2-(3,4-difluorobenzyl)thiazole-4-carboxylic acid | 1202643-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3,4-difluorobenzyl)thiazole-4-carboxylic acid
• 英文别名: 2-[(3,4-Difluorophenyl)methyl]-1,3-thiazole-4-carboxylic acid
• CAS: 1202643-18-2
• 化学式: C₁₁H₇F₂NO₂S
• 分子量: 255.245
• InChiKey: YQDPGLYSLXBHSM-UHFFFAOYSA-N

物化性质

• 沸点：
  425.5±40.0 °C(predicted)
• 密度：
  1.479±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3,4-difluorobenzyl)thiazole-4-carboxylic acid 、 4-二甲氨基苄胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49%的产率得到2-(3,4-difluorobenzyl)-N-(4-(dimethylamino)benzyl)thiazole-4-carboxamide
  参考文献：
  名称：

  Discovery of a Potent, Selective T-type Calcium Channel Blocker as a Drug Candidate for the Treatment of Generalized Epilepsies

  摘要：

  We report here the discovery and pharmacological characterization of N-(1-benzyl-1H-pyrazol-3-yl)-2-phenylacetamide derivatives as potent, selective, brain-penetrating T-type calcium channel blockers. Optimization focused mainly on solubility, brain penetration, and the search for an aminopyrazole metabolite that would be negative in an Ames test. This resulted in the preparation and complete characterization of compound 66b (ACT-709478), which has been selected as a clinical candidate.

  DOI：

  10.1021/acs.jmedchem.7b01236
• 作为产物：
  描述：

  3,4-二氟苯乙酸 在 劳森试剂 、 草酰氯 、 lithium hydroxide monohydrate 、 氨 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 2-(3,4-difluorobenzyl)thiazole-4-carboxylic acid
  参考文献：
  名称：

  Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor

  摘要：

  DOI：

  10.1016/j.bmcl.2021.127846

文献信息

• FAP 저해제로서의 피롤리딘 유도체 및 이를 포함하는 약학적 조성물
  申请人：Boryung Corporation 주식회사 보령(119980015994) Corp. No ▼ 110111-0012560BRN ▼208-81-00281

  公开号：KR20200115934A

  公开（公告）日：2020-10-08

  본 발명은 FAP 저해제로서 하기 화학식 X로 나타내는, 피롤리딘 유도체 또는 그의 약학적으로 허용되는 염을 포함한다. [화학식 X]

  本发明涉及一种FAP抑制剂，包括用化学式X表示的吡啶衍生物或其药学上可接受的盐。 [化学式 X]
• NOVEL COMPOUNDS, ISOMER THEREOF, OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF AS VANILLOID RECEPTOR ANTAGONIST AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：Woo Byoung Young

  公开号：US20110152318A1

  公开（公告）日：2011-06-23

  This present invention relates to novel compounds, isomer thereof or pharmaceutically acceptable salts thereof as vanilloid receptor (Vanilloid Receptor 1; VR1; TRPV1) antagonist; and a pharmaceutical composition containing the same. The present invention provides a pharmaceutical composition for preventing or treating a disease such as pain, migraine, arthralgia, neuralgia, neuropathies, nerve injury, skin disorder, urinary bladder hypersensitiveness, irritable bowel syndrome, fecal urgency, a respiratory disorder, irritation of skin, eye or mucous membrane, stomach-duodenal ulcer, inflammatory diseases, ear disease, heart disease and so on.

  本发明涉及一种新型化合物，其异构体或其药学上可接受的盐作为vanilloid受体（Vanilloid Receptor 1; VR1; TRPV1）拮抗剂；以及包含该化合物的制药组合物。本发明提供了一种用于预防或治疗疾病的制药组合物，例如疼痛、偏头痛、关节痛、神经痛、神经病、神经损伤、皮肤疾病、膀胱过敏、肠易激综合症、排便紧迫、呼吸系统疾病、皮肤、眼或黏膜刺激、胃十二指肠溃疡、炎症性疾病、耳病、心脏病等疾病。
• [EN] NOVEL COMPOUNDS, ISOMER THEREOF, OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF AS VANILLOID RECEPTOR ANTAGONIST AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS, ISOMÈRE CORRESPONDANT OU SELS PHARMACEUTIQUEMENT ACCEPTABLES CORRESPONDANTS EN TANT QU'ANTAGONISTE DU RÉCEPTEUR VANILLOÏDE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：AMOREPACIFIC CORP

  公开号：WO2010002209A3

  公开（公告）日：2010-04-15
• SULPHONAMIDES AS VANILLOID RECEPTOR ANTAGONIST
  申请人：Amorepacific Corporation

  公开号：EP2307394B1

  公开（公告）日：2012-09-26
• Discovery of a Potent, Selective T-type Calcium Channel Blocker as a Drug Candidate for the Treatment of Generalized Epilepsies
  作者：Olivier Bezençon、Bibia Heidmann、Romain Siegrist、Simon Stamm、Sylvia Richard、Davide Pozzi、Olivier Corminboeuf、Catherine Roch、Melanie Kessler、Eric A. Ertel、Isabelle Reymond、Thomas Pfeifer、Ruben de Kanter、Michael Toeroek-Schafroth、Luca G. Moccia、Jacques Mawet、Richard Moon、Markus Rey、Bruno Capeleto、Elvire Fournier

  DOI：10.1021/acs.jmedchem.7b01236

  日期：2017.12.14

  We report here the discovery and pharmacological characterization of N-(1-benzyl-1H-pyrazol-3-yl)-2-phenylacetamide derivatives as potent, selective, brain-penetrating T-type calcium channel blockers. Optimization focused mainly on solubility, brain penetration, and the search for an aminopyrazole metabolite that would be negative in an Ames test. This resulted in the preparation and complete characterization of compound 66b (ACT-709478), which has been selected as a clinical candidate.