WO2005041957A1 - Derives d'oxindole et leur utilisation comme inhibiteurs de la phosphodiesterase de type 2 - Google Patents

Derives d'oxindole et leur utilisation comme inhibiteurs de la phosphodiesterase de type 2 Download PDF

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Publication number
WO2005041957A1
WO2005041957A1 PCT/IB2004/003404 IB2004003404W WO2005041957A1 WO 2005041957 A1 WO2005041957 A1 WO 2005041957A1 IB 2004003404 W IB2004003404 W IB 2004003404W WO 2005041957 A1 WO2005041957 A1 WO 2005041957A1
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WO
WIPO (PCT)
Prior art keywords
methyl
ester
pharmaceutically acceptable
prodrug
pde2
Prior art date
Application number
PCT/IB2004/003404
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English (en)
Inventor
Robert James Chambers
Kelvin T. Lam
Original Assignee
Pfizer Products 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 Pfizer Products Inc. filed Critical Pfizer Products Inc.
Publication of WO2005041957A1 publication Critical patent/WO2005041957A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • a PDE2 inhibitor useful in the present invention is a compound that inhibits PDE2 and preferably has an IC 50 against human recombinant or purified PDE2 of less than about 5.0 ⁇ M.
  • the IC 50 value of the PDE2 inhibitor is less than about 1.0 ⁇ M, more preferably about 0.2 ⁇ M or less.
  • Preferred PDE2 inhibitors of the present invention do not significantly inhibit, i.e.
  • PDE2 Binding Assay The activity of the test substances on human recombinant produced or isolated PDE2, and other PDE's is determined using the [ 3 H]cAMP scintillation proximity assay (SPA) kits from Amersham International (Little Chalfont, England). The SPA assays were performed using 96 well plates. The PDE SPA yttrium silicate beads (Amersham Biosciences®) bind preferentially to the linear nucleotide, GMP, compared to the cyclic nucleotide, cGMP.
  • SPA [ 3 H]cAMP scintillation proximity assay
  • IC 50 values of Compound 2 against purified PDE3 subtypes and PDE4 subtypes were all greater than 16.0 ⁇ M (data not shown).
  • PDE2 Expression in Normal and Diseased Human Tissues Expression profiling of PDE2 was performed against a panel of RNAs from normal and diseased human tissues. The RNA panel is composed of samples from three donors per tissue and each RT-PCR reaction is performed with cDNA represents 40 ng of total RNA. A standard curve was run using varying quantities of PDE2 plasmid to quantify the amount of cDNA copies per sample. The average expression levels per tissue were calculated and binned into high (> 10 4 copies), medium (10 3 to 10 4 copies), and low (>10 3 copies) expression categories. The data for this experiment is provided in Table II below and would support alternate sites of action for PDE2 inhibitors. Table II. PDE2 Human Tissue Expression

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des composés, des méthodes et des trousses de traitement d'états pathologiques ou de troubles dans lesquels la phosphodiestérase de type 2 (PDE2) est impliquée. Elle concerne des dérivés d'oxindole qui ont des applications thérapeutiques et comme inhibiteurs de la PDE2.
PCT/IB2004/003404 2003-10-29 2004-10-18 Derives d'oxindole et leur utilisation comme inhibiteurs de la phosphodiesterase de type 2 WO2005041957A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51540603P 2003-10-29 2003-10-29
US60/515,406 2003-10-29

Publications (1)

Publication Number Publication Date
WO2005041957A1 true WO2005041957A1 (fr) 2005-05-12

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PCT/IB2004/003404 WO2005041957A1 (fr) 2003-10-29 2004-10-18 Derives d'oxindole et leur utilisation comme inhibiteurs de la phosphodiesterase de type 2

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WO (1) WO2005041957A1 (fr)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012114222A1 (fr) * 2011-02-23 2012-08-30 Pfizer Inc. Imidazo[5,1-f][1,2,4] triazines pour traiter les troubles neurologiques
WO2014019979A1 (fr) 2012-07-31 2014-02-06 Boehringer Ingelheim International Gmbh 4-méthyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphtalènes
WO2015096651A1 (fr) 2013-12-23 2015-07-02 Merck Sharp & Dohme Corp. Composés pyrimidone carboxamide utilisés en tant qu'inhibiteurs de pde2
WO2015106032A1 (fr) 2014-01-08 2015-07-16 Intra-Cellular Therapies, Inc. Produits et compositions pharmaceutiques
WO2015164508A1 (fr) 2014-04-23 2015-10-29 Dart Neuroscience, Llc Composés de [1,2,4]triazolo[1,5-a]pyrimidin-7-yle substitués utilisables en tant qu'inhibiteurs de pde2
WO2016149058A1 (fr) 2015-03-17 2016-09-22 Merck Sharp & Dohme Corp. Composés de triazolyl pyrimidinone en tant qu'inhibiteurs de pde2
WO2016154081A1 (fr) 2015-03-26 2016-09-29 Merck Sharp & Dohme Corp. Composés pyrazolyle pyrimidinone utilisés en tant qu'inhibiteurs de pde2
WO2016209749A1 (fr) 2015-06-25 2016-12-29 Merck Sharp & Dohme Corp. Composés bicycliques pyrazolo/imidazolo substitués en tant qu'inhibiteurs de pde2
US9540379B2 (en) 2011-01-31 2017-01-10 Boehringer Ingelheim International Gmbh (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases
EP3156405A1 (fr) 2015-10-13 2017-04-19 Boehringer Ingelheim International GmbH Dérivés d'éther spirocycliques de pyrazolo [1,5-a] pyrimidine-3-carboxamide
US10105349B2 (en) 2014-12-06 2018-10-23 Intra-Cellular Therapies, Inc. Organic compounds
US10160762B2 (en) 2015-05-29 2018-12-25 Merck Sharp & Dohme Corp. 6-alkyl dihydropyrazolopyrimidinone compounds as PDE2 inhibitors
US10174037B2 (en) 2015-06-04 2019-01-08 Merck Sharp & Dohme Corp. Dihydropyrazolopyrimidinone compounds as PDE2 inhibitors
US10195201B2 (en) 2015-05-05 2019-02-05 Merck Sharp & Dohme Corp. Heteroaryl-pyrimidinone compounds as PDE2 inhibitors
US10239882B2 (en) 2014-11-05 2019-03-26 Dart Neuroscience (Cayman) Ltd. Substituted 5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine compounds as PDE2 inhibitors
US10287293B2 (en) 2015-07-01 2019-05-14 Merck Sharp & Dohme Corp. Bicyclic heterocyclic compounds as PDE2 inhibitors
US10285989B2 (en) 2015-05-15 2019-05-14 Merck Sharp & Dohme Corp. Pyrimidinone amide compounds as PDE2 inhibitors
US10300064B2 (en) 2014-12-06 2019-05-28 Intra-Cellular Therapies, Inc. Organic compounds
WO2019101970A1 (fr) 2017-11-23 2019-05-31 Oslo University Hospital Hf Traitement de la tachycardie
US10357481B2 (en) 2015-07-01 2019-07-23 Merck Sharp & Dohme Corp. Substituted triazolo bicyclic compounds as PDE2 inhibitors
CN112996492A (zh) * 2018-09-05 2021-06-18 阿姆斯特丹大学 Pde11或pde2抑制剂用于治疗帕金森氏疾病的用途
CN114890897A (zh) * 2022-05-31 2022-08-12 常州大学 一种pde2抑制剂内酯类衍生物及其制备方法

Citations (4)

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US4686224A (en) * 1984-10-31 1987-08-11 Pfizer Inc. Oxindole antiinflammatory agents
US4695571A (en) * 1984-08-24 1987-09-22 Pfizer Inc. Tricyclic oxindole antiinflammatory agents
US5057526A (en) * 1988-03-24 1991-10-15 Boehringer Mannheim Gmbh Pharmaceutically active pyridinyl substituted 5,7-dihydropyrrolo-[3,2-f]benzoxazole-6-ones
WO2002088139A1 (fr) * 2001-04-30 2002-11-07 Merck Patent Gmbh Derives de 6h-oxazolo[4,5-e]indole utilises en tant que ligands du recepteur nicotinique de l'acetylcholine et/ou ligands serotoninergiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4695571A (en) * 1984-08-24 1987-09-22 Pfizer Inc. Tricyclic oxindole antiinflammatory agents
US4686224A (en) * 1984-10-31 1987-08-11 Pfizer Inc. Oxindole antiinflammatory agents
US5057526A (en) * 1988-03-24 1991-10-15 Boehringer Mannheim Gmbh Pharmaceutically active pyridinyl substituted 5,7-dihydropyrrolo-[3,2-f]benzoxazole-6-ones
WO2002088139A1 (fr) * 2001-04-30 2002-11-07 Merck Patent Gmbh Derives de 6h-oxazolo[4,5-e]indole utilises en tant que ligands du recepteur nicotinique de l'acetylcholine et/ou ligands serotoninergiques

Cited By (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9540379B2 (en) 2011-01-31 2017-01-10 Boehringer Ingelheim International Gmbh (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases
CN103391941A (zh) * 2011-02-23 2013-11-13 辉瑞大药厂 用于治疗神经障碍的咪唑并[5,1-f][1,2,4]三嗪类
US8598155B2 (en) 2011-02-23 2013-12-03 Pfizer Inc. Imidazo[5,1-f][1,2,4]triazines for the treatment of neurological disorders
WO2012114222A1 (fr) * 2011-02-23 2012-08-30 Pfizer Inc. Imidazo[5,1-f][1,2,4] triazines pour traiter les troubles neurologiques
US9200000B2 (en) 2011-02-23 2015-12-01 Pfizer Inc. Imidazo[5,1-f][1,2,4]triazines for the treatment of neurological disorders
EA022586B1 (ru) * 2011-02-23 2016-01-29 Пфайзер Инк. ИМИДАЗО[5,1-f][1,2,4]ТРИАЗИНЫ ДЛЯ ЛЕЧЕНИЯ НЕВРОЛОГИЧЕСКИХ РАССТРОЙСТВ
WO2014019979A1 (fr) 2012-07-31 2014-02-06 Boehringer Ingelheim International Gmbh 4-méthyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphtalènes
US9085584B2 (en) 2012-07-31 2015-07-21 Boehringer Ingelheim International Gmbh Substituted pyrido[3,2-E][1,2,4]-triazolo[4,3-A]pyrazines for the treatment of central nervous system disorders
WO2015096651A1 (fr) 2013-12-23 2015-07-02 Merck Sharp & Dohme Corp. Composés pyrimidone carboxamide utilisés en tant qu'inhibiteurs de pde2
US9815796B2 (en) 2013-12-23 2017-11-14 Merck Sharp & Dohme Corp. Pyrimidone carboxamide compounds as PDE2 inhibitors
WO2015106032A1 (fr) 2014-01-08 2015-07-16 Intra-Cellular Therapies, Inc. Produits et compositions pharmaceutiques
US11186582B2 (en) 2014-04-23 2021-11-30 Dart Neuroscience, (Cayman) LTD. Substituted [1,2,4]triazolo[1,5-a]pyrimidin-7-yl compounds as PDE2 inhibitors
WO2015164508A1 (fr) 2014-04-23 2015-10-29 Dart Neuroscience, Llc Composés de [1,2,4]triazolo[1,5-a]pyrimidin-7-yle substitués utilisables en tant qu'inhibiteurs de pde2
US10501465B2 (en) 2014-04-23 2019-12-10 Dart Neuroscience (Cayman) Ltd. Substituted [1,2,4]triazolo[1,5-A]pyrimidin-7-yl compounds as PDE2 inhibitors
US9932345B2 (en) 2014-04-23 2018-04-03 Dart Neuroscience (Cayman) Ltd. Substituted [1,2,4]triazolo[1,5-A]pyrimidin-7-yl compounds as PDE2 inhibitors
EP3597649A1 (fr) 2014-04-23 2020-01-22 Dart NeuroScience (Cayman) Ltd Composés substitués de [1,2,4]triazolo[1,5-a]pyrimidine-7-yl utilisés en tant qu'inhibiteurs pde2
US10239882B2 (en) 2014-11-05 2019-03-26 Dart Neuroscience (Cayman) Ltd. Substituted 5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine compounds as PDE2 inhibitors
US10300064B2 (en) 2014-12-06 2019-05-28 Intra-Cellular Therapies, Inc. Organic compounds
US10543194B2 (en) 2014-12-06 2020-01-28 Intra-Cellular Therapies, Inc. Organic compounds
US10105349B2 (en) 2014-12-06 2018-10-23 Intra-Cellular Therapies, Inc. Organic compounds
WO2016149058A1 (fr) 2015-03-17 2016-09-22 Merck Sharp & Dohme Corp. Composés de triazolyl pyrimidinone en tant qu'inhibiteurs de pde2
US10358435B2 (en) 2015-03-17 2019-07-23 Merck Sharp & Dohme Corp. Triazolyl pyrimidinone compounds as PDE2 inhibitors
US10287269B2 (en) 2015-03-26 2019-05-14 Merck Sharp & Dohme Corp. Pyrazolyl pyrimidinone compounds as PDE2 inhibitors
WO2016154081A1 (fr) 2015-03-26 2016-09-29 Merck Sharp & Dohme Corp. Composés pyrazolyle pyrimidinone utilisés en tant qu'inhibiteurs de pde2
US10195201B2 (en) 2015-05-05 2019-02-05 Merck Sharp & Dohme Corp. Heteroaryl-pyrimidinone compounds as PDE2 inhibitors
US10285989B2 (en) 2015-05-15 2019-05-14 Merck Sharp & Dohme Corp. Pyrimidinone amide compounds as PDE2 inhibitors
US10160762B2 (en) 2015-05-29 2018-12-25 Merck Sharp & Dohme Corp. 6-alkyl dihydropyrazolopyrimidinone compounds as PDE2 inhibitors
US10174037B2 (en) 2015-06-04 2019-01-08 Merck Sharp & Dohme Corp. Dihydropyrazolopyrimidinone compounds as PDE2 inhibitors
WO2016209749A1 (fr) 2015-06-25 2016-12-29 Merck Sharp & Dohme Corp. Composés bicycliques pyrazolo/imidazolo substitués en tant qu'inhibiteurs de pde2
US10647727B2 (en) 2015-06-25 2020-05-12 Merck Sharp & Dohme Corp. Substituted pyrazolo/imidazolo bicyclic compounds as PDE2 inhibitors
US10357481B2 (en) 2015-07-01 2019-07-23 Merck Sharp & Dohme Corp. Substituted triazolo bicyclic compounds as PDE2 inhibitors
US10287293B2 (en) 2015-07-01 2019-05-14 Merck Sharp & Dohme Corp. Bicyclic heterocyclic compounds as PDE2 inhibitors
US10479794B2 (en) 2015-10-13 2019-11-19 Boehringer Ingelheim International Gmbh Cyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxyamide
US10023575B2 (en) 2015-10-13 2018-07-17 Boehringer Ingelheim International Gmbh Cyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxyamide
EP3156405A1 (fr) 2015-10-13 2017-04-19 Boehringer Ingelheim International GmbH Dérivés d'éther spirocycliques de pyrazolo [1,5-a] pyrimidine-3-carboxamide
US10875867B2 (en) 2015-10-13 2020-12-29 Boehringer Ingelheim International Gmbh Cyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxyamide
US11691977B2 (en) 2015-10-13 2023-07-04 Boehringer Ingelheim International Gmbh Cyclic ether derivatives of pyrazolo[1,5-A]pyrimidine-3-carboxyamide
WO2019101970A1 (fr) 2017-11-23 2019-05-31 Oslo University Hospital Hf Traitement de la tachycardie
US11419874B2 (en) 2017-11-23 2022-08-23 Oslo University Hospital Hf Treatment of tachycardia
CN112996492A (zh) * 2018-09-05 2021-06-18 阿姆斯特丹大学 Pde11或pde2抑制剂用于治疗帕金森氏疾病的用途
CN114890897A (zh) * 2022-05-31 2022-08-12 常州大学 一种pde2抑制剂内酯类衍生物及其制备方法

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