2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexylidene]-1,3-dithiane | 153260-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexylidene]-1,3-dithiane
• 英文别名: 1-(3-cyclopentyloxy-4-methoxyphenyl)-4-(1,3-dithian-2-ylidene)cyclohexane-1-carbonitrile
• CAS: 153260-05-0
• 化学式: C₂₃H₂₉NO₂S₂
• 分子量: 415.621
• InChiKey: CTTDAQKIBDQRFX-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  617.5±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexylidene]-1,3-dithiane 在 氢氧化钾 、 高氯酸 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 45.5h， 生成 Cilomilast
  参考文献：
  名称：

  1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma

  摘要：

  Evaluation of a variety of PDE4 inhibitors in a series of cellular and in vivo assays suggested a strategy to improve the therapeutic index of PDE4 inhibitors by increasing their selectivity for the ability to inhibit PDE4 catalytic activity versus the ability to compete for high affinity [H-3]rolipram-binding sites in the central nervous system. Use of this strategy led ultimately to the identification of cis-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1 -carboxylic acid (1, SB 207499, Ariflo(TM)), a potent second-generation inhibitor of PDE4 with a decreased potential for side effects versus the archetypic first generation inhibitor, (R)-rolipram.

  DOI：

  10.1021/jm970090r
• 作为产物：
  描述：

  在 正丁基锂 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 5.33h， 生成 2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexylidene]-1,3-dithiane
  参考文献：
  名称：

  1,4-Cyclohexanecarboxylates:  Potent and Selective Inhibitors of Phosophodiesterase 4 for the Treatment of Asthma

  摘要：

  Evaluation of a variety of PDE4 inhibitors in a series of cellular and in vivo assays suggested a strategy to improve the therapeutic index of PDE4 inhibitors by increasing their selectivity for the ability to inhibit PDE4 catalytic activity versus the ability to compete for high affinity [H-3]rolipram-binding sites in the central nervous system. Use of this strategy led ultimately to the identification of cis-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1 -carboxylic acid (1, SB 207499, Ariflo(TM)), a potent second-generation inhibitor of PDE4 with a decreased potential for side effects versus the archetypic first generation inhibitor, (R)-rolipram.

  DOI：

  10.1021/jm970090r

文献信息

• Compounds useful for treating allergic and inflammatory diseases
  申请人：SmithKline Beecham Corporation

  公开号：US05552438A1

  公开（公告）日：1996-09-03

  Novel compounds of Formula (I) ##STR1## where X.sub.4 is a substituted cyclohexane or cyclohexane group and the other radicals are defined herein. These compounds inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production. The compounds of the present invention are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase IV and are therefore useful in the treatment of disease states in need of mediation or inhibition thereof.

  化合物的新颖结构如下式（I）##STR1##其中X.sub.4是取代的环己烷或环己烷基团，其他基团在此有定义。这些化合物抑制肿瘤坏死因子的产生，并可用于治疗由TNF产生介导或加重的疾病状态。本发明的化合物还可用于介导或抑制磷酸二酯酶IV的酶活性，因此可用于治疗需要介入或抑制的疾病状态。
• [EN] COMPOUNDS USEFUL FOR TREATING ALLERGIC AND INFLAMMATORY DISEASES<br/>[FR] COMPOSES DESTINES A TRAITER LES MALADIES ALLERGIQUES ET INFLAMMATOIRES
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1993019749A1

  公开（公告）日：1993-10-14

  (EN) Novel compounds of formula (I) are described herein. These compounds inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production. The compounds of the present invention are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase IV and are therefore useful in the treatment of disease states in need of mediation or inhibition thereof.(FR) Nouveaux composés de la formule (I) qui inhibent la production du facteur nécrosant de tumeurs malignes (TNF) et sont utiles dans le traitement d'états pathologiques provoqués ou exacerbés par la production de TNF. Les composés de la présente invention sont également utiles dans la médiation ou l'inhibition de l'activité enzymatique ou catalytique de la phosphodiestérae IV et sont donc utiles dans le traitement de pathologies nécessitant la médiation ou l'inhibition de ladite phosphodiestérae IV.

  (中文) 本文描述了公式(I)的新化合物。这些化合物抑制肿瘤坏死因子的产生，并且在治疗由TNF产生介导或加重的疾病状态中非常有用。本发明的化合物还在介导或抑制磷酸二酯酶IV的酶活性或催化活性方面非常有用，因此在需要介导或抑制该酶的疾病状态的治疗中也非常有用。
• Compounds
  申请人：SmithKline Beecham Corporation

  公开号：US06013827A1

  公开（公告）日：2000-01-11

  This invention relates to componds of formula I ##STR1## which are useful as PDE IV inhibitors and for treating diseases related thereto.

  本发明涉及式I的化合物，其为PDE IV抑制剂，用于治疗相关疾病。##STR1##
• Process for preparing phenylcyclohexan-1-ylcarboxylic acids
  申请人：SmithKline Beecham Corporation

  公开号：EP1279662A1

  公开（公告）日：2003-01-29

  This invention relates to a process for preparing the ketone of formula II where R1 is hydrogen or another a substitutent, which process comprises cyclizing a compound of formula A where alk is alkyl of 1 to 6 carbon atoms.

  本发明涉及一种制备式 II 酮的工艺 其中 R1 为氢或另一种取代基，该工艺包括环化式 A 的化合物 其中烷基为 1 至 6 个碳原子的烷基。
• Compounds usefulfor treating allergic and inflammatory diseases
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1420011A1

  公开（公告）日：2004-05-19

  Certain compounds of formulae (I) and (IA) are disclosed for use in the treatment and prophylaxis of arthritic conditions.

  式 (I) 和 (IA) 的某些化合物 公开了用于治疗和预防关节炎的化合物。