5-环丙基-4-甲基-4H-1,2,4-噻唑-3-硫醇 | 588687-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-环丙基-4-甲基-4H-1,2,4-噻唑-3-硫醇
• 中文别名: 5-环丙基-4-甲基-2H-1,2,4-三唑-3-硫酮；5-环丙基-4-甲基-4H-[1,2,4]三唑-3-硫醇
• 英文名称: 5-cyclopropyl-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-methyl-5-cyclopropyl-4H-[1,2,4]triazole-3-thiol；5-cyclopropyl-4-methyl-4H-[1,2,4]triazole-3-thiol；5-cyclopropyl-4-methyl-4H-1,2,4-triazole-3-thiol；3-cyclopropyl-4-methyl-1H-1,2,4-triazole-5-thione
• CAS: 588687-37-0
• 化学式: C₆H₉N₃S
• mdl: MFCD03421706
• 分子量: 155.224
• InChiKey: GJFFNHYCAAALIV-UHFFFAOYSA-N

物化性质

• 沸点：
  206.1±23.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-环丙基-4-甲基-4H-1,2,4-噻唑-3-硫醇 、 1-金刚烷基溴甲酮 以 乙腈 为溶剂， 以390 mg的产率得到1-(adamantan-1-yl)-2-[(5-cyclopropyl-4-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]ethanone
  参考文献：
  名称：

  发现作为有效 11β-羟基类固醇脱氢酶 1 型抑制剂的金刚烷基杂环酮

  摘要：

  11β-羟基类固醇脱氢酶 1 (11β-HSD1) 在将细胞内可的松转化为生理活性皮质醇方面起着关键作用，这与代谢综合征的几种表型的发展有关。用选择性抑制剂抑制 11β-HSD1 活性对包括糖尿病、血脂异常和肥胖症在内的各种疾病具有有益影响，因此构成了发现代谢和心血管疾病新疗法的有希望的策略。一系列新型金刚烷基杂环酮提供了有效且选择性的人 11β-HSD1 抑制剂。先导化合物对人和小鼠 11β-HSD1 显示出低纳摩尔抑制，并且具有选择性，对 11β-HSD2 和 17β-HSD1 没有活性。

  DOI：

  10.1002/cmdc.201100144
• 作为产物：
  描述：

  2-(cyclopropanecarbonyl)-N-methylhydrazinecarbothioamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 生成 5-环丙基-4-甲基-4H-1,2,4-噻唑-3-硫醇
  参考文献：
  名称：

  发现作为有效 11β-羟基类固醇脱氢酶 1 型抑制剂的金刚烷基杂环酮

  摘要：

  11β-羟基类固醇脱氢酶 1 (11β-HSD1) 在将细胞内可的松转化为生理活性皮质醇方面起着关键作用，这与代谢综合征的几种表型的发展有关。用选择性抑制剂抑制 11β-HSD1 活性对包括糖尿病、血脂异常和肥胖症在内的各种疾病具有有益影响，因此构成了发现代谢和心血管疾病新疗法的有希望的策略。一系列新型金刚烷基杂环酮提供了有效且选择性的人 11β-HSD1 抑制剂。先导化合物对人和小鼠 11β-HSD1 显示出低纳摩尔抑制，并且具有选择性，对 11β-HSD2 和 17β-HSD1 没有活性。

  DOI：

  10.1002/cmdc.201100144

文献信息

• [EN] 4-PIPERAZINYL-PYRIMIDINE COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSÉS DE 4-PIPÉRAZINYLPYRIMIDINE CONVENANT POUR TRAITER DES TROUBLES QUI RÉPONDENT À UNE MODULATION DU RÉCEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006015842A1

  公开（公告）日：2006-02-16

  The present invention relates to novel 4-piperazinylpyrimidine compounds. The compounds possess valuable therapeutic properties and are suitable, in particular, for treating diseases that respond to modulation of the dopamine D3 receptor. The 4­ piperzinylpyrimidine compounds have the general formula (I), wherein Ar, X, A, R1 and R1a are as defined in the claims.

  本发明涉及新颖的4-哌嗪基嘧啶化合物。这些化合物具有有价值的治疗特性，特别适用于治疗对多巴胺D3受体调节产生反应的疾病。4-哌嗪基嘧啶化合物具有通式(I)，其中Ar、X、A、R1和R1a如权利要求中所定义。
• Novel Compounds
  申请人：Arista Luca

  公开号：US20080227837A1

  公开（公告）日：2008-09-18

  The present invention relates to novel compounds of formula (I) or a pharmaceutically acceptable salt thereof: wherein G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl, indazolyl; p is an integer ranging from 0 to 5; R 1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 5 ; R 2 is hydrogen or C 1-4 alkyl; R 3 is C 1-4 alkyl; R 4 is C 1-4 alkyl or C 1-6 cycloalkyl optionally substituted by 1 or 2 substituents selected from the group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; R 5 is a moiety selected from the group consisting of: isoxazolyl, —CH 2 —N-pyrrolyl, 1,1 -dioxido- 2 -isothiazolidinyl, thienyl, thiazolyl, pyridyl, 2 -pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D 3 receptors, as antipsychotic agents, or to treat obsessive compulsive spectrum disorders or premature ejaculation.

  本发明涉及公式（I）的新化合物或其药学上可接受的盐：其中G选择自以下组：苯基，吡啶基，苯并噻唑基，吲哚基；p是从0到5的整数；R1独立地选择自以下组：卤素，羟基，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4酰基和SF5；或对应于R5基团；R2是氢或C1-4烷基；R3是C1-4烷基；R4是C1-4烷基或C1-6环烷基，可选地被1或2个来自以下组的取代基所取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4酰基；R5是从以下组中选择的基团：异恶唑基，-CH2-N-吡咯基，1,1-二氧化-2-异硫氰酸酰基，噻唑基，噻唑啉基，吡啶基，2-吡咯烷酰基，该基团可选地被1或2个取代基所取代，所述取代基选择自：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4酰基；以及用于制备这些化合物的中间体，包含它们的制药组合物以及它们作为多巴胺D3受体调节剂、抗精神病药物或用于治疗强迫症谱系障碍或早泄的用途。
• 4-Piperazinyl-Pyrimidine Compounds Suitable for Treating Disorders that Respond to Modulation of the Dopamine D3 Receptor
  申请人：Haupt Andreas

  公开号：US20090264437A1

  公开（公告）日：2009-10-22

  The present invention relates to novel 4-piperazinylpyrimidine compounds. The compounds possess valuable therapeutic properties and are suitable, in particular, for treating diseases that respond to modulation of the dopamine D 3 receptor. The 4-piperzinylpyrimidine compounds have the general formula I wherein Ar, X, A, R 1 and R 1a are as defined in the claims.

  本发明涉及新型4-哌嗪基嘧啶化合物。这些化合物具有有价值的治疗性质，特别适用于治疗对多巴胺D3受体调节有反应的疾病。4-哌嗪基嘧啶化合物具有一般式I，其中Ar、X、A、R1和R1a如权利要求中所定义。
• Triazole Compounds Suitable for Treating Disorders that Respond to Modulation of the Dopamine D3 Receptor
  申请人：Unger Liliane

  公开号：US20080171751A1

  公开（公告）日：2008-07-17

  The invention relates to compounds of the formula I: wherein n is 1 or 2, Ar is a C-bound 1,2,4-triazol radical which carries a radical R 1 on the remaining carbon atom and a radical R 1a on one of the nitrogen atoms; R 1 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxymethyl, fluorinated C 1 -C 6 alkyl, fluorinated C 3 -C 6 cycloalkyl, fluorinated C 1 -C 4 alkoxymethyl, or optionally substituted phenyl or 5- or 6-membered heteroaryl; R 1a is hydrogen or C 1 -C 4 alkyl; and R 2 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, fluorinated C 1 -C 6 alkyl or fluorinated C 3 -C 6 cycloalkyl; and to the physiologically tolerated acid addition salts of these compounds. The invention also relates to a pharmaceutical composition that comprises at least one triazole compound of the formula I and/or at least one physiologically tolerated acid addition salt thereof, and further to a method for treating disorders that respond beneficially to dopamine D 3 receptor antagonists or dopamine D 3 agonists, said method comprising administering an effective amount of at least one triazole compound or physiologically tolerated acid addition salt of the formula I to a subject in need thereof.

  该发明涉及公式I的化合物：其中n为1或2，Ar为C-结合的1,2,4-三唑基团，在剩余碳原子上携带基团R1，并在其中一个氮原子上携带基团R1a；R1为氢、C1-C6烷基、C3-C6环烷基、C1-C4烷氧甲基、氟化C1-C6烷基、氟化C3-C6环烷基、氟化C1-C4烷氧甲基或可选取代的苯基或5-或6-成员杂环基；R1a为氢或C1-C4烷基；R2为C1-C6烷基、C3-C6环烷基、氟化C1-C6烷基或氟化C3-C6环烷基；以及这些化合物的生理耐受性酸加盐物。该发明还涉及一种制备至少一种公式I的三唑化合物和/或至少一种生理耐受性酸加盐物的制药组合物，以及一种治疗对多巴胺D3受体拮抗剂或多巴胺D3激动剂有益反应的疾病的方法，该方法包括向需要治疗的受体中给予至少一种公式I的三唑化合物或生理耐受性酸加盐物的有效剂量。
• TRIAZOLE COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR
  申请人：Unger Liliane

  公开号：US20120095015A1

  公开（公告）日：2012-04-19

  The invention relates to compounds of formula (I), wherein n is 1 or 2, Ar is a C-bound 1,2,4-triazol radical which carries a radical R 1 on the remaining carbon atom and a radical R 1a on one of the nitrogen atoms; R 1 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxymethyl, fluorinated C 1 -C 6 alkyl, fluorinated C 3 -C 6 cycloalkyl, fluorinated C 1 -C 4 alkoxymethyl, or optionally substituted phenyl or 5- or 6-membered heteroaryl; R 1a is hydrogen or C 1 -C 4 alkyl; and R 2 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, fluorinated C 1 -C 6 alkyl or fluorinated C 3 -C 6 cycloalkyl; and to the physiologically tolerated acid addition salts of there compounds. The invention also relates to a pharmaceutically composition that comprises at least one triazole compound of the formula (I) and/or at least one physiologically tolerated acid addition salt thereof, and further to a method for treating disorders that respond beneficially to dopamine D 3 receptor antagonists or dopamine D 3 agonists, said method comprising administering an effective amount of at least one triazole compound or physiologically tolerated acid addition salt of the formula (I) to a subject in need thereof.

  本发明涉及式（I）的化合物，其中n为1或2，Ar是C-连接的1,2,4-三唑基团，其在剩余碳原子上带有基团R1，并在其中一个氮原子上带有基团R1a；R1为氢，C1-C6烷基，C3-C6环烷基，C1-C4烷氧甲基，氟代C1-C6烷基，氟代C3-C6环烷基，氟代C1-C4烷氧甲基，或者可选取代的苯基或5-或6-成员杂环基；R1a为氢或C1-C4烷基；R2为C1-C6烷基，C3-C6环烷基，氟代C1-C6烷基或氟代C3-C6环烷基；以及这些化合物的生理耐受性酸加成盐。本发明还涉及一种制药组合物，其包括至少一种式（I）的三唑化合物和/或至少一种其生理耐受性酸加成盐，以及一种用于治疗对多巴胺D3受体拮抗剂或多巴胺D3激动剂有益反应的疾病的方法，该方法包括向需要的受体中注射至少一种三唑化合物或式（I）的生理耐受性酸加成盐的有效量。