ES2292812T3 - 2-fenil benzimidazol e imidazo-(4,5)-piridinas como inhibidores de cds1/chk2 y coadyuvantes para quimioterapia o radioterapia en el tratamiento del cancer. - Google Patents

Info

Publication number

ES2292812T3

ES2292812T3 ES02770620T ES02770620T ES2292812T3 ES 2292812 T3 ES2292812 T3 ES 2292812T3 ES 02770620 T ES02770620 T ES 02770620T ES 02770620 T ES02770620 T ES 02770620T ES 2292812 T3 ES2292812 T3 ES 2292812T3

Authority

ES

Spain

Prior art keywords

phenyl

chloro

compound

carboxylic acid

acid amide

Prior art date

2001-10-19

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 238000011282 treatment Methods 0.000 title claims abstract description 31
• 201000011510 cancer Diseases 0.000 title claims abstract description 27
• 239000003112 inhibitor Substances 0.000 title abstract description 13
• 238000002512 chemotherapy Methods 0.000 title abstract description 3
• 238000001959 radiotherapy Methods 0.000 title abstract description 3
• 102100031075 Serine/threonine-protein kinase Chk2 Human genes 0.000 title description 3
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 2
• 101000777277 Homo sapiens Serine/threonine-protein kinase Chk2 Proteins 0.000 title description 2
• 101710178747 Phosphatidate cytidylyltransferase 1 Proteins 0.000 title 1
• -1 piperazino-diyl Chemical group 0.000 claims description 300
• 150000001875 compounds Chemical class 0.000 claims description 217
• 229910052799 carbon Inorganic materials 0.000 claims description 42
• 150000003254 radicals Chemical class 0.000 claims description 28
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 150000001408 amides Chemical class 0.000 claims description 22
• 150000001721 carbon Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000004429 atom Chemical group 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 229930195733 hydrocarbon Natural products 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 150000002148 esters Chemical class 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 239000004215 Carbon black (E152) Substances 0.000 claims description 10
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000002950 monocyclic group Chemical group 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
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• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
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• 239000003814 drug Substances 0.000 claims description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
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• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
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• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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• QHGFZMGCLAYOHF-UHFFFAOYSA-N 2-[6-[(3,4-dichlorophenyl)sulfamoyl]pyridin-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=N1)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 QHGFZMGCLAYOHF-UHFFFAOYSA-N 0.000 claims description 2
• XSOGJFDKBPOUFB-UHFFFAOYSA-N 2-[6-[(4-chlorophenyl)sulfonylamino]pyridin-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=N1)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 XSOGJFDKBPOUFB-UHFFFAOYSA-N 0.000 claims description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
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• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
• 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
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• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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