KR970701695A - New 1.4-Disubstituted Piperidine Derivatives Useful as Medicaments Acting on The Glutamate Receptor - Google Patents

New 1.4-Disubstituted Piperidine Derivatives Useful as Medicaments Acting on The Glutamate Receptor

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Publication number
KR970701695A
KR970701695A KR1019960705269A KR19960705269A KR970701695A KR 970701695 A KR970701695 A KR 970701695A KR 1019960705269 A KR1019960705269 A KR 1019960705269A KR 19960705269 A KR19960705269 A KR 19960705269A KR 970701695 A KR970701695 A KR 970701695A
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piperidyl
ketone
naphthyloxy
fluorophenyl
propyl
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KR1019960705269A
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Korean (ko)
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디이터 자이델만
안드레아스 후트
마르틴 크뤼거
에크하르트 오토브
그래함 존스 존스
롤란트 노이하우스
레코슬라브 투르스키
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마거, 키르쉬
쉐링 악티엔게젤샤프트
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Publication of KR970701695A publication Critical patent/KR970701695A/en

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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/02—Antidotes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

본 발명은 하기 화학식(I)의 화합물 및 그의 제조 방법 및 약제학적 제제에서의 그의 용도를 제공한다.The present invention provides compounds of formula (I) and methods for their preparation and their use in pharmaceutical formulations.

Description

글루타메이트 수용체에 작용하는 약제로서 유용한 신규 1,4ㅡ이치환 피페리딘 유도체 (New 1,4ㅡDisubstituted Piperidine Derivatives Useful as Medicaments Acting on The Glutamate Receptor)New 1,4 ㅡ Disubstituted Piperidine Derivatives Useful as Medicaments Acting on The Glutamate Receptor

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (4)

하기 화학식(I)의 화합물 및 그의 생리학적으로 허용 가능한 염 및 이성질체.The compounds of formula (I) and their physiologically acceptable salts and isomers. 상기 식에서, R1은 치환 또는 비치환된 페닐, 치환 또는 비치환된 피리딘, 치환 또는 비치환된 나프탈렌, 치환 또는 비치환된 퀴놀린, 치환 또는 비치환된 이소퀴놀린, 치환 또는 비치환된 인돌, 치환 또는 비치환된 벤조티오펜, 치환 또는 비치환된 벤조푸란, 치환 또는 비치환된 테트라히드로퀴놀린, 치환 또는 비치환된 테트라히드로이소퀴놀린, 치환 또는 비치환된 테트랄린, 치환 또는 비치환된 디히드로나프탈렌, 치환 또는 비치환된 인단, 치환 또는 비치환된 인다논, 치환 또는 비치환된 테트랄론, 치환 또는 비치환된 크로멘ㅡ2ㅡ온, 치환 또는 비치환된 나프토퀴논이고, Z는 산소, 황, SO 또는 SO2이고, X는 ㅡ(CH2)mㅡCR2R|3ㅡ(CH2)p이거나 또는 ㅡ(CH2)mㅡCHR2ㅡ(CH2)gㅡCHR3ㅡ(CH|2)pㅡ(여기서, m,p,g는 각각 0,1,2 또는 3이고, R2및 R3는 서로 동일하거나 또는 상이할 수 있으며, 수소, 히드록시, C1-4알킬, C1ㅡ4알콕시, 또는 C1ㅡ6알카노일옥시를 나타낸다)이고, B는(여기서, R4는 직쇄 또는 분지쇄의 C1ㅡ6알킬,이거나 또는 C1ㅡ4알킬, C1ㅡ4알콕시, 할로겐, 히드록시, ㅡCF3또는 ㅡOㅡCF3에 의해 임의로 치환되고, 여기서 하나 내지 세개의 위치에서의 치환기가 동일하거나 또는 상이할 수 있는 페닐, 벤질, 벤조일, αㅡ히드록시벤질, 피리디닐 또는 나프토일 기를 나타내고, Y는 산소, 황 또는 ㅡNHㅡ를 나타낸다)이다.Wherein R 1 is substituted or unsubstituted phenyl, substituted or unsubstituted pyridine, substituted or unsubstituted naphthalene, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted indole, substituted Or unsubstituted benzothiophene, substituted or unsubstituted benzofuran, substituted or unsubstituted tetrahydroquinoline, substituted or unsubstituted tetrahydroisoquinoline, substituted or unsubstituted tetralin, substituted or unsubstituted di Hydronaphthalene, substituted or unsubstituted indane, substituted or unsubstituted indanone, substituted or unsubstituted tetraralone, substituted or unsubstituted chromen-2-one, substituted or unsubstituted naphthoquinone, and Z is Oxygen, sulfur, SO or SO 2 , and X is — (CH 2 ) m —CR 2 R | 3- (CH 2 ) p or-(CH 2 ) m -CHR 2- (CH 2 ) g -CHR 3- (CH | 2 ) p- (where m, p, g are 0,1,2, respectively) or 3, R 2 and R 3 may be the same or different from each other, represent hydrogen, hydroxy, C 1-4 alkyl, C 1 sul 4 alkoxy, or C 1 sul 6 alkanoyloxy), and B Is Wherein R 4 is straight or branched C 1-6 alkyl, Or optionally substituted by C 1-4 alkyl, C 1-4 alkoxy, halogen, hydroxy, —CF 3 or —O—CF 3 , wherein the substituents at one to three positions may be the same or different Phenyl, benzyl, benzoyl, α-hydroxybenzyl, pyridinyl or naphthoyl groups, and Y represents oxygen, sulfur or -NH. 제1항에 있어서, {1ㅡ[3ㅡ(1ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤(1ㅡ[3ㅡ(2ㅡ나프틸옥시]-프로필]-4-피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤{1ㅡ[3ㅡ(2ㅡ니트로ㅡ1ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(1ㅡ니트로ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ2,4ㅡ디니트로ㅡ1ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 (4ㅡ플루오로페닐)ㅡ{1ㅡ[3ㅡ(5ㅡ이소퀴놀릴옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ케톤 {1ㅡ[3ㅡ(1ㅡ브로모ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(4-클로로-1-나프틸옥시)-프로필]-4ㅡ피페리딜}-(4-플루오로페닐)-케톤 1ㅡ{1ㅡ[3ㅡ(1ㅡ나프틸옥시)ㅡ2-히드록시프로필)-4-피페리딜}-(4-플루오로페닐)-케톤 {1-[3-(2-나프틸옥시)-2-히드록시프로필)4-피페리딜}-(4ㅡ플루오로페닐)ㅡ케톤 1-{1-[3-(1-나프틸옥시)-프로필)-4-피페리딜)-1-(4-플루오로페닐)-에탄올 1ㅡ{1ㅡ[3ㅡ(2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ1ㅡ(4ㅡ플루오로페닐)ㅡ메탄올 1ㅡ나프틸ㅡ{3ㅡ[4ㅡ(4ㅡ플루오로벤질)ㅡ1ㅡ피페리딜]ㅡ프로필}ㅡ에테르 2ㅡ나프틸ㅡ{3ㅡ[4ㅡ(4ㅡ플루오로벤질)ㅡ1ㅡ피페리딜]ㅡ프로필}ㅡ에테르 {1ㅡ[3ㅡ(1ㅡ브로모ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(4ㅡ클로로ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 4ㅡ{3ㅡ[4ㅡ(4ㅡ플루오로벤조일)ㅡ1ㅡ피페리딜]ㅡ프로폭시}ㅡ인단ㅡ1ㅡ온 5ㅡ{3ㅡ[4ㅡ(플루오로벤조일)ㅡ1ㅡ피페리딜]ㅡ프로폭시}ㅡ3,4ㅡ디히드로나프탈레느1(2H)ㅡ온 {1ㅡ[3ㅡ(7,8ㅡ디히드로ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(7,8ㅡ디히드로ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(3,4ㅡ디플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(7ㅡ,8ㅡ디히드로ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(3,4ㅡ디메톡시페닐)ㅡ케톤 7ㅡ{3ㅡ[4ㅡ(4ㅡ플루오로벤조일)ㅡ1ㅡ피페리딜]ㅡ프로폭시}ㅡ2Hㅡ크로멘ㅡ2ㅡ온 7ㅡ{3ㅡ[4ㅡ(4ㅡ플루오로벤조일)ㅡ1ㅡ피페리딜]ㅡ프로폭시}ㅡ4ㅡ메틸ㅡ2Hㅡ크로멘ㅡ2ㅡ온 4ㅡ{3ㅡ[4ㅡ(4ㅡ플루오로벤조일)ㅡ1ㅡ피페리딜]ㅡ프로폭시}ㅡ2Hㅡ크로멘ㅡ2ㅡ온 {1ㅡ[3ㅡ(6ㅡ브로모ㅡ2ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(2ㅡ나프틸옥시)ㅡ2ㅡ히드록시프로필)ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(1ㅡ나프틸옥시)ㅡ2ㅡ히드록시프로필)ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 (4ㅡ플루오로페닐)ㅡ{1ㅡ[3ㅡ(1ㅡ옥소ㅡ1,2,3,4ㅡ테트라히드로ㅡ5ㅡ나프틸옥시)ㅡ2ㅡ히드록시프로필]ㅡ4ㅡ피페리딜}ㅡ케톤 {1ㅡ[3ㅡ(1ㅡ나프틸옥시)ㅡ2ㅡ히드록시프로필)ㅡ4ㅡ피페리딜}ㅡ(3,4ㅡ디메톡시페닐)ㅡ케톤 {1ㅡ[3ㅡ(1ㅡ나프틸옥시)ㅡ2ㅡ히드록시프로필)ㅡ4ㅡ피페리딜}ㅡ(3,4ㅡ디플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(2ㅡ나프틸옥시)ㅡ2ㅡ히드록시프로필)ㅡ4ㅡ피페리딜}ㅡ(3,4ㅡ디플루오로페닐)ㅡ케톤 2ㅡ[4ㅡ(4ㅡ플루오로벤질)ㅡ피페리디노)ㅡ2ㅡ메톡시프로폭시]ㅡ나프탈렌 {1ㅡ[3ㅡ(1ㅡ나프틸옥시)ㅡ2ㅡ메톡시프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 {1ㅡ[3ㅡ(2ㅡ나프틸옥시)ㅡ2ㅡ메톡시프로필]ㅡ4ㅡ피페리딜}ㅡ(4ㅡ플루오로페닐)ㅡ케톤 (4ㅡ플루오로페닐)ㅡ{1ㅡ[3ㅡ(1,2,3,4ㅡ테트라히드로ㅡ5ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ케톤 (4ㅡ플루오로페닐)ㅡ{1ㅡ[3ㅡ(인단ㅡ4ㅡ일옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ케톤 (4ㅡ플루오로페닐)ㅡ{1ㅡ[3ㅡ(인단ㅡ5ㅡ일옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ케톤 (3,4ㅡ디플루오로페닐)ㅡ{1ㅡ[3ㅡ(인단ㅡ4ㅡ일옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ케톤 (4ㅡ플루오로페닐)ㅡ{1ㅡ[3ㅡ(1,2,3,4ㅡ테트라히드로ㅡ6ㅡ나프틸옥시)ㅡ프로필]ㅡ4ㅡ피페리딜}ㅡ케톤The method according to claim 1, wherein {1-[3-(1-naphthyloxy) -propyl]-4-piperidyl}-(4-fluorophenyl)-ketone (1-[3-(2-naphthyloxy). ] -Propyl] -4-piperidyl}-(4-fluorophenyl)-ketone {1-[3-(2-nitro-1-naphthyloxy)-propyl]-4-piperidyl}-(4 -Fluorophenyl) -ketone {1-[3-(1-nitro-2-naphthyloxy)-propyl]-4-piperidyl}-(4-fluorophenyl)-ketone {1-[3-2 , 4 -Dinitro -1 -naphthyloxy) -propyl] -4 -piperidyl}-(4 -fluorophenyl) -ketone (4 -fluorophenyl)-{1-[3-(5 -isoquinolyl Oxy) -propyl]-4-piperidyl}-ketone {1-[3-(1-bromo-2-naphthyloxy)-propyl]-4-piperidyl}-(4-fluorophenyl)-ketone {1-[3-(4-chloro-1-naphthyloxy) -propyl] -4 -piperidyl}-(4-fluorophenyl) -ketone 1-{1-[3-(1 -naphthyloxy ) -2-hydroxypropyl) -4-piperidyl}-(4-fluorophenyl)- Ton {1- [3- (2-naphthyloxy) -2-hydroxypropyl) 4-piperidyl}-(4-fluorophenyl) -ketone 1- {1- [3- (1-naphthyl Oxy) -propyl) -4-piperidyl) -1- (4-fluorophenyl) -ethanol 1-{1-[3-(2-naphthyloxy)-propyl]-4-piperidyl}-1 -(4 -fluorophenyl) -methanol 1 -naphthyl-{3-[4-(4-(fluorofluoro) -1 -piperidyl] -propyl} -ether 2 -naphthyl-{3-[4- (4 -fluorobenzyl) -1-piperidyl] -propyl}-ether {1-[3-(1-bromo-2-naphthyloxy)-propyl]-4-piperidyl}-(4-fluorine Lophenyl) -ketone {1-[3-(4-chloro-2-naphthyloxy)-propyl]-4-piperidyl}-(4-fluorophenyl)-ketone 4-{3-[4-( 4 -fluorobenzoyl) -1 -piperidyl] -propoxy} -indan -1 on 5-{3-[4-(fluorobenzoyl) -1 -piperidyl] -propoxy} -3,4 -dihydro Naphthalene 1 (2H)-On {1-[3-(7,8-Dihydro-2-Naphthyl jade ) -Propyl]-4-piperidyl}-(4-fluorophenyl)-ketone {1-[3-(7,8-dihydro-2-naphthyloxy)-propyl]-4-piperidyl}-( 3,4-difluorophenyl) -ketone {1-[3-(7-, 8 -dihydro-2-naphthyloxy) -propyl]-4-piperidyl}-(3,4-dimethoxyphenyl)- Ketone 7- {3-[4-(4 -fluorobenzoyl) -1 -piperidyl] -propoxy} -2H -chromen -2-7-{3-[4-(4 -fluorobenzoyl) ㅡ 1-piperidyl]-propoxy}-4-methyl-2H-chromaen-2-4-{3-[4-(4-fluorobenzoyl)-1-piperidyl]-propoxy}-2H Meno 2-one {1-[3-(6 bromo-2-naphthyloxy) -propyl]-4-piperidyl}-(4-fluorophenyl)-ketone {1-[3-(2- Naphthyloxy) -2-hydroxypropyl) -4-piperidyl}-(4-fluorophenyl)-ketone {1-[3-(1-naphthyloxy)-2-hydroxypropyl)-4-blood Ferridyl} ㅡ (4 fluorophenyl) ㅡ Ton (4-fluorophenyl)-{1-[3-(1-oxo-1,2,3,4-tetrahydro-5-naphthyloxy)-2-hydroxypropyl]-4-piperidyl} -Ketone {1-[3-(1-naphthyloxy)-2-hydroxypropyl)-4-piperidyl}-(3,4-dimethoxyphenyl)-ketone {1-[3-(1-naph Tyloxy) -2-hydroxypropyl) -4-piperidyl}-(3,4-difluorophenyl)-ketone {1-[3-(2-naphthyloxy)-2-hydroxypropyl)-4 -Piperidyl}-(3,4-difluorophenyl)-ketone 2-[4-(4-fluorobenzyl)-piperidino)-2-methoxypropoxy]-naphthalene {1-[3-(1-) Naphthyloxy) -2-methoxypropyl]-4-piperidyl}-(4-fluorophenyl)-ketone {1-[3-(2-naphthyloxy)-2-methoxypropyl]-4-piperidyl }-(4 -fluorophenyl)-ketone (4-fluorophenyl)-{1-[3-(1,2,3,4-tetrahydro-5-naphthyloxy) -propyl]-4-piperi Deal} ketone (4flu Lophenyl)-{1-[3-(indan -4 -yloxy) -propyl] -4 -piperidyl} -ketone (4 -fluorophenyl)-{1-[3-(indan -5 -yloxy ) -Propyl]-4-piperidyl}-ketone (3,4-difluorophenyl)-{1-[3-(indan-4-yloxy)-propyl]-4-piperidyl}-ketone (4- Fluorophenyl)-{1-[3-(1,2,3,4-tetrahydro-6-naphthyloxy)-propyl]-4-piperidyl}-ketone 제1항 및 제2항에 따른 화합물에 기초한 약제학적 제제.A pharmaceutical formulation based on the compound according to claim 1. a) 하기 화학식(Ⅱ)의 화합물을 하기 화학식(Ⅲ)의 화합물과 반응시키거나,a) reacting a compound of formula (II) with a compound of formula (III) (상기 식에서, B,X,Z 및 R1은 상기 정의된 바와 같고, A는 이탈기이다) b) 하기 화학식(Ⅳ)의 화합물을 하기 화학식(Ⅴ)의 아민과 반응시키거나,(Wherein B, X, Z and R 1 are as defined above and A is a leaving group) b) reacting a compound of formula (IV) with an amine of formula (V), (상기 식에서, B,X,Z 및 R1은 상기 정의된 바와 같고, A는 이탈기이다) c) 하기 화학식(Ⅵ)의 에폭사이드를 하기 화학식(Ⅴ)의 아민과 반응시키거나,(Wherein B, X, Z and R 1 are as defined above and A is a leaving group) c) reacting the epoxide of formula (VI) with an amine of formula (V), (상기 식에서, m,Z 및 R1은 상기 정의된 바와 같다) d) 하기 화학식(Ⅶ)의 화합물을 화학식 R1ㅡOH의 화합물과 미츠노부(Mitsunobu) 반응시킨 후, 임의의 카르보닐기를 환원시키거나 또는 히드록시기를 에스테르화시키거나 또는 에테르화시키거나 또는 생리적으로 허용 가능한 염을 제조하거나 또는 이성질체를 분리하는 것으로 이루어진 제1항의 화합물의 제조 방법.(Wherein m, Z and R 1 are as defined above) d) After reacting a compound of formula (VII) with a compound of formula R 1 -OH and Mitsunobu, any carbonyl group is reduced. Or esterifying or etherifying a hydroxy group or preparing a physiologically acceptable salt or isolating isomers. (상기 식에서, X 및 B은 상기 정의된 바와 같다)Wherein X and B are as defined above ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
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CZ277096A3 (en) 1997-01-15
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WO1995025721A1 (en) 1995-09-28
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DE4410822A1 (en) 1995-09-28
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FI963786A0 (en) 1996-09-23
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CA2186010A1 (en) 1995-09-28
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HUT75653A (en) 1997-05-28

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