KR790001688B1 - 5-벤질 피콜린산 유도체의 제법 - Google Patents

5-벤질 피콜린산 유도체의 제법 Download PDF

Info

Publication number
KR790001688B1
KR790001688B1 KR7500218A KR750000218A KR790001688B1 KR 790001688 B1 KR790001688 B1 KR 790001688B1 KR 7500218 A KR7500218 A KR 7500218A KR 750000218 A KR750000218 A KR 750000218A KR 790001688 B1 KR790001688 B1 KR 790001688B1
Authority
KR
South Korea
Prior art keywords
acid
preparation
hydrogen
lower alkoxy
picolinic acid
Prior art date
Application number
KR7500218A
Other languages
English (en)
Inventor
오사무 스즈카
마사오 무라야마
히로무 무라이
오사무 타나베
아키라 오오바야시
테루야 나카무라
Original Assignee
모리시타 히로시
닛뽄 신야쿠 가부시기가이샤
오오미야 타카시
타카라 슈조오 가부시기가이샤
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 모리시타 히로시, 닛뽄 신야쿠 가부시기가이샤, 오오미야 타카시, 타카라 슈조오 가부시기가이샤 filed Critical 모리시타 히로시
Priority to KR7500218A priority Critical patent/KR790001688B1/ko
Application granted granted Critical
Publication of KR790001688B1 publication Critical patent/KR790001688B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

내용 없음.

Description

5-벤질 피콜린산 유도체의 제법
본 발명은 일반식(II)로 나타낸 신규 피콜린산 유도체의 제법에 관한 것이다.
Figure kpo00001
(식중 R은 H 또는 저급 알킬을 나타내며 n은 1 혹은 2를 나타낸다.)
이들 화합물은 력강한 도파민-β-하이드록실라제 저해 활성을 가지며, 의약으로서 유용한 물질이다.
본 발명을 더욱 상세히 설명하면, 다음 일반식(I)로
Figure kpo00002
(식중 R은 전술한 바와 동일하고, R1, R2은 동일 또는 상이하며, H 혹은 저급알킬을 나타낸다. 단지 R1=R2=H인 경우는 제외한다.)
표시되는 화합물을 저급 알코올 혹은 수용매 중, 산(적당하기로는 할로겐화 수소산)의 존재하 상압 또는 가압하에서 가열함으로서 일반식(II)로 표시되는 화합물의 제법에 관한 것이다.
표 1에서, 본 발명에 의해 얻어진 대표적인 화합물에 있어서 그것의 융점 이외에 급성 독성, 도파민-β-하이드록실라제 저해활성을 나타낸 것이지만, 공지 화합물인 후자린산보다 월등 우수한 작용 효과가 있었다.
급성 독성 시험은 피검 화합물을 6주 정도 ddy계 웅성 백쥐에 복강내 투여후, 1주일간 관찰하여 산출하였다.
[표 1]
Figure kpo00003
이하 실시예에서 상세히 설명한다.
[실시예 1]
5-(4-하이드록시벤질)피콜린산의 제법
5-(4-메톡시벤질)피콜린산 1.5g에 47% 취화수소산 5㎖를 가하고, 3시간 가열 환류후, 방냉하고, 10% NaOH수용액에 pH 2부근까지 중화하면 결정이 석출한다. 이것을 여취하여, 메탄올에서 재결정하면 융점 213-215℃의 결정으로써 5-(4-하이드록시 벤질)피콜린산 1.0g을 얻는다.
[실시예 2]
5-(3, 4-디하이드록시벤질)피콜린산의 제법
5-(3, 4-디메톡시벤질)피콜린산 1.5g에 48%취화수소산 20㎖를 가하여 6시간 가열 환류한 후, 방냉하여 석출된 결정을 여취한다.
이 결정을 10% 암모니아수에 용해하고, 활성탄 처리를 행하여, 희 염산에서 pH2-3으로 하면 결정이 석출한다. 이것을 여취하면 분해점 246-249℃의 적갈색의 결정으로서 5-(3, 4-디하이드록시 벤질)피콜린산 0.8g을 얻는다.
[실시예 3]
5-(4-하이드록시 벤질)피콜린산 에틸에스테르의 제법
5-(4-메톡시벤질)피콜린산 에틸에스테르 1g을 염산 포화에틸 알코올 20㎖에 용하여 봉관 중에서 120℃로 24시간 가열후, 용매를 유거하고, 잔사에 냉수를 가하여, 석출 결정을 여취한다음, 초산 에틸에스테르에서 재결정하면 융점 153-156℃의 무색 침상 결정으로서 5-(4-하이드록시 벤질)피콜린산 에틸에스테르 0.8g을 얻는다.

Claims (1)

  1. 다음 일반식(I)로 표시된 화합물을 물 또는 저급 알코올 중에서, 산존재하에 가열함을 특징으로 하는 일반식(II)의 5-벤질피콜린산 유도체의 제법.
    Figure kpo00004
    식중, R은 H 혹은 저급 알킬이고 R1, R2는 동일 또는 상이하며, H, 혹은 저급알콕시를 나타낸다. 단, R1=R2=H의 경우는 제외한다.
KR7500218A 1975-02-03 1975-02-03 5-벤질 피콜린산 유도체의 제법 KR790001688B1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR7500218A KR790001688B1 (ko) 1975-02-03 1975-02-03 5-벤질 피콜린산 유도체의 제법

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR7500218A KR790001688B1 (ko) 1975-02-03 1975-02-03 5-벤질 피콜린산 유도체의 제법

Publications (1)

Publication Number Publication Date
KR790001688B1 true KR790001688B1 (ko) 1979-12-08

Family

ID=19200924

Family Applications (1)

Application Number Title Priority Date Filing Date
KR7500218A KR790001688B1 (ko) 1975-02-03 1975-02-03 5-벤질 피콜린산 유도체의 제법

Country Status (1)

Country Link
KR (1) KR790001688B1 (ko)

Similar Documents

Publication Publication Date Title
US3895028A (en) Alpha-(2-phenylbenzothiazol-5-yl)propionic acid
SU1609449A3 (ru) Способ получени индентиазола
US2579478A (en) Heterocyclic compounds
KR790001688B1 (ko) 5-벤질 피콜린산 유도체의 제법
US2840559A (en) Nuclearly substituted 8-theophyllines and method of making the same
US3001992A (en) S-niteo-z-fubftjewdene
US4297357A (en) N-Phenethylacetamide compounds and process for preparation thereof
DE3118521A1 (de) Dibenzo(de,g)chinolin-derivate, verfahren zu deren herstellung und deren verwendung bei der bekaempfung von erkaeltungskrankheiten und allergien
US2540946A (en) Pyridoxal-histamine and processes for preparing the same
US2266754A (en) Synthesis of vitamin
US3201406A (en) Pyridylcoumarins
US3793314A (en) Cinnamic acid esters of 7-nitro-8-hydroxy-quinoline
US2728769A (en) Alkoxybenzylisoquinolines and salts thereof
JPS5940155B2 (ja) ４−オキソヘキサヒドロピラジノイソキノリン誘導体の製造方法
US3583992A (en) 1-methyl-d-lysergic acid-dihydroxy-alkyl-amides
US2762805A (en) 3-ethyl-3-phenyl-2, 6-piperazinedione and derivatives thereof
US2461950A (en) or x-amino quinazolines
US2874156A (en) Substituted l
SU584782A3 (ru) Способ получени производных аминоимидазоизохинолина или их солей
US3450709A (en) Process for the preparation of ring-substituted 2-aminoimidazoles
US3244725A (en) 4, 5-diacyl-3-hydroxy-3-pyrrolin-2-ones
US2762804A (en) 3-methyl-5-phenyl-2, 6-piperazinedione and derivatives thereof and method of preparing same
US3135759A (en) Manotactuse of organic chemical
US2374367A (en) Process for preparing therapeutically active substances
US2861996A (en) Process of preparing serines