2-氨基噻唑-4-基苯基酮 | 85616-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氨基噻唑-4-基苯基酮
• 英文名称: (2-aminothiazol-4-yl)(phenyl)methanone
• 英文别名: 2-aminothiazol-4-yl phenyl ketone；(2-amino-thiazol-4-yl)-phenyl-methanone；2-Amino-4-benzoyl-thiazol；(2-Amino-1,3-thiazol-4-yl)-phenylmethanone
• CAS: 85616-28-0
• 化学式: C₁₀H₈N₂OS
• 分子量: 204.252
• InChiKey: TWGCOFGDZUCMJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基噻唑-4-基苯基酮 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 反应 16.17h， 以50%的产率得到
  参考文献：
  名称：

  Substituted heteroaryl amide modulators of glucocorticoid receptor, AP-1, and/or NF-kB activity and use thereof

  摘要：

  本发明涉及一类新的非甾体化合物，用于治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病，包括肥胖、糖尿病、炎症和免疫相关疾病，并具有结构，包括其所有立体异构体、互变异构体或前药，或其药用可接受盐，其中X选自N、O和S；Y为N或CR6；Z为一个环；R、Ra、Rb、Rc、Rd、R1、R2、R3、R4和R5如本文所定义。还提供了包含所述化合物的药物组合物和治疗肥胖、糖尿病以及炎症或免疫相关疾病的方法。

  公开号：

  US20060154973A1
• 作为产物：
  描述：

  2-ethoxy-1-phenylprop-2-en-1-one 在 水 、 溴 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 2-氨基噻唑-4-基苯基酮
  参考文献：
  名称：

  Hamer, Neil K., Journal of the Chemical Society. Perkin transactions I, 1983, # 1, p. 61 - 64

  摘要：

  DOI：

文献信息

• [EN] NOVEL THIAZOLE DERIVATES<br/>[FR] NOUVEAUX DERIVES DE THIAZOLE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005058887A1

  公开（公告）日：2005-06-30

  The present invention relates to compounds of formula (I)wherein R1, R2, R3 and R4 are as defined in the description and claims, and pharmaceutically acceptable salts thereof, for use as therapeutically active substances. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB 1 receptors.

  本发明涉及式（I）的化合物，其中R1、R2、R3和R4如描述和索赔中所定义，并其药用盐，用作治疗活性物质。这些化合物可用于与CB 1受体调节相关的疾病的治疗和/或预防。
• Process for preparation of alkoxybenzamides and thiazolyl isocyanates
  申请人：Awano Hirokazu

  公开号：US20050143581A1

  公开（公告）日：2005-06-30

  An alkoxybenzamide represented by the general formula (3): (wherein R1, R2, R3, R4, and R5 independently indicate a hydrogen atom, an alkyl group having one to six carbon atoms, or an alkoxy group having one to six carbon atoms; if R3 indicates a hydrogen atom or an alkyl group having one to six carbon atoms, R1 indicates an alkoxy group having one to six carbon atoms and R4 indicates an alkyl or alkoxy group having one to six carbon atoms; two adjacent substituents may be coupled with a cross-linking group to form a ring; R6 indicates a heteroaromatic ring; and A indicates an oxygen atom or a sulfur atom) is produced by reacting an alkoxybenzene represented by the general formula (1): (wherein R1, R2, R3, R4, and R5 are defined above) with an isocyanate represented by the general formula (2): (wherein R6 and A are defined above; and n indicates 1 or 2) in the presence of a Lewis acid. Among isocyanates represented by the general formula (2) is a thiazolyl isocyanate represented by the general formula (5): (wherein R1 indicates a hydrogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxy group having one to six carbon atoms, an alkoxycarbonyl group, or an acyl group; R2 indicates a hydrogen atom, a halogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxycarbonyl group having one to six carbon atoms, an acyl group, or a substituted or unsubstituted phenyl group; both R1 and R2 do not indicate a hydrogen atom; and n indicates 1 or 2). This thiazolyl isocyanate is produced from two precursors: an aminothiazole and a carbonyl halide. The present invention can provide a method for producing a high yield of alkoxybenzamide with fewer steps, and can also provide thiazolyl isocyanates, which are useful in the production of ureas, carbamates, and aromatic amides having a thiazole ring.

  通式（3）表示的烷氧基苯甲酰胺：（其中R1、R2、R3、R4和R5独立地表示氢原子、具有1至6个碳原子的烷基或具有1至6个碳原子的烷氧基；如果R3表示氢原子或具有1至6个碳原子的烷基，则R1表示具有1至6个碳原子的烷氧基，R4表示具有1至6个碳原子的烷基或烷氧基；两个相邻的取代基可以与交联基耦合形成环；R6表示杂环芳烃环；A表示氧原子或硫原子），通过在路易斯酸的存在下将通式（1）表示的烷氧基苯与通式（2）表示的异氰酸酯反应而制得：（其中R1、R2、R3、R4、R5、R6和A的定义如上；n表示1或2）。通式（2）表示的异氰酸酯中包括通式（5）表示的噻唑基异氰酸酯：（其中R1表示氢原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧基、烷氧羰基、或酰基；R2表示氢原子、卤素原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧羰基、酰基或取代或未取代的苯基；R1和R2均不表示氢原子；n表示1或2）。该噻唑基异氰酸酯由两个前体物质产生：氨基噻唑和羰基卤化物。本发明可以提供一种生产高产率烷氧基苯甲酰胺的方法，步骤更少，也可以提供噻唑基异氰酸酯，其在尿素、氨基甲酸酯和带有噻唑环的芳香酰胺的生产中有用。
• Thiazole derivatives
  申请人：Nettekoven Heinrich Matthias

  公开号：US20050153962A1

  公开（公告）日：2005-07-14

  The present invention relates to compounds of formula (I) wherein R 1 , R 2 , R 3 and R 4 are as defined in the description and claims, and pharmaceutically acceptable salts thereof, for use as therapeutically active substances. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors, including obesity.

  本发明涉及式(I)的化合物，其中R1，R2，R3和R4如描述和要求中所定义，并且其药学上可接受的盐，用作治疗活性物质。这些化合物对于治疗和/或预防与CB1受体调节相关的疾病，包括肥胖症，是有用的。
• PROCESS FORPREPARATION OF ALKOXYBENZAMIDES AND THIAZOLYL ISOCYANATES
  申请人：MITSUI CHEMICALS, INC.

  公开号：EP1489073A1

  公开（公告）日：2004-12-22

  An alkoxybenzamide represented by the general formula (3): (wherein R1, R2, R3, R4, and R5 independently indicate a hydrogen atom, an alkyl group having one to six carbon atoms, or an alkoxy group having one to six carbon atoms; if R3 indicates a hydrogen atom or an alkyl group having one to six carbon atoms, R1 indicates an alkoxy group having one to six carbon atoms and R4 indicates an alkyl or alkoxy group having one to six carbon atoms; two adjacent substituents may be coupled with a cross-linking group to form a ring; R6 indicates a heteroaromatic ring; and A indicates an oxygen atom or a sulfur atom) is produced by reacting an alkoxybenzene represented by the general formula (1): (wherein R1, R2, R3, R4, and R5 are defined above) with an isocyanate represented by the general formula (2):         R6―N=C=A     (2) (wherein R6 and A are defined above; and n indicates 1 or 2) in the presence of a Lewis acid. Among isocyanates represented by the general formula (2) is a thiazolyl isocyanate represented by the general formula (5): (wherein R1 indicates a hydrogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxy group having one to six carbon atoms, an alkoxycarbonyl group, or an acyl group; R2 indicates a hydrogen atom, a halogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxycarbonyl group having one to six carbon atoms, an acyl group, or a substituted or unsubstituted phenyl group; both R1 and R2 do not indicate a hydrogen atom; and n indicates 1 or 2). This thiazolyl isocyanate is produced from two precursors: an aminothiazole and a carbonyl halide. The present invention can provide a method for producing a high yield of alkoxybenzamide with fewer steps, and can also provide thiazolyl isocyanates, which are useful in the production of ureas, carbamates, and aromatic amides having a thiazole ring.

  由通式(3)代表的烷氧基苯甲酰胺： (其中 R1、R2、R3、R4 和 R5 分别独立地表示氢原子、具有 1 至 6 个碳原子的烷基或具有 1 至 6 个碳原子的烷氧基；如果 R3 表示氢原子或具有 1 至 6 个碳原子的烷基，R1 表示具有 1 至 6 个碳原子的烷氧基，R4 表示具有 1 至 6 个碳原子的烷基或烷氧基；相邻的两个取代基可与交联基团结合形成环；R6 表示杂芳香环；A 表示氧原子或硫原子）通过与通式（1）所代表的烷氧基苯反应而制得： (其中 R1、R2、R3、R4 和 R5 如上定义）与通式(2)所代表的异氰酸酯反应而制得： R6-N=C=A (2) (其中 R6 和 A 如上定义；n 表示 1 或 2）在路易斯酸存在下进行反应。在通式（2）所代表的异氰酸酯中，有通式（5）所代表的噻唑基异氰酸酯： (其中 R1 表示氢原子、具有 1 至 6 个碳原子的饱和或不饱和烷基、具有 1 至 6 个碳原子的卤代烷基、具有 1 至 6 个碳原子的烷氧基、烷氧羰基或酰基；R2 表示氢原子、卤素原子、具有 1 至 6 个碳原子的饱和或不饱和烷基、具有 1 至 6 个碳原子的卤代烷基、具有 1 至 6 个碳原子的烷氧羰基、酰基或取代或未取代的苯基；R1 和 R2 均不表示氢原子；n 表示 1 或 2）。这种噻唑基异氰酸酯由两种前体生成：氨基噻唑和羰基卤化物。本发明可以提供一种以较少步骤生产高产率烷氧基苯甲酰胺的方法，还可以提供噻唑基异氰酸酯，这种异氰酸酯可用于生产具有噻唑环的脲类、氨基甲酸酯和芳香族酰胺。
• Compounds affecting glucokinase
  申请人：AstraZeneca AB

  公开号：EP1529530A1

  公开（公告）日：2005-05-11

  The invention relates to compounds of Formula (IIb) or a salt or solvate thereof, wherein R4, R3, X and Z1 are as described in the specification, pharmaceutical compositions containing them, their use in the preparation of a medicament for the treatment or prevention of a disease condition mediated through glucokinase (GLK), such as type 2 diabetes, and methods for their preparation.

  本发明涉及式（IIb）化合物或其盐或溶液（其中 R4、R3、X 和 Z1 如说明书所述）、含有它们的药物组合物、它们在制备用于治疗或预防通过葡萄糖激酶（GLK）介导的疾病（如 2 型糖尿病）的药物中的用途，以及它们的制备方法。