CA2540638A1 - Quinoxaline compounds - Google Patents
Quinoxaline compounds Download PDFInfo
- Publication number
- CA2540638A1 CA2540638A1 CA002540638A CA2540638A CA2540638A1 CA 2540638 A1 CA2540638 A1 CA 2540638A1 CA 002540638 A CA002540638 A CA 002540638A CA 2540638 A CA2540638 A CA 2540638A CA 2540638 A1 CA2540638 A1 CA 2540638A1
- Authority
- CA
- Canada
- Prior art keywords
- independently
- butyl
- substituent assignments
- group
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 188
- 125000001424 substituent group Chemical group 0.000 claims abstract description 138
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 102000005962 receptors Human genes 0.000 claims abstract description 41
- 108020003175 receptors Proteins 0.000 claims abstract description 41
- 206010061218 Inflammation Diseases 0.000 claims abstract description 31
- 230000004054 inflammatory process Effects 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 210000000265 leukocyte Anatomy 0.000 claims abstract description 18
- 230000001404 mediated effect Effects 0.000 claims abstract description 16
- 230000007115 recruitment Effects 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 160
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 90
- -1 -NR a R b Chemical group 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 229910052799 carbon Inorganic materials 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- 150000002148 esters Chemical class 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
- 230000028709 inflammatory response Effects 0.000 claims description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- 230000004044 response Effects 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 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 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 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
- 238000003379 elimination reaction Methods 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 239000011968 lewis acid catalyst Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 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
- 125000002373 5 membered heterocyclic group Chemical group 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
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 8
- 201000010105 allergic rhinitis Diseases 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 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 8
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 230000001900 immune effect Effects 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
- 229940044551 receptor antagonist Drugs 0.000 claims description 6
- 239000002464 receptor antagonist Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 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
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- 230000009285 allergic inflammation Effects 0.000 claims description 5
- 201000004339 autoimmune neuropathy Diseases 0.000 claims description 5
- 229940075993 receptor modulator Drugs 0.000 claims description 5
- 201000005671 spondyloarthropathy Diseases 0.000 claims description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 5
- 206010047112 Vasculitides Diseases 0.000 claims description 4
- 206010047115 Vasculitis Diseases 0.000 claims description 4
- 230000006022 acute inflammation Effects 0.000 claims description 4
- 208000038016 acute inflammation Diseases 0.000 claims description 4
- 208000037976 chronic inflammation Diseases 0.000 claims description 4
- 230000006020 chronic inflammation Effects 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 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
- 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
- 208000019693 Lung disease 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
- 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
- 230000001684 chronic effect Effects 0.000 claims description 3
- 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 3
- 201000001981 dermatomyositis Diseases 0.000 claims description 3
- 150000004050 homopiperazines Chemical class 0.000 claims description 3
- 208000015181 infectious disease Diseases 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
- 239000004031 partial agonist Substances 0.000 claims description 3
- 201000001976 pemphigus vulgaris Diseases 0.000 claims description 3
- 150000004885 piperazines Chemical class 0.000 claims description 3
- 208000005987 polymyositis 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
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 230000001363 autoimmune Effects 0.000 claims description 2
- 239000011967 lanthanide triflate Substances 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
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- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims description 2
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 17
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 15
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 7
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- 229920000728 polyester Polymers 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 17
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Medicinal Chemistry (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Diabetes (AREA)
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- Hematology (AREA)
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- Pulmonology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50717603P | 2003-09-30 | 2003-09-30 | |
| US60/507,176 | 2003-09-30 | ||
| PCT/US2004/032003 WO2005033088A1 (en) | 2003-09-30 | 2004-09-29 | Quinoxaline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2540638A1 true CA2540638A1 (en) | 2005-04-14 |
Family
ID=34421591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002540638A Abandoned CA2540638A1 (en) | 2003-09-30 | 2004-09-29 | Quinoxaline compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20050070527A1 (enExample) |
| EP (1) | EP1670774A1 (enExample) |
| JP (1) | JP2007507514A (enExample) |
| KR (1) | KR20060111466A (enExample) |
| CN (1) | CN1886389B (enExample) |
| AU (2) | AU2004278372B2 (enExample) |
| CA (1) | CA2540638A1 (enExample) |
| IL (1) | IL174629A0 (enExample) |
| MX (1) | MXPA06003578A (enExample) |
| WO (1) | WO2005033088A1 (enExample) |
| ZA (1) | ZA200603410B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| ATE478067T1 (de) | 2006-03-31 | 2010-09-15 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyridine und pyrazine als modulatoren des histamin-h4-rezeptors |
| WO2007120690A2 (en) * | 2006-04-10 | 2007-10-25 | Janssen Pharmaceutica N.V. | Combination histamine h1r and h4r antagonist therapy for treating pruritus |
| AU2007271187A1 (en) * | 2006-07-03 | 2008-01-10 | Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek En Patientenzorg | Fused bicyclic compounds interacting with the histamine H4 receptor |
| GB0614471D0 (en) | 2006-07-20 | 2006-08-30 | Syngenta Ltd | Herbicidal Compounds |
| US7985745B2 (en) | 2006-10-02 | 2011-07-26 | Abbott Laboratories | Method for pain treatment |
| EP2077263A1 (en) * | 2008-01-02 | 2009-07-08 | Vereniging voor christelijk hoger onderwijs, wetenschappelijk onderzoek en patiëntenzorg | Quinazolines and related heterocyclic compounds and their therapeutic use |
| UA100567C2 (ru) * | 2008-06-12 | 2013-01-10 | Янссен Фармацевтика Нв | Использование антагонистов н4-гистаминовых рецепторов для лечения послеоперационных спаек |
| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
| EP2201982A1 (en) | 2008-12-24 | 2010-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Histamine H4 receptor antagonists for the treatment of vestibular disorders |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| CN102762572A (zh) | 2010-02-01 | 2012-10-31 | 诺瓦提斯公司 | 作为CRF-1受体拮抗剂的吡唑并[5,1b]*唑衍生物 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| UY34094A (es) | 2011-05-27 | 2013-01-03 | Novartis Ag | Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina |
| WO2013164790A1 (en) | 2012-05-03 | 2013-11-07 | Novartis Ag | L-malate salt of 2, 7 - diaza - spiro [4.5 ] dec- 7 - yle derivatives and crystalline forms thereof as ghrelin receptor agonists |
| HUE039713T2 (hu) | 2012-06-08 | 2019-02-28 | Sensorion | H4 receptor inhibitorok tinnitus kezelésére |
| JO3516B1 (ar) | 2013-03-06 | 2020-07-05 | Janssen Pharmaceutica Nv | مُعدِّلات بنزإيميدازول-2-يل بيريميدين لمستقبل الهستامين h4 |
| CN105001169B (zh) * | 2015-07-09 | 2017-07-21 | 华侨大学 | 一种3‑氨基喹喔啉‑2(1h)‑酮类化合物的合成方法 |
| CN110092760B (zh) * | 2019-06-04 | 2020-11-13 | 杭州师范大学 | 一种3-氟代烷氧基-2(1h)-喹喔啉酮及其合成方法 |
| KR20240057402A (ko) * | 2021-07-23 | 2024-05-02 | 인스티튜트 내셔날 드 라 싼테 에 드 라 리셰르셰 메디칼르 | 그람 음성 박테리아 유출 펌프 억제제 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3493572A (en) * | 1968-07-05 | 1970-02-03 | Pfizer & Co C | Process for producing quinoxaline-di-n-oxides |
| FI193974A7 (enExample) * | 1973-07-13 | 1975-01-14 | Merck & Co Inc | |
| EP0008864A1 (en) * | 1978-08-15 | 1980-03-19 | FISONS plc | Pyridopyrazine and quinoxaline derivatives, processes for their preparation, and pharmaceutical compositions containing them |
| DK716188D0 (da) * | 1988-12-22 | 1988-12-22 | Ferrosan As | Quinoxalinforbindelser, deres fremstilling og anvendelse |
| DE4342024A1 (de) * | 1993-12-09 | 1995-06-14 | Hoechst Ag | Kombinationspräparate, enthaltend ein Chinoxalin und ein Nukleosid |
| MY132385A (en) * | 1995-08-31 | 2007-10-31 | Novartis Ag | 2,3-dioxo-1,2,3,4-tetrahydro-quinoxalinyl derivatives |
| DK1534391T3 (da) * | 2002-07-19 | 2007-06-11 | Biovitrum Ab | Nye piperazinyl-pyrazinonderivater til behandling af 5-HT2A-recptor-relaterede forstyrrelser |
-
2004
- 2004-09-29 EP EP04789260A patent/EP1670774A1/en not_active Withdrawn
- 2004-09-29 WO PCT/US2004/032003 patent/WO2005033088A1/en not_active Ceased
- 2004-09-29 AU AU2004278372A patent/AU2004278372B2/en not_active Ceased
- 2004-09-29 MX MXPA06003578A patent/MXPA06003578A/es unknown
- 2004-09-29 CA CA002540638A patent/CA2540638A1/en not_active Abandoned
- 2004-09-29 KR KR1020067008422A patent/KR20060111466A/ko not_active Withdrawn
- 2004-09-29 CN CN2004800348033A patent/CN1886389B/zh not_active Expired - Fee Related
- 2004-09-29 US US10/953,126 patent/US20050070527A1/en not_active Abandoned
- 2004-09-29 JP JP2006534060A patent/JP2007507514A/ja active Pending
-
2006
- 2006-03-29 IL IL174629A patent/IL174629A0/en unknown
- 2006-04-28 ZA ZA200603410A patent/ZA200603410B/en unknown
-
2010
- 2010-05-18 AU AU2010202009A patent/AU2010202009A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06003578A (es) | 2006-08-31 |
| KR20060111466A (ko) | 2006-10-27 |
| EP1670774A1 (en) | 2006-06-21 |
| JP2007507514A (ja) | 2007-03-29 |
| AU2004278372A1 (en) | 2005-04-14 |
| IL174629A0 (en) | 2006-08-20 |
| CN1886389B (zh) | 2010-07-21 |
| AU2004278372B2 (en) | 2010-02-18 |
| AU2010202009A1 (en) | 2010-06-10 |
| WO2005033088A1 (en) | 2005-04-14 |
| ZA200603410B (en) | 2007-07-25 |
| US20050070527A1 (en) | 2005-03-31 |
| CN1886389A (zh) | 2006-12-27 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |