4-acetoxy-5-(4-chloro-phenyl)-1-(2-chloro-phenyl)-1H-pyrazole-3-carboxylic acid | 851729-01-6

• 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-acetoxy-5-(4-chloro-phenyl)-1-(2-chloro-phenyl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 4-Acetoxy-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid；4-acetyloxy-1-(2-chlorophenyl)-5-(4-chlorophenyl)pyrazole-3-carboxylic acid
• CAS: 851729-01-6
• 化学式: C₁₈H₁₂Cl₂N₂O₄
• 分子量: 391.21
• InChiKey: YERYKYZTWPSPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetoxy-5-(4-chloro-phenyl)-1-(2-chloro-phenyl)-1H-pyrazole-3-carboxylic acid 、 (R)-1-[4-(三氟甲基)苯基]乙胺 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 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 {1-(2-chloro-phenyl)-5-(4-chloro- phenyl)-3-[(R)-1-(4-trifluoromethyl-phenyl)-ethylcarbamoyl]-1H-pyrazol-4-yloxy}-acetic acid ester
  参考文献：
  名称：

  WO2008/75012

  摘要：

  公开号：
• 作为产物：
  描述：

  1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid 、 乙酸酐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.33h， 以94%的产率得到4-acetoxy-5-(4-chloro-phenyl)-1-(2-chloro-phenyl)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Process for Preparing Bicyclic Pyrazolyl

  摘要：

  本文描述了一种制备化合物式（I）的方法。这些化合物已被证明可作为大麻素受体配体，并因此在治疗与动物体内大麻素受体介导有关的疾病中具有用途。

  公开号：

  US20070260056A1

文献信息

• Bicyclic pyrazolyl and imidazolyl compounds and uses thereof
  申请人：Carpino A. Philip

  公开号：US20050101592A1

  公开（公告）日：2005-05-12

  Compounds of Formula (I) are described herein. The compounds have been shown to act as cannabinoid receptor ligands and are therefore useful in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals.

  本文描述了化学式（I）的化合物。已经证明这些化合物可以作为大麻素受体配体，并且因此在治疗与动物体内大麻素受体介导相关的疾病方面是有用的。
• 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。
• BICYCLIC PYRAZOLYL AND IMIDAZOLYL COMPOUNDS AND USES THEREOF
  申请人：Carpino A. Philip

  公开号：US20070027133A1

  公开（公告）日：2007-02-01

  Compounds of Formula (I) are described herein. The compounds have been shown to act as cannabinoid receptor ligands and are therefore useful in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals.

  本文描述了公式（I）的化合物。这些化合物已被证明作为大麻素受体配体，并因此在治疗与动物中大麻素受体调节相关的疾病中具有用途。
• Modulators of CB1 Receptors
  申请人：Cooper Martin

  公开号：US20100144701A1

  公开（公告）日：2010-06-10

  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; p and q are independently 0 or 1; A3 is phenyl or cycloalkyl, either of which is optionally substituted with R 4 and/or R 5 ; R 4 and R 5 are 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 or cycloalkyl; R 9 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy(C 1 -C 4 alkyl)-, cycloalkyl, or fully or partially fluorinated C 1 -C 4 alkyl; R 1 (i) a bond; (ii) a divalent radical of formula —(CH 2 ) a B 1 (CH 2 ) b wherein a and b are independently O, 1, 2 or 3 provided that a+b is 1, 2 or 3, and B 1 is —CO—, —O—, —S—, —SO—, —SO 2 —, —CH 2 —, —CHCH 3 —, —CHOH— or —NR 7 —; or (iii) a divalent radical selected from —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 )—* and —C(R 10 )(R 11 )—O—CH 2 —*, wherein the bond indicated by an asterisk is attached to the pyrazole ring; Z is as defined in the specification; 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，因此可用于治疗由CB1受体信号活动介导的疾病或症状，例如肥胖和超重的治疗，预防体重增加，直接或间接与肥胖和超重相关的疾病和症状的治疗：其中A1是氢，-COOH或四唑基；p和q独立地为0或1；A3是苯基或环烷基，其中任一可选地用R4和/或R5取代；R4和R5独立地为-R9，-CN，-F，-Cl，-Br，-OR9，-NR7R8，-NR7COR6，-NR7SO2R6，-COR6，-SR9，-SOR9或-SO2R6；R6是C1-C4烷基，环烷基，-CF3或-NR7R8；R7和R8独立地为氢，C1-C4烷基或环烷基；R9为氢，C1-C4烷基，C1-C4烷氧基，C1-C4烷氧基（C1-C4烷基）-，环烷基或完全或部分氟化的C1-C4烷基；R1(i)为键；（ii）为式-（CH2）aB1（ ）b的二价基团，其中a和b独立地为O，1，2或3，前提是a+b为1，2或3，B1为-CO-，-O-，-S-，-SO-，-SO2-，- -，-CHCH3-，-CHOH-或-NR7-；或（iii）为从-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）- *和-C（R10）（R11）-O- - *中选择的二价基团，其中由星号表示的键连接到吡唑环；Z如规范中所定义；R10为氢，R11为（C1-C3）烷基或-OH；或R10和R11均为（C1-C3）烷基；或R10和R11与它们连接的碳原子一起形成（C3-C5）环烷基环。
• PROCESS FOR PREPARING BICYCLIC PYRAZOLYL COMPOUNDS
  申请人：Pfizer Products Inc.

  公开号：EP1797041A2

  公开（公告）日：2007-06-20