[go: up one dir, main page]

KR900701815A - 피리미딘 유도체 - Google Patents

피리미딘 유도체

Info

Publication number
KR900701815A
KR900701815A KR1019900700287A KR900700287A KR900701815A KR 900701815 A KR900701815 A KR 900701815A KR 1019900700287 A KR1019900700287 A KR 1019900700287A KR 900700287 A KR900700287 A KR 900700287A KR 900701815 A KR900701815 A KR 900701815A
Authority
KR
South Korea
Prior art keywords
derivative
hydrogen
formula
alkyl
compound
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
KR1019900700287A
Other languages
English (en)
Inventor
닐스 건나르 죠헨슨 케이
씨 지이 맘버그 핸즈
노린 롤프
크리스턴 샬버그 에스
디 숀 다니엘
그로노위츠 살로
Original Assignee
커트 리데
메디버 에이비이
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 커트 리데, 메디버 에이비이 filed Critical 커트 리데
Publication of KR900701815A publication Critical patent/KR900701815A/ko
Withdrawn legal-status Critical Current

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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

내용 없음

Description

피리미딘 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (25)

  1. 다음 구조식(I)로 표시되는 피리미딘 유도체와 약제학적으로 허용가능한 그의 염.
    상기식에서, 치환기 R1은 수산기 또는 NH2이고, R2는
    (여기서, X는 산소, 황, N-R7또는 세슘이고, R6은 수소, 직쇄 또는 분쇄형 C1-10알킬기, 불소, 염소, 브롬, 요오드, X-R7, -CH=CH-R7, -C≡C-R7, CO2R7, CH2X-R7이며, R7은 수소, 직쇄 또는 분쇄형 C1-10알킬기 또는 페닐이다.) R3는 수소, 0H, 불소 또는 OCH3이고 R4는 수소, 불소, 0H 혹은 그들의 에테르 또는 에스테르 잔기, OCH3CN, C≡CH 또는 N3이며, R5는 OH 혹은 다음 구조식으로 표시되는 화합물들의 헤테르 또느 에스테르 잔기이다.
    (여기서, n은 O 혹은 1이고, M은 수소, 또는 나트륨, 칼륨, 암모늄 혹은 알킬암모늄과 같은 약제학적으로 허용가능한 대이온이다.)
  2. 제1항에 있어서의 유도체의 α-아노머의 형태를 갖는 것을 특징으로 하는 유도체.
  3. 제l항에 있어서의 유도체는 β-아노머의 형태를 갖는 것을 특징으로 하는 유도체.
  4. 제2항 또는 제3항에 있어서, 탄수화물 부위는 아라비노푸라노즐 배열을 갖는것을 특징으로 하는 유도체.
  5. 제2항 또는 제3항에 있어서, 탄수화물 부위는 리모푸라노즐 배열을 갖는 것을 특징으로 하는 유도체.
  6. 제1항 내지 제5항중 어느 하나의 항에 있어서, R4과, R5는 모두 OH인 것을 특징으로 하는 유도체.
  7. 제1항 내지 제5항중 어느 하나의 항에 있어서, R3과, R4는 모두 수소인 것을 특징으로 하는 유도체.
  8. 제1항 내지 제5항중 어느 하나의 항에 있어서, R3는 수소이고, R4는 플루오로, 아지도, 시아노, 또는 메톡시인 것을 특징으로 하는 유도체.
  9. 제1항 내지 제5항중 어느 하나의 항에 있어서, R3는 수소이고, R4는 플루오로, 아지도, 시아노, 또는 메톡시인 것을 특징으로 하는 유도체.
  10. 제1항 내지 제5항중 어느 하나의 항에 있어서 R5는
    (여기서, n=O 혹은 1)인 것을 특징으로 하는 유도체.
  11. 제1항 내지 제5항중 어느 하나의 항에 있어서, 에테르잔기는 R5는 -0R8로서 정의되며, 이때 R8은 C1내지 C8의 알킬, 임의적으로는 하나이상의 알콕시, 아미노, 또는 술프아미도기나, 하나 이상의 할로겐원자로 치환된 아릴알킬인 것을 특징으로 하는 유도체.
  12. 제1항 내지 제5항중 어느 하나의 항에 있어서, 에스테르 잔기인 R4및/ 또는 R5는 카르복실산 R9COOH, 카르본산R10COOH, 카르본산의 더블에스테르 Rl0CO2CH(R11)OCO2H, 술폰산R10SO2OH, 카르바민산 R10NHCOOH 또는 인산(여기서, R9은 수소, C1내지 C17의 알킬, 알콕시알킬, 아릴알킬 혹은 아릴이며, R10은 C|1내지 C17의 알킬 아릴알킬 혹은 아릴이고, R11은 수소 혹은 C1내지 C3의 알킬로서, 상기 아릴과 아릴알킬기는 임의적으로는 하나 또는 그 이상의 알킬, 알콕시, 아미노, 니트릴 또는 술폰아미도기 또는 하나 또는그 이상의 할로겐원자 등으로 치환될 수도 있다.)으로 부터 유도된 것임을 특징으로 하는 유도체.
  13. 제1항 내지 제12항중 어느하나의 항에 있어서, R2는 2-티에닐, 2-셀레니에닐, 2-푸릴, 2-티아졸릴, 2-(1-메틸)-피롤릴 또는 메톡시페닐인 것을 특징으로 하는 유도체.
  14. 제1항 내지 제13항중 어느 하나의 항에 따른 구조식(I)의 피리미딘 유도체를 치료제에 사용하는 방법.
  15. 제1항 내지 제13항중 어느 하나의 항에 따른 구조식(I)의 피리미딘 유도체를 유효성분으로 하고, 약학적으로 허용가능한 담체를 함유하는 것을 특징으로 하는 약제조성물.
  16. 제1항 내지 제13항중 어느 하나의 항에 따른 구조식(1)의 화합물이 유효량을투여시키는 것을 특징으로 하는, 동물 또는 사람 숙주의 바이러스감염에 대한 치료 및/ 또는 예방에 사용하는 방법.
  17. 제16항에 있어서, 인간면역결핍 바이러스 및 간염 B 바이러스를 비롯하여 복제를 위해 역전사를 필요로 하는 바이러스에 의한 감염의 치료에 사용하는 방법.
  18. 제1항 내지 제13항중 어느 하나의 항에 따른 구조식(I)의 화합물의 유효량을 투여시키는 것을 특징으로 하는 AIDS의 치료방법.
  19. 제16항에 있어서, 헤르페스 바이러스에 의한 감염의 치료제에 사용하는 방법.
  20. 후천성 면역결핍증과 제를 위해 역전사를 필요로 하는 바이러스에 의한 감염의 치료 및/ 또는 예방처치를 위한 약제의 제조를 위해 사용되는 것을 특징으로 하는 제1항 내지 제13항중 어느 하나의 항에 따른 구조식(I)의 화합물의 용도.
  21. 제2O항에 있어서, HIV-바이러스에 의한 감염의 치료제의 제조를 위해 사용되는 것을 특징으로 하는 용도.
  22. 제2O항에 있어서, 간염 B 바이러스에 의한 감염의 치료제의 제조를 위해 사용되는 것을 특징으로 하는 용도.
  23. 다음 구조식(I)의 피리미딘 유도체를 제조하는데 있어서,
    (상기식에서 치환기 R1, R2, R3, R4및 R5는 제1항에서 상술한 바와 같다).
    A. 피리미딘 유도체의 N1위치에 다음식으로 표시되는 글루코사이드를 축합반응시키고;
    (상기식에서, Z는 염소, 브롬, 요오드, 아실옥시 또는 알콕시이다.)
    B. 2,2'-언하이드로 뉴클레오시드 아날로그를 그에 상응하는 아라비노실-피리미딘 뉴클레오시드 아날로그의 β-아미노머를 가수분해시킨 후;
    (상기식에서, R1″는 산소이거나 NH이다).
    C. 글리콘 부위의 3-위치의 유도된 수산기 Y를 플루오로, OCH3, N3, CN 또는 C≡CH 치환기로 치환시키는 것을 특징으로 하는 구조식(I)로 표시되는 피리미딘 유도체의 제조방법.
    (상기 식들에서 R1내지 R5및 n은 제1항에서 상술한 바와 같으며 이들은 임의적으로 적당한 보호기에 의해 보호된것일 수 있다)
  24. 다음 구조식(I)로 표시되는 화합물
    상기식에서 R1은 OH 또는 NH2이며 R2는 다음 구조식으로 표시되는 기이다.
    (상기 식에서, X는 산소, 황, N-R7혹은 세슘이고, R6는 수소, 직쇄 또는 분쇄형 C1내지 C10의 알킬, 플루오르, 염소, 브롬, 요오드, X-R7, -CH=CH-R|7, -C=C=R7, CO2R7, CH2X-R7이며, R7는 수소, 직쇄 또는 분쇄형 C1내지 C5의 알킬 또는 페닐이다.)
  25. 제24항에 있어서, R2는 2-티에닐, 2-셀레니에닐, 2-푸릴, 2-티아졸릴, 2-(1-메틸)피롤릴 또는 메톡시페닐인 것을 특징으로 하는 화합물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900700287A 1988-06-10 1989-06-07 피리미딘 유도체 Withdrawn KR900701815A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SE8802173A SE8802173D0 (sv) 1988-06-10 1988-06-10 Pyrimidine derivatives
SE8802173-8 1988-06-10
PCT/SE1989/000322 WO1989012061A1 (en) 1988-06-10 1989-06-07 Pyrimidine nucleosides and intermediates

Publications (1)

Publication Number Publication Date
KR900701815A true KR900701815A (ko) 1990-12-04

Family

ID=20372582

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900700287A Withdrawn KR900701815A (ko) 1988-06-10 1989-06-07 피리미딘 유도체

Country Status (20)

Country Link
US (2) US5440040A (ko)
EP (2) EP0357571B1 (ko)
JP (1) JP2851094B2 (ko)
KR (1) KR900701815A (ko)
AT (1) ATE136308T1 (ko)
AU (1) AU637574B2 (ko)
CA (1) CA1339313C (ko)
DE (1) DE68926137T2 (ko)
DK (1) DK291890A (ko)
ES (1) ES2087090T3 (ko)
FI (1) FI94643C (ko)
GR (1) GR3020212T3 (ko)
HU (1) HU211736B (ko)
IE (1) IE62914B1 (ko)
MY (1) MY109743A (ko)
NO (1) NO175981C (ko)
PH (1) PH27219A (ko)
PT (1) PT90803B (ko)
SE (1) SE8802173D0 (ko)
WO (1) WO1989012061A1 (ko)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5159067A (en) * 1987-01-28 1992-10-27 University Of Georgia Research Foundation Inc. 5'-Diphosphohexose nucleoside pharmaceutical compositions
SE8802173D0 (sv) * 1988-06-10 1988-06-10 Astra Ab Pyrimidine derivatives
US5688778A (en) * 1989-05-15 1997-11-18 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Nucleoside analogs
CA2479846C (en) * 1989-05-15 2007-07-24 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Scienc Es Of The Czech Republic Phosphonomethoxymethylpurine/pyrimidine derivatives
US5118672A (en) * 1989-07-10 1992-06-02 University Of Georgia Research Foundation 5'-diphosphohexose nucleoside pharmaceutical compositions
FR2656867A1 (fr) * 1990-01-09 1991-07-12 Centre Nat Rech Scient Nouveau derives de la thymidine, leur preparation et les compositions qui les contiennent.
CA2039403A1 (en) * 1990-04-04 1991-10-05 Gerald Saischek Process for the manufacture of 2-deoxy-d-threo-pentofuranosides, intermediates for their manufacture and their use
US5128458A (en) * 1990-04-20 1992-07-07 Southern Research Institute 2',3'-dideoxy-4'-thioribonucleosides as antiviral agents
ZA914894B (en) 1990-07-02 1992-04-29 Squibb & Sons Inc Purinyl and pyrimidinyl tetrahydrofurans
EP0477454A1 (en) * 1990-09-28 1992-04-01 Merrell Dow Pharmaceuticals Inc. Novel phosphonate derivatives of certain nucleosides
SE9003151D0 (sv) * 1990-10-02 1990-10-02 Medivir Ab Nucleoside derivatives
US5672697A (en) * 1991-02-08 1997-09-30 Gilead Sciences, Inc. Nucleoside 5'-methylene phosphonates
DE4110977A1 (de) * 1991-04-05 1992-10-08 Bayer Ag Substituierte 2',3'-didesoxy-5-trifluormethyluridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
TW393513B (en) * 1991-11-26 2000-06-11 Isis Pharmaceuticals Inc Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines
ATE226093T1 (de) * 1991-11-26 2002-11-15 Isis Pharmaceuticals Inc Gesteigerte bildung von triple- und doppelhelices aus oligomeren mit modifizierten pyrimidinen
US6235887B1 (en) 1991-11-26 2001-05-22 Isis Pharmaceuticals, Inc. Enhanced triple-helix and double-helix formation directed by oligonucleotides containing modified pyrimidines
AU4671193A (en) * 1992-07-13 1994-01-31 Kenneth E. Sherman Composition and method of treating hepatitis b
US6200952B1 (en) * 1993-06-02 2001-03-13 Sciclone Pharmaceuticals, Inc. Combination therapy method for treating chronic hepatitis B
US5502177A (en) * 1993-09-17 1996-03-26 Gilead Sciences, Inc. Pyrimidine derivatives for labeled binding partners
US6432924B1 (en) 1993-12-26 2002-08-13 East Carolina University Method of treating disorders characterized by overexpression of cytidine deaminase or deoxycytidine deaminase
EP0767657A4 (en) * 1994-06-22 1999-01-20 Nexstar Pharmaceuticals Inc NOVEL PROCESS FOR THE PRODUCTION OF KNOWN AND NEW NUCLEOSIDES, MODIFIED IN THE 2 'POSITION BY INTRAMOLECULAR NUCLEOPHILIC DISPLACEMENT
DE4430401A1 (de) * 1994-08-26 1996-02-29 Chemprosa Holding Ag D-Xylofuranose-Derivate, Verfahren zu deren Herstellung, deren Verwendung und neue Zwischenverbindungen für das Verfahren
EP0876149A4 (en) * 1995-12-22 2001-09-26 Univ East Carolina METHOD FOR TREATING DISORDERS CHARACTERIZED BY A CYTIDINE DEAMINASE OR DESOXYCYTIDINE DEAMINASE
US5747526A (en) * 1996-01-25 1998-05-05 Hollinshead; Ariel C. Anti-HIV /Aids Chemo(C)-, immuno(I)-, or ci-therapy using tur (or related compounds) and/or NVA (or EPV)
US5869493A (en) 1996-02-16 1999-02-09 Medivir Ab Acyclic nucleoside derivatives
JP3613424B2 (ja) * 1996-09-27 2005-01-26 財団法人国際超電導産業技術研究センター 酸化物超電導体の製造方法
AU747242B2 (en) 1997-01-08 2002-05-09 Proligo Llc Bioconjugation of macromolecules
US7427678B2 (en) * 1998-01-08 2008-09-23 Sigma-Aldrich Co. Method for immobilizing oligonucleotides employing the cycloaddition bioconjugation method
US6090602A (en) * 1998-02-18 2000-07-18 Promelas Research Corporation Levo-monosaccharide in a nucleoside analog for use as an anti-retroviral agent
ATE344271T1 (de) 1998-02-25 2006-11-15 Univ Emory 2'-fluoronukleoside
ATE277064T1 (de) * 1999-05-26 2004-10-15 Hoffmann La Roche Verfahren zur herstellung von vinylpyrimidinderivaten
BR0114837A (pt) 2000-10-18 2006-05-09 Pharmasset Ltd nucleosìdeos modificados para tratamento de infecções viróticas e proliferação celular anormal
BR0210594A (pt) 2001-06-22 2005-11-01 Pharmasset Ltd (beta)-d ou (beta)-l-3-halonucleosìdeo
WO2003062452A2 (en) * 2002-01-23 2003-07-31 Proligo, Llc Methods for the integrated synthesis and purification of oligonucleotides
EP1485395A4 (en) 2002-02-28 2011-04-13 Biota Scient Management NUCLEOTIDE MIMETICS AND PRODRUGS THEREOF
AU2002361255A1 (en) * 2002-12-31 2004-07-22 Proligo Llc Methods and compositions for the tandem synthesis of two or more oligonuleotides on the same solid support
US7262214B2 (en) 2003-02-26 2007-08-28 Merial Limited 1-N-arylpyrazole derivatives in prevention of arthropod-borne and mosquito-borne diseases
US7531186B2 (en) * 2003-12-17 2009-05-12 Merial Limited Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz
CN101044151B (zh) 2004-08-23 2011-01-19 弗·哈夫曼-拉罗切有限公司 抗病毒的4＇-叠氮基-核苷
US20080261823A1 (en) * 2004-12-10 2008-10-23 Yitzhak Tor Fluorescent Nucleoside Analogs That Mimic Naturally Occurring Nucleosides
US8895531B2 (en) 2006-03-23 2014-11-25 Rfs Pharma Llc 2′-fluoronucleoside phosphonates as antiviral agents
WO2007122634A2 (en) * 2006-04-24 2007-11-01 Jubilant Biosys Limited Pyrimidinediones as tyrosine kinase inhibitors
CA2656617C (en) 2006-07-05 2014-10-14 Aventis Agriculture 1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof
EA018935B1 (ru) 2006-10-10 2013-11-29 Медивир Аб Нуклеозидный ингибитор для вгс (hcv)
US7947447B2 (en) 2007-01-16 2011-05-24 Somalogic, Inc. Method for generating aptamers with improved off-rates
US8404830B2 (en) * 2007-07-17 2013-03-26 Somalogic, Inc. Method for generating aptamers with improved off-rates
GB0815968D0 (en) * 2008-09-03 2008-10-08 Angeletti P Ist Richerche Bio Antiviral agents
JP5755143B2 (ja) 2008-11-19 2015-07-29 メリアル リミテッド アリールピラゾールおよび／またはホルムアミジンを含む組成物、それらの方法ならびに使用
KR101246911B1 (ko) * 2009-11-02 2013-03-25 한국화학연구원 신규한 2,4-피리미딘 유도체 및 이의 용도
US8980896B2 (en) 2009-12-17 2015-03-17 Merial, Inc. Compositions comprising macrocyclic lactone compounds and spirodioxepinoindoles
UA108641C2 (uk) 2010-04-02 2015-05-25 Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування
ES2905656T3 (es) 2010-04-12 2022-04-11 Somalogic Operating Co Inc Pirimidinas modificadas en posición 5 y su uso
KR102066757B1 (ko) 2011-11-17 2020-01-15 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 아릴 피라졸 및 치환된 이미다졸을 함유하는 조성물, 그의 방법 및 용도
JO3626B1 (ar) 2012-02-23 2020-08-27 Merial Inc تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها
TWI579274B (zh) 2012-04-20 2017-04-21 龍馬躍公司 製備１－芳基－５－烷基吡唑化合物的改良方法
EP3071588A4 (en) 2013-11-21 2017-08-02 Somalogic, Inc. Cytidine-5-carboxamide modified nucleotide compositions and methods related thereto
WO2016069983A1 (en) 2014-10-31 2016-05-06 Merial, Inc. Parasiticidal composition comprising fipronil
CN104892706A (zh) * 2015-04-27 2015-09-09 河南师范大学 具有抗寄生虫活性的异噁唑-核苷杂化体及其制备方法和应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2721466A1 (de) * 1977-05-12 1978-11-16 Robugen Gmbh Verfahren zur herstellung von 2'-desoxyribofuranosylnucleosiden
JPS54112880A (en) * 1978-02-21 1979-09-04 Matsura Teruo Novel uracil derivative and its manufacture
US4211773A (en) * 1978-10-02 1980-07-08 Sloan Kettering Institute For Cancer Research 5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides
AU575918B2 (en) * 1984-03-06 1988-08-11 Sloan-Kettering Institute For Cancer Research Hepatitis treatment with pyrimidine nucleoside compounds
US4666892A (en) * 1984-03-06 1987-05-19 Sloan-Kettering Memorial Cancer Center Method and composition for hepatitis treatment with pyrimidine nucleoside compounds
SE8605503D0 (sv) * 1986-12-19 1986-12-19 Astra Laekemedel Ab Novel medicinal use
SE8802173D0 (sv) * 1988-06-10 1988-06-10 Astra Ab Pyrimidine derivatives

Also Published As

Publication number Publication date
AU3750489A (en) 1990-01-05
AU637574B2 (en) 1993-06-03
NO175981C (no) 1995-01-11
HU894340D0 (en) 1991-08-28
MY109743A (en) 1997-05-31
FI94643B (fi) 1995-06-30
DK291890D0 (da) 1990-12-07
FI94643C (fi) 1995-10-10
EP0357571B1 (en) 1996-04-03
NO905300L (no) 1991-02-06
US5440040A (en) 1995-08-08
EP0357571A3 (en) 1990-06-13
JP2851094B2 (ja) 1999-01-27
EP0691333A2 (en) 1996-01-10
PH27219A (en) 1993-05-04
PT90803B (pt) 1994-10-31
GR3020212T3 (en) 1996-09-30
EP0691333A3 (ko) 1996-02-14
DE68926137D1 (de) 1996-05-09
NO175981B (no) 1994-10-03
JPH03504969A (ja) 1991-10-31
WO1989012061A1 (en) 1989-12-14
DK291890A (da) 1991-02-07
NO905300D0 (no) 1990-12-07
US5576429A (en) 1996-11-19
EP0357571A2 (en) 1990-03-07
CA1339313C (en) 1997-08-19
DE68926137T2 (de) 1996-11-14
HUT57230A (en) 1991-11-28
FI906053A0 (fi) 1990-12-07
HU211736B (en) 1995-12-28
PT90803A (pt) 1989-12-29
SE8802173D0 (sv) 1988-06-10
IE891816L (en) 1989-12-10
ES2087090T3 (es) 1996-07-16
ATE136308T1 (de) 1996-04-15
IE62914B1 (en) 1995-03-08

Similar Documents

Publication Publication Date Title
KR900701815A (ko) 피리미딘 유도체
KR930702371A (ko) 뉴클레오시드 유도체
KR900701817A (ko) 뉴클레오사이드 유도체와 그의 제조방법
ATE115958T1 (de) Nukleoside und nukleosid-analoge, pharmazeutische zusammensetzung und verfahren für die herstellung der bestandteile.
US4963533A (en) Therapeutic application of dideoxycytidinene
DK1140745T3 (da) Colchinolderivater som vaskulært skadelige midler
KR890003761A (ko) 치료학적 아시클릭 뉴클레오시드
KR890003382A (ko) 항 비루스성 화합물
KR950014067A (ko) 아릴아미드유도체
US6911460B2 (en) Antiviral agents and methods of treating viral infections
ATE2622T1 (de) 2-niedrigalkyl-7-substituierte-2 oder 3-cephem-4- carbonsaeuren, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen.
KR950701638A (ko) 푸린 동족체의 항비루스성 포스폰산 유도체(Antiviral phosphonic acid derivatives of purine analogues)
KR910000734A (ko) 네플라노신 유도체
KR910700230A (ko) 신규 히드록실아민 유도체
KR900017577A (ko) 폴리아민 유도체를 사용하여 세포- 중재의 면역성을 상승시키는 방법
KR900014385A (ko) 제약학적 치료
KR890012942A (ko) 5-치환된 오르니틴 유도체
US5116822A (en) Therapeutic application of dideoxycytidinene
KR900012925A (ko) 인돌 유도체
KR910000728A (ko) 시클로펜탄 유도체
KR890002128A (ko) 실비빈의 가용성 유도체, 그것의 제조방법 및 그것을 함유하는 제약학적 조성물
KR890000427A (ko) 아미노시클로펜틸 에테르 및 그의 제조방법 및 약제
KR890014560A (ko) 세팔로스포린 유도체 및 이의 제조방법
KR880013963A (ko) 글루코피라노즈 유도체
KR960703924A (ko) 항바이러스제로서 신규한 벤조티오펜 유사체(Novel Benzothiophene Analogs as Antiviral Agents)

Legal Events

Date Code Title Description
PA0109 Patent application

Patent event code: PA01091R01D

Comment text: Patent Application

Patent event date: 19900210

PG1501 Laying open of application
PC1203 Withdrawal of no request for examination
WITN Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid