ES2354378T3 - Derivados de arilsulfonamida para usar como antagonistas de ccr3 en el tratamiento de trastornos inflamatorios e inmunológicos. - Google Patents
Derivados de arilsulfonamida para usar como antagonistas de ccr3 en el tratamiento de trastornos inflamatorios e inmunológicos. Download PDFInfo
- Publication number
- ES2354378T3 ES2354378T3 ES07013793T ES07013793T ES2354378T3 ES 2354378 T3 ES2354378 T3 ES 2354378T3 ES 07013793 T ES07013793 T ES 07013793T ES 07013793 T ES07013793 T ES 07013793T ES 2354378 T3 ES2354378 T3 ES 2354378T3
- Authority
- ES
- Spain
- Prior art keywords
- piperazine
- nitrophenylsulfonyl
- dimethylphenoxy
- piperazin
- nitro
- 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 - Lifetime
Links
- 238000011282 treatment Methods 0.000 title claims description 12
- 230000002757 inflammatory effect Effects 0.000 title claims description 6
- 208000026278 immune system disease Diseases 0.000 title description 2
- 239000005557 antagonist Substances 0.000 title 1
- 208000027866 inflammatory disease Diseases 0.000 title 1
- -1 4-chlorophenoxy Chemical group 0.000 claims abstract description 131
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 11
- NFRVUXGKEBPMMO-UHFFFAOYSA-N 1-[2-(3-fluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC(F)=C1 NFRVUXGKEBPMMO-UHFFFAOYSA-N 0.000 claims abstract 5
- JJCOLCAPAYHLMB-UHFFFAOYSA-N 1-[2-(3-methylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 JJCOLCAPAYHLMB-UHFFFAOYSA-N 0.000 claims abstract 5
- RHOQUTJHBSGHMT-UHFFFAOYSA-N 1-(5-nitro-2-phenoxyphenyl)sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1 RHOQUTJHBSGHMT-UHFFFAOYSA-N 0.000 claims abstract 3
- ZWAXHPFRFWAHJH-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 ZWAXHPFRFWAHJH-UHFFFAOYSA-N 0.000 claims abstract 3
- RZNCEUXNUQNTPV-UHFFFAOYSA-N 1-[2-(4-fluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(F)C=C1 RZNCEUXNUQNTPV-UHFFFAOYSA-N 0.000 claims abstract 3
- BDSQMHIJHDEOFM-UHFFFAOYSA-N 1-[2-(4-methoxyphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1=CC(OC)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 BDSQMHIJHDEOFM-UHFFFAOYSA-N 0.000 claims abstract 3
- CMHDSZDUWCVBJT-UHFFFAOYSA-N 1-[2-(4-tert-butylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 CMHDSZDUWCVBJT-UHFFFAOYSA-N 0.000 claims abstract 3
- IEBQGRSIRNQFML-UHFFFAOYSA-N 4-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)benzonitrile Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C#N)C=C1 IEBQGRSIRNQFML-UHFFFAOYSA-N 0.000 claims abstract 3
- CKNNROUSCNBFEJ-GFCCVEGCSA-N (3r)-1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 CKNNROUSCNBFEJ-GFCCVEGCSA-N 0.000 claims abstract 2
- LKBCNWICZKAVSA-GFCCVEGCSA-N (3r)-1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonylpyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 LKBCNWICZKAVSA-GFCCVEGCSA-N 0.000 claims abstract 2
- NPBSEZPEUWIASN-QGZVFWFLSA-N (3r)-1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-n,n-dimethylpyrrolidin-3-amine Chemical compound C1[C@H](N(C)C)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 NPBSEZPEUWIASN-QGZVFWFLSA-N 0.000 claims abstract 2
- CKNNROUSCNBFEJ-LBPRGKRZSA-N (3s)-1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 CKNNROUSCNBFEJ-LBPRGKRZSA-N 0.000 claims abstract 2
- LKBCNWICZKAVSA-LBPRGKRZSA-N (3s)-1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonylpyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 LKBCNWICZKAVSA-LBPRGKRZSA-N 0.000 claims abstract 2
- CNZUBHUTQIKZHA-UHFFFAOYSA-N 1-(2-naphthalen-1-yloxy-5-nitrophenyl)sulfonylpiperazine Chemical compound C=1C([N+](=O)[O-])=CC=C(OC=2C3=CC=CC=C3C=CC=2)C=1S(=O)(=O)N1CCNCC1 CNZUBHUTQIKZHA-UHFFFAOYSA-N 0.000 claims abstract 2
- QEWRIHFOISRYEU-UHFFFAOYSA-N 1-(5-nitro-2-phenylsulfanylphenyl)sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC=CC=C1 QEWRIHFOISRYEU-UHFFFAOYSA-N 0.000 claims abstract 2
- VMUQFIROONPNBN-UHFFFAOYSA-N 1-[2-(2,3-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC(Cl)=C1Cl VMUQFIROONPNBN-UHFFFAOYSA-N 0.000 claims abstract 2
- SRDGCSOZRUAHBF-UHFFFAOYSA-N 1-[2-(2,3-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1C SRDGCSOZRUAHBF-UHFFFAOYSA-N 0.000 claims abstract 2
- VRFKGWJBBLGBDV-UHFFFAOYSA-N 1-[2-(2,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC=C1Cl VRFKGWJBBLGBDV-UHFFFAOYSA-N 0.000 claims abstract 2
- TWHCYUFWYQPECU-UHFFFAOYSA-N 1-[2-(2,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=C(C)C(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 TWHCYUFWYQPECU-UHFFFAOYSA-N 0.000 claims abstract 2
- PJYXKAFVZJWLEL-UHFFFAOYSA-N 1-[2-(2-butylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CCCCC1=CC=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 PJYXKAFVZJWLEL-UHFFFAOYSA-N 0.000 claims abstract 2
- PTUMOLDUYIHIMN-UHFFFAOYSA-N 1-[2-(2-chloro-5-methylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=C(Cl)C(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 PTUMOLDUYIHIMN-UHFFFAOYSA-N 0.000 claims abstract 2
- PRFONUVBMWZEOO-UHFFFAOYSA-N 1-[2-(2-chlorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1Cl PRFONUVBMWZEOO-UHFFFAOYSA-N 0.000 claims abstract 2
- YQUNOFICCSRABU-UHFFFAOYSA-N 1-[2-(2-fluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1F YQUNOFICCSRABU-UHFFFAOYSA-N 0.000 claims abstract 2
- NPPTVQFQSMCLII-UHFFFAOYSA-N 1-[2-(2-methoxyphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound COC1=CC=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 NPPTVQFQSMCLII-UHFFFAOYSA-N 0.000 claims abstract 2
- BSQWJBXLDGJJHM-UHFFFAOYSA-N 1-[2-(2-methylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 BSQWJBXLDGJJHM-UHFFFAOYSA-N 0.000 claims abstract 2
- KLBIHTVPUMBOAX-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C(Cl)=C1 KLBIHTVPUMBOAX-UHFFFAOYSA-N 0.000 claims abstract 2
- FOONKUUEERTDAY-UHFFFAOYSA-N 1-[2-(3,4-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 FOONKUUEERTDAY-UHFFFAOYSA-N 0.000 claims abstract 2
- QFTHARQHPRIFKO-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-4-methoxy-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C=1C=C([N+]([O-])=O)C(OC)=CC=1OC1=CC(Cl)=CC(Cl)=C1 QFTHARQHPRIFKO-UHFFFAOYSA-N 0.000 claims abstract 2
- SOLLLMCPZGPXGZ-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-4-methyl-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C=1C=C([N+]([O-])=O)C(C)=CC=1OC1=CC(Cl)=CC(Cl)=C1 SOLLLMCPZGPXGZ-UHFFFAOYSA-N 0.000 claims abstract 2
- CZRCXBTVUGRSSR-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-fluorophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC(F)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 CZRCXBTVUGRSSR-UHFFFAOYSA-N 0.000 claims abstract 2
- ALCAJDBOHMKLRA-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-(oxolan-2-ylmethyl)piperazine Chemical compound C1CN(CC2OCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 ALCAJDBOHMKLRA-UHFFFAOYSA-N 0.000 claims abstract 2
- WHQTYQUIELPVEY-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-piperidin-1-ylpiperidine Chemical compound C1CC(N2CCCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 WHQTYQUIELPVEY-UHFFFAOYSA-N 0.000 claims abstract 2
- GIPMTPNQXFCWSK-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-6-fluorophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C=1C(F)=CC=CC=1OC1=CC(Cl)=CC(Cl)=C1 GIPMTPNQXFCWSK-UHFFFAOYSA-N 0.000 claims abstract 2
- IYVUIAWOBJQUDX-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonyl-4-(oxolan-2-ylmethyl)piperazine Chemical compound C1CN(CC2OCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC(Cl)=CC(Cl)=C1 IYVUIAWOBJQUDX-UHFFFAOYSA-N 0.000 claims abstract 2
- FETOGFFHJPLNPD-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonyl-4-piperidin-1-ylpiperidine Chemical compound C1CC(N2CCCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC(Cl)=CC(Cl)=C1 FETOGFFHJPLNPD-UHFFFAOYSA-N 0.000 claims abstract 2
- VXIAQMBSGJGWKX-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC(Cl)=CC(Cl)=C1 VXIAQMBSGJGWKX-UHFFFAOYSA-N 0.000 claims abstract 2
- TZHBVJQROPVXGQ-UHFFFAOYSA-N 1-[2-(3,5-difluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(F)=CC(F)=C1 TZHBVJQROPVXGQ-UHFFFAOYSA-N 0.000 claims abstract 2
- QKNIALROEBGESQ-UHFFFAOYSA-N 1-[2-(3,5-dimethoxyphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound COC1=CC(OC)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 QKNIALROEBGESQ-UHFFFAOYSA-N 0.000 claims abstract 2
- KMXIMLHBSQZKJV-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-4-(trifluoromethyl)phenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC=C(C=2)C(F)(F)F)S(=O)(=O)N2CCNCC2)=C1 KMXIMLHBSQZKJV-UHFFFAOYSA-N 0.000 claims abstract 2
- FMXGRMIOZCXYKI-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-4-methoxy-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C=1C=C([N+]([O-])=O)C(OC)=CC=1OC1=CC(C)=CC(C)=C1 FMXGRMIOZCXYKI-UHFFFAOYSA-N 0.000 claims abstract 2
- MXSMLSHFSZKWSX-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-4-methoxyphenyl]sulfonylpiperazine Chemical compound C=1C(OC)=CC=C(S(=O)(=O)N2CCNCC2)C=1OC1=CC(C)=CC(C)=C1 MXSMLSHFSZKWSX-UHFFFAOYSA-N 0.000 claims abstract 2
- BJXRKPYXMZQXAR-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-4-methyl-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=C(C)C=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 BJXRKPYXMZQXAR-UHFFFAOYSA-N 0.000 claims abstract 2
- ABTDJJDQUZCAOX-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-4-methylphenyl]sulfonylpiperazine Chemical compound C=1C(C)=CC=C(S(=O)(=O)N2CCNCC2)C=1OC1=CC(C)=CC(C)=C1 ABTDJJDQUZCAOX-UHFFFAOYSA-N 0.000 claims abstract 2
- FGQDSOITWFJLNJ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-(trifluoromethyl)phenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)S(=O)(=O)N2CCNCC2)=C1 FGQDSOITWFJLNJ-UHFFFAOYSA-N 0.000 claims abstract 2
- DHCQACPKRSVPGK-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-methylsulfonylphenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)S(C)(=O)=O)S(=O)(=O)N2CCNCC2)=C1 DHCQACPKRSVPGK-UHFFFAOYSA-N 0.000 claims abstract 2
- ITSISERJUCKGHH-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 ITSISERJUCKGHH-UHFFFAOYSA-N 0.000 claims abstract 2
- UQBGBZMCKZTKOI-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 UQBGBZMCKZTKOI-UHFFFAOYSA-N 0.000 claims abstract 2
- KCHWUWYUKUHJKQ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1N1CCN(S(=O)(=O)C=2C(=CC=C(C=2)[N+]([O-])=O)OC=2C=C(C)C=C(C)C=2)CC1 KCHWUWYUKUHJKQ-UHFFFAOYSA-N 0.000 claims abstract 2
- QMYALZOMMNFABZ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-methylpiperazine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 QMYALZOMMNFABZ-UHFFFAOYSA-N 0.000 claims abstract 2
- XJBSXCYXPSTJSU-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-pentan-2-ylpiperazine Chemical compound C1CN(C(C)CCC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 XJBSXCYXPSTJSU-UHFFFAOYSA-N 0.000 claims abstract 2
- ZSWHTLUHZIPYEH-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-phenylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C=2C=CC=CC=2)=C1 ZSWHTLUHZIPYEH-UHFFFAOYSA-N 0.000 claims abstract 2
- MDTYMAXBFDJZKX-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-pyrrolidin-1-ylpiperidine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCC(CC2)N2CCCC2)=C1 MDTYMAXBFDJZKX-UHFFFAOYSA-N 0.000 claims abstract 2
- GEMWHFJXKKFPOV-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-n,n-dimethylpiperidin-4-amine Chemical compound C1CC(N(C)C)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 GEMWHFJXKKFPOV-UHFFFAOYSA-N 0.000 claims abstract 2
- OMDDVRZQAPTBJY-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-6-fluorophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=C(F)C=CC=2)S(=O)(=O)N2CCNCC2)=C1 OMDDVRZQAPTBJY-UHFFFAOYSA-N 0.000 claims abstract 2
- PCTXLUNXHGFXSZ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)phenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC=CC=2)S(=O)(=O)N2CCNCC2)=C1 PCTXLUNXHGFXSZ-UHFFFAOYSA-N 0.000 claims abstract 2
- JXMAZUWELXXPKK-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenyl)sulfanyl-5-nitrophenyl]sulfonyl-4-(oxolan-2-ylmethyl)piperazine Chemical compound CC1=CC(C)=CC(SC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC3OCCC3)CC2)=C1 JXMAZUWELXXPKK-UHFFFAOYSA-N 0.000 claims abstract 2
- HUKQTLDAPAMDNQ-UHFFFAOYSA-N 1-[2-(3,5-ditert-butylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 HUKQTLDAPAMDNQ-UHFFFAOYSA-N 0.000 claims abstract 2
- IBJWVCBNRCDYIG-UHFFFAOYSA-N 1-[2-(3-bromophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC(Br)=C1 IBJWVCBNRCDYIG-UHFFFAOYSA-N 0.000 claims abstract 2
- BVMUXEFUDWKPGS-UHFFFAOYSA-N 1-[2-(3-chloro-4-fluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(F)C(Cl)=C1 BVMUXEFUDWKPGS-UHFFFAOYSA-N 0.000 claims abstract 2
- JKQULDIMXSXQCM-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)sulfanyl-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC=CC(Cl)=C1 JKQULDIMXSXQCM-UHFFFAOYSA-N 0.000 claims abstract 2
- FCDPOBWGQBJFKV-UHFFFAOYSA-N 1-[2-(3-fluorophenyl)sulfanyl-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC=CC(F)=C1 FCDPOBWGQBJFKV-UHFFFAOYSA-N 0.000 claims abstract 2
- NZDLWKOJSRYHFA-UHFFFAOYSA-N 1-[2-(3-methoxy-5-methylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound COC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 NZDLWKOJSRYHFA-UHFFFAOYSA-N 0.000 claims abstract 2
- IIZWKTPGUGWWCY-UHFFFAOYSA-N 1-[2-(3-methyl-5-propan-2-ylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC(C)C1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 IIZWKTPGUGWWCY-UHFFFAOYSA-N 0.000 claims abstract 2
- OOMHCLMAQUGRLL-UHFFFAOYSA-N 1-[2-(3-methylphenyl)sulfanyl-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=CC(SC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 OOMHCLMAQUGRLL-UHFFFAOYSA-N 0.000 claims abstract 2
- WYCPWWYEDXNJJB-UHFFFAOYSA-N 1-[2-(3-tert-butylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC(C)(C)C1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 WYCPWWYEDXNJJB-UHFFFAOYSA-N 0.000 claims abstract 2
- GMBZFUZJPDBRAN-UHFFFAOYSA-N 1-[2-(4-chloro-3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=C(Cl)C(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 GMBZFUZJPDBRAN-UHFFFAOYSA-N 0.000 claims abstract 2
- FACLWBLFTHHVDG-UHFFFAOYSA-N 1-[2-(4-chloro-3-methylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1=C(Cl)C(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 FACLWBLFTHHVDG-UHFFFAOYSA-N 0.000 claims abstract 2
- JSNCXWYNYFBJKN-UHFFFAOYSA-N 1-[2-(4-chloro-5-methyl-2-propan-2-ylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC(C)C1=CC(Cl)=C(C)C=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 JSNCXWYNYFBJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- VBMZZDPPTHYHIO-UHFFFAOYSA-N 1-[2-(4-methylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1=CC(C)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 VBMZZDPPTHYHIO-UHFFFAOYSA-N 0.000 claims abstract 2
- NEDJANFVNXLVSW-UHFFFAOYSA-N 1-[2-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 NEDJANFVNXLVSW-UHFFFAOYSA-N 0.000 claims abstract 2
- XTXWURBRDIOANV-UHFFFAOYSA-N 1-[2-(5-methyl-2-nitrophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=C([N+]([O-])=O)C(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 XTXWURBRDIOANV-UHFFFAOYSA-N 0.000 claims abstract 2
- ZAUDJXSEGGMDCB-UHFFFAOYSA-N 1-[2-(5-methyl-2-propan-2-ylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC(C)C1=CC=C(C)C=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 ZAUDJXSEGGMDCB-UHFFFAOYSA-N 0.000 claims abstract 2
- IVUFHOXLGXBOLL-UHFFFAOYSA-N 1-[2-(6-methylpyridin-3-yl)oxy-5-nitrophenyl]sulfonylpiperazine Chemical compound C1=NC(C)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 IVUFHOXLGXBOLL-UHFFFAOYSA-N 0.000 claims abstract 2
- HTWUEPGGNCNQTD-UHFFFAOYSA-N 1-[2-[3,5-bis(trifluoromethyl)phenoxy]-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HTWUEPGGNCNQTD-UHFFFAOYSA-N 0.000 claims abstract 2
- VNTRJQZGFBUIHO-UHFFFAOYSA-N 1-[2-[3,5-bis(trifluoromethyl)phenyl]sulfanyl-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VNTRJQZGFBUIHO-UHFFFAOYSA-N 0.000 claims abstract 2
- YTDLVNFZOLDGAE-UHFFFAOYSA-N 1-[3-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 YTDLVNFZOLDGAE-UHFFFAOYSA-N 0.000 claims abstract 2
- BUZJSEYCTRQHRX-UHFFFAOYSA-N 1-[4-(3,5-dimethylphenoxy)-3-piperazin-1-ylsulfonylphenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)S(=O)(=O)N2CCNCC2)S(=O)(=O)N2CCNCC2)=C1 BUZJSEYCTRQHRX-UHFFFAOYSA-N 0.000 claims abstract 2
- SPLFTRDCGYWULR-UHFFFAOYSA-N 1-[5-bromo-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperazine Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(Br)=CC=2)S(=O)(=O)N2CCNCC2)=C1 SPLFTRDCGYWULR-UHFFFAOYSA-N 0.000 claims abstract 2
- XSYADPLEDXOBLS-UHFFFAOYSA-N 1-[5-chloro-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 XSYADPLEDXOBLS-UHFFFAOYSA-N 0.000 claims abstract 2
- FKMLKTTXVWBDCI-UHFFFAOYSA-N 1-[5-nitro-2-(2,3,4,5,6-pentafluorophenoxy)phenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=C(F)C(F)=C(F)C(F)=C1F FKMLKTTXVWBDCI-UHFFFAOYSA-N 0.000 claims abstract 2
- COABWAUZOZFVPX-UHFFFAOYSA-N 1-[5-nitro-2-(2,3,5,6-tetrafluorophenoxy)phenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=C(F)C(F)=CC(F)=C1F COABWAUZOZFVPX-UHFFFAOYSA-N 0.000 claims abstract 2
- XOVUZQVAZHPFQZ-UHFFFAOYSA-N 1-[5-nitro-2-(2,3,5-trichlorophenoxy)phenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1Cl XOVUZQVAZHPFQZ-UHFFFAOYSA-N 0.000 claims abstract 2
- GFHVPDVDJDKUPC-UHFFFAOYSA-N 1-[5-nitro-2-(2,3,5-trimethylphenoxy)phenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=C(C)C(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 GFHVPDVDJDKUPC-UHFFFAOYSA-N 0.000 claims abstract 2
- IMOIUAGMIMJEKC-UHFFFAOYSA-N 1-[5-nitro-2-(2,3,6-trimethylphenoxy)phenyl]sulfonylpiperazine Chemical compound CC1=CC=C(C)C(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1C IMOIUAGMIMJEKC-UHFFFAOYSA-N 0.000 claims abstract 2
- LEACPKDICKVJHD-UHFFFAOYSA-N 1-[5-nitro-2-(2,4,6-trimethylphenyl)sulfanylphenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(C)=C1SC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 LEACPKDICKVJHD-UHFFFAOYSA-N 0.000 claims abstract 2
- RFLIUUDKADZDEK-UHFFFAOYSA-N 1-[5-nitro-2-(3,4,5-trimethylphenoxy)phenyl]sulfonylpiperazine Chemical compound CC1=C(C)C(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 RFLIUUDKADZDEK-UHFFFAOYSA-N 0.000 claims abstract 2
- MGWJNHYVOGHAEV-UHFFFAOYSA-N 1-[5-nitro-2-(3-nitrophenoxy)phenyl]sulfonylpiperazine Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 MGWJNHYVOGHAEV-UHFFFAOYSA-N 0.000 claims abstract 2
- PPNLETXCBSYWGK-UHFFFAOYSA-N 1-[5-nitro-2-(3-phenylphenoxy)phenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC(C=1)=CC=CC=1C1=CC=CC=C1 PPNLETXCBSYWGK-UHFFFAOYSA-N 0.000 claims abstract 2
- BTSNQMATZRNHGK-UHFFFAOYSA-N 1-[5-nitro-2-(3-propan-2-ylphenoxy)phenyl]sulfonylpiperazine Chemical compound CC(C)C1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 BTSNQMATZRNHGK-UHFFFAOYSA-N 0.000 claims abstract 2
- FTTFWMTZVHUOKO-UHFFFAOYSA-N 1-[5-nitro-2-(5,6,7,8-tetrahydronaphthalen-2-yloxy)phenyl]sulfonylpiperazine Chemical compound C=1C([N+](=O)[O-])=CC=C(OC=2C=C3CCCCC3=CC=2)C=1S(=O)(=O)N1CCNCC1 FTTFWMTZVHUOKO-UHFFFAOYSA-N 0.000 claims abstract 2
- JOPQMEWEDXEUND-UHFFFAOYSA-N 1-[5-nitro-2-[3-(trifluoromethyl)phenoxy]phenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC(C(F)(F)F)=C1 JOPQMEWEDXEUND-UHFFFAOYSA-N 0.000 claims abstract 2
- IYXDPORZMMDPEP-UHFFFAOYSA-N 1-benzyl-4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC=3C=CC=CC=3)CC2)=C1 IYXDPORZMMDPEP-UHFFFAOYSA-N 0.000 claims abstract 2
- FRPCZMWUQATYMI-UHFFFAOYSA-N 1-butan-2-yl-4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CN(C(C)CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 FRPCZMWUQATYMI-UHFFFAOYSA-N 0.000 claims abstract 2
- QUKOYWSWDYFCSC-UHFFFAOYSA-N 1-cyclohexyl-4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C2CCCCC2)=C1 QUKOYWSWDYFCSC-UHFFFAOYSA-N 0.000 claims abstract 2
- QDTBQDTWWCZTBB-UHFFFAOYSA-N 1-cyclopentyl-4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C2CCCC2)=C1 QDTBQDTWWCZTBB-UHFFFAOYSA-N 0.000 claims abstract 2
- OCXMBTYICVRURC-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)-5-nitro-n-(piperidin-4-ylmethyl)benzenesulfonamide Chemical compound C1CNCCC1CNS(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 OCXMBTYICVRURC-UHFFFAOYSA-N 0.000 claims abstract 2
- UGOXQWJFXKALGA-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)-n-[2-(dimethylamino)ethyl]-n-methyl-5-nitrobenzenesulfonamide Chemical compound CN(C)CCN(C)S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 UGOXQWJFXKALGA-UHFFFAOYSA-N 0.000 claims abstract 2
- VEJNVLBWDWOYLN-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)-n-[4-(dimethylamino)phenyl]-5-nitrobenzenesulfonamide Chemical compound C1=CC(N(C)C)=CC=C1NS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 VEJNVLBWDWOYLN-UHFFFAOYSA-N 0.000 claims abstract 2
- RVHKZHUSOPGABQ-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)-n-methyl-n-(1-methylpyrrolidin-3-yl)-5-nitrobenzenesulfonamide Chemical compound C=1C([N+]([O-])=O)=CC=C(OC=2C=C(Cl)C=C(Cl)C=2)C=1S(=O)(=O)N(C)C1CCN(C)C1 RVHKZHUSOPGABQ-UHFFFAOYSA-N 0.000 claims abstract 2
- VACBMTMVODEGPX-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)sulfanyl-n-[2-(dimethylamino)ethyl]-n-methyl-5-nitrobenzenesulfonamide Chemical compound CN(C)CCN(C)S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 VACBMTMVODEGPX-UHFFFAOYSA-N 0.000 claims abstract 2
- PMANOQBHISLGIF-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)sulfanyl-n-[3-(2-methylpiperidin-1-yl)propyl]-5-nitrobenzenesulfonamide Chemical compound CC1CCCCN1CCCNS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 PMANOQBHISLGIF-UHFFFAOYSA-N 0.000 claims abstract 2
- AQZJWRDPHOSBMK-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)sulfanyl-n-[3-(dimethylamino)-2,2-dimethylpropyl]-5-nitrobenzenesulfonamide Chemical compound CN(C)CC(C)(C)CNS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 AQZJWRDPHOSBMK-UHFFFAOYSA-N 0.000 claims abstract 2
- KEEPBYLEMQMSGR-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)-n-(2-morpholin-4-ylethyl)-5-nitrobenzenesulfonamide Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)NCCN2CCOCC2)=C1 KEEPBYLEMQMSGR-UHFFFAOYSA-N 0.000 claims abstract 2
- LLCZSSMCFWZIEI-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)-n-ethyl-n-(1-ethylpyrrolidin-3-yl)-5-nitrobenzenesulfonamide Chemical compound C=1C([N+]([O-])=O)=CC=C(OC=2C=C(C)C=C(C)C=2)C=1S(=O)(=O)N(CC)C1CCN(CC)C1 LLCZSSMCFWZIEI-UHFFFAOYSA-N 0.000 claims abstract 2
- JJPPJHZRAIYWQA-UHFFFAOYSA-N 2-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)benzonitrile Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1C#N JJPPJHZRAIYWQA-UHFFFAOYSA-N 0.000 claims abstract 2
- DWISRHBEIZHXKF-UHFFFAOYSA-N 2-[2-[4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazin-1-yl]ethoxy]ethanol Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CCOCCO)CC2)=C1 DWISRHBEIZHXKF-UHFFFAOYSA-N 0.000 claims abstract 2
- BXBXBZDVLVEBBP-UHFFFAOYSA-N 2-[4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazin-1-yl]ethanol Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CCO)CC2)=C1 BXBXBZDVLVEBBP-UHFFFAOYSA-N 0.000 claims abstract 2
- GCEFLNBUUJQNEX-UHFFFAOYSA-N 3-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)aniline Chemical compound NC1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 GCEFLNBUUJQNEX-UHFFFAOYSA-N 0.000 claims abstract 2
- DVRLDYONFNNECN-UHFFFAOYSA-N 3-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)benzonitrile Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC(C#N)=C1 DVRLDYONFNNECN-UHFFFAOYSA-N 0.000 claims abstract 2
- CXTUSMAEFUYVJW-UHFFFAOYSA-N 3-[1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperidin-4-yl]propanoic acid Chemical compound C1CC(CCC(=O)O)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 CXTUSMAEFUYVJW-UHFFFAOYSA-N 0.000 claims abstract 2
- WBPMUUVQFICLSA-UHFFFAOYSA-N 3-methyl-5-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)phenol Chemical compound CC1=CC(O)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 WBPMUUVQFICLSA-UHFFFAOYSA-N 0.000 claims abstract 2
- WLMHDIJVIIVWEF-UHFFFAOYSA-N 4-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 WLMHDIJVIIVWEF-UHFFFAOYSA-N 0.000 claims abstract 2
- YGXPZAIFIGOFMB-UHFFFAOYSA-N 4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine-1-carbaldehyde Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C=O)=C1 YGXPZAIFIGOFMB-UHFFFAOYSA-N 0.000 claims abstract 2
- WVCULIJEYOZHMM-UHFFFAOYSA-N 6-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1C2CCCNC2CN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 WVCULIJEYOZHMM-UHFFFAOYSA-N 0.000 claims abstract 2
- TYYFCNUYDYVVPS-UHFFFAOYSA-N [1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperidin-4-yl]methanamine Chemical compound C1CC(CN)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 TYYFCNUYDYVVPS-UHFFFAOYSA-N 0.000 claims abstract 2
- KWSROXFQMFYGOA-UHFFFAOYSA-N [1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonylpiperidin-4-yl]methanamine Chemical compound C1CC(CN)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 KWSROXFQMFYGOA-UHFFFAOYSA-N 0.000 claims abstract 2
- ZVTHRBJSBOQXOS-UHFFFAOYSA-N [4-(3,5-dimethylphenoxy)-3-piperazin-1-ylsulfonylphenyl]-piperazin-1-ylmethanone Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)C(=O)N2CCNCC2)S(=O)(=O)N2CCNCC2)=C1 ZVTHRBJSBOQXOS-UHFFFAOYSA-N 0.000 claims abstract 2
- ACZWOKOPJJWMFQ-UHFFFAOYSA-N n,n-dimethyl-3-(4-nitro-2-piperazin-1-ylsulfonylphenoxy)aniline Chemical compound CN(C)C1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 ACZWOKOPJJWMFQ-UHFFFAOYSA-N 0.000 claims abstract 2
- WGBYSMKAAPXDPE-UHFFFAOYSA-N n-(2-aminoethyl)-2-(3,5-dichlorophenoxy)-5-nitrobenzenesulfonamide Chemical compound NCCNS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 WGBYSMKAAPXDPE-UHFFFAOYSA-N 0.000 claims abstract 2
- UUEFFEASXGASRN-UHFFFAOYSA-N n-(2-aminoethyl)-2-(3,5-dichlorophenyl)sulfanyl-5-nitrobenzenesulfonamide Chemical compound NCCNS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 UUEFFEASXGASRN-UHFFFAOYSA-N 0.000 claims abstract 2
- OEHNADMNPIYEHJ-UHFFFAOYSA-N n-(2-chlorophenyl)-4-nitro-2-piperazin-1-ylsulfonylaniline Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1Cl OEHNADMNPIYEHJ-UHFFFAOYSA-N 0.000 claims abstract 2
- RCSXCAVUJIRVJH-UHFFFAOYSA-N n-(2-fluorophenyl)-4-nitro-2-piperazin-1-ylsulfonylaniline Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1F RCSXCAVUJIRVJH-UHFFFAOYSA-N 0.000 claims abstract 2
- ICEXYMUGMWTPTH-UHFFFAOYSA-N n-(2-methoxyphenyl)-4-nitro-2-piperazin-1-ylsulfonylaniline Chemical compound COC1=CC=CC=C1NC1=CC=C([N+]([O-])=O)C=C1S(=O)(=O)N1CCNCC1 ICEXYMUGMWTPTH-UHFFFAOYSA-N 0.000 claims abstract 2
- PXBYTXIHGBMUBO-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-4-nitro-2-piperazin-1-ylsulfonylaniline Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1NC1=CC(Cl)=CC(Cl)=C1 PXBYTXIHGBMUBO-UHFFFAOYSA-N 0.000 claims abstract 2
- QBCYEMMYYYBOQG-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-4-nitro-2-piperazin-1-ylsulfonylaniline Chemical compound CC1=CC(C)=CC(NC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 QBCYEMMYYYBOQG-UHFFFAOYSA-N 0.000 claims abstract 2
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- IXBWTTXRCGKKEH-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-4-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC=C(C=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 IXBWTTXRCGKKEH-UHFFFAOYSA-N 0.000 description 1
- OQLBYUIGUZLKLN-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-5-(2h-tetrazol-5-yl)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)C=2NN=NN=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 OQLBYUIGUZLKLN-UHFFFAOYSA-N 0.000 description 1
- WEKBRBQLFGPBQL-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenyl)sulfanyl-5-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(SC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 WEKBRBQLFGPBQL-UHFFFAOYSA-N 0.000 description 1
- IIMOSRGMGDCVBD-UHFFFAOYSA-N tert-butyl 4-[3-(3,5-dimethylphenoxy)-4-methyl-5-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=C(C=C(C=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)[N+]([O-])=O)C)=C1 IIMOSRGMGDCVBD-UHFFFAOYSA-N 0.000 description 1
- WWXYAYIAGKTTIJ-UHFFFAOYSA-N tert-butyl 4-[5-[1-(2-cyanoethyl)tetrazol-5-yl]-2-(3,5-dimethylphenoxy)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)C=2N(N=NN=2)CCC#N)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 WWXYAYIAGKTTIJ-UHFFFAOYSA-N 0.000 description 1
- SGQKNUSSFCVPID-UHFFFAOYSA-N tert-butyl 4-[5-chloro-2-(3,5-dimethylphenoxy)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(Cl)=CC=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 SGQKNUSSFCVPID-UHFFFAOYSA-N 0.000 description 1
- HXKOCZAITVMTQI-UHFFFAOYSA-N tert-butyl 4-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonyl-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 HXKOCZAITVMTQI-UHFFFAOYSA-N 0.000 description 1
- JCHLAGJGTDAYEK-UHFFFAOYSA-N tert-butyl 4-[5-cyano-2-(3,5-dichlorophenyl)sulfinylphenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1S(=O)C1=CC(Cl)=CC(Cl)=C1 JCHLAGJGTDAYEK-UHFFFAOYSA-N 0.000 description 1
- JECGTFYIDZAKOE-UHFFFAOYSA-N tert-butyl 4-[[5-(3,5-dimethylphenoxy)-1h-indol-6-yl]sulfonyl]piperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC=3NC=CC=3C=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 JECGTFYIDZAKOE-UHFFFAOYSA-N 0.000 description 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 1
- AZAKMLHUDVIDFN-UHFFFAOYSA-N tert-butyl nitrate Chemical compound CC(C)(C)O[N+]([O-])=O AZAKMLHUDVIDFN-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical class [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
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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
- C07D207/02—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
- 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
- C07D207/10—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 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 ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
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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
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 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 ring carbon atoms
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- C07D211/58—Nitrogen atoms attached in position 4
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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| SE0203754D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
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| MXPA05010055A (es) * | 2003-03-24 | 2005-11-23 | Actimis Pharmaceuticals Inc | Derivados de 2-fenoxi- y 2-fenil-sulfomamida con actividad antagonista del ccr3, para el tratamiento del asma y otros desordenes inflamatorios o inmunologicos. |
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| TW200630337A (en) | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| JP2009501793A (ja) | 2005-07-21 | 2009-01-22 | アストラゼネカ・アクチエボラーグ | 新規ピペリジン誘導体 |
| US8247442B2 (en) | 2006-03-29 | 2012-08-21 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use |
| WO2007118854A1 (en) | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and the use thereof |
| US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| BRPI0710512A2 (pt) | 2006-04-20 | 2012-06-05 | Hoffmann La Roche | moduladores derivados de diazepan de receptores de quimiocinas |
| US8399486B2 (en) | 2007-04-09 | 2013-03-19 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use thereof |
| US7897776B2 (en) | 2007-04-23 | 2011-03-01 | Salutria Pharmaceuticals Llc | Sulfonamide containing compounds for treatment of inflammatory disorders |
| WO2009040659A2 (en) | 2007-09-28 | 2009-04-02 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| NZ593473A (en) * | 2009-01-12 | 2013-02-22 | Pfizer Ltd | Sulfonamide derivatives |
| TW201036941A (en) * | 2009-03-30 | 2010-10-16 | Sumitomo Chemical Co | Method for producing sulfonamide compound |
| CN102448951B (zh) | 2009-04-06 | 2017-05-10 | 安吉奥斯医药品有限公司 | 丙酮酸激酶m2调节剂、治疗组合物和相关使用方法 |
| MX2011011139A (es) * | 2009-04-22 | 2012-01-27 | Axikin Pharmaceuticals Inc | Antagonistas ccr3 arisulfonamida 2, 5-disustituidos. |
| PE20120811A1 (es) * | 2009-04-22 | 2012-07-08 | Axikin Pharmaceuticals Inc | Antagonistas ccr3 arilsulfonamida |
| AU2010239340B2 (en) | 2009-04-22 | 2015-07-02 | Axikin Pharmaceuticals, Inc. | 2,5-disubstituted arylsulfonamide CCR3 antagonists |
| WO2010129351A1 (en) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Method to identify and treat age-related macular degeneration |
| NZ597379A (en) | 2009-06-29 | 2014-04-30 | Agios Pharmaceuticals Inc | Therapeutic compounds and compositions |
| EP2448581B1 (en) * | 2009-06-29 | 2016-12-07 | Agios Pharmaceuticals, Inc. | Therapeutic compositions and related methods of use |
| AU2011223873B2 (en) * | 2010-03-02 | 2015-06-25 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide CCR3 antagonists |
| EP2547655B1 (en) * | 2010-03-17 | 2016-03-09 | Axikin Pharmaceuticals, Inc. | Arylsulfonamide ccr3 antagonists |
| CA2803118C (en) | 2010-07-09 | 2015-11-03 | Pfizer Limited | Sulfonamide derivatives as nav 1.7 inhibitors |
| JP5872552B2 (ja) | 2010-07-09 | 2016-03-01 | ファイザー・リミテッドPfizer Limited | 化学化合物 |
| CA2814011A1 (en) * | 2010-10-11 | 2012-04-19 | Axikin Pharmaceuticals, Inc. | Salts of arylsulfonamide ccr3 antagonists |
| EP2651898B1 (en) | 2010-12-17 | 2015-12-09 | Agios Pharmaceuticals, Inc. | Novel n-(4-(azetidine-1-carbonyl)phenyl)-(hetero-)arylsulfonamide derivatives as pyruvate kinase m2 (pmk2) modulators |
| CA2822432C (en) | 2010-12-21 | 2019-09-24 | Agios Pharmaceuticals, Inc. | Bicyclic pkm2 activators |
| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| PH12017501176B1 (en) | 2011-05-03 | 2023-03-08 | Agios Pharmaceuticals Inc | Pyruvate kinase activators for use in therapy |
| US9181231B2 (en) | 2011-05-03 | 2015-11-10 | Agios Pharmaceuticals, Inc | Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia |
| AU2013312420A1 (en) | 2012-09-07 | 2015-02-26 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide CCR3 antagonists |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| SI3307271T1 (sl) | 2015-06-11 | 2023-11-30 | Agios Pharmaceuticals, Inc. | Postopki za uporabo aktivatorjev piruvat kinaze |
| US12221463B2 (en) | 2020-08-07 | 2025-02-11 | The Board Of Regents Of The University Of Oklahoma | Method of promoting wound healing by inhibiting CCR3 |
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| US6432981B1 (en) | 1999-06-11 | 2002-08-13 | Merck & Co., Inc. | Cyclopentyl modulators of chemokine receptor activity |
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- 2002-09-04 CA CA002459432A patent/CA2459432C/en not_active Expired - Fee Related
- 2002-09-04 WO PCT/EP2002/009873 patent/WO2003022277A1/en not_active Ceased
- 2002-09-04 ES ES07013793T patent/ES2354378T3/es not_active Expired - Lifetime
- 2002-09-04 DE DE60238149T patent/DE60238149D1/de not_active Expired - Lifetime
- 2002-09-04 ES ES02772265T patent/ES2294167T3/es not_active Expired - Lifetime
- 2002-09-05 TW TW091120389A patent/TWI262187B/zh not_active IP Right Cessation
- 2002-09-05 GT GT200200178A patent/GT200200178A/es unknown
- 2002-09-06 MY MYPI20023349A patent/MY133303A/en unknown
- 2002-09-06 SV SV2002001225A patent/SV2004001225A/es not_active Application Discontinuation
- 2002-09-06 HN HN2002000247A patent/HN2002000247A/es unknown
- 2002-09-06 PE PE2002000882A patent/PE20030440A1/es not_active Application Discontinuation
-
2010
- 2010-04-19 US US12/763,072 patent/US8242118B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2294167T3 (es) | 2008-04-01 |
| MY133303A (en) | 2007-11-30 |
| HK1109867A1 (en) | 2008-06-27 |
| TWI262187B (en) | 2006-09-21 |
| GT200200178A (es) | 2003-05-23 |
| US8242118B2 (en) | 2012-08-14 |
| WO2003022277A1 (en) | 2003-03-20 |
| EP1461038A1 (en) | 2004-09-29 |
| JP2005519024A (ja) | 2005-06-30 |
| DE60221569D1 (de) | 2007-09-13 |
| EP1461038B9 (en) | 2009-09-23 |
| SV2004001225A (es) | 2004-02-24 |
| CA2459432A1 (en) | 2003-03-20 |
| PE20030440A1 (es) | 2003-06-26 |
| US7700586B2 (en) | 2010-04-20 |
| US20100204213A1 (en) | 2010-08-12 |
| JP4517047B2 (ja) | 2010-08-04 |
| AR037235A1 (es) | 2004-11-03 |
| US20050070582A1 (en) | 2005-03-31 |
| EP1461038B1 (en) | 2007-08-01 |
| DE60238149D1 (de) | 2010-12-09 |
| HN2002000247A (es) | 2003-11-24 |
| DE60221569T2 (de) | 2008-04-30 |
| EP1849469B1 (en) | 2010-10-27 |
| CA2459432C (en) | 2009-05-26 |
| EP1849469A1 (en) | 2007-10-31 |
| JP2003081937A (ja) | 2003-03-19 |
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