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AR041136A1 - Pirazolopirimidinas como inhibidores de cinasas dependientes de clclinas - Google Patents

Pirazolopirimidinas como inhibidores de cinasas dependientes de clclinas

Info

Publication number
AR041136A1
AR041136A1 ARP030103191A ARP030103191A AR041136A1 AR 041136 A1 AR041136 A1 AR 041136A1 AR P030103191 A ARP030103191 A AR P030103191A AR P030103191 A ARP030103191 A AR P030103191A AR 041136 A1 AR041136 A1 AR 041136A1
Authority
AR
Argentina
Prior art keywords
alkyl
nr5r10
cycloalkyl
aryl
group
Prior art date
Application number
ARP030103191A
Other languages
English (en)
Original Assignee
Pharmacopeia Drug Discovery
Schering Corp
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 Pharmacopeia Drug Discovery, Schering Corp filed Critical Pharmacopeia Drug Discovery
Publication of AR041136A1 publication Critical patent/AR041136A1/es

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    • 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
    • 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
    • A61K31/52—Purines, e.g. adenine
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Oncology (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

La presente proporciona compuestos de pirazolo[1,5-a]pirimidina como inhibidores de cinasas dependientes de ciclina, métodos de preparación de dichos compuestos, composiciones farmacéuticas que contienen uno o más de dichos compuestos, métodos de preparación de formulaciones farmacéuticas que comprenden uno o más de dichos compuestos, y métodos de tratamiento, prevención, inhibición, o mejoría de una o más enfermedades asociadas con las CDK, utilizando dichos compuestos o composiciones farmacéuticas. Reivindicación 1: Un compuesto representado por la fórmula estructural (1), en donde: Q es -S(O2)-, -C(O)- ; R es arilo o heteroarilo, en donde dichos arilo o heteroarilo pueden estar insustituidos, o en forma opcional, sustituidos independientemente con una o más porciones iguales o diferentes, en donde cada porción se selecciona de manera independiente entre el grupo que consiste en halógeno, CN, -OR5, -SR5, -S(O2)R6, -S(O2)NR5R6, -NR5R6, -C(O)NR5R6, CF3, alquilo, arilo y OCF3; R2 se selecciona entre el grupo que comprende CN, NR5R6, -C(O2)R6, -C(O)NR5R6, -OR6, -SR6, -S(O2)R7, -S(O2)NR5R6, -N(R5)S(O2)R7, -N(R5)C(O)R7 y -N(R5)C(O)NR5R6; alquinilo, heteroarilo, CF3, heterociclilo, alquinilalquilo, cicloalquilo, alquilo sustituido con 1 a 6 grupos R9 iguales o diferentes, se seleccionados de manera independiente entre la lista de R9 que se expone a continuación, o es un resto del grupo de fórmula (2); R3 se selecciona entre el grupo que comprende H, halógeno, -NR5R6, -C(O)NR5R6, alquilo, alquinilo, cicloalquilo, arilo, arilalquilo, heterociclilo, heterociclilalquilo, heteroarilo y heteroarilalquilo, o es un resto del grupo de fórmula (3), en donde cada uno de dichos alquilo, cicloalquilo, arilo, arilalquilo, heterociclilo, heterociclilalquilo, heteroarilo y heteroarilalquilo para R3 y las porciones heterociclilo cuyas estructuras se mostraron precedentemente para R3 pueden estar sustituidos o en forma opcional, independientemente sustituidos con una o más porciones iguales o diferentes, en donde cada porción se selecciona en forma independiente entre el grupo que consiste en halógeno, alquilo, arilo, cicloalquilo, CF3, CN, -OCF3,-(CR4R5)nOR5, -OR5, -NR5R6, -(CR4R5)nNR5R6, -C(O2)R5, -C(O)R5, -C(O)NR5R6, -SR6, -S(O2)R6, -S(O2)NR5R6, -N(R5)S(O2)R7, -N(R5)C(O)R7 y -N(R5)C(O)NR5R6; R4 es H, halo o alquilo; R5 es H o alquilo; R6 se selecciona en forma independiente entre el grupo que comprende H, alquilo, arilo, arilalquilo, cicloalquilo, heterociclilo, heterociclilalquilo, heteroarilo y heteroarilalquilo, en donde cada uno de dichos alquilo, arilo, arilalquilo, cicloalquilo, heterociclilo, heterociclilalquilo, heteroarilo, y heteroarilalquilo pueden estar insustituidos u opcionalmente sustituidos con uno o más porciones iguales o diferentes, en donde cada porción se selecciona en forma independiente entre el grupo que comprende halógeno, alquilo, arilo, cicloalquilo, heterociclilalquilo, CF3, OCF3, CN, -OR5, -NR5R10, -N(R5)Boc, -(CR4R5)nOR5, -C(O2)R5, -C(O)R5, -C(O)NR5R10, -SO3H, -SR10, -S(O2)R7, -S(O2)NR5R10, -N(R5)S(O2)R7, -N(R5)C(O)R7 y -N(R5)C(O)NR5R10; R10 se selecciona entre el grupo que consiste en H, alquilo, arilo, arilalquilo, cicloalquilo, heterociclilo, heterociclilalquilo, heteroarilo, y heteroarilalquilo, en donde cada uno de dichos alquilo, arilo, arilalquilo, cicloalquilo, heterociclilo, heterociclilalquilo, heteroarilo, y heteroarilalquilo pueden estar insustituidos u opcionalmente sustituidos con una o más porciones iguales o diferentes, en donde cada porción se selecciona en forma independiente entre el grupo que comprende halógeno, alquilo, arilo, cicloalquilo, heterociclilalquilo, CF3, OCF3, CN, -OR5, -NR4R5, -N(R5)Boc, -(CR4R5)nOR5, -C(O2)R5, -C(O)NR4R5, -C(O)R5, -SO3H, -SR5, -S(O2)R7, -S(O2)NR4R5, -N(R5)S(O2)R7, -N(R5)C(O)R7 y -N(R5)C(O)NR4R5; u opcionalmente, (i) R5 y R10 en la porción -NR5R10, o (ii) R5 y R6 en la porción -NR5R6 pueden unirse para formar una porción cicloalquilo o heterociclilo, en donde cada porción cicloalquilo o heterociclilo está insustituida o en forma opcional, independientemente sustituida con uno o más grupos R9; R7 se selecciona entre el grupo que consiste en alquilo, cicloalquilo, arilo, heteroarilo, arilalquilo y heteroarilalquilo, en donde cada uno de dichos alquilo, cicloalquilo, heteroarilalquilo, arilo, heteroarilo y arilalquilo pueden estar insustituidos u opcionalmente sustituidos de manera independiente con uno o más porciones iguales o diferentes, en donde cada porción se selecciona en forma independiente entre el grupo que comprende halógeno, alquilo, arilo, cicloalquilo, CF3, OCF3, CN, -OR5, -NR5R10, -CH2OR5, -C(O2)R5, -C(O)NR5R10, -C(O)R5, -SR10, -S(O2)R10, -S(O2)NR5R10, -N(R5)S(O2)R10, -N(R5)C(O)R10 y -N(R5)C(O)NR5R10; R8 se selecciona entre el grupo que consiste en R6, -C(O)NR5R10, -S(O2)NR5R10, -C(O)R7 y -S(O2)R7; R9 se selecciona entre el grupo que consiste en halógeno, CN, -NR5R10, -C(O2)R6, -C(O)NR5R10, -OR6, -SR6, -S(O2)R7, -S(O2)NR5R10, -N(R5)S(O2)R7, -N(R5)C(O)R7 y -N(R5)C(O)NR5R10; m es 0 a 4; y n es 1 a 4. Reivindicación 30: El método de la reivindicación 29, en donde dicha cinasa dependiente de ciclina es CDK2. Reivindicación 31: El método de la reivindicación 29, en donde dicha enfermedad se selecciona entre el grupo que comprende: cáncer de la vejiga, mama, colon, rinón, hígado, pulmón, cáncer de pulmón de célula pequena, esófago, vesícula biliar, ovario, páncreas, estómago, cervical, tiroides, próstata y piel, incluyendo carcinoma de célula escamosa; leucemia, leucemia del tipo linfocitosis aguda, leucemia de linfoblasto aguda, linfoma de célula B, linfoma de célula T, linfoma de Hodgkins, linfoma no Hodgkins, linfoma de células veleosas y linfoma de Burkett; leucemia mielógena aguda y crónica, síndrome mielodisplástico, leucemia promielocítica; fibrosarcoma, rabdomiosarcoma; astrocitoma, neublastoma, glioma y schwannomas; melanoma, seminoma, teratocarcinoma, osteosarcoma, xenoderoma pigmentosum, queratoacantoma, cáncer folicular tiroideo y sarcoma de Kaposi.
ARP030103191A 2002-09-04 2003-09-03 Pirazolopirimidinas como inhibidores de cinasas dependientes de clclinas AR041136A1 (es)

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US (3) US7074924B2 (es)
EP (1) EP1534710B1 (es)
JP (2) JP4700344B2 (es)
KR (1) KR20050057139A (es)
CN (1) CN1701074A (es)
AR (1) AR041136A1 (es)
AT (1) ATE376548T1 (es)
AU (1) AU2003268385B2 (es)
CA (1) CA2497450C (es)
DE (1) DE60317077T2 (es)
ES (1) ES2291665T3 (es)
HK (1) HK1071569A1 (es)
IL (1) IL167088A (es)
MX (1) MXPA05002570A (es)
MY (2) MY141978A (es)
NZ (1) NZ539164A (es)
PE (1) PE20040999A1 (es)
TW (1) TWI335919B (es)
WO (1) WO2004022560A1 (es)
ZA (1) ZA200501852B (es)

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MXPA05002570A (es) 2005-09-08
AU2003268385B2 (en) 2006-12-21
KR20050057139A (ko) 2005-06-16
TW200420564A (en) 2004-10-16
US7309705B2 (en) 2007-12-18
JP4700344B2 (ja) 2011-06-15
CN1701074A (zh) 2005-11-23
MY141978A (en) 2010-08-16
ATE376548T1 (de) 2007-11-15
DE60317077T2 (de) 2008-07-24
MY137888A (en) 2009-03-31
US7074924B2 (en) 2006-07-11
JP2010168406A (ja) 2010-08-05
JP2006502161A (ja) 2006-01-19
ES2291665T3 (es) 2008-03-01
CA2497450C (en) 2011-05-31
US20040116442A1 (en) 2004-06-17
CA2497450A1 (en) 2004-03-18
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US20070275983A1 (en) 2007-11-29
WO2004022560A9 (en) 2005-07-07
ZA200501852B (en) 2005-09-08
US20060173016A1 (en) 2006-08-03
IL167088A (en) 2010-12-30
NZ539164A (en) 2006-04-28
DE60317077D1 (de) 2007-12-06
EP1534710B1 (en) 2007-10-24
PE20040999A1 (es) 2004-12-28
AU2003268385A1 (en) 2004-03-29
US7511049B2 (en) 2009-03-31
EP1534710A1 (en) 2005-06-01
HK1071569A1 (en) 2005-07-22

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