4-(2-isopropoxy-3,4-dioxo-cyclobut-1-enyl)-2,2-dimethyl-2H-chromene-6-carbonitrile | 175339-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(2-isopropoxy-3,4-dioxo-cyclobut-1-enyl)-2,2-dimethyl-2H-chromene-6-carbonitrile
• 英文别名: 4-(3,4-dioxo-2-propan-2-yloxycyclobuten-1-yl)-2,2-dimethylchromene-6-carbonitrile
• CAS: 175339-66-9
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: WVZKITHHVPUCHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-isopropoxy-3,4-dioxo-cyclobut-1-enyl)-2,2-dimethyl-2H-chromene-6-carbonitrile 以 乙腈 为溶剂， 生成 4-(2-amino-3,4-dioxo-cyclobut-1-enyl)-2,2-dimethyl-2H-chromene-6-carbonitrile
  参考文献：
  名称：

  (3,4-dioxocyclobuten-1-yl)chromene, indene, and dihydronaphthalenone

  摘要：

  本发明涉及新型的4-(3,4-二氧杂环丁烯-1-基)香豆素和二氢萘酮以及3-(3,4-二氧杂环丁烯-1-基)吲哚及其盐，具有平滑肌松弛活性，用于治疗高血压、外周血管疾病、充血性心力衰竭、涉及尿道过度平滑肌收缩的疾病，如失禁或涉及胃肠道过度平滑肌收缩的疾病，如肠易激综合征、哮喘和脱发以及含有本发明化合物的制药组合物。本发明揭示了由公式(I)表示的化合物：其中：R1和R2，独立于彼此，选择自以下：C1-6全氟烷氧基，C1-6全氟烷基，C1-6烷基，C1-6烷氧基，羟基，C1-6烷氧羰基，硝基，氰基，卤素，C1-6烷基磺酰胺基，C1-6全氟烷基磺酰胺基，氨基，C1-6酰胺基，C1-6全氟酰胺基，单个或双个C1-12烷基氨基，C1-6烷基磺酰基，C6-10芳基磺酰基，羧基，C1-12单个或双个烷基氨基甲酰基，或氢；a和b一起形成--O--连接，C.dbd.O，或直接键；R3和R4，独立于彼此，是H或C1-6烷基，可选择地被氟取代；R5是氨基或C1-12单个烷基胺基；R6是H，C1-6全氟烷基，C1-6烷基，C6-10芳基或含有1-3个异原子（选自N、O或S）的单个或双环杂环。

  公开号：

  US05482942A1

文献信息

• (3,4-DIOXOCYCLOBUTEN-1-YL)CHROMENE, INDENE, AND DIHYDRONAPHTHALENONE DERIVATIVES AS SMOOTH MUSCLE RELAXANTS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0767787A1

  公开（公告）日：1997-04-16
• US5482942A
  申请人：——

  公开号：US5482942A

  公开（公告）日：1996-01-09
• [EN] (3,4-DIOXOCYCLOBUTEN-1-YL)CHROMENE, INDENE, AND DIHYDRONAPHTHALENONE DERIVATIVES AS SMOOTH MUSCLE RELAXANTS<br/>[FR] DERIVES DE (3,4-DIOXOCYCLOBUTENE-1-YL) CHROMENE, INDENE ET DIHYDRONAPHTHALENONE EN TANT QU'AGENTS RELAXANTS DES MUSCLES LISSES
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：WO1996000725A1

  公开（公告）日：1996-01-11

  (EN) This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by formula (I), wherein R1 and R2, independent from each other, are selected from the following: C1-6 perfluoroalkoxy, C1-6 perfluoroalkyl, C1-6 alkyl, C1-6 alkoxy, hydroxyl, C1-6 alkoxycarbonyl, nitro, cyano, halogen, C1-6 alkylsulfonamido, C1-6 perfluoroalkylsulfonamido, amino, C1-6 acylamino, C1-6 perfluoroacylamino, mono or di-C 1-12 alkylamino, C1-6 alkylsulfonyl, C6-10 arylsulfonyl, carboxyl, C1-12 mono or di-alkylaminocarbonyl, or hydrogen; a and b together form an -O- linkage, C=O, or a direct bond; R3 and R4, independent from each other, are H or C1-6 alkyl, optionally substituted by fluorine; R5 is amino or C1-12 mono alkylamine; R6 is H, C1-6 perfluoroalkyl, C1-6 alkyl, C6-10 aryl, or mono or bicyclic heteroaryl containing 1-3 heteroatoms selected from N, O, or S.(FR) L'invention concerne de nouveaux 4-(3,4-dioxocyclobutène-1-yl)chromènes et dihydronaphthalénones et 3-(3,4-dioxocyclobutène-1-yl)indènes, ainsi que leurs sels, présentant une efficacité de relâchement des muscles lisses, leur utilisation dans le traitement de l'hypertension, ainsi que dans le traitement de maladies vascularres périphériques, de la défaillance cardiaque ÷démateuse, de maladies impliquant une contraction excessive des muscles lisses des voies urinaires, telles que l'incontinence, ou des voies gastrointestinales, telles que la colopathie fonctionnelle, de l'asthme et de la perte des cheveux, ainsi que des compositions pharmaceutiques contenant les composés représentés par la formule (I) dans laquelle: R1 et R2, indépendant l'un de l'autre, sont sélectionnés à partir de: perfluoroalcoxy C1-6, perfluoroalkyle C1-6, alkyle C1-6, alcoxy C1-6, hydroxyle, alcoxycarbonyle C1-6,nitro, cyano, halogène, alkylsulfonamido C1-6, perfluoroalkylsulfonamido C1-6, amino, acylamino C1-6 perfluoroacylamino C1-6, mono ou di-alkylamino C1-12, alkylsulfonyle C1-6, arylsulfonyle C6-10, carboxyle, mono ou di-alkylaminocarbonyle C1-12 ou hydrogène; a et b constituent ensemble une liaison -O-, C=O ou une liaison directe; R3 et R4, indépendant l'un de l'autre, représentent H ou alkyle C1-6, éventuellement substitué par fluor; R5 représente amino ou mono alkylamine C1-12; R6 représente H, perfluoroalkyle C1-6, aryle C6-10 ou hétéroaryle mono ou bicyclique contenant 1-3 hétéroatomes sélectionnés à partir de N, O ou S.
• (3,4-dioxocyclobuten-1-yl)chromene, indene, and dihydronaphthalenone
  申请人：American Home Products Corporation

  公开号：US05482942A1

  公开（公告）日：1996-01-09

  This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.1-6 perfluoroacylamino, mono or di-C.sub.1-12 alkylamino, C.sub.1-6 alkylsulfonyl, C.sub.6-10 arylsulfonyl, carboxyl, C.sub.1-12 mono or di-alkylaminocarbonyl, or hydrogen; a and b together form an --O-- linkage, C.dbd.O, or a direct bond: R.sub.3 and R.sub.4, independent from each other, are H or C.sub.1-6 alkyl, optionally substituted by fluorine; R.sub.5 is amino or C.sub.1-12 mono alkylamine; R.sub.6 is H, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.6-10 aryl, or mono or bicyclic heteroaryl containing 1-3 heteroatoms selected from N, O, or S.

  本发明涉及一种新型的4-(3,4-二氧代环丁烷-1-基)香豆素和二氢萘酮以及3-(3,4-二氧代环丁烷-1-基)茚和其盐，具有平滑肌松弛活性，用于治疗高血压以及外周血管疾病、充血性心力衰竭、涉及泌尿道过度平滑肌收缩的疾病（如失禁）或涉及胃肠道过度平滑肌收缩的疾病（如肠易激综合征）、哮喘、脱发以及含有本发明化合物的药物组合物。本发明公开了由式(I)表示的化合物：##STR1## 其中：R1和R2彼此独立地从以下选定：C1-6全氟烷氧基、C1-6全氟烷基、C1-6烷基、C1-6烷氧基、羟基、C1-6烷氧羰基、硝基、氰基、卤素、C1-6烷基磺酰胺基、C1-6全氟烷基磺酰胺基、氨基、C1-6酰胺基、C1-6全氟酰胺基、单个或双个C1-12烷基氨基、C1-6烷基磺酰基、C6-10芳基磺酰基、羧基、C1-12单个或双个烷基氨基羰基或氢；a和b共同形成--O--连接、C.dbd.O或直接键；R3和R4彼此独立地为H或C1-6烷基，可选地取代为氟；R5为氨基或C1-12单个烷基胺基；R6为H、C1-6全氟烷基、C1-6烷基、C6-10芳基或含有1-3个杂原子（选自N、O或S）的单个或双环杂芳基。