KR20060111466A - 퀴녹살린 화합물 - Google Patents
퀴녹살린 화합물 Download PDFInfo
- Publication number
- KR20060111466A KR20060111466A KR1020067008422A KR20067008422A KR20060111466A KR 20060111466 A KR20060111466 A KR 20060111466A KR 1020067008422 A KR1020067008422 A KR 1020067008422A KR 20067008422 A KR20067008422 A KR 20067008422A KR 20060111466 A KR20060111466 A KR 20060111466A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- substituents
- butyl
- och
- independently
- 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 abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 131
- 239000000203 mixture Substances 0.000 claims abstract description 112
- 102000005962 receptors Human genes 0.000 claims abstract description 55
- 108020003175 receptors Proteins 0.000 claims abstract description 55
- 206010061218 Inflammation Diseases 0.000 claims abstract description 34
- 230000004054 inflammatory process Effects 0.000 claims abstract description 34
- 208000024891 symptom Diseases 0.000 claims abstract description 29
- 230000001404 mediated effect Effects 0.000 claims abstract description 16
- 206010024378 leukocytosis Diseases 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 179
- 125000001424 substituent group Chemical group 0.000 claims description 149
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- 229910052799 carbon Inorganic materials 0.000 claims description 87
- -1 -NR a R b Chemical group 0.000 claims description 78
- 238000006243 chemical reaction Methods 0.000 claims description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 150000002148 esters Chemical class 0.000 claims description 53
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 39
- 230000028709 inflammatory response Effects 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
- 230000004044 response Effects 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 238000011282 treatment Methods 0.000 claims description 17
- 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 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 239000002904 solvent Substances 0.000 claims description 16
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 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 9
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 201000010105 allergic rhinitis Diseases 0.000 claims description 9
- 208000006673 asthma Diseases 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 239000011968 lewis acid catalyst Substances 0.000 claims description 9
- 239000012429 reaction media Substances 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000001900 immune effect Effects 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
- 229940044551 receptor antagonist Drugs 0.000 claims description 8
- 239000002464 receptor antagonist Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical group [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 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 230000001363 autoimmune Effects 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
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- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 206010047112 Vasculitides Diseases 0.000 claims description 5
- 206010047115 Vasculitis Diseases 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 230000009285 allergic inflammation Effects 0.000 claims description 5
- 201000004339 autoimmune neuropathy Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 229940075993 receptor modulator Drugs 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 230000006022 acute inflammation Effects 0.000 claims description 4
- 208000038016 acute inflammation Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 208000037976 chronic inflammation Diseases 0.000 claims description 4
- 230000006020 chronic inflammation Effects 0.000 claims description 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 208000003343 Antiphospholipid Syndrome 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
- 206010004659 Biliary cirrhosis Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000011231 Crohn disease 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
- 208000031845 Pernicious anaemia Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 208000006045 Spondylarthropathies Diseases 0.000 claims description 3
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 3
- 208000002474 Tinea Diseases 0.000 claims description 3
- 241000893966 Trichophyton verrucosum Species 0.000 claims description 3
- 230000001919 adrenal effect Effects 0.000 claims description 3
- 206010003230 arteritis Diseases 0.000 claims description 3
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims description 3
- 208000010928 autoimmune thyroid disease Diseases 0.000 claims description 3
- 150000004050 homopiperazines Chemical class 0.000 claims description 3
- 206010025135 lupus erythematosus Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
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- 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
- 201000005671 spondyloarthropathy Diseases 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
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- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 206010012468 Dermatitis herpetiformis Diseases 0.000 claims description 2
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- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 230000007815 allergy 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
- 230000009545 invasion Effects 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
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- 239000011967 lanthanide triflate Substances 0.000 claims 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 abstract description 3
- 238000002636 symptomatic treatment Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 60
- 238000007429 general method Methods 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 229960001340 histamine Drugs 0.000 description 33
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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| US60/507,176 | 2003-09-30 |
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| KR20060111466A true KR20060111466A (ko) | 2006-10-27 |
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| US (1) | US20050070527A1 (https=) |
| EP (1) | EP1670774A1 (https=) |
| JP (1) | JP2007507514A (https=) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20110018940A (ko) * | 2008-06-12 | 2011-02-24 | 얀센 파마슈티카 엔.브이. | 수술후 접착의 치료를 위한, 히스타민 ｈ4 길항제의 용도 |
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| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| WO2007117399A2 (en) | 2006-03-31 | 2007-10-18 | Janssen Pharmaceutica N.V. | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor |
| WO2007120690A2 (en) * | 2006-04-10 | 2007-10-25 | Janssen Pharmaceutica N.V. | Combination histamine h1r and h4r antagonist therapy for treating pruritus |
| US20100016293A1 (en) * | 2006-07-03 | 2010-01-21 | Rogier Adriaan Smits | Quinazolines and Related Heterocyclic Compounds, 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 |
| 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 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| WO2011092290A1 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| AR086554A1 (es) | 2011-05-27 | 2014-01-08 | Novartis Ag | Derivados de la piperidina 3-espirociclica como agonistas de receptores de la ghrelina |
| JP2015525202A (ja) | 2012-05-03 | 2015-09-03 | ノバルティス アーゲー | グレリン受容体アゴニストとしての２，７−ジアザ−スピロ［４，５］デカ−７−イル誘導体のｌ−リンゴ酸塩およびその結晶形態 |
| EP3378476A1 (en) | 2012-06-08 | 2018-09-26 | Sensorion | H4 receptor inhibitors for treating tinnitus |
| PT2964229T (pt) | 2013-03-06 | 2020-03-23 | Janssen Pharmaceutica Nv | Moduladores de piridina benzimidazol-2-ilo do recetor h4 de histamina |
| 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 |
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| US3493572A (en) * | 1968-07-05 | 1970-02-03 | Pfizer & Co C | Process for producing quinoxaline-di-n-oxides |
| FI193974A7 (https=) * | 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 |
| 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 WO PCT/US2004/032003 patent/WO2005033088A1/en not_active Ceased
- 2004-09-29 KR KR1020067008422A patent/KR20060111466A/ko not_active Withdrawn
- 2004-09-29 MX MXPA06003578A patent/MXPA06003578A/es unknown
- 2004-09-29 US US10/953,126 patent/US20050070527A1/en not_active Abandoned
- 2004-09-29 CN CN2004800348033A patent/CN1886389B/zh not_active Expired - Fee Related
- 2004-09-29 AU AU2004278372A patent/AU2004278372B2/en not_active Ceased
- 2004-09-29 EP EP04789260A patent/EP1670774A1/en not_active Withdrawn
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2006
- 2006-03-29 IL IL174629A patent/IL174629A0/en unknown
- 2006-04-28 ZA ZA200603410A patent/ZA200603410B/en unknown
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2010
- 2010-05-18 AU AU2010202009A patent/AU2010202009A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110018940A (ko) * | 2008-06-12 | 2011-02-24 | 얀센 파마슈티카 엔.브이. | 수술후 접착의 치료를 위한, 히스타민 ｈ4 길항제의 용도 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1886389A (zh) | 2006-12-27 |
| US20050070527A1 (en) | 2005-03-31 |
| EP1670774A1 (en) | 2006-06-21 |
| IL174629A0 (en) | 2006-08-20 |
| ZA200603410B (en) | 2007-07-25 |
| WO2005033088A1 (en) | 2005-04-14 |
| AU2004278372A1 (en) | 2005-04-14 |
| AU2004278372B2 (en) | 2010-02-18 |
| AU2010202009A1 (en) | 2010-06-10 |
| CN1886389B (zh) | 2010-07-21 |
| CA2540638A1 (en) | 2005-04-14 |
| JP2007507514A (ja) | 2007-03-29 |
| MXPA06003578A (es) | 2006-08-31 |
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