Ethyl 1,4-dimethyl-5-phenyl-1H-pyrazole-3-carboxylate | 30823-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 1,4-dimethyl-5-phenyl-1H-pyrazole-3-carboxylate
• 英文别名: ethyl 1,4-dimethyl-5-phenylpyrazole-3-carboxylate
• CAS: 30823-58-6
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: UHYWOIXVANQRHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-6-甲基吡啶 、 Ethyl 1,4-dimethyl-5-phenyl-1H-pyrazole-3-carboxylate 在 三甲基铝 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 生成 1,4-dimethyl-N-(6-methylpyridin-2-yl)-5-phenylpyrazole-3-carboxamide
  参考文献：
  名称：

  Discovery of biological evaluation of pyrazole/imidazole amides as mGlu5 receptor negative allosteric modulators

  摘要：

  Development of SAR in a 5-aryl-3-acylpyridinyl-pyrazoles and 1-aryl-4-acylpyridinyl imidazoles series of mGlu5 receptor negative allosteric modulators (mGluR5 NAMs) using a functional cell-based assay is described in this Letter. Analysis of the Ligand-lipophilic efficiency (LipE) of compounds provided new insight for the design of potent mGluR5 negative allosteric modulators with anti-depressant activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.116
• 作为产物：
  描述：

  苯丙酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 Ethyl 1,4-dimethyl-5-phenyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Discovery of biological evaluation of pyrazole/imidazole amides as mGlu5 receptor negative allosteric modulators

  摘要：

  Development of SAR in a 5-aryl-3-acylpyridinyl-pyrazoles and 1-aryl-4-acylpyridinyl imidazoles series of mGlu5 receptor negative allosteric modulators (mGluR5 NAMs) using a functional cell-based assay is described in this Letter. Analysis of the Ligand-lipophilic efficiency (LipE) of compounds provided new insight for the design of potent mGluR5 negative allosteric modulators with anti-depressant activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.116

文献信息

• CB1 RECEPTOR MODULATORS
  申请人：Cooper Martin

  公开号：US20100010061A1

  公开（公告）日：2010-01-14

  Compounds of formula (I) suppress the normal signalling activity CB1 receptors, and are thus useful in the treatment of diseases or conditions which are mediated by CB1 receptor signalling activity, such as treatment of obesity and overweight, prevention of weigh gain, treatment of diseases and conditions directly or indirectly associated with obesity and overweight: wherein A 1 is hydrogen, —COOH, or tetrazolyl, and A 2 is hydrogen, —COOH, or tetrazolyl, provided that one of A 1 and A 2 is either —COOH or tetrazolyl; p is 0 or 1 and A 3 is phenyl or cycloalkyl, either of which is optionally substituted with R 4 and/or R 5 ; q is 0 or 1; R 3 is hydrogen, C 1 -C 4 alkyl, cycloalkyl, —CF 3 , or —OR 9 ; R 4 and R 5 independently —R 9 , —CN, —F, —Cl, —Br, —OR 9 , —NR 7 R 8 , —NR 7 COR 6 , —NR 7 SO 2 R 6 , —COR 6 , —SR 9 , —SOR 9 , or —SO 2 R 6 ; R 6 is C 1 -C 4 alkyl, cycloalkyl, —CF 3 or —NR 7 R 8 ; R 7 and R 8 are independently hydrogen, C 1 -C 4 alkyl, —CF 3 , or cycloalkyl; R 9 is hydrogen, C 1 -C 4 alkyl, cycloalkyl, fully or partially fluorinated C 1 -C 4 alkyl; R 1 is (i) a bond, or (ii) —(CH 2 ) a B 1 (CH 2 ) b — wherein a and b are independently 0, 1, 2 or 3 provided that a+b is 1, 2 or 3; or (iii) —C(R 10 )(R 11 )—*, —C(R 10 )(R 11 )—O—*, —C(R 10 )(R 11 )CH 2 —*, —C(R 10 )(R 11 )CH 2 —O—*, —CH 2 C(R 10 )(R 11 )—*, —CH 2 C(R 10 )(R 11 )—O—*, —CH 2 —O—C(R 10 )(R 11 )—* or —C(R 10 )(R 11 )—O—CH 2 —*, wherein the bond indicated by an asterisk is attached to the pyrazole ring; R 2 is a divalent radical of formula -Q 1 -A 4 -[Q 2 ] w - wherein Q1, A4 Q2 and w are as defined in the specification; and R 10 is hydrogen and R 11 is (C 1 -C 3 )alkyl or —OH; or R 10 and R 11 are both (C 1 -C 3 )alkyl; or R 10 and R 11 taken together with the carbon atom to which they are attached form a (C 3 -C 5 )cycloalkyl ring.

  式(I)的化合物抑制CB1受体的正常信号活动，因此在治疗由CB1受体信号活动介导的疾病或病症方面有用，例如治疗肥胖和超重，预防体重增加，直接或间接与肥胖和超重相关的疾病和病症的治疗：其中A1是氢，-COOH或四唑基，A2是氢，-COOH或四唑基，但A1和A2中的一个是-COOH或四唑基；p为0或1，A3是苯基或环烷基，其中任一种都可以被R4和/或R5取代；q为0或1；R3是氢，C1-C4烷基，环烷基，-CF3或-OR9；R4和R5独立地是-R9，-CN，-F，-Cl，-Br，-OR9，-NR7R8，-NR7COR6，-NR7SO2R6，-COR6，-SR9，-SOR9或-SO2R6；R6是C1-C4烷基，环烷基，- 或-NR7R8；R7和R8独立地是氢，C1-C4烷基，- 或环烷基；R9是氢，C1-C4烷基，环烷基，完全或部分氟化的C1-C4烷基；R1是（i）键，或（ii）-（CH2）aB1（ ）b-，其中a和b独立地为0、1、2或3，但a+b为1、2或3；或（iii）-C（R10）（R11）- *，-C（R10）（R11）-O- *，-C（R10）（R11） - *，-C（R10）（R11） -O- *，- C（R10）（R11）- *，- C（R10）（R11）-O- *，- -O-C（R10）（R11）- *或-C（R10）（R11）-O- - *，其中星号表示连接到吡唑环的键；R2是式-Q1-A4-[Q2]w-的二价基团，其中Q1，A4，Q2和w在规范中定义；R10是氢，R11是（C1-C3）烷基或-OH；或R10和R11都是（C1-C3）烷基；或R10和R11与它们所连接的碳原子一起形成（C3-C5）环烷基环。
• AZASPIRO DERIVATIVES AS TRPM8 ANTAGONISTS
  申请人：RaQualia Pharma Inc.

  公开号：US20170002016A1

  公开（公告）日：2017-01-05

  The present invention relates to azaspiro derivatives of the formula (I) or a pharmaceutically acceptable salt thereof or a prodrug thereof, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders which are mediated via the TRPM8 receptor.
• US8124634B2
  申请人：——

  公开号：US8124634B2

  公开（公告）日：2012-02-28
• US8148404B2
  申请人：——

  公开号：US8148404B2

  公开（公告）日：2012-04-03