2-(5-fluoro-2-nitrophenylamino)benzo[b]thiophene-3-carbonitrile | 221060-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(5-fluoro-2-nitrophenylamino)benzo[b]thiophene-3-carbonitrile
• 英文别名: 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carbonitrile；2-(5-fluoro-2-nitroanilino)-1-benzothiophene-3-carbonitrile
• CAS: 221060-42-0
• 化学式: C₁₅H₈FN₃O₂S
• 分子量: 313.312
• InChiKey: WTEGMBXIKULAJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-fluoro-2-nitrophenylamino)benzo[b]thiophene-3-carbonitrile 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以78%的产率得到9-fluoro-11H-12-thia-6,11-diazadibenzo[a,f]azulen-5-ylamine hydrochloride
  参考文献：
  名称：

  [EN] PIPERAZINE SUBSTITUTED ARYL BENZODIAZEPINES
  [FR] ARYL BENZODIAZEPINES SUBSTITUEES PAR DE LA PIPERAZINE

  摘要：

  本文描述了以下式(I)的化合物：其中：是一个可选的苯并嵌合的五元或六元芳香环，其中含有从N、S和O中独立选择的零至三个杂原子；Alk是(C1-4)烷基或羟基取代的(C1-4)烷基；X是氧或硫；R1是氢、(C1-6)氟烷基、(C3-6)环烷基或(C1-4)烷基，其中(C1-4)烷基未取代或取代为羟基、甲氧基、乙氧基、OCH2CH2OH或-CN；R2是H、卤素、(C1-6)氟烷基、(C1-6)环烷基、OR4、SR4、N02、CN、COR4、C(O)OR4、CONR5R6、NR5R6、S02NR5R6、NR5COR4、NR5SO2R4、可选取代的芳香基或(C1-6)烷基，其中(C1-6)烷基未取代或取代为羟基；R3是氢、(C1-6)氟烷基、(C2-6)烯基、Ar、(C1-4)烷基-Ar或(C1-4)烷基，其中(C1-4)烷基未取代或取代为苯基；R4是氢、(C1-6)烷基、(C1-6)氟烷基或可选取代的芳香基；R5和R6独立地是氢、(C1-6)烷基或可选取代的芳香基，R7是氢、(C1-6)烷基、(C1-6)氟烷基或可选取代的芳香基；R8和R9独立地是氢、(C1-6)烷基或可选取代的芳香基；Ar是可选取代的苯基、萘基、单环杂芳基或双环杂芳基；Z1和Z2独立地选自氢、卤素、(C1-6)烷基、(C1-6)氟烷基、OR7、SR7、NO2、CN、COR7、CONR8R9、NR8R9和可选取代的芳香基；以及其所有盐、溶剂化合物、光学和几何异构体以及结晶形式。此外，还描述了将上述式(I)的化合物用作多巴胺D2受体拮抗剂以及用于治疗精神病和双相情感障碍的药剂，以及上述式(I)的药物配方。

  公开号：

  WO2004014895A1
• 作为产物：
  描述：

  2-氨基苯并[b]噻吩-3-甲腈 、 2,4-二氟硝基苯 在 potassium carbonate 作用下， 以 N-甲基乙酰胺 、 水 、 乙酸乙酯 为溶剂， 生成 2-(5-fluoro-2-nitrophenylamino)benzo[b]thiophene-3-carbonitrile
  参考文献：
  名称：

  Fused thiophene compounds and medicinal use thereof

  摘要：

  公式（I）的一种缩合噻吩化合物，其中每个符号如规范中定义，其药学上可接受的盐及水合物。本发明的公式（I）化合物可用作一种新型抗精神病药物，对精神分裂症的阳性症状和阴性症状均有效，与较少的副作用（如外周性运动障碍等）相关，并且与严重副作用（如粒细胞缺乏症等）的关联较小。此外，该化合物还可用作治疗阿尔茨海默病和躁郁症的药物。

  公开号：

  US06271225B1

文献信息

• Fused thiophene compounds and medicinal use thereof
  申请人：Welfide Corporation

  公开号：US06271225B1

  公开（公告）日：2001-08-07

  A condensed thiophene compound of the formula (I) wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof and hydrates thereof. The compound of the formula (I) of the present invention is useful as a novel antipsychotic agent which is effective for both positive symptoms and negative symptoms of schizophrenia, which is associated with less side effects such as extrapyramidal motor disorder and the like and which is less associated with serious side effects such as agranulocytosis and the like. In addition, this compound is also useful as a therapeutic agent of Alzheimer's disease and manic-depressive illness.

  公式（I）的一种缩合噻吩化合物，其中每个符号如规范中定义，其药学上可接受的盐及水合物。本发明的公式（I）化合物可用作一种新型抗精神病药物，对精神分裂症的阳性症状和阴性症状均有效，与较少的副作用（如外周性运动障碍等）相关，并且与严重副作用（如粒细胞缺乏症等）的关联较小。此外，该化合物还可用作治疗阿尔茨海默病和躁郁症的药物。
• Condensed thiophene compounds and pharmaceutical use thereof
  申请人：——

  公开号：US20020042411A1

  公开（公告）日：2002-04-11

  A condensed thiophene compound of the formula (I) 1 wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof and hydrates thereof. The compound of the formula (I) of the present invention is useful as a novel antipsychotic agent which is effective for both positive symptoms and negative symptoms of schizophrenia, which is associated with less side effects such as extrapyramidal motor disorder and the like and which is less associated with serious side effects such as agranulocytosis and the like. In addition, this compound is also useful as a therapeutic agent of Alzheimer's disease and manic-depressive illness.

  本发明涉及一种式(I)的缩合噻吩化合物，其中每个符号如规范中所定义，其药学上可接受的盐和水合物。本发明的式(I)化合物可用作一种新型抗精神病药物，对于精神分裂症的阳性症状和阴性症状都有效，且副作用较少，如运动障碍等，并且与严重副作用如粒细胞缺乏症等较少相关。此外，该化合物还可用作阿尔茨海默病和躁郁症的治疗剂。
• Piperazine substituted aryl benzodiazepines and their use as dopamine receptor antagonists for the treatment of psychotic disorders
  申请人：Aicher Daniel Thomas

  公开号：US20050203296A1

  公开（公告）日：2005-09-15

  Described herein are antipyschotic compounds of formula (I) wherein, A is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; Alk is (C 1-4 ) alkylene optionally substituted with OH, methoxy, ethoxy, or F; Ar is optionally substituted phenyl, naphthyl, monocyclic heteroaromatic, or bicyclic heteroaromatic; R 1 is hydrogen or (C 1-4 ) alkyl optionally substituted with OH, OR 3 , or OCH 2 CH 2 OH, wherein R 3 is (C 1-2 ) alkyl; R 2 is H, (C 1-6 ) alkyl, halogen, fluorinated (C 1-6 ) alkyl, OR 4 , SR 4 , NO 2 , CN, COR 4 , CONR 5 R 6 , SO 2 NR 5 R 6 , NR 5 R 6 , NR 5 COR 4 , NR 5 SO 2 R 4 , or optionally substituted phenyl, wherein R 4 is hydrogen, (C 1-6 ) alkyl, fluorinated (C 1-6 ) alkyl, benzyl, or optionally substituted phenyl, R 5 and R 6 are independently hydrogen, (C 1-6 ) alkyl, or optionally substituted phenyl; Z is one or two substituents independently selected from hydrogen, halogen, (C 1-6 ) alkyl, fluorinated (C 1-6 ) alkyl, OR 7 , SR 7 , NO 2 , CN, COR 7 , CONR 8 R 9 , SO 2 NR 8 R 9 , NR 8 SO 2 R 7 , NR 8 R 9 , or optionally substituted phenyl, wherein R 7 is hydrogen, (C 1-6 ) alkyl, fluorinated alkyl, benzyl, or optionally substituted phenyl, R 8 and R 9 are independently hydrogen, (C 1-6 ) alkyl, or optionally substituted phenyl; and salts, solvates, and crystal forms thereof. Also described are the use of the compounds of formula (a) as antagonists of the dopamine D 2 receptor and as agents for the treatment of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I). Also described are compounds useful as intermediates for the synthesis of the compounds of formula (I).

  本文描述了式（I）的抗精神病化合物，其中A是一个选择性地与N、O和S中的零到三个杂原子独立选定的五元或六元芳香环，可以与苯并联；Alk是（C1-4）的烷基，可以选择性地用OH，甲氧基，乙氧基或F取代；Ar是选择性取代的苯基，萘基，单环杂芳基或双环杂芳基；R1是氢或（C1-4）烷基，可以选择性地用OH，OR3或OCH2CH2OH取代，其中R3是（C1-2）烷基；R2是H，（C1-6）烷基，卤素，氟化的（C1-6）烷基，OR4，SR4，NO2，CN，COR4，CONR5R6，SO2NR5R6，NR5R6，NR5COR4，NR5SO2R4或选择性取代的苯基，其中R4是氢，（C1-6）烷基，氟化的（C1-6）烷基，苄基或选择性取代的苯基，R5和R6独立地是氢，（C1-6）烷基或选择性取代的苯基；Z是一个或两个取代基，独立选择自氢，卤素，（C1-6）烷基，氟化的（C1-6）烷基，OR7，SR7，NO2，CN，COR7，CONR8R9，SO2NR8R9，NR8SO2R7，NR8R9或选择性取代的苯基，其中R7是氢，（C1-6）烷基，氟化的烷基，苄基或选择性取代的苯基，R8和R9独立地是氢，（C1-6）烷基或选择性取代的苯基；以及其盐，溶剂化合物和晶体形式。本文还描述了将式（a）的化合物用作多巴胺D2受体的拮抗剂以及用于治疗精神病和双相障碍的药物，以及式（I）的化合物的制药配方。还描述了用于合成式（I）的化合物的中间体。
• Piperazine substituted aryl benzodiazepines
  申请人：Aicher Daniel Thomas

  公开号：US20060084643A1

  公开（公告）日：2006-04-20

  Described herein are compounds of formula (I) use of the compounds of formula (I) as antagonists of the dopamine D2 receptor and as agents for the treament of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I).

  本文描述了公式(I)的化合物。该化合物可用作多巴胺D2受体拮抗剂和治疗精神病和双相障碍的药物，并提供公式(I)的药物制剂。
• FUSED THIOPHENE COMPOUNDS AND MEDICINAL USE THEREOF
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP1016664A1

  公开（公告）日：2000-07-05

  A condensed thiophene compound of the formula (I) wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof and hydrates thereof. The compound of the formula (I) of the present invention is useful as a novel antipsychotic agent which is effective for both positive symptoms and negative symptoms of schizophrenia, which is associated with less side effects such as extrapyramidal motor disorder and the like and which is less associated with serious side effects such as agranulocytosis and the like. In addition, this compound is also useful as a therapeutic agent of Alzheimer's disease and manic-depressive illness.

  式 (I) 的缩合噻吩化合物 其中各符号如说明书中所定义，其药学上可接受的盐及其水合物。本发明的式(I)化合物可作为一种新型抗精神病药物，对精神分裂症的阳性症状和阴性症状均有效，副作用较少，如锥体外系运动障碍等，严重副作用较少，如粒细胞减少等。此外，该化合物还可用作阿尔茨海默病和躁狂抑郁症的治疗剂。