BRPI0711357A2 - derivados de 2-piridona para o tratamento de doença ou condição em que a inibição da atividade de neutrófilo elastase humana é benéfica - Google Patents

Info

Publication number

BRPI0711357A2

BRPI0711357A2 BRPI0711357-9A BRPI0711357A BRPI0711357A2 BR PI0711357 A2 BRPI0711357 A2 BR PI0711357A2 BR PI0711357 A BRPI0711357 A BR PI0711357A BR PI0711357 A2 BRPI0711357 A2 BR PI0711357A2

Authority

BR

Brazil

Prior art keywords

alkyl

compound

formula

phenyl

ring

Prior art date

2006-05-08

Links

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• 238000011282 treatment Methods 0.000 title claims abstract description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 26
• 201000010099 disease Diseases 0.000 title claims abstract description 21
• 230000000694 effects Effects 0.000 title claims abstract description 13
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title claims abstract description 9
• 230000009286 beneficial effect Effects 0.000 title claims abstract description 8
• 230000005764 inhibitory process Effects 0.000 title claims abstract description 6
• 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 title abstract description 12
• 102000052502 human ELANE Human genes 0.000 title abstract description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 136
• 150000003839 salts Chemical class 0.000 claims abstract description 73
• 238000000034 method Methods 0.000 claims abstract description 39
• 238000002360 preparation method Methods 0.000 claims abstract description 18
• 230000008569 process Effects 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 9
• -1 nitro, methylcarbonyl Chemical group 0.000 claims description 75
• 125000001424 substituent group Chemical group 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 229910052760 oxygen Inorganic materials 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• 125000001153 fluoro group Chemical group F* 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
• 239000000460 chlorine Substances 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 239000001301 oxygen Chemical group 0.000 claims description 19
• 229910052801 chlorine Inorganic materials 0.000 claims description 18
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 229910052717 sulfur Chemical group 0.000 claims description 17
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 15
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• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 206010006451 bronchitis Diseases 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
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• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
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• 125000001589 carboacyl group Chemical group 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
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• 125000004429 atom Chemical group 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
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• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
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• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
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• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
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• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• FIPRLUJRFYCLOZ-UHFFFAOYSA-N CC1=C(C=CC(=O)N1C2=CC=CC(=C2)C(F)(F)F)C3=CC=NN3C4=CC=C(C=C4)Cl Chemical compound CC1=C(C=CC(=O)N1C2=CC=CC(=C2)C(F)(F)F)C3=CC=NN3C4=CC=C(C=C4)Cl FIPRLUJRFYCLOZ-UHFFFAOYSA-N 0.000 claims description 3
• 108010028275 Leukocyte Elastase Proteins 0.000 claims description 3
• 102000016799 Leukocyte elastase Human genes 0.000 claims description 3
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• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
• IEBVEDCUPNCJEX-UHFFFAOYSA-N CC1=C(C=CC(=O)N1C2=CC=CC(=C2)C(F)(F)F)C3=CC=NN3C4=CC=C(C=C4)F Chemical compound CC1=C(C=CC(=O)N1C2=CC=CC(=C2)C(F)(F)F)C3=CC=NN3C4=CC=C(C=C4)F IEBVEDCUPNCJEX-UHFFFAOYSA-N 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims description 2
• 239000012038 nucleophile Substances 0.000 claims description 2
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• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
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