CA2908482A1 - Novel compounds as dual inhibitors of phosphodiesterases and histone deacetylases - Google Patents

Novel compounds as dual inhibitors of phosphodiesterases and histone deacetylases

Info

Publication number
CA2908482A1
CA2908482A1 CA2908482A CA2908482A CA2908482A1 CA 2908482 A1 CA2908482 A1 CA 2908482A1 CA 2908482 A CA2908482 A CA 2908482A CA 2908482 A CA2908482 A CA 2908482A CA 2908482 A1 CA2908482 A1 CA 2908482A1
Authority
CA
Canada
Prior art keywords
formula
compound
mmol
saturated
give
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.)
Abandoned
Application number
CA2908482A
Other languages
English (en)
French (fr)
Inventor
Maria Del Mar Cuadrado Tejedor
Rafael Franco Fernandez
Ana Maria Garcia Osta
Julen Oyarzabal Santamarina
Maria Obdulia Rabal Gracia
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.)
Fundacion para la Investigacion Medica Aplicada
Original Assignee
Fundacion para la Investigacion Medica Aplicada
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 Fundacion para la Investigacion Medica Aplicada filed Critical Fundacion para la Investigacion Medica Aplicada
Publication of CA2908482A1 publication Critical patent/CA2908482A1/en
Abandoned 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
    • 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
    • A61K31/495—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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07D487/12—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 three hetero rings
    • C07D487/14—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
CA2908482A 2013-03-01 2014-02-27 Novel compounds as dual inhibitors of phosphodiesterases and histone deacetylases Abandoned CA2908482A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13382065.4 2013-03-01
EP13382065 2013-03-01
PCT/EP2014/053877 WO2014131855A1 (en) 2013-03-01 2014-02-27 Novel compounds as dual inhibitors of phosphodiesterases and histone deacetylases

Publications (1)

Publication Number Publication Date
CA2908482A1 true CA2908482A1 (en) 2014-09-04

Family

ID=47901928

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2908482A Abandoned CA2908482A1 (en) 2013-03-01 2014-02-27 Novel compounds as dual inhibitors of phosphodiesterases and histone deacetylases

Country Status (7)

Country Link
US (1) US9573956B2 (https=)
EP (1) EP2961741B1 (https=)
JP (1) JP6338601B2 (https=)
CA (1) CA2908482A1 (https=)
DK (1) DK2961741T3 (https=)
ES (1) ES2635016T3 (https=)
WO (1) WO2014131855A1 (https=)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3041474B1 (en) * 2013-09-05 2020-03-18 Genentech, Inc. Antiproliferative compounds
US9840489B2 (en) * 2013-12-20 2017-12-12 Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China Piperidine carboxamide compound, preparation method, and usage thereof
CN106536509B (zh) * 2014-06-16 2020-06-09 基础应用医学研究基金会 作为组蛋白甲基转移酶和dna甲基转移酶的双重抑制剂的新型化合物
CA2992846A1 (en) 2014-08-04 2016-02-11 Fundacion Para La Investigacion Medica Aplicada Novel compounds for use in cognition improvement
WO2016120432A1 (en) * 2015-01-30 2016-08-04 Fundación Para La Investigación Médica Aplicada Compounds and methods for anticoagulation therapy
CN104610166B (zh) * 2015-03-10 2017-06-13 山东大学 嘧啶苄基异羟肟酸类组蛋白去乙酰化酶抑制剂及制备方法和应用
US9745253B2 (en) 2015-03-13 2017-08-29 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
AU2015399642B2 (en) 2015-06-26 2020-04-09 Chongqing Dikang Erle Pharma Co. Ltd. Novel phosphodiesterase type-5 inhibitor and application thereof
KR102590848B1 (ko) 2016-12-28 2023-10-19 다트 뉴로사이언스, 엘엘씨 Pde2 억제제로서 치환된 피라졸로피리미디논 화합물
CN107163052B (zh) * 2017-04-18 2020-08-11 华南农业大学 一种针对多种pde-5抑制剂药物的免疫检测方法
US11548867B2 (en) 2017-07-19 2023-01-10 Idea Ya Biosciences, Inc. Amido compounds as AhR modulators
CN108912029B (zh) * 2017-08-25 2021-10-01 广东东阳光药业有限公司 含氮杂环酰胺衍生物及其用途
DK3717488T3 (da) 2017-11-27 2021-12-13 Dart Neuroscience Llc Substituerede furanopyrimidinforbindelser som pde1-inhibitorer
CN110054625B (zh) * 2018-01-18 2022-01-07 山东大学 N-酰基苯磺酰胺异羟肟酸类Bcl-2、HDAC双靶点抑制剂及制备方法和应用
CN108558890A (zh) * 2018-06-28 2018-09-21 重庆康刻尔制药有限公司 一种西地那非中间体合成方法
CN109824516B (zh) * 2019-03-14 2021-07-23 泰州精英化成医药科技有限公司 一种反式-4-羟基环已烷甲酸叔丁酯的制备方法
CN109810108B (zh) * 2019-03-20 2021-08-06 华东理工大学 2,8-二氮杂-螺-[4,5]-癸烷类嘧啶-异羟肟酸化合物及其用途
WO2022123310A1 (en) 2020-12-11 2022-06-16 Ildong Pharmaceutical Co., Ltd. Novel compounds as androgen receptor and phosphodiesterase dual inhibitor
AU2022420827A1 (en) 2021-12-22 2024-06-13 Augustine Therapeutics Compounds and use thereof as hdac6 inhibitors
CN115417877B (zh) * 2022-09-20 2024-05-14 杭州师范大学 组蛋白去乙酰化酶抑制剂及其制备和在制备抗癌症药物上的应用
CN116375714A (zh) * 2023-03-24 2023-07-04 苏州满元生物科技有限公司 卡巴地那非类药物关键中间体的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1469852A4 (en) * 2002-01-04 2009-12-02 Ford Henry Health System NITROGEN DONORS FOR THE TREATMENT OF DISEASE AND INJURY
CN1548438A (zh) * 2003-05-16 2004-11-24 烟台开发区北方药物研究所 2-取代苯基-6,8-二烃基-3H-咪唑[1,5α][1,3,5]三嗪-4-酮衍生物,其制备方法及其药物用途
US7666872B2 (en) * 2004-03-05 2010-02-23 Nycomed Gmbh Use for PDE5 inhibitors
ES2548759T3 (es) * 2006-08-24 2015-10-20 Surface Logix, Inc. Compuestos farmacocinéticamente mejorados
WO2008033747A2 (en) * 2006-09-11 2008-03-20 Curis, Inc. Multi-functional small molecules as anti-proliferative agents
CN101754756A (zh) * 2007-05-18 2010-06-23 维瓦斯公司 包含磷酸二酯酶-5抑制剂的新组合和它们的用途
EP2603511B1 (en) * 2010-08-12 2017-03-15 Boehringer Ingelheim International GmbH 6-cycloalkyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors
EP2535049A1 (en) 2011-06-17 2012-12-19 Proyecto de Biomedicina Cima, S.L. Tadalafil for the treatment of dementia

Also Published As

Publication number Publication date
DK2961741T3 (en) 2017-07-03
WO2014131855A1 (en) 2014-09-04
US20160002246A1 (en) 2016-01-07
WO2014131855A9 (en) 2014-11-13
ES2635016T3 (es) 2017-10-02
JP2016513130A (ja) 2016-05-12
EP2961741A1 (en) 2016-01-06
JP6338601B2 (ja) 2018-06-06
US9573956B2 (en) 2017-02-21
EP2961741B1 (en) 2017-04-05

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Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20190221

FZDE Discontinued

Effective date: 20210831