ZA200401887B - Substituted benzimidazole compounds and their use for the treatment of cancer. - Google Patents

Substituted benzimidazole compounds and their use for the treatment of cancer. Download PDF

Info

Publication number: ZA200401887B
Authority: ZA; South Africa
Prior art keywords: benzoimidazol; ester; benzenesulfonic acid; amino; ureido
Prior art date: 2001-09-26

Application number

ZA200401887A

Other languages

English (en)

Inventor

Francois Clerc

Isabelle Depaty

Stephanie Deprets

Manfred Roesner

Francois Hamy

Odile Angouillant-Boniface

Chantal Carrez

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

2004-03-08

Publication date

2005-05-31

2004-03-08 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2005-05-31 Publication of ZA200401887B publication Critical patent/ZA200401887B/en

Links

206010028980 Neoplasm Diseases 0.000 title description 8
201000011510 cancer Diseases 0.000 title description 6
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
-1 hydroxyalkyl amide Chemical group 0.000 claims description 55
125000002252 acyl group Chemical group 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 22
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 13
239000002253 acid Chemical class 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000004404 heteroalkyl group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
229920001774 Perfluoroether Chemical group 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000005122 aminoalkylamino group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
125000005241 heteroarylamino group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
229940002612 prodrug Drugs 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
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150000002148 esters Chemical class 0.000 description 32
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GUVLEGVYXSGPBV-UHFFFAOYSA-N 4-imidazol-1-ylbenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1N1C=NC=C1 GUVLEGVYXSGPBV-UHFFFAOYSA-N 0.000 description 13
CBUGQMSZOGYQED-UHFFFAOYSA-N 4-(cyclopentylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC1CCCC1 CBUGQMSZOGYQED-UHFFFAOYSA-N 0.000 description 12
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125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
230000032823 cell division Effects 0.000 description 2
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XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
LJCJRRKKAKAKRV-UHFFFAOYSA-N (2-amino-2-methylpropyl) 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CC(C)(N)COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LJCJRRKKAKAKRV-UHFFFAOYSA-N 0.000 description 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 description 1
DQCFNPONIOMLBZ-UHFFFAOYSA-N 4-(1-hydroxypropan-2-ylamino)benzenesulfonic acid Chemical compound OCC(C)NC1=CC=C(S(O)(=O)=O)C=C1 DQCFNPONIOMLBZ-UHFFFAOYSA-N 0.000 description 1
IVXYBHSBVPMCSK-UHFFFAOYSA-N 4-(1-methoxypropan-2-ylamino)benzenesulfonic acid Chemical compound COCC(C)NC1=CC=C(S(O)(=O)=O)C=C1 IVXYBHSBVPMCSK-UHFFFAOYSA-N 0.000 description 1
WKAGWIWFDMCATO-UHFFFAOYSA-N 4-(2-imidazol-1-ylethylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NCCN1C=NC=C1 WKAGWIWFDMCATO-UHFFFAOYSA-N 0.000 description 1
KFHTZBCMDJHSHP-UHFFFAOYSA-N 4-(2-methoxyethylamino)benzenesulfonic acid Chemical compound COCCNC1=CC=C(S(O)(=O)=O)C=C1 KFHTZBCMDJHSHP-UHFFFAOYSA-N 0.000 description 1
MWHGUSHBYNYWMW-UHFFFAOYSA-N 4-(2-phenoxyethylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NCCOC1=CC=CC=C1 MWHGUSHBYNYWMW-UHFFFAOYSA-N 0.000 description 1
VWSLARPURYGVHK-UHFFFAOYSA-N 4-(2-piperazin-1-ylethylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NCCN1CCNCC1 VWSLARPURYGVHK-UHFFFAOYSA-N 0.000 description 1
OMEZFOQEMAINAP-UHFFFAOYSA-N 4-(2-piperidin-1-ylethylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NCCN1CCCCC1 OMEZFOQEMAINAP-UHFFFAOYSA-N 0.000 description 1
BNINRSWLCPUDSU-UHFFFAOYSA-N 4-(3-methoxypropylamino)benzenesulfonic acid Chemical compound COCCCNC1=CC=C(S(O)(=O)=O)C=C1 BNINRSWLCPUDSU-UHFFFAOYSA-N 0.000 description 1
WMNKFHGRNHSSRJ-UHFFFAOYSA-N 4-(3-pyrrolidin-1-ylpropylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NCCCN1CCCC1 WMNKFHGRNHSSRJ-UHFFFAOYSA-N 0.000 description 1
LJPQSZVZLDUAQO-UHFFFAOYSA-N 4-(benzylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NCC1=CC=CC=C1 LJPQSZVZLDUAQO-UHFFFAOYSA-N 0.000 description 1
PKBHYLHBQAUNGE-UHFFFAOYSA-N 4-(oxolan-2-ylmethylamino)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NCC1OCCC1 PKBHYLHBQAUNGE-UHFFFAOYSA-N 0.000 description 1
ABDSHBXUDYNIOE-UHFFFAOYSA-N 4-(prop-2-ynylamino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(NCC#C)C=C1 ABDSHBXUDYNIOE-UHFFFAOYSA-N 0.000 description 1
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LRVFMCCCRHZRJN-UHFFFAOYSA-N [2-(1-hydroxypropan-2-ylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NC(CO)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 LRVFMCCCRHZRJN-UHFFFAOYSA-N 0.000 description 1
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PRINFDDUEJIJAL-UHFFFAOYSA-N [2-(benzylcarbamoylamino)-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=CC=C1 PRINFDDUEJIJAL-UHFFFAOYSA-N 0.000 description 1
FCTVMZFLKXPPIG-UHFFFAOYSA-N [2-(cyclobutylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate;[2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound N=1C2=CC=C(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)C=C2NC=1NC(=O)NC1CCC1.N=1C2=CC=C(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)C=C2NC=1NC(=O)NCC1=CC=CC=N1 FCTVMZFLKXPPIG-UHFFFAOYSA-N 0.000 description 1
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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
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CUWFYWDFFAMFPP-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(2-methoxyphenyl)methylamino]benzenesulfonate Chemical compound COC1=CC=CC=C1CNC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 CUWFYWDFFAMFPP-UHFFFAOYSA-N 0.000 description 1
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DXKZARMPLMSSKV-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[2-(hydroxymethyl)anilino]benzenesulfonate Chemical compound OCC1=CC=CC=C1NC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 DXKZARMPLMSSKV-UHFFFAOYSA-N 0.000 description 1
WSJODZUAOXVPMV-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[3-(methylamino)propylamino]benzenesulfonate Chemical compound C1=CC(NCCCNC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 WSJODZUAOXVPMV-UHFFFAOYSA-N 0.000 description 1
DNVMPLOWNBWWFD-UHFFFAOYSA-N [2-(cyclopropylcarbamoylamino)-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)NC1CC1 DNVMPLOWNBWWFD-UHFFFAOYSA-N 0.000 description 1
TVNGYSVWYIKZQQ-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(oxolan-2-ylmethylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NCC1CCCO1 TVNGYSVWYIKZQQ-UHFFFAOYSA-N 0.000 description 1
RLVRYIMMTOCQAF-UHFFFAOYSA-N [2-(hexanoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)CCCCC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 RLVRYIMMTOCQAF-UHFFFAOYSA-N 0.000 description 1
XLXNBWHKUQDDGX-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 XLXNBWHKUQDDGX-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
NGUKVPAWEVUDGA-UHFFFAOYSA-N [2-(piperidin-4-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)NCC1CCNCC1 NGUKVPAWEVUDGA-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
VHSMXHKFUIJDAU-UHFFFAOYSA-N [2-(tert-butylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NC(C)(C)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 VHSMXHKFUIJDAU-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
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
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
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
DMYZYKJDKZFYPC-UHFFFAOYSA-N [2-[[4-(dimethylamino)phenyl]carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 DMYZYKJDKZFYPC-UHFFFAOYSA-N 0.000 description 1
BCQITNPOCYNAOY-UHFFFAOYSA-N [2-[methyl(methylcarbamoyl)amino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(N(C)C(=O)NC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 BCQITNPOCYNAOY-UHFFFAOYSA-N 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
101150073031 cdk2 gene Proteins 0.000 description 1
230000012820 cell cycle checkpoint Effects 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
230000009028 cell transition Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 1
229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 1
GYOZYWVXFNDGLU-XLPZGREQSA-N dTMP Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 GYOZYWVXFNDGLU-XLPZGREQSA-N 0.000 description 1
230000007547 defect Effects 0.000 description 1
XWVLIAVUHQVRSQ-UHFFFAOYSA-N ethyl 1-[[6-(4-imidazol-1-ylphenyl)sulfonyloxy-1h-benzimidazol-2-yl]carbamoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 XWVLIAVUHQVRSQ-UHFFFAOYSA-N 0.000 description 1
CDHVBMWHRGGHCA-UHFFFAOYSA-N ethyl 1-[[6-[4-(cyclopentylamino)phenyl]sulfonyloxy-1h-benzimidazol-2-yl]carbamoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 CDHVBMWHRGGHCA-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
230000006951 hyperphosphorylation Effects 0.000 description 1
230000000415 inactivating effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
238000000034 method Methods 0.000 description 1
WTVSCTQLMIXHOZ-UHFFFAOYSA-N methyl 4-[[6-[4-(cyclopentylamino)phenyl]sulfonyloxy-1h-benzimidazol-2-yl]amino]-4-oxobutanoate;methyl 5-[[6-[4-(cyclopentylamino)phenyl]sulfonyloxy-1h-benzimidazol-2-yl]amino]-5-oxopentanoate Chemical compound C1=C2NC(NC(=O)CCC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1.C1=C2NC(NC(=O)CCCC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 WTVSCTQLMIXHOZ-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
BLWYXBNNBYXPPL-UHFFFAOYSA-N methyl pyrrolidine-2-carboxylate Chemical compound COC(=O)C1CCCN1 BLWYXBNNBYXPPL-UHFFFAOYSA-N 0.000 description 1
230000035772 mutation Effects 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
210000005170 neoplastic cell Anatomy 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000002611 ovarian Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
238000009521 phase II clinical trial Methods 0.000 description 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
230000007704 transition Effects 0.000 description 1
230000002792 vascular Effects 0.000 description 1

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200401887A 2001-09-26 2004-03-08 Substituted benzimidazole compounds and their use for the treatment of cancer. ZA200401887B (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
ZA200401887B true ZA200401887B (en)	2005-05-31

Family

ID=8182891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200401887A ZA200401887B (en)	2001-09-26	2004-03-08	Substituted benzimidazole compounds and their use for the treatment of cancer.

Country Status (35)

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

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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
WO2005040355A2 (en) *	2003-10-24	2005-05-06	Exelixis, Inc.	Tao kinase modulators and methods 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
AU2005326962A1 (en)	2004-12-22	2006-08-17	Bellus Health (International) Limited	Methods and compositions for treating amyloid-related diseases
CN101300251B (zh) *	2005-09-06	2011-08-03	史密丝克莱恩比彻姆公司	作为plk抑制剂的苯并咪唑噻吩化合物
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
SI2089417T1 (sl)	2006-10-12	2015-04-30	Bhi Limited Partnership	Metode, spojine, sestavki in vektorji za dostavo 3-amino-1-propansulfonske kisline
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.
MY156691A (en) *	2007-10-12	2016-03-15	Abbvie Bahamas Ltd	2-(r)-2-methylpyrrolidin-2-yl)-1h-benzimidazole-4-carboxamide crystalline from 1
FR2922550B1 (fr)	2007-10-19	2009-11-27	Sanofi Aventis	Nouveaux derives de 6-aryl/heteroalkyloxy benzothiazole et benzimidazole, application comme medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de cmet
FR2941949B1 (fr)	2009-02-06	2011-04-01	Sanofi Aventis	Derives de 6-(6-o-cycloalkyl ou 6-nh-cycloalkyl- triazolopyridazine-sulfanyl)benzothiazoles et benzimidazoles preparation, application comme medicaments et utilisation comme inhibiteurs de met.
FR2941952B1 (fr)	2009-02-06	2011-04-01	Sanofi Aventis	Derives de 6-(6-substitue-triazolopyridazine-sulfanyl) 5-fluoro-benzothiazoles et 5-fluoro-benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met.
FR2941950B1 (fr)	2009-02-06	2011-04-01	Sanofi Aventis	Derives de 6-(6-o-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met.
FR2941951B1 (fr)	2009-02-06	2011-04-01	Sanofi Aventis	Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met.
WO2011091152A1 (en) *	2010-01-22	2011-07-28	Pablo Gastaminza	Inhibitors of hepatitis c virus infection
CN114469984A (zh)	2015-08-25	2022-05-13	阿尔尼拉姆医药品有限公司	用于治疗前蛋白转化酶枯草杆菌蛋白酶kexin(pcsk9)基因相关障碍的方法和组合物

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DE2441201C2 (de) *	1974-08-28	1986-08-07	Hoechst Ag, 6230 Frankfurt	Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung
DE2541752A1 (de)	1975-09-19	1977-03-24	Hoechst Ag	Anthelminthisch wirksame 2-carbalkoxyamino-5(6)-phenyl-sulfonyloxy- benzimidazole und verfahren zu ihrer herstellung
DE3247615A1 (de) *	1982-12-23	1984-07-05	Hoechst Ag, 6230 Frankfurt	Substituierte phenylsulfonyloxybenzimidazolcarbaminate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
GB9900752D0 (en) *	1999-01-15	1999-03-03	Angiogene Pharm Ltd	Benzimidazole vascular damaging agents
US6693125B2 (en) *	2001-01-24	2004-02-17	Combinatorx Incorporated	Combinations of drugs (e.g., a benzimidazole and pentamidine) for the treatment of neoplastic disorders

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
- 2002-09-24 UY UY27452A patent/UY27452A1/es unknown
- 2002-09-25 GT GT200200190A patent/GT200200190A/es unknown
- 2002-09-25 MY MYPI20023586A patent/MY135339A/en unknown
- 2002-09-26 JP JP2003532053A patent/JP4510450B2/ja not_active Expired - Fee Related
- 2002-09-26 DE DE60225159T patent/DE60225159T2/de not_active Expired - Lifetime
- 2002-09-26 CN CNB028187458A patent/CN100346786C/zh not_active Expired - Fee Related
- 2002-09-26 IL IL16105902A patent/IL161059A0/xx unknown
- 2002-09-26 AU AU2002337151A patent/AU2002337151B2/en not_active Ceased
- 2002-09-26 MX MXPA04002042A patent/MXPA04002042A/es active IP Right Grant
- 2002-09-26 PT PT02772370T patent/PT1432417E/pt unknown
- 2002-09-26 KR KR1020047004365A patent/KR100891439B1/ko not_active IP Right Cessation
- 2002-09-26 AR ARP020103629A patent/AR037096A1/es unknown
- 2002-09-26 ME MEP-168/08A patent/MEP16808A/xx unknown
- 2002-09-26 HU HU0401756A patent/HUP0401756A3/hu unknown
- 2002-09-26 AT AT02772370T patent/ATE386517T1/de active
- 2002-09-26 DK DK02772370T patent/DK1432417T3/da active
- 2002-09-26 CA CA002461622A patent/CA2461622C/en not_active Expired - Fee Related
- 2002-09-26 PL PL02369527A patent/PL369527A1/xx not_active Application Discontinuation
- 2002-09-26 WO PCT/EP2002/011353 patent/WO2003028721A2/en active IP Right Grant
- 2002-09-26 SI SI200230686T patent/SI1432417T1/sl unknown
- 2002-09-26 ES ES02772370T patent/ES2301682T3/es not_active Expired - Lifetime
- 2002-09-26 PA PA20028555501A patent/PA8555501A1/es unknown
- 2002-09-26 EP EP02772370A patent/EP1432417B1/en not_active Expired - Lifetime
- 2002-09-26 EA EA200400475A patent/EA006802B1/ru not_active IP Right Cessation
- 2002-09-26 BR BR0212856-0A patent/BR0212856A/pt not_active IP Right Cessation
- 2002-09-26 NZ NZ531246A patent/NZ531246A/en not_active IP Right Cessation
- 2002-09-26 RS YUP-214/04A patent/RS50896B/sr unknown
2004
- 2004-03-08 ZA ZA200401887A patent/ZA200401887B/en unknown
- 2004-03-23 NO NO20041214A patent/NO327008B1/no not_active IP Right Cessation
- 2004-03-25 CO CO04028337A patent/CO5570675A2/es not_active Application Discontinuation
- 2004-03-25 HR HR20040293A patent/HRPK20040293B3/xx not_active IP Right Cessation
- 2004-03-25 US US10/808,889 patent/US7041668B2/en not_active Expired - Fee Related
2005
- 2005-02-07 HK HK05101028A patent/HK1068551A1/xx not_active IP Right Cessation
2008
- 2008-05-20 CY CY20081100526T patent/CY1107953T1/el unknown

Also Published As

Publication number	Publication date
US20050014811A1 (en)	2005-01-20
CA2461622A1 (en)	2003-04-10
JP4510450B2 (ja)	2010-07-21
CN100346786C (zh)	2007-11-07
HUP0401756A3 (en)	2005-06-28
EP1432417A2 (en)	2004-06-30
EA200400475A1 (ru)	2004-08-26
EA006802B1 (ru)	2006-04-28
JP2005504112A (ja)	2005-02-10
WO2003028721A3 (en)	2003-12-11
MXPA04002042A (es)	2004-06-07
HRPK20040293B3 (en)	2007-06-30
BR0212856A (pt)	2004-09-14
DE60225159T2 (de)	2009-02-19
HRP20040293A2 (en)	2005-06-30
PE20030427A1 (es)	2003-06-20
EP1432417B1 (en)	2008-02-20
CO5570675A2 (es)	2005-10-31
DK1432417T3 (da)	2008-06-16
CY1107953T1 (el)	2013-09-04
GT200200190A (es)	2003-11-11
KR20040048904A (ko)	2004-06-10
NO327008B1 (no)	2009-04-06
PT1432417E (pt)	2008-05-23
IL161059A0 (en)	2004-08-31
PA8555501A1 (es)	2003-06-30
HK1068551A1 (en)	2005-04-29
AR037096A1 (es)	2004-10-20
ATE386517T1 (de)	2008-03-15
RS50896B (sr)	2010-08-31
US7041668B2 (en)	2006-05-09
YU21404A (sh)	2006-08-17
SI1432417T1 (sl)	2008-08-31
PL369527A1 (en)	2005-05-02
KR100891439B1 (ko)	2009-04-03
HUP0401756A2 (hu)	2005-01-28
CN1558761A (zh)	2004-12-29
DE60225159D1 (de)	2008-04-03
UY27452A1 (es)	2003-02-28
NZ531246A (en)	2006-06-30
WO2003028721A2 (en)	2003-04-10
EP1298125A1 (en)	2003-04-02
MY135339A (en)	2008-03-31
NO20041214L (no)	2004-06-24
AU2002337151B2 (en)	2007-04-26
ES2301682T3 (es)	2008-07-01
MEP16808A (en)	2010-06-10
CA2461622C (en)	2008-12-02

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