3-(cyclopentyloxy)-4-methoxybenzaldehyde oxime | 162279-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(cyclopentyloxy)-4-methoxybenzaldehyde oxime
• 英文别名: 3-Cyclopentyloxy-4-methoxy-benzaldehyde-oxime；3-cyclopentyloxy-4-methoxy-benzaldehyde oxime；3-cyclopentyloxy-4-methoxybenzaldehyde oxime；N-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]hydroxylamine
• CAS: 162279-48-3
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: YQQKXLPORQRQOR-UHFFFAOYSA-N

物化性质

• 熔点：
  54 °C
• 沸点：
  359.9±32.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(cyclopentyloxy)-4-methoxybenzaldehyde oxime 在 吡啶 、 氢氧化钾 、 N-氯代丁二酰亚胺 、 草酰氯 、 TEA 作用下， 以 甲醇 、 苯 为溶剂， 生成 (5R)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-methyl-N-[(1S)-1-phenylethyl]-4H-1,2-oxazole-5-carboxamide
  参考文献：
  名称：

  异羟肟酸取代对两个系列咯利普兰类似物的磷酸二酯酶4型（PDE4）和TNFα抑制活性的显着影响：对PDE4新活性位点模型的影响。

  摘要：

  DOI：

  10.1021/jm970685m
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 盐酸羟胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以64%的产率得到3-(cyclopentyloxy)-4-methoxybenzaldehyde oxime
  参考文献：
  名称：

  Substituted pteridines for the treatment of inflammatory diseases

  摘要：

  该发明涉及新的蕨类素，适用于治疗呼吸系统或消化系统的疾病或不适，关节、皮肤或眼睛的炎症性疾病，外周或中枢神经系统的疾病或癌症，以及含有这些化合物的药物组合物。

  公开号：

  US20060116373A1

文献信息

• Purine derivatives having phosphodiesterase iv inhibition activity
  申请人：Euro-Celtique, S.A.

  公开号：US06413975B1

  公开（公告）日：2002-07-02

  Disclosed are compounds of the formula: wherein R3, R6a, R6b and R8 are substituted as disclosed herein. The compounds are effective in effecting PDE IV inhibition in patients in need thereof.

  揭示了以下化合物：其中R3、R6a、R6b和R8如本文所述被取代。这些化合物对需要PDE IV抑制作用的患者有效。
• Purine derivatives having phosphodiesterase IV inhibition activity
  申请人：Euro-Celtique, S.A.

  公开号：US06319928B1

  公开（公告）日：2001-11-20

  A compound of the formula: wherein R2 is O or S; R3, R6a and R8 are the same or different and each represent a C1-8 alkyl which is unbranched or branched and unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; C3-8 cycloalkyl which is unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; C4-8 cycloalkylalkyl wherein the cycloalkyl portion is unsubstituted or substituted with OH, alkoxy, CO2H, ═NOH, ═NOCONH2, or ═O; aryl which is unsubstituted or substituted with Cl, NH2, alkylamino, dialkylamino, amido, C1-C8 alkylamido, C1-C3 dialkylamido, OH, alkoxy, HC═NOH, HC═NOCONH2, C1-C3 alkyl, phenyl or benzyl; aralkyl (C1-4); heterocyclyl; heterocyclylalkyl (C1-C4); and heteroaryl; R6b represents a H or R6a, or together R6b, N, and R6a make a 3 to 8 member ring containing at least one carbon, from one to three nitrogen atoms, from zero to two oxygen atoms, from zero to two sulfur atoms, said ring optionally substituted with alkoxy, CO2H, CONH2, ═NOH, ═NOCONH2, ═O; and where aryl is phenyl or naphthyl, the heterocyclyl is a 5, 6 or 7 membered ring including from one to three nitrogen atoms, and from zero to two oxygen atoms, from zero to two sulfur atoms, and can be substituted as in aryl on the carbons or nitrogens of that ring; or a pharmaceutically acceptable salt thereof, provided that when R3 is propyl, R8 is not cyclopentyl, noradamantyl, or dicyclopropylmethyl.

  该化合物的结构式如下：其中R2为O或S；R3、R6a和R8相同或不同，分别代表未支链或支链的C1-8烷基，未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；C3-8环烷基，未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；C4-8环烷基烷基，其中环烷基部分未取代或取代为OH、烷氧基、CO2H、═NOH、═NOCONH2或═O；芳基未取代或取代为Cl、NH2、烷基氨基、二烷基氨基、酰胺、C1-C8烷基酰胺、C1-C3二烷基酰胺、OH、烷氧基、HC═NOH、HC═NOCONH2、C1-C3烷基、苯基或苄基；芳基烷基（C1-4）；杂环烷基；杂环烷基烷基（C1-C4）；和杂芳基；R6b代表H或R6a，或者一起R6b、N和R6a构成含有至少一个碳、从一个到三个氮原子、从零到两个氧原子、从零到两个硫原子的3到8成员环，该环可以取代为烷氧基、CO2H、CONH2、═NOH、═NOCONH2、═O；其中芳基为苯基或萘基，杂环烷基是包括从一个到三个氮原子和从零到两个氧原子、从零到两个硫原子的5、6或7成员环，并且可以在该环的碳或氮上取代，或其药用盐，但当R3为丙基时，R8不是环戊基、萘基或二环丙基甲基。
• [EN] NEW COMPOUNDS HAVING A SELECTIVE PDE4D INHIBITING ACTIVITY<br/>[FR] NOUVEAUX COMPOSÉS PRÉSENTANT UNE ACTIVITÉ D'INHIBITION SÉLECTIVE VIS-À-VIS DE PDE4D
  申请人：UNIVERSIT DEGLI STUDI DI GENOVA

  公开号：WO2015121212A1

  公开（公告）日：2015-08-20

  Compounds of formula (I), wherein Z = cyclopentyl. cyclopropylmethyl, -CH3; R' = -CH3, CHF2, X= formula (II) (III) (IV) (V) Y = - CO; -C=O(CH2), -CH(OH)-CH2, -CH2-C=O, -CH2-CH2-C=O; -CH2-CH(OH)-CH2, -CH2- CH(OCOR1)-CH2 NR2 = -N(CH2-CH2OH)2, formula (VI) (VII) (VIII) (IX) (X) (XI) R1 = optionally substituted C1-C8 alkyl, optionally substituted aryl; optionally substituted aralkyl, preferably C1-C3 alkyl, more preferably CH3; and enantiomers, diastereoisomers and pharmaceutically acceptable salts thereof; these compounds have a PDE4D inhibiting activity and can be used as a medicament for treating dementia, in particular Alzheimer disease, and for improving memory.

  化合物的化学式（I），其中Z = 环戊基，环丙甲基，-CH3；R' = -CH3，CHF2，X = 化学式（II）（III）（IV）（V），Y = -CO；-C=O（CH2），-CH（OH）-CH2，-CH2-C=O，-CH2-CH2-C=O；-CH2-CH（OH）-CH2，-CH2-CH（OCOR1）-CH2，NR2 = -N（CH2-CH2OH）2，化学式（VI）（VII）（VIII）（IX）（X）（XI），R1 = 可选择地取代的C1-C8烷基，可选择地取代的芳基；可选择地取代的芳基烷基，优选C1-C3烷基，更优选CH3；以及其对映体，异构体和药学上可接受的盐；这些化合物具有PDE4D抑制活性，可用作治疗痴呆症，特别是阿尔茨海默病，并改善记忆的药物。
• Inhibitors of phophodiesterase type-IV
  申请人：Palle P. Venkata

  公开号：US20050075383A1

  公开（公告）日：2005-04-07

  The present invention relates to isoxazoline derivatives, which can be used as selective inhibitors of phosphodiesterase (PDE) type IV. In particular, compounds disclosed herein can be useful in the treatment of AIDS, asthma, arthritis, bronchitis, chronic obstructive pulmonary disease (COPD), psoriasis, allergic rhinitis, shock, atopic dermatitis, Crohn's disease, adult respiratory distress syndrome (ARDS), eosinophilic granuloma, allergic conjunctivitis, osteoarthritis, ulcerative colitis and other inflammatory diseases in a patient, particularly in humans. The present invention also relates to processes for the preparation of disclosed compounds, as well as pharmaceutical compositions thereof, and their use as phosphodiesterase (PDE) type IV inhibitors.

  本发明涉及异噁唑啉衍生物，可用作选择性磷酸二酯酶（PDE）IV型抑制剂。特别是，所披露的化合物可用于治疗艾滋病、哮喘、关节炎、支气管炎、慢性阻塞性肺疾病（COPD）、银屑病、过敏性鼻炎、休克、特应性皮炎、克隆病、成人呼吸窘迫综合症（ARDS）、嗜酸性肉芽肿、过敏性结膜炎、骨关节炎、溃疡性结肠炎和其他炎症性疾病的患者，特别是人类。本发明还涉及所披露化合物的制备方法，以及其作为磷酸二酯酶（PDE）IV型抑制剂的药物组合物和用途。
• 6-phenyltetrahydro-1,3-oxazin-2-one derivative and pharmaceutical composition containing the same
  申请人：Nikken Chemicals Co., LTD

  公开号：US06251897B1

  公开（公告）日：2001-06-26

  A 6-phenyltetrahydro-1,3-oxazin-2-one derivative having the formula (I): wherein, R1 is an unsubstituted or substituted C1 to C8 alkyl group; an unsubstituted or substituted C3 to C7 cycloalkyl group;, etc., R2 is a C1 to C4 alkyl group, R3 is H; an unsubstituted or substituted C1 to C5 alkyl group; etc., R4 is H; an unsubstituted or substituted C1 to C6 alkyl group, and R5 and R6 are independently a hydrogen atom; an unsubstituted or substituted C1 to C5 alkyl group; etc. an optical isomer thereof, or a pharmacologically acceptable salt thereof, or a hydrate or a solvate thereof and pharmaceutical compositions containing the same, in particular a drug for the prevention or treatment of inflammatory diseases and a drug for asthma. The above 6-phenyltetrahydro-1,3-oxazin-2-one derivative has a strong type IV PDE inhibitory activity and has a bronchiodilator and antiinflammatory effects.

  具有以下式子（I）的6-苯基四氢-1,3-噁唑啉-2-酮衍生物：其中，R1是未取代或取代的C1到C8烷基；未取代或取代的C3到C7环烷基等；R2是C1到C4烷基，R3是H；未取代或取代的C1到C5烷基等；R4是H；未取代或取代的C1到C6烷基，R5和R6分别是氢原子；未取代或取代的C1到C5烷基等。其光学异构体，或其药理学上可接受的盐，或其水合物或溶剂化物和含有其的制药组合物，特别是用于预防或治疗炎症性疾病和哮喘的药物。上述6-苯基四氢-1,3-噁唑啉-2-酮衍生物具有强烈的IV型PDE抑制活性，并具有支气管扩张剂和抗炎作用。