7-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine | 1154438-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine
• 英文别名: 7-(benzenesulfonyl)-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS: 1154438-87-5
• 化学式: C₁₆H₁₇NO₂S
• 分子量: 287.382
• InChiKey: MXLYGGPBHQMGJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 7-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  7-Sulfonamido-3-benzazepines as potent and selective 5-HT2C receptor agonists: Hit-to-lead optimization

  摘要：

  New 7-sulfonamido-3-benzazepines 3 are disclosed as 5-HT2C receptor agonists. Appropriate substitution of the amino group ((RRN)-R-1-N-2-) gave compounds that were potent 5-HT2C agonists with minimal activation of the 5-HT2A and 5-HT2B receptors. Furthermore, representative examples had excellent in vitro ADME properties and good selectivity over ion channel activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.071

文献信息

• 7-Phenylsulfonyl-tetrahydro-3-benzazepine derivatives as antipsychotic agents
  申请人：Forbes Thomson Ian

  公开号：US20050245507A1

  公开（公告）日：2005-11-03

  The invention provides compounds of formula (I): wherein A and B represent the groups —(CH 2 ) m — and —(CH 2 ) n — respectively; R 1 represents hydrogen or C 1-6 alkyl; R 2 represents hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC 1-6 alkyl, trifluoromethyl, trifluoromethoxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 fluoroalkoxy, —(CH 2 ) p C 3-6 cycloalkyl, —(CH 2 ) p OC 3-6 cycloalkyl, —COC 1-6 alkyl, —SO 2 C 1-6 alkyl, —SOC 1-6 alkyl, —S—C 1-6 alkyl, —CO 2 C 1-6 alkyl, —CO 2 NR 5 R 6 , —SO 2 NR 5 R 6 , —(CH 2 ) p NR 5 R 6 , —(CH 2 ) p NR 5 COR 6 , optionally substituted aryl ring, optionally substituted heteroaryl ring or optionally substituted heterocyclyl ring; R 3 represents hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC 1-6 alkyl, trifluoromethyl, trifluoromethoxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 fluoroalkoxy, —(CH 2 ) p C 3-6 cycloalkyl, —(CH 2 ) p OC 3-6 cycloalkyl, —COC 1-6 alkyl, —SO 2 C 1-6 alkyl, —SOC 1-6 alkyl, —S—C 1-6 alkyl, —CO 2 C 1-6 alkyl, —CO 2 NR 7 R 8 , —SO 2 NR 7 R 8 , —(CH 2 ) p NR 7 R 8 or —(CH 2 ) p NR 7 COR 8 ; R 4 represents hydrogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 fluoroalkoxy, trifluoromethyl, trifluoromethoxy, halogen, —OSO 2 CF 3 , —(CH 2 ) p C 3-6 cycloalkyl, —(CH 2 ) q OC 1-6 alkyl or —(CH 2 ) p OC 3-6 cycloalkyl; R 5 and R 6 each independently represent hydrogen, C 1-6 alkyl or, together with the nitrogen or other atoms to which they are attached, form an azacycloalkyl ring or an oxo-substituted azacycloalkyl ring; R 7 and R 8 each independently represent hydrogen or C 1-6 alkyl; m and n independently represent an integer selected from 1 and 2; p independently represents an integer selected from 0, 1, 2 and 3; q independently represents an integer selected from 1, 2 and 3; or a pharmaceutically acceptable salt or solvate thereof, with the proviso that the compounds 8-hydroxy-3-methyl-7-phenylsulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine, 8-hydroxy-7-4-(hydroxyphenyl)sulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine, 7-phenylsulfonyl-1,2,3,4-tetrahydroisoquinoline and 7-phenylsulfonyl-1,2,3,4-tetrahydroisoquinoline hydrochloride are excluded. The compounds are useful in therapy, in particular as antipsychotic agents.

  该发明提供了式（I）的化合物： 其中，A和B分别表示基团—（CH2）m—和—（ ）n—； R1表示氢或C1-6烷基； R2表示氢、卤素、羟基、氰基、硝基、羟基C1-6烷基、三氟甲基、三氟甲氧基、C1-6烷基、C1-6烷氧基、C1-6氟烷氧基、—（ ）pC3-6环烷基、—（ ）pOC3-6环烷基、—COC1-6烷基、—SO2C1-6烷基、—SOC1-6烷基、—S—C1-6烷基、—CO2C1-6烷基、—CO2NR5R6、—SO2NR5R6、—（ ）pNR5R6、—（ ）pNR5COR6、可选择的取代芳环、可选择的取代杂芳环或可选择的取代杂环基； R3表示氢、卤素、羟基、氰基、硝基、羟基C1-6烷基、三氟甲基、三氟甲氧基、C1-6烷基、C1-6烷氧基、C1-6氟烷氧基、—（ ）pC3-6环烷基、—（ ）pOC3-6环烷基、—COC1-6烷基、—SO2C1-6烷基、—SOC1-6烷基、—S—C1-6烷基、—CO2C1-6烷基、—CO2NR7R8、—SO2NR7R8、—（ ）pNR7R8或—（ ）pNR7COR8； R4表示氢、羟基、C1-6烷基、C1-6烷氧基、C1-6氟烷氧基、三氟甲基、三氟甲氧基、卤素、—OSO2CF3、—（ ）pC3-6环烷基、—（ ）qOC1-6烷基或—（ ）pOC3-6环烷基； R5和R6分别独立地表示氢、C1-6烷基或与它们连接的氮或其他原子一起形成氮杂环烷基或氧代取代的氮杂环烷基环； R7和R8分别独立地表示氢或C1-6烷基； m和n分别独立地表示选自1和2的整数； p独立地表示选自0、1、2和3的整数； q独立地表示选自1、2和3的整数； 或其药学上可接受的盐或溶剂，但排除8-羟基-3-甲基-7-苯基磺酰基-2,3,4,5-四氢-1H-3-苯并哌嗪、8-羟基-7-4-（羟基苯基）磺酰基-2,3,4,5-四氢-1H-3-苯并哌嗪、7-苯基磺酰基-1,2,3,4-四氢异喹啉和7-苯基磺酰基-1,2,3,4-四氢异喹啉盐酸盐化合物。该化合物在治疗中有用，特别是作为抗精神病药物。
• 7-Phenylsulfonyl-Tetrahydro-3-Benzazepine Dervatives as Antipsychotic Agents
  申请人：Forbes Thomson Ian

  公开号：US20070225276A1

  公开（公告）日：2007-09-27

  The invention provides one or more chemical entities selected from a compound of formula (I): wherein R 1 represents C 1-6 alkyl, C 1-6 alkoxy, trifluoromethyl, trifluoromethoxy, halo, cyano, 5-methyl-1,2,4-oxadiazol-3-yl or a group —SO 2 X; R 2 represents hydrogen, C 1-6 alkyl, C 1-6 alkoxy, halo or cyano; X is C 1-6 alkyl, —NR 3 R 4 or morpholino; R 3 and R 4 independently represent hydrogen or C 1-6 alkyl; and a pharmaceutically acceptable salt and solvate thereof; with the proviso that the compound 8-[4-(4-fluoro-benzyl)-benzenesulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl}-dimethyl-amine is excluded. The compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof are useful in therapy, in particular as antipsychotic agents.

  本发明提供了一种或多种化学实体，所述化学实体从式(I)的化合物中选择：其中，R1代表C1-6烷基，C1-6烷氧基，三氟甲基，三氟甲氧基，卤素，氰基，5-甲基-1,2,4-噁二唑-3-基或基团-SO2X；R2代表氢，C1-6烷基，C1-6烷氧基，卤素或氰基；X代表C1-6烷基，-NR3R4或吗啡环；R3和R4独立地代表氢或C1-6烷基；以及其药学上可接受的盐和溶剂，但式8-[4-(4-氟苯甲基)-苯磺酰基]-3-甲基-2,3,4,5-四氢-1H-3-苯并氮杂环-7-基}-二甲基胺被排除在外。式(I)的化合物及其药学上可接受的盐和溶剂在治疗中有用，特别是作为抗精神病药物。