HRP20010524A2 - Benzoheterocycles and their use as mek inhibitors - Google Patents

Info

Publication number

HRP20010524A2

HRP20010524A2 HR20010524A HRP20010524A HRP20010524A2 HR P20010524 A2 HRP20010524 A2 HR P20010524A2 HR 20010524 A HR20010524 A HR 20010524A HR P20010524 A HRP20010524 A HR P20010524A HR P20010524 A2 HRP20010524 A2 HR P20010524A2

Authority

HR

Croatia

Prior art keywords

methyl

compound

alkyl

phenylamino

phenyl

Prior art date

1999-01-13

Links

• Espacenet
• Global Dossier
• Discuss

• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title description 4
• -1 heterocyclic radical Chemical class 0.000 claims description 271
• 150000001875 compounds Chemical class 0.000 claims description 120
• 238000002360 preparation method Methods 0.000 claims description 99
• 238000000034 method Methods 0.000 claims description 57
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• 125000003342 alkenyl group Chemical group 0.000 claims description 30
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 24
• 238000011282 treatment Methods 0.000 claims description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
• 150000002148 esters Chemical class 0.000 claims description 19
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
• 239000000460 chlorine Chemical group 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical group 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
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• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
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• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
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• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• JENDHVLUGWDXEE-UHFFFAOYSA-N 7-fluoro-6-(4-iodo-2-methylanilino)-1,3-benzothiazole-5-carboxylic acid Chemical compound CC1=CC(I)=CC=C1NC(C(=C1)C(O)=O)=C(F)C2=C1N=CS2 JENDHVLUGWDXEE-UHFFFAOYSA-N 0.000 claims description 6
• NTZGEBNJRQSICS-UHFFFAOYSA-N 7-fluoro-6-(4-iodo-2-methylanilino)-1,3-benzoxazole-5-carboxylic acid Chemical compound CC1=CC(I)=CC=C1NC(C(=C1)C(O)=O)=C(F)C2=C1N=CO2 NTZGEBNJRQSICS-UHFFFAOYSA-N 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
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• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 5
• GFCWICPCSIPKGG-UHFFFAOYSA-N 7-fluoro-6-(4-iodo-2-methylanilino)-2h-benzotriazole-5-carboxylic acid Chemical compound CC1=CC(I)=CC=C1NC(C(=C1)C(O)=O)=C(F)C2=C1N=NN2 GFCWICPCSIPKGG-UHFFFAOYSA-N 0.000 claims description 5
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• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• WULDESHELSRYQZ-UHFFFAOYSA-N 4-fluoro-5-(4-iodo-2-methylanilino)-2,1,3-benzothiadiazole-6-carboxylic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C2=NSN=C2C=C1C(O)=O WULDESHELSRYQZ-UHFFFAOYSA-N 0.000 claims description 4
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• 208000024891 symptom Diseases 0.000 claims description 4
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 3
• YKRYPAQULJMUDV-UHFFFAOYSA-N 4-fluoro-5-(4-iodo-2-methylanilino)-2,1,3-benzoxadiazole-6-carboxylic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C2=NON=C2C=C1C(O)=O YKRYPAQULJMUDV-UHFFFAOYSA-N 0.000 claims description 3
• JWAWKFXZGAKZEU-UHFFFAOYSA-N 8-fluoro-7-(4-iodo-2-methylanilino)quinoxaline-6-carboxylic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C2=NC=CN=C2C=C1C(O)=O JWAWKFXZGAKZEU-UHFFFAOYSA-N 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Chemical group 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 210000000056 organ Anatomy 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 238000001959 radiotherapy Methods 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• ZXDUEQMOCGOOEX-UHFFFAOYSA-N 1-acetyl-7-fluoro-6-(4-iodo-2-methylanilino)benzimidazole-5-carboxylic acid Chemical compound FC1=C2N(C(=O)C)C=NC2=CC(C(O)=O)=C1NC1=CC=C(I)C=C1C ZXDUEQMOCGOOEX-UHFFFAOYSA-N 0.000 claims description 2
• UXILCSZNSIYGAV-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-7-fluoro-6-(4-iodo-2-methylanilino)-3h-benzimidazole-5-carboxylic acid Chemical compound FC1=C2NC(CCN(C)C)=NC2=CC(C(O)=O)=C1NC1=CC=C(I)C=C1C UXILCSZNSIYGAV-UHFFFAOYSA-N 0.000 claims description 2
• RPZALGIZXFACEO-UHFFFAOYSA-N 7-fluoro-2-(2-hydroxyethyl)-6-(4-iodo-2-methylanilino)-3h-benzimidazole-5-carboxylic acid Chemical compound CC1=CC(I)=CC=C1NC(C(=C1)C(O)=O)=C(F)C2=C1N=C(CCO)N2 RPZALGIZXFACEO-UHFFFAOYSA-N 0.000 claims description 2
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