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WO2018041771A1 - Thiéno-uraciles substitués par un groupe (1-méthylcyclopropyl)méthyle et leur utilisation - Google Patents

Thiéno-uraciles substitués par un groupe (1-méthylcyclopropyl)méthyle et leur utilisation Download PDF

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Publication number
WO2018041771A1
WO2018041771A1 PCT/EP2017/071531 EP2017071531W WO2018041771A1 WO 2018041771 A1 WO2018041771 A1 WO 2018041771A1 EP 2017071531 W EP2017071531 W EP 2017071531W WO 2018041771 A1 WO2018041771 A1 WO 2018041771A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
methylcyclopropyl
pyrimidine
thieno
dione
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.)
Ceased
Application number
PCT/EP2017/071531
Other languages
German (de)
English (en)
Inventor
Michael Härter
Yolanda Cancho-Grande
Martina Delbeck
Bernd Kalthof
Klemens Lustig
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.)
Bayer Pharma AG
Original Assignee
Bayer Pharma AG
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 Bayer Pharma AG filed Critical Bayer Pharma AG
Publication of WO2018041771A1 publication Critical patent/WO2018041771A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • reaction is carried out in an alcohol as a solvent, preferably in isopropanol, at elevated temperature, preferably at about + 50 ° C.
  • cleavage of the trimethylsilyl group takes place under these conditions.
  • Ring closure to the target compounds of formula (1-5) is achieved by acid-mediated reaction with trimethyl orthoformate.
  • the compounds of formula (20) are treated in the presence of hydrogen chloride with an excess of trimethyl orthoformate in methanol. This reaction is preferably carried out at room temperature.
  • the reaction is preferably carried out in tetrahydrofuran (THF) or dichloromethane as solvent in a temperature range between 0 ° C and RT.
  • THF tetrahydrofuran
  • dichloromethane dichloromethane
  • prevention means the avoidance or reduction of the risk, a disease, a disease, a disease, an injury or a health disorder, a development or a Progression of such conditions and / or to get, experience, suffer or have the symptoms of such conditions.
  • the treatment or the prevention of a disease, a disease, a disease, an injury or a health disorder can be partial or complete.
  • the compounds according to the invention are administered in combination with a corticosteroid, such as by way of example and preferably prednisone, prednisolone, methylprednisolone, triamcinolone, dexamethasone, beclomethasone, betamethasone, flunisolide, budesonide or fluticasone.
  • a corticosteroid such as by way of example and preferably prednisone, prednisolone, methylprednisolone, triamcinolone, dexamethasone, beclomethasone, betamethasone, flunisolide, budesonide or fluticasone.
  • the compounds according to the invention are administered in combination with a thrombin inhibitor, such as, by way of example and by way of preference, ximelagatran, melagatran, dabigatran, bivalirudin or Clexane.
  • a thrombin inhibitor such as, by way of example and by way of preference, ximelagatran, melagatran, dabigatran, bivalirudin or Clexane.
  • the compounds according to the invention can act systemically and / or locally.
  • they may be applied in a suitable manner, e.g. oral, parenteral, pulmonary, nasal, sublingual, lingual, buccal, rectal, dermal, transdermal, conjunctival, otic or as an implant or stent.
  • the compounds according to the invention can be administered in suitable administration forms.
  • the animals are anaesthetized again [1.5% isoflurane (mouse), 2% isoflurane (rat) / N20 / air], and a pressure catheter is introduced into the left ventricle via the carotid artery.
  • a pressure catheter is introduced into the left ventricle via the carotid artery.
  • There are heart rate, left ventricular pressure (LVP), left ventricular end-diastolic pressure (LVEDP), contractility (dp / dt) and relaxation rate (tau) was recorded and evaluated.
  • a blood sample is used to determine the substance-plasma removed mirror and plasma biopark and killed the animals.
  • Heart ventricles, left ventricle plus septum, right ventricle), liver, lung and kidney are removed and weighed.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux dérivés de thiéno[2,3-d]pyrimidin-2,4-dione ("thiéno-uracile") portant un substituant (1-méthylcyclopropyl)méthyle en position N3, des procédés de production desdits dérivés, leur utilisation seuls ou en associations pour le traitement et/ou la prévention de maladies, ainsi que leur utilisation pour la fabrication de médicaments destinés au traitement et/ou à la prévention de maladies, en particulier au traitement et/ou à la prévention de maladies des poumons et du système cardiovasculaire, ainsi que de cancers.
PCT/EP2017/071531 2016-09-02 2017-08-28 Thiéno-uraciles substitués par un groupe (1-méthylcyclopropyl)méthyle et leur utilisation Ceased WO2018041771A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP16187023 2016-09-02
EP16187023.3 2016-09-02

Publications (1)

Publication Number Publication Date
WO2018041771A1 true WO2018041771A1 (fr) 2018-03-08

Family

ID=56853526

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2017/071531 Ceased WO2018041771A1 (fr) 2016-09-02 2017-08-28 Thiéno-uraciles substitués par un groupe (1-méthylcyclopropyl)méthyle et leur utilisation

Country Status (1)

Country Link
WO (1) WO2018041771A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020083957A1 (fr) 2018-10-24 2020-04-30 Leadxpro Ag Aminotriazines fonctionnalisées
CN113816970A (zh) * 2021-09-18 2021-12-21 济宁医学院附属医院 一种选择性铜离子螯合剂、其制备方法及其在肺纤维化中的应用

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WO2012004258A1 (fr) 2010-07-09 2012-01-12 Bayer Pharma Aktiengesellschaft Pyrimidines et triazines annelées et leur utilisation pour traiter ou prévenir des affections du système cardio-vasculaire
WO2012028647A1 (fr) 2010-09-03 2012-03-08 Bayer Pharma Aktiengesellschaft Azahétérocycles bicycliques et leur utilisation
WO2012059549A1 (fr) 2010-11-04 2012-05-10 Bayer Pharma Aktiengesellschaft 6-fluoro-1h-pyrazolo[4,3-b]pyridines substituées et leur utilisation
WO2013071169A1 (fr) 2011-11-11 2013-05-16 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2014182950A1 (fr) 2013-05-10 2014-11-13 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2014182943A1 (fr) 2013-05-10 2014-11-13 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2015052065A1 (fr) 2013-10-07 2015-04-16 Bayer Pharma Aktiengesellschaft Thiénouracile-carboxamides cycliques et utilisation associée
WO2016023832A1 (fr) 2014-08-11 2016-02-18 Hydra Biosciences, Inc. Dérivés de thiéno- et furo[2,3-d]pyrimidine-2,4(1h,3h)-dione à titre de modulateurs des trpc5 pour le traitement des troubles neuropsychiatriques
WO2016150901A1 (fr) 2015-03-26 2016-09-29 Bayer Pharma Aktiengesellschaft Hétérocyclylméthyle-thiénouraciles utilisés comme antagonistes du récepteur a2b de l'adénosine

Patent Citations (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6140325A (en) 1993-08-19 2000-10-31 Takeda Chemical Industries, Ltd. Thienopyrimidine derivatives, their production and use
WO2000061583A1 (fr) 1995-06-07 2000-10-19 Cell Therapeutics, Inc. Derives de xanthine et analogues comme inhibiteurs de transmission des signaux intracellulaires et extracellulaires
US6077814A (en) 1997-02-26 2000-06-20 Hokko Chemical Industry Co., Ltd. 1-Substituted 4-carbamoyl-1,2,4-triazol-5-one derivatives and herbicide
WO1998054190A1 (fr) 1997-05-28 1998-12-03 Astra Pharmaceuticals Ltd. Nouveaux composes
WO2000006568A1 (fr) 1998-07-29 2000-02-10 Bayer Aktiengesellschaft Derives de pyrazole substitues
WO2000006569A1 (fr) 1998-07-29 2000-02-10 Bayer Aktiengesellschaft Derives de pyrazole substitues, condenses avec des noyaux heterocycliques a six chaines
WO2000012514A1 (fr) 1998-08-28 2000-03-09 Astrazeneca Ab Nouveaux composes
WO2001019780A2 (fr) 1999-09-13 2001-03-22 Bayer Aktiengesellschaft Nouveaux derives d'acide aminodicarboxylique presentant des proprietes pharmaceutiques
WO2001019776A2 (fr) 1999-09-13 2001-03-22 Bayer Aktiengesellschaft Nouveaux derives d'acide dicarboxylique presentant des proprietes pharmaceutiques
WO2001019778A1 (fr) 1999-09-13 2001-03-22 Bayer Aktiengesellschaft Derives d'acide dicarboxylique a proprietes pharmaceutiques
WO2001019355A2 (fr) 1999-09-13 2001-03-22 Bayer Aktiengesellschaft Derives d'acide dicarboxylique presentant de nouvelles proprietes pharmaceutiques
GB2363377A (en) 2000-06-14 2001-12-19 Astrazeneca Ab Novel thieno[2,3-d]pyrimidinediones
WO2002042301A1 (fr) 2000-11-22 2002-05-30 Bayer Aktiengesellschaft Nouveaux derives de pyrazolopyridine a substitution pyridine
WO2002064598A1 (fr) 2001-02-14 2002-08-22 Warner-Lambert Company Llc Derives de thieno'2,3-d pyrimidinone utilises comme inhibiteurs de metalloproteinases matricielles
WO2002070462A1 (fr) 2001-03-07 2002-09-12 Bayer Aktiengesellschaft Derives d'acide aminodicarboxylique
WO2002070510A2 (fr) 2001-03-07 2002-09-12 Bayer Aktiengesellschaft Nouveaux derives d'acide aminodicarbonique presentant des proprietes pharmaceutiques
WO2003095451A1 (fr) 2002-05-08 2003-11-20 Bayer Healthcare Ag Pyrazolopyridines a substitution carbamate
WO2004014916A1 (fr) 2002-08-13 2004-02-19 Warner-Lambert Company Llc Inhibiteurs bicycliques condenses de metalloproteinases de type pyrimidine
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WO2012004258A1 (fr) 2010-07-09 2012-01-12 Bayer Pharma Aktiengesellschaft Pyrimidines et triazines annelées et leur utilisation pour traiter ou prévenir des affections du système cardio-vasculaire
WO2012028647A1 (fr) 2010-09-03 2012-03-08 Bayer Pharma Aktiengesellschaft Azahétérocycles bicycliques et leur utilisation
WO2012059549A1 (fr) 2010-11-04 2012-05-10 Bayer Pharma Aktiengesellschaft 6-fluoro-1h-pyrazolo[4,3-b]pyridines substituées et leur utilisation
WO2013071169A1 (fr) 2011-11-11 2013-05-16 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2014182950A1 (fr) 2013-05-10 2014-11-13 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2014182943A1 (fr) 2013-05-10 2014-11-13 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2015052065A1 (fr) 2013-10-07 2015-04-16 Bayer Pharma Aktiengesellschaft Thiénouracile-carboxamides cycliques et utilisation associée
WO2016023832A1 (fr) 2014-08-11 2016-02-18 Hydra Biosciences, Inc. Dérivés de thiéno- et furo[2,3-d]pyrimidine-2,4(1h,3h)-dione à titre de modulateurs des trpc5 pour le traitement des troubles neuropsychiatriques
WO2016150901A1 (fr) 2015-03-26 2016-09-29 Bayer Pharma Aktiengesellschaft Hétérocyclylméthyle-thiénouraciles utilisés comme antagonistes du récepteur a2b de l'adénosine

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020083957A1 (fr) 2018-10-24 2020-04-30 Leadxpro Ag Aminotriazines fonctionnalisées
US12391670B2 (en) 2018-10-24 2025-08-19 Leadxpro Ag Functionalized aminotriazines
CN113816970A (zh) * 2021-09-18 2021-12-21 济宁医学院附属医院 一种选择性铜离子螯合剂、其制备方法及其在肺纤维化中的应用

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