4-(1-Benzylpiperidin-4-yl)oxyaniline | 565418-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(1-Benzylpiperidin-4-yl)oxyaniline
• CAS: 565418-42-0
• 化学式: C₁₈H₂₂N₂O
• 分子量: 282.385
• InChiKey: PWMGGDQMZHIGDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-Benzylpiperidin-4-yl)oxyaniline 、 2,4,6-三氟苯甲醛 在 三乙酰氧基硼氢化钠 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 4-(1-benzylpiperidin-4-yl)oxy-N-[(2,4,6-trifluorophenyl)methyl]aniline
  参考文献：
  名称：

  Substituted aniline derivatives useful as histamine H3 antagonists

  摘要：

  揭示了以下化合物的结构式或其药学上可接受的盐，其中M1为M2为N；X为键合，可选择地取代的烷基，烯基，—O—，—CH2N(R12)—，—N(R12)CH2—，—N(R12)—，—NHC(O)—，—OCH2—，—CH2O—或—S(O)0-2—；Y为—(CH2)1-2—，—C(═O)—，—C(═NOR13)—或—SO0-2—；或者M1为N；M2为N或CH；X为键合，烷基，烯基，—C(O)—，—NHC(O)—，—OC(O)—或—S(O)1-2—；Y为—(CH2)1-2—，—C(═O)—或—SO0-2—；当M2为CH时，Y也为—O—或—C(═NOR13)—；Z为键合或可选择地取代的烷基或烯基；U和W为CH，或其中一个为CH，另一个为N；R1为可选择地取代的烷基，环烷基，芳基，芳基烷基，杂环芳基，杂环烷基；R2为可选择地取代的烷基，烯基，芳基，芳基烷基，杂环芳基，杂环芳基烷基，环烷基或杂环烷基；其余变量如规范中定义；以及治疗肥胖症、代谢综合征和认知缺陷障碍的组合物和方法，可单独使用或与其他药物组合使用。

  公开号：

  US20070142394A1
• 作为产物：
  描述：

  1-苄基-4-(4-硝基苯氧基)哌啶 在 Raney nickel 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 生成 4-(1-Benzylpiperidin-4-yl)oxyaniline
  参考文献：
  名称：

  Substituted aniline derivatives useful as histamine H3 antagonists

  摘要：

  揭示了以下化合物的结构式或其药学上可接受的盐，其中M1为M2为N；X为键合，可选择地取代的烷基，烯基，—O—，—CH2N(R12)—，—N(R12)CH2—，—N(R12)—，—NHC(O)—，—OCH2—，—CH2O—或—S(O)0-2—；Y为—(CH2)1-2—，—C(═O)—，—C(═NOR13)—或—SO0-2—；或者M1为N；M2为N或CH；X为键合，烷基，烯基，—C(O)—，—NHC(O)—，—OC(O)—或—S(O)1-2—；Y为—(CH2)1-2—，—C(═O)—或—SO0-2—；当M2为CH时，Y也为—O—或—C(═NOR13)—；Z为键合或可选择地取代的烷基或烯基；U和W为CH，或其中一个为CH，另一个为N；R1为可选择地取代的烷基，环烷基，芳基，芳基烷基，杂环芳基，杂环烷基；R2为可选择地取代的烷基，烯基，芳基，芳基烷基，杂环芳基，杂环芳基烷基，环烷基或杂环烷基；其余变量如规范中定义；以及治疗肥胖症、代谢综合征和认知缺陷障碍的组合物和方法，可单独使用或与其他药物组合使用。

  公开号：

  US20070142394A1

文献信息

• Phenoxypiperidines and analogs thereof useful as histamine H3 antagonists
  申请人：Mutahi W. Mwangi

  公开号：US20070167435A1

  公开（公告）日：2007-07-19

  Disclosed are compounds of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein: M is CH or N; U and W are each CH, or one of U and W is CH and the other is N; X is a bond, alkylene, —C(O)—, —C(N—OR 5 )—, —C(N—OR 5 )—CH(R 6 )—, —CH(R 6 )—C(N—OR 5 )—, —O—, —OCH 2 —, —CH 2 O— or —S(O) 0-2 —; Y is —O—, —(CH 2 ) 2 —, —C(═O)—, —C(═NOR 7 )— or —SO 0-2 —; Z is a bond, optionally substituted alkylene or alkylene interrupted by a heteroatom or heterocyclic group; R 1 is optionally substituted alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, heterocycloalkyl, or benzimidazolyl or a derivative thereof; R 2 is optionally substituted alkyl, alkenyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl or heterocycloalkyl; and the remaining variables are as defined in the specification; compositions and methods for treating an allergy-induced airway response, congestion, diabetes, obesity, an obesity-related disorder, metabolic syndrome and a cognition deficit disorder using said compounds, alone or in combination with other agents.

  揭示了以下化合物的结构式或其药学上可接受的盐或溶剂，其中：M为CH或N；U和W分别为CH，或者U和W中的一个为CH，另一个为N；X为键，烷基，—C(O)—，—C(N—OR5)—，—C(N—OR5)—CH(R6)—，—CH(R6)—C(N—OR5)—，—O—，—OCH2—，—CH2O—或—S(O)0-2—；Y为—O—，—(CH2)2—，—C(═O)—，—C(═NOR7)—或—SO0-2—；Z为键，可选择地取代的烷基或被杂原子或杂环基中断的烷基；R1为可选择地取代的烷基，环烷基，芳基，芳基烷基，杂芳基，杂环烷基或苯并咪唑基或其衍生物；R2为可选择地取代的烷基，烯基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基或杂环烷基；其余变量如规范中所定义；使用这些化合物，单独或与其他药剂联合使用，治疗由过敏引起的气道反应、充血、糖尿病、肥胖症、与肥胖有关的疾病、代谢综合征和认知缺陷障碍的组合物和方法。
• AZACYCLIC COMPOUNDS AS INHIBITORS OF SENSORY NEURONE SPECIFIC SODIUM CHANNELS
  申请人：Hamlyn Richard

  公开号：US20100204224A1

  公开（公告）日：2010-08-12

  Compounds of the formula (I), and pharmaceutically acceptable salts thereof, are found to be antagonists of SNS sodium channels. They are therefore useful as analgesic and neuroprotective agents; wherein (1) represents (A), (B) or (C); R 1 represents: (a) -L-A or L′-A′ wherein L represents a bond or a C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl moiety, A represents a phenyl, 5- to 10-membered heteroaryl, C 3 -C 6 carbocyclyl or 5- to 10 membered heterocyclyl group, L′ represents a C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl moiety, and A′ represents -Het-A or —X-A wherein Het represents —O—, —S— or NR′, and X represents —CO—, —SO—, SO 2 —, —CO—O—, CO—S, CONR′, —O—CO—, —S—CO— or NR′—CO—, wherein R′ represents hydrogen or C 1 -C 6 alkyl; (b) -L-A-A′ or -L-A-L-A wherein A′ is as defined above, each A is the same or different and is as defined above and each L is the same or different and is as defined above; (c) -A-Z-A wherein Z is -Het-L′, —X-L′, -L′-Het- or L′-X, wherein Het, L′ and X are as defined above and each A is the same or different and is as defined above; (d) -A-Het-Y or -A-X—Y wherein is [L′-Het] n -L′, [L′-Het] n -L′, -[L′-Het] n -A, -L′-B-L′, -L′-B-A or -A-L-A wherein n is from 1 to 4 and B is —X—, —NR′—CO—NR′, —O—CO—NR′— or —NR′—CO—O, and wherein X and L are as defined above, each A is the same or different and is as defined above, each L′ is the same or different and is as defined above, each R′ is the same or different and is as defined above and each Het is the same or different and is as defined above; or (e) -L-CR(A)(A′) or L-CR(A)(L-A) wherein R is hydrogen or C 1 -C 4 alkyl, A′ is as defined above, each L is the same or different and is as defined above and each A is the same or different and is as defined above; R 2 represents -L-A-, L′-A′, -L-A-A′ or L-A-L-A wherein L′ and A′ are as defined above, each L is the same or different and is as defined above and each A is the same or different and is as defined above J represents —NR 3 —, —O— or a direct bond wherein R 3 represent s hydrogen C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl; p is an integer from 1 to 3; q is 1 or 2; and one of E and E′ is —CH 2 — and the other is a direct bond.

  式(I)的化合物及其药学上可接受的盐被发现是SNS钠通道的拮抗剂。它们因此可作为镇痛和神经保护剂使用；其中(1)代表(A)、(B)或(C)；R1代表：(a) -L-A或L'-A'，其中L代表一个键或一个C1-C6烷基，C2-C6烯基或C2-C6炔基基团，A代表一个苯基，5-至10-成员杂芳基，C3-C6环烷基或5-至10-成员杂环基团，L'代表一个C1-C6烷基，C2-C6烯基或C2-C6炔基基团，A'代表-Het-A或-X-A，其中Het代表-O-、-S-或NR'，X代表-CO-、-SO-、SO2-、-CO-O-、CO-S、CONR'、-O-CO-、-S-CO-或NR'-CO-，其中R'代表氢或C1-C6烷基；(b) -L-A-A'或-L-A-L-A，其中A'如上所定义，每个A相同或不同，如上所定义，每个L相同或不同，如上所定义；(c) -A-Z-A，其中Z为-Het-L'、-X-L'、-L'-Het-或L'-X，其中Het、L'和X如上所定义，每个A相同或不同，如上所定义；(d) -A-Het-Y或-A-X-Y，其中是[L'-Het]n-L'、[L'-Het]n-L'、-[L'-Het]n-A、-L'-B-L'、-L'-B-A或-A-L-A，其中n为1至4，B为-X-、-NR'-CO-NR'-、-O-CO-NR'-或-NR'-CO-O，其中X和L如上所定义，每个A相同或不同，如上所定义，每个L'相同或不同，如上所定义，每个R'相同或不同，如上所定义，每个Het相同或不同，如上所定义；或(e) -L-CR(A)(A')或L-CR(A)(L-A)，其中R为氢或C1-C4烷基，A'如上所定义，每个L相同或不同，如上所定义，每个A相同或不同，如上所定义；R2代表-L-A-、L'-A'、-L-A-A'或L-A-L-A，其中L'和A'如上所定义，每个L相同或不同，如上所定义，每个A相同或不同，如上所定义；J代表-NR3-、-O-或直接键，其中R3代表氢、C1-C6烷基、C2-C6烯基或C2-C6炔基；p为1至3的整数；q为1或2；E和E'中的一个为-CH2-，另一个为直接键。
• Phenoxy piperidines for treating diseases such as schizophrenia and depression
  申请人：Holzemann Gunter

  公开号：US20050131021A1

  公开（公告）日：2005-06-16

  Compounds of the formula (1), in which R 1 , R 2 ′, R 2 ″, R 2 ′″, R 3 and n are as defined in claim 1, are effectors of the nicotinic and/or muscarinic acetylcholine receprot and are suitable for the prophylaxis or treatment of schizophrenia, depression, anxiety states, dementia, Alzheimer's disease, Lewy bodies dementia, neurodegenerative diseases, Parkinson's disease, Huntington's disease, Tourette's syndrome, learning and memory impairments, age-related memory impairment, amelioration of withdrawal symptoms in nicotine dependence, strokes or brain damage by toxic compounds.

  式（1）化合物，其中 R 1 , R 2 ′, R 2 ″, R 2 ′″, R 3 和 n 如权利要求 1 中所定义，是烟碱和/或毒蕈碱乙酰胆碱受体的效应物，适用于预防或治疗精神分裂症、抑郁症、焦虑症、痴呆症、阿尔茨海默病、路易体痴呆症、神经退行性疾病、帕金森病、亨廷顿病、抽动秽语综合征、学习和记忆障碍、与年龄有关的记忆损伤、学习和记忆力减退、神经退行性疾病、帕金森病、亨廷顿病、抽动秽语综合征、学习和记忆障碍、与年龄相关的记忆障碍、改善尼古丁依赖的戒断症状、中风或有毒化合物对大脑的损害。
• PHENOXY-PIPERIDINE ZUR BEHANDLUNG VON ERKRANKUNGEN WIE SCHIZOPHRENIE UND DEPRESSION
  申请人：MERCK PATENT GmbH

  公开号：EP1465868A1

  公开（公告）日：2004-10-13
• PHENOXY-PIPERIDINES FOR THE TREATMENT OF DISEASES SUCH AS SCHIZOPHRENIA AND DEPRESSION
  申请人：HOLZEMANN Gunter

  公开号：US20090247584A1

  公开（公告）日：2009-10-01

  Compounds of the formula (I), in which R 1 , R 2′ , R 2″ , R 2′″ , R 3 and n are as defined in Claim 1 , are effectors of the nicotinic and/or muscarinic acetylcholine receptor and are suitable for the prophylaxis or treatment of schizophrenia, depression, anxiety states, dementia, Alzheimer's disease, Lewy bodies dementia, neurodegenerative diseases, Parkinson's disease, Huntington's disease, Tourette's syndrome, learning and memory impairments, age-related memory impairment, amelioration of withdrawal symptoms in nicotine dependence, strokes or brain damage by toxic compounds.