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ES2616477T3 - Heterociclaminas como inhibidores de pi3k - Google Patents

Heterociclaminas como inhibidores de pi3k Download PDF

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ES2616477T3
ES2616477T3 ES12775861.3T ES12775861T ES2616477T3 ES 2616477 T3 ES2616477 T3 ES 2616477T3 ES 12775861 T ES12775861 T ES 12775861T ES 2616477 T3 ES2616477 T3 ES 2616477T3
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alkenyl
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Yun-Long Li
Wenqing Yao
Andrew P. Combs
Eddy W. Yue
Song MEI
Wenyu Zhu
Joseph Glenn
Thomas P. Maduskuie, Jr.
Richard B. Sparks
Brent Douty
Chunhong He
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Incyte Holdings Corp
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Un compuesto de Fórmula I: **Fórmula** o una sal farmacéuticamente aceptable del mismo, en donde: X es CR9 o N; W es CR7 o N; Y es CR8, CR8a, o N; Z es un enlace o C(>=O); siempre que -W>=Y-Z- es -CR7>=CR8, -N>=CR8-, -CR7>=CR8a -C(>=O)-, -N>=CR8a -C(>=O)-o -CR7>=NC(>=O)-; R1 es alquilo C1-3; R2 es halo, alquilo C1-6, alcoxi C1-6, haloalquilo C1-6, haloalcoxi C1-6, fenilo o heteroarilo de 5 a 6 miembros; donde dicho fenilo y heteroarilo de 5 a 6 miembros están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 sustituyentes seleccionados independientemente de halo, OH, CN, alquilo C1-4, alcoxi C1-4, y haloalcoxi C1-4; R3 es Cy,-(alquileno C1-3)-cy, halo, CN, NO2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6 ORa, SRa, C(>=O)Rb, C(>=O)NRcRd, C(>=O)ORa, OC(>=O)Rb, OC(>=O)NRcRd, NRcRd, NRcC(>=O)Rb, NRc>=C(>=O)ORb, NRcC(>=O)NRcRd, C(>=NRe)Rb, C(>=NRe) NRcRd, NRcC(>=NRe) NRcRd, NRcS(>=O)2Rb, NRcS(>=O)2NRcRd, S(>=O)2Rb, o S(>=O)2NRcRd; en el que dicho alquilo C1-6, alquenilo C2-6 y alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 grupos independientemente seleccionados 43a; R4 es H, halógeno, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, o haloalcoxi C1-4; R5 es halo, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, haloalcoxi C1-4, o ciclopropilo; R6 es H, halo, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, o haloalcoxi C1-4; R7 es H o alquilo C1-4; R7 es H, halo, -OH, -CN, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, Cy2 ,-(alquileno C1-3)-Cy2, ORa2 SRa2, C(>=O)Rb2, C(>=O)NRc2Rd2, C(>=O)ORa2, OC(>=O)Rb2, OC(>=O)NRc2Rd2, NRc2Rd2, NRc2C(>=O)Rb2, NRc2C(>=O)ORb2, NRc2C(>=O)NRc2Rd2, C(>=NRe)Rb2, C(>=NRe) NRc2Rd2, NRc2C(>=NRe) NRc2Rd2, NRc2S(>=O)Rb2, NRc2S(>=O)2NRc2Rd2, S(>=O)Rb2, S(>=O)2Rb2, o S(>=O)2NRc2Rd2; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 grupos seleccionados independientemente R11; R8a es H, halo, -CN, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, Cy2 ,-(alquileno C1-3)-Cy2, C(>=O)Rb2, C(>=O)NRc2Rd2, C(>=O)ORa2, NRc2Rd2, NRc2C(>=O)Rb2, NRc2C(>=O)ORb2, NRc2C(>=O)NRc2Rd2, NRc2S(>=O)Rb2, NRc2S(>=O)2NRc2Rd2, S(>=O)Rb2, S(>=O)2Rb2, o S(>=O)2NRc2Rd2; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 grupos seleccionados independientemente R11; R7 es H, halógeno, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, o haloalcoxi C1-4; R10 es H o alquilo C1-4; cada Ra, Rb, Rc y Rd se selecciona independientemente de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6 y Cy; en el que dicho alquilo C1-6, alquenilo C2-6 y alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2 ó 3 grupos R3b seleccionados independientemente; o Rc y Rd junto con el átomo N al que están unidos forman un grupo de heterocicloalquilo de 4, 5, 6, o 7 miembros, el cual está opcionalmente sustituido por -OH o alquilo C1-3; cada Re se selecciona independientemente de H, CN, OH, alquilo C1-4, y alcoxi C1-4; cada Cy se selecciona independientemente de cicloalquilo C3-7, heterocicloalquilo de 4 a 10 miembros, fenilo, naftilo, y heteroarilo de 5 a 10 miembros, cada uno de los cuales está opcionalmente sustituido por 1, 2, 3, o 4 grupos R3b seleccionados independientemente; cada R3a se selecciona independientemente de halo, CN, NO2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, ORa1, SRa1, C(>=O)Rb1, C(>=O)NRc1Rd1, C(>=O)ORa1, OC(>=O)Rb1, OC(>=O)NRc1Rd1, NRc1Rd1, NRc1C(>=O)Rb1, NRc1C(>=O)ORb1, NRc1C(>=O)NRc1Rd1, C(>=NRe)Rb1, C(>=NRe) NRc1Rd1, NRc1C(>=NRe), NRc1Rd1, NRc1S(>=O)Rb1, NRc1S(>=O)2NRc1Rd1, S(>=O)2Rb1, y S(>=O)2NRc1Rd1; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2 ó 3 grupos R11 seleccionados independientemente; cada R3b se selecciona independientemente de Cy1 ,-(alquileno C1-3)-cy1, halo, CN, NO2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, ORa1, SRa1, C(>=O)Rb1, C(>=O)NRc1Rd1, C(>=O)ORa1, OC(>=O)Rb1, OC(>=O)NRc1Rd1, NRc1Rd1, NRc1C(>=O)Rb1, NRc1C(>=O)ORb1, NRc1C(>=O)NRc1Rd1, C(>=NRe)Rb1, C(>=NRe) NRc1Rd1, NRc1C(>=NRe) NRc1Rd1, NRc1S(>=O)Rb1, NRc1S(>=O)2NRc1Rd1, S(>=O)Rb1, S(>=O)2Rb1, y S(>=O)2NRc1Rd1; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2 ó 3 grupos R11 seleccionados independientemente; cada Cy1 se selecciona independientemente de cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, y heteroarilo de 5 a 6 miembros, cada uno de los cuales está opcionalmente sustituido por 1, 2, 3, o 4 grupos R11 seleccionados independientemente ; cada Ra1, Rb1, Rc1, y Rd1 se selecciona independientemente de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, y heteroarilo de 5 a 6 miembros; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, Cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo y heteroarilo de 5 a 6 miembros están cada uno opcionalmente sustituidos por 1, 2 o 3 grupos R11 seleccionados independientemente; o Rc1y Rd1 junto con el átomo N al que están unidos forman un grupo de heterocicloalquilo de 4, 5, 6, 7 miembros, que está opcionalmente sustituido por -OH o alquilo C1-3; cada Cy2 se selecciona independientemente de cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, heteroarilo de 5 a 6 miembros o heteroarilo bicíclico de 9 a 10 miembros, cada uno de los cuales está opcionalmente sustituido por 1, 2, 3, o 4 grupos R11 seleccionados independientemente; cada Ra2, Rb2, RC2, y Rd2 se selecciona independientemente de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, Cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, y heteroarilo de 5 a 6 miembros; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, heterocicloalquilo de 4-7 miembros, fenilo y heteroarilo de 5 a 6 miembros están cada uno opcionalmente sustituidos por 1, 2 o 3 grupos R11 seleccionados independientemente; o Rc2 y Rd2 junto con el átomo N al que están unidos forman un grupo de heterocicloalquilo de 4, 5, 6, o 7 miembros, que está opcionalmente sustituido por -OH o alquilo C1-3; y cada R11 se selecciona independientemente de OH, NO2, CN, halo, alquilo C1-3, alquenilo C2-3, alquinilo C2-3, haloalquilo C1-3, ciano-alquilo C1-3, HO-alquilo C1-3, alcoxi C1-3-alquilo C1-3, cicloalquilo C3-7, alcoxi C1-3, haloalcoxi amino C1-3, alquilamino C1-3, di(alquilo C1-3)amino, tio, alquiltio C1-3, alquilsulfinilo C1-3, alquilsulfonilo C1-3, carbamilo, alquilcarbamilo C1-3, di(alquilo C1-3)carbamilo, carboxi, alquilcarbonilo C1-3, alcoxicarbonilo C1-4, alquilcarbonilamino C1-3, alquilsulfonilamino C1-3, aminosulfonilo, alquilaminosulfonilo C1-3, di(alquilo C1-3)aminosulfonilo, aminosulfonilamino, alquilaminosulfoniloamino C1-3, di(alquilo C1-3)aminosulfonilamino, aminocarbonilamino, alquilaminocarbonilamino C1-3, y di(alquilo C1-3)aminocarbonilamino; en el que los átomos y heteroátomos de un grupo de heterocicloalquilo de carbono que forman anillo pueden estar opcionalmente sustituidos con oxo o sulfido.
ES12775861.3T 2011-09-02 2012-08-31 Heterociclaminas como inhibidores de pi3k Active ES2616477T3 (es)

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US201161530866P 2011-09-02 2011-09-02
US201161530866P 2011-09-02
US201261594882P 2012-02-03 2012-02-03
US201261594882P 2012-02-03
US201261677445P 2012-07-30 2012-07-30
US201261677445P 2012-07-30
PCT/US2012/053398 WO2013033569A1 (en) 2011-09-02 2012-08-31 Heterocyclylamines as pi3k inhibitors

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