RU2008138163A - 4-фенилтиазол-5-карбоновые кислоты и амиды 4-фенилтиазол-5-карбоновой кислоты как ингибиторы polo-подобной киназы plk1 - Google Patents
4-фенилтиазол-5-карбоновые кислоты и амиды 4-фенилтиазол-5-карбоновой кислоты как ингибиторы polo-подобной киназы plk1 Download PDFInfo
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- RU2008138163A RU2008138163A RU2008138163/04A RU2008138163A RU2008138163A RU 2008138163 A RU2008138163 A RU 2008138163A RU 2008138163/04 A RU2008138163/04 A RU 2008138163/04A RU 2008138163 A RU2008138163 A RU 2008138163A RU 2008138163 A RU2008138163 A RU 2008138163A
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- Prior art keywords
- carboxylic acid
- dimethoxybenzimidazol
- phenylthiazole
- thiazole
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- 102100031463 Serine/threonine-protein kinase PLK1 Human genes 0.000 title claims 5
- 108010056274 polo-like kinase 1 Proteins 0.000 title claims 5
- -1 Amides 4-Phenylthiazole-5-Carboxylic Acids Chemical class 0.000 title claims 4
- NGTZFWMOTDGMKO-UHFFFAOYSA-N 4-phenyl-1,3-thiazole-5-carboxylic acid Chemical class S1C=NC(C=2C=CC=CC=2)=C1C(=O)O NGTZFWMOTDGMKO-UHFFFAOYSA-N 0.000 title 1
- 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 125000004429 atom Chemical group 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 239000001301 oxygen Substances 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 239000011593 sulfur Substances 0.000 claims abstract 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 230000001575 pathological effect Effects 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- YQLVQWSSUDEOAJ-UHFFFAOYSA-N 2-(5-methoxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=NC2=CC(OC)=CC=C2N1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 YQLVQWSSUDEOAJ-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- LRXLYKKRELKYOF-UHFFFAOYSA-N 2-(4-carboxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC=CC(=C3N=C2)C(O)=O)=NC=1C1=CC=CC=C1 LRXLYKKRELKYOF-UHFFFAOYSA-N 0.000 claims 1
- PNKPQBBBXKMHCY-UHFFFAOYSA-N 2-(4-hydroxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC=CC(O)=C3N=C2)=NC=1C1=CC=CC=C1 PNKPQBBBXKMHCY-UHFFFAOYSA-N 0.000 claims 1
- IXIFALPWMQDPBP-UHFFFAOYSA-N 2-(5,6-dihydroxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC(O)=C(O)C=C3N=C2)=NC=1C1=CC=CC=C1 IXIFALPWMQDPBP-UHFFFAOYSA-N 0.000 claims 1
- SRPRDOMMUDBFNU-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(1-methylindol-5-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=C2N(C)C=CC2=CC(C=2N=C(SC=2C(O)=O)N2C=NC=3C=C(C(=CC=32)OC)OC)=C1 SRPRDOMMUDBFNU-UHFFFAOYSA-N 0.000 claims 1
- UHGNRWHLJFLJGB-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(2-hydroxyphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1O UHGNRWHLJFLJGB-UHFFFAOYSA-N 0.000 claims 1
- YDQZCIGOVKGQCA-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(2-methylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1C YDQZCIGOVKGQCA-UHFFFAOYSA-N 0.000 claims 1
- RYVMXWTXDWJVDB-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(3,4-dimethoxyphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C(O)=O)SC(N2C3=CC(OC)=C(OC)C=C3N=C2)=N1 RYVMXWTXDWJVDB-UHFFFAOYSA-N 0.000 claims 1
- RYGPCANKAYNMPZ-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(3-ethenylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(C=C)=C1 RYGPCANKAYNMPZ-UHFFFAOYSA-N 0.000 claims 1
- GESAUXAKNJZEKH-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(3-fluorophenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(F)=C1 GESAUXAKNJZEKH-UHFFFAOYSA-N 0.000 claims 1
- SNWRTLGGPVJVQK-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(3-hydroxyphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(O)=C1 SNWRTLGGPVJVQK-UHFFFAOYSA-N 0.000 claims 1
- HLVGWBJEVPPBKB-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(3-methoxyphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound COC1=CC=CC(C2=C(SC(=N2)N2C3=CC(OC)=C(OC)C=C3N=C2)C(O)=O)=C1 HLVGWBJEVPPBKB-UHFFFAOYSA-N 0.000 claims 1
- SRWMWTKXCNSZLF-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(3-propan-2-ylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(C(C)C)=C1 SRWMWTKXCNSZLF-UHFFFAOYSA-N 0.000 claims 1
- YRSHBRPNANQIHZ-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(4-ethenylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=C(C=C)C=C1 YRSHBRPNANQIHZ-UHFFFAOYSA-N 0.000 claims 1
- DJXMEFSAUOIGIZ-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(4-methoxyphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C(O)=O)SC(N2C3=CC(OC)=C(OC)C=C3N=C2)=N1 DJXMEFSAUOIGIZ-UHFFFAOYSA-N 0.000 claims 1
- YPENMNILWSQOND-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-(4-methylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=C(C)C=C1 YPENMNILWSQOND-UHFFFAOYSA-N 0.000 claims 1
- PHUBUICFEOKUND-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-[3-(dimethylcarbamoyl)phenyl]-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(C(=O)N(C)C)=C1 PHUBUICFEOKUND-UHFFFAOYSA-N 0.000 claims 1
- USLRCDHOSVKZLZ-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-[3-(hydroxymethyl)phenyl]-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(CO)=C1 USLRCDHOSVKZLZ-UHFFFAOYSA-N 0.000 claims 1
- GCBRNDVJHYCXHT-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(C(F)(F)F)=C1 GCBRNDVJHYCXHT-UHFFFAOYSA-N 0.000 claims 1
- IHWFBJOKEWLGGY-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-naphthalen-1-yl-1,3-thiazole-5-carboxylic acid Chemical compound C1=CC=C2C(C=3N=C(SC=3C(O)=O)N3C=NC=4C=C(C(=CC=43)OC)OC)=CC=CC2=C1 IHWFBJOKEWLGGY-UHFFFAOYSA-N 0.000 claims 1
- OYGLQKVRLMQHLU-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=NC=1C1=CC=CC=C1 OYGLQKVRLMQHLU-UHFFFAOYSA-N 0.000 claims 1
- AYJRBUKJAAYPMJ-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 AYJRBUKJAAYPMJ-UHFFFAOYSA-N 0.000 claims 1
- KKSARMOSVBRKOK-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-phenyl-5-(2h-tetrazol-5-yl)-1,3-thiazole Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(S1)=NC(C=2C=CC=CC=2)=C1C1=NN=NN1 KKSARMOSVBRKOK-UHFFFAOYSA-N 0.000 claims 1
- GDFVHRAINCHFNY-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-pyridin-3-yl-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CN=C1 GDFVHRAINCHFNY-UHFFFAOYSA-N 0.000 claims 1
- DATNXVFSSNJTPA-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-4-thiophen-3-yl-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C=1C=CSC=1 DATNXVFSSNJTPA-UHFFFAOYSA-N 0.000 claims 1
- FRDRJZUWWFSZMH-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-n,4-diphenyl-1,3-thiazole-5-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(S1)=NC(C=2C=CC=CC=2)=C1C(=O)NC1=CC=CC=C1 FRDRJZUWWFSZMH-UHFFFAOYSA-N 0.000 claims 1
- JGFXBKCPGKLGOC-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-n,n-dimethyl-4-phenyl-1,3-thiazole-5-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(=O)N(C)C)=NC=1C1=CC=CC=C1 JGFXBKCPGKLGOC-UHFFFAOYSA-N 0.000 claims 1
- LSPBWHHLSDAMJA-UHFFFAOYSA-N 2-(5,6-dimethoxybenzimidazol-1-yl)-n-ethyl-4-phenyl-1,3-thiazole-5-carboxamide Chemical compound CCNC(=O)C=1SC(N2C3=CC(OC)=C(OC)C=C3N=C2)=NC=1C1=CC=CC=C1 LSPBWHHLSDAMJA-UHFFFAOYSA-N 0.000 claims 1
- YLSWRBTYBDZDEY-UHFFFAOYSA-N 2-(5,6-dimethylbenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(C)C(C)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 YLSWRBTYBDZDEY-UHFFFAOYSA-N 0.000 claims 1
- OLHHBNBLSWJMCJ-UHFFFAOYSA-N 2-(5-chloro-6-fluorobenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC(F)=C(Cl)C=C3N=C2)=NC=1C1=CC=CC=C1 OLHHBNBLSWJMCJ-UHFFFAOYSA-N 0.000 claims 1
- RMLVXIDTNWGOGL-UHFFFAOYSA-N 2-(5-chloro-6-methylbenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=NC=2C=C(Cl)C(C)=CC=2N1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 RMLVXIDTNWGOGL-UHFFFAOYSA-N 0.000 claims 1
- SEZLKARTIWTVRA-UHFFFAOYSA-N 2-(5-chlorobenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC=C(Cl)C=C3N=C2)=NC=1C1=CC=CC=C1 SEZLKARTIWTVRA-UHFFFAOYSA-N 0.000 claims 1
- HIIZLZWFZQKXBD-UHFFFAOYSA-N 2-(5-hydroxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC=C(O)C=C3N=C2)=NC=1C1=CC=CC=C1 HIIZLZWFZQKXBD-UHFFFAOYSA-N 0.000 claims 1
- UEGUPKZLQHKAKO-UHFFFAOYSA-N 2-(5-methoxy-6-methylbenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(C)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 UEGUPKZLQHKAKO-UHFFFAOYSA-N 0.000 claims 1
- UKLMWNNCZHYWNQ-UHFFFAOYSA-N 2-(5-methylbenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=NC2=CC(C)=CC=C2N1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 UKLMWNNCZHYWNQ-UHFFFAOYSA-N 0.000 claims 1
- ZMGWBKZUFTUTEA-UHFFFAOYSA-N 2-(6-chloro-5-fluorobenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC(Cl)=C(F)C=C3N=C2)=NC=1C1=CC=CC=C1 ZMGWBKZUFTUTEA-UHFFFAOYSA-N 0.000 claims 1
- AWYDHHWUMSEDBL-UHFFFAOYSA-N 2-(6-chloro-5-methylbenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(Cl)C(C)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 AWYDHHWUMSEDBL-UHFFFAOYSA-N 0.000 claims 1
- YLWMPUZSBRYFED-UHFFFAOYSA-N 2-(6-chlorobenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC(Cl)=CC=C3N=C2)=NC=1C1=CC=CC=C1 YLWMPUZSBRYFED-UHFFFAOYSA-N 0.000 claims 1
- CPSIKNVIGBOHNF-UHFFFAOYSA-N 2-(6-hydroxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC(O)=CC=C3N=C2)=NC=1C1=CC=CC=C1 CPSIKNVIGBOHNF-UHFFFAOYSA-N 0.000 claims 1
- QLMZHYHCYBJJRB-UHFFFAOYSA-N 2-(6-methoxy-5-methylbenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=NC=2C=C(C)C(OC)=CC=2N1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 QLMZHYHCYBJJRB-UHFFFAOYSA-N 0.000 claims 1
- GQWJFQFBBZYYNC-UHFFFAOYSA-N 2-(6-methoxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C12=CC(OC)=CC=C2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 GQWJFQFBBZYYNC-UHFFFAOYSA-N 0.000 claims 1
- DMGNZHPEHRWPDM-UHFFFAOYSA-N 2-(7-hydroxybenzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=C(O)C=CC=C3N=C2)=NC=1C1=CC=CC=C1 DMGNZHPEHRWPDM-UHFFFAOYSA-N 0.000 claims 1
- HWJJDEHEYRTQDQ-UHFFFAOYSA-N 2-(8h-[1,3]dioxino[5,4-f]benzimidazol-3-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC=4OCOCC=4C=C3N=C2)=NC=1C1=CC=CC=C1 HWJJDEHEYRTQDQ-UHFFFAOYSA-N 0.000 claims 1
- RWWYSPVYHFYQEI-UHFFFAOYSA-N 2-(benzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxamide Chemical compound NC(=O)C=1SC(N2C3=CC=CC=C3N=C2)=NC=1C1=CC=CC=C1 RWWYSPVYHFYQEI-UHFFFAOYSA-N 0.000 claims 1
- NAOZLCIOJAYXIM-UHFFFAOYSA-N 2-(benzimidazol-1-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(N2C3=CC=CC=C3N=C2)=NC=1C1=CC=CC=C1 NAOZLCIOJAYXIM-UHFFFAOYSA-N 0.000 claims 1
- OCNNMZSXISRRDO-UHFFFAOYSA-N 2-[5,6-bis(2-methoxyethoxy)benzimidazol-1-yl]-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OCCOC)C(OCCOC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 OCNNMZSXISRRDO-UHFFFAOYSA-N 0.000 claims 1
- FJJJEJDFPSGPJD-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 FJJJEJDFPSGPJD-UHFFFAOYSA-N 0.000 claims 1
- BLJVEZPCIIAHTC-UHFFFAOYSA-N 2-[6-(2-methoxyethoxy)benzimidazol-1-yl]-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound C12=CC(OCCOC)=CC=C2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1 BLJVEZPCIIAHTC-UHFFFAOYSA-N 0.000 claims 1
- PQSSBTQHZHXLJL-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=C2OCOC2=CC(C=2N=C(SC=2C(O)=O)N2C=NC=3C=C(C(=CC=32)OC)OC)=C1 PQSSBTQHZHXLJL-UHFFFAOYSA-N 0.000 claims 1
- QPEXOJRZKBRJKH-UHFFFAOYSA-N 4-(2,3-difluorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(F)=C1F QPEXOJRZKBRJKH-UHFFFAOYSA-N 0.000 claims 1
- DUVUPQWKKQCZJX-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound O1CCOC2=CC(C=3N=C(SC=3C(O)=O)N3C=NC=4C=C(C(=CC=43)OC)OC)=CC=C21 DUVUPQWKKQCZJX-UHFFFAOYSA-N 0.000 claims 1
- DYUPBENDIHQGHP-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC=C1Cl DYUPBENDIHQGHP-UHFFFAOYSA-N 0.000 claims 1
- RJXKNTHXJWTEPR-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=NC(Cl)=C1 RJXKNTHXJWTEPR-UHFFFAOYSA-N 0.000 claims 1
- SCOSEDVZPKPHRX-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=C(Cl)C(Cl)=C1 SCOSEDVZPKPHRX-UHFFFAOYSA-N 0.000 claims 1
- IYURKULQMRYAKQ-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=C(F)C(F)=C1 IYURKULQMRYAKQ-UHFFFAOYSA-N 0.000 claims 1
- CQYNRUIRNCHZLX-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC(Cl)=CC(Cl)=C1 CQYNRUIRNCHZLX-UHFFFAOYSA-N 0.000 claims 1
- RZOBVBIFDPMOFZ-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(Br)=C1 RZOBVBIFDPMOFZ-UHFFFAOYSA-N 0.000 claims 1
- KJGWLFPZPBTTJR-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=C(F)C(Cl)=C1 KJGWLFPZPBTTJR-UHFFFAOYSA-N 0.000 claims 1
- GXSMRZKLEMBKNV-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=NC=1C1=CC=CC(Cl)=C1 GXSMRZKLEMBKNV-UHFFFAOYSA-N 0.000 claims 1
- ASNYTHITDPHAHV-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=CC(Cl)=C1 ASNYTHITDPHAHV-UHFFFAOYSA-N 0.000 claims 1
- WLCMCUNZFGPDHY-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-n'-(3-methylbenzoyl)-1,3-thiazole-5-carbohydrazide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(S1)=NC(C=2C=C(Cl)C=CC=2)=C1C(=O)NNC(=O)C1=CC=CC(C)=C1 WLCMCUNZFGPDHY-UHFFFAOYSA-N 0.000 claims 1
- UULRFUVGBICGFR-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-n'-(thiophene-2-carbonyl)-1,3-thiazole-5-carbohydrazide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(S1)=NC(C=2C=C(Cl)C=CC=2)=C1C(=O)NNC(=O)C1=CC=CS1 UULRFUVGBICGFR-UHFFFAOYSA-N 0.000 claims 1
- NSPIHQBVBFUKPO-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-n-(1,3-thiazol-2-yl)-1,3-thiazole-5-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(S1)=NC(C=2C=C(Cl)C=CC=2)=C1C(=O)NC1=NC=CS1 NSPIHQBVBFUKPO-UHFFFAOYSA-N 0.000 claims 1
- IZKBUAOQZIQDIC-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-n-(3-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC(NC(=O)C2=C(N=C(S2)N2C3=CC(OC)=C(OC)C=C3N=C2)C=2C=C(Cl)C=CC=2)=C1 IZKBUAOQZIQDIC-UHFFFAOYSA-N 0.000 claims 1
- RJWVHJYICRWXSB-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(5,6-dimethoxybenzimidazol-1-yl)-n-pyrimidin-4-yl-1,3-thiazole-5-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(S1)=NC(C=2C=C(Cl)C=CC=2)=C1C(=O)NC1=CC=NC=N1 RJWVHJYICRWXSB-UHFFFAOYSA-N 0.000 claims 1
- HRMKXYQQUFLXCO-UHFFFAOYSA-N 4-[3-chloro-4-(trifluoromethyl)phenyl]-2-(5,6-dimethoxybenzimidazol-1-yl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(O)=O)=NC=1C1=CC=C(C(F)(F)F)C(Cl)=C1 HRMKXYQQUFLXCO-UHFFFAOYSA-N 0.000 claims 1
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77696406P | 2006-02-27 | 2006-02-27 | |
| US60/776,964 | 2006-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008138163A true RU2008138163A (ru) | 2010-04-10 |
Family
ID=38051896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008138163/04A RU2008138163A (ru) | 2006-02-27 | 2007-02-19 | 4-фенилтиазол-5-карбоновые кислоты и амиды 4-фенилтиазол-5-карбоновой кислоты как ингибиторы polo-подобной киназы plk1 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7504513B2 (https=) |
| EP (1) | EP1991543A1 (https=) |
| JP (1) | JP2009528284A (https=) |
| KR (1) | KR101060539B1 (https=) |
| CN (1) | CN101415704A (https=) |
| AR (1) | AR059621A1 (https=) |
| AU (1) | AU2007217575A1 (https=) |
| BR (1) | BRPI0710473A2 (https=) |
| CA (1) | CA2642921A1 (https=) |
| CR (1) | CR10206A (https=) |
| EC (1) | ECSP088700A (https=) |
| IL (1) | IL193481A0 (https=) |
| MA (1) | MA30260B1 (https=) |
| MX (1) | MX2008010884A (https=) |
| NO (1) | NO20083708L (https=) |
| RU (1) | RU2008138163A (https=) |
| TW (1) | TW200745097A (https=) |
| WO (1) | WO2007096315A1 (https=) |
| ZA (1) | ZA200807074B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5246158B2 (ja) * | 2007-06-08 | 2013-07-24 | 日本電気株式会社 | 半導体集積回路及びフィルタ制御方法 |
| JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | チオフェンおよびホスファチジルイノシトール３−キナーゼ（ｐｉ３ｋ）阻害薬としてのその使用 |
| KR101707669B1 (ko) * | 2008-04-17 | 2017-02-16 | 더 존스 홉킨스 유니버시티 | 약제-내성 종양에서 화학요법제 활성을 증강시키는 ｏｎ01910.ｎａ |
| EA016789B1 (ru) * | 2008-09-10 | 2012-07-30 | Дейталейз Лтд. | Среда для хранения данных |
| WO2010077295A1 (en) * | 2008-12-09 | 2010-07-08 | King Faisal Specialist Hospital & Research Centre | Substituted tricyclic heterocycles and uses to treat tumors and proliferative disorders |
| CA2745596A1 (en) | 2008-12-18 | 2010-10-28 | F. Hoffmann-La Roche Ag | Thiazolyl-benzimidazoles |
| WO2010090716A1 (en) * | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US9090601B2 (en) * | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| US8859768B2 (en) | 2010-08-11 | 2014-10-14 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| MX2013001660A (es) | 2010-08-11 | 2013-06-03 | Millenium Pharmaceuticals Inc | Heteroarilos y usos de los mismos. |
| TW201307309A (zh) | 2010-10-13 | 2013-02-16 | Millennium Pharm Inc | 雜芳基化合物及其用途 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322429A (en) * | 1980-09-16 | 1982-03-30 | Eli Lilly And Company | Isoxazolylbenzamides as insecticides |
| US4818270A (en) * | 1986-08-28 | 1989-04-04 | Monsanto Company | 2-(Heteroamino)-4,5-substituted-oxazole/thiazole compounds as herbicide antidotes, compositions and use |
| US6194447B1 (en) * | 1998-07-02 | 2001-02-27 | Neurosearch A/S | Bis (benzimidazole) derivatives serving as potassium blocking agents |
| ES2349762T3 (es) | 2000-08-10 | 2011-01-11 | Pfizer Italia S.R.L. | Biciclo-pirazoles activos como inhibidores de quinasas, procedimientos para su preparación y composiciones farmacéuticas que los comprenden. |
| GB0102687D0 (en) | 2001-02-02 | 2001-03-21 | Pharmacia & Upjohn Spa | Oxazolyl-pyrazole derivatives active as kinase inhibitors,process for their preparation and pharmaceutical compositions comprising them |
| WO2003070283A2 (en) | 2002-02-22 | 2003-08-28 | Klaus Strebhardt | Agent for inhibiting development or progress of proliferative diseases and especially cancer diseases and pharmaceutical composition containing said agent |
| EP1486490A1 (en) * | 2002-02-28 | 2004-12-15 | Takeda Chemical Industries, Ltd. | Azole compounds |
| JP2003321460A (ja) * | 2002-02-28 | 2003-11-11 | Takeda Chem Ind Ltd | アゾール化合物 |
| NZ535232A (en) | 2002-02-28 | 2007-05-31 | Univ Temple | Amino-substituted (E)-2,6-dialkoxystyryl 4-substituted benzylsulfones for treating proliferative disorders |
| JP2005538048A (ja) | 2002-05-03 | 2005-12-15 | シエーリング アクチエンゲゼルシャフト | チアゾリジノン類、それらの生成及び医薬剤としての使用 |
| US6906186B1 (en) | 2002-07-30 | 2005-06-14 | Isis Pharmaceuticals, Inc. | Antisense modulation of polo-like kinase expression |
| MXPA05001544A (es) * | 2002-08-08 | 2005-04-19 | Smithkline Beecham Corp | Compuestos de tiofeno. |
| AU2003284399A1 (en) | 2002-11-14 | 2004-06-03 | Kyowa Hakko Kogyo Co., Ltd. | Plk inhibitors |
| US20050196808A1 (en) | 2002-11-14 | 2005-09-08 | Yaffe Michael B. | Products and processes for modulating peptide-peptide binding domain interactions |
| JP3837670B2 (ja) | 2002-12-12 | 2006-10-25 | 富士通株式会社 | データ中継装置、連想メモリデバイス、および連想メモリデバイス利用情報検索方法 |
| GB0302220D0 (en) | 2003-01-30 | 2003-03-05 | Cyclacel Ltd | Use |
| ES2325440T3 (es) | 2003-02-20 | 2009-09-04 | Smithkline Beecham Corporation | Compuestos de pirimidina. |
| US7462614B2 (en) | 2003-04-01 | 2008-12-09 | Smithkline Beecham Corporation | Imidazotriazine compounds |
| DK1641780T3 (da) | 2003-06-24 | 2009-02-02 | Pfizer Prod Inc | Fremgangsmåder til fremstilling af 1-[(benzimidazol-1yl)quinolin-8-yl]-piperidin-4-ylamin-derivater |
| WO2005019193A2 (en) | 2003-08-20 | 2005-03-03 | Smithkline Beecham Corporation | Phenylurea derivatives useful in the treatment of conditions mediated by polo-like kinases (plk) |
| CA2542880A1 (en) | 2003-10-21 | 2005-05-12 | Cyclacel Limited | Pyrimidin-4-yl-3, 4-thione compounds and their use in therapy |
| DE10351744A1 (de) | 2003-10-31 | 2005-06-16 | Schering Ag | Thiazolidinone, deren Herstellung und Verwendung als Arzneimittel |
| EP1711496A4 (en) | 2004-01-28 | 2009-02-11 | Smithkline Beecham Corp | THIAZOLE COMPOUNDS |
-
2007
- 2007-02-07 US US11/703,306 patent/US7504513B2/en not_active Expired - Fee Related
- 2007-02-19 CA CA002642921A patent/CA2642921A1/en not_active Abandoned
- 2007-02-19 BR BRPI0710473-1A patent/BRPI0710473A2/pt not_active IP Right Cessation
- 2007-02-19 RU RU2008138163/04A patent/RU2008138163A/ru not_active Application Discontinuation
- 2007-02-19 KR KR1020087021067A patent/KR101060539B1/ko not_active Expired - Fee Related
- 2007-02-19 MX MX2008010884A patent/MX2008010884A/es not_active Application Discontinuation
- 2007-02-19 AU AU2007217575A patent/AU2007217575A1/en not_active Abandoned
- 2007-02-19 EP EP07712233A patent/EP1991543A1/en not_active Withdrawn
- 2007-02-19 CN CNA2007800068055A patent/CN101415704A/zh active Pending
- 2007-02-19 WO PCT/EP2007/051541 patent/WO2007096315A1/en not_active Ceased
- 2007-02-19 JP JP2008555763A patent/JP2009528284A/ja active Pending
- 2007-02-23 AR ARP070100768A patent/AR059621A1/es unknown
- 2007-02-26 TW TW096106341A patent/TW200745097A/zh unknown
-
2008
- 2008-08-14 IL IL193481A patent/IL193481A0/en unknown
- 2008-08-14 CR CR10206A patent/CR10206A/es not_active Application Discontinuation
- 2008-08-15 ZA ZA200807074A patent/ZA200807074B/xx unknown
- 2008-08-26 EC EC2008008700A patent/ECSP088700A/es unknown
- 2008-08-28 NO NO20083708A patent/NO20083708L/no not_active Application Discontinuation
- 2008-09-04 MA MA31208A patent/MA30260B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007217575A1 (en) | 2007-08-30 |
| KR101060539B1 (ko) | 2011-08-30 |
| CN101415704A (zh) | 2009-04-22 |
| CR10206A (es) | 2008-09-22 |
| WO2007096315A1 (en) | 2007-08-30 |
| ECSP088700A (es) | 2008-09-29 |
| CA2642921A1 (en) | 2007-08-30 |
| US7504513B2 (en) | 2009-03-17 |
| TW200745097A (en) | 2007-12-16 |
| NO20083708L (no) | 2008-09-23 |
| MX2008010884A (es) | 2008-09-03 |
| US20070203210A1 (en) | 2007-08-30 |
| EP1991543A1 (en) | 2008-11-19 |
| IL193481A0 (en) | 2009-05-04 |
| AR059621A1 (es) | 2008-04-16 |
| MA30260B1 (fr) | 2009-03-02 |
| JP2009528284A (ja) | 2009-08-06 |
| ZA200807074B (en) | 2009-10-28 |
| BRPI0710473A2 (pt) | 2011-08-16 |
| KR20080090550A (ko) | 2008-10-08 |
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| FA93 | Acknowledgement of application withdrawn (no request for examination) |
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