5-(3-methoxyphenyl)-3-methyl-1,2,4-oxadiazole | 1544566-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-methoxyphenyl)-3-methyl-1,2,4-oxadiazole
• 英文别名: 3-Methyl-5-(3-methoxyphenyl)-1,2,4-oxadiazole
• CAS: 1544566-21-3
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: RVFKZKQNJDQPBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-acetyl-3-methoxybenzamide 在 吡啶 、 盐酸羟胺 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以42%的产率得到5-(3-methoxyphenyl)-3-methyl-1,2,4-oxadiazole
  参考文献：
  名称：

  N-乙酰苯甲酰胺与盐酸羟胺的反应：3-甲基-5-芳基-1,2,4-恶二唑的合成

  摘要：

  描述了N-乙酰苯甲酰胺和盐酸羟胺在 80 °C 下在吡啶存在下在微波照射下的方便反应。该方法以中等至良好的收率形成区域选择性的 3-甲基-5-芳基-1,2,4-恶二唑化合物，并且还采用简单的合成方案，无需冗长的纯化程序。该反应还通过常规加热和微波照射下的一锅顺序进行。合成化合物的结构通过光谱方法进行了确认。 图形概要

  DOI：

  10.1007/s00706-022-02975-z

文献信息

• Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: a highly efficient and fluoride-free ring closure reaction of O-acylamidoximes
  作者：Hiromichi Otaka、Junya Ikeda、Daisuke Tanaka、Masanori Tobe

  DOI：10.1016/j.tetlet.2013.12.016

  日期：2014.1

  Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range

  氢氧化四丁基铵（TBAH）是氟化四丁基铵（TBAF）的一种高效，温和的替代品，用于由O-酰基酰胺基肟对1,2,4-恶二唑进行碱催化的环化反应。对于大多数3,5-取代的1,2,4-恶二唑，在室温下通过添加0.1当量的TBAH可以显着加速反应。该方法也更普遍地适用于允许更大范围的基板。另外，由于不存在氟化物，TBAH不会导致反应堆容器的腐蚀，因此更适合大规模合成。
• 4-Substituted-1,5-Dihydro-Pyrido[3,2-B]Indol-2-Ones
  申请人：Kesteleyn Rudolf Romanie Bart

  公开号：US20070249655A1

  公开（公告）日：2007-10-25

  The present invention concerns combinations comprising a compound of formula (I) the N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters or metabolites thereof, wherein n is 1, 2 or 3; R 1 is H, CN, halo, aminoC(═O), C(═O)OH, C 1-4 alkyloxyC(═O), C 1-4 alkylC(═O), mono- or di(C 1-4 alkyl)aminoC(═O), arylaminoC(═O), N-(aryl)-N-(C 1-4 alkyl)aminoC(═O), methanimidamidyl, N-hydroxy-methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, Het 1 or Het 2 ; R 2 is H, C 1-4 alkyl, C 2-10 alkenyl, C 3-7 cycloalkyl, wherein said C 1-10 alkyl, C 2-10 alkenyl and C 3-7 cycloalkyl may be optionally substituted; R 3 is nitro, cyano, amino, halo, hydroxy, C 1-4 alkyloxy, hydroxyC(═O), aminoC(═O), C 1-4 alkyloxyC(═O), mono- or di(C 1-4 alkyl)aminoC(═O), C 1-4 alkylC(═O), methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, N-hydroxy-methanimidamidyl or Het 1 ; and another HIV inhibitor. The invention also concerns products comprising a compound of formula (I) and another HIV inhibitor, as a combined preparation for simultaneous, separate or sequential use in treatment of retroviral infections such as HIV infection, in particular, in the treatment of infections with multi-drug resistant retroviruses.

  本发明涉及一种组合物，包括式（I）化合物的N-氧化物、盐、立体异构体形式、混合物、前药、酯或其代谢物，其中n为1、2或3；R1为H、CN、卤素、氨基C（═O）、C（═O）OH、C1-4烷氧基C（═O）、C1-4烷基C（═O）、单烷基或二烷基氨基C（═O）、芳基氨基C（═O）、N-(芳基)-N-(C1-4烷基)氨基C（═O）、甲基亚胺基、N-羟基甲基亚胺基、单烷基或二烷基甲基亚胺基、Het1或Het2；R2为H、C1-4烷基、C2-10烯基、C3-7环烷基，其中所述的C1-10烷基、C2-10烯基和C3-7环烷基可以选择性地被取代；R3为硝基、氰基、氨基、卤素、羟基、C1-4烷氧基、羟基C（═O）、氨基C（═O）、C1-4烷氧基C（═O）、单烷基或二烷基氨基C（═O）、C1-4烷基C（═O）、甲基亚胺基、单烷基或二烷基甲基亚胺基、N-羟基甲基亚胺基或Het1；以及另一种HIV抑制剂。本发明还涉及包含式（I）化合物和另一种HIV抑制剂的产品，作为联合制剂，用于同时、分离或顺序治疗逆转录病毒感染，例如HIV感染，特别是治疗多药耐药逆转录病毒感染。
• Phosphodiesterase Inhibitors
  申请人：Palle P. Venkata

  公开号：US20070259874A1

  公开（公告）日：2007-11-08

  The present invention relates to isoxazoline derivatives and their analogues, which can be used as phosphodiesterase (PDE) type IV selective inhibitors. 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, especially in humans. Processes for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds, and their use as PDE type IV selective inhibitors, are provided.

  本发明涉及异噁唑啉衍生物及其类似物，可用作磷酸二酯酶（PDE）IV型选择性抑制剂。本文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、克罗恩病、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，尤其是在人类中。本文提供了所披露的化合物的制备方法、含有所披露的化合物的药物组合物以及它们作为PDE IV型选择性抑制剂的用途。
• SUBSTITUTED INDOLEPYRIDINIUM AS ANTI-INFECTIVE COMPOUNDS
  申请人：KESTELEYN Bart Rudolf Romanie

  公开号：US20100048563A1

  公开（公告）日：2010-02-25

  The present invention concerns the compounds of formula (I) their N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites, wherein n is 1, 2 or 3; R 1 is H, CN, halo, aminoC(═O), C(═O)OH, C 1-4 alkyloxyC(═O), C 1-4 alkylC(═O), mono- or di(C 1-4 alkyl)aminoC(═O), arylaminoC(═O), N-(aryl)-N—(C 1-4 alkyl)aminoC(═O), methanimidamidyl, N-hydroxy-methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, Het 1 or Het 2 ; R 2 is H, C 1-10 alkyl, C 2-10 alkenyl, C 3-7 cycloalkyl, wherein said C 1-10 alkyl, C 2-10 alkenyl and C 3-7 cycloalkyl may be optionally substituted; R 3 is nitro, cyano, amino, halo, hydroxy, C 1-4 alkyloxy, hydroxyC(═O), aminoC(═O), C 1-4 alkyloxyC(═O), mono- or di(C 1-4 alkyl)aminoC(═O), C 1-4 alkylC(═O), methanimidamidyl, mono- or di(C 1-4 alkyl)methanimidamidyl, N-hydroxy-methanimidamidyl or Het 1 ; for use as a medicine. The invention further relates to a novel subgroup of the compounds of formula (I), and to compositions comprising compounds of formula (I).

  本发明涉及式(I)化合物及其N-氧化物、盐、立体异构体、外消旋混合物、前药、酯和代谢物，其中n为1、2或3；R1为H、CN、卤素、氨基C(═O)、C(═O)OH、C1-4烷氧基C(═O)、C1-4烷基C(═O)、单取代或双取代(C1-4烷基)氨基C(═O)、芳基氨基C(═O)、N-(芳基)-N-(C1-4烷基)氨基C(═O)、甲基亚胺基、N-羟基甲基亚胺基、单取代或双取代(C1-4烷基)甲基亚胺基、Het1或Het2；R2为H、C1-10烷基、C2-10烯基、C3-7环烷基，其中所述的C1-10烷基、C2-10烯基和C3-7环烷基可以选择性地被取代；R3为硝基、氰基、氨基、卤素、羟基、C1-4烷氧基、羟基C(═O)、氨基C(═O)、C1-4烷氧基C(═O)、单取代或双取代(C1-4烷基)氨基C(═O)、C1-4烷基C(═O)、甲基亚胺基、单取代或双取代(C1-4烷基)甲基亚胺基、N-羟基甲基亚胺基或Het1；用作药物。本发明还涉及式(I)化合物的新亚组，以及包含式(I)化合物的组合物。
• ISOXAZOLINES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Behnke Mark L.

  公开号：US20110028478A1

  公开（公告）日：2011-02-03

  The present invention provides isoxazoline FAAH inhibitors of the formula (I): or pharmaceutically acceptable forms thereof, wherein each of G, R a , R b , R c , and R d are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable form thereof, and a pharmaceutically acceptable excipient. The present invention also provides methods for treating an FAAH-mediated condition comprising administering a therapeutically effective amount of a compound of formula (I), or pharmaceutically acceptable form thereof, to a subject in need thereof.

  本发明提供了式(I)的异噁唑烷FAAH抑制剂或其药学上可接受的形式，其中G、Ra、Rb、Rc和Rd的定义如本文所述。本发明还提供了包括式(I)化合物或其药学上可接受的形式和药学上可接受的赋形剂的制药组合物。本发明还提供了治疗FAAH介导的疾病的方法，包括向需要治疗的患者施用式(I)化合物或其药学上可接受的形式的治疗有效量。