AU2004278372B2 - Quinoxaline compounds - Google Patents
Quinoxaline compounds Download PDFInfo
- Publication number
- AU2004278372B2 AU2004278372B2 AU2004278372A AU2004278372A AU2004278372B2 AU 2004278372 B2 AU2004278372 B2 AU 2004278372B2 AU 2004278372 A AU2004278372 A AU 2004278372A AU 2004278372 A AU2004278372 A AU 2004278372A AU 2004278372 B2 AU2004278372 B2 AU 2004278372B2
- Authority
- AU
- Australia
- Prior art keywords
- independently
- alkyl
- substituent assignments
- substituent
- assignments
- 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.)
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- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims description 300
- 150000001875 compounds Chemical class 0.000 claims description 163
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 154
- 238000000034 method Methods 0.000 claims description 130
- 229910052799 carbon Inorganic materials 0.000 claims description 129
- 125000000217 alkyl group Chemical group 0.000 claims description 127
- -1 -NRaR Chemical group 0.000 claims description 113
- 229910052757 nitrogen Inorganic materials 0.000 claims description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 150000002148 esters Chemical class 0.000 claims description 64
- 125000003545 alkoxy group Chemical group 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 55
- 102000005962 receptors Human genes 0.000 claims description 54
- 108020003175 receptors Proteins 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 49
- 125000000304 alkynyl group Chemical group 0.000 claims description 48
- 125000005843 halogen group Chemical group 0.000 claims description 48
- 239000008194 pharmaceutical composition Substances 0.000 claims description 48
- 230000004044 response Effects 0.000 claims description 47
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 230000007115 recruitment Effects 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 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 23
- 230000001404 mediated effect Effects 0.000 claims description 23
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 201000005671 spondyloarthropathy Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 3
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- 150000002431 hydrogen Chemical class 0.000 claims description 3
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- 206010028417 myasthenia gravis Diseases 0.000 claims description 3
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- 239000004031 partial agonist Substances 0.000 claims description 3
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 2
- 230000001363 autoimmune Effects 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
- 201000001119 neuropathy Diseases 0.000 claims description 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 57
- 238000005481 NMR spectroscopy Methods 0.000 description 51
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 238000000746 purification Methods 0.000 description 32
- 210000004027 cell Anatomy 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 25
- 229960001340 histamine Drugs 0.000 description 24
- 210000003630 histaminocyte Anatomy 0.000 description 22
- 239000002904 solvent Substances 0.000 description 19
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 18
- 210000003979 eosinophil Anatomy 0.000 description 18
- 238000010898 silica gel chromatography Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical class N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 241000282414 Homo sapiens Species 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 8
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- XXKGDIUNVPKNTI-UHFFFAOYSA-N 3-methoxy-6-(trifluoromethyl)-1h-quinoxalin-2-one Chemical compound FC(F)(F)C1=CC=C2NC(=O)C(OC)=NC2=C1 XXKGDIUNVPKNTI-UHFFFAOYSA-N 0.000 description 6
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- JTEVAMLYVXCLAE-UHFFFAOYSA-N 2,6-dichloro-7-methyl-3-(4-methylpiperazin-1-yl)quinoxaline Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=C(C)C=C2N=C1Cl JTEVAMLYVXCLAE-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
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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
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Landscapes
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2010202009A AU2010202009A1 (en) | 2003-09-30 | 2010-05-18 | Quinoxaline compounds |
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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010202009A Division AU2010202009A1 (en) | 2003-09-30 | 2010-05-18 | Quinoxaline compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004278372A1 AU2004278372A1 (en) | 2005-04-14 |
| AU2004278372B2 true AU2004278372B2 (en) | 2010-02-18 |
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| AU2004278372A Ceased AU2004278372B2 (en) | 2003-09-30 | 2004-09-29 | Quinoxaline compounds |
| AU2010202009A Abandoned AU2010202009A1 (en) | 2003-09-30 | 2010-05-18 | Quinoxaline compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010202009A Abandoned AU2010202009A1 (en) | 2003-09-30 | 2010-05-18 | Quinoxaline compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20050070527A1 (OSRAM) |
| EP (1) | EP1670774A1 (OSRAM) |
| JP (1) | JP2007507514A (OSRAM) |
| KR (1) | KR20060111466A (OSRAM) |
| CN (1) | CN1886389B (OSRAM) |
| AU (2) | AU2004278372B2 (OSRAM) |
| CA (1) | CA2540638A1 (OSRAM) |
| IL (1) | IL174629A0 (OSRAM) |
| MX (1) | MXPA06003578A (OSRAM) |
| WO (1) | WO2005033088A1 (OSRAM) |
| ZA (1) | ZA200603410B (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| BRPI0710083A2 (pt) | 2006-03-31 | 2011-08-02 | Janssen Pharmaceutica Nv | entidade quìmica benzoimidazol-2-il pirimidina e pirazina, composição farmacêutica e uso destas |
| US20090069343A1 (en) * | 2006-04-10 | 2009-03-12 | Dunford Paul J | Combination Histamine H1R and H4R Antagonist Therapy for Treating Pruritus |
| CA2657702A1 (en) * | 2006-07-03 | 2008-01-10 | Vereniging Voor Christelijk Hoger Onderwijs Wetenschappelijk Onderzoek E N Patieentenzorg | Quinazolines and related heterocyclic comp0unds, and their therapeutic use |
| 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 |
| NZ589531A (en) * | 2008-06-12 | 2012-08-31 | Janssen Pharmaceutica Nv | Use of histamine H4 antagonist for the treatment of post-operative tissue adhesions after surgical procedures |
| 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 |
| WO2011092293A2 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Cyclohexyl amide derivatives as crf receptor antagonists |
| CN102753527B (zh) | 2010-02-02 | 2014-12-24 | 诺华股份有限公司 | 用作crf受体拮抗剂的环己基酰胺衍生物 |
| UY34094A (es) | 2011-05-27 | 2013-01-03 | Novartis Ag | Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina |
| EA201491990A1 (ru) | 2012-05-03 | 2015-02-27 | Новартис Аг | L-малатная соль 2,7-диазаспиро[4.5]дец-7-иловых производных и их кристаллические формы в качестве агонистов грелиновых рецепторов |
| SI2858647T1 (sl) | 2012-06-08 | 2018-11-30 | Sensorion | Inhibitorji receptorja H4 za zdravljenje tinitusa |
| HUE047681T2 (hu) | 2013-03-06 | 2020-05-28 | Janssen Pharmaceutica Nv | A hisztamin H4 receptor benzimidazol-2-il-pirimidin modulátorai |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1440722A (en) * | 1973-07-13 | 1976-06-23 | Merck & Co Inc | 2-1-piperazinyl-quinoxaline compounds having pharmaceutical activity |
Family Cites Families (6)
| 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 |
| 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 |
| PT1534391E (pt) * | 2002-07-19 | 2007-05-31 | Biovitrum Ab | Novos derivados e piperazinilo-pirazinona para o tratamento de desordens relacionadas com o receptor 5-ht |
-
2004
- 2004-09-29 JP JP2006534060A patent/JP2007507514A/ja active Pending
- 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 US US10/953,126 patent/US20050070527A1/en not_active Abandoned
- 2004-09-29 AU AU2004278372A patent/AU2004278372B2/en not_active Ceased
- 2004-09-29 CN CN2004800348033A patent/CN1886389B/zh not_active Expired - Fee Related
- 2004-09-29 WO PCT/US2004/032003 patent/WO2005033088A1/en not_active Ceased
- 2004-09-29 MX MXPA06003578A patent/MXPA06003578A/es unknown
- 2004-09-29 EP EP04789260A patent/EP1670774A1/en not_active Withdrawn
-
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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1440722A (en) * | 1973-07-13 | 1976-06-23 | Merck & Co Inc | 2-1-piperazinyl-quinoxaline compounds having pharmaceutical activity |
Non-Patent Citations (1)
| Title |
|---|
| Lumma et al, Journal of Medicinal Chemistry, 1981, 24:93-101 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050070527A1 (en) | 2005-03-31 |
| CN1886389A (zh) | 2006-12-27 |
| AU2004278372A1 (en) | 2005-04-14 |
| AU2010202009A1 (en) | 2010-06-10 |
| CA2540638A1 (en) | 2005-04-14 |
| EP1670774A1 (en) | 2006-06-21 |
| KR20060111466A (ko) | 2006-10-27 |
| WO2005033088A1 (en) | 2005-04-14 |
| ZA200603410B (en) | 2007-07-25 |
| MXPA06003578A (es) | 2006-08-31 |
| IL174629A0 (en) | 2006-08-20 |
| CN1886389B (zh) | 2010-07-21 |
| JP2007507514A (ja) | 2007-03-29 |
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