HUP0301875A2 - Pyrrolo[2,3-d]pyrimidine nucleoside analogs - Google Patents

Pyrrolo[2,3-d]pyrimidine nucleoside analogs

Info

Publication number
HUP0301875A2
HUP0301875A2 HU0301875A HUP0301875A HUP0301875A2 HU P0301875 A2 HUP0301875 A2 HU P0301875A2 HU 0301875 A HU0301875 A HU 0301875A HU P0301875 A HUP0301875 A HU P0301875A HU P0301875 A2 HUP0301875 A2 HU P0301875A2
Authority
HU
Hungary
Prior art keywords
group
atom
alkynyl
alkenyl
hydrogen
Prior art date
Application number
HU0301875A
Other languages
Hungarian (hu)
Inventor
Zbigniew Pietrzkowski
Robert Tam
Guangyi Wang
Original Assignee
Icn Pharmaceuticals, Inc.
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 Icn Pharmaceuticals, Inc. filed Critical Icn Pharmaceuticals, Inc.
Publication of HUP0301875A2 publication Critical patent/HUP0301875A2/en

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Classifications

    • 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
    • C07H19/14—Pyrrolo-pyrimidine radicals
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Transplantation (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)

Abstract

A találmány új (I) általános képletű, a ribofuranozil-csoport 4' és 5'helyzetű szénatomján helyettesített pirrolo[2,3-d)pirimidin nukleozid-származékokra és alkalmazásukra vonatkozik. Az (I) általános képletbenA jelentése oxigén- vagy kénatom vagy metiléncsoport; X jelentésehidrogénatom, amino- vagy hidroxicsoport; Y jelentése hidrogénatom,halogénatom vagy aminocsoport; Z jelentése hidrogén- vagy halogénatomvagy -R, -OH, -OR, -SH, -SR, -NH2, -NHR, -NR2, -CN, -C(O)NH2, -COOH, -COOR, -CH2NH2, -C(=NOH)NH2 vagy -C(=NH)NH2 képletű csoport, ahol Rjelentése alkil-, alkenil-, alkinil- vagy aralkilcsoport, R2 és R3jelentése egymástól függetlenül hidrogén- vagy fluoratom vagyhidroxicsoport; R4 jelentése hidrogénatom, alkil-, alkenil-, alkinil-vagy aralkilcsoport, ahol R4 adott esetben heteroatomot és/vagyfunkciós csoportot tartalmaz; R5 jelentése hidroxicsoport, -OP(O)(OH)2, -P(O)(OH)2 képletű vagy -OP(O)(OR')2 vagy -P(O)(OR')2általános képletű csoport, és R' jelentése védőcsoport, R5' jelentésealkil-, alkenil-, alkinil- vagy aralkilcsoport, ahol R5' legalább kétszénatomot tartalmaz és adott esetben heteroatomot és/vagy funkcióscsoportot tartalmaz. A vegyületek többek között rákellenes ésimmunmódosító hatással rendelkeznek, citotoxikus hatásuk azonbankisebb mértékű, mint az ismert nukleozidszármazékoké. ÓThe invention relates to new pyrrolo[2,3-d)pyrimidine nucleoside derivatives of formula (I) substituted on the 4' and 5' carbon atoms of the ribofuranosyl group and their use. In the general formula (I), A is an oxygen or sulfur atom or a methylene group; X represents a hydrogen atom, an amino or a hydroxy group; Y represents a hydrogen atom, a halogen atom or an amino group; Z is hydrogen or halogen or -R, -OH, -OR, -SH, -SR, -NH2, -NHR, -NR2, -CN, -C(O)NH2, -COOH, -COOR, -CH2NH2, - a group of the formula C(=NOH)NH2 or -C(=NH)NH2, where R means an alkyl, alkenyl, alkynyl or aralkyl group, R2 and R3 independently mean a hydrogen or fluorine atom or a hydroxy group; R 4 is a hydrogen atom, an alkyl, alkenyl, alkynyl or aralkyl group, where R 4 optionally contains a heteroatom and/or a functional group; R5 is hydroxy, -OP(O)(OH)2, -P(O)(OH)2 or -OP(O)(OR')2 or -P(O)(OR')2 and R' is a protective group, R5' is an alkyl, alkenyl, alkynyl or aralkyl group, where R5' contains at least two carbon atoms and optionally a heteroatom and/or a functional group. Among other things, the compounds have anticancer and immunomodulating effects, but their cytotoxic effect is lower than that of known nucleoside derivatives. HE

HU0301875A 1999-08-27 2000-08-17 Pyrrolo[2,3-d]pyrimidine nucleoside analogs HUP0301875A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15123399P 1999-08-27 1999-08-27
PCT/US2000/022674 WO2001027114A1 (en) 1999-08-27 2000-08-17 PYRROLO[2,3-d]PYRIMIDINE NUCLEOSIDE ANALOGS

Publications (1)

Publication Number Publication Date
HUP0301875A2 true HUP0301875A2 (en) 2003-09-29

Family

ID=22537871

Family Applications (1)

Application Number Title Priority Date Filing Date
HU0301875A HUP0301875A2 (en) 1999-08-27 2000-08-17 Pyrrolo[2,3-d]pyrimidine nucleoside analogs

Country Status (18)

Country Link
EP (1) EP1212326A4 (en)
JP (1) JP2003511454A (en)
KR (1) KR20020092904A (en)
CN (1) CN1384834A (en)
AU (1) AU769578B2 (en)
BR (1) BR0013642A (en)
CA (1) CA2381297A1 (en)
HR (1) HRP20020163A2 (en)
HU (1) HUP0301875A2 (en)
IL (1) IL147908A0 (en)
MX (1) MXPA02001753A (en)
NO (1) NO20020931L (en)
PL (1) PL354094A1 (en)
RU (1) RU2002103501A (en)
SI (1) SI20819A (en)
SK (1) SK1772002A3 (en)
WO (1) WO2001027114A1 (en)
ZA (1) ZA200201567B (en)

Families Citing this family (21)

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US7638496B2 (en) 2000-02-15 2009-12-29 Valeant Pharmaceuticals North America Nucleoside analogs with carboxamidine modified monocyclic base
US6455508B1 (en) * 2000-02-15 2002-09-24 Kanda S. Ramasamy Methods for treating diseases with tirazole and pyrrolo-pyrimidine ribofuranosyl nucleosides
JP2003183283A (en) * 2001-12-18 2003-07-03 Takeda Chem Ind Ltd Condensed indole compound, method for producing the same and application of the same
US20050182252A1 (en) 2004-02-13 2005-08-18 Reddy K. R. Novel 2'-C-methyl nucleoside derivatives
CN101851241B (en) * 2010-07-02 2012-05-23 西安交通大学 Anti-tumor compound and preparation method and application thereof
US8871737B2 (en) 2010-09-22 2014-10-28 Alios Biopharma, Inc. Substituted nucleotide analogs
CN102286048A (en) * 2011-06-24 2011-12-21 吉林大学 4-amino-6-(3-(3-bromophenyl) phenyl-5-cyano-7-(beta-L-xylofuranose) pyrrolo [2,3-d] pyrimidine, like derivatives and application for preparing antitumor drugs
WO2013096680A1 (en) 2011-12-22 2013-06-27 Alios Biopharma, Inc. Substituted phosphorothioate nucleotide analogs
CN107459544B (en) 2011-12-22 2021-03-16 詹森生物制药有限公司 Substituted nucleosides, nucleotides and analogs thereof
USRE48171E1 (en) 2012-03-21 2020-08-25 Janssen Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
EP2828277A1 (en) 2012-03-21 2015-01-28 Vertex Pharmaceuticals Incorporated Solid forms of a thiophosphoramidate nucleotide prodrug
US9441007B2 (en) 2012-03-21 2016-09-13 Alios Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
WO2013142157A1 (en) 2012-03-22 2013-09-26 Alios Biopharma, Inc. Pharmaceutical combinations comprising a thionucleotide analog
CN114404427A (en) 2014-02-13 2022-04-29 配体药物公司 Prodrug compound and use thereof
JP2017520545A (en) 2014-07-02 2017-07-27 リガンド・ファーマシューティカルズ・インコーポレイテッド Prodrug compounds and their use
AR104326A1 (en) * 2015-05-04 2017-07-12 Lilly Co Eli 5-SUBSTITUTED NUCLEOSID COMPOUNDS
US10953029B2 (en) * 2015-09-23 2021-03-23 Merck Sharp & Dohme Corp. 4′-Substituted nucleoside reverse transcriptase inhibitors and preparations thereof
CN111788196A (en) 2018-01-09 2020-10-16 配体药物公司 Acetal compounds and their therapeutic use
CA3067434A1 (en) * 2018-05-15 2019-11-21 Illumina, Inc. Compositions and methods for chemical cleavage and deprotection of surface-bound oligonucleotides
CN114072407A (en) 2019-04-02 2022-02-18 阿里戈斯治疗公司 Compounds targeting PRMT5
KR102639275B1 (en) * 2021-06-08 2024-02-21 퓨쳐메디신 주식회사 Nucleoside derivative having kinase multiple target inhibiting activity and pharmaceutical composition for preventing and treating cancer comprising the same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988338A (en) * 1974-04-24 1976-10-26 Wisconsin Alumni Research Foundation 4-Substituted amino-2-substituted thio-pyrrolo-[2,3-d]pyrimidine derivatives
US4892865A (en) * 1987-12-01 1990-01-09 The Regents Of The University Of Michigan Pyrrolo[2,3-d]pyrimidine nucleosides as antiviral agents
US5674998A (en) * 1989-09-15 1997-10-07 Gensia Inc. C-4' modified adenosine kinase inhibitors
EP0684953A4 (en) * 1993-02-03 1999-12-22 Gensia Inc Adenosine kinase inhibitors comprising lyxofuranosyl derivatives.
US5665721A (en) * 1995-06-07 1997-09-09 Abbott Laboratories Heterocyclic substituted cyclopentane compounds
BR9714349A (en) * 1996-10-16 2000-11-14 Icn Pharmaceuticals Purine L-nucleosides, their analogues and their uses

Also Published As

Publication number Publication date
SI20819A (en) 2002-08-31
RU2002103501A (en) 2003-09-10
EP1212326A1 (en) 2002-06-12
CA2381297A1 (en) 2001-04-19
MXPA02001753A (en) 2002-10-23
NO20020931D0 (en) 2002-02-26
JP2003511454A (en) 2003-03-25
AU7061800A (en) 2001-04-23
AU769578B2 (en) 2004-01-29
HRP20020163A2 (en) 2004-02-29
BR0013642A (en) 2002-05-07
EP1212326A4 (en) 2003-08-20
ZA200201567B (en) 2003-07-30
PL354094A1 (en) 2003-12-29
SK1772002A3 (en) 2002-10-08
CN1384834A (en) 2002-12-11
KR20020092904A (en) 2002-12-12
WO2001027114A1 (en) 2001-04-19
IL147908A0 (en) 2002-08-14
NO20020931L (en) 2002-02-26

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