KR930016419A - Substituted imidazole derivatives and preparation method thereof - Google Patents

Substituted imidazole derivatives and preparation method thereof Download PDF

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KR930016419A
KR930016419A KR1019920000354A KR920000354A KR930016419A KR 930016419 A KR930016419 A KR 930016419A KR 1019920000354 A KR1019920000354 A KR 1019920000354A KR 920000354 A KR920000354 A KR 920000354A KR 930016419 A KR930016419 A KR 930016419A
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hydrogen
substituted
lower alkyl
formula
lower alkoxy
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정유섭
김동익
임재욱
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이성훈
주식회사 중외제약
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G02F1/133516—Methods for their manufacture, e.g. printing, electro-deposition or photolithography
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G02F1/133519—Overcoatings

Abstract

본 발명은 위산분비억제 작용을 갖는 신규한 하기 일반식(Ⅰ)의 치환된 이미다졸 유도체 및 그의 염, 그의 제조 방법 및 이 화합물을 활성성분으로 함유하는 약제학적 조성물에 관한 것이다.The present invention relates to novel substituted imidazole derivatives of the general formula (I) and salts thereof having a gastric acid secretion action, a preparation method thereof, and a pharmaceutical composition containing the compound as an active ingredient.

상기 식에서, A는 CR 또는 질소원자이고; R은 수소, 저급 알킬 또는 저급 알콕시이며, R1은 수소, 저급 알킬 또는 저급 알콕시를 나타내거나, R과 R1이 함께는 치환되거나 비치환된 벤젠환을 형성할 수도 있으며; Y는 일반 식 (a) 또는 (b)의 치환된 헤테로사이클릭 그룹이고,Wherein A is CR or a nitrogen atom; R is hydrogen, lower alkyl or lower alkoxy, R 1 represents hydrogen, lower alkyl or lower alkoxy, or R and R 1 may together form a substituted or unsubstituted benzene ring; Y is a substituted heterocyclic group of the general formula (a) or (b),

단, 여기에서 Y가 일반식(a)의 헤테로사이클릭 그룹을 나타내고 A가 CR인 경우에는, R과 R1이 함께 치환되거나 비치환된 벤젠환을 형성하거나 R2와 R3가 함께 피리딘환에 축합된 벤젠환을 형성하여야 하며; R2는 수소 또는 저급 알킬이고, R3는 수소, 저급 알콕시, 할로겐-치환된 저급 알콕시, 또는 치환되거나 비치환된 벤질옥시이거나, R2와 R3가 함께는 피리딘환에 축합된 벤젠환을 형성할 수도 있으며; R4는 수소 또는 저급 알킬이고; R5는 수소이거나, R2와 R3가 수소인 경우에 R4와 R5가 함께는 피리딘 환에 축합된 벤젠환을 형성할 수도 있으며; Z, Z1, Z2, Z3및 Z4는 각각 독립적으로 수소, 저급 알킬, 페닐, 저급 알콕시, 알킬렌 또는 알콕시 알킬렌을 나타내거나, Z와 Z1또는 Z3와 Z4가 함께 산소 또는 황을 나타낼 수도 있다.Provided that when Y represents a heterocyclic group of formula (a) and A is CR, then R and R 1 together form a substituted or unsubstituted benzene ring or R 2 and R 3 together form a pyridine ring To form a condensed benzene ring; R 2 is hydrogen or lower alkyl, R 3 is hydrogen, lower alkoxy, halogen-substituted lower alkoxy, or substituted or unsubstituted benzyloxy, or R 2 and R 3 together form a benzene ring condensed on a pyridine ring. May form; R 4 is hydrogen or lower alkyl; R 5 is hydrogen, or when R 2 and R 3 are hydrogen, R 4 and R 5 together may form a benzene ring condensed on a pyridine ring; Z, Z 1 , Z 2 , Z 3 and Z 4 each independently represent hydrogen, lower alkyl, phenyl, lower alkoxy, alkylene or alkoxy alkylene, or Z and Z 1 or Z 3 and Z 4 together represent oxygen Or sulfur.

Description

치환된 이미다졸 유도체 및 그의 제조방법Substituted imidazole derivatives and preparation method thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (20)

다음 일반식(Ⅰ)의 치환된 이미다졸 유도체 및 약제학적으로 허용되는 그의 염.Substituted imidazole derivatives of the general formula (I) and pharmaceutically acceptable salts thereof. 상기식에서, A는 CR 또는 질소원자이고; R은 수소, 저급 알킬 또는 저급 알콕시이며, R1은 수소, 저급 알킬 또는 저급 알콕시를 나타내거나, R과 R1이 함께는 치환되거나 비치환된 벤젠환을 형성할 수도 있으며; Y는 일반식(a) 또는 (b)의 치환된 헤테로사이클릭 그룹이고,Wherein A is CR or a nitrogen atom; R is hydrogen, lower alkyl or lower alkoxy, R 1 represents hydrogen, lower alkyl or lower alkoxy, or R and R 1 may together form a substituted or unsubstituted benzene ring; Y is a substituted heterocyclic group of formula (a) or (b), 단, 여기에서 Y가 일반식(a)의 헤테로사이클릭 그룹을 나타내고 A가 CR인 경우에는, R과 R1이 함께 치환되거나 비치환된 벤젠환을 형성하거나 R2와 R3가 함께 피리딘환에 축합된 벤젠환을 형성하여야 하며; R2는 수소 또는 저급 알킬이고, R3는 수소, 저급 알콕시, 할로겐-치환된 저급 알콕시, 또는 치환되거나 비치환된 벤질옥시이거나, R2와 R3가 함께는 피리딘환에 축합된 벤젠환을 형성할 수도 있으며; R4는 수소 또는 저급 알킬이고; R5는 수소이거나, R2와 R3가 수소인 경우에 R4와 R5가 함께는 피리딘 환에 축합된 벤젠환을 형성할 수도 있으며; Z Z1, Z2, Z3및 Z4는 각각 독립적으로 수소, 저급 알킬, 페닐, 저급 알콕시, 알킬렌 또는 알콕시 알킬렌을 나타내거나, Z와 Z1또는 Z3와 Z4가 함께는 산소 또는 황을 나타낼 수도 있다.Provided that when Y represents a heterocyclic group of formula (a) and A is CR, then R and R 1 together form a substituted or unsubstituted benzene ring or R 2 and R 3 together form a pyridine ring To form a condensed benzene ring; R 2 is hydrogen or lower alkyl, R 3 is hydrogen, lower alkoxy, halogen-substituted lower alkoxy, or substituted or unsubstituted benzyloxy, or R 2 and R 3 together form a benzene ring condensed on a pyridine ring. May form; R 4 is hydrogen or lower alkyl; R 5 is hydrogen, or when R 2 and R 3 are hydrogen, R 4 and R 5 together may form a benzene ring condensed on a pyridine ring; ZZ 1 , Z 2 , Z 3 and Z 4 each independently represent hydrogen, lower alkyl, phenyl, lower alkoxy, alkylene or alkoxy alkylene, or Z and Z 1 or Z 3 and Z 4 together represent oxygen or It may represent sulfur. 제1항에 있어서, 다음 일반식(Ⅰ-a)로 표시되는 치환된 이미다졸 유도체.The substituted imidazole derivative according to claim 1, represented by the following general formula (I-a). 상기 식에서, Y는 일반식(a) 또는 (b)의 치환된 헤테로사이클릭 그룹을 나타내고;Wherein Y represents a substituted heterocyclic group of formula (a) or (b); R2는 수소 또는 저급 알킬이고, R3는 수소, 저급 알콕시, 할로겐-치환된 저급 알콕시, 또는 치환되거나 비치환된 벤질옥시이거나, R2와 R3가 함께는 피리딘환에 축합된 벤젠환을 형성할 수도 있으며; R4는 수소 또는 저급 알킬이고; R5는 수소이거나, R2와 R3가 수소인 경우에 R4와 R5가 함께는 피리딘환에 축합된 벤젠환을 형성할 수도 있으며, Z, Z1, Z2, Z3및 Z4는각각 독립적으로 수소, 저급 알킬, 페닐, 저급 알콕시, 알킬렌 또는 알콕시 알킬렌을 나타내거나, Z와 Z1또는 Z3와 Z4가 함께는 산소 또는 황을 나타낼 수도 있다.R 2 is hydrogen or lower alkyl, R 3 is hydrogen, lower alkoxy, halogen-substituted lower alkoxy, or substituted or unsubstituted benzyloxy, or R 2 and R 3 together form a benzene ring condensed on a pyridine ring. May form; R 4 is hydrogen or lower alkyl; R 5 is hydrogen or when R 2 and R 3 are hydrogen, R 4 and R 5 together may form a benzene ring condensed on a pyridine ring, and Z, Z 1 , Z 2 , Z 3 and Z 4 May independently represent hydrogen, lower alkyl, phenyl, lower alkoxy, alkylene or alkoxy alkylene, or Z and Z 1 or Z 3 and Z 4 together may represent oxygen or sulfur. 제1항에 있어서, 다음 일반식(Ⅰ-b)로 표시되는 치환된 이미다졸 유도체.The substituted imidazole derivative according to claim 1, represented by the following general formula (I-b). 상기 식에서, R1은 수소, 저급 알킬 또는 저급 알콕시를 나타내며; Y는 일반식(a) 또는 (b)의 치환된 헤테로사이클릭 그룹을 나타내고;Wherein R 1 represents hydrogen, lower alkyl or lower alkoxy; Y represents a substituted heterocyclic group of formula (a) or (b); R2는 수소 또는 저급 알킬이고, R3는 수소, 저급 알콕시, 할로겐-치환된 저급 알콕시, 또는 치환되거나 비치환된 벤질옥시이거나, R2와 R3가 함께는 피리딘환에 축합된 벤젠환을 형성할 수도 있으며; R4는 수소 또는 저급 알킬이고; R5는 수소이거나, R2와 R3가 수소인 경우에 R4와 R5가 함께는 피리딘환에 축합된 벤젠환을 형성할 수도 있으며; Z, Z1, Z2, Z3및 Z4는 각각 독립적으로 수소, 저급 알킬, 페닐, 저급 알콕시, 알킬렌 또는 알콕시 알킬렌을 나타내거나, Z와 Z1또는 Z3와 Z4가 함께는 산소 또는 황을 나타낼 수도 있다.R 2 is hydrogen or lower alkyl, R 3 is hydrogen, lower alkoxy, halogen-substituted lower alkoxy, or substituted or unsubstituted benzyloxy, or R 2 and R 3 together form a benzene ring condensed on a pyridine ring. May form; R 4 is hydrogen or lower alkyl; R 5 is hydrogen, or when R 2 and R 3 are hydrogen, R 4 and R 5 together may form a benzene ring condensed on a pyridine ring; Z, Z 1 , Z 2 , Z 3 and Z 4 each independently represent hydrogen, lower alkyl, phenyl, lower alkoxy, alkylene or alkoxy alkylene, or Z and Z 1 or Z 3 and Z 4 together It may represent oxygen or sulfur. 제1항에 있어서, 다음 일반식(Ⅰ-c)로 표시되는 치환된 이미다졸 유도체.The substituted imidazole derivative according to claim 1, represented by the following general formula (I-c). 상기 식에서, A는 CR 또는 질소원자이고; R은 수소, 저급 알킬 또는 저급 알콕시이며, R1은 수소, 저급 알킬 또는 저급 알콕시를 나타내거나, R과 R1이 함께는 치환되거나 비치환된 벤젠환을 형성할 수도 있으며; Z, Z1, Z2, Z3및 Z4는 각각 독립적으로 수소, 저급 알킬, 페닐, 저급 알콕시, 알킬렌 또는 알콕시 알킬렌을 나타내거나, Z와 Z1또는 Z3와 Z4가 함께는 산소 또는 황을 나타낼 수도 있다.Wherein A is CR or a nitrogen atom; R is hydrogen, lower alkyl or lower alkoxy, R 1 represents hydrogen, lower alkyl or lower alkoxy, or R and R 1 may together form a substituted or unsubstituted benzene ring; Z, Z 1 , Z 2 , Z 3 and Z 4 each independently represent hydrogen, lower alkyl, phenyl, lower alkoxy, alkylene or alkoxy alkylene, or Z and Z 1 or Z 3 and Z 4 together It may represent oxygen or sulfur. 제2항에 있어서, R2가 메틸이고, R3는 트리할로게노에톡시 또는 할로겐-치환된 벤질옥시이며, R4및 R5는 각각 수소인 일반식(Ⅰ-a)의 치환된 이미다졸 유도체. 3. The substituted image of formula (I-a) according to claim 2, wherein R 2 is methyl, R 3 is trihalogenoethoxy or halogen-substituted benzyloxy, and R 4 and R 5 are each hydrogen. Dazole Derivatives. 제5항에 있어서, 2-[[[3-메틸-4-(2,2,2-트리플루오로메톡시)-2-피리디닐]메틸]설피닐]-1H-나프트[2,3-d]이미다졸인 일반식(Ⅰ-a)의 치환된 이미다졸 유도체.The compound of claim 5, wherein 2-[[[3-methyl-4- (2,2,2-trifluoromethoxy) -2-pyridinyl] methyl] sulfinyl] -1H-naphth [2,3- d] Substituted imidazole derivatives of general formula (I-a) which are imidazoles. 제5항에 있어서, 2-[[[3-메틸-4-(4-플루오로벤질옥시)-3-피리디닐]메틸]설피닐]-1H-나프트[2,3-d]이미다졸인 일반식(Ⅰ-a)의 치환된 이미다졸 유도체.The compound of claim 5, wherein 2-[[[3-methyl-4- (4-fluorobenzyloxy) -3-pyridinyl] methyl] sulfinyl] -1H-naphth [2,3-d] imida Substituted imidazole derivatives of general formula (I-a). 제4항에 있어서, 5-메톡시-2[[(2-옥사졸리디논-4-일)메틸]설피닐]-1H-벤조이미다졸인 일반식(Ⅰ-c)의 치환된 벤즈이미다졸 유도체.The substituted benzimidazole of formula (I-c) according to claim 4, which is 5-methoxy-2 [[(2-oxazolidinon-4-yl) methyl] sulfinyl] -1 H-benzoimidazole. derivative. 제3항에 있어서, 2-[[(3,5-디메틸-4-메톡시-2-피리디닐)메틸]설피닐]-1H-이미다졸[4,5-c]피리딘인 일반식(Ⅰ-b)의 치환된 이미다졸 유도체.The general formula (I) according to claim 3, which is 2-[[(3,5-dimethyl-4-methoxy-2-pyridinyl) methyl] sulfinyl] -1H-imidazole [4,5-c] pyridine substituted imidazole derivatives of -b). 제1단계에서, 일반식(Ⅱ)의 디아미노 화합물을 티올 그룹을 제공하는 환 형성제와 반응시킨 후, 산성화하여 일반식(Ⅲ)의 이미다졸 화합물을 형성시키고; 제2단계에서는, 생성된 일반식(Ⅲ)의 화합물을 일반식 XCH2Y의 화합물과 반응시켜 일반식(Ⅳ)의 설파이드 화합물을 제조하고; 제3단계에서, 일반식(Ⅳ)의 설파이드 화합물을 산화시킴을 특징으로 하여, 일반식(Ⅰ)의 치환된 이미다졸 유도체 및 약제학적으로 허용되는 그의 염을 제조하는 방법.In a first step, the diamino compound of formula (II) is reacted with a ring former which provides a thiol group and then acidified to form an imidazole compound of formula (III); In the second step, the resulting compound of formula (III) is reacted with a compound of formula XCH 2 Y to prepare a sulfide compound of formula (IV); In a third step, a method of preparing a substituted imidazole derivative of formula (I) and a pharmaceutically acceptable salt thereof, characterized by oxidizing a sulfide compound of formula (IV). 상기 식에서, A는 CR 또는 질소원자이고; R은 수소, 저급 알킬 또는 저급 알콕시이며, R1은 수소, 저급 알킬 또는 저급 알콕시를 나타내거나, R과 R1이 함께는 치환되거나 비치환된 벤젠환을 형성할 수도 있으며; Y는 일반식(a) 또는 (b)의 치환된 헤테로사이클릭 그룹이고,Wherein A is CR or a nitrogen atom; R is hydrogen, lower alkyl or lower alkoxy, R 1 represents hydrogen, lower alkyl or lower alkoxy, or R and R 1 may together form a substituted or unsubstituted benzene ring; Y is a substituted heterocyclic group of formula (a) or (b), 단, 여기에서 Y가 일반식(a)의 헤테로사이클릭 그룹을 나타내고 A가 CR인 경우에는 R과 R1이 함께는 치환되거나 비치환된 벤젠환을 형성하거나 R2와 R3가 함께 피리딘환에 축합된 벤젠환을 형성하여야 하며; R2는 수소 또는 저급 알킬이고, R3는 수소, 저급 알콕시, 할로겐-치환된 저급 알콕시, 또는 치환되거나 비치환된 벤질옥시이거나, R2와 R3가 함께는 피리딘환에 축합된 벤젠환을 형성할 수도 있으며; R4는 수소 또는 저급 알킬이고; R5는 수소이거나, R2와 R3가 수소인 경우에 R4와 R5가 함께는 피리딘 환에 축합된 벤젠환을 형성할 수도 있으며; Z, Z1, Z2, Z3및 Z4는 각각 독립적으로 수소, 저급 알킬, 페닐, 저급 알콕시, 알킬렌 또는 알콕시 알킬렌을 나타내거나, Z와 Z1또는 Z3와 Z4가 함께는 산소 또는 황을 나타낼 수도 있고; X는 할로겐 원자를 나타낸다.Provided that when Y represents a heterocyclic group of formula (a) and A is CR, then R and R 1 together form a substituted or unsubstituted benzene ring, or R 2 and R 3 together form a pyridine ring To form a condensed benzene ring; R 2 is hydrogen or lower alkyl, R 3 is hydrogen, lower alkoxy, halogen-substituted lower alkoxy, or substituted or unsubstituted benzyloxy, or R 2 and R 3 together form a benzene ring condensed on a pyridine ring. May form; R 4 is hydrogen or lower alkyl; R 5 is hydrogen, or when R 2 and R 3 are hydrogen, R 4 and R 5 together may form a benzene ring condensed on a pyridine ring; Z, Z 1 , Z 2 , Z 3 and Z 4 each independently represent hydrogen, lower alkyl, phenyl, lower alkoxy, alkylene or alkoxy alkylene, or Z and Z 1 or Z 3 and Z 4 together May represent oxygen or sulfur; X represents a halogen atom. 제10항에 있어서, 제1단계에서 일반식(Ⅱ) 화합물의 환형성제로 수산화 칼륨 존재하에서 이황화탄소를 사용하는 방법.The method according to claim 10, wherein in the first step, carbon disulfide is used in the presence of potassium hydroxide as a ring forming agent of the compound of formula (II). 제10항에 있어서, 제1단계에서 일반식(Ⅱ) 화합물의 환형성제로 o-에틸크산트산 칼륨염을 사용하는 방법.The method according to claim 10, wherein in the first step, o-ethyl xanthate potassium salt is used as the ring-forming agent of the compound of formula (II). 제10항 내지 12항중의 어느 하나에 있어서, 제1단계에서 산성화제로 아세트산을 사용하는 방법.The process according to claim 10, wherein acetic acid is used as the acidifying agent in the first step. 제10항에 있어서, 제2단계 반응을 염기의 존재하에 수행하는 방법.The method of claim 10, wherein the second stage reaction is carried out in the presence of a base. 제14항에 있어서, 염기가 수산화나트륨인 방법.The method of claim 14, wherein the base is sodium hydroxide. 제10항 및 14항 내지 15항중의 어느 하나에 있어서, 제2단계 반응을 알콜용매 또는 알콜과 물의 혼합용매중에서 수행하는 방법.The process according to any one of claims 10 and 14 to 15, wherein the second stage reaction is carried out in an alcoholic solvent or a mixed solvent of alcohol and water. 제10항에 있어서, 제3단계에서 산화제로 m-클로로퍼옥시벤조산 또는 과산화수소를 사용하는 방법.The method of claim 10, wherein m-chloroperoxybenzoic acid or hydrogen peroxide is used as the oxidizing agent in the third step. 제1항 내지 9항중의 어느 하나에 따른 화합물 및 약제학적으로 허용되는 담체를 함유함을 특징으로 하는 약제학적 조성물.A pharmaceutical composition comprising a compound according to any one of claims 1 to 9 and a pharmaceutically acceptable carrier. 제1항 내지 9항중의 어느 하나에 따른 화합물의 위궤양 치료제로서의 용도.Use of a compound according to any one of claims 1 to 9 as a therapeutic agent for gastric ulcer. 위산분비를 억제시킬 필요가 있는 포유동물에게 제1항 내지 9항중의 어느 하나에 따른 화합물을 투여함을 특징으로 하여, 위궤양을 치료 또는 예방하는 방법.A method for treating or preventing gastric ulcer, characterized by administering the compound according to any one of claims 1 to 9 to a mammal in need of suppressing gastric acid secretion. ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.※ Note: This is to be disclosed by the original application.
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