咪唑并[1,5-a]吡啶-8-羧酸乙酯 | 697739-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 咪唑并[1,5-a]吡啶-8-羧酸乙酯
• 英文名称: ethyl imidazo[1,5-a]pyridine-8-carboxylate
• CAS: 697739-12-1
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: IZZCPMXJHNYFKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

反应信息

• 作为反应物：
  描述：

  咪唑并[1,5-a]吡啶-8-羧酸乙酯 在 水 作用下， 以 氢氧化钾 、 甲醇 为溶剂， 反应 0.08h， 以to give imidazo[1,5-a]pyridine-8-carboxylic acid (80 mg) as a yellow solid的产率得到咪唑并[1,5-A]吡啶-8-甲酸
  参考文献：
  名称：

  Derivatives of n-(1h-indazolyl)-and n-(1h-indolyl)-urea as well as related compounds as modulators of the vanilloid-1 receptor (vr1) for treatment of pain

  摘要：

  式(I)的化合物：其中A、B和D分别为C、N、O或S；E为C或N；五元环内的点圈表示该环可能不饱和或部分饱和；R1为卤素、羟基、C1-6烷基、卤代C1-6烷基、羟基C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、羟基C1-6烷氧基、C3-7环烷基、C3-5环烷基C1-4烷基、NR7R8、C1-6烷基取代的NR7R8、C1-6烷氧基取代的NR7R8、氧代、氰基、SO2NR7R8、CONR7R8、NHCOR9或NHSO2R9；R2为卤素、羟基、C1-6烷基、卤代C1-6烷基、羟基C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、羟基C1-6烷氧基、C3-7环烷基、C3-5环烷基C1-4烷基、NR7R8、C1-6烷基取代的NR7R8、C1-6烷氧基取代的NR7R8、氰基、SON2R7R8、CONR7R8、NHCOR9或NHSO2R9；R3和R4分别独立地为氢、C1-6烷基、苯基或卤代苯基；R5和R6在每次出现时独立地为氢、C1-6烷基、苯基、卤代苯基或羧基；X为氧或硫原子；Y为芳基、杂芳基、碳环基或融合碳环基基团；n为零或1至3的整数；p为零或1至4的整数；q为零或1至3的整数；其他取代基在权利要求中定义；在治疗疼痛和其他通过调节vanilloid-1受体（VR1）功能改善的疾病中特别有用的治疗化合物。

  公开号：

  US20070078156A1
• 作为产物：
  描述：

  烟酸乙酯 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 乙酸酐 、 间氯过氧苯甲酸 、 二甲氨基甲酰氯 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 71.0h， 生成 咪唑并[1,5-a]吡啶-8-羧酸乙酯
  参考文献：
  名称：

  [EN] SUBSTITUTED BENZALDEHYDE COMPOUNDS AND METHODS FOR THEIR USE IN INCREASING TISSUE OXYGENATION
  [FR] COMPOSÉS BENZALDÉHYDE SUBSTITUÉS ET PROCÉDÉS D'UTILISATION DE CEUX-CI DANS L'AUGMENTATION DE L'OXYGÉNATION DES TISSUS

  摘要：

  提供了替代苯甲醛及其衍生物，其作为血红蛋白的变构调节剂，以及其制备的方法和中间体，包括这些调节剂的药物组合物，以及在治疗由血红蛋白介导的疾病和需要增加组织氧合的疾病中使用它们的方法。

  公开号：

  WO2013102142A1

文献信息

• 1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS
  申请人：H. Lundbeck A/S

  公开号：US20190194189A1

  公开（公告）日：2019-06-27

  The present invention provides 1H-pyrazolo[4,3-b]pyridines of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.

  本发明提供了式(I)的1H-吡唑并[4,3-b]吡啶类化合物作为PDE1抑制剂，并将其用作药物，特别用于治疗神经退行性疾病和精神疾病。
• SUBSTITUTED HETEROARYL ALDEHYDE COMPOUNDS AND METHODS FOR THEIR USE IN INCREASING TISSUE OXYGENATION
  申请人：Global Blood Therapeutics, Inc.

  公开号：US20150344483A1

  公开（公告）日：2015-12-03

  Provided are substituted heteroaryl aldehydes and derivatives thereof that act as allosteric modulators of hemoglobin, methods and intermediates for their preparation, pharmaceutical compositions comprising the modulators, and methods for their use in treating disorders mediate by hemoglobin and disorders that would benefit from increased tissue oxygenation.

  提供了替代杂环芳醛及其衍生物，其作为血红蛋白的变构调节剂，以及其制备的方法和中间体，包括这些调节剂的药物组合物，以及在治疗由血红蛋白介导的疾病和需要增加组织氧合的疾病中使用它们的方法。
• [EN] SUBSTITUTED HETEROARYL ALDEHYDE COMPOUNDS AND METHODS FOR THEIR USE IN INCREASING TISSUE OXYGENATION<br/>[FR] COMPOSÉS D'ALDÉHYDES HÉTÉROARYLES SUBSTITUÉS ET LEURS PROCÉDÉS D'UTILISATION DANS L'ACCROISSEMENT DE L'OXYGÉNATION TISSULAIRE
  申请人：GLOBAL BLOOD THERAPEUTICS INC

  公开号：WO2013102145A1

  公开（公告）日：2013-07-04

  Provided are substituted heteroaryl aldehydes and derivatives thereof that act as allosteric modulators of hemoglobin, methods and intermediates for their preparation, pharmaceutical compositions comprising the modulators, and methods for their use in treating disorders mediate by hemoglobin and disorders that would benefit from increased tissue oxygenation.

  提供了替代杂环芳醛及其衍生物，其作为血红蛋白的变构调节剂，以及其制备的方法和中间体，包括这些调节剂的药物组合物，以及在治疗由血红蛋白介导的疾病和需要增加组织氧合的疾病中使用它们的方法。
• [EN] AMINO-HETEROCYCLES AS VR-1 ANTAGONISTS FOR TREATING PAIN<br/>[FR] HETEROCYCLES AMINES EN TANT QU'ANTAGONISTES DU RECEPTEUR VANILLOIDE (VR-1) POUR LE TRAITEMENT DE LA DOULEUR
  申请人：MERCK SHARP & DOHME

  公开号：WO2004046133A1

  公开（公告）日：2004-06-03

  the present invention provides a compound of formula (I): wherein V represents NR5, O, S, SO or S(O)2; W and X each independently represent CH or N; Y represents N, CH or C-Ar2, with the proviso that at least one, but no more than two, of W, X and Y are N; Z represents CH or C-Ar2, with the proviso that when Y is N or CH then Z is C-Ar2, and with the further proviso that when Y is C-Ar2 then Z is CH; Ar1 represents a fused 9 or 10 membered heterobicyclic ring system containing one, two, three or four heteroatoms selected from nitrogen, oxygen and sulfur, wherein at least one of the rings in said ring system is aromatic; Ar2 represents an aromatic ring selected from phenyl, pyridyl, pyrimidinyl and pyridazinyl which is optionally fused and substituted; R1 represents halogen, hydroxy, oxo, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, haloC1-6alkyl, hydroxyC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy, hydroxyC1-6alkoxy, C3-7cycloalkyl, C3-7cycloalkoxy, C3-5cycloalkylC1-4alkyl, cyano, nitro, SR6, SOR6, SO2R6, COR6, NR3COR6, CONR3R4, NR3SO2R6, SO2NR3R4, -(CH2)mcarboxy, esterified -(CH2)mcarboxy or -(CH2)mNR3R4; R2 represents hydrogen, halogen, hydroxy, C1-6alkyl, haloC1-6alkyl, C3-7cycloalkyl, C1-6alkoxy, haloC1-6alkoxy, unsubstituted phenyl or phenyl substituted with one or two groups selected from halogen, C1-6alkyl, haloC1-6alkyl, C3-7cycloalkyl, C1-6alkoxy or haloC1-6alkoxy; R3 and R4 are each independently hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-7cycloalkyl or fluoroC1-6alkyl; or R3 and R4 and the nitrogen atom to which they are attached together form a heteroaliphatic ring of 4 to 7 ring atoms, optionally substituted by one or two groups selected from hydroxy or C1-4alkoxy, which ring may optionally contain as one of the said ring atoms an oxygen or a sulfur atom, S(O), S(O)2, or NR5; R5 represents hydrogen, C1-4alkyl, hydroxyC1-4alkyl or C1-4alkoxyC1-4alkyl; R6 represents hydrogen, C1-6alkyl, fluoroC1-6alkyl, C3-7cycloalkyl, unsubstituted phenyl, or phenyl substituted with one or two groups selected from halogen, C1-6alkyl, haloC1-6alkyl, C3-7cycloalkyl, C1-6alkoxy or haloC1-6alkoxy; m is either zero or an integer from 1 to 4; n is either zero or an integer from 1 to 3; or a pharmaceutically acceptable salt, N-oxide or a prodrug thereof; a pharmaceutical composition comprising it; its use in methods of treatment; use of it for the manufacture of a medicament for treating VR-1 related conditions such as those in which pain and/or inflammation predominate; and methods of treatment using it.

  本发明提供了一种具有以下结构的化合物（I）：其中V代表NR5、O、S、SO或S(O)2；W和X分别独立地代表CH或N；Y代表N、CH或C-Ar2，但至少有一个但不超过两个W、X和Y为N；Z代表CH或C-Ar2，但当Y为N或CH时，则Z为C-Ar2，并进一步规定当Y为C-Ar2时，Z为CH；Ar1代表包含一个、两个、三个或四个从氮、氧和硫中选择的杂原子的融合的9或10成员杂双环系统，其中所述环系中的至少一个环是芳香的；Ar2代表选择自苯基、吡啶基、嘧啶基和吡啶嗪基的芳香环，可以是可选地融合和取代的；R1代表卤素、羟基、氧、C1-6烷基、C2-6烯基、C2-6炔基、卤代C1-6烷基、羟基C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、羟基C1-6烷氧基、C3-7环烷基、C3-7环烷氧基、C3-5环烷基C1-4烷基、氰基、硝基、SR6、SOR6、SO2R6、COR6、NR3COR6、CONR3R4、NR3SO2R6、SO2NR3R4、-(CH2)m羧基、酯化的-( )m羧基或-( )mNR3R4；R2代表氢、卤素、羟基、C1-6烷基、卤代C1-6烷基、C3-7环烷基、C1-6烷氧基、卤代C1-6烷氧基、未取代的苯基或苯基，其上取代有一个或两个从卤素、C1-6烷基、卤代C1-6烷基、C3-7环烷基、C1-6烷氧基或卤代C1-6烷氧基中选择的基团；R3和R4各自独立地代表氢、C1-6烷基、C2-6烯基、C2-6炔基、C3-7环烷基或氟代C1-6烷基；或R3和R4和它们连接的氮原子共同形成一个由4到7个环原子组成的杂原烷环，可选地取代为一个或两个从羟基或C1-4烷氧基中选择的基团，该环可能可选地包含作为所述环原子之一的氧或硫原子、S(O)、S(O)2或NR5；R5代表氢、C1-4烷基、羟基C1-4烷基或C1-4烷氧基C1-4烷基；R6代表氢、C1-6烷基、氟代C1-6烷基、C3-7环烷基、未取代的苯基或苯基，其上取代有一个或两个从卤素、C1-6烷基、卤代C1-6烷基、C3-7环烷基、C1-6烷氧基或卤代C1-6烷氧基中选择的基团；m为零或从1到4的整数；n为零或从1到3的整数；或其药学上可接受的盐、N-氧化物或前药；包含它的药物组合物；其在治疗方法中的用途；用于制造用于治疗VR-1相关病症的药物，例如疼痛和/或炎症占优势的病症的用途；以及使用它的治疗方法。
• Amino-heterocycles as vr-1 antagonists for treating pain
  申请人：Blurton Peter

  公开号：US20060040947A1

  公开（公告）日：2006-02-23

  the present invention provides a compound of formula (I): wherein V represents NR 5 , O, S, SO or S(O) 2 ; W and X each independently represent CH or N; Y represents N, CH or C—Ar 2 , with the proviso that at least one, but no more than two, of W, X and Y are N; Z represents CH or C—Ar 2 , with the proviso that when Y is N or CH then Z is C—Ar 2 , and with the further proviso that when Y is C—Ar 2 then Z is CH; Ar 1 represents a fused 9 or 10 membered heterobicyclic ring system containing one, two, three or four heteroatoms selected from nitrogen, oxygen and sulfur, wherein at least one of the rings in said ring system is aromatic; Ar 2 represents an aromatic ring selected from phenyl, pyridyl, pyrimidinyl and pyridazinyl which is optionally fused and substituted; R 1 represents halogen, hydroxy, oxo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, haloC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-6 alkoxy, haloC 1-6 alkoxy, hydroxyC 1-6 alkoxy, C 3-7 cycloalkyl, C 3-7 cycloalkoxy, C 3-5 cycloalkylC 1-4 alkyl, cyano, nitro, SR 6 , SOR 6 , SO 2 R 6 , COR 6 , NR 3 COR 6 , CONR 3 R 4 , NR 3 SO 2 R 6 , SO 2 NR 3 R 4 , —(CH 2 ) m carboxy, esterified —(CH 2 ) m carboxy or —(CH 2 ) m NR 3 R 4 ; R 2 represents hydrogen, halogen, hydroxy, C 1-6 alkyl, haloC 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkoxy, haloC 1-6 alkoxy, unsubstituted phenyl or phenyl substituted with one or two groups selected from halogen, C 1-6 alkyl, haloC 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkoxy or haloC 1-6 alkoxy; R 3 and R 4 are each independently hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl or fluoroC 1-6 alkyl; or R 3 and R 4 and the nitrogen atom to which they are attached together form a heteroaliphatic ring of 4 to 7 ring atoms, optionally substituted by one or two groups selected from hydroxy or C 1-4 alkoxy, which ring may optionally contain as one of the said ring atoms an oxygen or a sulfur atom, S(O), S(O) 2 , or NR 5 ; R 5 represents hydrogen, C 1-4 alkyl, hydroxyC 1-4 alkyl or C 1-4 alkoxyC 1-4 alkyl; R 6 represents hydrogen, C 1-6 alkyl, fluoroC 1-6 alkyl, C 3-7 cycloalkyl, unsubstituted phenyl, or phenyl substituted with one or two groups selected from halogen, C 1-6 alkyl, haloC 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkoxy or haloC 1-6 alkoxy; m is either zero or an integer from 1 to 4; n is either zero or an integer from 1 to 3; or a pharmaceutically acceptable salt, N-oxide or a prodrug thereof; a pharmaceutical composition comprising it; its use in methods of treatment; use of it for the manufacture of a medicament for treating VR-1 related conditions such as those in which pain and/or inflammation predominate; and methods of treatment using it.

  本发明提供了一种化合物，其化学式为（I）：其中V代表NR5、O、S、SO或S（O）2；W和X各自独立地代表CH或N；Y代表N、CH或C-Ar2，但至少有一个，但不超过两个，W、X和Y是N；Z代表CH或C-Ar2，但当Y为N或CH时，Z为C-Ar2，且进一步规定当Y为C-Ar2时，Z为CH；Ar1代表一个融合的9或10个成员的杂双环环系统，其中包含从氮、氧和硫中选择的一个、两个、三个或四个杂原子，其中至少一个环为芳香环；Ar2代表一种芳香环，选择自苯基、吡啶基、嘧啶基和吡啶嗪基，可选地融合和取代；R1代表卤素、羟基、氧代、C1-6烷基、C2-6烯基、C2-6炔基、卤代C1-6烷基、羟基C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、羟基C1-6烷氧基、C3-7环烷基、C3-7环烷氧基、C3-5环烷基C1-4烷基、氰基、硝基、SR6、SOR6、SO2R6、COR6、NR3COR6、CONR3R4、NR3SO2R6、SO2NR3R4、-(CH2)m羧基、酯化的-( )m羧基或-( )mNR3R4；R2代表氢、卤素、羟基、C1-6烷基、卤代C1-6烷基、C3-7环烷基、C1-6烷氧基、卤代C1-6烷氧基、未取代苯基或取代一个或两个群的苯基，所述群从卤素、C1-6烷基、卤代C1-6烷基、C3-7环烷基、C1-6烷氧基或卤代C1-6烷氧基中选择；R3和R4各自独立地代表氢、C1-6烷基、C2-6烯基、C2-6炔基、C3-7环烷基或氟代C1-6烷基；或R3和R4及它们所连接的氮原子一起形成4至7个环原子的杂脂环，可选地取代一个或两个群，所述群从羟基或C1-4烷氧基中选择，该环可以选择地包含一个氧原子或硫原子、S（O）、S（O）2或NR5作为其中一个所述环原子；R5代表氢、C1-4烷基、羟基C1-4烷基或C1-4烷氧基C1-4烷基；R6代表氢、C1-6烷基、氟代C1-6烷基、C3-7环烷基、未取代苯基或取代一个或两个群的苯基，所述群从卤素、C1-6烷基、卤代C1-6烷基、C3-7环烷基、C1-6烷氧基或卤代C1-6烷氧基中选择；m为零或1至4的整数；n为零或1至3的整数；或其药学上可接受的盐、N-氧化物或前药；包含它的制药组合物；它在治疗方法中的用途；用于制造治疗VR-1相关疾病的药物，例如疼痛和/或炎症占主导地位的疾病；以及使用它的治疗方法。