O)Cl)C1)S(=O)(=O)CC1=CC(=CC=C1)C(F)(F)F AYVSGNMNBGVVAE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DWGGWHYDZDEEJP-UHFFFAOYSA-N FC(C=1C=C(C=CC1)C1C(C2=C(S1(=O)=O)C=C1C=CC=CC1=C2)=O)(F)F Chemical class FC(C=1C=C(C=CC1)C1C(C2=C(S1(=O)=O)C=C1C=CC=CC1=C2)=O)(F)F DWGGWHYDZDEEJP-UHFFFAOYSA-N 0.000 description 1
- RSELDGDNDQSPJW-UHFFFAOYSA-N FC(C=1C=C(CS(=O)(=O)C=2C(=CC3=CC=CC=C3C=2)C(=O)O)C=CC=1)(F)F Chemical compound FC(C=1C=C(CS(=O)(=O)C=2C(=CC3=CC=CC=C3C=2)C(=O)O)C=CC=1)(F)F RSELDGDNDQSPJW-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 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 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- UADKZIGVRVCUEY-UHFFFAOYSA-N OC(C1=CC2=CC=CC=C2C=C1S(CC(C=C1)=CC=C1Cl)(=O)=O)=O Chemical compound OC(C1=CC2=CC=CC=C2C=C1S(CC(C=C1)=CC=C1Cl)(=O)=O)=O UADKZIGVRVCUEY-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- GQANROMQHUJAGR-UHFFFAOYSA-N S1(C2=C(C(C1)=O)C=C1C=CC=CC1=C2)(=O)=O Chemical compound S1(C2=C(C(C1)=O)C=C1C=CC=CC1=C2)(=O)=O GQANROMQHUJAGR-UHFFFAOYSA-N 0.000 description 1
- 206010042674 Swelling Diseases 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 150000005524 benzylchlorides Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000007911 parenteral administration Methods 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical class O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical class OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- LISVMKXUGCLOOC-UHFFFAOYSA-N trifluoromethylsulfinylmethylbenzene Chemical class FC(F)(F)S(=O)CC1=CC=CC=C1 LISVMKXUGCLOOC-UHFFFAOYSA-N 0.000 description 1
- AZTKXNSPQZIUDX-UHFFFAOYSA-N trifluoromethylsulfonylmethylbenzene Chemical class FC(F)(F)S(=O)(=O)CC1=CC=CC=C1 AZTKXNSPQZIUDX-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07D333/74—Naphthothiophenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63540667A | 1967-05-02 | 1967-05-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1768337B1 DE1768337B1 (de) | 1972-05-31 |
| DE1768337C2 true DE1768337C2 (de) | 1973-01-04 |
Family
ID=24547666
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1768337A Expired DE1768337C2 (de) | 1967-05-02 | 1968-05-02 | 2-Phenylbenzo eckige Klammer auf b eckige Klammer zu -thiophen- und 2-Phenylnaphtho eckige Klammer auf 2,3b eckige Klammer zu -thiophen-3 (2H)on-1,1-dioxide und Verfahren zu ihrer Herstellung |
| DE19681793663 Pending DE1793663A1 (de) | 1967-05-02 | 1968-05-02 | Neue o-mercapto-,o-sulfinyl- und o-sulfonyl-substituierte Benzoesaeuren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681793663 Pending DE1793663A1 (de) | 1967-05-02 | 1968-05-02 | Neue o-mercapto-,o-sulfinyl- und o-sulfonyl-substituierte Benzoesaeuren |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3502717A (ref) |
| JP (1) | JPS5116419B1 (ref) |
| BE (1) | BE714440A (ref) |
| CH (1) | CH494236A (ref) |
| DE (2) | DE1768337C2 (ref) |
| ES (1) | ES353408A1 (ref) |
| FR (2) | FR8312M (ref) |
| GB (2) | GB1221327A (ref) |
| NL (1) | NL6806137A (ref) |
| SE (2) | SE353094B (ref) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3954994A (en) * | 1968-10-03 | 1976-05-04 | Pfizer Inc. | Intermediates for preparing hipolipemic agents and method of lowering the blood lipid level in mammals with said agents |
| NL7000883A (ref) * | 1969-01-23 | 1970-07-27 | ||
| US3855285A (en) * | 1971-06-21 | 1974-12-17 | Pfizer | Acylmethylthio-trifluoromethyl-benzoic acids |
| DE3618076A1 (de) * | 1986-06-02 | 1987-12-03 | Kernforschungsanlage Juelich | Verfahren zur mikrobiellen anaeroben gewinnung von essigsaeure |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB780520A (en) * | 1955-03-11 | 1957-08-07 | Boots Pure Drug Co Ltd | New sulphur containing compounds |
-
1967
- 1967-05-02 US US635406A patent/US3502717A/en not_active Expired - Lifetime
-
1968
- 1968-04-19 GB GB37609/69A patent/GB1221327A/en not_active Expired
- 1968-04-19 GB GB08733/68A patent/GB1221326A/en not_active Expired
- 1968-04-30 FR FR150142A patent/FR8312M/fr not_active Expired
- 1968-04-30 BE BE714440D patent/BE714440A/xx unknown
- 1968-05-01 NL NL6806137A patent/NL6806137A/xx unknown
- 1968-05-01 JP JP43028829A patent/JPS5116419B1/ja active Pending
- 1968-05-01 CH CH648268A patent/CH494236A/fr not_active IP Right Cessation
- 1968-05-02 ES ES353408A patent/ES353408A1/es not_active Expired
- 1968-05-02 DE DE1768337A patent/DE1768337C2/de not_active Expired
- 1968-05-02 DE DE19681793663 patent/DE1793663A1/de active Pending
- 1968-05-02 SE SE05923/68A patent/SE353094B/xx unknown
-
1969
- 1969-05-02 SE SE06492/71A patent/SE369599B/xx unknown
- 1969-12-08 FR FR183315A patent/FR8414M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR8414M (ref) | 1971-03-31 |
| SE353094B (ref) | 1973-01-22 |
| BE714440A (ref) | 1968-10-30 |
| GB1221326A (en) | 1971-02-03 |
| NL6806137A (ref) | 1968-11-04 |
| JPS5116419B1 (ref) | 1976-05-24 |
| CH494236A (fr) | 1970-07-31 |
| DE1793663A1 (de) | 1972-03-09 |
| GB1221327A (en) | 1971-02-03 |
| SE369599B (ref) | 1974-09-09 |
| DE1768337B1 (de) | 1972-05-31 |
| US3502717A (en) | 1970-03-24 |
| FR8312M (ref) | 1970-11-30 |
| ES353408A1 (es) | 1969-08-16 |
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