4-氮杂吲哚-3-甲酸甲酯 | 952800-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 4-氮杂吲哚-3-甲酸甲酯
• 中文别名: 4-并环化合物-3-甲酸甲酯；1H-吡咯并[3,2-B]吡啶-3-甲酸甲酯；1H-吡咯并[3,2-B]吡啶-3-羧酸甲酯
• 英文名称: methyl 1H-pyrrolo[3,2-b]pyridine-3-carboxylate
• CAS: 952800-39-4
• 化学式: C₉H₈N₂O₂
• mdl: MFCD09864655
• 分子量: 176.175
• InChiKey: LFOJQCBWPFHMJU-UHFFFAOYSA-N

物化性质

• 密度：
  1.324

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  4-氮杂吲哚-3-甲酸甲酯 在 盐酸 、 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 反应 52.5h， 生成 1-(methylsulfonyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid
  参考文献：
  名称：

  [EN] COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS ET LEURS UTILISATIONS

  摘要：

  本公开涉及用于治疗BAF复合物相关疾病的化合物。

  公开号：

  WO2020160100A1

文献信息

• [EN] PYRROLOPYRIDINE OR PYRAZOLOPYRIDINE DERIVATIVES<br/>[FR] DÉRIVÉS PYRROLOPYRIDINE OU PYRAZOLOPYRIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015028483A1

  公开（公告）日：2015-03-05

  The present invention relates to compounds of formula I wherein R1 halogen, lower alkyl, lower alkoxy, cyano, phenyl, C(O)NHCH3, C(O)NH2, lower alkyl substituted by halogen or is a five-membered heteroaryl group, optionally substituted by lower alkyl; Y1 is N or CH; Y2 is CH; and if Y1 is CH, Y1 and Y2 may form together with the C-atoms to which they are attached a ring, containing −CH=N-N(CH3)-, -CH=N-N(H)-; X is CH or N; R is (CH2)m-cycloalkyl, optionally substituted by hydroxy, lower alkoxy or lower alkyl, or is tetrahydropyran, optionally substituted by hydroxy, or is lower alkoxy, substituted by hydroxy, or is lower alkyl substituted by one or two hydroxy, or is (CH2)m-pyridinyl, optionally substituted by hydroxy, lower alkyl or lower alkyl substituted by hydroxy, or is L-phenyl, optionally substituted by hydroxy, lower alkyl or lower alkyl substituted by hydroxy, and L is a bond, -CH(CH2OH)- or −CH2CH(OH)-; n is 0, 1 or 2; m is 0 or 1; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof. The compounds of the present invention are muscarinic M1 receptor positive allosteric modulators (PAM) and hence are useful in the treatment of diseases, mediated by the muscarinic M1 receptor, such as Alzheimer's disease, cognitive impairment, schizophrenia, pain or sleep disorders.

  本发明涉及公式I的化合物，其中R1是卤素，较低的烷基，较低的烷氧基，氰基，苯基，C（O）NHCH3，C（O）NH2，被卤素取代的较低烷基或是五元杂环芳基，可选择被较低烷基取代；Y1是N或CH；Y2是CH；如果Y1是CH，则Y1和Y2可以与它们连接的C原子一起形成一个环，其中包含-CH=N-N（CH3）-，-CH=N-N（H）-；X是CH或N；R是（CH2）m-环烷基，可选择被羟基，较低烷氧基或较低烷基取代，或是四氢吡喃，可选择被羟基取代，或是被羟基取代的较低烷氧基，或是被一或两个羟基取代的较低烷基，或是（CH2）m-吡啶基，可选择被羟基，较低烷基或被羟基取代的较低烷基取代，或是L-苯基，可选择被羟基，较低烷基或被羟基取代的较低烷基取代，其中L是一个键，-CH（CH2OH）-或-CH2CH（OH）-；n是0、1或2；m是0或1；或是其对应的对映体和/或光学异构体的药学上可接受的酸加合盐或外消旋混合物。本发明的化合物是肌动蛋白M1受体正向变构调节剂（PAM），因此可用于治疗由肌动蛋白M1受体介导的疾病，例如阿尔茨海默病、认知障碍、精神分裂症、疼痛或睡眠障碍。
• DIMERIC IAP INHIBITORS
  申请人：Chen Zhuoliang

  公开号：US20130309247A1

  公开（公告）日：2013-11-21

  The present invention provides compounds of formula M-L-M′ (where M and M′ are each independently a monomeric moiety of Formula (I) and L is a linker). The dimeric compounds have been found to be effective in promoting apoptosis in rapidly dividing cells. (I)

  本发明提供了公式M-L-M'的化合物（其中M和M'分别独立地是公式（I）的单体基团，L是连接剂）。已发现二聚化合物在促进快速分裂细胞的凋亡方面具有有效性。 (I)
• PYRROLOPYRIDINE OR PYRAZOLOPYRIDINE DERIVATIVES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160194321A1

  公开（公告）日：2016-07-07

  The present invention relates to compounds of formula wherein R 1 halogen, lower alkyl, lower alkoxy, cyano, phenyl, C(O)NHCH 3 , C(O)NH 2 , lower alkyl substituted by halogen or is a five-membered heteroaryl group, optionally substituted by lower alkyl; Y 1 is N or CH; Y 2 is CH; and if Y 1 is CH, Y 1 and Y 2 may form together with the C-atoms to which they are attached a ring, containing —CH═N—N(CH 3 )—, —CH═N—N(H)—; X is CH or N; R is (CH 2 ) m -cycloalkyl, optionally substituted by hydroxy, lower alkoxy or lower alkyl, or is tetrahydropyran, optionally substituted by hydroxy, or is lower alkoxy, substituted by hydroxy, or is lower alkyl substituted by one or two hydroxy, or is (CH 2 ) m -pyridinyl, optionally substituted by hydroxy, lower alkyl or lower alkyl substituted by hydroxy, or is L-phenyl, optionally substituted by hydroxy, lower alkyl or lower alkyl substituted by hydroxy, and L is a bond, —CH(CH 2 OH)— or —CH 2 CH(OH)—; n is 0, 1 or 2; m is 0 or 1; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof. The compounds of the present invention are muscarinic M1 receptor positive allosteric modulators (PAM) and hence are useful in the treatment of diseases, mediated by the muscarinic M1 receptor, such as Alzheimer's disease, cognitive impairment, schizophrenia, pain or sleep disorders.

  本发明涉及式为的化合物，其中R1是卤素、较低的烷基、较低的烷氧基、氰基、苯基、C（O）NHCH3、C（O）NH2、被卤素取代的较低烷基或是一个五元杂环芳基基团，可选地被较低烷基取代；Y1是N或CH；Y2是CH；如果Y1是CH，则Y1和Y2可以与它们所连接的碳原子一起形成一个环，其中包含—CH═N—N（CH3）—，—CH═N—N（H）—；X是CH或N；R是（CH2）m-环烷基，可选地被羟基、较低烷氧基或较低烷基取代，或者是四氢吡喃，可选地被羟基取代，或是被羟基取代的较低烷氧基，或是被一或两个羟基取代的较低烷基，或是（CH2）m-吡啶基，可选地被羟基、较低烷基或被羟基取代的较低烷基取代，或是L-苯基，可选地被羟基、较低烷基或被羟基取代的较低烷基取代，L是一个键、—CH（CH2OH）—或—CH2CH（OH）—；n为0、1或2；m为0或1；或是其相应的对映体和/或光学异构体的药学上可接受的酸盐或其外消旋混合物。本发明的化合物是肌动蛋白M1受体正变构调节剂（PAM），因此在治疗由肌动蛋白M1受体介导的疾病，如阿尔茨海默病、认知障碍、精神分裂症、疼痛或睡眠障碍方面有用。
• Design and optimization of selective azaindole amide M 1 positive allosteric modulators
  作者：Jennifer E. Davoren、Steven V. O’Neil、Dennis P. Anderson、Michael A. Brodney、Lois Chenard、Keith Dlugolenski、Jeremy R. Edgerton、Michael Green、Michelle Garnsey、Sarah Grimwood、Anthony R. Harris、Gregory W. Kauffman、Erik LaChapelle、John T. Lazzaro、Che-Wah Lee、Susan M. Lotarski、Deane M. Nason、R. Scott Obach、Veronica Reinhart、Romelia Salomon-Ferrer、Stefanus J. Steyn、Damien Webb、Jiangli Yan、Lei Zhang

  DOI：10.1016/j.bmcl.2015.11.053

  日期：2016.1

  Selective activation of the M-1 receptor via a positive allosteric modulator (PAM) is a new approach for the treatment of the cognitive impairments associated with schizophrenia and Alzheimer's disease. A novel series of azaindole amides and their key pharmacophore elements are described. The nitrogen of the azaindole core is a key design element as it forms an intramolecular hydrogen bond with the amide N-H thus reinforcing the bioactive conformation predicted by published SAR and our homology model. Representative compound 25 is a potent and selective M-1 PAM that has well aligned physicochemical properties, adequate brain penetration and pharmacokinetic (PK) properties, and is active in vivo. These favorable properties indicate that this series possesses suitable qualities for further development and studies. (C) 2015 Elsevier Ltd. All rights reserved.
• COMPOUNDS AND USES THEREOF
  申请人：Foghorn Therapeutics Inc.

  公开号：US20220119378A1

  公开（公告）日：2022-04-21

  The present disclosure features compounds useful for the treatment of BAF complex-related disorders.