BRPI0919329A2 - Derivados de pirazolo piridina, composições farmacêuticas e métodos associados - Google Patents

Info

Publication number

BRPI0919329A2

BRPI0919329A2 BRPI0919329-4A BRPI0919329A BRPI0919329A2 BR PI0919329 A2 BRPI0919329 A2 BR PI0919329A2 BR PI0919329 A BRPI0919329 A BR PI0919329A BR PI0919329 A2 BRPI0919329 A2 BR PI0919329A2

Authority

BR

Brazil

Prior art keywords

optionally substituted

alkyl

heteroaryl

diseases

aryl

Prior art date

2008-09-23

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 46
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 98
• 201000010099 disease Diseases 0.000 claims abstract description 62
• QUYPSOKUBYENRV-UHFFFAOYSA-N 1h-pyrazole;pyridine Chemical class C=1C=NNC=1.C1=CC=NC=C1 QUYPSOKUBYENRV-UHFFFAOYSA-N 0.000 claims abstract description 50
• 108010002998 NADPH Oxidases Proteins 0.000 claims abstract description 37
• 102000004722 NADPH Oxidases Human genes 0.000 claims abstract description 37
• 238000011282 treatment Methods 0.000 claims abstract description 26
• 101000968308 Homo sapiens Dual oxidase 1 Proteins 0.000 claims abstract description 11
• 101000968305 Homo sapiens Dual oxidase 2 Proteins 0.000 claims abstract description 11
• 102100021217 Dual oxidase 2 Human genes 0.000 claims abstract description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 125
• -1 1-acetyl-4-methyl-2-phenyl-5- (pyridin-3-ylmethyl) -1H-pyrazole Chemical compound 0.000 claims description 99
• 125000001072 heteroaryl group Chemical group 0.000 claims description 58
• 206010028980 Neoplasm Diseases 0.000 claims description 51
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 47
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 44
• 230000033115 angiogenesis Effects 0.000 claims description 43
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 32
• 150000001336 alkenes Chemical class 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• 201000011510 cancer Diseases 0.000 claims description 22
• 208000023504 respiratory system disease Diseases 0.000 claims description 21
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 18
• 125000003107 substituted aryl group Chemical group 0.000 claims description 18
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
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• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
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• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 7
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• 125000005275 alkylenearyl group Chemical group 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
• 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
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• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
• TXGNEJCHHBLABF-UHFFFAOYSA-N 1-(2-methoxyacetyl)-4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(CC=3C=NC=CC=3)C(=O)C=C2N(C(=O)COC)N1C1=CC=CC=C1 TXGNEJCHHBLABF-UHFFFAOYSA-N 0.000 claims description 2
• ZTLRXINOMBWBNW-UHFFFAOYSA-N 1-acetyl-2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(CC=3N=CC=CC=3)C(=O)C=C2N(C(=O)C)N1C1=CC=CC=C1Cl ZTLRXINOMBWBNW-UHFFFAOYSA-N 0.000 claims description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
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• IZSRLBYQBSHEJS-UHFFFAOYSA-N 1-acetyl-4-methyl-2-(2-methylphenyl)-5-(pyridin-2-ylmethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(CC=3N=CC=CC=3)C(=O)C=C2N(C(=O)C)N1C1=CC=CC=C1C IZSRLBYQBSHEJS-UHFFFAOYSA-N 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• MKCUYCJSATYBJL-UHFFFAOYSA-N 4-methyl-1-(4-phenoxybutanoyl)-2-phenyl-5-(pyridin-3-ylmethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(C(=O)CCCOC=3C=CC=CC=3)N(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CN=C1 MKCUYCJSATYBJL-UHFFFAOYSA-N 0.000 claims 1
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
• ICZVBOAABXHPSZ-UHFFFAOYSA-N piperidine-2,5-dione Chemical compound O=C1CCC(=O)NC1 ICZVBOAABXHPSZ-UHFFFAOYSA-N 0.000 claims 1
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000000243 solution Substances 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• 239000000543 intermediate Substances 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 11
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• 102100021218 Dual oxidase 1 Human genes 0.000 description 9
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