PT2013175T - Inibidores de map-quinase p38 - Google Patents

Info

Publication number

PT2013175T

PT2013175T PT77326296T PT07732629T PT2013175T PT 2013175 T PT2013175 T PT 2013175T PT 77326296 T PT77326296 T PT 77326296T PT 07732629 T PT07732629 T PT 07732629T PT 2013175 T PT2013175 T PT 2013175T

Authority

PT

Portugal

Prior art keywords

amino

alkyl

phenyl

hydrogen

cyclopentyl

Prior art date

2006-05-04

Links

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• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title description 31
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 title description 31
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title description 2
• -1 bicyclic heterocyclic radical Chemical class 0.000 claims description 166
• 150000001875 compounds Chemical class 0.000 claims description 87
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 239000001257 hydrogen Substances 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 150000003254 radicals Chemical class 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 229940024606 amino acid Drugs 0.000 claims description 28
• 150000002148 esters Chemical class 0.000 claims description 27
• 235000001014 amino acid Nutrition 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• 150000001413 amino acids Chemical class 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 108010051152 Carboxylesterase Proteins 0.000 claims description 14
• 102000013392 Carboxylesterase Human genes 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 125000006413 ring segment Chemical group 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 230000003834 intracellular effect Effects 0.000 claims description 13
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• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 229910052705 radium Chemical group 0.000 claims description 11
• 229910052701 rubidium Chemical group 0.000 claims description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000004185 ester group Chemical group 0.000 claims description 10
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 10
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
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• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
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• 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims description 8
• 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 8
• 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 8
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
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• 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 7
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• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
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• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 5
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 5
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• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 5
• QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 5
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 5
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 5
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• QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 5
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 5
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