AR084516A1 - METABOTROPIC GLUTAMATE RECEIVERS MODULATORS - Google Patents

METABOTROPIC GLUTAMATE RECEIVERS MODULATORS

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Publication number
AR084516A1
AR084516A1 ARP110104855A ARP110104855A AR084516A1 AR 084516 A1 AR084516 A1 AR 084516A1 AR P110104855 A ARP110104855 A AR P110104855A AR P110104855 A ARP110104855 A AR P110104855A AR 084516 A1 AR084516 A1 AR 084516A1
Authority
AR
Argentina
Prior art keywords
amino
dihydroquinazolin
alkyl
dimethyl
methyl
Prior art date
Application number
ARP110104855A
Other languages
Spanish (es)
Inventor
Ulrich Abel
Udo Meyer
Ronalds Zemribo
Bjoern Krueger
Holger Kubas
Original Assignee
Merz Pharma Gmbh & Co Kgaa
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 Merz Pharma Gmbh & Co Kgaa filed Critical Merz Pharma Gmbh & Co Kgaa
Publication of AR084516A1 publication Critical patent/AR084516A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
    • C07D239/84—Nitrogen atoms
    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (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

La presente se relaciona además con un proceso para la preparación de dichos compuestos. Los compuestos de la presente son moduladores de mGluR5 y por ello son de utilidad para el control y la prevención de trastornos neurológicos agudos y/o crónicos.Reivindicación 1: Un compuesto caracterizado porque se selecciona entre los de la fórmula (1), donde: X representa CH2 o C=O; Y representa CR6R7, NR8, O ó S; R1 representa H, alquilo C1-6, o F; R2 representa H, alquilo C1-6, o F; o R1 y R2 junto con el átomo de carbono al cual se encuentran unidos forman un anillo de entre 3 y 7 miembros que puede ser saturado o insaturado, donde el anillo opcionalmente puede contener uno o dos heteroátomos seleccionados entre azufre, oxígeno, y nitrógeno y donde el anillo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alquilo C1-6, alcoxi C1-6, amino, hidroxi, ciano, acilo, alquil C1-6amino, di-(alquil C1-6)amino, alquil C1-6carbonilamino, y oxo; R3 representa H, alquilo C1-6, o F; R4 representa H, alquilo C1-6, o F; o R3 y R4 junto con el átomo de carbono al cual se encuentran unidos forman un anillo de entre 3 y 7 miembros que puede ser saturado o insaturado, donde el anillo opcionalmente puede contener uno o dos heteroátomos seleccionados entre azufre, oxígeno, y nitrógeno y donde el anillo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alquilo C1-6, alcoxi C1-6, amino, hidroxi, ciano, acilo, alquil C1-6amino, di-(alquil C1-6)amino, alquil C1-6carbonilamino, y oxo; R5 representa una porción monocíclica seleccionada entre arilo, heteroarilo, cicloalquilo C3-6, y heterociclilo; R6 representa H, alquilo C1-6, o F; R7 representa H, alquilo C1-6, o F; o R6 y R7 junto con el átomo de carbono al cual se encuentran unidos forman un anillo de entre 3 y 7 miembros que puede ser saturado o insaturado, donde el anillo opcionalmente puede contener uno o dos heteroátomos seleccionados entre azufre, oxígeno, y nitrógeno y donde el anillo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alquilo C1-6, alcoxi C1-6, amino, hidroxi, ciano, acilo, alquil C1-6amino, di-(alquil C1-6)amino, alquil C1-6carbonilamino, y oxo; R8 representa H, alquilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquil C1-6amino, y di-(alquil C1-6)amino, cicloalquilo C3-6, alquilcarbonilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquil C1-6amino, y di-(alquil C1-6)amino, cicloalquil C3-6carbonilo, alcoxicarbonilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquil C1-6amino, y di-(alquil C1-6)amino, aminocarbonilo, N-alquil C1-6aminocarbonilo donde la porción alquilo puede estar opcionalmente sustituida con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquil C1-6amino, y di-(alquil C1-6)amino, N,N-di-(alquil C1-6)aminocarbonilo, donde las porciones alquilo pueden estar opcionalmente sustituidas con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquil C1-6amino, y di-(alquil C1-6)amino; e isómeros ópticos, prodrogas, sales aceptables farmacéuticamente, hidratos, solvatos, y polimorfos del mismo; donde debe comprenderse que el compuesto de fórmula (1) no puede representar: 2-((2,4-diclorofenil)amino)-7-metil-7,8-dihidroquinazolin-5(6H)-ona, 2-((2,4-dimetilfenil)amino)-7-metil-7,8-dihidroquinazolin-5(6H)-ona, 2-((2-metoxifenil)amino)-7,7-dimetil-7,8-dihidroquinazolin-5(6H)-ona, 2-((2-metoxifenil)amino)-7-metil-7,8-dihidroquinazolin-5(6H)-ona, 2-((3-(trifluorometil)fenil)amino)-7,8-dihidroquinazolin-5(6H)-ona, 2-((3,4-dimetilfenil)amino)-7-metil-7,8-dihidroquinazolin-5(6H)-ona, 2-((3,5-dimetoxifenil)amino)-7,7-dimetil-7,8-dihidroquinazolin-5(6H)-ona, 2-((4-etilfenil)amino)-7,7-dimetil-7,8-dihidroquinazolin-5(6H)-ona, 2-((4-etilfenil)amino)-7-metil-7,8-dihidroquinazolin-5(6H)-ona, 2-((4-fluorofenil)amino)-7,7-dimetil-7,8-dihidroquinazolin-5(6H)-ona, 2-((4-fluorofenil)amino)-7,8-dihidroquinazolin-5(6H)-ona, 2-((4-fluorofenil)amino)-7-metil-7,8-dihidroquinazolin-5(6H)-ona, 2-((4-metoxifenil)amino)-7,7-dimetil-7,8-dihidroquinazolin-5(6H)-ona, 2-((4-metoxifenil)amino)-7,8-dihidroquinazolin-5(6H)ona, 2-((4-metoxifenil)amino)-7-metil-7,8-dihidroquinazolin-5(6H)-ona, 2-(ciclopentilamino)-7,7-dimetil-7,8-dihidroquinazolin-5(6H)-ona, 2-(ciclopropilamino)-7,7-dimetil-7,8-dihidroquinazolin.-5(6H)-ona, 2-(m-tolilamino)-7,8-dihidroquinazolin-5(6H)-ona, 2-(fenilamino)-7,8-dihidroquinazolin-5(6H)-ona, 2-(p-tolilamino)-7,8-dihidroquinazolin-5(6H)-ona, 7,7-dimetil-2-((3-(trifluorometil)fenil)amino)-7,8-dihidroquinazolin-5(6H)-ona, 7,7-dimetil-2-((4-fenoxifenil)amino)-7,8-dihidroquinazolin-5(6H)-ona, 7,7-dimetil-2-(m-tolilamino)-7,8-dihidroquinazolin-5(6H)-ona, 7,7-dimetil-2-(fenilamino)-7,8-dihidroquinazolin-5(6H)-ona, 7-metil-2-((4-fenoxifenil)amino)-7,8-dihidroquinazolin-5(6H)-ona, 7-metil-2-(p-tolilamino)-7,8-dihidroquinazolin-5(6H)-ona, 7,7-dimetil-2-(p-tolilamino)-7,8-dihidroquinazolin-5(6H)-ona, 7-metil-2-(fenilamino)-7,8-dihidroquinazolin-5(6H)-ona, 2-((3,5-dimetilfeni))amino)-7,8-dihidroquinazolin-5(6H)-ona, 7-metil-2-(m-tolilamino)-7,8-dihidroquinazolin-5(6H)-ona, o 7-metil-2-((3-(trifluorometil)fenil)amino)-7,8-dihidroquinazolin-5(6H)-ona.This also relates to a process for the preparation of said compounds. The compounds herein are mGluR5 modulators and are therefore useful for the control and prevention of acute and / or chronic neurological disorders. Claim 1: A compound characterized in that it is selected from those of the formula (1), wherein: X represents CH2 or C = O; Y represents CR6R7, NR8, O or S; R1 represents H, C1-6 alkyl, or F; R2 represents H, C1-6 alkyl, or F; or R1 and R2 together with the carbon atom to which they are attached form a ring of between 3 and 7 members that can be saturated or unsaturated, where the ring can optionally contain one or two heteroatoms selected from sulfur, oxygen, and nitrogen and where the ring may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkyl, C1-6 alkoxy, amino, hydroxy, cyano, acyl, C1-6 alkyl, di- (C1-6 alkyl ) amino, C 1-6 alkylcarbonylamino, and oxo; R3 represents H, C1-6 alkyl, or F; R4 represents H, C1-6 alkyl, or F; or R3 and R4 together with the carbon atom to which they are attached form a ring of between 3 and 7 members that can be saturated or unsaturated, where the ring can optionally contain one or two heteroatoms selected from sulfur, oxygen, and nitrogen and where the ring may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkyl, C1-6 alkoxy, amino, hydroxy, cyano, acyl, C1-6 alkyl, di- (C1-6 alkyl ) amino, C 1-6 alkylcarbonylamino, and oxo; R5 represents a monocyclic portion selected from aryl, heteroaryl, C3-6 cycloalkyl, and heterocyclyl; R6 represents H, C1-6 alkyl, or F; R7 represents H, C1-6 alkyl, or F; or R6 and R7 together with the carbon atom to which they are attached form a ring of between 3 and 7 members that can be saturated or unsaturated, where the ring can optionally contain one or two heteroatoms selected from sulfur, oxygen, and nitrogen and where the ring may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkyl, C1-6 alkoxy, amino, hydroxy, cyano, acyl, C1-6 alkyl, di- (C1-6 alkyl ) amino, C 1-6 alkylcarbonylamino, and oxo; R 8 represents H, C 1-6 alkyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C 1-6 alkoxy, amino, hydroxy, C 1-6 alkyl, and di- (C 1-6 alkyl) amino , C3-6 cycloalkyl, C1-6 alkylcarbonyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkyl, and di- (C1-6 alkyl ) amino, C 3-6 cycloalkylcarbonyl, C 1-6 alkoxycarbonyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C 1-6 alkoxy, amino, hydroxy, C 1-6 alkyl, and di- (C 1-6 alkyl) -6) amino, aminocarbonyl, N-C1-6 aminocarbonyl where the alkyl portion may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6amino alkyl, and di - (alkyl C1-6) amino, N, N-di- (C1-6 alkyl) aminocarbonyl, where the alkyl portions may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C 1-6 alkyl, and di- (C 1-6 alkyl) amino; and optical isomers, prodrugs, pharmaceutically acceptable salts, hydrates, solvates, and polymorphs thereof; where it should be understood that the compound of formula (1) cannot represent: 2 - ((2,4-dichlorophenyl) amino) -7-methyl-7,8-dihydroquinazolin-5 (6H) -one, 2 - ((2 , 4-dimethylphenyl) amino) -7-methyl-7,8-dihydroquinazolin-5 (6H) -one, 2 - ((2-methoxyphenyl) amino) -7,7-dimethyl-7,8-dihydroquinazolin-5 ( 6H) -one, 2 - ((2-methoxyphenyl) amino) -7-methyl-7,8-dihydroquinazolin-5 (6H) -one, 2 - ((3- (trifluoromethyl) phenyl) amino) -7.8 -dihydroquinazolin-5 (6H) -one, 2 - ((3,4-dimethylphenyl) amino) -7-methyl-7,8-dihydroquinazolin-5 (6H) -one, 2 - ((3,5-dimethoxyphenyl) amino) -7,7-dimethyl-7,8-dihydroquinazolin-5 (6H) -one, 2 - ((4-ethylphenyl) amino) -7,7-dimethyl-7,8-dihydroquinazolin-5 (6H) - one, 2 - ((4-ethylphenyl) amino) -7-methyl-7,8-dihydroquinazolin-5 (6H) -one, 2 - ((4-fluorophenyl) amino) -7,7-dimethyl-7,8 -dihydroquinazolin-5 (6H) -one, 2 - ((4-fluorophenyl) amino) -7,8-dihydroquinazolin-5 (6H) -one, 2 - ((4-fluorophenyl) amino) -7-methyl-7 , 8-dihydroquinazolin-5 (6H) -one, 2 - ((4-methoxyphenyl) amino) -7,7-dimethyl-7,8-dihydroquinazolin-5 (6H) -one, 2 - ((4-methoxyphenyl) amino) -7,8-dihydroquin azolin-5 (6H) one, 2 - ((4-methoxyphenyl) amino) -7-methyl-7,8-dihydroquinazolin-5 (6H) -one, 2- (cyclopentylamino) -7,7-dimethyl-7, 8-dihydroquinazolin-5 (6H) -one, 2- (cyclopropylamino) -7,7-dimethyl-7,8-dihydroquinazolin.-5 (6H) -one, 2- (m-tolylamino) -7,8-dihydroquinazolin -5 (6H) -one, 2- (phenylamino) -7,8-dihydroquinazolin-5 (6H) -one, 2- (p-tolylamino) -7,8-dihydroquinazolin-5 (6H) -one, 7, 7-dimethyl-2 - ((3- (trifluoromethyl) phenyl) amino) -7,8-dihydroquinazolin-5 (6H) -one, 7,7-dimethyl-2 - ((4-phenoxyphenyl) amino) -7, 8-dihydroquinazolin-5 (6H) -one, 7,7-dimethyl-2- (m-tolylamino) -7,8-dihydroquinazolin-5 (6H) -one, 7,7-dimethyl-2- (phenylamino) - 7,8-dihydroquinazolin-5 (6H) -one, 7-methyl-2 - ((4-phenoxyphenyl) amino) -7,8-dihydroquinazolin-5 (6H) -one, 7-methyl-2- (p- tolylamino) -7,8-dihydroquinazolin-5 (6H) -one, 7,7-dimethyl-2- (p-tolylamino) -7,8-dihydroquinazolin-5 (6H) -one, 7-methyl-2- ( phenylamino) -7,8-dihydroquinazolin-5 (6H) -one, 2 - ((3,5-dimethylpheni)) amino) -7,8-dihydroquinazolin-5 (6H) -one, 7-methyl-2- ( m-tolylamino) -7,8-dihydroquinazolin-5 (6H) -one, or 7 -methyl-2 - ((3- (trifluoromethyl) phenyl) amino) -7,8-dihydroquinazolin-5 (6H) -one.

ARP110104855A 2010-12-22 2011-12-21 METABOTROPIC GLUTAMATE RECEIVERS MODULATORS AR084516A1 (en)

Applications Claiming Priority (2)

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US201061459976P 2010-12-22 2010-12-22
EP10196573 2010-12-22

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AR084516A1 true AR084516A1 (en) 2013-05-22

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WO2014020038A1 (en) * 2012-08-03 2014-02-06 Boehringer Ingelheim International Gmbh Process for preparing spiro[2.5]octane-5,7-dione
CN104262265B (en) * 2014-07-21 2016-04-13 湖南华腾制药有限公司 A kind of preparation method of tetrahydro quinazoline derivative
JP6742316B2 (en) 2014-09-09 2020-08-19 ベーリンガー インゲルハイム インターナショナル トレイディング （シャンハイ） カンパニー リミテッド Novel process for the preparation of spiro[2.5]octane-5,7-dione and spiro[3.5]nonane-6,8-dione
WO2017189553A1 (en) * 2016-04-25 2017-11-02 Everon Biosciences, Inc. Removal of senescence-associated macrophages
US20230348401A1 (en) * 2020-01-15 2023-11-02 The Trustees Of Princeton University Inhibitors of Glucose-6-phosphate Dehydrogenase and Uses Thereof

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ES413944A1 (en) 1972-04-20 1976-06-01 Merz & Co Drugs or medicines for influencing the central nervous system
DE2856393C2 (en) 1978-12-27 1983-04-28 Merz + Co GmbH & Co, 6000 Frankfurt Medicines used to treat Parkinson's disease
ATE94384T1 (en) 1989-04-14 1993-10-15 Merz & Co Gmbh & Co USE OF ADAMANTAN DERIVATIVES FOR PREVENTION AND TREATMENT OF CEREBRAL ISCHAEMIA.
DE102004020908A1 (en) * 2004-04-28 2005-11-17 Grünenthal GmbH Substituted 5,6,7,8-tetrahydropyrido [4,3-d] pyrimidin-2-yl and 5,6,7,8-tetrahydroquinazolin-2-yl compounds
AR058554A1 (en) * 2005-12-20 2008-02-13 Novartis Ag HITEROCICLIC COMPOUNDS NITROGENATED OF 6 SUBSTITUTED MEMBERS, METHODS FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USE IN THE TREATMENT OF DISEASES MEDIATED BY MGLUR5.
WO2009015897A1 (en) * 2007-08-02 2009-02-05 Recordati Ireland Limited Novel heterocyclic compounds as mglu5 antagonists
ES2375919T3 (en) * 2008-01-11 2012-03-07 F. Hoffmann-La Roche Ag BETA-AMYLOID MODULATORS.

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