MXPA05008612A - Compuestos novedosos. - Google Patents

Info

Publication number

MXPA05008612A

MXPA05008612A MXPA05008612A MXPA05008612A MXPA05008612A MX PA05008612 A MXPA05008612 A MX PA05008612A MX PA05008612 A MXPA05008612 A MX PA05008612A MX PA05008612 A MXPA05008612 A MX PA05008612A MX PA05008612 A MXPA05008612 A MX PA05008612A

Authority

MX

Mexico

Prior art keywords

alkyl

optionally substituted

cr10r2o

compound according

further characterized

Prior art date

2003-02-14

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 283
• -1 1,5,7-trisubstituted quinoline-2(1H)-one compounds Chemical class 0.000 claims abstract description 76
• 201000010099 disease Diseases 0.000 claims abstract description 61
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 61
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 48
• 102100023482 Mitogen-activated protein kinase 14 Human genes 0.000 claims abstract description 42
• 108010084680 Heterogeneous-Nuclear Ribonucleoprotein K Proteins 0.000 claims abstract description 36
• 230000001404 mediated effect Effects 0.000 claims abstract description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 163
• 229910052739 hydrogen Inorganic materials 0.000 claims description 112
• 239000001257 hydrogen Substances 0.000 claims description 90
• 125000001072 heteroaryl group Chemical group 0.000 claims description 67
• 150000002431 hydrogen Chemical group 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 53
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 51
• 238000011282 treatment Methods 0.000 claims description 50
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 47
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 41
• 150000002367 halogens Chemical group 0.000 claims description 40
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 38
• 238000006243 chemical reaction Methods 0.000 claims description 36
• 241000124008 Mammalia Species 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 241000700605 Viruses Species 0.000 claims description 25
• 125000003107 substituted aryl group Chemical group 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 241000430519 Human rhinovirus sp. Species 0.000 claims description 19
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
• 206010040070 Septic Shock Diseases 0.000 claims description 18
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 241000709661 Enterovirus Species 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
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• 239000003814 drug Substances 0.000 claims description 12
• 125000001188 haloalkyl group Chemical group 0.000 claims description 12
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• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
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• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
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• 241000725643 Respiratory syncytial virus Species 0.000 claims description 8
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• 239000003085 diluting agent Substances 0.000 claims description 8
• 206010022000 influenza Diseases 0.000 claims description 8
• 241000712461 unidentified influenza virus Species 0.000 claims description 8
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
• AHCYGXRBOJTSOA-UHFFFAOYSA-N 7-bromo-1,5-bis(2-chlorophenyl)-1,6-naphthyridin-2-one Chemical compound ClC1=CC=CC=C1C1=NC(Br)=CC2=C1C=CC(=O)N2C1=CC=CC=C1Cl AHCYGXRBOJTSOA-UHFFFAOYSA-N 0.000 claims description 7
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• 241000711573 Coronaviridae Species 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 208000002606 Paramyxoviridae Infections Diseases 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
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• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 206010010741 Conjunctivitis Diseases 0.000 claims description 5
• 208000011231 Crohn disease Diseases 0.000 claims description 5
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• 206010018364 Glomerulonephritis Diseases 0.000 claims description 5
• 206010018634 Gouty Arthritis Diseases 0.000 claims description 5
• 208000032456 Hemorrhagic Shock Diseases 0.000 claims description 5
• 201000009906 Meningitis Diseases 0.000 claims description 5
• 206010027476 Metastases Diseases 0.000 claims description 5
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 5
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• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• 230000002491 angiogenic effect Effects 0.000 claims description 5
• 208000010668 atopic eczema Diseases 0.000 claims description 5
• 206010006451 bronchitis Diseases 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 208000007451 chronic bronchitis Diseases 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 230000000302 ischemic effect Effects 0.000 claims description 5
• 230000009401 metastasis Effects 0.000 claims description 5
• 208000002574 reactive arthritis Diseases 0.000 claims description 5
• 201000005404 rubella Diseases 0.000 claims description 5
• 230000036303 septic shock Effects 0.000 claims description 5
• 201000004595 synovitis Diseases 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• NCVGTRDMXZGULL-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-(4-methylphenyl)quinolin-2-one Chemical compound C1=CC(C)=CC=C1C1=CC=CC2=C1C=CC(=O)N2C1=CC=C(F)C=C1 NCVGTRDMXZGULL-UHFFFAOYSA-N 0.000 claims description 4
• ZQKMVHXJWJNEQG-UHFFFAOYSA-N 1h-1,6-naphthyridin-2-one Chemical compound C1=NC=CC2=NC(O)=CC=C21 ZQKMVHXJWJNEQG-UHFFFAOYSA-N 0.000 claims description 4
• ZFRUGZMCGCYBRC-UHFFFAOYSA-N 1h-1,8-naphthyridin-2-one Chemical compound C1=CC=NC2=NC(O)=CC=C21 ZFRUGZMCGCYBRC-UHFFFAOYSA-N 0.000 claims description 4
• ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 4
• LIYRXUGPUPJBLG-UHFFFAOYSA-N 5-(2,4-difluorophenyl)-1-(4-fluorophenyl)quinolin-2-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C=CC2=C(C=3C(=CC(F)=CC=3)F)C=CC=C21 LIYRXUGPUPJBLG-UHFFFAOYSA-N 0.000 claims description 4
• 208000035143 Bacterial infection Diseases 0.000 claims description 4
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• 206010019280 Heart failures Diseases 0.000 claims description 4
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• 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
• 230000002490 cerebral effect Effects 0.000 claims description 4
• 208000020832 chronic kidney disease Diseases 0.000 claims description 4
• 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 4
• 210000004351 coronary vessel Anatomy 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 230000004770 neurodegeneration Effects 0.000 claims description 4
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• 238000001356 surgical procedure Methods 0.000 claims description 4
• 230000004614 tumor growth Effects 0.000 claims description 4
• PYQCKLNGCQVGFP-UHFFFAOYSA-N 1,5-bis(2-chlorophenyl)-7-(1,3-dihydroxypropan-2-ylamino)-1,6-naphthyridin-2-one Chemical compound O=C1C=CC=2C(C=3C(=CC=CC=3)Cl)=NC(NC(CO)CO)=CC=2N1C1=CC=CC=C1Cl PYQCKLNGCQVGFP-UHFFFAOYSA-N 0.000 claims description 3
• GMZQTGQJWIBEEA-UHFFFAOYSA-N 1,5-bis(4-fluorophenyl)-1,8-naphthyridin-2-one Chemical compound C1=CC(F)=CC=C1C1=CC=NC2=C1C=CC(=O)N2C1=CC=C(F)C=C1 GMZQTGQJWIBEEA-UHFFFAOYSA-N 0.000 claims description 3
• FGRCFQSRHJPOOF-UHFFFAOYSA-N 1,5-bis(4-fluorophenyl)quinolin-2-one Chemical compound C1=CC(F)=CC=C1C1=CC=CC2=C1C=CC(=O)N2C1=CC=C(F)C=C1 FGRCFQSRHJPOOF-UHFFFAOYSA-N 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• YGRYGQKVGGEPER-UHFFFAOYSA-N 5-(2,4-difluorophenyl)-1-(4-fluorophenyl)-1,8-naphthyridin-2-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C=CC2=C(C=3C(=CC(F)=CC=3)F)C=CN=C21 YGRYGQKVGGEPER-UHFFFAOYSA-N 0.000 claims description 3
• WGRXIIODSLLFHX-UHFFFAOYSA-N 5-(2-fluorophenyl)-1-(4-fluorophenyl)quinolin-2-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C=CC2=C(C=3C(=CC=CC=3)F)C=CC=C21 WGRXIIODSLLFHX-UHFFFAOYSA-N 0.000 claims description 3
• APKKZTGSYROVPP-UHFFFAOYSA-N 5-phenyl-1h-1,6-naphthyridin-2-one Chemical compound N1=CC=C2NC(=O)C=CC2=C1C1=CC=CC=C1 APKKZTGSYROVPP-UHFFFAOYSA-N 0.000 claims description 3
• OZRPUNDRYYIJFC-UHFFFAOYSA-N 6-bromo-1,5-bis(2-chlorophenyl)-7-methoxyquinolin-2-one Chemical compound O=C1C=CC=2C(C=3C(=CC=CC=3)Cl)=C(Br)C(OC)=CC=2N1C1=CC=CC=C1Cl OZRPUNDRYYIJFC-UHFFFAOYSA-N 0.000 claims description 3
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• RBYQNKUAGUQDAA-UHFFFAOYSA-N 1,5-bis(2-chlorophenyl)-7-(1h-imidazol-2-ylmethylamino)-1,6-naphthyridin-2-one Chemical compound ClC1=CC=CC=C1C1=NC(NCC=2NC=CN=2)=CC2=C1C=CC(=O)N2C1=CC=CC=C1Cl RBYQNKUAGUQDAA-UHFFFAOYSA-N 0.000 claims description 2
• UTEMMEATFDOJTF-UHFFFAOYSA-N 1,5-bis(2-chlorophenyl)-7-[2-(propan-2-ylamino)ethylamino]-1,6-naphthyridin-2-one Chemical compound O=C1C=CC=2C(C=3C(=CC=CC=3)Cl)=NC(NCCNC(C)C)=CC=2N1C1=CC=CC=C1Cl UTEMMEATFDOJTF-UHFFFAOYSA-N 0.000 claims description 2
• PIOGKVWSMAZIFA-UHFFFAOYSA-N 1-methyl-5-phenyl-1,6-naphthyridin-2-one Chemical compound C=12C=CC(=O)N(C)C2=CC=NC=1C1=CC=CC=C1 PIOGKVWSMAZIFA-UHFFFAOYSA-N 0.000 claims description 2
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