(S)-(-)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine | 153341-22-1

• 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: (S)-(-)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine
• 英文别名: (S)-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine；(-)-sibutramine；sibutramine；(S)-sibutramine；(S)-N-{1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine；(1S)-1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine
• CAS: 153341-22-1
• 化学式: C₁₇H₂₆ClN
• 分子量: 279.853
• InChiKey: UNAANXDKBXWMLN-INIZCTEOSA-N

物化性质

• 沸点：
  342.6±25.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

(S)-西布曲明的人体代谢物包括去甲西布曲明。

(S)-Sibutramine has known human metabolites that include Desmethylsibutramine.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine 以95的产率得到（-）-去甲基西布曲明
  参考文献：
  名称：

  Org. Process Res. Dev. 2006, 10, 327-333

  摘要：

  DOI：
• 作为产物：
  描述：

  西布曲明 在 L-dibenzoyltartrate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (S)-(-)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine
  参考文献：
  名称：

  对映体纯西布曲明及其主要代谢物的首次制备，并通过单晶X射线分析确定其绝对构型

  摘要：

  用二苯甲酰基-d-酒石酸拆分外消旋的西布曲明，并通过其酒石酸二苯甲酰基酯的单晶X射线晶体学测定西布曲明的绝对立体化学。主要的活性代谢物（去甲基西布曲明）是通过将西布曲明用DEAD脱甲基而获得的。西布曲明的对映体纯度通过Ultron ES-OVM柱上的HPLC测定。

  DOI：

  10.1016/s0957-4166(99)00511-x

文献信息

• SUBSTITUTED THIAZOLIDINEDIONE INDAZOLES, INDOLES AND BENZOTRIAZOLES AS ESTROGEN-RELATED RECEPTOR-a MODULATORS
  申请人：Bignan Gilles

  公开号：US20110294780A1

  公开（公告）日：2011-12-01

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  本发明涉及式(I)的化合物，制备这些化合物的方法，组合物，中间体及其衍生物，并用于治疗包括但不限于强直性脊柱炎，动脉粥样硬化，关节炎（如类风湿关节炎，感染性关节炎，儿童关节炎，银屑病性关节炎，反应性关节炎），与骨相关的疾病（包括与骨形成有关的疾病），乳腺癌（包括对抗雌激素治疗无效的癌症），心血管疾病，软骨相关疾病（如软骨损伤/丧失，软骨退化以及与软骨形成有关的疾病），软骨发育不良，软骨肉瘤，慢性腰部损伤，慢性支气管炎，慢性炎症性气道疾病，慢性阻塞性肺疾病，糖尿病，能量稳态紊乱，痛风，假性痛风，脂质紊乱，代谢综合征，多发性骨髓瘤，肥胖，骨关节炎，遗传性骨发育不全，骨溶解性骨转移，软骨软化症，骨质疏松症，帕金森病，牙周病，多肌痛风，Reiter综合征，重复性应激损伤，高血糖，血糖水平升高和胰岛素抵抗等病症的方法。
• SUBSTITUTED PHENOXY N-ALKYLATED THIAZOLIDINEDIONES AS ESTROGEN RELATED RECEPTOR-ALPHA MODULATORS
  申请人：Gaul Michael

  公开号：US20080286265A1

  公开（公告）日：2008-11-20

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  本发明涉及化合物的公式（I），制备这些化合物的方法，组合物，中间体及其衍生物，用于治疗包括但不限于强直性脊柱炎，动脉粥样硬化，关节炎（如类风湿性关节炎，感染性关节炎，儿童关节炎，银屑病性关节炎，反应性关节炎），与骨相关的疾病（包括与骨形成有关的疾病），乳腺癌（包括对抗雌激素治疗无效的癌症），心血管疾病，软骨相关疾病（如软骨损伤/丧失，软骨退化，以及与软骨形成有关的疾病），软骨发育不全，软骨肉瘤，慢性背部损伤，慢性支气管炎，慢性炎症性气道疾病，慢性阻塞性肺病，糖尿病，能量稳态紊乱，痛风，假性痛风，脂质紊乱，代谢综合征，多发性骨髓瘤，肥胖，骨关节炎，成骨不全症，骨溶解性骨转移，软骨软化症，骨质疏松症，Paget病，牙周病，多肌痛风，Reiter综合征，重复性应激损伤，高血糖，血糖水平升高和胰岛素抵抗等病症的条件。
• SUBSTITUTED PHENOXY AMINOTHIAZOLONES as estrogen related receptor-alpha modulators
  申请人：Gaul Michael

  公开号：US20080221179A1

  公开（公告）日：2008-09-11

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  本发明涉及式（I）的化合物，制备这些化合物的方法，组合物，中间体及其衍生物，并用于治疗包括但不限于强直性脊柱炎，动脉粥样硬化，关节炎（如类风湿性关节炎，感染性关节炎，儿童关节炎，银屑病性关节炎，反应性关节炎），与骨相关的疾病（包括与骨形成有关的疾病），乳腺癌（包括对抗雌激素治疗无效的癌症），心血管疾病，软骨相关疾病（如软骨损伤/缺失，软骨退变以及与软骨形成有关的疾病），软骨发育不良，软骨肉瘤，慢性背部损伤，慢性支气管炎，慢性炎性气道疾病，慢性阻塞性肺疾病，糖尿病，能量稳态紊乱，痛风，假性痛风，脂质紊乱，代谢综合征，多发性骨髓瘤，肥胖，骨关节炎，成骨不全症，骨转移性溶骨病，软骨软化症，骨质疏松症，帕金森病，牙周病，多肌痛风，Reiter综合征，重复性应力损伤，高血糖，血糖水平升高以及胰岛素抵抗等情况的治疗。
• Therapeutic agents
  申请人：——

  公开号：US20030130355A1

  公开（公告）日：2003-07-10

  The present invention provides a method of treating and preventing obesity and related co-morbid conditions comprising the administration of a therapeutically effective amount of one or more monoamine reuptake inhibitors which are serotonin reuptake inhibitors and/or noradrenaline reuptake inhibitors and a 5-HT 1A agonist to a patient in need thereof.

  本发明提供了一种治疗和预防肥胖及相关共病症的方法，包括向需要此类治疗的患者给予一种或多种单胺再摄取抑制剂，这些抑制剂是选择性5-羟色胺再摄取抑制剂和/或去甲肾上腺素再摄取抑制剂，以及一种5-HT1A受体激动剂的治疗有效量。
• Pharmaceutical composition comprising crystalline sibutramine methanesulfonate hemihydrate
  申请人：——

  公开号：US20040068018A1

  公开（公告）日：2004-04-08

  The present invention relates to a pharmaceutical composition for treating or preventing obesity, comprising novel crystalline sibutramine methanesulfonate hemihydrate of formula (I). The crystalline sibutramine methanesulfonate hemihydrate according to the present invention has a much higher solubility in water, and enhanced stability under a high humidity/temperature condition, as compared with sibutramine hydrochloride monohydrate. 1

  本发明涉及一种用于治疗或预防肥胖症的药物组合物，包括式(I)的新型晶体硫酸甲磺酰西布曲明半水合物。根据本发明的晶体硫酸甲磺酰西布曲明半水合物与盐酸单水合物相比，在水中的溶解度更高，并在高湿度/高温环境下具有增强的稳定性。