2-methylbenzothiophene-5-carboxylic acid | 86792-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-methylbenzothiophene-5-carboxylic acid
• 英文别名: 2-methylbenzo[b]thiophene-5-carboxylic acid；2-methyl-1-benzothiophene-5-carboxylic acid
• CAS: 86792-71-4
• 化学式: C₁₀H₈O₂S
• 分子量: 192.238
• InChiKey: APSXOACQRGXISO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylbenzothiophene-5-carboxylic acid 以 甲醇 为溶剂， 生成 2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Benzo-fused thromboxane synthetase inhibitors

  摘要：

  一系列新型的羧基取代萘衍生物和羧基取代的苯并杂环化合物已被制备，包括吲哚、苯并呋喃和苯并噻吩的羧基取代衍生物，以及它们的药用可接受盐。这些特定化合物在治疗血栓形成、缺血性心脏病、中风、短暂性脑缺血发作、偏头痛、外周血管疾病、糖尿病的血管并发症和内毒素性休克方面具有用途。优选的成员化合物包括2-(1-咪唑基甲基)-3-甲基苯并[b]噻吩-5-羧酸和3-甲基-2-(3-吡啶甲基)苯并[b]噻吩-5-羧酸。提供了从已知起始材料制备这些化合物的方法。

  公开号：

  US04496572A1
• 作为产物：
  描述：

  5-bromo-2-methylbenzothiophene 在 二氧化碳 作用下， 生成 2-methylbenzothiophene-5-carboxylic acid
  参考文献：
  名称：

  Benzo-fused thromboxane synthetase inhibitors

  摘要：

  一系列新型的羧基取代萘衍生物和羧基取代的苯并杂环化合物已被制备，包括吲哚、苯并呋喃和苯并噻吩的羧基取代衍生物，以及它们的药用可接受盐。这些特定化合物在治疗血栓形成、缺血性心脏病、中风、短暂性脑缺血发作、偏头痛、外周血管疾病、糖尿病的血管并发症和内毒素性休克方面具有用途。优选的成员化合物包括2-(1-咪唑基甲基)-3-甲基苯并[b]噻吩-5-羧酸和3-甲基-2-(3-吡啶甲基)苯并[b]噻吩-5-羧酸。提供了从已知起始材料制备这些化合物的方法。

  公开号：

  US04496572A1

文献信息

• JAK INHIBITOR
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP2108642A1

  公开（公告）日：2009-10-14

  A JAK inhibitor comprising, as an active ingredient, a nitrogen-containing heterocyclic compound represented by formula (I) wherein W represents a nitrogen atom or -CH-; X represents -C (=O) - or -CHR4- (wherein R4 represents a hydrogen atom, or the like); R1 represents the formula described below [wherein Q1 represents-CR8-(wherein R8 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like); Q2 represents -NR15- (wherein R15 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like); and R5 and R6 may be the same or different and each represents a hydrogen atom, halogen, carboxy, substituted or unsubstituted lower alkyl, or the like], or the like; and R2 and R3 may be the same or different and each represents a hydrogen atom, halogen, substituted or unsubstituted lower alkyl, or the like} or a pharmaceutically acceptable salt thereof.

  一种JAK抑制剂，其作为活性成分的是由式(I)表示的含氮杂环化合物 其中W代表氮原子或-CH-; X代表-C(=O)-或-CHR4-(其中R4代表氢原子或类似物); R1代表下述式[其中Q1代表-CR8-(其中R8代表氢原子、取代或未取代的较低烷基或类似物); Q2代表-NR15-(其中R15代表氢原子、取代或未取代的较低烷基或类似物);而R5和R6可以相同也可以不同，每个代表氢原子、卤素、羧基、取代或未取代的较低烷基或类似物，或类似物;而 R2和R3可以相同也可以不同，每个代表氢原子、卤素、取代或未取代的较低烷基或类似物}或其药学上可接受的盐。
• Sulfonamide compounds and medicinal use thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06348474B1

  公开（公告）日：2002-02-19

  A sulfonamide compound of the formula (I): R1—SO2NHCO—A—R2  (I) wherein R1 is alkyl, alkenyl, alkynyl and the like; A is an optionally substituted heteropolycyclic group except benzimidazolyl, indolyl, 4,7-dihydrobenzimidazolyl and 2,3-dihydrobenzoxazinyl; X is alkylene, oxa, oxa(lower)alkylene and the like; and R2 is optionally substituted aryl, substituted biphenylyl and the like, a salt thereof and a pharmaceutical composition comprising the same. The sulfonamide compound is effective for the diseases treatable based on their blood sugar level-depressing activity, cGMP-PDE (especially PDE-V)-inhibiting activity, smooth muscle relaxing activity, bronchodilating activity, vasodilating activity, smooth muscle cell suppressing activity, and antiallergic activity.

  化合物的化学式（I）为磺胺类化合物： R1—SO2NHCO—A—R2  （I） 其中R1为烷基，烯基，炔基等；A为除苯并咪唑基，吲哚基，4,7-二氢苯并咪唑基和2,3-二氢苯并噁嗪基之外的可选择取代的杂多环基团；X为烷基，氧杂环烷基等；R2为可选择取代的芳基，取代的联苯基等，其盐及包含其的药物组合物。该磺胺类化合物对于基于其降低血糖水平活性、cGMP-PDE（特别是PDE-V）抑制活性、平滑肌松弛活性、支气管扩张活性、血管扩张活性、平滑肌细胞抑制活性和抗过敏活性可治疗的疾病有效。
• Selective thromboxane synthetase inhibitors. 4. 2-(1H-Imidazol-1-ylmethyl)benzo[b]furan-, -benzo[b]thiophene-, -indole- and -naphthalenecarboxylic acids
  作者：Peter E. Cross、Roger P. Dickinson、M. John Parry、Michael J. Randall

  DOI：10.1021/jm00159a013

  日期：1986.9

  The preparation of a series of 2-(1H-imidazol-1-ylmethyl)-substituted carboxylic acids of benzo[b]furan, benzo-[b]thiophene, indole, and naphthalene is described. All compounds showed a similar level of activity as TxA2 synthetase inhibitors in vitro, having IC50 values between 1 and 7 X 10(-8) M. In the cases examined, compounds had, at most, only negligible activity against PGI2 synthetase, cyclooxygenase

  描述了苯并[b]呋喃，苯并-[b]噻吩，吲哚和萘的一系列2-（1H-咪唑-1-基甲基）取代的羧酸的制备。在体外，所有化合物均显示出与TxA2合成酶抑制剂相似的活性水平，IC50值为1至7 X 10（-8）M。在所检查的情况下，化合物对PGI2合成酶，环加氧酶的活性至多仅微不足道。和类固醇11β-羟化酶。苯并[b]噻吩通常在体内表现出最大的效力，在向有意识的狗口服施用0.5 mg / kg后的6小时内，化合物72、73和75几乎完全抑制了血栓烷的产生。在73和75的情况下，24小时后血栓烷的产生仍被抑制了80％。
• [EN] ARYLCARBOXAMIDES AND USES THEREOF<br/>[FR] ARYLCARBOXAMIDES ET LEURS UTILISATIONS
  申请人：INCEPTION 1 INC

  公开号：WO2017192304A1

  公开（公告）日：2017-11-09

  The present disclosure is directed to compounds of formula (I): or a pharmaceutically acceptable salt, solvate or solvate of the salt thereof. Compounds of formula (I) are inhibitors of NOX4 and are useful in the treatment of fibrotic diseases such as scleroderma; lung disease, such as pulmonary fibrosis including idiopathic pulmonary fibrosis (IPF); heart disease, such as heart failure due to ischaemic heart disease, valvular heart disease and hypertensive heart disease, diabetic cardiomyopathy and hypertension; liver disease, such as cirrhosis of the liver; and kidney disease, such as progressive kidney disease glomerulonephritis and diabetic nephropathy; and eye disease such as diabetic retinopathy; skin or subcutaneous scarring, such as keloids, adhesions, hypertrophic scarring or cosmetic scarring; or as an adjuvant or anti-fibrotic in pancreatic cancer to increase chemotherapeutic drug penetration by reducing the density of the connective tissue stroma.

  本公开涉及的化合物具有以下结构式（I）：或其药学上可接受的盐、溶剂或该盐的溶剂。结构式（I）的化合物是NOX4的抑制剂，可用于治疗纤维化疾病，如硬皮病；肺部疾病，如肺纤维化，包括特发性肺纤维化（IPF）；心脏疾病，如缺血性心脏病、瓣膜性心脏病和高血压性心脏病、糖尿病性心肌病和高血压；肝脏疾病，如肝硬化；肾脏疾病，如进行性肾脏疾病肾小球肾炎和糖尿病肾病；眼部疾病，如糖尿病视网膜病变；皮肤或皮下疤痕，如瘢痕、粘连、肥厚性瘢痕或美容瘢痕；或作为胰腺癌的辅助治疗或抗纤维化剂，通过减少结缔组织基质密度来增加化疗药物的渗透性。
• Sulfonamide compounds and pharmaceutical use thereof
  申请人：Fujisawa Pharmaceutical Co. Ltd.

  公开号：US20020099212A1

  公开（公告）日：2002-07-25

  A sulfonamide compound of the formula (I): R 1 —SO 2 NHCO—A—X—R 2 (I) wherein R 1 is alky, alkenyl, alkynyl and the like; A is an optionally substituted heteropolycyclic group except benzimidazolyl, indolyl, 4,7-dihydrobenzimidazolyl and 2,3-dihydrobenzoxazinyl; X is alkylene, oxa, oxa(lower)alkylene and the like; and R 2 is optionally substituted aryl, substituted biphenylyl and the like, a salt thereof and a pharmaceutical composition comprising the same. The sulfonamide compound is effective for the diseases treatable based on their blood sugar level-depressing activity, cGMP-PDE (especially PDE-V)-inhibiting activity, smooth muscle relaxing activity, bronchodilating activity, vasodilating activity, smooth muscle cell suppressing activity, and antiallergic activity.

  化合物I的磺酰胺类化合物：R1-SO2NHCO-A-X-R2（I），其中R1是烷基，烯基，炔基等；A是可选取代的异杂多环基团，但不包括苯并咪唑基，吲哚基，4,7-二氢苯并咪唑基和2,3-二氢苯并噁唑基；X是烷基，氧杂环烷基，氧杂环（低）烷基等；R2是可选取代的芳基，取代联苯基等，其盐和药物组成物。该磺酰胺类化合物对于可基于其降低血糖水平的活性、cGMP-PDE（特别是PDE-V）抑制活性、平滑肌松弛活性、支气管扩张活性、血管扩张活性、平滑肌细胞抑制活性和抗过敏活性可治疗的疾病有效。