5-(4-benzyloxyphenyl)thiophene-2-carboxylic acid methyl ester | 742058-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(4-benzyloxyphenyl)thiophene-2-carboxylic acid methyl ester
• 英文别名: methyl 5-(4-phenylmethoxyphenyl)thiophene-2-carboxylate
• CAS: 742058-33-9
• 化学式: C₁₉H₁₆O₃S
• 分子量: 324.4
• InChiKey: HMIGTUDRDDMLLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-benzyloxyphenyl)thiophene-2-carboxylic acid methyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以74%的产率得到5-(4-benzyloxyphenyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  [EN] BIS(HETERO)ARYL CARBOXAMIDE DERIVATIVES FOR USE AS PGI2 ANTAGONISTS
  [FR] DERIVES DE BIS(HETERO)ARYLE CARBOXAMIDE DESTINES A ETRE UTILISES EN TANT QU'ANTAGONISTES DE LA PG12

  摘要：

  本发明涉及式(I)的芳基或杂环芳基酰胺烷基衍生物，其中R6代表羧基或四唑基，其作为药物制剂的活性成分是有用的。本发明的芳基或杂环芳基酰胺烷基具有PGI2拮抗活性，可用于预防和治疗与PGI2活性相关的疾病。这些疾病包括泌尿系统疾病或障碍，如：膀胱出口梗阻、膀胱过度活跃、尿失禁、膀胱逼尿肌过度反射、膀胱逼尿肌不稳定、膀胱容量减少、排尿频率增加、急迫性尿失禁、压力性尿失禁、膀胱高反应性、良性前列腺增生（BPH）、前列腺炎、尿频、夜尿、尿急、盆腔过敏、尿道炎、盆腔疼痛综合征、前列腺疼痛综合征、膀胱炎或特发性膀胱过敏。本发明的化合物还可用于治疗疼痛，包括但不限于炎症性疼痛、神经病性疼痛、急性疼痛、慢性疼痛、牙痛、经前疼痛、内脏疼痛、头痛等；低血压；血友病和出血；以及炎症，因为这些疾病也与PGI2有关。

  公开号：

  WO2004069805A1
• 作为产物：
  描述：

  5-溴噻吩-2-甲酸甲酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-(4-benzyloxyphenyl)thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  De Novo Design of Nurr1 Agonists via Fragment-Augmented Generative Deep Learning in Low-Data Regime

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00485

文献信息

• [EN] BIS(HETERO)ARYL CARBOXAMIDE DERIVATIVES FOR USE AS PGI2 ANTAGONISTS<br/>[FR] DERIVES DE BIS(HETERO)ARYLE CARBOXAMIDE DESTINES A ETRE UTILISES EN TANT QU'ANTAGONISTES DE LA PG12
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004069805A1

  公开（公告）日：2004-08-19

  The present invention relates to aryl or heteroaryl amido alkane derivatives of formula (I) wherein R6 represents carboxy or tetrazolyl, which are useful as an active ingredient of pharmaceutical preparations. The aryl or heteroaryl amido alkanes of the present invention have PGI2 antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with PGI2 activity.Such diseases include urological diseases or disorder as follows: bladder outlet obstruction, overactive bladder, urinary incontinence, detrusor hyper-reflexia, detrusor instability, reduced bladder capacity, frequency of micturition, urge incontinence, stress incontinence, bladder hyperreactivity, benighn prostatic hypertrophy (BPH), prostatitis, urinary frequency, nocturia, urinary urgency, pelvic hypersensitivity, urethritis, pelvic pain syndrome, prostatodynia, cystitis, or idiophatic bladder hypersensitivity.The compounds of the present invention are also useful for treatment of pain including, but not limited to inflammatory pain, neuropathic pain, acute pain, chronic pain, dental pain, premenstrual pain, visceral pain, headaches, and the like; hypotension;hemophilia and hemorrhage; and inflammation, since the diseases also relate to PGI2.

  本发明涉及式(I)的芳基或杂环芳基酰胺烷基衍生物，其中R6代表羧基或四唑基，其作为药物制剂的活性成分是有用的。本发明的芳基或杂环芳基酰胺烷基具有PGI2拮抗活性，可用于预防和治疗与PGI2活性相关的疾病。这些疾病包括泌尿系统疾病或障碍，如：膀胱出口梗阻、膀胱过度活跃、尿失禁、膀胱逼尿肌过度反射、膀胱逼尿肌不稳定、膀胱容量减少、排尿频率增加、急迫性尿失禁、压力性尿失禁、膀胱高反应性、良性前列腺增生（BPH）、前列腺炎、尿频、夜尿、尿急、盆腔过敏、尿道炎、盆腔疼痛综合征、前列腺疼痛综合征、膀胱炎或特发性膀胱过敏。本发明的化合物还可用于治疗疼痛，包括但不限于炎症性疼痛、神经病性疼痛、急性疼痛、慢性疼痛、牙痛、经前疼痛、内脏疼痛、头痛等；低血压；血友病和出血；以及炎症，因为这些疾病也与PGI2有关。
• Bis (hetero) aryl carboxamide derivatives for use as PG12 antagonists
  申请人：Murata Toshiki

  公开号：US20060247260A1

  公开（公告）日：2006-11-02

  This invention relates to aryl or heteroaryl amido alkane derivatives of formula (I) in which Ar 1 and Ar 2 independently represent phenyl or a 5 or 6-membered heteroaromatic ring, R 6 represents carboxyl or tetrazolyl, and the remaining variables are as defined in the text and claims, which are useful as an active ingredient of pharmaceutical preparations. The aryl or heteroaryl amido alkanes of the present invention have PGI2 antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with PGI2 activity. Such diseases include urological diseases or disorder as follows: bladder outlet obstruction, overactive bladder, urinary incontinence, detrusor hyper-reflexia, detrusor instability, reduced bladder capacity, frequency of micturition, urge incontinence, stress incontinence, bladder hyperreactivity, benighn prostatic hypertrophy (BPH), prostatitis, urinary frequency, nocturia, urinary urgency, pelvic hypersensitivity, urethritis, pelvic pain syndrome, prostatodynia, cystitis, or idiophatic bladder hypersensitivity. The compounds of the present invention are also useful for treatment of pain including, but not limited to inflammatory pain, neuropathic pain, acute pain, chronic pain, dental pain, premenstrual pain, visceral pain, headaches, and the like; hypotension;hemophilia and hemorrhage; and inflammation, since the diseases also relate to PGI2.

  本发明涉及公式（I）中的芳基或杂环芳基酰胺烷衍生物，其中Ar1和Ar2分别表示苯基或5或6成员杂环芳基环，R6表示羧基或四唑基，其余变量如文本和权利要求所定义，可用作药物制剂的活性成分。本发明的芳基或杂环芳基酰胺烷具有PGI2拮抗活性，可用于预防和治疗与PGI2活性相关的疾病。这些疾病包括以下泌尿系统疾病或障碍：膀胱出口梗阻，过度活动的膀胱，尿失禁，膀胱平滑肌反射亢进，膀胱平滑肌不稳定，膀胱容量减少，排尿频率，急迫性尿失禁，压力性尿失禁，膀胱高反应性，良性前列腺增生（BPH），前列腺炎，尿频，夜尿，尿急，盆腔过敏，尿道炎，盆腔疼痛综合征，前列腺疼痛，膀胱炎或特发性膀胱过敏。本发明化合物还可用于治疗疼痛，包括但不限于炎症性疼痛，神经病理性疼痛，急性疼痛，慢性疼痛，牙痛，经前痛，内脏疼痛，头痛等；低血压；血友病和出血；以及炎症，因为这些疾病也与PGI2有关。
• AGENT FOR TREATING OR PREVENTING DIGESTIVE ULCER
  申请人：Kawakami Masakatsu

  公开号：US20090036428A1

  公开（公告）日：2009-02-05

  An object of the present invention is to provide an agent for treating or preventing digestive ulcer that is effective even to ulcer of small intestine and others, for which gastric acid secretion inhibitors such as proton pump inhibitors are ineffective, and is superior to allopurinol in the efficaciousness and the safety. The pharmaceutical composition of the present invention comprising a non-purine xanthine oxidase inhibitor as the active ingredient is useful as an agent for treating or preventing ulcer that forms in digestive tracts by the attack of gastric acid, pepsin, stress, Helicobacter pylori bacteria, NSAID, etc. In particular, it is useful as an ulcer remedy heretofore unknown in the art as it is effective even for ulcer in small intestine for which gastric/duodenal ulcer remedies that inhibit gastric acid secretion such as proton pump inhibitors are ineffective.

  本发明的目的是提供一种治疗或预防消化性溃疡的药剂，即使是质子泵抑制剂对小肠溃疡等无效的溃疡也能有效治疗或预防，并且在功效和安全性方面优于丙戊酸和乙酰水杨酸等药物。本发明的药物组合物包括非嘌呤黄嘌呤氧化酶抑制剂作为活性成分，可用作治疗或预防由胃酸、胃蛋白酶、压力、幽门螺杆菌、NSAID等侵蚀消化道形成的溃疡的药剂。特别是，它是一种迄今为止在技术上未知的溃疡治疗方法，因为它即使对于质子泵抑制剂等抑制胃酸分泌的胃/十二指肠溃疡治疗方法也非常有效，对于小肠溃疡也非常有效。
• 2-Phenylthiophene Derivative
  申请人：Miyata Junji

  公开号：US20080027048A1

  公开（公告）日：2008-01-31

  The present invention relates to a 2-phenylthiophene derivative or a salt thereof, wherein the thiophene ring is substituted with a carboxyl group or the like and the benzene ring has an electron-withdrawing group such as a cyano group and an electron-donating group such as a substituted alkoxy group at the same time. Since the compound of the invention has good xanthine oxidase-inhibitory action and uric acid-lowering action and does not have a structure derived from nucleic acid, the compound has advantages of high safety and excellent effects as compared with conventional compounds and is useful as a therapeutic or preventive agent for hyperuricemia, gout, inflammatory bowel diseases, diabetic kidney diseases, diabetic retinopathy, or the like.

  本发明涉及一种2-苯基噻吩衍生物或其盐，其中噻吩环被羧基或类似物取代，苯环同时具有电子吸引基（如氰基）和电子供给基（如取代烷氧基）。由于该化合物具有良好的黄嘌呤氧化酶抑制作用和降尿酸作用，并且不具有源自核酸的结构，因此与传统化合物相比，该化合物具有高安全性和优异的效果，并可用作治疗或预防高尿酸血症、痛风、炎症性肠病、糖尿病肾病、糖尿病视网膜病等的药物。
• 2-PHENYLTHIOPHENE DERIVATIVE
  申请人：Astellas Pharma Inc.

  公开号：EP1783124A1

  公开（公告）日：2007-05-09

  The present invention relates to a 2-phenylthiophene derivative or a salt thereof, wherein the thiophene ring is substituted with a carboxyl group or the like and the benzene ring has an electron-withdrawing group such as a cyano group and an electron-donating group such as a substituted alkoxy group at the same time. Since the compound of the invention has good xanthine oxidase-inhibitory action and uric acid-lowering action and does not have a structure derived from nucleic acid, the compound has advantages of high safety and excellent effects as compared with conventional compounds and is useful as a therapeutic or preventive agent for hyperuricemia, gout, inflammatory bowel diseases, diabetic kidney diseases, diabetic retinopathy, or the like.

  本发明涉及一种 2-苯基噻吩衍生物或其盐，其中噻吩环被羧基或类似基团取代，苯环上同时具有一个取电子基团（如氰基）和一个供电子基团（如取代的烷氧基）。 由于本发明化合物具有良好的黄嘌呤氧化酶抑制作用和降尿酸作用，且不具有来自核酸的结构，因此与传统化合物相比，本发明化合物具有安全性高、效果优异的优点，可作为高尿酸血症、痛风、炎症性肠病、糖尿病肾病、糖尿病视网膜病变或类似疾病的治疗剂或预防剂。