3-amino-6,8,8-trimethyl-5,6,7,8-tetrahydro[1,6]naphthyridine | 252901-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-amino-6,8,8-trimethyl-5,6,7,8-tetrahydro[1,6]naphthyridine
• 英文别名: 3-amino-8,8-dimethyl-N-methyl[1,6]naphthyridine；3-Amino-5,6,7,8-tetrahydro-6,8,8-trimethyl[1,6]naphthyridine；6,8,8-trimethyl-5,7-dihydro-1,6-naphthyridin-3-amine
• CAS: 252901-48-7
• 化学式: C₁₁H₁₇N₃
• 分子量: 191.276
• InChiKey: STSSNAJAHISCHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氟-4-甲氧基苯甲酰氯 、 3-amino-6,8,8-trimethyl-5,6,7,8-tetrahydro[1,6]naphthyridine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(5,6,7,8-tetrahydro-6,8,8-trimethyl[1,6]naphthyridin-3-yl)-3-fluoro-4-methoxybenzamide
  参考文献：
  名称：

  The design of 8,8-Dimethyl[1,6]naphthyridines as potential anticonvulsant agents

  摘要：

  Starting from a series of 7-linked tetrahydroisoquinoline derivatives, as exemplified by SB-270664, a new series of 8,8-dimethylnaphthyridine compounds has been identified. SAR studies around these attractive leads have provided compounds such as 12 which display excellent anticonvulsant activity and an encouraging pharmacokinetic profile in vivo. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00288-9
• 作为产物：
  描述：

  1,3,3-三甲基-4-哌啶酮 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-amino-6,8,8-trimethyl-5,6,7,8-tetrahydro[1,6]naphthyridine
  参考文献：
  名称：

  3-氨基-5,6,7,8-四氢[1,6]萘啶体系和一些烷基化和多环同源物的简单合成

  摘要：

  3-氨基-5,6,7,8-四氢[1,6]萘啶系统 1 及其更多取代的同系物 2-5 通过单环和双环 4-哌啶酮 11a 的缩合的简易两步合成-c, 12-14 与 3,5-dinitro-1-methyl-2-pyridone 6 在氨存在下进行了描述。

  DOI：

  10.1081/scc-100103271

文献信息

• Tetrahydronaphthyridinyl-carboxamides having anti-convulsant activity
  申请人：SmithKline Beecham p.l.c.

  公开号：US06410555B1

  公开（公告）日：2002-06-25

  Compounds of formula (I) and pharmaceutically acceptable salts and solvates: where R1 is hydrogen, C1-6alkyl (optionally substituted by hydroxy or C1-4alkoxy), phenyl-C1-4alkyl-, C1-6alkenyl, C1-6alkynyl; R2 is hydrogen or, up to three substituents selected from halogen, NO2, CN, N3, CF3O—, CF3S—, CF3SO2—, CF3CO—, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C1-6perfluoroalkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl-, C1-6alkyl, C1-6alkylCO—, C3-6cycloalkylO—, C3-6cycloalkylCO—, C3-6cycloalkyl-C1-4alkylO—, C3-6cycloalkyl-C1-4alkylCO—, phenyl, phenoxy, benzyloxy, benzoyl, phenyl-C1-4alkyl-, C1-6alkylS—, C1-6alkylSO2—, (C1-4alkyl)2NSO2—, (C1-4alkyl)NHSO2—, (C1-4alkyl)2NCO—, (C1-4alkyl)NHCO— or CONH2; or —NR5R6 where R5 is hydrogen or C1-4alkyl, and R6 is hydrogen, C1-4alkyl, formyl, —CO2C1-4alkyl or —COC1-4alkyl; or two R2 groups together form a carbocyclic ring that is saturated or unsaturated, optionally interrupted by O or NH; R3 groups and R4 groups are each independently hydrogen or C1-6alkyl and/or the two R3 groups and/or the two R4 groups together form a C3-6spiroalkyl group, provided that at least one R3 or R4 group is not hydrogen; and X is selected from hydrogen, halogen, cyano, alkyl and alkoxy, are useful in the treatment and prophylaxis of epilepsy, migraine, and other disorders.

  式(I)的化合物及其药学上可接受的盐和溶剂：其中R1是氢、C1-6烷基（可选择地被羟基或C1-4烷氧基取代）、苯基-C1-4烷基、C1-6烯基、C1-6炔基；R2是氢或来自卤素、NO2、CN、N3、CF3O—、CF3S—、CF3SO2—、CF3CO—、C1-6烷基、C1-6烯基、C1-6炔基、C1-6全氟烷基、C3-6环烷基、C3-6环烷基-C1-4烷基、C1-6烷基、C1-6烷基CO—、C3-6环烷基O—、C3-6环烷基CO—、C3-6环烷基-C1-4烷基O—、C3-6环烷基-C1-4烷基CO—、苯基、苯氧基、苄氧基、苯甲酰基、苯基-C1-4烷基、C1-6烷基S—、C1-6烷基SO2—、（C1-4烷基）2NSO2—、（C1-4烷基）NHSO2—、（C1-4烷基）2NCO—、（C1-4烷基）NHCO—或CONH2中选择一个；或—NR5R6，其中R5是氢或C1-4烷基，R6是氢、C1-4烷基、甲酰基、—CO2C1-4烷基或—COC1-4烷基；或两个R2基一起形成一个饱和或不饱和的碳环，可选择地被O或NH打断；R3基团和R4基团各自独立地是氢或C1-6烷基和/或两个R3基团和/或两个R4基团一起形成一个C3-6螺环烷基，前提是至少一个R3或R4基团不是氢；X从氢、卤素、氰基、烷基和烷氧基中选择，对癫痫、偏头痛和其他疾病的治疗和预防有用。
• TETRAHYDRONAPHTHYRIDINYL-CARBOXAMIDES HAVING ANTI-CONVULSANT ACTIVITY
  申请人：SmithKline Beecham plc

  公开号：EP1084122B1

  公开（公告）日：2003-10-22
• US6410555B1
  申请人：——

  公开号：US6410555B1

  公开（公告）日：2002-06-25
• US6762192B2
  申请人：——

  公开号：US6762192B2

  公开（公告）日：2004-07-13
• [EN] TETRAHYDRONAPHTHYRIDINYL-CARBOXAMIDES HAVING ANTI-CONVULSANT ACTIVITY<br/>[FR] TETRAHYDRONAPHTYRIDINYL-CARBOXAMIDES PRESENTANT UNE ACTIVITE ANTI-CONVULSIVANTE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1999065903A1

  公开（公告）日：1999-12-23

  (EN) Compounds of formula (I) and pharmaceutically acceptable salts and solvates: where R1 is hydrogen, C1-6alkyl (optionally substituted by hydroxy or C1-4alkoxy), phenyl-C1-4alkyl-, C1-6alkenyl, C1-6alkynyl; R2 is hydrogen or up to three substituents selected from halogen, NO2, CN, N3, CF3O-, CF3S-, CF3SO2-, CF3CO-, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C1-6perfluoroalkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl-, C1-6alkylO-, C1-6alkylCO-, C3-6cycloalkylO-, C3-6cycloalkylCO-, C3-6cycloalkyl-C1-4alkylO-, C3-6cycloalkyl-C1-4alkylCO-, phenyl, phenoxy, benzyloxy, benzoyl, phenyl-C1-4alkyl-, C1-6alkylS-, C1-6alkylSO2-, (C1-4alkyl)2NSO2-, (C1-4alkyl)NHSO2-, (C1-4alkyl)2NCO-, (C1-4alkyl)NHCO- or CONH2; or -NR5R6 where R5 is hydrogen or C1-4alkyl, and R6 is hydrogen, C1-4alkyl, formyl, -CO2C1-4alkyl or -COC1-4alkyl; or two R2 groups together form a carbocyclic ring that is saturated or unsaturated, optionally interrupted by O or NH; R3 groups and R4 groups are each independently hydrogen or C1-6alkyl and/or the two R3 groups and/or the two R4 groups together form a C3-6spiroalkyl group, provided that at least one R3 or R4 group is not hydrogen; and X is selected from hydrogen, halogen, cyano, alkyl and alkoxy, are useful in the treatment and prophylaxis of epilepsy, migraine, and other disorders.(FR) La présente invention concerne des composés représentés par la formule générale (I) ainsi que certains de leurs sels et solvates pharmaceutiquement acceptés. Ces composés conviennent au traitement et à la prophylaxie de l'épilepsie, de la migraine et d'autres troubles. En l'occurrence, R1 est hydrogène, C1-6alkyle (éventuellement substitué par hydroxy ou C1-4alcoxy), phényle-C1-4alkyle-, C1-6alcényle, C1-6alkynyle; R2 est hydrogène ou un maximum de trois substituants choisis parmi halogène, NO2, CN, N3, CF3O-, CF3S-, CF3SO2-, CF3CO-, C1-6alkyle, C1-6alcényle, C1-6alkynyle, C1-6perfluoroalkyle, C3-6cycloalkyle, C3-6cycloalkyle-C1-4alkyle-, C1-6alkyleO-, C1-6alkyleCO-, C3-6cycloalkyleO-, C3-6cycloalkyleCO-, C3-6cycloalkyle-C1-4alkyleO-, C3-6cycloalkyle-C1-4alkyleCO-, phényle, phénoxy, benzyloxy, benzoyl, phényle-C1-4alkyle-, C1-6alkyleS-, C1-6alkyleSO2-, (C1-4alkyle)2NSO2-, (C1-4alkyle)NHSO2-, (C1-4alkyle)2NCO-, (C1-4alkyle)NHCO- ou CONH2; ou -NR5R6 auquel cas R5 est hydrogène ou C1-4alkyle, et R6 est hydrogène, C1-4alkyle, formyle, -CO2C1-4alkyle ou -COC1-4alkyle; ou deux groupes R2 forment ensemble un cycle carbocyclique qui est saturé ou insaturé, éventuellement interrompu par O ou NH; les groupes R3 et R4 sont chacun indépendamment hydrogène ou C1-6alkyle et/ou les deux groupes R3 et/ou les deux groupes R4 forment ensemble un groupe C3-6spiroalkyle, à condition que l'un au moins du groupe R3 ou R4 ne soit pas hydrogène; et X est hydrogène, halogène, cyano, alkyle ou alcoxy.