TW201103933A - CXCR3 receptor antagonists - Google Patents
CXCR3 receptor antagonists Download PDFInfo
- Publication number
- TW201103933A TW201103933A TW099113117A TW99113117A TW201103933A TW 201103933 A TW201103933 A TW 201103933A TW 099113117 A TW099113117 A TW 099113117A TW 99113117 A TW99113117 A TW 99113117A TW 201103933 A TW201103933 A TW 201103933A
- Authority
- TW
- Taiwan
- Prior art keywords
- phenyl
- pyridin
- piperazine
- alkyl
- ethyl
- Prior art date
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- 108010061300 CXCR3 Receptors Proteins 0.000 title 1
- 102000011963 CXCR3 Receptors Human genes 0.000 title 1
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- -1 dibenzofuranyl Chemical group 0.000 claims description 154
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 claims description 31
- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 claims description 31
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 26
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
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Classifications
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- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D403/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
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- General Health & Medical Sciences (AREA)
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- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
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| CN107207491A (zh) * | 2015-01-15 | 2017-09-26 | 爱杜西亚药品有限公司 | 作为cxcr3受体调节剂的(r)‑2‑甲基‑哌嗪衍生物 |
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| ES2620027T3 (es) | 2008-09-03 | 2017-06-27 | Biomarin Pharmaceutical Inc. | Composiciones que incluyen derivados del ácido 6-aminohexanoico como inhibidores de HDAC |
| JP5807971B2 (ja) * | 2009-04-27 | 2015-11-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｘｃｒ３受容体アンタゴニスト |
| JP2011057661A (ja) * | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| WO2011084985A1 (en) * | 2010-01-07 | 2011-07-14 | Boehringer Ingelheim International Gmbh | Cxcr3 receptor antagonists |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| EP2508511A1 (en) | 2011-04-07 | 2012-10-10 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| KR101800607B1 (ko) | 2012-02-02 | 2017-11-23 | 액테리온 파마슈티칼 리미티드 | ４-(벤조이미다졸-２-일)-티아졸 화합물 및 관련 아자 유도체 |
| KR20150132345A (ko) | 2013-03-15 | 2015-11-25 | 바이오마린 파머수티컬 인크. | Hdac 저해제 |
| WO2014182688A1 (en) * | 2013-05-07 | 2014-11-13 | Arena Pharmaceuticals, Inc. | Modulators of the g protein-coupled mas receptor and the treatment of disorders related thereto |
| WO2014182673A1 (en) * | 2013-05-07 | 2014-11-13 | Arena Pharmaceuticals, Inc. | Modulators of the g protein-coupled mas receptor and the treatment of disorders related thereto |
| WO2015002926A1 (en) | 2013-07-02 | 2015-01-08 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| AR096788A1 (es) | 2013-07-02 | 2016-02-03 | Bristol Myers Squibb Co | Compuestos tricíclicos de carboxamida como inhibidores potentes de rock |
| JP6330040B2 (ja) | 2013-07-22 | 2018-05-23 | イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | １−（ピペラジン−１−イル）−２−（［１，２，４］トリアゾール−１−イル）−エタノン誘導体 |
| AR099789A1 (es) * | 2014-03-24 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados de 8-(piperazin-1-il)-1,2,3,4-tetrahidro-isoquinolina |
| DK3174868T3 (da) | 2014-08-01 | 2021-11-08 | Nuevolution As | Forbindelser, der er aktive mod bromodomæner |
| TWI689497B (zh) * | 2014-09-04 | 2020-04-01 | 南北兄弟藥業投資有限公司 | 芳雜環類衍生物及其在藥物中的應用 |
| PT3245203T (pt) | 2015-01-15 | 2019-02-08 | Idorsia Pharmaceuticals Ltd | Derivados de hidroxialquil-piperazina como modeladores do recetor cxcr3 |
| IL312413B1 (en) | 2018-08-29 | 2025-09-01 | Acerta Pharma Bv | Processes for the preparation of 4-{8-amino-3-[(2s)-1-(but-2-enol)-pyrrolidin-2-yl]imidazo[1,5-a]-pyrazin-1-yl}n-(pyridin-2-yl)-benzamide |
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| ES2329356T3 (es) * | 2002-06-12 | 2009-11-25 | Chemocentryx, Inc. | Derivados de piperazina 1-arilo-4-sustituidos utilizados como antagonistas de ccr1 para el tratamiento de enfermedades inflamatorias e inmunitarias. |
| US20050256130A1 (en) * | 2002-06-12 | 2005-11-17 | Chemocentryx, Inc. | Substituted piperazines |
| CA2514940A1 (en) * | 2003-02-03 | 2004-08-19 | Janssen Pharmaceutica N.V. | Quinoline-derived amide modulators of vanilloid vr1 receptor |
| ES2543714T3 (es) * | 2005-06-22 | 2015-08-21 | Chemocentryx, Inc. | Compuestos de azaindazol y métodos de uso |
| US20090030012A1 (en) * | 2006-02-23 | 2009-01-29 | Adams Alan D | Pyridine, Pyrimidine and Pyrazine Derivatives as Cxcr3 Receptor Modulators |
| JP5286646B2 (ja) * | 2006-04-19 | 2013-09-11 | トヨタ自動車株式会社 | スルホン基含有モノマーの重合方法 |
| CN101426774B (zh) * | 2006-04-19 | 2012-04-25 | 安斯泰来制药有限公司 | 唑类甲酰胺衍生物 |
| US20090099201A1 (en) * | 2007-05-22 | 2009-04-16 | David Robert Bolin | Diacylglycerol Acyltransferase Inhibitors |
| JO2972B1 (en) * | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| JP5807971B2 (ja) * | 2009-04-27 | 2015-11-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｘｃｒ３受容体アンタゴニスト |
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| CN107207491A (zh) * | 2015-01-15 | 2017-09-26 | 爱杜西亚药品有限公司 | 作为cxcr3受体调节剂的(r)‑2‑甲基‑哌嗪衍生物 |
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| EP2424858B1 (en) | 2014-05-14 |
| EP2424858A1 (en) | 2012-03-07 |
| US20100273781A1 (en) | 2010-10-28 |
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