3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole | 147009-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole
• 英文别名: 6-(1,3-dioxoisoindol-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-3-carbonitrile
• CAS: 147009-18-5
• 化学式: C₂₁H₁₅N₃O₂
• 分子量: 341.369
• InChiKey: ZTGANYFYBANFDE-UHFFFAOYSA-N

物化性质

• 沸点：
  589.4±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole 生成 (±)-3-amino-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile
  参考文献：
  名称：

  Tetrahydrocarbazole derivatives for the manufacture of a medicament for the treatment of a disease where a 5-HT1-like agonist is indicated

  摘要：

  使用通式（I）的化合物，其中：R¹代表氢、卤素、三氟甲基、硝基、羟基、C₁₋₆烷基、C₁₋₆烷氧基、芳基C₁₋₆烷氧基、-CO₂R⁴、-(CH₂)nCN、-(CH₂)nCONR⁵R6、-(CH₂)nSO₂NR⁵R6、C₁₋₆烷酰胺基(CH₂)n或C₁₋₆烷基磺酰胺基(CH₂)n；R⁴代表氢、C₁₋₆烷基或芳基C₁₋₆烷基；R⁵和R⁶分别独立地代表氢或C₁₋₆烷基，或R⁵和R⁶与它们所连接的氮原子一起形成一个环；n代表0、1或2；而R²和R³分别独立地代表氢、C₁₋₆烷基或苯甲基，或与它们所连接的氮原子一起形成吡咯烷基、哌啶基或六氢杂环庚基；或其生理上可接受的盐，在制备治疗5-HT₁样受体激动剂适用的病症的药物方面使用，例如偏头痛。还描述了通式（I）的新化合物、制备它们的方法以及含有它们的制药组合物。

  公开号：

  EP0603432A1
• 作为产物：
  描述：

  N-乙氧羰基邻苯二甲酰亚胺 在 sodium acetate 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 生成 3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  （+/-）3-氨基-6-羧酰胺基-1,2,3,4-四氢咔唑：5-羧酰胺基色胺的构象受限类似物，对5-羟色胺5-HT1D受体具有选择性。

  摘要：

  DOI：

  10.1021/jm00065a015

文献信息

• Use of tetrahydrocarbazone derivatives as 5HT.sub.1 receptor agonists
  申请人：SmithKline Beecham P.L.C.

  公开号：US05464864A1

  公开（公告）日：1995-11-07

  ##STR1## Use of a compound of general formula (I), wherein R.sup.1 represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, arylC.sub.1-6 alkoxy, --CO.sub.2 R.sup.4, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, --(CH.sub.2).sub.n SO.sub.2 NR.sup.5 R.sup.6, C.sub.1-6 alkanoylamino(CH.sub.2).sub.n, or C.sub.1-6 alkylsulphonylamino(CH.sub.2).sub.n ; R.sup.4 represents hydrogen, C.sub.1-6 alkyl or arylC.sub.1-6 alkyl; R.sup.5 and R.sup.6 each independently represent hydrogen or C.sub.1-6 alkyl, or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached form a ring; n represents 0, 1 or 2; and R.sup.2 and R.sup.3 each independently represent hydrogen, C.sub.1-6 alkyl; or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring; or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of a condition where a 5-HT.sub.1 -like agonist is indicated, for example migraine. Novel compounds of formula (I), processes for preparing them and pharmaceutical compositions containing them are also described.

  在制备治疗5-HT1-样受体激动剂适用的药物时，使用通式（I）的化合物，其中R^1代表氢、卤素、三氟甲基、硝基、羟基、C1-6烷基、C1-6烷氧基、芳基C1-6烷氧基、-CO2R^4、-(CH2)nCN、-(CH2)nCONR^5R^6、-(CH2)nSO2NR^5R^6、C1-6烷酰氨基(CH2)n或C1-6烷基磺酰氨基(CH2)n；R^4代表氢、C1-6烷基或芳基C1-6烷基；R^5和R^6分别独立表示氢或C1-6烷基，或R^5和R^6与其连接的氮原子一起形成环；n代表0、1或2；R^2和R^3分别独立表示氢、C1-6烷基；或苄基，或与其连接的氮原子一起形成吡咯啉、哌啶或六氢脲环；或其生理上可接受的盐，在制备这些化合物和含有它们的药物组合物的过程中也有描述。
• Medicaments 1,2,3,4-tetrahydrocarbazoles and 5-HT.sub.1 agonist use
  申请人：Smithkline Beecham plc

  公开号：US05827871A1

  公开（公告）日：1998-10-27

  Use of a compound of general formula (I): ##STR1## wherein R.sup.1 represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, arylC.sub.1-6 alkoxy, --CO.sub.2 R.sup.4, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, --(CH.sub.2).sub.n SO.sub.2 NR.sup.5 R.sup.6, C.sub.1-6 alkanoylamino(CH.sub.2).sub.n, or C.sub.1-6 alkylsulphonylamino(CH.sub.2).sub.n ; R.sup.4 represents hydrogen, C.sub.1-6 alkyl or arylC.sub.1-6 alkyl; R.sup.5 and R.sup.6 each independently represent hydrogen or C.sub.1-6 alkyl, or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached form a ring; n represents 0, 1 or 2; and R.sup.2 and R.sup.3 each independently represent hydrogen, C.sub.1-6 alkyl or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring; or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of a condition where a 5-HT.sub.1 -like agonist is indicated, for example migraine. Novel compounds of formula (I), processes for preparing them and pharmaceutical compositions containing them are also described.

  将通用公式(I)的化合物用于制造药物，用于治疗需要5-HT1样受体激动剂的情况，例如偏头痛。公式(I)的新化合物、制备它们的方法以及含有它们的药物组成物也有描述。
• [EN] USE OF TETRAHYDROCARBAZONE DERIVATIVES AS 5HT1 RECEPTOR AGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1993000086A1

  公开（公告）日：1993-01-07

  (EN) Use of a compound of general formula (I), wherein R1 represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C1-6alkyl, C1-6alkoxy, arylC1-6alkoxy, -CO2R4, -(CH2)nCN, -(CH2)nCONR5R6, -(CH2)nSO2NR5R6, C1-6alkanolyamino(CH2)n, or C1-6alkylsulphonylamino(CH2)n; R4 represents hydrogen, C1-6alkyl or arylC1-6alkyl; R5 and R6 each independently represent hydrogen or C1-6¿alkyl, or R5 and R6 together with the nitrogen atom to which they are attached form a ring; n represents 0, 1 or 2; and R2 and R3 each independently represent hydrogen, C¿1-6alkyl or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring; or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of a condition where a 5-HT1-like agonist is indicated, for example migraine. Novel compounds of formula (I), processes for preparing them and pharmaceutical compositions containing them are also described.(FR) Utilisation d'un composé de la formule (I) dans laquelle R1 représente hydrogène, halogène, trifluorométhyle, nitro, hydroxy, C1-6alkyle, C1-6alcoxy, arylC1-6alcoxy, -CO2R4, -(CH2)nCN, -(CH2)nCONR5R6, -(CH2)nSO2NR5R6, C1-6alcanoylamino(CH2)n, ou C1-6alkylsulphonylamino(CH2)n; R4 représente hydrogène, C1-6alkyle ou arylC1-6alkyle; R5 et R6 représentent chacun indépendamment hydrogène ou C1-6alkyle, ou R5 et R6 forment avec l'atome d'azote auquel ils sont attachés une chaîne fermée, n représente 0, 1 ou 2; et R2 et R3 représentent chacun indépendamment hydrogène, C1-6alkyle ou benzyle ou forment avec l'atome d'azote auquel ils sont attachés une chaîne fermée pyrrolidino, pipéridino ou hexahydroazépino; ou d'un sel physiologiquement acceptable de ce composé, dans la fabrication d'un médicament destiné au traitement d'états tels que la migraine où un agoniste analogue au 5-HT1 est prescrit. Des composés de la formule (I), leurs procédés de préparation et des compositions pharmaceutiques les contenant sont également décrits.

  使用通式（I）的化合物，其中R1代表氢，卤素，三氟甲基，硝基，羟基，C1-6烷基，C1-6烷氧基，芳基C1-6烷氧基，-CO2R4，-(CH2)nCN，-(CH2)nCONR5R6，-(CH2)nSO2NR5R6，C1-6酰胺基(CH2)n或C1-6烷基磺酰胺基(CH2)n; R4代表氢，C1-6烷基或芳基C1-6烷基; R5和R6各自独立地表示氢或C1-6烷基，或者R5和R6与它们所连接的氮原子一起形成一个环; n表示0，1或2; R2和R3各自独立地表示氢，C1-6烷基或苄基，或者与它们所连接的氮原子一起形成吡咯烷，哌啶或六氢噁唑环; 或其生理上可接受的盐，在制造用于治疗需要5-HT1样受体激动剂的情况的药物中，例如偏头痛。还描述了通式（I）的新化合物、制备它们的方法以及含有它们的制药组合物。
• Enantiomers of carbazole derivatives as 5-HT.sub.1 -like agonists
  申请人：SmithKline Beecham plc

  公开号：US05616603A1

  公开（公告）日：1997-04-01

  A (+)or (-) enantiomer of a compound of formula (I) wherein R.sup.4 is methyl or ethyl, or a salt, solvate or hydrate thereof, processes for preparing said compounds and pharmaceutical compositions containing them. Compounds of formula (+) are 5-HT.sub.1 -like agonists.

  化合物公式（I）的A（+）或（-）对映体，其中R.sup.4是甲基或乙基，或其盐，溶剂合物或水合物，制备该化合物的方法以及含有它们的药物组合物。公式（+）的化合物是5-HT.sub.1-类似激动剂。
• Medicaments
  申请人：SmithKline Beecham p.l.c.

  公开号：US05637611A1

  公开（公告）日：1997-06-10

  Use of a compound of general formula (I): ##STR1## wherein: R.sup.1 represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, arylC.sub.1-6 alkoxy, --CO.sub.2 R.sup.4, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, --(CH.sub.2).sub.n SO.sub.2 NR.sup.5 R.sup.6, C.sub.1-6 alkanoylamino (CH.sub.2).sub.n, or C.sub.1-6 alkylsulphonylamino (CH.sub.2).sub.n ; R.sup.4 represents hydrogen, C.sub.1-6 alkyl or arylC.sub.1-6 alkyl; R.sup.5 and R.sup.6 each independently represent hydrogen or C.sub.1-6 alkyl, or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached form a ring; n represents 0, 1 or 2; and R.sup.2 and R.sup.3 each independently represent hydrogen, C.sub.1-6 alkyl or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring; or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of a condition where a 5-HT.sub.1 -like agonist is indicated, for example migraine. Novel compounds of formula (I), processes for preparing them and pharmaceutical compositions containing them are also described.

  使用一般式(I)的化合物：##STR1## 其中：R.sup.1代表氢，卤素，三氟甲基，硝基，羟基，C.sub.1-6烷基，C.sub.1-6烷氧基，芳基C.sub.1-6烷氧基，--CO.sub.2R.sup.4，--(CH.sub.2).sub.n CN，--(CH.sub.2).sub.n CONR.sup.5 R.sup.6，--(CH.sub.2).sub.n SO.sub.2NR.sup.5 R.sup.6，C.sub.1-6烷酰胺基(CH.sub.2).sub.n或C.sub.1-6烷基磺酰胺基(CH.sub.2).sub.n; R.sup.4代表氢，C.sub.1-6烷基或芳基C.sub.1-6烷基; R.sup.5和R.sup.6各自独立地代表氢或C.sub.1-6烷基，或R.sup.5和R.sup.6与它们连接的氮原子一起形成一个环; n代表0、1或2; R.sup.2和R.sup.3各自独立地代表氢、C.sub.1-6烷基或苄基，或者与它们连接的氮原子一起形成吡咯烷，哌啶或六氢噁唑环; 或其生理上可接受的盐，在制造治疗5-HT.sub.1样受体激动剂适用的情况下的药物中，例如偏头痛。还描述了公式(I)的新化合物、制备它们的过程和含有它们的药物组成物。