WO1991006548A1 - Inhibitors of purine nucleoside phosphorylase - Google Patents

Inhibitors of purine nucleoside phosphorylase Download PDF

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Publication number
WO1991006548A1
WO1991006548A1 PCT/US1990/005756 US9005756W WO9106548A1 WO 1991006548 A1 WO1991006548 A1 WO 1991006548A1 US 9005756 W US9005756 W US 9005756W WO 9106548 A1 WO9106548 A1 WO 9106548A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
cyclo
amino
pyrrolo
pyrimidin
Prior art date
Application number
PCT/US1990/005756
Other languages
English (en)
French (fr)
Inventor
John A. Secrist, Iii
Mark David Erion
John A. Montgomery
Steven E. Ealick
Wayne C. Guida
Shri Niwas
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 US07/429,098 external-priority patent/US4985434A/en
Priority claimed from US07/429,097 external-priority patent/US5008270A/en
Priority claimed from US07/429,100 external-priority patent/US4985433A/en
Priority claimed from US07/429,099 external-priority patent/US5008265A/en
Application filed by Biocryst, Inc. filed Critical Biocryst, Inc.
Priority to CA002072123A priority Critical patent/CA2072123C/en
Priority to SU925011315A priority patent/RU2097384C1/ru
Priority to AU67125/90A priority patent/AU654264B2/en
Publication of WO1991006548A1 publication Critical patent/WO1991006548A1/en
Priority to FI921900A priority patent/FI103972B/fi
Priority to NO921679A priority patent/NO301423B1/no
Priority to LVP-93-342A priority patent/LV10100B/en

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

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  • 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)
PCT/US1990/005756 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase WO1991006548A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA002072123A CA2072123C (en) 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase
SU925011315A RU2097384C1 (ru) 1989-10-31 1990-10-12 Производные 2-амино-7-(chr2r3)-3н,5н-пирроло[3,2-d]-пиримидин-4-она, способы их получения и способ селективного ингибирования пролиферации т-лимфоцитов млекопитающего и не оказывающий воздействия на b-лимфоциты
AU67125/90A AU654264B2 (en) 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase
FI921900A FI103972B (fi) 1989-10-31 1992-04-28 Menetelmä puriininukleosidifosforylaasi-inhibiittorien valmistamiseksi
NO921679A NO301423B1 (no) 1989-10-31 1992-04-29 Analogifremgangsmåte for fremstilling av inhibitorer av purin nukleosid fosforylase
LVP-93-342A LV10100B (en) 1989-10-31 1993-05-14 Inhibitors of purine nucleoside phosphorylase

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
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
US429,099 1989-10-31
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
US429,098 1989-10-31
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
US429,100 1989-10-31
US429,097 1989-10-31
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
US44279889A 1989-11-29 1989-11-29
US442,798 1989-11-29

Publications (1)

Publication Number Publication Date
WO1991006548A1 true WO1991006548A1 (en) 1991-05-16

Family

ID=27541578

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/005756 WO1991006548A1 (en) 1989-10-31 1990-10-12 Inhibitors of purine nucleoside phosphorylase

Country Status (9)

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

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO1993021187A1 (en) * 1992-04-21 1993-10-28 Biocryst Pharmaceuticals, Inc. 7-DISUBSTITUTED-METHYL-4-OXO-3H^_,5H^_-PYRROLO[3,2-d^_]PYRIMIDINE AND PHARMACEUTICAL USES AND COMPOSITIONS CONTAINING THE SAME
WO1996011200A1 (en) * 1994-10-05 1996-04-18 Chiroscience Limited Purine and guanine compounds as inhibitors of pnp
WO1997012887A1 (en) * 1995-10-05 1997-04-10 Chiroscience Limited Purine and guanine derivatives as pnp inhibitors
WO1997012888A1 (en) * 1995-10-05 1997-04-10 Chiroscience Limited Purine and guanine derivatives
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
US6043365A (en) * 1997-05-29 2000-03-28 Novartis Ag Preparation of 2-amino-7-(1-substituted-2-hydroxyethyl)-3, 5-dihydropyrrolo[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
US8895556B2 (en) 2007-12-26 2014-11-25 Critical Outcome Technologies Inc. Compounds and method for treatment of cancer
US8987272B2 (en) 2010-04-01 2015-03-24 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9284275B2 (en) 2007-01-11 2016-03-15 Critical Outcome Technologies Inc. Inhibitor compounds and cancer treatment methods

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4496586B2 (ja) * 2000-01-24 2010-07-07 日産化学工業株式会社 キノリルアクリロニトリルの製造法及びその中間体
EP1539783B1 (en) * 2002-08-21 2011-04-13 Albert Einstein College Of Medicine Of Yeshiva University 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

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5988484A (ja) * 1982-11-09 1984-05-22 Takeda Chem Ind Ltd 新規７−デアザプリン誘導体
WO1988003142A2 (en) * 1986-10-24 1988-05-25 Warner-Lambert Company 7-deazaguanines as immunomodulators
US4921858A (en) * 1986-10-24 1990-05-01 Warner-Lambert Company 7-deazaguanines as immunomodulators
US4921872A (en) * 1987-02-11 1990-05-01 Bayer Aktiengesellschaft Acaricidal agents based on azomethines of 2,3-diaminomaleic acid nitrile
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
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
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1293727C (en) * 1986-08-26 1991-12-31 Catherine Rose Kostlan 9-deazaguanines
EP0460116B1 (en) * 1989-02-27 1997-08-27 Biocryst Pharmaceuticals Inc. 9-substituted-8-unsubstituted-9-deazaguanines

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5988484A (ja) * 1982-11-09 1984-05-22 Takeda Chem Ind Ltd 新規７−デアザプリン誘導体
WO1988003142A2 (en) * 1986-10-24 1988-05-25 Warner-Lambert Company 7-deazaguanines as immunomodulators
US4921858A (en) * 1986-10-24 1990-05-01 Warner-Lambert Company 7-deazaguanines as immunomodulators
US4921872A (en) * 1987-02-11 1990-05-01 Bayer Aktiengesellschaft Acaricidal agents based on azomethines of 2,3-diaminomaleic acid nitrile
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
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
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

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Journal of American Chemical Society, Vol. 75, by V. BOEKELHEIDE, et al. "Quinolizidine Derivatives. A study of the Reductive Cyclization of Some v-(2-pyridyl)-butyronitrides" See pp 3243-3248 (1953). *
Journal of Organic Chemistry, Vol. 40, No. 1, by JAMES A. PROFITT, et al. "A Reagent for the ,beta Reduction of Conjugated Nitriles" See pp 127-128 (1975). *
Journal of Organic Chemistry, Vol. 48, by MU-ILL LIM et al, "Synthesis of "9-Deazaguanosine" and other new pyrrolo (3.2-d) pyrimidine C-nucleosides". See pp 780-788 (1983). *
See also references of EP0500653A4 *
Tetrahedron Letters, Vol. 21, by MU - ILL LIM et al. "Synthesis of the pyrrolo (3,2-d) pyrimidine C-nucleoside isostere of Inosine" See pp 1013-1016 (1980). *
Tetrahedron Letters, Vol. 22, by MU - ILL LIM et al. "Synthesis of "9-Deazadenosine"; A new cytotoxic C-nucleoside Isostere of Adenosine" See pp 25-28 (1981). *

Cited By (17)

* 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
US5281708A (en) * 1992-02-03 1994-01-25 Warner-Lambert Company 9-Substituted-8-halo or -8-hydroxy-9-deazaguanines as inhibitors of PNP
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
WO1993021187A1 (en) * 1992-04-21 1993-10-28 Biocryst Pharmaceuticals, Inc. 7-DISUBSTITUTED-METHYL-4-OXO-3H^_,5H^_-PYRROLO[3,2-d^_]PYRIMIDINE AND PHARMACEUTICAL USES AND COMPOSITIONS CONTAINING THE SAME
WO1996011200A1 (en) * 1994-10-05 1996-04-18 Chiroscience Limited Purine and guanine compounds as inhibitors of pnp
US5736549A (en) * 1994-10-05 1998-04-07 Chiroscience Limited Hypoxanthine and guanine compounds
US5863921A (en) * 1995-10-05 1999-01-26 Darwin Discovery Limited Purine and guanine derivatives
WO1997012888A1 (en) * 1995-10-05 1997-04-10 Chiroscience Limited Purine and guanine derivatives
WO1997012887A1 (en) * 1995-10-05 1997-04-10 Chiroscience Limited Purine and guanine derivatives as pnp inhibitors
US5912252A (en) * 1995-10-05 1999-06-15 Darwin Discovery Limited Purine and guanine derivatives as PNP inhibitors
US6043365A (en) * 1997-05-29 2000-03-28 Novartis Ag Preparation of 2-amino-7-(1-substituted-2-hydroxyethyl)-3, 5-dihydropyrrolo[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
US9284275B2 (en) 2007-01-11 2016-03-15 Critical Outcome Technologies Inc. Inhibitor compounds and cancer treatment methods
US8895556B2 (en) 2007-12-26 2014-11-25 Critical Outcome Technologies Inc. Compounds and method for treatment of cancer
US8987272B2 (en) 2010-04-01 2015-03-24 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9422282B2 (en) 2010-04-01 2016-08-23 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9624220B2 (en) 2010-04-01 2017-04-18 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV

Also Published As

Publication number Publication date
LV10100A (lv) 1994-05-10
NO921679D0 (no) 1992-04-29
JPH05504551A (ja) 1993-07-15
NO301423B1 (no) 1997-10-27
FI921900A (fi) 1992-04-28
EP0500653A4 (en) 1995-08-23
CA2072123C (en) 2001-06-12
NO921679L (no) 1992-06-17
HU9201450D0 (en) 1992-09-28
FI103972B1 (fi) 1999-10-29
LV10100B (en) 1995-08-20
AU654264B2 (en) 1994-11-03
JP2866478B2 (ja) 1999-03-08
HUT61765A (en) 1993-03-01
FI921900A0 (fi) 1992-04-28
AU6712590A (en) 1991-05-31
EP0500653A1 (en) 1992-09-02
CA2072123A1 (en) 1991-05-01
FI103972B (fi) 1999-10-29

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