(S)-(-)-4-fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide | 223644-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (S)-(-)-4-fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide
• 英文别名: (S)-4-Fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide；4-fluoro-N-[(2S)-1-hydroxypropan-2-yl]isoquinoline-5-sulfonamide
• CAS: 223644-12-0
• 化学式: C₁₂H₁₃FN₂O₃S
• 分子量: 284.311
• InChiKey: UFMZFWOWTOGZIK-QMMMGPOBSA-N

物化性质

• 熔点：
  149-151 °C
• 沸点：
  486.3±55.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(-)-4-fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.5h， 生成 (S)-4-fluoro-N-(1-((3-hydroxypropyl)amino)propan-2-yl)-isoquinoline-5-sulfonamide oxalate
  参考文献：
  名称：

  Identification of Nitric Oxide-Donating Ripasudil Derivatives with Intraocular Pressure Lowering and Retinal Ganglion Cell Protection Activities

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c00600
• 作为产物：
  描述：

  4-氟异喹啉 在 氯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-(-)-4-fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide
  参考文献：
  名称：

  A Practical Synthesis of Novel Rho-Kinase Inhibitor, (S)-4-Fluoro-5-(2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline

  摘要：

  A practical synthesis of novel Rho-kinase inhibitor, (S)-4-fluoro-5-(2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline hydrochloride dihydrate (1) was achieved in a pilot-scale production. We have demonstrated the regioselective chlorosulfonylation of 4-fluoroisoquinoline in an one-pot reaction to afford 4-fluoroisoquinoline-5-sulfonyl chloride and the asymmetric construction of the (S)-2-methyl-1,4-diazepane moiety as key steps.

  DOI：

  10.3987/com-11-12230

文献信息

• NOVEL PRODUCTION METHOD FOR ISOQUINOLINE DERIVATIVES AND SALTS THEREOF
  申请人：Gomi Noriaki

  公开号：US20130144054A1

  公开（公告）日：2013-06-06

  The present invention provides a method capable of industrially producing a target product, i.e., a compound represented by the aforementioned formula (I) or a salt thereof, which is useful for preventing and treating cerebrovascular disorders such as cerebral infarction, cerebral hemorrhage, subarachnoid hemorrhage, and cerebral edema, particularly for preventing and treating glaucoma, at high yield even on a large scale without imposing a negative impact on the environment. The present invention provides a method for producing a compound represented by formula (I) or a salt thereof, wherein the method comprises a step of reacting a compound represented by formula (III) or a salt thereof with a compound represented by formula (II) in the presence of at least one solvent selected from the group consisting of a nitrile solvent, an amide solvent, a sulfoxide solvent, and a urea solvent, and a base.

  本发明提供了一种能够在工业上生产目标产品的方法，即一种由上述公式（I）表示的化合物或其盐，该化合物对预防和治疗脑血管疾病（如脑梗死、脑出血、蛛网膜下腔出血和脑水肿）特别是对预防和治疗青光眼具有用处，即使在大规模生产时也能高产率地生产，而且不对环境造成负面影响。本发明提供了一种生产由公式（I）表示的化合物或其盐的方法，其中该方法包括以下步骤：在至少选择自腈溶剂、酰胺溶剂、亚砜溶剂和脲溶剂组成的群中选择至少一种溶剂和一种碱的条件下，将由公式（III）表示的化合物或其盐与由公式（II）表示的化合物反应。
• [EN] ISOQUINOLINE DERIVATIVE AND DRUG<br/>[FR] DERIVE D'ISOQUINOLEINE ET MEDICAMENT
  申请人：HIDAKA, Hiroyoshi

  公开号：WO1999020620A1

  公开（公告）日：1999-04-29

  (EN) The isoquinoline derivative represented by formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing either of them as the active ingredient. The compound (I) is useful as a preventive or remedy for cerebrovascular accident and is particularly excellent as a depressor for cerebrovascular contraction. It is also useful as a preventive or remedy for diseases accompanied by ischemic lesion.(FR) L'invention concerne le dérivé d'isoquinoléine qui correspond à la formule (I), ses sels pharmaceutiquement acceptables et des compositions pharmaceutiques contenant un de ces sels en tant que composant actif. Le composé (I) peut servir à la prévention ou au traitement d'accidents cérébrovasculaires et se présente comme un dépresseur particulièrement efficace en cas de contractions cérébrovasculaires. Il peut également servir à la prévention ou au traitement des maladies accompagnées de lésions ischémiques.

  (I)式所表示的异喹啉衍生物及其药学上可接受的盐，以及含有它们中的任何一种作为活性成分的制药组合物。该化合物(I)可用于预防或治疗脑血管意外，并且在脑血管收缩方面特别出色。它还可用于预防或治疗伴随缺血性损伤的疾病。
• (S)-(-)-1-(4-fluoroisoquinolin-5-Yl)Sulfonyl-2-methyl-1,4-homopiperazine hydrochloride dihydrate
  申请人：Kowa Co., Ltd.

  公开号：US07858615B2

  公开（公告）日：2010-12-28

  The present invention is directed to (S)-(−)-1-(4-fluoroisoquinolin-5-yl)sulfonyl-2-methyl-1,4-homopiperazine hydrochloride dihydrate, to a method producing the dihydrate, and to a drug composition containing the dihydrate. The compound of the present invention has less hygroscopicity as compared with (S)-(−)-1-(4-fluoroisoquinolin-5-yl)sulfonyl-2-methyl-1,4-homopiperazine hydrochloride anhydrous crystals and thus, exhibits excellent chemical stability.

  本发明涉及(S)-(−)-1-(4-氟异喹啉-5-基)磺酰基-2-甲基-1,4-同型哌嗪盐酸盐二水合物，一种制备该二水合物的方法以及包含该二水合物的药物组合物。本发明化合物与(S)-(−)-1-(4-氟异喹啉-5-基)磺酰基-2-甲基-1,4-同型哌嗪盐酸盐无水晶相比具有较小的吸湿性，因此表现出优异的化学稳定性。
• (S)-(-)-1-(4-FLUOROISOQUINOLIN-5-YL)SULFONYL-2METHYL-1,4HOMOPIPERAZINE HYDROCHLORIDE DIHYDRATE
  申请人：Kowa Company, Ltd.

  公开号：EP1818329A1

  公开（公告）日：2007-08-15

  The present invention is directed to (S)-(-)-1-(4-fluoroisoquinolin-5-yl)sulfonyl-2-methyl-1,4-homopiperazine hydrochloride dihydrate, to a method producing the dihydrate, and to a drug composition containing the dihydrate. The compound of the present invention has less hygroscopicity as compared with (S)-(-)-1-(4-fluoroisoquinolin-5-yl)sulfonyl-2-methyl-1,4-homopiperazine hydrochloride anhydrous crystals and thus, exhibits excellent chemical stability.

  本发明涉及(S)-(-)-1-(4-氟异喹啉-5-基)磺酰基-2-甲基-1,4-高哌嗪盐酸盐二水合物、生产该二水合物的方法以及含有该二水合物的药物组合物。与(S)-(-)-1-(4-氟异喹啉-5-基)磺酰基-2-甲基-1,4-高哌嗪盐酸盐无水结晶相比，本发明化合物的吸湿性较小，因此具有极佳的化学稳定性。
• WO2006/57397
  申请人：——

  公开号：——

  公开（公告）日：——