CA2387357A1 - Derivatives of pyrazolo[4,3-d]pyrimidin-7-ones which inhibit cyclic guanosine 3',5'-monophosphate phosphodiesterase - Google Patents

Derivatives of pyrazolo[4,3-d]pyrimidin-7-ones which inhibit cyclic guanosine 3',5'-monophosphate phosphodiesterase Download PDF

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CA2387357A1
CA2387357A1 CA002387357A CA2387357A CA2387357A1 CA 2387357 A1 CA2387357 A1 CA 2387357A1 CA 002387357 A CA002387357 A CA 002387357A CA 2387357 A CA2387357 A CA 2387357A CA 2387357 A1 CA2387357 A1 CA 2387357A1
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Prior art keywords
cyclic guanosine
pyrazolo
pyrimidin
ones
derivatives
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CA002387357A
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French (fr)
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CA2387357C (en
Inventor
Mark Edward Bunnage
Keith Michael Devries
Laurence James Harris
Philip Charles Levett
John Paul Mathias
Joanna Teresa Negri
Stephen Derek Albert Street
Albert Shaw Wood
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Pfizer Inc
Original Assignee
Pfizer, Inc.
Mark Edward Bunnage
Keith Michael Devries
Laurence James Harris
Philip Charles Levett
John Paul Mathias
Joanna Teresa Negri
Stephen Derek Albert Street
Albert Shaw Wood
Pfizer Limited
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Priority claimed from GBGB9924063.2A external-priority patent/GB9924063D0/en
Priority claimed from GB0018656A external-priority patent/GB0018656D0/en
Application filed by Pfizer, Inc., Mark Edward Bunnage, Keith Michael Devries, Laurence James Harris, Philip Charles Levett, John Paul Mathias, Joanna Teresa Negri, Stephen Derek Albert Street, Albert Shaw Wood, Pfizer Limited filed Critical Pfizer, Inc.
Publication of CA2387357A1 publication Critical patent/CA2387357A1/en
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Publication of CA2387357C publication Critical patent/CA2387357C/en
Anticipated expiration legal-status Critical
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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    • 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

Abstract

Compounds of formula (I) wherein R1, R2, R4 and R13 are as defined or a pharmaceutically or veterinarily acceptable salt or polymorph thereof, or a pharmaceutically or veterinarily acceptable solvate or pro-drug thereof: are potent and selective inhibitors of type 5 cyclic guanosine 3', 5'-monophosphate phosphodiesterase (cGMP PDE5) and have utility in the treatment of, inter alia, male erectile dysfunction (MED) and female sexual dysfunction (FSD).
CA002387357A 1999-10-11 2000-10-11 Derivatives of pyrazolo[4,3-d]pyrimidin-7-ones which inhibit cyclic guanosine 3',5'-monophosphate phosphodiesterase Expired - Fee Related CA2387357C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GBGB9924063.2A GB9924063D0 (en) 1999-10-11 1999-10-11 Pharmaceutically active compounds
GB9924063.2 1999-10-11
GB0018656.9 2000-07-28
GB0018656A GB0018656D0 (en) 2000-07-28 2000-07-28 Pharmaceutically active compounds
PCT/IB2000/001457 WO2001027113A2 (en) 1999-10-11 2000-10-11 PYRAZOLO `4,3-d! PYRIMIDINE DERIVATIVES

Publications (2)

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CA2387357A1 true CA2387357A1 (en) 2001-04-19
CA2387357C CA2387357C (en) 2007-10-02

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CA002387357A Expired - Fee Related CA2387357C (en) 1999-10-11 2000-10-11 Derivatives of pyrazolo[4,3-d]pyrimidin-7-ones which inhibit cyclic guanosine 3',5'-monophosphate phosphodiesterase

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US (4) US6677335B1 (en)
EP (1) EP1220856B1 (en)
JP (1) JP3834236B2 (en)
KR (1) KR100549152B1 (en)
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AP (1) AP1238A (en)
AT (1) ATE284404T1 (en)
AU (1) AU779065B2 (en)
BG (1) BG106678A (en)
BR (1) BR0014698A (en)
CA (1) CA2387357C (en)
CO (1) CO5251477A1 (en)
CR (2) CR6617A (en)
CU (1) CU23198A3 (en)
CZ (1) CZ20021158A3 (en)
DE (1) DE60016615T2 (en)
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DZ (1) DZ3220A1 (en)
EA (1) EA004982B1 (en)
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HK (3) HK1050367A1 (en)
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HU (1) HUP0203450A3 (en)
IL (2) IL149026A0 (en)
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MA (1) MA26825A1 (en)
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