4-(dimethylcarbamothioyl)oxy-2-methyl-thiazole-5-carboxylic acid ethyl ester | 943994-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(dimethylcarbamothioyl)oxy-2-methyl-thiazole-5-carboxylic acid ethyl ester
• 英文别名: 4-(Dimethyl-carbamothioyl)oxy-2-methyl-thiazole-5-carboxylic acid ethyl ester；ethyl 4-(dimethylcarbamothioyloxy)-2-methyl-1,3-thiazole-5-carboxylate
• CAS: 943994-55-6
• 化学式: C₁₀H₁₄N₂O₃S₂
• 分子量: 274.365
• InChiKey: QSRFLEMQDWSQFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(dimethylcarbamothioyl)oxy-2-methyl-thiazole-5-carboxylic acid ethyl ester 在 sodium hydride 作用下， 以 mineral oil 为溶剂， 反应 17.0h， 生成 methyl 2-methyl-4-sulfanylthiazole-5-carboxylate
  参考文献：
  名称：

  Optimization of Brain Penetrant 11β-Hydroxysteroid Dehydrogenase Type I Inhibitors and in Vivo Testing in Diet-Induced Obese Mice

  摘要：

  11 beta-Hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) has been widely considered by the pharmaceutical industry as a target to treat metabolic syndrome in type II diabetics. We hypothesized that central nervous system (CNS) penetration might be required to see efficacy. Starting from a previously reported pyrimidine compound, we removed hydrogen-bond donors to yield 3, which had modest CNS penetration. More significant progress was achieved by changing the core to give 40, which combines good potency and CNS penetration. Compound 40 was dosed to diet-induced obese (DIO) mice and gave excellent target engagement in the liver and high free exposures of drug, both peripherally and in the CNS. However, no body weight reduction or effects on glucose or insulin were observed in this model. Similar data were obtained with a structurally diverse thiazole compound 51. This work casts doubt on the hypothesis that localized tissue modulation of 11 beta-HSD1 activity alleviates metabolic syndrome.

  DOI：

  10.1021/jm4016729
• 作为产物：
  描述：

  2-溴-2-乙基-丙二酸二乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.0h， 生成 4-(dimethylcarbamothioyl)oxy-2-methyl-thiazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  SPECIFIC CARBOXAMIDES AS KCNQ2/3 MODULATORS

  摘要：

  这项发明涉及特定的羧酰胺，涉及它们的制备过程，包括这些化合物的药物以及这些化合物在药物制备中的应用。

  公开号：

  US20140148468A1

文献信息

• [EN] SPECIFIC CARBOXAMIDES AS KCNQ2/3 MODULATORS<br/>[FR] CARBOXAMIDES SPÉCIFIQUES UTILISÉS EN TANT QUE MODULATEURS DES CANAUX KCNQ2/3
  申请人：GRUENENTHAL CHEMIE

  公开号：WO2014082737A1

  公开（公告）日：2014-06-05

  The invention relates to specific carboxamides of formula (I) as KCNQ2/3 modulators, to processes for their preparation, to medicaments comprising these compounds and to the use of these compounds in the preparation of medicaments.

  该发明涉及公式（I）的特定羧酰胺作为KCNQ2/3调节剂，涉及其制备方法，包括这些化合物的药物以及这些化合物在药物制备中的应用。
• Herbicidal thiazole derivatives
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04943312A1

  公开（公告）日：1990-07-24

  Certain N-[(heterocyclic)aminocarbonyl]thiazolesulfonamides, such as N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-4-thiazolesulfonamide, are useful as herbicides and/or plant growth regulants.

  某些N-[(杂环)氨基甲酰基]噻唑磺胺类化合物，例如N-[(4-甲氧基-6-甲基嘧啶-2-基)氨基甲酰基]-4-噻唑磺胺，可用作除草剂和/或植物生长调节剂。
• Fused Heterocyclic Compounds and Their Use as Mineralocorticoid Receptor Ligands
  申请人：Fukumoto Shoji

  公开号：US20090253687A1

  公开（公告）日：2009-10-08

  The present invention relates to wherein each symbol is as defined in the specification. The compound has a superior mineral corticoidreceptorantagonistic action and is useful as an agent for the prophylaxis or treatment of hypertension, cardiac failure and the like, a compound having a fused heterocycle, or a prodrug thereof, or a salt thereof; and an agent for the prophylaxis or treatment of hypertension, cardiac failure and the like.

  本发明涉及其中每个符号如规范所定义的化合物，该化合物具有优越的矿物质皮质激素受体拮抗作用，可作为预防或治疗高血压、心力衰竭等药物，包括具有融合杂环的化合物、其前药或其盐；以及预防或治疗高血压、心力衰竭等疾病的药剂。
• Specific carboxamides as KCNQ2/3 modulators
  申请人：GRÜNENTHAL GMBH

  公开号：US09284286B2

  公开（公告）日：2016-03-15

  The invention relates to specific carboxamides, to processes for their preparation, to medicaments comprising these compounds and to the use of these compounds in the preparation of medicaments.

  本发明涉及特定的羧酰胺、其制备方法、包含这些化合物的药物以及这些化合物在制备药物方面的使用。
• Herbicidal imidazole, pyrazole, thiazole and isothiazole derivatives
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0095925A2

  公开（公告）日：1983-12-07

  Compounds of the formula wherein R is H or CH3; Q is an optionally substituted imidazole, pyrazole, thiazole or isothiazole moiety; A is a heterocyclic group, e.g. pyrimidin-2-yl; and their agriculturally suitable salts, exhibit herbicidal and plant growth regulant effects. The compounds may be formulated for use in conventional manner. They may be made by various methods, e.g. by the reaction of a sulfonyl isocyanate QS02NCO with an aminoheterocycle HN(R)A.

  式中的化合物 其中 R 是 H 或 CH3； Q 是任选取代的咪唑、吡唑、噻唑或异噻唑分子； A 是杂环基团，如嘧啶-2-基；以及它们在农业上适用的盐类，具有除草和植物生长调节作用。 这些化合物可按常规方法配制使用。它们可以通过各种方法制成，例如通过磺酰基异氰酸酯 QS02NCO 与氨基杂环 HN(R)A 的反应。