NO327345B1 - 2,4,5-trisubstituerte tiazolylderivater og deres antiinflammatoriske aktivitet - Google Patents
2,4,5-trisubstituerte tiazolylderivater og deres antiinflammatoriske aktivitet Download PDFInfo
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- NO327345B1 NO327345B1 NO20040631A NO20040631A NO327345B1 NO 327345 B1 NO327345 B1 NO 327345B1 NO 20040631 A NO20040631 A NO 20040631A NO 20040631 A NO20040631 A NO 20040631A NO 327345 B1 NO327345 B1 NO 327345B1
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- -1 2,4,5-trisubstituted thiazolyl Chemical class 0.000 title claims abstract description 108
- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 29
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims abstract description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 25
- 108010065805 Interleukin-12 Proteins 0.000 claims abstract description 23
- 102000013462 Interleukin-12 Human genes 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 230000001404 mediated effect Effects 0.000 claims abstract description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 230000002265 prevention Effects 0.000 claims abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 7
- 125000003277 amino group Chemical group 0.000 claims abstract 3
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- 125000000217 alkyl group Chemical group 0.000 claims description 35
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- 238000000034 method Methods 0.000 claims description 27
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- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
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- 230000002757 inflammatory effect Effects 0.000 claims description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
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- 230000000947 anti-immunosuppressive effect Effects 0.000 claims description 3
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- 238000000844 transformation Methods 0.000 claims 1
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- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 abstract description 20
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- 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
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| EP01203088 | 2001-08-13 | ||
| PCT/EP2002/008956 WO2003015776A1 (en) | 2001-08-13 | 2002-08-09 | 2,4,5-trisubstituted thiazolyl derivatives and their antiinflammatory activity |
Publications (2)
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Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7361665B2 (en) | 2002-07-09 | 2008-04-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases |
| PA8578101A1 (es) * | 2002-08-13 | 2004-05-07 | Warner Lambert Co | Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz |
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| JP2007519720A (ja) | 2004-01-28 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | チアゾール化合物 |
| WO2006038734A1 (en) * | 2004-10-08 | 2006-04-13 | Astellas Pharma Inc. | Pyridazinone derivatives cytokines inhibitors |
| JP2008516946A (ja) * | 2004-10-15 | 2008-05-22 | アストラゼネカ・アクチエボラーグ | 置換されたアミノ−ピリミドンおよびそれらの使用 |
| JP2008516945A (ja) * | 2004-10-15 | 2008-05-22 | アストラゼネカ・アクチエボラーグ | 置換されたアミノ化合物およびそれらの使用 |
| JP2008531537A (ja) * | 2005-02-25 | 2008-08-14 | クドス ファーマシューティカルズ リミテッド | 化合物 |
| BRPI0616655A2 (pt) | 2005-10-03 | 2011-06-28 | Ono Pharmaceutical Co | composto heterocìclico contendo nitrogênio e aplicação farmacêutica do mesmo |
| RU2010121969A (ru) * | 2007-11-01 | 2011-12-10 | Актелион Фармасьютиклз Лтд (Ch) | Новые производные пиримидина |
| WO2009094224A1 (en) | 2008-01-25 | 2009-07-30 | Millennium Pharmaceuticals, Inc. | Thiophenes and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors |
| TWI403506B (zh) * | 2008-06-16 | 2013-08-01 | Faes Farma Sa | 用於治療急性和慢性發炎疾病之５－（４－甲磺醯基－苯基）－噻唑衍生物類 |
| ES2426953T3 (es) | 2008-07-17 | 2013-10-28 | Bayer Cropscience Ag | Compuestos heterocíclicos como pesticidas |
| KR101406433B1 (ko) | 2008-09-22 | 2014-06-13 | 카이맨 케미칼 컴파니 인코포레이티드 | Ｈ-ｐｇｄｓ 억제제로서 다중헤테로아릴 화합물 및 프로스타글란딘 ｄ2 매개된 질병의 치료를 위한 그의 용도 |
| TW201026693A (en) * | 2008-10-01 | 2010-07-16 | Synta Pharmaceuticals Corp | Compounds for inflammation and immune-related uses |
| CN101391984B (zh) * | 2008-11-07 | 2010-12-08 | 东华大学 | 碳酸二甲酯对含巯基的嘧啶杂环化合物进行甲基化的方法 |
| US9090601B2 (en) * | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| CN102395585A (zh) | 2009-01-30 | 2012-03-28 | 米伦纽姆医药公司 | 杂芳基化合物和其作为pi3k抑制剂的用途 |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2011138285A1 (de) | 2010-05-05 | 2011-11-10 | Bayer Cropscience Ag | Thiazolderivate als schädlingsbekämpfungsmittel |
| US9062038B2 (en) | 2010-08-11 | 2015-06-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| CA2807971A1 (en) | 2010-08-11 | 2012-02-16 | Millenium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| EP2603216A4 (en) | 2010-08-11 | 2013-12-18 | Millennium Pharm Inc | HETEROARYLE AND USES THEREOF |
| UY33671A (es) | 2010-10-13 | 2012-04-30 | Millenium Pharmaceuticals Inc | Heteroarilos y sus usos |
| US20120129843A1 (en) * | 2010-11-18 | 2012-05-24 | Yan Zhang | Pyridyl-thiazolyl inhibitors of pro-matrix metalloproteinase activation |
| WO2012109573A1 (en) * | 2011-02-11 | 2012-08-16 | Purdue Research Foundation | Substituted thiazoles for use as antiviral agents |
| CN104603124B (zh) | 2012-08-10 | 2018-04-17 | 勃林格殷格翰国际有限公司 | 用作布鲁顿酪氨酸激酶(btk)抑制剂的杂芳族化合物 |
| BR112015009751A2 (pt) * | 2012-10-31 | 2017-07-11 | Bayer Cropscience Ag | novos compostos heterocíclicos como pesticidas |
| EP2925744B1 (en) | 2012-11-27 | 2020-12-30 | Thomas Helledays Stiftelse För Medicinsk Forskning | Pyrimidine-2,4-diamine derivatives for treatment of cancer |
| JP6486954B2 (ja) | 2014-01-29 | 2019-03-20 | 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 | Ｂｔｋ阻害剤としてのピラゾール化合物 |
| CA2948601A1 (en) | 2014-06-04 | 2015-12-10 | Thomas Helledays Stiftelse For Medicinsk Forskning | Mth1 inhibitors for treatment of inflammatory and autoimmune conditions |
| WO2015187088A1 (en) | 2014-06-04 | 2015-12-10 | Thomas Helledays Stiftelse För Medicinsk Forskning | Mth1 inhibitors for treatment of cancer |
| JOP20200117A1 (ar) | 2014-10-30 | 2017-06-16 | Janssen Pharmaceutica Nv | كحولات ثلاثي فلوروميثيل كمُعدلات للمستقبل النووي جاما تي المرتبط بحمض الريتيونَويك ROR?t |
| EP3212641B1 (en) | 2014-10-30 | 2018-12-05 | Janssen Pharmaceutica NV | Thiazoles as modulators of roryt |
| CN108064224B (zh) * | 2014-10-30 | 2022-03-29 | 詹森药业有限公司 | 作为Rorγt的调节剂的酰胺取代的噻唑 |
| EP3390390B1 (en) | 2015-12-16 | 2021-09-01 | Boehringer Ingelheim International Gmbh | Bipyrazolyl derivatives useful for the treatment of autoimmune diseases |
| EP3402789B1 (en) | 2016-01-13 | 2020-03-18 | Boehringer Ingelheim International Gmbh | Isoquinolones as btk inhibitors |
| TW201803869A (zh) | 2016-04-27 | 2018-02-01 | 健生藥品公司 | 作為ＲＯＲγＴ調節劑之６－胺基吡啶－３－基噻唑 |
| US10414759B2 (en) * | 2017-05-08 | 2019-09-17 | Purdue Research Foundation | Phenylthiazoles and uses thereof |
| CN112292373A (zh) | 2018-06-18 | 2021-01-29 | 詹森药业有限公司 | 作为RORγt的调节剂的吡啶基吡唑类 |
| US10975057B2 (en) | 2018-06-18 | 2021-04-13 | Janssen Pharmaceutica Nv | 6-aminopyridin-3-yl pyrazoles as modulators of RORgT |
| CA3103929A1 (en) | 2018-06-18 | 2019-12-26 | Janssen Pharmaceutica Nv | Phenyl substituted pyrazoles as modulators of roryt |
| CN112334450A (zh) | 2018-06-18 | 2021-02-05 | 詹森药业有限公司 | 作为RORγt的调节剂的苯基和吡啶基取代的咪唑 |
| CN110746325A (zh) * | 2018-07-24 | 2020-02-04 | 上海和辉光电有限公司 | 一种基于胍骨架的n型掺杂化合物及其应用 |
| CN110452224B (zh) * | 2019-08-30 | 2022-06-03 | 西南大学 | 嘧啶唑醇类化合物及其制备方法和应用 |
| WO2022155941A1 (en) * | 2021-01-25 | 2022-07-28 | Qilu Regor Therapeutics Inc. | Cdk2 inhibitors |
Family Cites Families (23)
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| US3499762A (en) | 1966-11-03 | 1970-03-10 | Eastman Kodak Co | Photographic elements comprising novel u.v.-absorbing optical brightening agents |
| DE1959307A1 (de) | 1969-11-26 | 1971-06-03 | Basf Ag | Optische Aufheller |
| BE795907A (fr) * | 1972-02-25 | 1973-06-18 | Luso Farmaco Inst | 2-amino-4-arylthiazoles 5-substitues et leur preparation |
| US4649146A (en) | 1983-01-31 | 1987-03-10 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivatives and pharmaceutical composition comprising the same |
| JPH03144612A (ja) | 1989-10-31 | 1991-06-20 | Nec Corp | 接続方法 |
| JPH04368375A (ja) * | 1991-06-17 | 1992-12-21 | Otsuka Pharmaceut Factory Inc | イソオキサゾール誘導体 |
| US5240929A (en) * | 1992-08-03 | 1993-08-31 | Warner-Lambert Company | 2-heterocyclic-5-hydroxy-1,3-pyrimidines useful as antiinflammatory agents |
| CA2195847A1 (en) * | 1994-07-27 | 1996-02-08 | John J. Talley | Substituted thiazoles for the treatment of inflammation |
| AU6788996A (en) | 1995-08-02 | 1997-02-26 | J. Uriach & Cia S.A. | New carboxamides with antifungal activity |
| AR008395A1 (es) | 1996-07-09 | 2000-01-19 | Astra Pharma Prod | Compuesto derivado de pirimidina, composicion farmaceutica que lo comprende, procedimiento para prepararlo, y compuesto intermediario util parallevar a cabo dicho procedimiento. |
| WO1998008830A1 (de) | 1996-08-26 | 1998-03-05 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Thiazol-derivate als selektive inhibitoren der pde-iv |
| SI0920426T1 (en) | 1996-08-26 | 2004-04-30 | Altana Pharma Ag | New thiazole derivatives with phosphodiesterase-inhibiting effect |
| DE69903976T2 (de) * | 1998-12-16 | 2003-07-24 | Aventis Pharma Ltd | Heteroaryl-zyklische acetale |
| DE10001644A1 (de) * | 1999-01-19 | 2000-07-20 | Clariant Gmbh | Fluorierte Azole und ihre Verwendung in flüssigkristallinen Mischungen |
| WO2001030778A1 (en) | 1999-10-27 | 2001-05-03 | Novartis Ag | Thiazole and imidazo [4,5-b] pyridine compounds and their pharmaceutical use |
| ES2222336T3 (es) * | 2000-01-18 | 2005-02-01 | Vertex Pharma | Inhibidores de girasas y sus usos. |
| AU3740101A (en) | 2000-03-01 | 2001-09-12 | Janssen Pharmaceutica Nv | 2,4-disubstituted thiazolyl derivatives |
| CN100355751C (zh) * | 2000-03-29 | 2007-12-19 | 西克拉塞尔有限公司 | 2－取代的4－杂芳基－嘧啶、其组合物及其用途 |
| GB0031109D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| GB0031107D0 (en) | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| JP2004517100A (ja) * | 2000-12-20 | 2004-06-10 | グラクソ グループ リミテッド | ｈＰＰＡＲアルファアゴニストとしての置換オキサゾールおよびチアゾール |
| GB0031103D0 (en) | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
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