KR950000728A - 포스포네이트 뉴클레오티드 에스테르 유도체 - Google Patents

포스포네이트 뉴클레오티드 에스테르 유도체 Download PDF

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KR950000728A
KR950000728A KR1019940015180A KR19940015180A KR950000728A KR 950000728 A KR950000728 A KR 950000728A KR 1019940015180 A KR1019940015180 A KR 1019940015180A KR 19940015180 A KR19940015180 A KR 19940015180A KR 950000728 A KR950000728 A KR 950000728A
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ring
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KR1019940015180A
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히데아끼 다까시마
나오꼬 이노우에
마사루 우바사와
고오이찌 세끼야
싱고 야부우찌
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미야베 요시가즈
미쓰비시 가세이 가부시기가이샤
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65616Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

아래의 일반식(I)으로 나타내어지는 포스포네이트 뉴클레오티드 에스테르 유도체 또는 그 염.
위의 식에서 환 A :
R1,R2: H,할로겐 원자, OH, 아미노기 등, R3: 저급 알킬기, 치환 에틸기, R4: 치환 에틸기.
(효과) 본 발명의 포스포네이트 뉴클레오티드 에스테르 유도체는 우수한 항비루스 활성과 항종양 활성을 가지며, 더욱이 경구 투여가 가능하다.

Description

포스포네이트 뉴클레오티드 에스테르 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (12)

  1. 아래의 일반식(I)으로 나타내어지는 포스포네이트 뉴클레오티드 에스테르 유도체 또는 그 염.
    위의 일반식(I)에서, 환(環) A는 아래의 구조식을 나타내고,
    R1과 R2는 각각 독립하여 수소 원자, 할로겐 원자, 히드록실기, 메르캅토기, C6~C10의 아릴티오기 또는 아미노기를 나타내고, R3는 C1~C4의 알킬기 또는 플루오르 원자, C1~C4의 알콕시기, 페녹시기, C7~C10의 페닐알콕시기 및 C2~C5의 아실옥시기로부터 선택되는 하나 이상의 치환기를 가진 에틸기를 나타내며, R4는 플루오르 원자, C1~C4의 알콕시기, 페녹시기, C7~C10의 페닐알콕시기 및 C2~C5의 아실옥시기로부터 선택되는 하나 이상의 치환기를 가진 에틸기를 나타내고, X,Y 및 Z는 각각 독립하여 메틴기 또는 질소원자를 나타낸다.
  2. 제1항에 있어서, 환 A가 아래의 구조식인 화합물.
    위의 식에서 R1과 R2는 제1항에서 정의한 바와 같다.
  3. 제1항에 있어서, 환 A가 아래의 구조식인 화합물.
    위의 식에서 R1은 수소 원자, 히드록실기, 메르캅토기, 톨릴티오기 또는 아미노기를 나타내고, R2는 수소 원자, 염소 원자, 요오드 원자, 히드록실기 또는 아미노기를 나타낸다.
  4. 제1항에 있어서, 환 A가 아래의 구조식인 화합물.
    위의 식에서 R1은 아미노기를 나타내고, R2는 수소 원자를 나타낸다.
  5. 제1항에 있어서, 환 A가 아래의 구조식인 화합물.
    위의 식에서 R1과 R2는 아미노기를 나타낸다.
  6. 제1항 내지 제5항에 있어서, R3가 C1~C3의 알킬기, 2,2,2-트리플루오로에틸기 또는 C1~C3의 알콕시기, 페녹시기, C7~C10의 페닐알콕시기 및 C2~C5의 아실옥시기로부터 선택되는 치환기를 하나 가진 에틸기인 화합물.
  7. 제1항 내지 제5항에 있어서, R3가 C1~C3의 알킬기 또는 2,2,2-트리플루오로에틸기인 화합물.
  8. 제1항 내지 제7항에 있어서, R4가 2,2,2-트리플루오로에틸기 또는 C1~C3의 알콕시기, 페녹시기, C7~C10의 페닐알콕시기 및 C2~C5의 아실옥시기로부터 선택되는 치환기를 하나 가진 에틸기인 화합물.
  9. 제1항 내지 제7항에 있어서, R4가 2,2,2-트리플루오로에틸기인 화합물.
  10. 제1항 내지 제9항에 있어서, X 및 Z가 질소 원자인 화합물.
  11. 제1항 내지 제10항에 기재된 화합물 및 약학적으로 허용되는 담체를 함유하여서 되는 의약 조성물.
  12. 제1항 내지 제10항에 기재된 화합물을 유효성분으로 하는 항비루스제.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940015180A 1993-06-29 1994-06-29 포스포네이트뉴클레오티드에스테르유도체 KR100358327B1 (ko)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR970015804A (ko) * 1995-09-28 1997-04-28 이웅열 저수축 나일론 6 필라멘트사 및 그의 제조방법

Families Citing this family (91)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2001401A1 (en) * 1988-10-25 1990-04-25 Claude Piantadosi Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions
EP0702556B1 (en) * 1993-06-10 2002-10-23 Wake Forest University (phospho)lipids for combatting hepatitis b virus infection
US5798340A (en) 1993-09-17 1998-08-25 Gilead Sciences, Inc. Nucleotide analogs
US5656745A (en) * 1993-09-17 1997-08-12 Gilead Sciences, Inc. Nucleotide analogs
EP0719274A1 (en) * 1993-09-17 1996-07-03 Gilead Sciences, Inc. Method for dosing therapeutic compounds
WO1996006620A2 (en) 1994-08-29 1996-03-07 Wake Forest University Lipid analogs for treating viral infections
US7135584B2 (en) 1995-08-07 2006-11-14 Wake Forest University Lipid analogs for treating viral infections
US6197775B1 (en) * 1995-06-15 2001-03-06 Mitsubishi Chemical Corporation Phosphonate nucleotide derivatives
DE19540798A1 (de) * 1995-11-02 1997-05-07 Hoechst Ag Alkylxanthinphosphonate und Alkylxanthinphosphinoxide und deren Verwendung als Arzneimittel
TW369536B (en) * 1996-01-18 1999-09-11 Mitsubishi Chem Corp Phosphonate nucleotide compounds
US5922695A (en) * 1996-07-26 1999-07-13 Gilead Sciences, Inc. Antiviral phosphonomethyoxy nucleotide analogs having increased oral bioavarilability
WO1998006726A1 (fr) 1996-08-13 1998-02-19 Mitsubishi Chemical Corporation Composes nucleotidiques a base de phosphonate
US6284748B1 (en) 1997-03-07 2001-09-04 Metabasis Therapeutics, Inc. Purine inhibitors of fructose 1,6-bisphosphatase
BR9811045A (pt) * 1997-07-25 2000-08-22 Gilead Sciences Inc Composição de análogo de nucleotìdeo e processo de sìntese
ZA986614B (en) 1997-07-25 1999-01-27 Gilead Sciences Nucleotide analog composition
DK1256584T3 (da) * 1997-07-25 2004-12-06 Gilead Sciences Inc Fremgangsmåde til fremstilling af adefovir-dipivoxil
US5935946A (en) * 1997-07-25 1999-08-10 Gilead Sciences, Inc. Nucleotide analog composition and synthesis method
PT1256584E (pt) * 1997-07-25 2004-12-31 Gilead Sciences Inc Processo para a preparacao de adefovir-dipivoxil
AU761267C (en) * 1998-09-09 2007-08-09 Metabasis Therapeutics, Inc. Novel heteroaromatic inhibitors of fructose 1,6-bisphosphatase
US7026469B2 (en) 2000-10-19 2006-04-11 Wake Forest University School Of Medicine Compositions and methods of double-targeting virus infections and cancer cells
CA2393410C (en) 1999-12-03 2011-10-11 Karl Y. Hostetler Phosphonate compounds
EP1914237B1 (en) 1999-12-03 2014-06-18 The Regents of The University of California Phosphonate ester antiviral compounds
JP2003519154A (ja) * 1999-12-22 2003-06-17 メタバシス・セラピューティクス・インコーポレイテッド 新規なビスアミダートホスホネートプロドラッグ
KR20020093824A (ko) * 2000-02-29 2002-12-16 미쯔비시 웰 파마 가부시키가이샤 포스포네이트 뉴클레오티드 화합물
CN1699383A (zh) 2000-03-08 2005-11-23 症变治疗公司 新的芳基果糖-1,6-二磷酸酶抑制剂
US7563774B2 (en) 2000-06-29 2009-07-21 Metabasis Therapeutics, Inc. Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes
US7309696B2 (en) 2000-10-19 2007-12-18 Wake Forest University Compositions and methods for targeting cancer cells
MY141789A (en) * 2001-01-19 2010-06-30 Lg Chem Investment Ltd Novel acyclic nucleoside phosphonate derivatives, salts thereof and process for the preparation of the same.
US20030114467A1 (en) * 2001-06-21 2003-06-19 Shakespeare William C. Novel pyrazolo- and pyrrolo-pyrimidines and uses thereof
WO2003028737A1 (en) * 2001-08-30 2003-04-10 Mitsubishi Pharma Corporation Anti-viral agents and in-vitro method for the identification of candidates able to inhibit binding of polymerase to epsilon
US7551837B2 (en) 2001-08-31 2009-06-23 Thomson Licensing Sequence counter for an audio visual stream
KR20050044587A (ko) * 2001-12-07 2005-05-12 미쯔비시 웰 파마 가부시키가이샤 B형 간염 바이러스 감염 치료용 포스포네이트뉴클레오타이드 유사체의 용도
BR0309557A (pt) 2002-04-26 2005-03-01 Gilead Sciences Inc Inibidores da transcriptase reversa não nucleosìdeos
JP4476811B2 (ja) 2002-05-13 2010-06-09 メタバシス・セラピューティクス・インコーポレイテッド Pmeaおよびそのアナログの新規ホスホン酸系プロドラッグ
CA2485597C (en) * 2002-05-13 2013-07-02 Metabasis Therapeutics, Inc. Process for preparation of cyclic prodrugs of pmea and pmpa
CA2499889A1 (en) * 2002-09-26 2004-04-08 Lg Life Sciences Ltd. (+)-trans-isomers of (1-phosphonomethoxy-2-alkylcyclopropyl) methyl nucleoside derivatives, process for the preparation of stereoisomers thereof, and use of antiviral agents thereof
WO2004041837A1 (en) * 2002-10-31 2004-05-21 Metabasis Therapeutics, Inc. Novel cytarabine monophosphate prodrugs
ATE398455T1 (de) 2003-01-14 2008-07-15 Gilead Sciences Inc Zusammensetzungen und verfahren zur antiviralen kombinationstherapie
WO2004096285A2 (en) 2003-04-25 2004-11-11 Gilead Sciences, Inc. Anti-infective phosphonate conjugates
US7407965B2 (en) 2003-04-25 2008-08-05 Gilead Sciences, Inc. Phosphonate analogs for treating metabolic diseases
WO2005002626A2 (en) * 2003-04-25 2005-01-13 Gilead Sciences, Inc. Therapeutic phosphonate compounds
US7470724B2 (en) 2003-04-25 2008-12-30 Gilead Sciences, Inc. Phosphonate compounds having immuno-modulatory activity
AU2004233897A1 (en) 2003-04-25 2004-11-11 Gilead Sciences, Inc. Kinase inhibitor phosphonate conjugates
US7432261B2 (en) 2003-04-25 2008-10-07 Gilead Sciences, Inc. Anti-inflammatory phosphonate compounds
US7427636B2 (en) 2003-04-25 2008-09-23 Gilead Sciences, Inc. Inosine monophosphate dehydrogenase inhibitory phosphonate compounds
US7452901B2 (en) 2003-04-25 2008-11-18 Gilead Sciences, Inc. Anti-cancer phosphonate analogs
EA014685B1 (ru) 2003-04-25 2010-12-30 Джилид Сайэнс, Инк. Фосфонатсодержащие антивирусные соединения (варианты) и фармацевтическая композиция на их основе
US20050080053A1 (en) * 2003-08-29 2005-04-14 Biocryst Pharmaceuticals, Inc. Nucleosides, preparation thereof and use as inhibitors of RNA viral polymerases
US7432273B2 (en) 2003-10-24 2008-10-07 Gilead Sciences, Inc. Phosphonate analogs of antimetabolites
US7427624B2 (en) 2003-10-24 2008-09-23 Gilead Sciences, Inc. Purine nucleoside phosphorylase inhibitory phosphonate compounds
EP1678321A1 (en) 2003-10-24 2006-07-12 Gilead Sciences, Inc. Methods and compositions for identifying therapeutic compounds
GB0326168D0 (en) * 2003-11-10 2003-12-17 Arrow Therapeutics Ltd Chemical compounds
WO2005051298A2 (en) 2003-11-19 2005-06-09 Metabasis Therapeutics, Inc. Novel phosphorus-containing thyromimetics
NZ547907A (en) 2003-12-22 2010-07-30 Gilead Sciences Inc 4'-Substituted carbovir-and abacavir-derivatives as well as related compounds with HIV and HCV antiviral activity
AR048021A1 (es) * 2004-02-17 2006-03-22 Anadys Pharmaceuticals Inc Derivados nucleosido fosfonato utiles en el tratamiento de infecciones de hiv.
CN1964967B (zh) 2004-06-08 2014-04-16 症变治疗公司 路易斯酸介导的环状酯的合成
UA88313C2 (ru) 2004-07-27 2009-10-12 Гилиад Сайенсиз, Инк. Фосфонатные аналоги соединений ингибиторов вич
CN101005847A (zh) * 2004-08-18 2007-07-25 症变治疗公司 果糖1,6-双磷酸酶的新颖噻唑类抑制剂
US8642577B2 (en) 2005-04-08 2014-02-04 Chimerix, Inc. Compounds, compositions and methods for the treatment of poxvirus infections
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
WO2007014491A1 (fr) * 2005-08-03 2007-02-08 Beijing Fu Kang Ren Bio-Pharm Tech.Co.Ltd. Phosphonates de nucléotides acycliques et leur utilisation dans des agents antiviraux
WO2007058927A1 (en) 2005-11-11 2007-05-24 The Scripps Research Institute Histone deacetylase inhibitors as therapeutics for neurological diseases
KR20090026216A (ko) 2006-07-07 2009-03-11 길리애드 사이언시즈, 인코포레이티드 항바이러스 포스피네이트 화합물
US7842672B2 (en) 2006-07-07 2010-11-30 Gilead Sciences, Inc. Phosphonate inhibitors of HCV
KR20190126460A (ko) 2007-02-09 2019-11-11 메타베이시스 테라퓨틱스, 인크. 글루카곤 수용체의 길항제
CN101940571A (zh) 2007-04-13 2011-01-12 南方研究所 抗血管生成剂和使用方法
MX2010001784A (es) 2007-08-13 2010-03-15 Metabasis Therapeutics Inc Activadores novedosos de la glucocinasa.
EP2254582B1 (en) 2008-01-25 2016-01-20 Chimerix, Inc. Methods of treating viral infections
TWI444384B (zh) * 2008-02-20 2014-07-11 Gilead Sciences Inc 核苷酸類似物及其在治療惡性腫瘤上的用途
EA018308B1 (ru) 2008-07-08 2013-07-30 Джилид Сайэнс, Инк. Соли соединений ингибиторов вич
PL2799428T3 (pl) 2008-08-13 2017-05-31 Metabasis Therapeutics, Inc. Antagoniści glukagonu
WO2010078430A1 (en) 2008-12-30 2010-07-08 Arqule, Inc. Substituted 1h-pyrazolo[3,4-d]pyrimidine-6-amine compounds
US8343961B2 (en) 2009-03-31 2013-01-01 Arqule, Inc. Substituted heterocyclic compounds
WO2011011519A1 (en) 2009-07-21 2011-01-27 Chimerix, Inc. Compounds, compositions and methods for treating ocular conditions
WO2011100698A2 (en) 2010-02-12 2011-08-18 Chimerix, Inc. Methods of treating viral infection
WO2011133963A2 (en) * 2010-04-23 2011-10-27 University Of Southern California Tyrosine-based prodrugs of antiviral agents
EP2563367A4 (en) 2010-04-26 2013-12-04 Chimerix Inc METHODS OF TREATING RETROVIRAL INFECTIONS AND ASSOCIATED DOSAGE REGIMES
KR101880724B1 (ko) 2010-12-10 2018-08-17 시그마팜 래보러토리즈, 엘엘씨 경구 활성 뉴클레오티드 유사체 또는 경구 활성 뉴클레오티드 유사체 전구약물의 고 안정성 조성물
US9550803B2 (en) 2011-05-06 2017-01-24 University Of Southern California Method to improve antiviral activity of nucleotide analogue drugs
ES2874774T3 (es) 2011-12-22 2021-11-05 Geron Corp Análogos de guanina como sustratos de telomerasa y afectores de la longitud de los telómeros
CN102786549B (zh) * 2012-08-13 2013-07-03 洛阳聚慧投资股份有限公司 一组具有抑制hiv-1病毒复制活性的替诺福韦双酯化合物、制备方法及其药物用途
LT2970346T (lt) 2013-03-15 2018-11-26 The Regents Of The University Of California Acikliniai nukleozido fosfonato diesteriai
EP3105238A4 (en) 2014-02-13 2017-11-08 Ligand Pharmaceuticals, Inc. Prodrug compounds and their uses
CN103819472A (zh) * 2014-03-18 2014-05-28 福建天泉药业股份有限公司 缬恩替卡韦酸式加成盐及其制备方法
EP3154956A4 (en) 2014-06-12 2018-01-17 Ligand Pharmaceuticals, Inc. Glucagon antagonists
WO2016003812A1 (en) 2014-07-02 2016-01-07 Ligand Pharmaceuticals, Inc. Prodrug compounds and uses therof
RS63250B1 (sr) * 2014-09-15 2022-06-30 Univ California Nukleotidni analozi
US10377782B2 (en) 2015-09-15 2019-08-13 The Regents Of The University Of California Nucleotide analogs
PL3661937T3 (pl) 2017-08-01 2021-12-20 Gilead Sciences, Inc. Formy krystaliczne ((s)-((((2r,5r)-5-(6-amino-9h-puryn-9-ylo)-4-fluoro-2,5-dihydrofuran-2-ylo)oksy)metylo)(fenoksy)fosforylo)-l-alaninianu etylu (gs-9131) do leczenia zakażeń wirusowych
CN111788196A (zh) 2018-01-09 2020-10-16 配体药物公司 缩醛化合物及其治疗用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0481214B1 (en) * 1990-09-14 1998-06-24 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Prodrugs of phosphonates
GB9026164D0 (en) * 1990-12-01 1991-01-16 Beecham Group Plc Pharmaceuticals
TW369536B (en) * 1996-01-18 1999-09-11 Mitsubishi Chem Corp Phosphonate nucleotide compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR970015804A (ko) * 1995-09-28 1997-04-28 이웅열 저수축 나일론 6 필라멘트사 및 그의 제조방법

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