NO327008B1 - Substituerte benzimidazolforbindelser og deres anvendelse for fremstilling av medikamenter for behandling av cancer - Google Patents

Substituerte benzimidazolforbindelser og deres anvendelse for fremstilling av medikamenter for behandling av cancer Download PDF

Info

Publication number: NO327008B1
Authority: NO; Norway
Prior art keywords: ester; benzoimidazol; benzenesulfonic acid; amino; ureido
Prior art date: 2001-09-26

Application number

NO20041214A

Other languages

English (en)

Norwegian (no)

Other versions

NO20041214L (no

Inventor

Francois Clerc

Francois Hamy

Isabelle Depaty

Odile Angouillant-Boniface

Chantal Carrez

Manfred Roesner

Original Assignee

Aventis Pharma Sa

Priority date (The priority date 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 date listed.)

2001-09-26

Filing date

2004-03-23

Publication date

2009-04-06

2004-03-23 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2004-06-24 Publication of NO20041214L publication Critical patent/NO20041214L/no

2009-04-06 Publication of NO327008B1 publication Critical patent/NO327008B1/no

Links

206010028980 Neoplasm Diseases 0.000 title claims description 10
201000011510 cancer Diseases 0.000 title claims description 8
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229940079593 drug Drugs 0.000 title description 7
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YXFXMBWOTKBZDE-UHFFFAOYSA-N [2-(cyclobutylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CCC1 YXFXMBWOTKBZDE-UHFFFAOYSA-N 0.000 description 1
GFCLORKUTLQHSZ-UHFFFAOYSA-N [2-(cyclohexylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2NC=1NC(=O)NC1CCCCC1 GFCLORKUTLQHSZ-UHFFFAOYSA-N 0.000 description 1
YUZLMGPKRSRJPV-UHFFFAOYSA-N [2-(cyclohexylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CCCCC1 YUZLMGPKRSRJPV-UHFFFAOYSA-N 0.000 description 1
YDJOGUCSJKOCJV-UHFFFAOYSA-N [2-(cyclopentylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CCCC1 YDJOGUCSJKOCJV-UHFFFAOYSA-N 0.000 description 1
FFJQHPRACFEMSA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1,3-dihydroxypropan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(CO)CO)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 FFJQHPRACFEMSA-UHFFFAOYSA-N 0.000 description 1
XDWHKQHHYFHSGB-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1-hydroxypentan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(CO)CCC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 XDWHKQHHYFHSGB-UHFFFAOYSA-N 0.000 description 1
UDBZMJNUEXYSPY-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1-methoxypropan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(C)COC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 UDBZMJNUEXYSPY-UHFFFAOYSA-N 0.000 description 1
PLDMGTKGLSCYSN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1-phenoxypropan-2-ylamino)benzenesulfonate Chemical compound C=1C=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=CC=1NC(C)COC1=CC=CC=C1 PLDMGTKGLSCYSN-UHFFFAOYSA-N 0.000 description 1
VRNAWQALSVDBIS-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1h-indol-5-ylamino)benzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(NC=4C=C5C=CNC5=CC=4)=CC=3)=CC=C2NC=1NC(=O)C1CC1 VRNAWQALSVDBIS-UHFFFAOYSA-N 0.000 description 1
FJYDVJAWVPGZBN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2,6-dimethylmorpholin-4-yl)benzenesulfonate Chemical compound C1C(C)OC(C)CN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 FJYDVJAWVPGZBN-UHFFFAOYSA-N 0.000 description 1
PFJRCSJKCZGTJD-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2-pyridin-3-ylpyrrolidin-1-yl)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1CCCC1C1=CC=CN=C1 PFJRCSJKCZGTJD-UHFFFAOYSA-N 0.000 description 1
VAPSQUPVXFWSLT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrol-1-ylethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCN1C=CC=C1 VAPSQUPVXFWSLT-UHFFFAOYSA-N 0.000 description 1
QZUULHZMVYXUAW-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrolidin-1-ylethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCN1CCCC1 QZUULHZMVYXUAW-UHFFFAOYSA-N 0.000 description 1
YEBLKPKXNZLGPC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3,3-dimethylpiperidin-1-yl)benzenesulfonate Chemical compound C1C(C)(C)CCCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 YEBLKPKXNZLGPC-UHFFFAOYSA-N 0.000 description 1
ZROBQSRBKZCBQY-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-hydroxypropylamino)benzenesulfonate Chemical compound C1=CC(NCCCO)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 ZROBQSRBKZCBQY-UHFFFAOYSA-N 0.000 description 1
VYMWAUHDDMRDTN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-hydroxypyrrolidin-1-yl)benzenesulfonate Chemical compound C1C(O)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 VYMWAUHDDMRDTN-UHFFFAOYSA-N 0.000 description 1
MBLDNXCADDCXQC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-imidazol-1-ylpropylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCN1C=CN=C1 MBLDNXCADDCXQC-UHFFFAOYSA-N 0.000 description 1
WDZGXSLAMMBCCD-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-methoxypropylamino)benzenesulfonate Chemical compound C1=CC(NCCCOC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 WDZGXSLAMMBCCD-UHFFFAOYSA-N 0.000 description 1
NLUJSSCPUCKCMT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-carbamoylpiperidin-1-yl)benzenesulfonate Chemical compound C1CC(C(=O)N)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 NLUJSSCPUCKCMT-UHFFFAOYSA-N 0.000 description 1
AHINQIQMTISVIY-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-ethoxyanilino)benzenesulfonate Chemical compound C1=CC(OCC)=CC=C1NC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 AHINQIQMTISVIY-UHFFFAOYSA-N 0.000 description 1
QIVWHSUAWZALKQ-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-hydroxypiperidin-1-yl)benzenesulfonate Chemical compound C1CC(O)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 QIVWHSUAWZALKQ-UHFFFAOYSA-N 0.000 description 1
NFEQLQOSJOTIJR-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-methyl-1,4-diazepan-1-yl)benzenesulfonate Chemical compound C1CN(C)CCCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 NFEQLQOSJOTIJR-UHFFFAOYSA-N 0.000 description 1
QWQLYXRARLJHOA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-pyridin-2-ylpiperazin-1-yl)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N(CC1)CCN1C1=CC=CC=N1 QWQLYXRARLJHOA-UHFFFAOYSA-N 0.000 description 1
JGCLLRZTMZRDTO-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-pyrrolidin-1-ylbutylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCCN1CCCC1 JGCLLRZTMZRDTO-UHFFFAOYSA-N 0.000 description 1
OPKNSCUJIMHDNI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 OPKNSCUJIMHDNI-UHFFFAOYSA-N 0.000 description 1
VHJWBIRJHNLFOU-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(cyclopropylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NC1CC1 VHJWBIRJHNLFOU-UHFFFAOYSA-N 0.000 description 1
HUMKESGNAGZKOJ-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(ethylamino)benzenesulfonate Chemical compound C1=CC(NCC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 HUMKESGNAGZKOJ-UHFFFAOYSA-N 0.000 description 1
YOBXDGKEIPGGFA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(piperidin-4-ylmethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCC1CCNCC1 YOBXDGKEIPGGFA-UHFFFAOYSA-N 0.000 description 1
JDXZNWOXUYIPFE-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(propylamino)benzenesulfonate Chemical compound C1=CC(NCCC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 JDXZNWOXUYIPFE-UHFFFAOYSA-N 0.000 description 1
MYVXFGSVDLZEIT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(pyridin-2-ylmethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCC1=CC=CC=N1 MYVXFGSVDLZEIT-UHFFFAOYSA-N 0.000 description 1
FCESKQRBABHKAQ-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(1-hydroxy-2-methylpropan-2-yl)amino]benzenesulfonate Chemical compound C1=CC(NC(C)(CO)C)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 FCESKQRBABHKAQ-UHFFFAOYSA-N 0.000 description 1
KKMXZQHBPCIYKM-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(2-hydroxycyclohexyl)amino]benzenesulfonate Chemical compound OC1CCCCC1NC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 KKMXZQHBPCIYKM-UHFFFAOYSA-N 0.000 description 1
SWYGEDQXYMNJGV-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(2-oxo-1h-pyrimidin-6-yl)amino]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N=C1C=CNC(=O)N1 SWYGEDQXYMNJGV-UHFFFAOYSA-N 0.000 description 1
ORIULQHLBJENIA-LJQANCHMSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(2r)-2-carbamoylpyrrolidin-1-yl]benzenesulfonate Chemical compound NC(=O)[C@H]1CCCN1C1=CC=C(S(=O)(=O)OC=2C=C3NC(NC(=O)C4CC4)=NC3=CC=2)C=C1 ORIULQHLBJENIA-LJQANCHMSA-N 0.000 description 1
RATTYHJTCBOZTI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(3-methoxyphenyl)methylamino]benzenesulfonate Chemical compound COC1=CC=CC(CNC=2C=CC(=CC=2)S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)=C1 RATTYHJTCBOZTI-UHFFFAOYSA-N 0.000 description 1
RINJVWDFIQVUHG-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(3-methyl-5-oxo-4h-imidazol-2-yl)amino]benzenesulfonate Chemical compound CN1CC(=O)NC1=NC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 RINJVWDFIQVUHG-UHFFFAOYSA-N 0.000 description 1
OTXDRISAQBMHCA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(4-acetamidophenyl)methylamino]benzenesulfonate Chemical compound C1=CC(NC(=O)C)=CC=C1CNC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 OTXDRISAQBMHCA-UHFFFAOYSA-N 0.000 description 1
GXYJIMAKKNVOGI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(4-aminophenyl)methylamino]benzenesulfonate Chemical compound C1=CC(N)=CC=C1CNC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 GXYJIMAKKNVOGI-UHFFFAOYSA-N 0.000 description 1
FFQYILYIFSJMTP-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[1-(dimethylamino)propan-2-ylamino]benzenesulfonate Chemical compound C1=CC(NC(CN(C)C)C)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 FFQYILYIFSJMTP-UHFFFAOYSA-N 0.000 description 1
AFNKUONEDBNDTC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[2-(2-hydroxyethyl)piperidin-1-yl]benzenesulfonate Chemical compound OCCC1CCCCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 AFNKUONEDBNDTC-UHFFFAOYSA-N 0.000 description 1
FIWOANRBCSZVGA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[2-(n-ethyl-3-methylanilino)ethylamino]benzenesulfonate Chemical compound C=1C=CC(C)=CC=1N(CC)CCNC(C=C1)=CC=C1S(=O)(=O)OC(C=C1N=2)=CC=C1NC=2NC(=O)C1CC1 FIWOANRBCSZVGA-UHFFFAOYSA-N 0.000 description 1
DCGHGPXJVGUPAH-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[2-(propan-2-ylamino)ethylamino]benzenesulfonate Chemical compound C1=CC(NCCNC(C)C)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 DCGHGPXJVGUPAH-UHFFFAOYSA-N 0.000 description 1
NEPMGWPVRJSHTI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[3-(2-hydroxyethylamino)propylamino]benzenesulfonate Chemical compound C1=CC(NCCCNCCO)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 NEPMGWPVRJSHTI-UHFFFAOYSA-N 0.000 description 1
NKLQUZQUQJWQMU-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[3-(2-oxopyrrolidin-1-yl)propylamino]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCN1CCCC1=O NKLQUZQUQJWQMU-UHFFFAOYSA-N 0.000 description 1
APXZULWAKQCVOC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[3-(cyclohexylamino)propylamino]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCNC1CCCCC1 APXZULWAKQCVOC-UHFFFAOYSA-N 0.000 description 1
GJNAJVVYAYRDSK-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(2-hydroxyethyl)piperidin-1-yl]benzenesulfonate Chemical compound C1CC(CCO)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 GJNAJVVYAYRDSK-UHFFFAOYSA-N 0.000 description 1
AWNKJFMDDPMKNR-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(2-methoxyethyl)piperazin-1-yl]benzenesulfonate Chemical compound C1CN(CCOC)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 AWNKJFMDDPMKNR-UHFFFAOYSA-N 0.000 description 1
NLIPFPSNKGUAPD-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(3-pyrrolidin-1-ylpropyl)-1,4-diazepan-1-yl]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N(CC1)CCCN1CCCN1CCCC1 NLIPFPSNKGUAPD-UHFFFAOYSA-N 0.000 description 1
IZGOPDFWYLNFQN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(4-methoxyphenyl)piperazin-1-yl]benzenesulfonate Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(=CC=2)S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)CC1 IZGOPDFWYLNFQN-UHFFFAOYSA-N 0.000 description 1
BXIHCMSBVOKFOT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]benzenesulfonate Chemical compound C1CN(CCOCCO)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 BXIHCMSBVOKFOT-UHFFFAOYSA-N 0.000 description 1
LTYYWVKVQOGCKI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[ethyl(2-hydroxyethyl)amino]benzenesulfonate Chemical compound C1=CC(N(CCO)CC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 LTYYWVKVQOGCKI-UHFFFAOYSA-N 0.000 description 1
UPBREWNUGOONGM-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-piperidin-1-ylbenzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1CCCCC1 UPBREWNUGOONGM-UHFFFAOYSA-N 0.000 description 1
RFNWBOWIQVSXIH-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-pyrrolidin-1-ylbenzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1CCCC1 RFNWBOWIQVSXIH-UHFFFAOYSA-N 0.000 description 1
STUIVRBECMQFAW-UHFFFAOYSA-N [2-(cyclopropylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CC1 STUIVRBECMQFAW-UHFFFAOYSA-N 0.000 description 1
XEYKORZTJNMMHL-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(1-hydroxypropan-2-ylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC)=NC2=CC=1OS(=O)(=O)C1=CC=C(NC(C)CO)C=C1 XEYKORZTJNMMHL-UHFFFAOYSA-N 0.000 description 1
KUZDGERFXOLCLO-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-hydroxypropylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)NCC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCC(C)O)C=C1 KUZDGERFXOLCLO-UHFFFAOYSA-N 0.000 description 1
MNBOIFLEHYOHJQ-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrolidin-1-ylethylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)NCC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NCCN1CCCC1 MNBOIFLEHYOHJQ-UHFFFAOYSA-N 0.000 description 1
YRZAVZWEETYTOV-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 YRZAVZWEETYTOV-UHFFFAOYSA-N 0.000 description 1
KXADNXKCXRMIGA-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 2-(trifluoromethoxy)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC=C1OC(F)(F)F KXADNXKCXRMIGA-UHFFFAOYSA-N 0.000 description 1
PICHWOYICTXINJ-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 2-cyanobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC=C1C#N PICHWOYICTXINJ-UHFFFAOYSA-N 0.000 description 1
JORKTWPMXGCOBT-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3,4-dimethoxybenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=C(OC)C(OC)=C1 JORKTWPMXGCOBT-UHFFFAOYSA-N 0.000 description 1
RUAGAOSXCZWMPM-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 RUAGAOSXCZWMPM-UHFFFAOYSA-N 0.000 description 1
NHGCIPXCUDYTRT-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-fluorobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC(F)=C1 NHGCIPXCUDYTRT-UHFFFAOYSA-N 0.000 description 1
FNBMBWQKCICZRF-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-methoxybenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC(OC)=C1 FNBMBWQKCICZRF-UHFFFAOYSA-N 0.000 description 1
ZMPMOWZUCZBODC-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-nitrobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ZMPMOWZUCZBODC-UHFFFAOYSA-N 0.000 description 1
XITQHVNEMZLDBH-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(1-hydroxybutan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(CO)CC)=CC=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)OC)N2)C2=C1 XITQHVNEMZLDBH-UHFFFAOYSA-N 0.000 description 1
OIAKSBJHPHNWRB-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-hydroxypropylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCC(C)O)C=C1 OIAKSBJHPHNWRB-UHFFFAOYSA-N 0.000 description 1
XPPCCEIOFXUHFO-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-morpholin-4-ylethylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NCCN1CCOCC1 XPPCCEIOFXUHFO-UHFFFAOYSA-N 0.000 description 1
OGKUOEQBZWVSFP-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-phenylethylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NCCC1=CC=CC=C1 OGKUOEQBZWVSFP-UHFFFAOYSA-N 0.000 description 1
WPCAVSDTMWHNFX-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-piperidin-1-ylethoxy)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1OCCN1CCCCC1 WPCAVSDTMWHNFX-UHFFFAOYSA-N 0.000 description 1
AKZQLUZWOLDHLS-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(3-methoxypropylamino)benzenesulfonate Chemical compound C1=CC(NCCCOC)=CC=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)OC)N2)C2=C1 AKZQLUZWOLDHLS-UHFFFAOYSA-N 0.000 description 1
CHOKDGKAHJVMFA-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(4-hydroxybutylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCCCCO)C=C1 CHOKDGKAHJVMFA-UHFFFAOYSA-N 0.000 description 1
DOGUOCQFHURBER-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(benzylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NCC1=CC=CC=C1 DOGUOCQFHURBER-UHFFFAOYSA-N 0.000 description 1
XFOBPVWHPPELOM-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(oxolan-2-ylmethylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NCC1CCCO1 XFOBPVWHPPELOM-UHFFFAOYSA-N 0.000 description 1
AQQNMQKAEUNTIJ-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-cyanobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=C(C#N)C=C1 AQQNMQKAEUNTIJ-UHFFFAOYSA-N 0.000 description 1
MIKOSCZYCTZEPX-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 MIKOSCZYCTZEPX-UHFFFAOYSA-N 0.000 description 1
SVJQZCKFEYSCAJ-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] thiophene-2-sulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CS1 SVJQZCKFEYSCAJ-UHFFFAOYSA-N 0.000 description 1
JDEZNSQNUBFQJV-UHFFFAOYSA-N [2-(methylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(oxolan-2-ylmethylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NCC1CCCO1 JDEZNSQNUBFQJV-UHFFFAOYSA-N 0.000 description 1
RCSNVQISJVFESH-UHFFFAOYSA-N [2-(phenylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=CC=CC=1NC(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 RCSNVQISJVFESH-UHFFFAOYSA-N 0.000 description 1
WOLFLKNNESBXNR-UHFFFAOYSA-N [2-(phenylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=CC=CC=1NC(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 WOLFLKNNESBXNR-UHFFFAOYSA-N 0.000 description 1
HFWZMMIGTZWZMR-UHFFFAOYSA-N [2-(piperidin-4-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NCC1CCNCC1 HFWZMMIGTZWZMR-UHFFFAOYSA-N 0.000 description 1
BCUMMTAPWHKYMM-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)NCC=2N=CC=CC=2)N2)C2=C1 BCUMMTAPWHKYMM-UHFFFAOYSA-N 0.000 description 1
VQCSIYWETLDDDZ-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-fluoroethylamino)benzenesulfonate Chemical compound C1=CC(NCCF)=CC=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)NCC=2N=CC=CC=2)N2)C2=C1 VQCSIYWETLDDDZ-UHFFFAOYSA-N 0.000 description 1
UYTPJBJVOQCTPM-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-piperidin-1-ylethylamino)benzenesulfonate Chemical compound N=1C2=CC=C(OS(=O)(=O)C=3C=CC(NCCN4CCCCC4)=CC=3)C=C2NC=1NC(=O)NCC1=CC=CC=N1 UYTPJBJVOQCTPM-UHFFFAOYSA-N 0.000 description 1
MMOCLWWJYHCLKA-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrolidin-1-ylethylamino)benzenesulfonate Chemical compound N=1C2=CC=C(OS(=O)(=O)C=3C=CC(NCCN4CCCC4)=CC=3)C=C2NC=1NC(=O)NCC1=CC=CC=N1 MMOCLWWJYHCLKA-UHFFFAOYSA-N 0.000 description 1
GTGQZEWTEUEKRZ-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(oxan-4-ylmethylamino)benzenesulfonate Chemical compound N=1C2=CC=C(OS(=O)(=O)C=3C=CC(NCC4CCOCC4)=CC=3)C=C2NC=1NC(=O)NCC1=CC=CC=N1 GTGQZEWTEUEKRZ-UHFFFAOYSA-N 0.000 description 1
QAEBPKXYINYPFY-UHFFFAOYSA-N [2-(pyridin-3-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2NC=1NC(=O)NCC1=CC=CN=C1 QAEBPKXYINYPFY-UHFFFAOYSA-N 0.000 description 1
FGSPAWAQTBEOJK-UHFFFAOYSA-N [2-(pyridin-4-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NCC1=CC=NC=C1 FGSPAWAQTBEOJK-UHFFFAOYSA-N 0.000 description 1
FVBTZBHFBFXTKY-UHFFFAOYSA-N [2-(pyridine-3-carbonylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=CN=CC=1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 FVBTZBHFBFXTKY-UHFFFAOYSA-N 0.000 description 1
KLBVSXUIDPHJIJ-UHFFFAOYSA-N [2-(pyridine-4-carbonylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=NC=CC=1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 KLBVSXUIDPHJIJ-UHFFFAOYSA-N 0.000 description 1
UZLOXFZSPPZGDQ-UHFFFAOYSA-N [2-(tert-butylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NC(C)(C)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 UZLOXFZSPPZGDQ-UHFFFAOYSA-N 0.000 description 1
ZVKHOJLXXXZLLL-UHFFFAOYSA-N [2-[(1-ethylpyrrolidin-2-yl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound CCN1CCCC1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 ZVKHOJLXXXZLLL-UHFFFAOYSA-N 0.000 description 1
KTBKCKBKTOMTHO-UHFFFAOYSA-N [2-[(2-amino-2-methylpropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(C)(N)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 KTBKCKBKTOMTHO-UHFFFAOYSA-N 0.000 description 1
CURQUJRZCPOZFJ-UHFFFAOYSA-N [2-[(2-amino-2-methylpropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(C)(N)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 CURQUJRZCPOZFJ-UHFFFAOYSA-N 0.000 description 1
JKWZUAQAEIRFJQ-UHFFFAOYSA-N [2-[(2-amino-2-oxoethyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(=O)N)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 JKWZUAQAEIRFJQ-UHFFFAOYSA-N 0.000 description 1
JWHJLEQIKVTBGS-UHFFFAOYSA-N [2-[(2-amino-2-oxoethyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(=O)N)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 JWHJLEQIKVTBGS-UHFFFAOYSA-N 0.000 description 1
BNTSLIRAIBLSJI-UHFFFAOYSA-N [2-[(2-carbamoylpyrrolidine-1-carbonyl)amino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound NC(=O)C1CCCN1C(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 BNTSLIRAIBLSJI-UHFFFAOYSA-N 0.000 description 1
ZUYQYEOPSORCJV-UHFFFAOYSA-N [2-[(2-chlorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound ClC1=CC=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 ZUYQYEOPSORCJV-UHFFFAOYSA-N 0.000 description 1
LMEIEPYJQANBPG-UHFFFAOYSA-N [2-[(2-chlorophenyl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound ClC1=CC=CC=C1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 LMEIEPYJQANBPG-UHFFFAOYSA-N 0.000 description 1
GUCBYNQPGYTQJI-UHFFFAOYSA-N [2-[(2-cyclopropylacetyl)amino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)CC1CC1 GUCBYNQPGYTQJI-UHFFFAOYSA-N 0.000 description 1
LCHPLQNHFQFOBP-UHFFFAOYSA-N [2-[(2-fluorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound FC1=CC=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 LCHPLQNHFQFOBP-UHFFFAOYSA-N 0.000 description 1
JIYPJMZKYWWWME-UHFFFAOYSA-N [2-[(2-fluorophenyl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound FC1=CC=CC=C1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 JIYPJMZKYWWWME-UHFFFAOYSA-N 0.000 description 1
WWRZMRYZQCLDJM-UHFFFAOYSA-N [2-[(2-fluorophenyl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound FC1=CC=CC=C1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 WWRZMRYZQCLDJM-UHFFFAOYSA-N 0.000 description 1
IJQBJGPSDZRYMS-UHFFFAOYSA-N [2-[(2-hydroxy-3-methoxypropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-[(2-hydroxy-3-methoxypropyl)amino]benzenesulfonate Chemical compound C1=C2NC(NC(=O)NCC(O)COC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCC(O)COC)C=C1 IJQBJGPSDZRYMS-UHFFFAOYSA-N 0.000 description 1
QVTXENWSYPIFGG-UHFFFAOYSA-N [2-[(2-methoxyacetyl)amino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)COC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 QVTXENWSYPIFGG-UHFFFAOYSA-N 0.000 description 1
GHEJSFJEXSTJIP-UHFFFAOYSA-N [2-[(2-methoxyphenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound COC1=CC=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 GHEJSFJEXSTJIP-UHFFFAOYSA-N 0.000 description 1
YWZNHXZZKGSPEZ-UHFFFAOYSA-N [2-[(3-amino-3-oxopropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCCC(=O)N)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 YWZNHXZZKGSPEZ-UHFFFAOYSA-N 0.000 description 1
DVBNJSIAUOVIOO-UHFFFAOYSA-N [2-[(3-chlorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound ClC1=CC=CC(NC(=O)NC=2NC3=CC=C(OS(=O)(=O)C=4C=CC(=CC=4)N4C=NC=C4)C=C3N=2)=C1 DVBNJSIAUOVIOO-UHFFFAOYSA-N 0.000 description 1
MMJWXKSDMOGPMT-UHFFFAOYSA-N [2-[(3-methoxyphenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound COC1=CC=CC(NC(=O)NC=2NC3=CC=C(OS(=O)(=O)C=4C=CC(NC5CCCC5)=CC=4)C=C3N=2)=C1 MMJWXKSDMOGPMT-UHFFFAOYSA-N 0.000 description 1
KRCCVHHGDDGWAK-UHFFFAOYSA-N [2-[(3-methoxyphenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound COC1=CC=CC(NC(=O)NC=2NC3=CC=C(OS(=O)(=O)C=4C=CC(=CC=4)N4C=NC=C4)C=C3N=2)=C1 KRCCVHHGDDGWAK-UHFFFAOYSA-N 0.000 description 1
CABWYZQIWNRHFD-UHFFFAOYSA-N [2-[(4-chlorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 CABWYZQIWNRHFD-UHFFFAOYSA-N 0.000 description 1
OBRQSYVTNVRMJP-UHFFFAOYSA-N [2-[(4-hydroxycyclohexyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1CC(O)CCC1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 OBRQSYVTNVRMJP-UHFFFAOYSA-N 0.000 description 1
HXCZFNQCMVSHKP-UHFFFAOYSA-N [2-[(4-hydroxycyclohexyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C1CC(O)CCC1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 HXCZFNQCMVSHKP-UHFFFAOYSA-N 0.000 description 1
FWATVXJVVYVDES-UHFFFAOYSA-N [2-[(4-methoxyphenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 FWATVXJVVYVDES-UHFFFAOYSA-N 0.000 description 1
BTLILDHTZFWLMZ-UHFFFAOYSA-N [2-[(4-methoxyphenyl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-[(4-methoxyphenyl)methylamino]benzenesulfonate Chemical compound C1=CC(OC)=CC=C1CNC(=O)NC(NC1=C2)=NC1=CC=C2OS(=O)(=O)C(C=C1)=CC=C1NCC1=CC=C(OC)C=C1 BTLILDHTZFWLMZ-UHFFFAOYSA-N 0.000 description 1
MHEHIKSDBBUJQJ-UHFFFAOYSA-N [2-[(4-methylpiperazine-1-carbonyl)amino]-3h-benzimidazol-5-yl] 4-(4-methylpiperazin-1-yl)benzenesulfonate Chemical compound C1CN(C)CCN1C(=O)NC(NC1=C2)=NC1=CC=C2OS(=O)(=O)C1=CC=C(N2CCN(C)CC2)C=C1 MHEHIKSDBBUJQJ-UHFFFAOYSA-N 0.000 description 1
WIMBEXQMUJGBMF-UHFFFAOYSA-N [2-[2-(2-hydroxyethoxy)ethylcarbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCCOCCO)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 WIMBEXQMUJGBMF-UHFFFAOYSA-N 0.000 description 1
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DQEOVESFEQJROS-UHFFFAOYSA-N methyl 2-[[6-(4-imidazol-1-ylphenyl)sulfonyloxy-1h-benzimidazol-2-yl]carbamoylamino]acetate Chemical compound C=1C=C2NC(NC(=O)NCC(=O)OC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 DQEOVESFEQJROS-UHFFFAOYSA-N 0.000 description 1
LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
UELSRFASSXYIHV-UHFFFAOYSA-N methyl 3-[4-[[2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl]oxysulfonyl]anilino]propanoate Chemical compound C1=CC(NCCC(=O)OC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 UELSRFASSXYIHV-UHFFFAOYSA-N 0.000 description 1
PQGJIKZVHIURPG-UHFFFAOYSA-N methyl 4-[[6-[4-(cyclopentylamino)phenyl]sulfonyloxy-1h-benzimidazol-2-yl]amino]-4-oxobutanoate Chemical compound C1=C2NC(NC(=O)CCC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 PQGJIKZVHIURPG-UHFFFAOYSA-N 0.000 description 1
SYJYYCICPVPGKH-UHFFFAOYSA-N methyl 4-[[6-[4-(cyclopentylamino)phenyl]sulfonyloxy-1h-benzimidazol-2-yl]carbamoylamino]butanoate Chemical compound C=1C=C2NC(NC(=O)NCCCC(=O)OC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 SYJYYCICPVPGKH-UHFFFAOYSA-N 0.000 description 1
QXQPKZAOIHRDNE-UHFFFAOYSA-N methyl 5-[[6-(4-imidazol-1-ylphenyl)sulfonyloxy-1h-benzimidazol-2-yl]amino]-5-oxopentanoate Chemical compound C=1C=C2NC(NC(=O)CCCC(=O)OC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 QXQPKZAOIHRDNE-UHFFFAOYSA-N 0.000 description 1
KQEKUZPFFPXVCG-UHFFFAOYSA-N methyl 6-[4-[[2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl]oxysulfonyl]anilino]hexanoate Chemical compound C1=CC(NCCCCCC(=O)OC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 KQEKUZPFFPXVCG-UHFFFAOYSA-N 0.000 description 1
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JMRLHZJPLGCDSR-UHFFFAOYSA-N tert-butyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC(C)(C)C)=NC2=C1 JMRLHZJPLGCDSR-UHFFFAOYSA-N 0.000 description 1
UQJXXWHAJKRDKY-UHFFFAOYSA-N tert-butyl n-[[(2-methylpropan-2-yl)oxycarbonylamino]-methylsulfanylmethylidene]carbamate Chemical compound CC(C)(C)OC(=O)NC(SC)=NC(=O)OC(C)(C)C UQJXXWHAJKRDKY-UHFFFAOYSA-N 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
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125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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229960000303 topotecan Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000007704 transition Effects 0.000 description 1
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201000005112 urinary bladder cancer Diseases 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
HHJUWIANJFBDHT-KOTLKJBCSA-N vindesine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(N)=O)N4C)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 HHJUWIANJFBDHT-KOTLKJBCSA-N 0.000 description 1
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GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

NO20041214A 2001-09-26 2004-03-23 Substituerte benzimidazolforbindelser og deres anvendelse for fremstilling av medikamenter for behandling av cancer NO327008B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01402460A EP1298125A1 (en)	2001-09-26	2001-09-26	Substituted benzimidazole compounds and their use for the treatment of cancer
PCT/EP2002/011353 WO2003028721A2 (en)	2001-09-26	2002-09-26	Substituted benzimidazole compounds and their use for the treatment of cancer

Publications (2)

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NO20041214L NO20041214L (no)	2004-06-24
NO327008B1 true NO327008B1 (no)	2009-04-06

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Country Status (35)

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US (1)	US7041668B2 (el)
EP (2)	EP1298125A1 (el)
JP (1)	JP4510450B2 (el)
KR (1)	KR100891439B1 (el)
CN (1)	CN100346786C (el)
AR (1)	AR037096A1 (el)
AT (1)	ATE386517T1 (el)
AU (1)	AU2002337151B2 (el)
BR (1)	BR0212856A (el)
CA (1)	CA2461622C (el)
CO (1)	CO5570675A2 (el)
CY (1)	CY1107953T1 (el)
DE (1)	DE60225159T2 (el)
DK (1)	DK1432417T3 (el)
EA (1)	EA006802B1 (el)
ES (1)	ES2301682T3 (el)
GT (1)	GT200200190A (el)
HK (1)	HK1068551A1 (el)
HR (1)	HRPK20040293B3 (el)
HU (1)	HUP0401756A3 (el)
IL (1)	IL161059A0 (el)
ME (1)	MEP16808A (el)
MX (1)	MXPA04002042A (el)
MY (1)	MY135339A (el)
NO (1)	NO327008B1 (el)
NZ (1)	NZ531246A (el)
PA (1)	PA8555501A1 (el)
PE (1)	PE20030427A1 (el)
PL (1)	PL369527A1 (el)
PT (1)	PT1432417E (el)
RS (1)	RS50896B (el)
SI (1)	SI1432417T1 (el)
UY (1)	UY27452A1 (el)
WO (1)	WO2003028721A2 (el)
ZA (1)	ZA200401887B (el)

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AU2011250847B2 (en) *	2003-06-23	2013-06-20	Bhi Limited Partnership	Methods and compositions for treating amyloid-related diseases
US20070010573A1 (en)	2003-06-23	2007-01-11	Xianqi Kong	Methods and compositions for treating amyloid-related diseases
US20070208166A1 (en) *	2003-10-24	2007-09-06	Exelixis, Inc.	Tao Kinase Modulators And Method Of Use
DE102004010207A1 (de)	2004-03-02	2005-09-15	Aventis Pharma S.A.	Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate
FR2868421B1 (fr) *	2004-04-01	2008-08-01	Aventis Pharma Sa	Nouveaux benzothiazoles et leur utilisation comme medicaments
EP1598348A1 (en)	2004-05-18	2005-11-23	Aventis Pharma Deutschland GmbH	Novel pyridazinone derivatives as inhibitors of CDK2
EP1836161B1 (en)	2004-12-22	2016-07-20	BHI Limited Partnership	Methods and compositions for treating amyloid-related diseases
UA92180C2 (en) *	2005-09-06	2010-10-11	Смиткляйн Бичам Корпорейшн	Benzimidazole thiophene compounds as plk inhibitors
FR2891273B1 (fr) *	2005-09-27	2007-11-23	Aventis Pharma Sa	NOUVEAUX DERIVES BENZIMIDAZOLES ET BENZOTHIAZOLES, LEUR PREPARATION ET LEUR UTILISATION PHARMACEUTIQUE NOTAMMENT COMME INHIBITEURS DE CMet
PL2089417T3 (pl)	2006-10-12	2015-07-31	Bhi Lp	Sposoby, związki, kompozycje i nośniki dostarczające kwas 3-amino-1-propanosulfonowy
PA8792501A1 (es)	2007-08-09	2009-04-23	Sanofi Aventis	Nuevos derivados de 6-triazolopiridacina-sulfanil benzotiazol y bencimidazol,su procedimiento de preparación,su aplicación como medicamentos,composiciones farmacéuticas y nueva utilización principalmente como inhibidores de met.
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2001
- 2001-09-26 EP EP01402460A patent/EP1298125A1/en not_active Withdrawn
2002
- 2002-09-17 PE PE2002000913A patent/PE20030427A1/es not_active Application Discontinuation
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Publication number	Publication date
WO2003028721A3 (en)	2003-12-11
PL369527A1 (en)	2005-05-02
HK1068551A1 (en)	2005-04-29
GT200200190A (es)	2003-11-11
MEP16808A (en)	2010-06-10
HRP20040293A2 (en)	2005-06-30
MY135339A (en)	2008-03-31
KR20040048904A (ko)	2004-06-10
RS50896B (sr)	2010-08-31
DE60225159D1 (de)	2008-04-03
DK1432417T3 (da)	2008-06-16
HUP0401756A3 (en)	2005-06-28
EA200400475A1 (ru)	2004-08-26
KR100891439B1 (ko)	2009-04-03
NO20041214L (no)	2004-06-24
CA2461622C (en)	2008-12-02
US7041668B2 (en)	2006-05-09
CN100346786C (zh)	2007-11-07
PT1432417E (pt)	2008-05-23
WO2003028721A2 (en)	2003-04-10
NZ531246A (en)	2006-06-30
HRPK20040293B3 (en)	2007-06-30
EP1432417B1 (en)	2008-02-20
EA006802B1 (ru)	2006-04-28
CO5570675A2 (es)	2005-10-31
SI1432417T1 (sl)	2008-08-31
ES2301682T3 (es)	2008-07-01
BR0212856A (pt)	2004-09-14
ATE386517T1 (de)	2008-03-15
AR037096A1 (es)	2004-10-20
EP1432417A2 (en)	2004-06-30
YU21404A (sh)	2006-08-17
CY1107953T1 (el)	2013-09-04
JP2005504112A (ja)	2005-02-10
HUP0401756A2 (hu)	2005-01-28
AU2002337151B2 (en)	2007-04-26
CA2461622A1 (en)	2003-04-10
EP1298125A1 (en)	2003-04-02
DE60225159T2 (de)	2009-02-19
UY27452A1 (es)	2003-02-28
MXPA04002042A (es)	2004-06-07
ZA200401887B (en)	2005-05-31
US20050014811A1 (en)	2005-01-20
JP4510450B2 (ja)	2010-07-21
PE20030427A1 (es)	2003-06-20
CN1558761A (zh)	2004-12-29
IL161059A0 (en)	2004-08-31
PA8555501A1 (es)	2003-06-30

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