1-(1-四氯苯基)-3-甲基-1-丁胺 | 84467-54-9

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(1-四氯苯基)-3-甲基-1-丁胺
• 中文别名: 1-(1-(4-氯苯基))-alpha-(2-甲基丙基)环丁烷甲胺
• 英文名称: didesmethylsibutramine
• 英文别名: 1-[1-(4-chlorophenyl)-cyclobutyl]-3-methylbutylamine；(-)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine；1-(1-(4-chlorophenyl)cyclobutyl)-3-methylbutan-1-amine；1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine；1-[1-(4-chlorphenyl)cyclobutyl]-3-methylbutylamine；1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine
• CAS: 84467-54-9
• 化学式: C₁₅H₂₂ClN
• 分子量: 251.799
• InChiKey: WQSACWZKKZPCHN-UHFFFAOYSA-N

物化性质

• 沸点：
  337.9±25.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

1-[1-(4-氯苯基)环丁基]-3-甲基丁胺是人类已知代谢物去甲西布曲明的(S)-异构体。

1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine is a known human metabolite of Desmethylsibutramine, (S)-.

来源:NORMAN Suspect List Exchange

安全信息

• 储存条件：
  存储条件：2-8℃，避光，惰性气体环境中保存。

反应信息

• 作为反应物：
  描述：

  1-(1-四氯苯基)-3-甲基-1-丁胺 以62的产率得到西布曲明
  参考文献：
  名称：

  包含西布曲明甲磺酸盐半水合物晶体的药物组合物

  摘要：

  本发明涉及用于治疗或者预防肥胖的药物组合物，其包括式(I)的新型西布曲明甲磺酸盐半水合物晶体。与西布曲明盐酸盐单水合物相比，根据本发明的西布曲明甲磺酸盐半水合物晶体在水中具有更高的溶解度，而且在高湿度/温度条件下具有增强的稳定性。

  公开号：

  CN1688297A
• 作为产物：
  描述：

  Magnesium;[1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylidene]azanide;chloride 在 硼烷四氢呋喃络合物 、 邻苯二甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到1-(1-四氯苯基)-3-甲基-1-丁胺
  参考文献：
  名称：

  Novel diacid accelerated borane reducing agent for imines

  摘要：

  A remarkable effect of diacids in modulating the reactivity of borane has been discovered. This novel process provides a rapid and excellent access for reduction of a variety of imines with different functionalities. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01905-6

文献信息

• Compositions, Synthesis, and Methods of Using Cycloalkylmethylamine Derivatives
  申请人：Bhat Laxminarayan

  公开号：US20120172426A1

  公开（公告）日：2012-07-05

  The present invention provides novel cycloalkylmethylamine derivatives, and methods of preparing cycloalkylmethylamine derivatives. The present invention also provides methods of using cycloalkylmethylamine derivatives and compositions of cycloalkylmethylamine derivatives. The pharmaceutical compositions of the compounds of the present invention can be advantageously used for treating and/or preventing obesity and obesity related co-morbid indications and depression and depression related co-morbid indications.

  本发明提供了新颖的环烷基甲胺衍生物，以及制备环烷基甲胺衍生物的方法。本发明还提供了使用环烷基甲胺衍生物和环烷基甲胺衍生物组合物的方法。本发明化合物的药物组合物可优势用于治疗和/或预防肥胖及与肥胖相关的共病症和抑郁症及与抑郁症相关的共病症。
• Therapeutic agents
  申请人：The Boots Company PLC

  公开号：US04629727A1

  公开（公告）日：1986-12-16

  Compounds of formula I ##STR1## in which n=0 or 1; in which, when n=0, R.sub.1 is H, an alkyl, a cycloalkyl, a cycloalkylmethyl, an alkenyl or, an alkynyl group a heterocyclic ring or an optionally substituted phenyl ring or when n=1, R.sub.1 is H or an alkyl group; in which R.sub.2 and R.sub.3 are H or an alkyl group; in which A is a group of formula III --(CH.sub.2).sub.x --W--(CH.sub.2).sub.y -- III in which W is an oxygen atom or a group of formula --S(O).sub.m --, a group of formula --CR.sub.12 R.sub.13 --, a cycloalkylidene group or a cycloalkylene group; x is 0 or an integer from 1 to 5; y is 0 or an integer from 1 to 5. in which R.sub.4 is a carbocyclic ring, a heterocyclic ring, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an amido group, an acyloxy group, a hydroxy group, a thiol group, or a group of formula --OR.sub.20, --SR.sub.20, --SOR.sub.20 or SO.sub.2 R.sub.20. in which R.sub.5, R.sub.6 and R.sub.7 are H, halo, trifluoromethyl, hydroxy, an alkyl group, an alkoxy or alkylthio group, phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form an optionally substituted second benzene ring; in which R.sub.8 and R.sub.9 are H or an alkyl group containing 1 to 3 carbon atoms; and pharmaceutically acceptable salts thereof have utility in the treatment of depression. Processes for their preparation and compositions containing them are disclosed.

  化合物的化学式为I，其中n=0或1；当n=0时，R.sub.1为H、烷基、环烷基、环烷基甲基、烯基、炔基、杂环烷基、或可选择取代的苯环；当n=1时，R.sub.1为H或烷基；其中R.sub.2和R.sub.3为H或烷基；其中A为化学式III的基团--(CH.sub.2).sub.x--W--(CH.sub.2).sub.y--，其中W为氧原子或化学式--S(O).sub.m--的基团、化学式--CR.sub.12R.sub.13--的基团、环烷基亚甲基基团或环烷基亚烯基基团；x为0或1至5的整数；y为0或1至5的整数；其中R.sub.4为碳环烷基、杂环烷基、氰基、氨基甲酰基、烷氧羰基、酰胺基、醋酰氧基、羟基、硫醇基，或化学式--OR.sub.20、--SR.sub.20、--SOR.sub.20或SO.sub.2R.sub.20的基团；其中R.sub.5、R.sub.6和R.sub.7为H、卤素、三氟甲基、羟基、烷基、烷氧基或烷硫基、苯基，或R.sub.5和R.sub.6与它们连接的碳原子一起形成可选择取代的第二苯环；其中R.sub.8和R.sub.9为H或含有1至3个碳原子的烷基基团；以及其药学上可接受的盐在抑郁症治疗中具有用途。公开了其制备方法和含有它们的组合物。
• Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites
  作者：James E. Jeffery、Frank Kerrigan、Thomas K. Miller、Graham J. Smith、Gerald B. Tometzki

  DOI：10.1039/p19960002583

  日期：——

  Synthetic routes to N-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine (sibutramine) 1 and its demethylated and hydroxylated human metabolites N-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N-methylamine 2, 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine 3, 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-1-ol 4 and c-3-(1-amino-3-methylbutyl)-3-(4-chlorophenyl)cyclobutan-r-1-ol 5a are described. Key steps are tandem Grignard–reduction reactions on 1-(4-chlorophenyl)cyclobutanecarbonitrile 7 and its 3-(tetrahydropyran-2-yloxy)-substituted analogue 14 and a convenient one-pot conversion of 4-chlorophenylacetonitrile 6 into the 3-hydroxycyclobutanecarbonitrile 13.

  合成路线涉及N-1-[1-(4-氯苯基)环丁基]-3-甲基丁基}-N,N-二甲胺（西布曲明）1及其去甲基化和氢氧化的人体代谢物，包括N-1-[1-(4-氯苯基)环丁基]-3-甲基丁基}-N-甲胺2，1-[1-(4-氯苯基)环丁基]-3-甲基丁胺3，4-氨基-4-[1-(4-氯苯基)环丁基]-2-甲基丁醇4，以及c-3-(1-氨基-3-甲基丁基)-3-(4-氯苯基)环丁醇-r-1 5a。关键步骤包括对1-(4-氯苯基)环丁腈7及其3-(四氢呋喃-2-基氧)取代类似物14进行串联格氏反应-还原反应，以及将4-氯苯基乙腈6方便地一锅法转化为3-羟基环丁腈13。
• Methods and compositions for the treatment and prevention of sexual dysfunction
  申请人：Sepracor, Inc.

  公开号：US06339106B1

  公开（公告）日：2002-01-15

  Methods are disclosed for the treatment and prevention of sexual. The methods comprise the administration of a dopamine reuptake inhibitor and optionally an additional pharmacologically active compound. Pharmaceutical compositions and dosage forms are also disclosed that comprise a dopamine reuptake inhibitor and optionally an additional pharmacologically active compound. Preferred dopamine reuptake inhibitors are racemic or optically pure sibutramine metabolites and pharmaceutically acceptable salts, solvates, and clathrates thereof. Preferred additional pharmacologically active compounds include drugs that affect the central nervous system, such as 5-HT3 antagonists.

  本文披露了一种治疗和预防性功能障碍的方法。该方法包括给予多巴胺再摄取抑制剂和可选的另一种药理活性化合物。还披露了包括多巴胺再摄取抑制剂和可选的另一种药理活性化合物的药物组合物和剂型。优选的多巴胺再摄取抑制剂是外消旋或光学纯的西布曲明代谢物及其药学上可接受的盐、溶剂和包合物。优选的可选药理活性化合物包括影响中枢神经系统的药物，例如5-HT3拮抗剂。
• Methods of using sibutramine metabolites in combination with a phosphodiesterase inhibitor to treat sexual dysfunction
  申请人：Sepracor, Inc.

  公开号：US06476078B2

  公开（公告）日：2002-11-05

  Methods are disclosed for the treatment and prevention of male and female sexual function disorders which comprise a racemic or optically pure sibutramine metabolite and a phosphodiesterase inhibitor.

  揭示了一种治疗和预防男性和女性性功能障碍的方法，包括一种外消旋或光学纯的西布曲明代谢物和一种磷酸二酯酶抑制剂。