Methyl ether of 1-(4-chlorophenylaminocarbonyloxy)-1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime | 121750-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl ether of 1-(4-chlorophenylaminocarbonyloxy)-1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime
• 英文别名: [5-(methoxyiminomethyl)-3,6-dihydro-2H-pyridin-1-yl] N-(4-chlorophenyl)carbamate
• CAS: 121750-78-5
• 化学式: C₁₄H₁₆ClN₃O₃
• 分子量: 309.752
• InChiKey: XZQZAGAUOUPLDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  对氯苯异氰酸酯 生成 Methyl ether of 1-(4-chlorophenylaminocarbonyloxy)-1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime
  参考文献：
  名称：

  Oxime of 1, 2, 5, 6-tetrahydropyridine compounds their use as

  摘要：

  用于治疗患有老年性痴呆症、阿尔茨海默病或记忆缺陷的化合物，其化学式为##STR1##其中R代表氢或含有最多8个碳原子的线性、支链或环状烷基、烯基或炔基，或基团##STR2##其中R.sub.1代表含有最多8个碳原子的线性或支链烷基、烯基或炔基，含有最多8个碳原子的线性或支链饱和或不饱和的烷氧基，或含有最多14个碳原子的芳基，或基团##STR3##其中R.sub.2代表含有最多8个碳原子的线性或支链烷基、烯基或炔基，含有最多14个碳原子的芳基，可能被取代，或含有最多18个碳原子的芳基烷基，可能被取代，R'代表含有最多8个碳原子的线性、支链或环状烷基、烯基或炔基，以及它们与有机或矿物酸的盐。

  公开号：

  US04902699A1

文献信息

• 1-substituted-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyloximes as novel orally active and long-lasting muscarinic cholinergic agonists
  作者：E Toja、C Bonetti、A Butti、P Hunt、M Fortin、F Barzaghi、ML Formento、A Maggioni、A Nencioni、G Galliani

  DOI：10.1016/0223-5234(92)90186-5

  日期：1992.8

  Our previous attempts to design muscarinic agonists related to arecoline with the prerequisites for clinical use were successful with the discovery of 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime hydrochloride, RU 35963, and structurally related compounds, in which die metabolically labile ester group of arecoline was replaced with the bioisosteric and stable aldoxime group. With the aim of obtaining compounds with improved cholinomimetic properties, several aryl- and alkyl-carbamates of RU 35963, as well as O-alkyl-, and O-aryl-carbamates of the 1-hydroxy-1,2,5,6-tetrahydropyridine-3- carboxaldehyde-O-methyloxime hydrochloride, 24, have been synthesized and evaluated biologically. The most interesting molecules to emerge from the primary screening have been evaluated more extensively and their cholinomimetic profiles compared with those of the parent molecules. In vitro studies indicate that none of these prodrugs have affinity for muscarinic receptor sites and some of them (aryl-carbamates) have cholinesterase inhibiting properties. Results from in vivo experiments in mice and rats showed that these new substances, 1-[4-chlorophenyl] oxycarbonyl-1,2,5,6-tetrahydropyridine-3- carboxaldehyde-O-methyloxime (16 = RU 47213) in particular, have cholinomimetic properties that compare favourably with those of the parent compounds. After oral administration 16 was clearly superior to RU 35963 in terms of central selectivity, duration of action and therapeutic indexes.
• Oxime of 1, 2, 5, 6-tetrahydropyridine compounds their use as
  申请人：Roussel Uclaf

  公开号：US04902699A1

  公开（公告）日：1990-02-20

  Compounds useful in the treatment of patients suffering from senile dementia, Alzheimer's disease or memory defects, of the formula ##STR1## in which R represents hydrogen or a linear, branched or cyclic alkyl, alkenyl, or alkynyl, containing up to 8 carbon atoms, or the radical ##STR2## in which R.sub.1 represents a linear or branched, alkyl, alkenyl or alkynyl, containing up to 8 carbon atoms, a linear or branched, saturated or unsaturated, alkoxy containing up to 8 carbon atoms, or aryl containing up to 14 carbon atoms, or the radical ##STR3## in which R.sub.2 represents a linear or branched alkyl, alkenyl or alkynyl, containing up to 8 carbon atoms, aryl containing up to 14 carbon atoms, possibly substituted, or aralkyl containing up to 18 carbon atoms, possibly substituted, and R' represents a linear, branched or cyclic alkyl, alkenyl or alkynyl, containing up to 8 carbon atoms, as well as their addition salts with organic or mineral acids.

  用于治疗患有老年性痴呆症、阿尔茨海默病或记忆缺陷的化合物，其化学式为##STR1##其中R代表氢或含有最多8个碳原子的线性、支链或环状烷基、烯基或炔基，或基团##STR2##其中R.sub.1代表含有最多8个碳原子的线性或支链烷基、烯基或炔基，含有最多8个碳原子的线性或支链饱和或不饱和的烷氧基，或含有最多14个碳原子的芳基，或基团##STR3##其中R.sub.2代表含有最多8个碳原子的线性或支链烷基、烯基或炔基，含有最多14个碳原子的芳基，可能被取代，或含有最多18个碳原子的芳基烷基，可能被取代，R'代表含有最多8个碳原子的线性、支链或环状烷基、烯基或炔基，以及它们与有机或矿物酸的盐。