MXPA06003578A - Compuestos de quinoxalina. - Google Patents

Info

Publication number

MXPA06003578A

MXPA06003578A MXPA06003578A MXPA06003578A MXPA06003578A MX PA06003578 A MXPA06003578 A MX PA06003578A MX PA06003578 A MXPA06003578 A MX PA06003578A MX PA06003578 A MXPA06003578 A MX PA06003578A MX PA06003578 A MXPA06003578 A MX PA06003578A

Authority

MX

Mexico

Prior art keywords

independently

further characterized

alkyl

butyl

assignments

Prior art date

2003-09-30

Links

• Espacenet
• Global Dossier
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• 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract 2
• 125000001424 substituent group Chemical group 0.000 claims abstract description 136
• 238000000034 method Methods 0.000 claims abstract description 131
• 239000000203 mixture Substances 0.000 claims abstract description 89
• 206010061218 Inflammation Diseases 0.000 claims abstract description 31
• 230000004054 inflammatory process Effects 0.000 claims abstract description 31
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
• 230000001404 mediated effect Effects 0.000 claims abstract description 18
• 210000000265 leukocyte Anatomy 0.000 claims abstract description 17
• 230000007115 recruitment Effects 0.000 claims abstract description 17
• 230000005764 inhibitory process Effects 0.000 claims abstract description 13
• 150000001875 compounds Chemical class 0.000 claims description 157
• -1 cyano, phenyl Chemical group 0.000 claims description 82
• 229910052739 hydrogen Inorganic materials 0.000 claims description 81
• 229910052799 carbon Inorganic materials 0.000 claims description 80
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 73
• 238000006243 chemical reaction Methods 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 66
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 150000002148 esters Chemical class 0.000 claims description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims description 45
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
• 230000028709 inflammatory response Effects 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 230000004044 response Effects 0.000 claims description 29
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
• 230000002265 prevention Effects 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 239000002904 solvent Substances 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 18
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 238000003379 elimination reaction Methods 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 10
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
• 208000006673 asthma Diseases 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 125000001246 bromo group Chemical group Br* 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 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 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 230000001900 immune effect Effects 0.000 claims description 9
• 239000011968 lewis acid catalyst Substances 0.000 claims description 9
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
• 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 8
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 8
• 208000023275 Autoimmune disease Diseases 0.000 claims description 8
• 201000010105 allergic rhinitis Diseases 0.000 claims description 8
• 229910052740 iodine Inorganic materials 0.000 claims description 8
• 239000012429 reaction media Substances 0.000 claims description 8
• 229940044551 receptor antagonist Drugs 0.000 claims description 8
• 239000002464 receptor antagonist Substances 0.000 claims description 8
• 239000003054 catalyst Substances 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 239000003377 acid catalyst Substances 0.000 claims description 6
• 238000009835 boiling Methods 0.000 claims description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 206010020751 Hypersensitivity Diseases 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 208000006045 Spondylarthropathies Diseases 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 208000026935 allergic disease Diseases 0.000 claims description 5
• 230000009285 allergic inflammation Effects 0.000 claims description 5
• 201000004339 autoimmune neuropathy Diseases 0.000 claims description 5
• 201000005671 spondyloarthropathy Diseases 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 230000002792 vascular Effects 0.000 claims description 5
• 230000006022 acute inflammation Effects 0.000 claims description 4
• 208000038016 acute inflammation Diseases 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 230000006020 chronic inflammation Effects 0.000 claims description 4
• 150000004885 piperazines Chemical class 0.000 claims description 4
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
• 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims description 3
• 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 3
• 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims description 3
• 208000009137 Behcet syndrome Diseases 0.000 claims description 3
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 3
• 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 206010012468 Dermatitis herpetiformis Diseases 0.000 claims description 3
• 208000007465 Giant cell arteritis Diseases 0.000 claims description 3
• 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 3
• 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims description 3
• 201000011152 Pemphigus Diseases 0.000 claims description 3
• 208000031845 Pernicious anaemia Diseases 0.000 claims description 3
• 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 206010039710 Scleroderma Diseases 0.000 claims description 3
• 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 206010047642 Vitiligo Diseases 0.000 claims description 3
• 210000004100 adrenal gland Anatomy 0.000 claims description 3
• 230000007815 allergy Effects 0.000 claims description 3
• 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims description 3
• 208000006424 autoimmune oophoritis Diseases 0.000 claims description 3
• 208000010928 autoimmune thyroid disease Diseases 0.000 claims description 3
• 201000004982 autoimmune uveitis Diseases 0.000 claims description 3
• 201000001981 dermatomyositis Diseases 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 230000008105 immune reaction Effects 0.000 claims description 3
• 238000010348 incorporation Methods 0.000 claims description 3
• 208000015181 infectious disease Diseases 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 230000009545 invasion Effects 0.000 claims description 3
• 206010025135 lupus erythematosus Diseases 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 206010028417 myasthenia gravis Diseases 0.000 claims description 3
• 201000005737 orchitis Diseases 0.000 claims description 3
• 201000001976 pemphigus vulgaris Diseases 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 claims description 3
• 206010043207 temporal arteritis Diseases 0.000 claims description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• 230000001363 autoimmune Effects 0.000 claims description 2
• SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 2
• 150000004050 homopiperazines Chemical class 0.000 claims description 2
• 230000007823 neuropathy Effects 0.000 claims description 2
• 201000001119 neuropathy Diseases 0.000 claims description 2
• 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims description 2
• 239000004031 partial agonist Substances 0.000 claims description 2
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
• 208000005987 polymyositis Diseases 0.000 claims description 2
• 239000011592 zinc chloride Substances 0.000 claims description 2
• 235000005074 zinc chloride Nutrition 0.000 claims description 2
• 229910003827 NRaRb Inorganic materials 0.000 claims 8
• 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 claims 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
• 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
• 229910052747 lanthanoid Inorganic materials 0.000 claims 1
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• 102000005962 receptors Human genes 0.000 abstract description 38
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 238000005481 NMR spectroscopy Methods 0.000 description 57
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 50
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 15
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• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 7
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• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
• ZQWWOKPRTSFJSL-UHFFFAOYSA-N 3-methoxy-8-methyl-1h-quinoxalin-2-one Chemical compound C1=CC(C)=C2NC(=O)C(OC)=NC2=C1 ZQWWOKPRTSFJSL-UHFFFAOYSA-N 0.000 description 6
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 6
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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• SNPABQDTALVVBG-UHFFFAOYSA-N 2,3,6-trichloro-7-methylquinoxaline Chemical compound ClC1=C(Cl)N=C2C=C(Cl)C(C)=CC2=N1 SNPABQDTALVVBG-UHFFFAOYSA-N 0.000 description 3
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