A NEW PREPARATIVE METHOD FOR THE SYNTHESIS OF 6-[3-(1-ADAMANTYL)-4-METHOXYPHENYL]-2-NAPHTHOIC ACID

被引:5
|
作者
Tribulovich, V. G. [1 ]
Garabadzhiu, A. V. [2 ]
Kalvin'sh, I. [3 ]
机构
[1] Minist Hlth & Social Dev Russian Federat, Sci Res Inst Influenza, St Petersburg, Russia
[2] St Petersburg State Technol Inst Tech Univ, St Petersburg, Russia
[3] Latvian Acad Sci, Inst Organ Synth, LV-226006 Riga, Latvia
关键词
Adapalene; 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid; 3-(1-adamantyl)-4-methoxyphenylboronic acid; synthesis; Suzuki-Miyaura cross-coupling; BR/MG EXCHANGE;
D O I
10.1007/s11094-011-0605-z
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new method for the synthesis of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid (adapalene) was developed, characterized by stable high yields of intermediate and end products, simple scale-up, and technical feasibility.
引用
收藏
页码:241 / 244
页数:4
相关论文
共 50 条
  • [1] A new preparative method for the synthesis of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid
    V. G. Tribulovich
    A. V. Garabadzhiu
    I. Kalvin’sh
    Pharmaceutical Chemistry Journal, 2011, 45 : 241 - 244
  • [2] New synthesis of 6[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid and evaluation of the influence of adamantyl group on the DNA binding of a naphthoic retinoid
    Milanese, Alberto
    Gorincioi, Elena
    Rajabi, Mehdi
    Vistoli, Giulio
    Santaniello, Enzo
    BIOORGANIC CHEMISTRY, 2011, 39 (4-6) : 151 - 158
  • [3] SYNTHESIS OF C-14-LABELED CD-271 (6-[3-(1-ADAMANTYL)-4-METHOXYPHENYL]2-NAPHTHOIC ACID) - A POTENTIAL NEW AGENT FOR DERMATOLOGY
    PILGRIM, WR
    NEDONCELLE, P
    FRIDELING, JP
    SHROOT, B
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1991, 29 (07): : 841 - 846
  • [4] One-Pot Synthesis of Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthenoate
    Tribulovich, V. G.
    Garabadzhiu, A. V.
    Kalvins, I.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (04) : 870 - 871
  • [5] One-pot synthesis of methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthenoate
    V. G. Tribulovich
    A. V. Garabadzhiu
    I. Kalvins
    Russian Journal of General Chemistry, 2010, 80 : 870 - 871
  • [6] Synthesis of 3-(1-Adamantyl)-4-methoxyphenylboric Acid
    Tribulovich, V. G.
    Garabadzhiu, A. V.
    Kalvins, I.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (04) : 868 - 869
  • [7] Synthesis of 3-(1-adamantyl)-4-methoxyphenylboric acid
    V. G. Tribulovich
    A. V. Garabadzhiu
    I. Kalvins
    Russian Journal of General Chemistry, 2010, 80 : 868 - 869
  • [8] 3-(2,4,6-Trimethylbenzoyl)-2-naphthoic acid
    Thenmozhi, S.
    ArulClement, J.
    MohanaKrishnan, A. K.
    SubbiahPandi, A.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2794 - U2409
  • [9] SYNTHESIS OF 6-(1-ADAMANTYL)-3-CYANOPYRIDINE-2(1H)-ONE AND 6-(1-ADAMANTYL)-3-CYANOPYRIDINE-2(1H)-SELENONE
    LITVINOV, VP
    APENOVA, EE
    SHARANIN, YA
    SHESTOPALOV, AM
    ZHURNAL ORGANICHESKOI KHIMII, 1985, 21 (03): : 669 - 670
  • [10] ADAMANTYL-CONTAINING HETEROCYCLES .1. 3-(1-ADAMANTYL)-3-CHLOROPROPENAL IN THE SYNTHESIS OF 2-(1-ADAMANTYL)THIOPHENE AND 5-(1-ADAMANTYL)ISOXAZOLE
    LITVINOV, VP
    DERMUGIN, VS
    SHVEDOV, VI
    BOGDANOV, VS
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1984, 33 (07): : 1451 - 1455