tert-butyl (2S,4S)-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate | 1123305-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,4S)-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate
• 英文别名: tert-Butyl (2S,4S)-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate；tert-butyl (2S,4S)-2-methyl-4-methylsulfonyloxypyrrolidine-1-carboxylate
• CAS: 1123305-81-6
• 化学式: C₁₁H₂₁NO₅S
• 分子量: 279.357
• InChiKey: UJMCAWBIYLOHPV-IUCAKERBSA-N

物化性质

• 沸点：
  397.7±31.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4S)-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate 在 盐酸 、 10% palladium on activated charcoal 、 水 、 氢气 、 三乙胺 、 t-butyl ammonium azide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 生成 2,5-dibromo-N-[(3R,5S)-5-methylpyrrolidin-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Discovery of Novel Cyanamide-Based Inhibitors of Cathepsin C

  摘要：

  The discovery of potent and selective cyanamide-based inhibitors of the cysteine protease cathepsin C is detailed. Optimization of the template with regard to plasma stability led to the identification of compound 17, a potent cathepsin C inhibitor with excellent selectivity over other cathepsins and potent in vivo activity in a cigarette smoke mouse model.

  DOI：

  10.1021/ml100212k
• 作为产物：
  描述：

  (2R,4S)-methyl 4-hydroxypyrrolidine-2-carboxylate 在 咪唑 、 锂硼氢 、 四丁基氟化铵 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (2S,4S)-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Discovery of Novel Cyanamide-Based Inhibitors of Cathepsin C

  摘要：

  The discovery of potent and selective cyanamide-based inhibitors of the cysteine protease cathepsin C is detailed. Optimization of the template with regard to plasma stability led to the identification of compound 17, a potent cathepsin C inhibitor with excellent selectivity over other cathepsins and potent in vivo activity in a cigarette smoke mouse model.

  DOI：

  10.1021/ml100212k

文献信息

• [EN] NOVEL CATHEPSIN C INHIBITORS AND THEIR USE<br/>[FR] NOUVEAUX INHIBITEURS DE LA CATHEPSINE C ET LEUR UTILISATION
  申请人：GLAXO GROUP LTD

  公开号：WO2009026197A1

  公开（公告）日：2009-02-26

  The invention is directed to compounds according to Formula (I) wherein R1, R2a, R2b, R2c, R3, and n are defined below, and to pharmaceutically-acceptable salts thereof. They are cathepsin C inhibitors and can be used in the treatment of diseases mediated by the cathepsin C enzyme, such as COPD.

  这项发明涉及到符合以下式（I）的化合物，其中R1、R2a、R2b、R2c、R3和n的定义如下，并且其药用盐。它们是半胱氨酸蛋白酶C抑制剂，可用于治疗由半胱氨酸蛋白酶C酶介导的疾病，如慢性阻塞性肺病。
• [EN] PYRROLIDINE AND BICYCLOHETEROARYL CONTAINING OGA INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS D'OGA CONTENANT DE LA PYRROLIDINE ET DE LA BICYCLOHÉTÉROARYLE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021094312A1

  公开（公告）日：2021-05-20

  The present invention relates to O-GIcNAc hydrolase (OGA) inhibitors. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which inhibition of OGA is beneficial, such as tauopathies, in particular Alzheimer's disease or progressive supranuclear palsy; and neurodegenerative diseases accompanied by a tau pathology, in particular amyotrophic lateral sclerosis or frontotemporal lobe dementia caused by C90RF72 mutations; or alpha synucleinopathies, in particular Parkinson's disease, dementia due to Parkinson's (or neurocognitive disorder due to Parkinson's disease), dementia with Lewy bodies, multiple system atrophy, or alpha synucleinopathy caused by Gaucher's disease.

  本发明涉及O-GIcNAc水解酶（OGA）抑制剂。该发明还涉及包含这类化合物的药物组合物，制备这类化合物和组合物的方法，以及利用这类化合物和组合物预防和治疗抑制OGA有益的疾病，如tau病变，特别是阿尔茨海默病或进行性上行性麻痹；以及伴有tau病理的神经退行性疾病，特别是由C90RF72突变引起的肌萎缩侧索硬化或额颞叶痴呆；或α-突触核蛋白病，特别是帕金森病，由帕金森病引起的痴呆（或由帕金森病引起的神经认知障碍），具有Lewy小体的痴呆，多系统萎缩，或由高雪氏病引起的α-突触核蛋白病。
• [EN] AMIDE DERIVATIVES USEFUL IN THE TREATMENT OF HBV INFECTION OR HBV-INDUCED DISEASES<br/>[FR] DÉRIVÉS D'AMIDE UTILES DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B OU DE MALADIES INDUITES PAR LE VIRUS DE L'HÉPATITE B
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2020225230A1

  公开（公告）日：2020-11-12

  The application relates to amide derivatives, processes for their preparation, pharmaceutical compositions, and their uses, more particularly their uses in treating chronic hepatitis B virus (HBV) infection.

  该申请涉及酰胺衍生物，其制备方法，药物组合物以及它们的用途，更具体地说，它们在治疗慢性乙型肝炎病毒（HBV）感染中的用途。
• NOVEL CATHEPSIN C INHIBITORS AND THEIR USE
  申请人：Palovich Michael R.

  公开号：US20090264431A1

  公开（公告）日：2009-10-22

  The invention is directed to compounds according to Formula I: wherein R1, R2a, R2b, R2c, R3, and n are defined below, and to pharmaceutically-acceptable salts thereof. They are cathepsin C inhibitors and can be used in the treatment of diseases mediated by the cathepsin C enzyme, such as COPD.

  本发明涉及符合以下式子I的化合物：其中R1、R2a、R2b、R2c、R3和n的定义如下，以及其药学上可接受的盐。它们是卡特普西林C抑制剂，可用于治疗由卡特普西林C酶介导的疾病，如COPD。
• WO2020163193A5
  申请人：——

  公开号：WO2020163193A5

  公开（公告）日：2023-02-09