6-bromonicotine | 185510-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-bromonicotine
• 英文别名: (S)-6-Bromonicotine；2-Bromo-5-(1-methylpyrrolidin-2-yl)pyridine
• CAS: 185510-36-5
• 化学式: C₁₀H₁₃BrN₂
• 分子量: 241.131
• InChiKey: QKSAQBUVZWITMX-UHFFFAOYSA-N

物化性质

• 沸点：
  295.4±40.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromonicotine 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 3-(1-methyl-2-pyrrolidinyl)pyridine-6-carboxylic acid
  参考文献：
  名称：

  Synthesis, receptor binding and QSAR studies on 6-substituted nicotine derivatives as cholinergic ligands

  摘要：

  DOI：

  10.1016/s0223-5234(99)80038-5
• 作为产物：
  描述：

  5-(1-甲基-2-吡咯烷基)-2-氨基吡啶 在 氢溴酸 、 溴 、 sodium nitrite 作用下， 以 水 为溶剂， 以22%的产率得到6-bromonicotine
  参考文献：
  名称：

  Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation

  摘要：

  Because the structural requirements for the binding of nicotine to central nicotine receptors remain largely uninvestigated, we undertook a systematic investigation of pyrrolidine ring-opened analogs. This led to a subsequent investigation of related conformationally restricted derivatives of these analogs. The results are reported relative to the binding of several well-known and widely used nicotine receptor ligands. Although none of the ring-opened analogs binds with higher affinity than (-)nicotine (K-i = 2.3 nM), 3-(N-methyl-N-ethylaminomethyl)pyridine (12a; K-i = 28 nM) binds with significant affinity. A conformationally restricted analog of 12a, N-methyl [2,7]naphthyridine 30b (K-i = 18 nM), binds with similar affinity. 6-Substitution of 12a and racemic nicotine seems to be tolerated when the substituent is halogen or methyl. In functional studies (hypolocomotion and antinociception in mice; stimulus generalization in nicotine-trained rats) 30b retains nicotine-like properties. Several of the 6-substituted compounds were 2 to 20 times more potent than (+/-)nicotine. Although the intact pyrrolidine ring of nicotine appears important for optimal affinity, its pre presence is not an absolute requirement for activity, and 6-position substitution of the pyridine nucleus can influence both binding and functional activity.

  DOI：

  10.1016/s0223-5234(97)89850-9

文献信息

• Nicotine immunogen
  申请人：Independent Pharmaceutica AB

  公开号：US06656469B1

  公开（公告）日：2003-12-02

  A 5- or 6-nicotinyl-linker-carrier protein compound and immunogen having formula (a) wherein X is —NH—CO— or NH— or —C≡C— or —C═C— or CH2—; Y is —(CH2)k— or —(CH2)m—C6H10—(CH2)n— or (CH2)m—C6H4—(CH2)n— when Z is —NH—, with the proviso that X is not —NH—CO— when Y is (CH2)5 and Z is —NH—, and X is —NH—CO— or —C≡C— or —C═C— or CH2—, Y is —(CH2)m—C6H10—(CH2)n— or —(CH2)m—C6H4—(CH2)n—, when Z is —CO—, and X is —C≡C— or —C═C—, Z is —CO—, when Y is (CH2)k—, is disclosed. The compound may be used as a medicament, suitably in the form of a pharmaceutical composition. Additionally, a method of prophylactic and/or therapeutic immunological treatment of nicotine dependence from tobacco products to achieve harm reduction is described.

  一种具有以下结构式(a)的5-或6-烟碱基-连接蛋白质化合物和免疫原，其中X为—NH—CO—或NH—或—C≡C—或—C═C—或CH2—；Y为—(CH2)k—或—(CH2)m—C6H10—(CH2)n—或(CH2)m—C6H4—(CH2)n—，当Z为—NH—时，但X不为—NH—CO—时，Y为(CH2)5且Z为—NH—；当Z为—CO—时，X为—NH—CO—或—C≡C—或—C═C—或CH2—，Y为—(CH2)m—C6H10—(CH2)n—或—(CH2)m—C6H4—(CH2)n—；当Z为—CO—时，X为—C≡C—或—C═C—，Z为—CO—，Y为(CH2)k—。该化合物可用作药物，适宜以药物组合物的形式使用。此外，还描述了一种用于预防性和/或治疗性免疫治疗尼古丁依赖性的方法，以实现烟草制品对健康的减害作用。
• Hapten-carrier conjugates and uses thereof
  申请人：Bachmann F. Martin

  公开号：US20050281845A1

  公开（公告）日：2005-12-22

  The present invention provides compositions comprising a conjugate of a hapten with a carrier in an ordered and repetitive array, and methods of making such compositions. The conjugates and compositions of the invention may comprise a variety of haptens, including hormones, toxins and drugs, especially drugs of addiction such as nicotine. Compositions and conjugates of the invention are useful for inducing immune responses against haptens, which can use useful in a variety of therapeutic, prophylactic and diagnostic regimens. In certain embodiments, immune responses generated using the conjugates, compositions and methods of the present invention are useful to prevent or treat addiction to drugs of abuse and the resultant diseases associated with drug addiction.

  本发明提供了一种包含半抗原与载体的共轭物的组合物，其具有有序和重复的排列方式，并提供了制备这种组合物的方法。本发明的共轭物和组合物可以包含各种半抗原，包括激素、毒素和药物，特别是成瘾药物如尼古丁。本发明的组合物和共轭物可用于诱导免疫反应，用于各种治疗、预防和诊断方案。在某些实施例中，使用本发明的共轭物、组合物和方法产生的免疫反应可用于预防或治疗药物成瘾及与药物成瘾相关的疾病。
• Nitrogen substituted 1,2,4-triazolo[3,4-a]phthalazine derivatives for enhancing cognition
  申请人：——

  公开号：US20040043982A1

  公开（公告）日：2004-03-04

  The present invention provides a compound of formula (I) wherein A is an optionally substituted C1-4alkylidene group or a bond, R20 and R21 are hydrogen, alkyl groups or heterocyclic groups, R1 and R2 are small substituents or hydrogen, L is O, S or substituted N, X is a 5-or 6-membered heteroaromatic ring, Y is C1-4alkylidene and Z is a 5- or 6-membered heteroaromatic ring; or a pharmaceutically acceptable salt thereof; pharmaceutical compositions comprising it; its use in therapy; its use in making medicaments for treating neurodegenerative disease and methods of using it to enhance cognition.

  本发明提供了化合物(I)的结构式，其中A是可选取代的C1-4烷基亚甲基或键合，R20和R21是氢、烷基或杂环基，R1和R2是小的取代基或氢，L是O、S或取代的N，X是5-或6-成员杂芳基环，Y是C1-4烷基亚甲基，Z是5-或6-成员杂芳基环；或其药学上可接受的盐；包括它的制药组合物；其在治疗中的用途；其用于制造治疗神经退行性疾病的药物和使用它以增强认知能力的方法。
• Hapten-Carrier Conjugates and Uses Thereof
  申请人：BACHMANN Martin F.

  公开号：US20130142821A1

  公开（公告）日：2013-06-06

  The present invention provides compositions comprising a conjugate of a hapten with a carrier in an ordered and repetitive array, and methods of making such compositions. The conjugates and compositions of the invention may comprise a variety of haptens, including hormones, toxins and drugs, especially drugs of addiction such as nicotine. Compositions and conjugates of the invention are useful for inducing immune responses against haptens, which can use useful in a variety of therapeutic, prophylactic and diagnostic regimens. In certain embodiments, immune responses generated using the conjugates, compositions and methods of the present invention are useful to prevent or treat addiction to drugs of abuse and the resultant diseases associated with drug addiction.

  本发明提供了一种由载体和半抗原共价结合的有序和重复阵列的组合物及其制备方法。该发明的共价结合物和组合物可以包含多种半抗原，包括激素、毒素和药物，特别是成瘾药物如尼古丁。本发明的组合物和共价结合物可用于诱导对半抗原的免疫反应，这对于各种治疗、预防和诊断方案都有用。在某些实施例中，使用本发明的共价结合物、组合物和方法产生的免疫反应可用于预防或治疗药物成瘾及与药物成瘾相关的疾病。
• Hapten-carrier conjugates comprising virus like particles and uses thereof
  申请人：Cytos Biotechnology AG

  公开号：EP2392345A2

  公开（公告）日：2011-12-07

  The present invention provides compositions comprising a conjugate of a hapten with a carrier in an ordered and repetitive array, and methods of making such compositions. The conjugates and compositions of the invention comprise drugs, especially drugs of addiction such as nicotine. Compositions and conjugates of the invention are useful for inducing immune responses against haptens, which can use useful in a variety of therapeutic, prophylactic and diagnostic regimens. In certain embodiments, immune responses generated using the conjugates, compositions and methods of the present invention are useful to prevent or treat addiction to drugs of abuse and the resultant diseases associated with drug addiction.

  本发明提供了包含以有序和重复阵列形式存在的合体与载体的共轭物的组合物，以及制造这种组合物的方法。本发明的共轭物和组合物包含药物，特别是成瘾药物，如尼古丁。本发明的组合物和共轭物可用于诱导针对合体的免疫反应，这可用于各种治疗、预防和诊断方案。在某些实施方案中，使用本发明的共轭物、组合物和方法产生的免疫反应可用于预防或治疗对滥用药物的成瘾以及由此导致的与药物成瘾相关的疾病。