AR061369A1 - PIRIMIDINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THAT UNDERSTAND THEM - Google Patents

PIRIMIDINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THAT UNDERSTAND THEM

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Publication number
AR061369A1
AR061369A1 ARP070102594A ARP070102594A AR061369A1 AR 061369 A1 AR061369 A1 AR 061369A1 AR P070102594 A ARP070102594 A AR P070102594A AR P070102594 A ARP070102594 A AR P070102594A AR 061369 A1 AR061369 A1 AR 061369A1
Authority
AR
Argentina
Prior art keywords
alkyl
heterocyclyl
alkynyl
alkenyl
independently selected
Prior art date
Application number
ARP070102594A
Other languages
Spanish (es)
Original Assignee
Astex Therapeutics Ltd
Astrazeneca Ab
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.)
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38831992&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR061369(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Astex Therapeutics Ltd, Astrazeneca Ab filed Critical Astex Therapeutics Ltd
Publication of AR061369A1 publication Critical patent/AR061369A1/en

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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
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurosurgery (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Estos compuestos proporcionan un tratamiento o profilaxis para el deterioro cognitivo, la enfermedad de Alzheimer, la neurodegeneracion y la demencia. Reivindicacion 1: Un compuesto de formula 1: donde A se selecciona independientemente entre un anillo heterocíclico de 5, 6 o 7 miembros opcionalmente sustituido con uno o más R1; B se selecciona independientemente entre fenilo o entre un anillo heteroaromático de 5 o 6 miembros opcionalmente sustituido con uno o más R2, C se selecciona independientemente entre fenilo o un anillo heteroaromático de 5 o 6 miembros opcionalmente sustituido con uno o más R3; R1 se selecciona independientemente entre halogeno, ciano, nitro, OR6, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilC0- 6arilo, alquilC0-6heteroarilo, alquilC0-6-cicloalquilo C3-6, alquil C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6, alquil C0-6-heterociclilo C3-6, NR6R7, CONR6R7, NR6(CO)R7, O(CO)R6, CO2R6, COR6, (SO2)NR6R7, NR6(SO2)R7, SOR6, SO2R6, OSO2R6 y SO3R6 donde dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquil C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6 y alquil C0-6 heterociclilo C3-6 está opcionalmente sustituido con uno o más E; o dos sustituyentes R1 junto con el átomo al cual están unidos, forman un anillo cíclico o heterocíclico opcionalmente sustituido con uno o más E; R2, R3 o R4 se selecciona entre arilo, heteroarilo, cicloalquenilo C3-6, cicloalquinilo C3-6, heterociclilo C3-6, CONR6R7, NR6(CO)R7, O(CO)R6, CO2R6, COR6, (SO2)NR6R7, NR6(SO2)R7, SOR6, SO2R6, OSO2R6 y SO3R6 donde dicho arilo, heteroarilo, cicloalquenilo C3-6, cicloalquinilo C3-6 y heterociclilo C3-6 puede estar opcionalmente sustituido con uno o más E; R5se selecciona independientemente entre hidrogeno, ciano, OR6, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquil C0-6- cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6, alquiI C0-6heterociclilo C3-6, CONR6R7, CO2R6, COR6, SO2R6 y SO3R6 donde dicho alquiIo C1-6, alquenilo C2-6, aIquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquiI C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6, alquil C0-6-heterociclilo C3-6 puede estar opcionalmente sustituido con uno o más E; E se selecciona independientemente entre halogeno, nitro, CN, OR6, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquil C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6, alquil C0-6-heterociclilo, fluormetilo, difluormetilo, trifluormetilo, fluorrnetoxi, difluormetoxi, trifluormetoxi, NR6R7, CONR6R7, NR6(CO)R7, O(CO)R6, CO2R6, COR6, (SO2)NR6R7, NR6SO2R7, SO2R6, SOR6, OSO2R6 y SO3R6, donde dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6- cicloalquilo C3-6, alquil C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6 o alquilC0-6heterociclilo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados independientemente entre halo, nitro, ciano, OR6, alquiIo C1- 6, fluormetilo, difluormetilo, trifluormetilo, fluormetoxi, difluormetoxi y trifluormetoxi; R6 y R7 se seleccionan independientemente entre hidrogeno, alquilo C1-6, fluormetilo, difluormetilo, trifluormetilo, alquenilo C2-6, alquinilo C2-6, alquilC0- 6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquil C0-6cicloalquenilo C3-6, aIquil C0-6-cicloalquinilo C3-6, alquilC0-6heterociclilo, o R6 y R7 pueden formar en forma conjunta un anillo heterocíclico de 5 o 6 miembros que contiene uno o más heteroátomos seleccionados entre N, O o S; R8 se selecciona independientemente entre halogeno, ciano, nitro, OR9, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquil C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6, alquil C0-6-heterociclilo C3-6, NR9R10, CONR9R10, NR9(CO)R10, O(CO)R9, CO2R9, COR9, (SO2)NR9R10, NR9(SO2)R10, SO2R9, SOR9, OSO2R9 y SO3R9 donde dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquil C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6 y alquil C0-6-heterociclilo C3-6 pueden estar opcionalmente sustituidos con uno o más E; o dos R8 pueden junto con los átomos a los cuales están unidos formar un anillo cíclico o heterocíclico opcionalmente sustituido con uno o más E; R9 y R10 se seleccionan independientemente entre hidrogeno, alquilo C1-6, fluormetilo, difluormetilo, trifluormetilo, alquenilo C2-6, alquinilo C2-6, alquilC0-6arilo, alquilC0-6heteroarilo, alquil C0-6-cicloalquilo C3-6, alquil C0-6-cicloalquenilo C3-6, alquil C0-6-cicloalquinilo C3-6, alquilC0-6heterociclilo; o R9 y R10 pueden formar en forma conjunta un anillo heterocíclico de 5 o 6 miembros que contiene uno o más heteroátomos seleccionados entre N, O o S; m= 0,1 o 2; n= 0,1, 2 o 3 p= 0,1, 2 o 3; q= 0,1, 2 o 3; t= 0, 1, 2 o 3; donde uno de n, p o q es por lo menos 1; como una base libre o una sal, solvato o solvato de una sal del mismo aceptable para uso farmacéutico.These compounds provide a treatment or prophylaxis for cognitive impairment, Alzheimer's disease, neurodegeneration and dementia. Claim 1: A compound of formula 1: wherein A is independently selected from a 5-, 6- or 7-membered heterocyclic ring optionally substituted with one or more R1; B is independently selected from phenyl or from a 5- or 6-membered heteroaromatic ring optionally substituted with one or more R2, C is independently selected from phenyl or a 5 or 6-membered heteroaromatic ring optionally substituted with one or more R3; R1 is independently selected from halogen, cyano, nitro, OR6, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6alkyl, C0-6 alkyl heteroaryl, C0-6 alkylC3-6 alkyl, C0-6 alkyl C3-6 cycloalkenyl, C0-6 alkyl C3-6 cycloalkynyl, C0-6 alkyl heterocyclyl C3-6, NR6R7, CONR6R7, NR6 (CO) R7, O (CO) R6, CO2R6, COR6, (SO2) NR6R7, NR6 (SO2) R7, SOR6, SO2R6, OSO2R6 and SO3R6 wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6alkyl, C0-6heteroaryl, C0-6-C3-6 alkyl, C0 alkyl -6-C3-6 cycloalkenyl, C0-6 alkyl C3-6 alkyl and C0-6 alkyl C3-6 heterocyclyl optionally is substituted with one or more E; or two R1 substituents together with the atom to which they are attached, form a cyclic or heterocyclic ring optionally substituted with one or more E; R2, R3 or R4 is selected from aryl, heteroaryl, C3-6 cycloalkenyl, C3-6 cycloalkynyl, C3-6 heterocyclyl, CONR6R7, NR6 (CO) R7, O (CO) R6, CO2R6, COR6, (SO2) NR6R7, NR6 (SO2) R7, SOR6, SO2R6, OSO2R6 and SO3R6 wherein said aryl, heteroaryl, C3-6 cycloalkenyl, C3-6 cycloalkynyl and C3-6 heterocyclyl may be optionally substituted with one or more E; R5 is independently selected from hydrogen, cyano, OR6, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6 alkyl, C0-6heteroaryl, C0-6 alkylC3-6 alkyl, C0-6-cycloalkenyl alkyl -6, C0-6 alkyl C3-6 alkyl, C0-6 alkyl C3-6 heterocyclyl, CONR6R7, CO2R6, COR6, SO2R6 and SO3R6 wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6 alkyl , C0-6 alkyl heteroaryl, C0-6 alkyl C3-6 alkyl, C0-6 alkyl C3-6 alkyl, C0-6 alkyl C3-6 cycloalkynyl, C0-6 alkyl C3-6 heterocyclyl may be optionally substituted with one or more E; E is independently selected from halogen, nitro, CN, OR6, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6 alkyl, C0-6 alkyl heteroaryl, C0-6 alkylC3-6 alkyl, C0-6 alkyl C3-6cycloalkenyl, C0-6 alkyl C3-6 alkyl, C0-6 alkyl heterocyclyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluorrnethoxy, difluoromethoxy, trifluoromethoxy, NR6R7, CONR6R7, NR6 (CO) R7, O (CO) R7, O (CO) R7, O (CO) R7, O (CO) R7 , CO2R6, COR6, (SO2) NR6R7, NR6SO2R7, SO2R6, SOR6, OSO2R6 and SO3R6, wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6aryl, C0-6henylaryl, C0-6- alkyl C3-6 cycloalkyl, C0-6 alkyl C3-6 cycloalkenyl, C0-6 alkyl C3-6 cycloalkynyl or C0-6 alkyl heterocyclyl may be optionally substituted with one or more substituents independently selected from halo, nitro, cyano, OR6, C1 alkyl - 6, fluormethyl, difluoromethyl, trifluoromethyl, fluoromethoxy, difluoromethoxy and trifluoromethoxy; R6 and R7 are independently selected from hydrogen, C1-6 alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, C2-6 alkenyl, C2-6 alkynyl, C0-6aryl alkyl, C0-6heteroaryl alkyl, C0-6 alkylC3-6 alkyl, C0 alkyl -6 C3-6cycloalkenyl, C0-6 alkyl-C3-6 cycloalkynyl, C0-6 alkyl heterocyclyl, or R6 and R7 can together form a 5 or 6 membered heterocyclic ring containing one or more heteroatoms selected from N, O or S ; R8 is independently selected from halogen, cyano, nitro, OR9, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6 alkyl, C0-6 alkyl heteroaryl, C0-6 alkylC3-6 alkyl, C0-6 alkyl C3-6cycloalkenyl, C0-6 alkyl C3-6 alkyl, C0-6 alkyl heterocyclyl C3-6, NR9R10, CONR9R10, NR9 (CO) R10, O (CO) R9, CO2R9, COR9, (SO2) NR9R10 , NR9 (SO2) R10, SO2R9, SOR9, OSO2R9 and SO3R9 wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C0-6alkyl, C0-6heteroaryl, C0-6-C3-6 alkyl alkyl, alkyl C0-6-C3-6 cycloalkenyl, C0-6 alkyl C3-6 alkyl and C0-6 alkyl C3-6 heterocyclyl may be optionally substituted with one or more E; or two R8 may together with the atoms to which they are attached form a cyclic or heterocyclic ring optionally substituted with one or more E; R9 and R10 are independently selected from hydrogen, C1-6 alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, C2-6 alkenyl, C2-6 alkynyl, C0-6 alkyl, C0-6 alkyl, C0-6 alkyl, C0-6 alkyl, C0 alkyl -6-C3-6 cycloalkenyl, C0-6 alkyl-C3-6 cycloalkynyl, C0-6 alkyl heterocyclyl; or R9 and R10 may together form a 5- or 6-membered heterocyclic ring containing one or more heteroatoms selected from N, O or S; m = 0.1 or 2; n = 0.1, 2 or 3 p = 0.1, 2 or 3; q = 0.1, 2 or 3; t = 0, 1, 2 or 3; where one of n, p or q is at least 1; as a free base or a salt, solvate or solvate of a salt thereof acceptable for pharmaceutical use.

ARP070102594A 2006-06-14 2007-06-13 PIRIMIDINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THAT UNDERSTAND THEM AR061369A1 (en)

Applications Claiming Priority (2)

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US81372806P 2006-06-14 2006-06-14
US89699407P 2007-03-26 2007-03-26

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AR061369A1 true AR061369A1 (en) 2008-08-20

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ID=38831992

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Country Status (7)

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EP (1) EP2035423A1 (en)
JP (1) JP2009539973A (en)
AR (1) AR061369A1 (en)
CL (1) CL2007001733A1 (en)
TW (1) TW200815443A (en)
UY (1) UY30407A1 (en)
WO (1) WO2007145568A1 (en)

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RU2008100165A (en) 2005-06-14 2009-07-20 Шеринг Корпорейшн (US) Aspartic Protease Inhibitors
MX2007016183A (en) 2005-06-14 2008-03-10 Schering Corp The preparation and use of compounds as protease inhibitors.
TW200815349A (en) 2006-06-22 2008-04-01 Astrazeneca Ab New compounds
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JP2011518224A (en) 2008-04-22 2011-06-23 シェーリング コーポレイション Thiophenyl substituted 2-imino-3-methylpyrrolopyrimidinone compounds, compositions, and their use as BACE-1 inhibitors
TW201020244A (en) 2008-11-14 2010-06-01 Astrazeneca Ab New compounds
EP2485590B1 (en) 2009-10-08 2015-01-07 Merck Sharp & Dohme Corp. Pentafluorosulfur imino heterocyclic compounds as bace-1 inhibitors, compositions, and their use
WO2011044187A1 (en) 2009-10-08 2011-04-14 Schering Corporation Iminothiadiazine dioxide compounds as bace inhibitors, compositions, and their use
UA108363C2 (en) 2009-10-08 2015-04-27 IMINOTIADIASIADIOXIDE OXIDES AS BACE INHIBITORS, COMPOSITIONS THEREOF AND THEIR APPLICATIONS
EP2485920B1 (en) 2009-10-08 2016-04-27 Merck Sharp & Dohme Corp. Pentafluorosulfur imino heterocyclic compounds as bace-1 inhibitors, compositions, and their use
CA2824360C (en) * 2011-03-01 2020-01-14 Janssen Pharmaceutica Nv 6,7-dihydro-pyrazolo[1,5-a]pyrazin-4-ylamine derivatives useful as inhibitors of beta-secretase (bace)
US9145426B2 (en) 2011-04-07 2015-09-29 Merck Sharp & Dohme Corp. Pyrrolidine-fused thiadiazine dioxide compounds as BACE inhibitors, compositions, and their use
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EP2035423A1 (en) 2009-03-18
WO2007145568A9 (en) 2008-12-11
UY30407A1 (en) 2008-01-31
CL2007001733A1 (en) 2008-01-25
WO2007145568A1 (en) 2007-12-21
TW200815443A (en) 2008-04-01
JP2009539973A (en) 2009-11-19

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