CA2072123A1 - Inhibitors of purine nucleoside phosphorylase - Google Patents

Inhibitors of purine nucleoside phosphorylase

Info

Publication number
CA2072123A1
CA2072123A1 CA002072123A CA2072123A CA2072123A1 CA 2072123 A1 CA2072123 A1 CA 2072123A1 CA 002072123 A CA002072123 A CA 002072123A CA 2072123 A CA2072123 A CA 2072123A CA 2072123 A1 CA2072123 A1 CA 2072123A1
Authority
CA
Canada
Prior art keywords
alkyl
inhibitors
purine nucleoside
nucleoside phosphorylase
optionally substituted
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.)
Granted
Application number
CA002072123A
Other languages
French (fr)
Other versions
CA2072123C (en
Inventor
John A. Secrist, Iii
Mark D. Erion
John A. Montgomery
Steven E. Ealick
Wayne C. Guida
Shri Niwas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Biocryst Pharmaceuticals Inc
Original Assignee
BioCryst 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
Priority claimed from US07/429,100 external-priority patent/US4985433A/en
Priority claimed from US07/429,099 external-priority patent/US5008265A/en
Priority claimed from US07/429,098 external-priority patent/US4985434A/en
Priority claimed from US07/429,097 external-priority patent/US5008270A/en
Application filed by BioCryst Inc filed Critical BioCryst Inc
Publication of CA2072123A1 publication Critical patent/CA2072123A1/en
Application granted granted Critical
Publication of CA2072123C publication Critical patent/CA2072123C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Disclosed is a compound containing a 2-amino-7-(R)-3H,5H-pyrrolo[3,2-a]pyrimidin-4-one wherein K is cyclohexeny cyclohexyl, or -CH2-R1, and wherein R1 is an optionally substituted heteroalicyclic, pyridinyl or alicyclic group. Also dis-closed is a compound of formula (I), wherein R1 is H, NH2, or OCH3, R2 is an optionally substituted cyclic group of 5-carbon atoms optionally containing one or more heteroatoms, R3 and R4 are independently H or C1-4 alkyl, m is 0-4, n is 0-6, p is 0-1, X is CN, CSNH2, PO(OH)2, COOH, SO2NH2, NH2, OH CNHNH2, tetrazole, or triazole, COR5 where R5, C1-4 alkyl, CF3, NH2, or OC1-4 alkyl, and Y is O or NH.
CA002072123A 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase Expired - Fee Related CA2072123C (en)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
US07/429,100 US4985433A (en) 1989-10-31 1989-10-31 2-amino-7-(pyridinylmethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same
US07/429,099 US5008265A (en) 1989-10-31 1989-10-31 2-amino-7-(alicyclomethyl)-3H,5H,-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same
US429,099 1989-10-31
US429,098 1989-10-31
US07/429,098 US4985434A (en) 1989-10-31 1989-10-31 7-substituted derivatives of 2-amino-3H,5H-pyrrolo(3,2-d)pyrimidin-4-ones and pharamceutical uses and compositions containing the same
US07/429,097 US5008270A (en) 1989-10-31 1989-10-31 2-amino-7-(heterocyclomethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same
US429,097 1989-10-31
US429,100 1989-10-31
US44279889A 1989-11-29 1989-11-29
US442,798 1989-11-29
PCT/US1990/005756 WO1991006548A1 (en) 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase

Publications (2)

Publication Number Publication Date
CA2072123A1 true CA2072123A1 (en) 1991-05-01
CA2072123C CA2072123C (en) 2001-06-12

Family

ID=27541578

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002072123A Expired - Fee Related CA2072123C (en) 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase

Country Status (9)

Country Link
EP (1) EP0500653A4 (en)
JP (1) JP2866478B2 (en)
AU (1) AU654264B2 (en)
CA (1) CA2072123C (en)
FI (1) FI103972B (en)
HU (1) HUT61765A (en)
LV (1) LV10100B (en)
NO (1) NO301423B1 (en)
WO (1) WO1991006548A1 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5726311A (en) * 1989-11-29 1998-03-10 Biocryst Pharmaceuticals, Inc. 7-disubstituted-methyl-4-oxo-3H,5H-pyrrolo 3,2-d!pyrimidine and pharmaceutical uses and compositions containing the same
US5236926A (en) * 1992-02-03 1993-08-17 Warner-Lambert Company 9-substituted-8-halo or -8-hydroxy-9-deazaguanines as inhibitors or PNP for pharmaceutical compositions
RU94046387A (en) * 1992-04-21 1996-09-27 Биокрист Фармасьютикалз Derivatives of pyrimidine, method of their synthesis, pharmaceutical composition, its use and intermediate compounds
BR9509236A (en) * 1994-10-05 1997-10-21 Chiroscience Ltd Purine and guanine compounds as pnp inhibitors
GB9520363D0 (en) * 1995-10-05 1995-12-06 Chiroscience Ltd Compounds
GB9520364D0 (en) * 1995-10-05 1995-12-06 Chiroscience Ltd Compouundds
BR9809178A (en) * 1997-05-29 2000-08-01 Novartis Ag 2-amino-7- (1-substituted-2-hydroxyethyl) -3,5-dihydro-pyrrolo [3,2-d] pyrimidin-4-ones
US6174888B1 (en) 1998-05-28 2001-01-16 Novartis Ag 2-amino-7-(1-substituted-2-hydroxyethyl)-3,5-dihydropyrrolo[3,2-D]pyrimidin-4-ones
JP4496586B2 (en) * 2000-01-24 2010-07-07 日産化学工業株式会社 Process for producing quinolylacrylonitrile and its intermediate
CN100379750C (en) * 2002-08-21 2008-04-09 阿尔伯爱因斯坦医科叶希瓦大学 Inhibitors of nucleoside phosphorylases and nucleosidases
NZ523970A (en) * 2003-02-04 2005-02-25 Ind Res Ltd Process for preparing inhibitors of nucleoside phoshorylases and nucleosidases
CA2710039C (en) 2007-12-26 2018-07-03 Critical Outcome Technologies, Inc. Semicarbazones, thiosemicarbazones and related compounds and methods for treatment of cancer
WO2010006438A1 (en) 2008-07-17 2010-01-21 Critical Outcome Technologies Inc. Thiosemicarbazone inhibitor compounds and cancer treatment methods
US8987272B2 (en) 2010-04-01 2015-03-24 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5988484A (en) * 1982-11-09 1984-05-22 Takeda Chem Ind Ltd Novel 7-deazapurine derivative
CA1293727C (en) * 1986-08-26 1991-12-31 Catherine Rose Kostlan 9-deazaguanines
US4921858A (en) * 1986-10-24 1990-05-01 Warner-Lambert Company 7-deazaguanines as immunomodulators
CA1294960C (en) * 1986-10-24 1992-01-28 Thomas C. Malone 7-deazaguanines as immunomodulators
DE3726044A1 (en) * 1987-02-11 1988-08-25 Bayer Ag ACARICIDES ON THE BASIS OF AZOMETHINE DERIVATIVES AND AZOMETHINE OF 2,3-DIAMINOMALEAINSAURENITRILE
US4927830A (en) * 1988-04-08 1990-05-22 The Regents Of The University Of Michigan Acyclic pyrrolo[2,3-D]pyrimidine analogs as antiviral agents
JP2760364B2 (en) * 1989-02-27 1998-05-28 バイオクライシス・ファーマシューティカルズ、インコーポレイテッド 9-substituted-8-unsubstituted-9-deazaguanines
US4985434A (en) * 1989-10-31 1991-01-15 Biocryst, Inc. 7-substituted derivatives of 2-amino-3H,5H-pyrrolo(3,2-d)pyrimidin-4-ones and pharamceutical uses and compositions containing the same
US4985433A (en) * 1989-10-31 1991-01-15 Biocryst, Inc. 2-amino-7-(pyridinylmethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same

Also Published As

Publication number Publication date
LV10100A (en) 1994-05-10
EP0500653A1 (en) 1992-09-02
FI103972B1 (en) 1999-10-29
HUT61765A (en) 1993-03-01
FI921900A0 (en) 1992-04-28
LV10100B (en) 1995-08-20
WO1991006548A1 (en) 1991-05-16
AU654264B2 (en) 1994-11-03
AU6712590A (en) 1991-05-31
NO301423B1 (en) 1997-10-27
JP2866478B2 (en) 1999-03-08
FI921900A (en) 1992-04-28
EP0500653A4 (en) 1995-08-23
NO921679L (en) 1992-06-17
HU9201450D0 (en) 1992-09-28
CA2072123C (en) 2001-06-12
FI103972B (en) 1999-10-29
NO921679D0 (en) 1992-04-29
JPH05504551A (en) 1993-07-15

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