KR900012932A - 항바이러스 성질을 지닌 치환된-1,3-옥사티올란 - Google Patents

항바이러스 성질을 지닌 치환된-1,3-옥사티올란 Download PDF

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KR900012932A
KR900012932A KR1019900001493A KR900001493A KR900012932A KR 900012932 A KR900012932 A KR 900012932A KR 1019900001493 A KR1019900001493 A KR 1019900001493A KR 900001493 A KR900001493 A KR 900001493A KR 900012932 A KR900012932 A KR 900012932A
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compound
oxathiolane
hydroxymethyl
cytosine
formula
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벨로우 베르나드
벨로우 피에레테
기엔-바 니게
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원본미기재
아이에이에프 바이오켐 인터내쇼날 인코오포레이티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • 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
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and 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
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
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    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

내용 없음

Description

항바리러스 성질을 지닌 치환된 -1,3-옥사티올란
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (28)

  1. 하기식(I)의 1,3-옥사티올란 및 그 기하학 이성체 및 광학 이성체, 및 이들 이성체의 혼합물과 그 약학적 허용 유도체.
    상기식중, R1은 수소이고, R2는 푸른 또는 피리미딘 염기 또는 유사체 또는 그 유도체이고, Z은 S,S=0 또는 SO2로 구성되는 그룹으로 부터 선택된다.
  2. 제1항에 있어서, 상기 화합물이 시스=| 이성체의 형태로 존재하는 것을 특징으로 하는 식(I)의 화합물.
  3. 제1항 또는 제2항에 있어서, 상기 Z가 S인것을 특징으로 하는 식(I)의 화합물.
  4. 제1항 내지 제3항에 어느 한항에 있어서, 상기 R2가 하기로부터 선택되는 것을 특징으로 하는 식(I)의 화합물.
    상기식에서, R3는 수소 또는 C1-6알킬기의 그룹으로 부터 선택되며, R4및 R5는 수소, 히드록시메틸, 트리플루오로메틸, 치환 또는 비치환, 포화 또는 불포화 C1-6알킬, 브롬, 염소, 불소, 또는 요오드로 구성되는 그룹으로부터 선택되며, R6는 수소, 시아노, 카르복시, 에톡시카르보닐, 카르바모일, 또는 티오카르바모일로 구성되는 그룹으로부터 선택되며, X 및 Y는 수소, 브롬, 염소, 불소, 요오드, 아미노기 또는 히드록실기로 구성되는 그룹으로부터 선택된다.
  5. 제1항 내지 제4항중 어느 한 항에 있어서, 상기 R2가인 화합물.
    식중, R3는 수소 또는 C1-6알킬기의 그룹으로 부터 선택되며, R4및 수소, 히드록시메틸, 트리를루오로메틸, 치환 또는 비치환, 포화 또는 불포화 C1-6알킬, 브롬, 염소, 불소, 또는 요오드로 구성되는 그룹으로 부터 선택된다.
  6. 라세믹 혼합물 및 단일 에난티오머의 형태로 존재하는 하기로 구성되는 그룹으로 부터 선택된 화합물 및 그 약학적 허용 유도체.
    -2-히드록시메틸-5-(시토신-1'-일)-1,3-옥사티올란,트랜스-2-히드록시메틸-5-(시토신-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-벤조일옥시메틸-5-(시토신-1'-일)-1,3-옥사티올란,트랜스-2-벤조일옥메틸-5-(시토신-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란, 트랜스-2-히드록시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-벤조일옥시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란 및 그 혼합물, 및-2-히드록시메틸-5-(시토신-1'-일)-1,3-옥사티올란,-2-히드록시메틸-5-(N-디메틸아미노-메틸렌시토신-1'-일)-1,3-옥사티올란, 비스--2-석씨닐옥시메틸-5-(시토신-1'-일)-1,3-옥사티올란,-2-벤조일옥시메틸-5-(6'-클로로푸린-N-9'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(6'-클로로푸린-N-9'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(6'-피드록시푸린-N-9'-일)-1,3-옥사티올란,-2-벤조일옥시메틸-5-(우라실-N-9'-일)-1,3-옥사티올란, 트랜스-2-벤조일옥시메틸-5-(우라실-N-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(우라실-N-1'-일)-1,3-옥사티올란,-2-벤조일옥시메틸-5-(티민-N-1'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(티민-N-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(티민-N-1'-일)-1,3-옥사티올란.
  7. -2-히드록시메틸-5-(시토신-1'-일)-1,3-옥사티올란 및 그 약학적 허용 유도체.
  8. 제1항 내지 제7항중 어느 한 항에 있어서, 상기 화합물이 라세믹 혼합물의 형태로 존재하는 것을 특징으로 하는 화합물.
  9. 제1항 내지 제7항중 어느 한 항에 있어서, 상기 화합물이 단일 에난티오머의 형태로 존재하는 것을 특징으로 하는 화합물.
  10. 제1항 내지 제9항중 어느 한 항에 있어서, 상기 화합물이 활성 치료제로서 유용한 약학적 허용 유도체인 것을 특징으로 하는 식(I)의 화합물.
  11. 제1항 내지 제9항중 어느 한 항에 있어서, 상기 화합물이 바이러스 감염 치료용 약제에 유용한 약학적 허용 유도체인 것을 특징으로 하는 식(I)의 화합물.
  12. 제1항 내지 제9항중 어느 한 항에 정의된 식(I)의 화합물 또는 그 약학적 어용 담체를 포함하는 약학 제제.
  13. 제12항에 있어서, 치료제를 부가적으로 포함하는 약학제제.
  14. 하기식(Ⅷ)의 1,3-옥사티올란 및 그 기하학 및 광학이성체, 및 이들 이성체의 혼합물.
    상기식에서, R1은 수소 또는 히드록실 보호기이며, L은 알콕시 카르보닐기, 요오드, 브롬, 염소 또는 -OR[여기서, R은 치환 또는 비치환, 포화 또는 불포화 알킬기 및 치환 또는 비치환, 포화 또는 지방족 또는 방향족 아실기]이며, Z는 상기에서 정의한 바와 같다.
  15. 하기식(Ⅶ)에 에스테르 및 광학 이성체, 및 이들 이성체의 혼합물.
    상기식중, W는 PO4, SPO3, 또는(여기서 n은 1 내지 10의 정수)이며, J는 어떤 뉴클레오시드 또는 뉴클레오시드 유사체 또는 그 유도체이고, Z는S, S=O 또는 SO2이고, R2는 푸린 또는 피리미딘 염기 또는 유사체 또는 그 유도체이다.
  16. 제15항에 있어서, 상기 J가인 것을 특징으로 하는 화합물.
    식중, R2및 Z는 상기에서 정의한 바와 같다.
  17. (a) 하기식(Ⅷ)의 화합물을 염기 R2-H기와 반응시키고, (b) 식(I)의 황화합물을 식(I)의 다른 화합물로 염기 상호 전환시키고, (c) 하기식(Ⅸ)의 화합물을 하기식(Ⅹ)의 화합물로 반응시키고, (d) 하기식(ⅩⅡ)의 화합물을 식(I)의 화합물로 전환시키고, 필요하거나 요구되는 경우, 상기(a) 내지 (d)단계중의 어느 한 단계로부터 얻은 화합물을(ⅰ) 보호기를 제거하고, (ⅱ) 식(I)의 화합물 또는 그 염을 약학적 허용염으로 전환시키는 단계를 포함하는 하나 또는 두개의 추가 반응에 수반시키는 것을 특징으로 하는 하기식(I)의 화합물 및 그 약학적 허용 유도체의 제조방법.
    식중, R1은 수소이고, R2는 푸린 또는 피리미딘 염기 또는 유사체 또는 그 유도체이고, Z는 S,S=O 또는 SO2이다.
    식중, R1은 수소 또는 히두록실 보호기이고, L은 치환 가능한 원자 도는 기이다. Z는 상기에서 정의한 바와같다.
    식중, R2및 Z는 상기에서 정의한 바와 같다.
    식중, P는 보호기이다.
    식중, R1및 Z는 상기에서 정의한 바와 같다.
  18. 제17항에 있어서, 상기식(I)의 화합물이 이것의이성체의 형태로 얻어지는 것을 특징으로 하는 방법.
  19. 제17항 또는 제18항에 있어서, 상기 Z가 S인 것을 특징으로 하는 방법.
  20. 제17항 또는 제19항중 어느 한 항에 있어서, 상기 R2가 하기로부터 선택되는 것을 특징으로 하는 방법.
  21. 제17항 또는 제19항중 어느 한 항에 있어서,
    상기 R2가인 것을 특징으로 하는 방법.
    R3는 수소, 트리플루오로메틸 또는 포화 또는 불포화C1-6알킬기의 그룹으로 부터 선택되고, R4는 수소, 히드록시메틸, 트리를루오로메틸, 치환 또는 비치환, 포화 또는 불포화 C1-6알킬, 브롬, 염소, 불소, 또는 요오드로 부터 구성되는 그룹으로 부터 선택된다.
  22. 라세믹 혼합물 및 단일 에난티오머의 형태로 존재하는 하기로 구성되는 그룹으로 부터 선택된 화합물 및 그 약학적 허용 유도체.
    -2-히드록시메틸-5-(시토신-1'-일)-1,3-옥사티올란,트랜스-2-히드록시메틸-5-(시토신-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-벤조일옥시메틸-5-(시토신-1'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(시토신-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란,트랜스-2-히드록시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-벤조일옥시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(N4'-아세틸-시토신-1'-일)-1,3-옥사티올란 및 그 혼합물, 및-2-히드록시메틸-5-(시토신-1'-일)-3-옥소-1,3-옥사티올란,-2-히드록시메틸-5-(N-디메틸아미노-메틸렌시토신-1'-일)-1,3-옥사티올란, 비스--2-석씨닐옥시메틸-5-(시토신-1'-일)-1,3-옥사티올란,-2-벤조일옥시메틸-5-(6'-클로로푸린-N-9'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(6'-클로로푸린-N-9'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(6'-히드록시푸린-N-9'-일)-1,3-옥사티올란,-2-벤조일옥시메틸-5-(우라실-N-1'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(우라실-N-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(우라실-N-1'-일)-1,3-옥사티올란,-2-벤조일옥시메틸-5-(티민-N-1'-일)-1,3-옥사티올란,트랜스-2-벤조일옥시메틸-5-(티민-N-1'-일)-1,3-옥사티올란 및 그 혼합물,-2-히드록시메틸-5-(티민-N-1'-일)-1,3-옥사티올란.
  23. 제17항 내지 제 21항중 어느 한 항에 있어서, 상기 식(I)의 화합물이 시스-2-히드록시메틸-5-(시토신-1'-일)-1,3-옥사티올란 및 그 약학적 허용 유도체인 것을 특징으로 하는 방법.
  24. 제17항 내지 제 23항중 어느 한 항에 있어서, 상기 식(I)의 화합물이 라세믹 혼합물의 형태로 얻어지는 것을 특징으로 하는 방법.
  25. 제1항 내지 제7항중 어느 한 항에 있어서, 상기 식(I)의 화합물이 실질적으로 단일 에난티오머의 형태로 얻어지는 것을 특징으로 하는 방법.
  26. 제17항 내지 제25항중 어느 한 항에 있어서, 상기 단계(a)에서 L기가 알콕시카르보닐, 요오드, 브롬, 염소 또는 -OR[여기서, R은 치환 또는 비치환, 포화 또는 불포화 알킬기 또는 치환 또는 비치환 지방족 또는 방향족 아실기]로 구성되는 그룹으로 부터 선택되는 것을 특징으로 하는 방법.
  27. 제17항 내지 제26항중 어느 한 항에 있어서, 상기식 (Ⅷ)의 화합물이 루이스산 및 트리메틸 실릴 트리플레이트 존재하에, 상용성 용매중에서 실질화된 푸린 또는 피리미딘 염기와 반응하는 것을 특징으로 하는 방법.
  28. 제17항 정의된 식(I)의 화합물 또는 그 약학적 허용 유도체와 약학적 허용 담체를 혼합시키는 것을 특징으로 하는 약학 제제의 제조 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900001493A 1989-02-08 1990-02-08 항바이러스 성질을 지닌 치환된-1,3-옥사티올란 KR960007531B1 (ko)

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Families Citing this family (149)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5047407A (en) 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
US6903224B2 (en) * 1988-04-11 2005-06-07 Biochem Pharma Inc. Substituted 1,3-oxathiolanes
US7119202B1 (en) 1989-02-08 2006-10-10 Glaxo Wellcome Inc. Substituted-1,3-oxathiolanes and substituted-1,3-dioxolanes with antiviral properties
US6350753B1 (en) 1988-04-11 2002-02-26 Biochem Pharma Inc. 2-Substituted-4-substituted-1,3-dioxolanes and use thereof
US5684164A (en) * 1988-04-11 1997-11-04 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
US5466806A (en) * 1989-02-08 1995-11-14 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
US5270315A (en) * 1988-04-11 1993-12-14 Biochem Pharma Inc. 4-(purinyl bases)-substituted-1,3-dioxlanes
UA45942A (uk) * 1989-02-08 2002-05-15 Біокем Фарма, Інк. 1,3-оксатіолан, його похідні, спосіб (варіанти) його одержання та фармацевтична композиція
ES2196004T3 (es) * 1989-02-08 2003-12-16 Iaf Biochem Int Procedimiento para preparar 1,3-oxatiolanos sustituidos con propiedades antivirales.
US6346627B1 (en) 1990-02-01 2002-02-12 Emory University Intermediates in the synthesis of 1,3-oxathiolane nucleoside enantiomers
US6703396B1 (en) 1990-02-01 2004-03-09 Emory University Method of resolution and antiviral activity of 1,3-oxathiolane nuclesoside enantiomers
US5700937A (en) * 1990-02-01 1997-12-23 Emory University Method for the synthesis, compositions and use of 2'-deoxy-5-fluoro-3'-thiacytidine and related compounds
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
US5914331A (en) * 1990-02-01 1999-06-22 Emory University Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
US5276151A (en) * 1990-02-01 1994-01-04 Emory University Method of synthesis of 1,3-dioxolane nucleosides
GB9009861D0 (en) 1990-05-02 1990-06-27 Glaxo Group Ltd Chemical compounds
US6228860B1 (en) 1990-11-13 2001-05-08 Biochem Pharma Inc. Substituted 1,3-oxathiolanes with antiviral properties
AU8864191A (en) * 1990-11-13 1992-06-11 Biochem Pharma Inc. Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
US5587480A (en) * 1990-11-13 1996-12-24 Biochem Pharma, Inc. Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
US6369066B1 (en) 1990-11-13 2002-04-09 Biochem Pharma, Inc. Substituted 1,3-oxathiolanes with antiviral properties
US5925643A (en) * 1990-12-05 1999-07-20 Emory University Enantiomerically pure β-D-dioxolane-nucleosides
US5248776A (en) * 1990-12-05 1993-09-28 University Of Georgia Research Foundation, Inc. Process for enantiomerically pure β-L-1,3-oxathiolane nucleosides
US5179104A (en) * 1990-12-05 1993-01-12 University Of Georgia Research Foundation, Inc. Process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides
WO1992010496A1 (en) * 1990-12-05 1992-06-25 University Of Georgia Research Foundation, Inc. ENANTIOMERICALLY PURE β-L-(-)-1,3-OXATHIOLANE NUCLEOSIDES
US5444063A (en) * 1990-12-05 1995-08-22 Emory University Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity
IL100502A (en) * 1991-01-03 1995-12-08 Iaf Biochem Int PHARMACEUTICAL PREPARATIONS CONTAINING CIS-4-AMINO-1-) 2-HYDROXIMETHIL-1,3-OXETYOLEN-5-IL (-
IL100965A (en) * 1991-02-22 1999-12-31 Univ Emory 2 - Hydroxymethyl - 5 -) 5 - Fluorocytocin - 1 - Eyal (- 1, 3 - Oxathiolane, its resolution and pharmaceuticals containing it
US6812233B1 (en) 1991-03-06 2004-11-02 Emory University Therapeutic nucleosides
ATE361293T1 (de) * 1991-03-06 2007-05-15 Univ Emory Salze und amide von (-) cis 5-fluoro-2'-deoxy-3'- thiacytidine geeignet für die behandlung von hepatitis b
GB9104740D0 (en) * 1991-03-06 1991-04-17 Wellcome Found Antiviral nucleoside combination
US5817667A (en) * 1991-04-17 1998-10-06 University Of Georgia Research Foudation Compounds and methods for the treatment of cancer
WO1992018517A1 (en) * 1991-04-17 1992-10-29 Yale University Method of treating or preventing hepatitis b virus
GB9109506D0 (en) * 1991-05-02 1991-06-26 Wellcome Found Therapeutic nucleosides
EP0513917B2 (en) * 1991-05-16 2001-03-07 Glaxo Group Limited Antiviral combinations containing nucleoside analogs
GB9110874D0 (en) * 1991-05-20 1991-07-10 Iaf Biochem Int Medicaments
ZA923641B (en) * 1991-05-21 1993-02-24 Iaf Biochem Int Processes for the diastereoselective synthesis of nucleosides
GB9111902D0 (en) * 1991-06-03 1991-07-24 Glaxo Group Ltd Chemical compounds
GB9116601D0 (en) * 1991-08-01 1991-09-18 Iaf Biochem Int 1,3-oxathiolane nucleoside analogues
ATE138928T1 (de) * 1991-09-04 1996-06-15 Stichting Rega V Z W Substituierte nukleosidderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen
US20050192299A1 (en) * 1992-04-16 2005-09-01 Yung-Chi Cheng Method of treating or preventing hepatitis B virus
DK0639971T3 (da) * 1992-05-13 2000-03-20 Wellcome Found Terapeutiske kombinationer
US6177435B1 (en) 1992-05-13 2001-01-23 Glaxo Wellcome Inc. Therapeutic combinations
GB9226879D0 (en) * 1992-12-23 1993-02-17 Iaf Biochem Int Anti-viral compounds
US6005107A (en) * 1992-12-23 1999-12-21 Biochem Pharma, Inc. Antiviral compounds
US6444656B1 (en) 1992-12-23 2002-09-03 Biochem Pharma, Inc. Antiviral phosphonate nucleotides
GB9311709D0 (en) * 1993-06-07 1993-07-21 Iaf Biochem Int Stereoselective synthesis of nucleoside analogues using bicycle intermediate
US20020120130A1 (en) * 1993-09-10 2002-08-29 Gilles Gosselin 2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents
AU7954694A (en) 1993-09-10 1995-03-27 Centre National De La Recherche Scientifique (Cnrs) Nucleosides with anti-hepatitis b virus activity
US5587362A (en) * 1994-01-28 1996-12-24 Univ. Of Ga Research Foundation L-nucleosides
IL113432A (en) 1994-04-23 2000-11-21 Glaxo Group Ltd Process for the diastereoselective synthesis of nucleoside analogues
FR2720397B1 (fr) * 1994-05-24 1996-08-23 Laphal Laboratoires Sa Nouveaux oxathiolanes, leur procédé de préparation et les compositions pharmaceutiques qui en renferment.
IL115156A (en) * 1994-09-06 2000-07-16 Univ Georgia Pharmaceutical compositions for the treatment of cancer comprising 1-(2-hydroxymethyl-1,3-dioxolan-4-yl) cytosines
US5703058A (en) * 1995-01-27 1997-12-30 Emory University Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent
US6391859B1 (en) 1995-01-27 2002-05-21 Emory University [5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine nucleosides
US5808040A (en) * 1995-01-30 1998-09-15 Yale University L-nucleosides incorporated into polymeric structure for stabilization of oligonucleotides
MY115461A (en) 1995-03-30 2003-06-30 Wellcome Found Synergistic combinations of zidovudine, 1592u89 and 3tc
WO1996031217A1 (en) * 1995-04-04 1996-10-10 Duke University Inhibiting retroviral replication
ES2276404T3 (es) * 1995-06-07 2007-06-16 Emory University Nucleosidos con actividad antivirus de la hepatitis-b.
GB9605293D0 (en) * 1996-03-13 1996-05-15 Glaxo Group Ltd Medicaments
FR2746396B1 (fr) * 1996-03-20 1998-06-05 Inst Nat Sante Rech Med 1,3-thiazolidin-4-ones et 1,3-thiazolidines substituees, procede d'obtention de ces composes et leurs utilisations comme medicaments
CZ429498A3 (cs) 1996-06-25 1999-06-16 Glaxo Group Limited Kombinace obsahující VX478, zidovudin, FTC a/nebo 3TC pro léčbu infekce HIV
US5753789A (en) * 1996-07-26 1998-05-19 Yale University Oligonucleotides containing L-nucleosides
US6113920A (en) * 1996-10-31 2000-09-05 Glaxo Wellcome Inc. Pharmaceutical compositions
US5792773A (en) * 1996-11-15 1998-08-11 Yale University L-β-dioxolane uridine analog administration for treating Epstein-Barr virus infection
US6022876A (en) * 1996-11-15 2000-02-08 Yale University L-β-dioxolane uridine analogs and methods for treating and preventing Epstein-Barr virus infections
US20040044016A1 (en) * 1997-01-31 2004-03-04 Mitsubishi Chemical Corporation Antiviral agents
EA001920B1 (ru) 1997-03-19 2001-10-22 Эмори Юниверсити Синтез 1,3-оксаселеноланнуклеозидов, их активность против вируса иммунодефицита человека и против вируса гепатита-b
TW536403B (en) * 1997-03-24 2003-06-11 Glaxo Group Ltd An ethanol and ethylenediaminetetraacetic acid free pharmaceutical composition comprising lamivudine and exhibiting antimicrobial preservative efficacy
IT1290447B1 (it) * 1997-03-28 1998-12-03 Zambon Spa Derivati 1,3-ossatiolanici ad attivita' antivirale
AU6898498A (en) 1997-04-07 1998-10-30 Triangle Pharmaceuticals, Inc. Use of mkc-442 in combination with other antiviral agents
CA2322008C (en) 1998-02-25 2011-06-28 Emory University 2'-fluoronucleosides
EP1754710A3 (en) 1998-02-25 2007-12-19 Emory University 2'-Fluoroncucleosides
CA2714085C (en) 1998-08-12 2013-02-05 Emory University Method of manufacture of 1,3-oxathiolane nucleosides
US6979561B1 (en) * 1998-10-09 2005-12-27 Gilead Sciences, Inc. Non-homogeneous systems for the resolution of enantiomeric mixtures
EP1124562B1 (en) 1998-11-02 2005-01-19 Gilead Sciences, Inc. Combination therapy to treat hepatitis b virus
US6458773B1 (en) 1998-11-05 2002-10-01 Emory University Nucleoside with anti-hepatitis B virus activity
NZ513094A (en) 1998-12-23 2004-05-28 Shire Biochem Inc Antiviral nucleoside analogues
WO2000057861A2 (en) * 1999-03-29 2000-10-05 Shire Biochem Inc. Use of cytidine derivatives for the treatment of leukaemia
ATE235488T1 (de) 1999-05-26 2003-04-15 Johnson Matthey Pharmaceutical Verfahren zu trennung von ftc isomere und deren derivate
US6752929B1 (en) * 1999-05-26 2004-06-22 Johnson Matthey Pharmaceutical Materials, Inc. Methods of separating FTC isomers and derivatives thereof
US6653318B1 (en) 1999-07-21 2003-11-25 Yale University 5-(E)-Bromovinyl uracil analogues and related pyrimidine nucleosides as anti-viral agents and methods of use
US6432966B2 (en) * 1999-10-29 2002-08-13 Smithkline Beecham Corporation Antiviral combinations
EP1634888A3 (en) 1999-11-12 2007-11-21 Pharmasset, Inc. Synthesis of 2'-deoxy-L-nucleosides
TR200601784T2 (tr) * 1999-11-12 2007-01-22 Pharmasset Ltd. 2'-deoksi-L-nükleositlerin sentezi
US6436948B1 (en) 2000-03-03 2002-08-20 University Of Georgia Research Foundation Inc. Method for the treatment of psoriasis and genital warts
GB0016845D0 (en) * 2000-07-07 2000-08-30 Leuven K U Res & Dev Pharmaceutical composition for treatment of HIV infection
WO2002051852A1 (fr) * 2000-12-27 2002-07-04 Mitsui Chemicals, Inc. Procede de production d'un derive de saccharide non naturel
ATE312097T1 (de) * 2001-03-01 2005-12-15 Gilead Sciences Inc Polymorphe und andere kristalline formen von cis- ftc
CA2351049C (en) 2001-06-18 2007-03-13 Brantford Chemicals Inc. Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers
JP2003039582A (ja) * 2001-07-19 2003-02-13 Three M Innovative Properties Co 湿潤防滑性シート及び湿潤防滑構造体
MY169670A (en) 2003-09-03 2019-05-08 Tibotec Pharm Ltd Combinations of a pyrimidine containing nnrti with rt inhibitors
US6855346B2 (en) * 2001-10-05 2005-02-15 Tzu-Sheng Wu Pharmaceutical composition having prophylactic effects on lamivudine-related disease relapse and drug resistance and methods of using the same
DK1441735T3 (da) * 2001-10-26 2006-06-12 Angeletti P Ist Richerche Bio N-substituerede hydroxypyrimidinon-carboxamid-inhibitorer af HIV-integrase
BR0214940A (pt) * 2001-12-14 2006-05-30 Pharmasset Ltd preparação de intermediários úteis na sìntese de nucleosìdeos antivirais
IL163666A0 (en) 2002-02-22 2005-12-18 New River Pharmaceuticals Inc Active agent delivery systems and methods for protecting and administering active agents
KR101108115B1 (ko) 2002-08-06 2012-01-31 파마셋 인코포레이티드 1,3-디옥솔란 뉴클레오사이드의 제조 방법
DE10238723A1 (de) * 2002-08-23 2004-03-11 Bayer Ag Phenyl-substituierte Pyrazolyprimidine
DE10238722A1 (de) * 2002-08-23 2004-03-11 Bayer Ag Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse
DE10238724A1 (de) * 2002-08-23 2004-03-04 Bayer Ag Alkyl-substituierte Pyrazolpyrimidine
AU2003291457A1 (en) * 2002-11-08 2004-06-03 Glaxo Group Limited Pharmaceutical antiviral compositions
CA2502625A1 (en) 2002-12-09 2004-06-24 The University Of Georgia Research Foundation, Inc. Dioxolane thymine and combinations for use against resistant strains of hiv
CA2512319A1 (en) * 2003-01-14 2004-08-05 Gilead Sciences, Inc. Compositions and methods for combination antiviral therapy
DE10320785A1 (de) * 2003-05-09 2004-11-25 Bayer Healthcare Ag 6-Arylmethyl-substituierte Pyrazolopyrimidine
US8044060B2 (en) 2003-05-09 2011-10-25 Boehringer Ingelheim International Gmbh 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory
DE102004001873A1 (de) * 2004-01-14 2005-09-29 Bayer Healthcare Ag Cyanopyrimidinone
DK1778251T3 (da) 2004-07-27 2011-07-18 Gilead Sciences Inc Nukleosidphosphatkonjugater som anti-HIV-midler
JP2006214695A (ja) * 2005-02-07 2006-08-17 Sanken Setsubi Kogyo Co Ltd 空調システム
TWI375560B (en) 2005-06-13 2012-11-01 Gilead Sciences Inc Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same
TWI471145B (zh) * 2005-06-13 2015-02-01 Bristol Myers Squibb & Gilead Sciences Llc 單一式藥學劑量型
WO2007013047A2 (en) * 2005-07-29 2007-02-01 Ranbaxy Laboratories Limited Water-dispersible anti-retroviral pharmaceutical compositions
CN1328240C (zh) * 2005-08-31 2007-07-25 四川大学 苯甲酰氧基乙醛的制备方法
ATE484284T1 (de) * 2005-08-31 2010-10-15 Cipla Ltd Pharmazeutische kombinationen mit lamivudin, stavudin und nevirapin
ES2617582T3 (es) 2005-09-26 2017-06-19 Gilead Pharmasset Llc 4'-Nucleósidos modificados como agentes antivirales
RU2008128424A (ru) * 2005-12-14 2010-01-20 Сипла Лимитед (In) Фармацевтическая комбинация, включающая нуклеотидный и нуклеозидный ингибиторы обратной транскриптазы (такие как тенофовир и ламивудин) в различных частях дозы
US8895531B2 (en) * 2006-03-23 2014-11-25 Rfs Pharma Llc 2′-fluoronucleoside phosphonates as antiviral agents
AU2007237818B2 (en) * 2006-04-18 2012-09-27 Lupin Limited A novel crystalline form of lamivudine
EP2086955A2 (en) * 2006-10-30 2009-08-12 Lupin Ltd. An improved process for the manufacture of cis(-)-lamivudine
KR100840495B1 (ko) 2007-04-13 2008-06-23 한미약품 주식회사 라미부딘을 입체선택적으로 제조하는 방법
WO2008154817A1 (fr) 2007-06-18 2008-12-24 Zhang, Zhongneng Thiazolyl-dihydropyrimidines à substitution bromo-phényle
WO2009037538A2 (en) * 2007-09-17 2009-03-26 Aurobindo Pharma Ltd Process for the preparation of lamivudine form i
AU2008331167A1 (en) * 2007-11-29 2009-06-04 Ranbaxy Laboratories Limited Process and intermediates for the preparation of substituted 1, 3-oxathiolanes, especially lamivudine
SI2225232T1 (sl) * 2007-11-29 2012-12-31 Ranbaxy Laboratories Limited Postopek za pripravo substituiranih 1,3-oksatiolanov
WO2009068617A1 (en) * 2007-11-30 2009-06-04 Boehringer Ingelheim International Gmbh 1, 5-dihydro-pyrazolo (3, 4-d) pyrimidin-4-one derivatives and their use as pde9a modulators for the teatment of cns disorders
UA105362C2 (en) * 2008-04-02 2014-05-12 Бьорингер Ингельхайм Интернациональ Гмбх 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators
TW201010692A (en) 2008-06-19 2010-03-16 Public Univ Corp Nagoya City Univ Pharmaceutical composition for treatment or prevention of hbv infection
CA2736304A1 (en) 2008-09-08 2010-03-11 Boehringer Ingelheim International Gmbh Pyrazolopyrimidines and their use for the treatment of cns disorders
PL2364314T3 (pl) 2008-12-09 2014-08-29 Gilead Sciences Inc Modulatory receptorów Toll-podobnych
WO2010082128A1 (en) 2009-01-19 2010-07-22 Aurobindo Pharma Limited Process for the preparation of cis-nucleoside derivative
ES2460019T3 (es) * 2009-03-31 2014-05-13 Boehringer Ingelheim International Gmbh Derivados de 1-heterociclil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona y su uso como moduladores de PDE9A
KR101474570B1 (ko) 2009-04-13 2014-12-19 주식회사 대희화학 라미부딘의 신규한 중간체 및 이의 제조방법
AR077859A1 (es) * 2009-08-12 2011-09-28 Boehringer Ingelheim Int Compuestos para el tratamiento de trastornos del snc
WO2011045815A2 (en) 2009-10-14 2011-04-21 Matrix Laboratories Ltd. Process for the preparation of lamivudine and novel salts in the manufacture thereof
EP3351249A1 (en) 2010-01-27 2018-07-25 VIIV Healthcare Company Antiviral therapy
WO2011095987A1 (en) 2010-02-03 2011-08-11 Matrix Laboratories Ltd. Novel process for the preparation of cis-nucleoside derivative
US20110223131A1 (en) 2010-02-24 2011-09-15 Gilead Sciences, Inc. Antiviral compounds
CN102234269B (zh) * 2010-04-29 2015-09-16 重庆医药工业研究院有限责任公司 拉米夫定的工业化制备方法
WO2011141805A2 (en) 2010-05-14 2011-11-17 Lupin Limited An improved process for the manufacture of lamivudine
WO2011156594A2 (en) 2010-06-09 2011-12-15 Vaccine Technologies, Incorporated Therapeutic immunization in hiv infected subjects receiving stable antiretroviral treatment
HUE033378T2 (en) 2010-08-12 2017-11-28 Boehringer Ingelheim Int 6-Cycloalkyl-1,5-dihydro-pyrazolo [3,4-D] pyrimidin-4-one and their use as PDE9A inhibitors
US8809345B2 (en) 2011-02-15 2014-08-19 Boehringer Ingelheim International Gmbh 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders
US20130296562A1 (en) 2011-08-05 2013-11-07 Lupin Limited Stereoselective process for preparation of 1,3-oxathiolane nucleosides
WO2013168066A1 (en) 2012-05-05 2013-11-14 Lupin Limited An improved process for the manufacture of lamivudine form i.
CN103694231A (zh) * 2013-11-28 2014-04-02 安徽一帆香料有限公司 一种拉米夫定中间体hdms的合成制备方法
WO2016001907A1 (en) 2014-07-02 2016-01-07 Prendergast Patrick T Mogroside iv and mogroside v as agonist/stimulator/un-blocking agent for toll-like receptor 4 and adjuvant for use in human/animal vaccine and to stimulate immunity against disease agents.
AU2015287773B2 (en) 2014-07-11 2018-03-29 Gilead Sciences, Inc. Modulators of toll-like receptors for the treatment of HIV
US9675632B2 (en) 2014-08-26 2017-06-13 Enanta Pharmaceuticals, Inc. Nucleoside and nucleotide derivatives
MA42818A (fr) 2015-09-15 2018-07-25 Gilead Sciences Inc Modulateurs de récepteurs de type toll pour le traitement du vih
BR112018011085B1 (pt) 2015-12-02 2020-06-02 Merck Sharp & Dohme Corp. Composição farmacêutica compreendendo doravirina, fumarato de tenofovir desoproxila e lamivudina e processo para sua preparação
WO2018178722A1 (en) * 2017-03-31 2018-10-04 The University Of Liverpool Prodrug compositions

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4000137A (en) * 1975-06-10 1976-12-28 American Home Products Corporation Antitumor derivatives of periodate-oxidized nucleosides
JPS5259171A (en) * 1975-11-10 1977-05-16 Asahi Chem Ind Co Ltd Preparation of uracil derivatives
JPS6045196B2 (ja) * 1976-08-09 1985-10-08 株式会社興人 １−（２−テトラヒドロフリル）ウラシル類の製造方法
JPS5668674A (en) * 1979-11-08 1981-06-09 Shionogi & Co Ltd 5-fluorouracil derivative
JPS56167685A (en) * 1980-05-28 1981-12-23 Taiho Yakuhin Kogyo Kk 1- 2-tetrahydrothiophene-1,1-dioxide -5-fluorouracil and its preparation
JPS56169689A (en) * 1980-06-02 1981-12-26 Taiho Yakuhin Kogyo Kk 3-substituted-5-fluorouracil derivative and its preparation
JPS5738774A (en) * 1980-08-19 1982-03-03 Chugai Pharmaceut Co Ltd Uracil derivative and its preparation
SU1035023A1 (ru) * 1982-03-23 1983-08-15 Ордена Трудового Красного Знамени Институт Органической И Физической Химии Им.А.Е.Арбузова Способ получени 3-(тииранил-2-метил)-6-метилурацилов
DE3324769A1 (de) * 1983-07-08 1985-01-17 Bayer Ag, 5090 Leverkusen 5-aminomethyl-1,3-oxathiolane
NZ216172A (en) * 1985-05-15 1989-08-29 Wellcome Found Nucleosides and pharmaceutical compositions
CA1294960C (en) * 1986-10-24 1992-01-28 Thomas C. Malone 7-deazaguanines as immunomodulators
DE3712735A1 (de) * 1987-04-15 1988-11-10 Boehringer Mannheim Gmbh Neue pyrazolo(3,4-d)pyrimidine, verfahren zu ihrer herstellung und verwendung als arzneimittel
DE68923387T2 (de) * 1988-02-16 1996-01-25 Lilly Co Eli 2',3'-Dideoxy-2',2'-difluornucleoside.
NZ228645A (en) * 1988-04-11 1991-09-25 Iaf Biochem Int 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections
US5047407A (en) 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
US5204466A (en) 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds

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