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KR970070015A - Phospholipid Derivatives of Acyclic Nucleosides and Their Preparation Method - Google Patents

Phospholipid Derivatives of Acyclic Nucleosides and Their Preparation Method Download PDF

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Publication number
KR970070015A
KR970070015A KR1019960011857A KR19960011857A KR970070015A KR 970070015 A KR970070015 A KR 970070015A KR 1019960011857 A KR1019960011857 A KR 1019960011857A KR 19960011857 A KR19960011857 A KR 19960011857A KR 970070015 A KR970070015 A KR 970070015A
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South Korea
Prior art keywords
saturated
alkyl group
unsaturated alkyl
carbon atoms
acyclovir
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KR1019960011857A
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Korean (ko)
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KR0170079B1 (en
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백우현
이규홍
신원섭
이재승
박재호
배건우
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김승호
보령제약 주식회사
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    • 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
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
    • 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

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 항바이러스성 약제로 유효한 하기 일반식(Ⅰ)의 신규한 아시클릭 뉴클레오시드의 인지질 유도체 및 약학적으로 허용되는 이들 염에 관한 것이다.The present invention relates to a phosphonic derivative of the novel acyclic nucleoside of the following general formula (I), which is effective as an antiviral agent, and pharmaceutically acceptable salts thereof.

상기 식에서, A는 산소 또는 황원자이고, R1은 탄소수가 6 내지 22개인 포화 또는 불포화 알킬기이고, R2는 탄소수가 2 내지 21개인 포화 또는 불포화 알킬기를 나타내며, B는 항바이러스성 아시클릭 뉴클레오시드로서 아시클로버, 간시클로버, 펜시클로버 잔기이다.Wherein R 1 is a saturated or unsaturated alkyl group having 6 to 22 carbon atoms, R 2 is a saturated or unsaturated alkyl group having 2 to 21 carbon atoms, B is an antiviral acyclic nucleotide As a seed, it is an asclover, a ginsey clover, and a pensyclover residue.

Description

아시클릭 뉴클레오시드의 인지질유도체 및 이의 제조방법Phospholipid Derivatives of Acyclic Nucleosides and Their Preparation Method

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

제1도는 단순포진 바이러스 타입-1으로 감염시킨 후에 본 발명에 의한 ACV-PCA를 투여한 경우 마우스의 생존률을 대조군과 비교하여 나타낸 그래프이고, 제2도는 단순포진 바이러스 타입-1으로 감염시킨 후에 본 발명에 의한 ACV-PTBA를 투여한 경우 마우스의 생존률을 대조군과 비교하여 나타낸 그래프이고, 제3도는 단순포진 바이러스 타입-1으로 감염시킨 후에 본 발명에 의한 ACV-PCA를 투여한 경우 마우스의 체중 변화를 대조군과 비교하여 나타낸 그래프이고, 제4도는 단순포진 바이러스 타입-1으로 감염시킨 후에 본 발명에 의한 ACV-PCA를 투여한 경우 마우스의 체중 변화를 대조군과 비교하여 나타낸 그래프이다.FIG. 1 is a graph showing the survival rate of mice treated with ACV-PCA according to the present invention after infecting with herpes simplex virus type-1 in comparison with the control group. FIG. FIG. 3 is a graph showing the survival rate of mice when ACV-PTBA according to the invention is administered, and FIG. 3 is a graph showing changes in body weight of mice when ACV-PCA according to the present invention is administered after infection with herpes simplex virus type- FIG. 4 is a graph showing changes in body weight of mice when ACV-PCA according to the present invention is administered after infection with herpes simplex virus type-1, in comparison with the control group.

Claims (5)

항바이러스제로 사용되는 하기 일반식(Ⅰ)의 아시클릭 뉴클레오시드의 인지질 복합체 및 약학적으로 허용되는 이들의 염.A phospholipid complex of an acyclic nucleoside of the general formula (I) and pharmaceutically acceptable salts thereof, which is used as an antiviral agent. (단, 상기 식에서, A는 산소 또는 황원자이고, R1은 탄소수가 6 내지 22개인 포화 또는 불포화 알킬기이고, R2는 탄소수가 2 내지 21개인 포화 또는 불포화 알킬기를 나타내며, B는 하기 일반식으로 표시되는 항바이러스성 아시클릭 뉴클레오시드로서;(However, the above formula, A is an oxygen or a sulfur atom, R 1 is a carbon atoms is 6 to 22, a saturated or unsaturated alkyl group, R 2 has a carbon number of 2 to 21 represents a a saturated or unsaturated alkyl group, B has the following formula As an indicated antiviral acyclic nucleoside; 여기서, Y는 수소원자 또는 CH2OH이고 Z는 탄소 또는 산소원자이다.)Wherein Y is a hydrogen atom or CH 2 OH and Z is a carbon or oxygen atom. 제1항에 있어서, R1이 탄소수 12 내지 20의 포화 또는 불포화 알킬기인 것을 특징으로 하는 화합물.The compound according to claim 1, wherein R 1 is a saturated or unsaturated alkyl group having 12 to 20 carbon atoms. 항바이러스제로 사용되는 아시클로버-5'-디포스페이트-rac-1-O-헥사데실-2-O-팔미토일글리세롤(ACACP-DL-PCA), 아시클로버-5'-디포스페이트-rac-1-S-옥타데실-2-O-팔미토일-1-티오글리세롤(ACVDP-DL-PTBA), 아시클로버-5'-디포스페이트-rac-1-O-옥타데실-2-O-팔미토일글리세롤-(ACVDP-DL-PBA), 아시클로버-5'-디포스페이트-rac-1-S-헥사데실-2-O-팔미토일-1-티오글리세롤(ACVDP-DL-PTCA), 또는 약학적으로 허용되는 이들의 염.1-O-hexadecyl-2-O-palmitoyl glycerol (ACACP-DL-PCA), acyclovir-5'-diphosphate-rac-1-S -Acetyl-2-O-palmitoyl-1-thioglycerol (ACVDP-DL-PTBA), acyclovir-5'- -DL-PBA), acyclovir-5'-diphosphate-rac-1-S-hexadecyl-2-O-palmitoyl-1-thioglycerol (ACVDP-DL- PTCA) salt. 제1항 내지 제3항 중의 어느 한 항에 있어서, 상기 염이 소디움염인 것을 특징으로 하는 화합물.4. A compound according to any one of claims 1 to 3, wherein said salt is a sodium salt. 제1항 내지 제4항 중의 어느 한 항의 화합물과 약제학적으로 허용가능한 담체 또는 부형제를 함유하는 포유류의 바이러스 감염 치료용 약제학적 조성물.A pharmaceutical composition for the treatment of a viral infection of a mammal containing a compound of any one of claims 1 to 4 and a pharmaceutically acceptable carrier or excipient. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960011857A 1996-04-19 1996-04-19 Phospholipid derivatives of acyclic nucleoside and their preparation KR0170079B1 (en)

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KR970070015A true KR970070015A (en) 1997-11-07
KR0170079B1 KR0170079B1 (en) 1999-02-01

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