2-甲氧基-6-甲基吡啶-5-甲腈 | 105277-11-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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
• 中文名称: 2-甲氧基-6-甲基吡啶-5-甲腈
• 中文别名: 6-甲氧基-2-甲基吡啶-3-甲腈
• 英文名称: 2-methoxy-6-methylpyridine-5-carbonitrile
• 英文别名: 6-methoxy-2-methyl-3-pyridinecarbonitrile；6-methoxy-2-methylpyridine-3-carbonitrile；3-cyano-6-methoxy-2-methylpyridine；6-methoxy-2-methylnicotinonitrile
• CAS: 105277-11-0
• 化学式: C₈H₈N₂O
• 分子量: 148.164
• InChiKey: ZDVDVDYVVWUZAP-UHFFFAOYSA-N

物化性质

• 沸点：
  254.8±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 储存条件：
  存储条件：室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  2-甲氧基-6-甲基吡啶-5-甲腈 在 selenium(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三乙胺 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 41.5h， 生成 5,6-dihydro-2,3,9-trimethoxy-5,11-dioxo-10-aza-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  AZAINDENOISOQUINOLINE TOPOISOMERASE I INHIBITORS

  摘要：

  本发明涉及替代的氮杂吲哚异异喹啉化合物，特别是7-、8-、9- 和10-氮杂吲哚异异喹啉化合物，它们是拓扑异构酶I的抑制剂，以及用于合成它们的过程和中间体，这些化合物的药物组合物，以及在癌症治疗中使用它们的方法。

  公开号：

  US20140018360A1
• 作为产物：
  描述：

  6-氯-2-甲基-3-氰基吡啶 生成 2-甲氧基-6-甲基吡啶-5-甲腈
  参考文献：
  名称：

  摘要：

  DOI：
• 作为试剂：
  描述：

  sodium methylate 、 6-氯-2-甲基-3-氰基吡啶 在 二氯甲烷 、 2-甲氧基-6-甲基吡啶-5-甲腈 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以This resulted in 1.80 g (93%) of 6-methoxy-2-methylpyridine-3-carbonitrile as a yellow solid的产率得到2-甲氧基-6-甲基吡啶-5-甲腈
  参考文献：
  名称：

  PYRAZOLOPYRIDINE PYRAZOLOPYRIMIDINE AND RELATED COMPOUNDS

  摘要：

  在某个方面，本发明通常涉及以下式的化合物及其亚式，或者每个亚式的互变异构体，每个互变异构体的药学上可接受的盐，或者每个上述物质的药学上可接受的溶剂，其中X1，L1，L3和R3在此被描述。

  公开号：

  US20150315198A1

文献信息

• [EN] 2-CYANOISOINDOLINE DERIVATIVES FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 2-CYANOISOINDOLINE POUR LE TRAITEMENT DU CANCER
  申请人：MISSION THERAPEUTICS LTD

  公开号：WO2017158388A1

  公开（公告）日：2017-09-21

  The invention relates to novel compounds of formula I which are inhibitors of deubiquitylating enzymes (DUBs) and/or desumoylating enzymes. In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase 7 or ubiquitin specific peptidase 7 (USP7). The invention further relates to methods for the preparation of these compounds and to their use in the treatment of cancer.

  这项发明涉及公式I的新化合物，这些化合物是去泛素化酶（DUBs）和/或去泛素化酶的抑制剂。具体来说，该发明涉及抑制泛素C端水解酶7或泛素特异性肽酶7（USP7）。该发明还涉及这些化合物的制备方法以及它们在癌症治疗中的应用。
• [EN] BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS<br/>[FR] COMPOSÉS BICYCLIQUES SUBSTITUÉS PAR HÉTÉROARYLE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018013774A1

  公开（公告）日：2018-01-18

  Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

  公开了公式(I)至(VIII)的化合物：(I) (II) (III) (IV) (V) (VI) (VII) (VIII)；或其立体异构体、互变异构体、药物可接受的盐、溶剂化物或前药，其中R3是与0至3个R3a取代的双环杂芳基团；且R1、R2、R3a、R4和n在此定义。还公开了使用这些化合物作为PAR4抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物用于抑制或预防血小板聚集，用于治疗血栓栓塞障碍或作为血栓栓塞障碍的初级预防。
• 1,2,4-oxadiazole derivatives and their therapeutic use
  申请人：Laboratorios Almirall, S.A.

  公开号：EP2202232A1

  公开（公告）日：2010-06-30

  New derivatives of general formula (I), or pharmaceutically acceptable salts or N-oxides thereof wherein, A is selected from the group consisting of -N-, -O- and -S-; B and C are independently selected from the group consisting of-N- and -O-, with the proviso that at least two of A, B and C are nitrogen atoms; G1 is selected from the group consisting of -CH2-, -NH- and -O-; G2 is selected from the group consisting of -NR4- and -O-; R1 represents: ➢ a 8 to 10 membered bicyclic N-containing heteroaryl group optionally substituted with a C1-4 carboxyalkyl group or a C1-4 aminoalkyl group, ➢ a pyridyl group optionally substituted with one or more substituents selected from hydroxy groups, C1-4 alkyl groups, C1-4 carboxyalkyl groups, C1-4 haloalkyl groups, C1-4 alkoxy groups, amino groups, C1-4 aminoalkyl groups and C1-4 aminoalkoxy groups, ➢ a pyridone group substituted with one or more C1-4 alkyl groups; C1-4 haloalkyl groups or C1-4 aminoalkyl groups, or ➢ a group of formula: wherein: • Ra represents a hydrogen atom, a halogen atom, a C1-4 alkyl group, C3-4 cycloalkyl group or a -CF3 group; • Rb represents a hydrogen atom, a halogen atom, a C14 alkyl group, a -CF3 group or a C1-4 alkoxy group; • Rd represents a hydrogen atom, a C1-4 alkyl group or a C1-4 alkoxy group; • Rc represents: ○ a hydrogen atom, a C1-4 hydroxyalkyl group, a C1-4 aminoalkyl group which is optionally substituted with one or more substituents selected from halogen atoms, hydroxy groups and -CF3 groups; ○ a 4 to 6-membered saturated N-containing heterocyclic ring optionally substituted with a C1-2 carboxyalkyl group; ○ -(CH2)(0-4)-C(O)OR', -(CH2)(0-4)-C(O)NR'R", -(CH2)(0-4)-NHC(O)R", -S(O)2NR'R", -O-(CH2)(2-4)NR'R", -O-(CH2)(1-4)C(O)OR", -O-(CH2)(1-4)-C(O)NR'R", -(CH2)(0-4)-NR'R", -(CH2)(0-4)-CONHS(O)2R', -(CH2)(0-4)-NHS(O)2R' or -(CH2)(0-3)-N H-(CH2)(1-3)-(NH)(0-1)S(O)2R' wherein, ■ R' represents a hydrogen atom or a C1-4 alkyl group, ■ R" represents a hydrogen atom, a C1-4 alkyl group, a C3-4 cycloalkyl group, a C1-4 carboxyalkyl group, a C1-4 haloalkyl group, a C1-4 hydroxyalkyl group or a 6 membered, saturated N-containing heterocyclic ring, or ■ R' and R" together with the nitrogen atom to which they are attached from a 4 to 6 membered heterocyclic group which contains, as heteroatoms, one N atom and, optionally, one further atom selected from N and O, and which is optionally substituted with a carboxy or a C1-4 carboxyalkyl group, or Rc together with Rd form a C5-6 cycloalkyl group optionally substituted by a -NHRf group, wherein Rf is selected from the group consisting of a hydrogen atom and a carboxymethyl group; R2 and R3 are independently selected from the group consisting of hydrogen atoms, halogen atoms and C1-4 alkyl groups; and R4 is selected from the group consisting of a hydrogen atom, a phenyl group, a C3-4 cycloalkyl-C1-4 alkyl group, C1-4 aminoalkyl group, C1-4 haloalkyl group and a linear or branched C1-4 alkyl group which is optionally substituted by a phenyl or a pyridyl group.

  通用公式（I）的新衍生物，或其药用可接受盐或N-氧化物，其中， A选自-N-，-O-和-S-组成的群; B和C分别选自-N-和-O-组成的群，但至少有两个A，B和C是氮原子; G1选自-CH2-，-NH-和-O-组成的群; G2选自-NR4-和-O-组成的群; R1代表: ➢一个含氮杂环的8到10成员双环基团，可选择地取代为C1-4羧基烷基基团或C1-4氨基烷基基团， ➢一个吡啶基，可选择地取代为一个或多个取代基，所选取代基包括羟基、C1-4烷基基团、C1-4羧基烷基基团、C1-4卤代烷基基团、C1-4烷氧基团、氨基、C1-4氨基烷基基团和C1-4氨氧基团， ➢一个吡啶酮基，取代为一个或多个C1-4烷基基团；C1-4卤代烷基基团或C1-4氨基烷基基团，或 ➢一个公式的基团： 其中: • Ra代表氢原子、卤原子、C1-4烷基基团、C3-4环烷基基团或-CF3基团; • Rb代表氢原子、卤原子、C14烷基基团、-CF3基团或C1-4烷氧基团; • Rd代表氢原子、C1-4烷基基团或C1-4烷氧基团; • Rc代表: ○氢原子、C1-4羟基烷基基团、C1-4氨基烷基基团，可选择地取代为一个或多个取代基，所选取代基包括卤原子、羟基和-CF3基团; ○一个4到6成员饱和的含氮杂环环，可选择地取代为C1-2羧基烷基基团; ○-(CH2)(0-4)-C(O)OR'，-(CH2)(0-4)-C(O)NR'R"，-(CH2)(0-4)-NHC(O)R"，-S(O)2NR'R"，-O-(CH2)(2-4)NR'R"，-O-(CH2)(1-4)C(O)OR"，-O-(CH2)(1-4)-C(O)NR'R"，-(CH2)(0-4)-NR'R"，-(CH2)(0-4)-CONHS(O)2R'，-(CH2)(0-4)-NHS(O)2R'或-(CH2)(0-3)-N H-(CH2)(1-3)-(NH)(0-1)S(O)2R'其中， ■ R'代表氢原子或C1-4烷基基团， ■ R"代表氢原子、C1-4烷基基团、C3-4环烷基基团、C1-4羧基烷基基团、C1-4卤代烷基基团、C1-4羟基烷基基团或6成员饱和的含氮杂环环，或 ■ R'和R"与它们连接的氮原子一起形成一个4到6成员的杂环基团，该基团包含一个N原子和可选择地一个进一步选择自N和O的原子，并可选择地取代为羧基或C1-4羧基烷基基团， 或Rc与Rd一起形成一个可选择地由-NHRf基团取代的C5-6环烷基基团，其中Rf选自氢原子和羧甲基基团; R2和R3分别选自氢原子、卤原子和C1-4烷基基团;和 R4选自氢原子、苯基团、C3-4环烷基-C1-4烷基基团、C1-4氨基烷基基团、C1-4卤代烷基基团和可选择地由苯基或吡啶基取代的线性或支链C1-4烷基基团。
• Synthesis of 3-Methyl and 7-Methyl Regio Isomers of Medorinone
  作者：Baldev Singh、George Y. Lesher、Ruth P. Brundage

  DOI：10.1055/s-1991-26604

  日期：——

  Reaction of 3-aminocrotononitrile (2) with methyl methacrylate (3) and methyl 2-propynolate (9) led to the formation of 1,4,5, 6-tetrahydro-2,5-dimethyl-6-oxo-3-pyridinecarbonitrile (4) and 1, 6-dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile (10), respectively. Condensation of 4 with Bredereck's reagent [bis(dimethylamino)-tert-butoxymethane], and that of 6-methoxy-2-methyl-3-pyridinecarbonitrile (12) with N,N-dimethylacetamide dimethyl acetal gave the corresponding enamines 5 and 13 which in turn were cyclized with hydrogen bromide to bromonaphthyridinones 6 and 14, respectively. Debromination of 6 followed by dehydrogenation gave 3-methyl-1,6-naphthyridin-2(1H)-one (8). Debromination of 14 with catalytic reduction gave 7-methyl-1, 6-naphthyridin-2(1H)-one (15)

  3-aminocrotononitrile (2) 与甲基丙烯酸甲酯 (3) 和 2-丙炔酸甲酯 (9) 反应，分别生成 1,4,5,6-四氢-2,5-二甲基-6-氧代-3-吡啶甲腈 (4) 和 1,6-二氢-2-甲基-6-氧代-3-吡啶甲腈 (10)。 4 与 Bredereck 试剂[双（二甲基氨基）-叔丁氧基甲烷]缩合，以及 6-甲氧基-2-甲基-3-吡啶甲腈（12）与 N,N-二甲基乙酰胺二甲基缩醛缩合，得到相应的烯胺 5 和 13，再与溴化氢环化，分别得到溴萘啶酮 6 和 14。6 脱溴后脱氢得到 3-甲基-1,6-萘啶-2(1H)-酮（8）。 14 在催化还原作用下脱溴，得到 7-甲基-1,6-萘啶-2(1H)-酮 (15)
• 2-[2-(di-lower-alkylamino)-1
  申请人：Sterling Drug Inc.

  公开号：US04634772A1

  公开（公告）日：1987-01-06

  2-[2-(di-lower-alkylamino-1-propenyl]-6-methoxy-3-pyridinecarbonitriles, useful as intermediates for cardiotonic agents.

  2-[2-(二烷基氨基-1-丙烯基)-6-甲氧基-3-吡啶碳腈，可用作心力衰竭药物的中间体。