KR960014106A - Novel antiviral 1-alkyl-2,4-pyrimidinedione derivatives and preparation methods thereof - Google Patents

Novel antiviral 1-alkyl-2,4-pyrimidinedione derivatives and preparation methods thereof Download PDF

Info

Publication number
KR960014106A
KR960014106A KR1019940026784A KR19940026784A KR960014106A KR 960014106 A KR960014106 A KR 960014106A KR 1019940026784 A KR1019940026784 A KR 1019940026784A KR 19940026784 A KR19940026784 A KR 19940026784A KR 960014106 A KR960014106 A KR 960014106A
Authority
KR
South Korea
Prior art keywords
group
compound
substituted
atom
ethyl
Prior art date
Application number
KR1019940026784A
Other languages
Korean (ko)
Other versions
KR0180581B1 (en
Inventor
손종찬
이일영
이화자
채영복
Original Assignee
강박광
재단법인 한국화학연구소
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 강박광, 재단법인 한국화학연구소 filed Critical 강박광
Priority to KR1019940026784A priority Critical patent/KR0180581B1/en
Publication of KR960014106A publication Critical patent/KR960014106A/en
Application granted granted Critical
Publication of KR0180581B1 publication Critical patent/KR0180581B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

본 발명은 항바이러스제로서, 특히 후천성 면역결핍증(AIDS)치료에 유용한, 하기 일반식(I)의 신규의 2,4-피리미딘디온의 유도체 및 R의 염에 관한 것이다.The present invention relates to novel derivatives of 2,4-pyrimidinedione of formula (I) and salts of R, which are particularly useful as antiviral agents for the treatment of acquired immunodeficiency syndrome (AIDS).

상기식에서, R1, 및 R2는 각각 독립적으로 수소원자; 할로겐 원자; 히드록시기, C1-C10의 카르보닐옥시기, 아지도기, 시아노기, 할로겐 원자, 페닐기, C3-C10의 헤테로아릴기, C1-C10이 알콕시기 또는 벤질옥시기로 치환되거나 치환되지 않은 C1-C10의 알킬기; 히드록시기, 아지도기, 시아노기, 할로겐 원자, 페닐기, C3-C8의 헤테로아릴기, C1-C10이 알콕시기 또는 벤질옥시기로 치환되거나 치환되지 않은 C2-C6의 알킬기; 아지도기, 시아노기, 불소, 페닐기 또는 C3-C10이 헤테로알릴기로 치환되거나 치환되지 않은 C3-C10의 시클로알킬기; 할로겐원자, C1-C10의 알킬기, 히드록시기, C1-C10이 알콕시기, 아지도기, 시아노기, C1-C10의 알콕시카르보닐기 또는 C1-C10의 카르바모일기로 치환되거나 치환되지 않은 아릴기; 할로겐원자, C1-C10의 알킬기, C1-C10이 알콕시기, 아미노기, 니트로기, 시아노기, C1-C10의 알콕시카르보닐기 또는 C1-C10의 카르바모일기로 치환되거나 치환되지 않은 C3-C20이 헤테로알릴기; C2-C20의 알콕시카르보닐기 또는 C1-C10의 카르바모일를 나타내며, R3는 할로겐 C1-C10의 알킬기, C3-C10의 시클로알킬기, C2-C10의 알케닐기, C2-C8의 아키닐기 또는 벤질기를 나타내며, R4, R5는 각각 독립적으로 수소원자, 할로겐원자, 히드록시기, C1-C10의 알킬기, 불소화메틸기, C1-C10이 알콕시기, 아미노기, 니트로기, 시아노기, C2-C8의 알콕시카르보닐기 또는 C1-C8의 카르바모일기를 나타내며, A는 산소원자 또는 황원자를 나타내며, Z는 산소 원자; 황원자; 메틸렌기 또는 카르보닐기를 나타낸다.In the above formula, R 1 and R 2 are each independently a hydrogen atom; Halogen atom; Hydroxy group, C 1 -C 10 carbonyloxy group, azido group, cyano group, halogen atom, phenyl group, C 3 -C 10 heteroaryl group, C 1 -C 10 is not substituted or substituted with an alkoxy group or benzyloxy group Unsubstituted C 1 -C 10 alkyl groups; Hydroxy group, azido group, cyano group, halogen atom, phenyl group, C 3 -C 8 heteroaryl group, C 2 -C 6 alkyl group wherein C 1 -C 10 is unsubstituted or substituted with an alkoxy group or benzyloxy group; A C 3 -C 10 cycloalkyl group with or without an azido group, cyano group, fluorine, phenyl group or C 3 -C 10 substituted with a heteroallyl group; An alkyl group of a halogen atom, C 1 -C 10, hydroxy, C 1 -C 10 alkoxy group, an azido group, a cyano group, a carbamoyl group substituted with a C 1 -C 10 alkoxy group or a C 1 -C 10 or a substituted Unsubstituted aryl group; Halogen atom, C 1 -C 10 alkyl group, C 1 -C 10 is substituted or substituted with an alkoxy group, amino group, nitro group, cyano group, C 1 -C 10 alkoxycarbonyl group or C 1 -C 10 carbamoyl group Unsubstituted C 3 -C 20 heteroaryl group; C 2 -C 20 alkoxycarbonyl group or C 1 -C 10 carbamoyl, R 3 is a halogen C 1 -C 10 alkyl group, C 3 -C 10 cycloalkyl group, C 2 -C 10 alkenyl group, represents an architecture of a benzyl group or a C 2 -C 8, R 4, R 5 are each independently a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group of C 1 -C 10, a fluorinated methyl group, C 1 -C 10 alkoxy group, Amino group, nitro group, cyano group, C 2 -C 8 alkoxycarbonyl group or C 1 -C 8 carbamoyl group, A represents an oxygen atom or a sulfur atom, Z represents an oxygen atom; Sulfur atom; Methylene group or carbonyl group is represented.

Description

신규한 항바이러스성 1-알킬-2,4-피리미딘디온 유도체 및 그의 제조방법.Novel antiviral 1-alkyl-2,4-pyrimidinedione derivatives and methods for their preparation.

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

Claims (10)

하기 일반식(I)의 화합물 또는 그의 약제학적으로 허용가능한 염 :A compound of formula (I) or a pharmaceutically acceptable salt thereof: 상기식에서, R1, 및 R2는 각각 독립적으로 수소원자; 할로겐 원자; 히드록시기, C1-C10의 카르보닐옥시기, 아지도기, 시아노기, 할로겐 원자, 페닐기, C3-C10의 헤테로아릴기, C1-C10이 알콕시기 또는 벤질옥시기로 치환되거나 치환되지 않은 C1-C10의 알킬기; 히드록시기, 아지도기, 시아노기, 할로겐 원자, 페닐기, C3-C8의 헤테로아릴기, C1-C10이 알콕시기 또는 벤질옥시기로 치환되거나 치환되지 않은 C2-C6의 알킬기; 아지도기, 시아노기, 불소, 페닐기 또는 C3-C10이 헤테로알릴기로 치환되거나 치환되지 않은 C3-C10의 시클로알킬기; 할로겐원자, C1-C10의 알킬기, 히드록시기, C1-C10이 알콕시기, 아지도기, 시아노기, C1-C10의 알콕시카르보닐기 또는 C1-C10의 카르바모일기로 치환되거나 치환되지 않은 알킬기; 할로겐원자, C1-C10의 알킬기, C1-C10이 알콕시기, 아미노기, 니트로기, 시아노기, C1-C10의 알콕시카르보닐기 또는 C1-C10의 카르바모일기로 치환되거나 치환되지 않은 C3-C20이 헤테로알릴기; C2-C20의 알콕시카르보닐기 또는 C1-C10의 카르바모일를 나타내며, R3는 할로겐 C1-C10의 알킬기, C3-C10의 시클로알킬기, C2-C10의 알케닐기, C2-C8의 알케닐기 또는 벤질기를 나타내며, R4, R5는 각각 독립적으로 수소원자, 할로겐원자, 히드록시기, C1-C10의 알킬기, 불소화메틸기, C1-C10이 알콕시기, 아미노기, 니트로기, 시아노기, C2-C8의 알콕시카르보닐기 또는 C1-C8의 카르바모일기를 나타내며, A는 산소원자 또는 황원자를 나타내며, Z는 산소 원자; 황원자; 메틸렌기 또는 카르보닐기를 나타낸다.In the above formula, R 1 and R 2 are each independently a hydrogen atom; Halogen atom; Hydroxy group, C 1 -C 10 carbonyloxy group, azido group, cyano group, halogen atom, phenyl group, C 3 -C 10 heteroaryl group, C 1 -C 10 is not substituted or substituted with an alkoxy group or benzyloxy group Unsubstituted C 1 -C 10 alkyl groups; Hydroxy group, azido group, cyano group, halogen atom, phenyl group, C 3 -C 8 heteroaryl group, C 2 -C 6 alkyl group wherein C 1 -C 10 is unsubstituted or substituted with an alkoxy group or benzyloxy group; A C 3 -C 10 cycloalkyl group with or without an azido group, cyano group, fluorine, phenyl group or C 3 -C 10 substituted with a heteroallyl group; An alkyl group of a halogen atom, C 1 -C 10, hydroxy, C 1 -C 10 alkoxy group, an azido group, a cyano group, a carbamoyl group substituted with a C 1 -C 10 alkoxy group or a C 1 -C 10 or a substituted Unsubstituted alkyl groups; Halogen atom, C 1 -C 10 alkyl group, C 1 -C 10 is substituted or substituted with an alkoxy group, amino group, nitro group, cyano group, C 1 -C 10 alkoxycarbonyl group or C 1 -C 10 carbamoyl group Unsubstituted C 3 -C 20 heteroaryl group; C 2 -C 20 alkoxycarbonyl group or C 1 -C 10 carbamoyl, R 3 is a halogen C 1 -C 10 alkyl group, C 3 -C 10 cycloalkyl group, C 2 -C 10 alkenyl group, represents an alkenyl group or a benzyl C 2 -C 8, R 4, R 5 are each independently a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group of C 1 -C 10, a fluorinated methyl group, C 1 -C 10 alkoxy group, Amino group, nitro group, cyano group, C 2 -C 8 alkoxycarbonyl group or C 1 -C 8 carbamoyl group, A represents an oxygen atom or a sulfur atom, Z represents an oxygen atom; Sulfur atom; Methylene group or carbonyl group is represented. 제1항에 있어서, R1및 R2가 각각 독립적으로 수소원자 : 히드록시기, C1-C10의 카르보닐옥시기, 아지도기, 시아노기, 할로겐 원자, 페닐기, C1-C10이 알콕시기 또는 벤질옥시기로 치환되거나 치환되지 않은 C1-C10의 알킬기; 할로겐원자, C3-C6의 알킬기, 히드록시기, C1-C4이 알콕시기, 아지도기, 시아노기, C2-C8의 알콕시카르보닐기 또는 C1-C8의 카르바모일기로 치환되거나 치환되지 않은 페닐기; C3-C10이 헤테로알릴기; C2-C20의 알콕시카르보닐기; 또는 C1-C10의 카르바모일를 나타내며, R3가 C1-C6의 알킬기, C3-C10의 시클로알킬기, C2-C10의 알케닐기, C2-C8의 알케닐기 또는 벤질기를 나타내며, R4, R5는 각각 독립적으로 수소원자, 할로겐원자, 히드록시기, C1-C4의 알킬기, C1-C4이 알콕시기, 아미노기, C2-C5의 알콕시카르보닐기, 불소메틸기 또는 C1-C3의 카르바모일를 나타내며, A가 산소원자 또는 황원자를 나타내며, Z가 산소원자, 황원자, 메틸렌기 또는 카르보닐기를 나타내는 일반식(I)의 화합물 또는 그의 약제학적으로 허용가능한 염.The R 1 and R 2 are each independently a hydrogen atom: a hydroxyl group, a C 1 -C 10 carbonyloxy group, an azido group, a cyano group, a halogen atom, a phenyl group, a C 1 -C 10 alkoxy group Or a C 1 -C 10 alkyl group unsubstituted or substituted with a benzyloxy group; Halogen atom, C 3 -C 6 alkyl group, hydroxy group, C 1 -C 4 is substituted or substituted with alkoxy group, azido group, cyano group, C 2 -C 8 alkoxycarbonyl group or C 1 -C 8 carbamoyl group Unsubstituted phenyl group; C 3 -C 10 is a heteroallyl group; C 2 -C 20 alkoxycarbonyl group; Or represents C 1 -C 10 aliphatic carboxylic acid of moilreul, R 3 is C 1 -C 6 alkyl group of, C 3 -C 10 cycloalkyl group, C 2 -C 10 alkenyl group, C 2 -C 8 alkenyl group or A benzyl group, R 4 and R 5 each independently represent a hydrogen atom, a halogen atom, a hydroxy group, a C 1 -C 4 alkyl group, a C 1 -C 4 alkoxy group, an amino group, a C 2 -C 5 alkoxycarbonyl group, and fluorine A compound of formula (I) or a pharmaceutically acceptable salt thereof, which represents a methyl group or carbamoyl of C 1 -C 3 , A represents an oxygen atom or a sulfur atom, and Z represents an oxygen atom, a sulfur atom, a methylene group or a carbonyl group . 제1항에 있어서, R1및 R2가 각각 독립적으로 수소원자, 메틸기, 히드록시메틸기, C2-C8의 카르보닐옥시기, 할로겐화 메틸기, 아지도 메틸기, C2-C6의 알킬기, C2-C10의 알케닐기. C3-C6의 시클로알킬리, 페닐기, C1-C10의 알콕시카르보닐기 또는 C1-C10의 카르바 보닐기를 나타내며, R3가, 에틸기 또는 이소프로필기를 나타내며, R4, R5는 각각 독립적으로 수소원자, 염소원자, 메틸기, 에틸기, 이소프로필기, C1-C3의 알콕시기를 나타내며, A가 산소원자를 나타내며, Z는 황원자, 산소원자, 메틸렌기 또는 카르보닐기를 나타내는 일반식(I)의 화합물 또는 그의 약제학적으로 허용가능한 염.2. A compound according to claim 1, wherein R 1 and R 2 are each independently a hydrogen atom, a methyl group, a hydroxymethyl group, a C 2 -C 8 carbonyloxy group, a halogenated methyl group, an azido methyl group, a C 2 -C 6 alkyl group, Alkenyl group of C 2 -C 10 . C 3 -C 6 cycloalkyli, phenyl group, C 1 -C 10 alkoxycarbonyl group or C 1 -C 10 carbacarbonyl group, R 3 represents an ethyl group or isopropyl group, R 4 , R 5 is Each independently represent a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, an isopropyl group, a C 1 -C 3 alkoxy group, A represents an oxygen atom, and Z represents a sulfur atom, an oxygen atom, a methylene group or a carbonyl group ( A compound of I) or a pharmaceutically acceptable salt thereof. 제1항에 있어서, 1-n-부틸-5-에틸-6-(3.5-디메틸페리오)-2,4-피리미디온; 1-(3-페닐-n-프로필)-5-에틸-6-(3.5-디메틸페리오)2,4-피리미디온; 1-n-부틸-5-에틸-6(3.5-디메틸벤조일)-2,4-피리미디온; 1-(3-패닐-n-프로필)-5-에틸-6-(3.5-디메틸벤조일)-2.4-피리미딘디온; 1-n-펜틸-5-에틸-6-(3.5-디메틸벤조일)-2,4-피리미디온; 1-(3-메틸-n-부틸)-5-에틸-6-(3.5-디메틸벤조일)-2,4-피리미디온; 1-n-프로필-5에틸-6-(3.5-디메틸벤조일)-2,4-피리미디온;1-(3-메톡시카르보닐-n-프로필)-5에틸-6-(3.5-디메틸벤조일)-2.4-피리미딘디온; 1-n-부틸-5-이소프로필-6-(3,5-디메틸벤조일)-2.4-피리미딘디온; 1-(3-페닐-n-프로필)-5-에틸-6-(3,5-디메틸벤조일)-2.4-피리미딘디온; 1-n-부틸-5-에틸-6-(3,5-디메틸벤질)-2.4-피리미딘디온; 1-n-프로필-5-에틸-6-(3,5-디메틱페녹시)-2.4-피리미딘디온; 1-n-부틸-5-에틸-6-(3,5-디메틸페녹시)-2.4-피리미딘디온; 1-(3-페닐-n-프로필)-5-에틸-6-(3,5-디메틸페녹시)-2.4-피리미딘디온; 1-(4-히드록시-n-부틸)-5에틸6-6(3,5-디메틸페녹시)-2.4-피리미딘디온; 1-n-부틸5-이소프로필-6-(3,5-디메틸페녹시)-2.4-피리미딘디온; 1-(3-페닐-n-프로필)-5-이소프로필-6-(3,5-디메틸페녹시)-2.4-피리미딘디온; 및 1-(4-펜테닐)-5-에틸-6-(3,5-디메틸벤조일)-2.4-피리미딘디온으로 이루어진 군중에서 선택된 일반식(I) 화합물 및 그의 약제학적으로 허용가능한 염.The compound of claim 1, further comprising 1-n-butyl-5-ethyl-6- (3.5-dimethylperio) -2,4-pyrimidion; 1- (3-phenyl-n-propyl) -5-ethyl-6- (3.5-dimethylperio) 2,4-pyrimidione; 1-n-butyl-5-ethyl-6 (3.5-dimethylbenzoyl) -2,4-pyrimidinone; 1- (3-Fanyl-n-propyl) -5-ethyl-6- (3.5-dimethylbenzoyl) -2.4-pyrimidinedione; 1-n-pentyl-5-ethyl-6- (3.5-dimethylbenzoyl) -2,4-pyrimidione; 1- (3-methyl-n-butyl) -5-ethyl-6- (3.5-dimethylbenzoyl) -2,4-pyrimidione; 1-n-propyl-5ethyl-6- (3.5-dimethylbenzoyl) -2,4-pyrimidion; 1- (3-methoxycarbonyl-n-propyl) -5ethyl-6- (3.5-dimethyl Benzoyl) -2.4-pyrimidinedione; 1-n-butyl-5-isopropyl-6- (3,5-dimethylbenzoyl) -2.4-pyrimidinedione; 1- (3-phenyl-n-propyl) -5-ethyl-6- (3,5-dimethylbenzoyl) -2.4-pyrimidinedione; 1-n-butyl-5-ethyl-6- (3,5-dimethylbenzyl) -2.4-pyrimidinedione; 1-n-propyl-5-ethyl-6- (3,5-dimaticphenoxy) -2.4-pyrimidinedione; 1-n-butyl-5-ethyl-6- (3,5-dimethylphenoxy) -2.4-pyrimidinedione; 1- (3-phenyl-n-propyl) -5-ethyl-6- (3,5-dimethylphenoxy) -2.4-pyrimidinedione; 1- (4-hydroxy-n-butyl) -5ethyl6-6 (3,5-dimethylphenoxy) -2.4-pyrimidinedione; 1-n-butyl5-isopropyl-6- (3,5-dimethylphenoxy) -2.4-pyrimidinedione; 1- (3-phenyl-n-propyl) -5-isopropyl-6- (3,5-dimethylphenoxy) -2.4-pyrimidinedione; And 1- (4-pentenyl) -5-ethyl-6- (3,5-dimethylbenzoyl) -2.4-pyrimidinedione; and a pharmaceutically acceptable salt thereof. 하기 일반식(II)의 화합물과 하기 일반식(III)의 화합물을 반응시켜 하기 일반식(IV)의 화합물을 얻은 후 이를 수소 첨가 반응 시킴을 포함하는, 하기 일반식(I)의 화합물의 제조방법 :Preparation of a compound of the general formula (I) comprising reacting a compound of the general formula (II) with a compound of the general formula (III) to give a compound of the general formula (IV), followed by hydrogenation Way : 상기식에서, R1, R2, R3, R4, R5및 X는 제1항에서 정의한 바와 같고, X는 할로겐원자 또는 술로닐옥시기를 나타낸다.Wherein R 1 , R 2 , R 3 , R 4 , R 5 and X are as defined in claim 1, and X represents a halogen atom or a sulfonyloxy group. 제5항에 있어서, 상기 일반식(II)의 화합물과 상기 일반식(III)의 화합물을 염기 및 극성 용매중에서 상온에서 질소분위기하에 1 : 0.8 내지 1 : 1.2의 몰비로 반응시키는 방법.The method according to claim 5, wherein the compound of formula (II) and the compound of formula (III) are reacted in a molar ratio of 1: 0.8 to 1: 1.2 in a base and a polar solvent under a nitrogen atmosphere at room temperature. 제5항에 있어서, 상기 수소첨가 반응을 극성 용매 중에서 팔라듐 촉매를 존재하에 수행하는 방법.The process of claim 5 wherein said hydrogenation reaction is carried out in the presence of a palladium catalyst in a polar solvent. 하기 일반식(IX)의 화합물과 하기 일반식(X)의 화합물을 반응시켜 하기 일반식(IV)의 화합물을 얻은 후, 이를 수소 첨가 반응 시킴을 포함하는, 하기 일반식(I)의 화합물의 제조방법 :Of a compound of formula (I) comprising reacting a compound of formula (IX) with a compound of formula (X) to give a compound of formula (IV), followed by a hydrogenation reaction Method of manufacture: 상기식에서, R1, R2, R3, R4, R5및 X는 제1항에서 정의한 바와 같다.Wherein R 1 , R 2 , R 3 , R 4 , R 5 and X are as defined in claim 1. 제8항에 있어서, 상기 일반식(IX)의 화합물과 상기 일반식(X)의 화합물을 극성 용매 및 염기의 존재하에서 80 내지 150℃ 범위의 온도에서 1 : 1 내지 2 : 1의 몰비로 환류반응시키는 방법.9. The compound of claim 8, wherein the compound of formula (IX) and the compound of formula (X) are refluxed at a molar ratio of 1: 1 to 2: 1 at a temperature ranging from 80 to 150 ° C in the presence of a polar solvent and a base. How to react. 제1항 내지 제4항 중 어느 한 항에 화합물 또는 그의 약학적으로 허용가능한 염의 항 바이러스 효과량 및 그의 약제학적으로 허용가능한 담체를 포함하는 약학 조성물.A pharmaceutical composition comprising an antiviral effective amount of a compound or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier thereof according to any one of claims 1 to 4. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940026784A 1994-10-20 1994-10-20 Novel anti-virus 1-alkyl-2,4-pyrimidion derivative KR0180581B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019940026784A KR0180581B1 (en) 1994-10-20 1994-10-20 Novel anti-virus 1-alkyl-2,4-pyrimidion derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019940026784A KR0180581B1 (en) 1994-10-20 1994-10-20 Novel anti-virus 1-alkyl-2,4-pyrimidion derivative

Publications (2)

Publication Number Publication Date
KR960014106A true KR960014106A (en) 1996-05-22
KR0180581B1 KR0180581B1 (en) 1999-03-20

Family

ID=19395461

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940026784A KR0180581B1 (en) 1994-10-20 1994-10-20 Novel anti-virus 1-alkyl-2,4-pyrimidion derivative

Country Status (1)

Country Link
KR (1) KR0180581B1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100390096B1 (en) * 1998-03-10 2003-08-19 한국화학연구원 Novel antiviral 2,4-pyrimidinedione derivatives substituted with alpha-substituted arylmethylene group at c-6 position
KR100368891B1 (en) * 1999-03-04 2003-01-24 한국화학연구원 Novel antiviral 2,4-pyrimidinedione derivatives

Also Published As

Publication number Publication date
KR0180581B1 (en) 1999-03-20

Similar Documents

Publication Publication Date Title
DE69115570D1 (en) UREIDO DERIVATIVES OF POLY-4-AMINO-2-CARBOXY-1-METHYL COMPOUNDS
KR870010045A (en) 4H-1-benzopyran-4-one derivative and preparation method thereof
FI944568A (en) Synthesis of oligonucleotides
DE60001811T2 (en) ANTI-FLAMMABLE INDOLDER DERIVATIVES
ITMI922006A1 (en) NITRIC ESTERS OF ACID DERIVATIVES 2- (2, 6-DI-HALO-PHENYLAMINE) PHENYLACETIC AND PROCEDURE FOR THEIR PREPARATION
KR940019708A (en) Heterocyclic substituted phenyl-cyclohexane-carboxylic acid derivative
DE60117963D1 (en) PROCESS FOR PRODUCING CITALOPRAM
KR950017971A (en) Novel antiviral 2,4-pyrimidinedione derivatives and preparation method thereof
KR960014106A (en) Novel antiviral 1-alkyl-2,4-pyrimidinedione derivatives and preparation methods thereof
KR930019634A (en) Imidazolyl substituted phenylacetamide
KR960031442A (en) Use of phenylcyclohexylcarboxamide
JPS56125347A (en) Preparation of dipeptide
HRP20010798B1 (en) Processes for preparing pesticidal intermediates
AR011126A1 (en) PROCEDURE FOR PREPARING EPROSARTANE AND INTERMEDIATE COMPOUNDS.
ATE203029T1 (en) ORGANIC POLYMER COMPOUND AND PRODUCTION THEREOF
KR900001655A (en) Method for preparing morniflumate and cognate compounds
SE443784B (en) NEW ASSOCIATIONS WITH PHARMACOLOGICAL EFFECT
KR970015583A (en) (S) -? - hydroxy -? - butyrolactone
KR910004632A (en) Novel 1-oxa-2-oxo-8-azaspiro [4,5] decane derivatives, pharmaceutical compositions comprising them and methods for preparing the same
JPH11217362A (en) Production of beta-hydrazinoesters, pyrazolidinones, and beta-amino acid derivative
ATE258187T1 (en) PREPARATION OF 2'-SUBSTITUTED RNA
DE69113851T2 (en) Process for the preparation of optically active norbornylamine derivatives.
JP3503993B2 (en) Method for producing N-mono-t-butyloxycarbonylalkylenediamine
KR950032144A (en) New preparation of antiviral 2,4-pyrimidinedione derivatives
RU2002118605A (en) Nitrosulfobenzamides

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20110915

Year of fee payment: 14

FPAY Annual fee payment

Payment date: 20121002

Year of fee payment: 15

LAPS Lapse due to unpaid annual fee