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AR063527A1 - Derivados biciclicos fusionados de 2,4-diaminopirimidina como inhibidores de alk y c-met - Google Patents

Derivados biciclicos fusionados de 2,4-diaminopirimidina como inhibidores de alk y c-met

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Publication number
AR063527A1
AR063527A1 ARP070104687A ARP070104687A AR063527A1 AR 063527 A1 AR063527 A1 AR 063527A1 AR P070104687 A ARP070104687 A AR P070104687A AR P070104687 A ARP070104687 A AR P070104687A AR 063527 A1 AR063527 A1 AR 063527A1
Authority
AR
Argentina
Prior art keywords
alkyl
cycloalkyl
membered heteroaryl
aryl
membered heterocycloalkyl
Prior art date
Application number
ARP070104687A
Other languages
English (en)
Inventor
Rabindranath Tripathy
Gregory R Ott
Jonathan Parrish
Ming You
Craig A Zificsak
Jason C Wagner
Linda Weinberg
Matthew A Curry
Tao Guo
Daming Feng
Koc-Kan Ho
Keith S Learn
Rong-Giang Liu
Eugen Mesaros
Benjamin J Dugan
Karen Milkiewicz
Bruce Dprsey
Guizar Ahmed
Adolph Bohnstedt
Diane E Gingrich
Henry Joseph Breslin
Jason Burke
Theodore L Underiner
James L Diebold
Joseph G Lisko
Jay P Theroff
Tho V Thieu
Gregory J Wells
Original Assignee
Cephalon Inc
Pharmacopeia Inc
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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Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39050187&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR063527(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Cephalon Inc, Pharmacopeia Inc filed Critical Cephalon Inc
Publication of AR063527A1 publication Critical patent/AR063527A1/es

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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
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Los compuestos de la formula 1 o 2 tienen actividad inhibitoria de ALK y/o c-Met y pueden utilizarse para tratar trastornos proliferativos. Reivindicacion 1: En una incorporacion, la presente invencion proporciona un compuesto de la formula (1) o (2) o una sal farmacéuticamente aceptable del mismo, caracterizado porque R1 es H, halogeno, -NO2, -OR10, -C(=O)R10, -C(=O)OR10, C(=O)NR12R13, -NR10R11, -C1-6-alquil, -C1-6-alquil-OR10, -C1-6- alquil-NR12R13, C1-6-haloalquil, C2-6-alquenil, C2-6- alquinil, C6-15-aril, heteroarilo de 5-15 miembros, C3-10-cicloalquil, heterocicloalquilo de 3-15 miembros, pseudohalogeno, -S(=O)nR10, -S(=O)2NR12R13, -OCH2F, -OCRF2, -OCF3, -NHOH, -OC(=O)R10, -OC(=O)NR12R13, -NR10C(=O)R11, -NR10C(=O)OR11, - NR10S(=O)2R11, -NR10C(=O)NR12R13, -NR10S(=O)2NR12R13, o -SCF3; R2 es un grupo elegido de C1-6-alquil, C2-6-alquenil, C2-6-alquinil, C6-15-aril, C3-10-cicloalquil, heterocicloalquilo de 3-15 miembros, y heteroarilo de 5-15 miembros, caracterizado porque el grupo R2 se sustituye opcionalmente por uno o más miembros independientemente elegidos de halogeno, -NO2, -OR20,=O, -C(=O)R20, -C(O)OR20, -C(O)NR22R23, -NR20R21, C1-6-alquil-(R25)x, C6-15-aril-(R25)x, heteroarilo de 5-15 miembros -(R25)x, C3-10 cicloalquil-(R25)x, heterocicloalquilo de 3-15 miembros-(R25)x, pseudohalogeno, -S(=O)nR20, -S(=O)2NR22R23, -OCH2F, -OCHF2, -OCF3, -NHOH, -OC(=O)R20, -OC(=O)NR22R23, -NR20C(=O)R21, -NR20C(=O)OR21, -NR20S(O)2R21, -NR20C(=O)NR22R23, - NR20S(=O)2NR22R23, y -SCR3; R3, R4 y R5 se eligen independientemente de H, halogeno, -NO2, -OR30, -C(=O)R30, -C(=O)OR30, -C(=O)NR32R33, -NR30R31, C1-6-alquil-(R35)x, C6-15-aril-(R35)x, heteroarilo de 5-15 miembros -(R35)x, C3-10 cicloalquil-(R35)x, heterocicloalquilo de 3-15 miembros-(R35)x, pseudohalogeno, -S(=O)nR30, -S(=O)2NR32R33, -OCH2F, -OCHF2, -OCF3, -NHOH, -OC(=O)R30, -OC(=O)NR32R33, -NR30C(=O)R31, -NR30C(O)OR31, -NR30S(=O)2R31, -NR30C(O)NR32R33, -NR30S(=O)2NR32R33, y -SCF3; A1, A2, A3, A4, y A5 son cada uno independientemente -Cz1Z2-, -(CZ1Z2)2-, -C(=O)-, -NZ3-, -S-, -S(=O)-, -S(=O)2-, o-O-, con la condicion de que al menos uno de A1, A2, A3, A4, y A5 es -(CZ1Z2)2-, caracterizado porque: (a) cuando dos cualquiera de Z1, Z2, y Z3 se ubican en átomos adyacentes, pueden formar una union entre los átomos, (b) cualquiera de Z1, Z2, y Z3 puede ser independientemente elegido de H halogeno, -NO2, -OR40, -C(=O)R40, -C(=O)OR40, -C(=O)OR40, -C(=O)NR42R43, -NR40R41, C1-6-alquil- (R45)x, C6-15-aril-(R45)x, heteroarilo de 5-15 miembros -(R45)x, C3-10 cicloalquil-(R45)x, heterocicloalquilo de 3-15 miembros-(R45)x, C2-6-alquenil-(45)x, C2-6-alquinil-(R45)x, pseudohalogeno, S(O)nR40, -S(=O)2NR42R43, -OCH2F, -OCHF2, -OCF3, - NHOH, --OC(=O)R4, -OC(=O)NR42R43, -NR40C(=O)R41, -NR40C(=O)OR41, -NR40S(=O)2R41, -NR40C(=O)NR42R43, -NR40S(=O)2NR42R43, y -SCF3, y (c) dos cualesquiera de Z1, Z2, y Z3 pueden juntos formar un grupo de la formula -A6-A7-A8-A9-A10-, caracterizado porque A6, A7, A8, A9, y A10 se eligen independientemente de una union, -CZ4Z5-, -C(=O)-, -NZ6-, -S-, -S(=O)-, -S(=O)2-, o-O-, caracterizado porque: (i) cuando dos cualesquiera de Z1, Z2, Z3, Z4, Z5, y Z6 se ubican en átomos adyacentes, pueden formar una union entre dos átomos, y (ii) cualquiera de Z4, Z5, y Z6 puede ser independientemente elegido de H, halogeno, -NO2, -OR50, -C(=O)R50, -C(=O)OR50, -C(=O)NR52R53, -NR50R51, C1-6-alquil- (R55)x, C6-15-aril- (R55)x, heteroarilo de 5-15 miembros -(R55)x , C3-10 cicloalquil-(R55)x, heterocicloalquilo de 3-15 miembros-(R55)x, pseudohalogeno, -S(=O)nR50, -S(=O)2NR52R53, -OCH2F, -OCHF2, -OCF3, -NHOH, -OC(=O)R50, OC(=O)NR52R53, -NR50C(=O)R51, -NR50C(=O)OR51, -NR50S(=O)2R51, - NR50C(=O)NR52R53, -NR50S(=O)2NR52R53, y -SCF3; R25, R35, R45, y R55 en cada frecuencia se eligen independientemente de halogeno, -NO2, -OR60, =O, -C(=O)R60, -C(=O)OR60, -C(=O)NR62R63, -NR60R61, C1-6-alquil, -C1-6-alquil-O-C1-6-alquil, C1-6- haloalquil, C2-6-alquenil, C2-6-alquinil, C6-15-aril- (R77)x , heteroarilo de 5-15 miembros -(R77)x, C3-10 cicloalquil-(R77)x, heterocicloalquilo de 3-15 miembros-(R77)x, pseudohalogeno, -S(=O)nR60, -S(=O)2NR62R63, -OCH2F, -OCHF2, -OCF3, -NHOH, - OC(=O)R60, -OC(=O)NR62R63, -OP(=O)(OH)2, -NR60C(=O)R61, -NR60C(=O)OR61, -NR60S(=O)2R61, -NR60C(=O)NR62R63, -NR60S(=O)2NR62R63, y -SCF3; R10, R11, R20, R21, R30, R31, R40, R41, R50, R51, R60, y R61 en cada frecuencia se eligen independientemente de H, C1-6-alquil, C2-6-alquinil, C1-6-haloalquil, C6-15-aril, heteroarilo de 5-15 miembros, C3-10 cicloalquil, y heterocicloalquilo de 3-15 miembros, en el cual dichos grupos de C1-6-aiquil, C2-6-alquinil, C1-6-haloalquil, C6-15- aril, heteroarilo de 5-15 miembros, C3-10 cicloalquil, y heterocicloalquilo de 3-15 miembros se sustituyen opcionalmente por uno o mas sustituyentes independientemente elegidos de C1-6-alquil, C2-6-alquenil, C2-6-alquinil, halogeno, ciano, fenil, heteroarilo de 5-10 miembros -(R79)x, heterocicloalquilo de 3-10 miembros, -N(R76)2, -C(=O)OR76, -C(=O)N(R76)2, =O, y -OR76; R12, R13, R22, R23, R32, R33, R42, R43, R52, R53, R62, y R63 en cada frecuencia se eligen independientemente de H, C1-6-alquil, C2-6-alquinil, C1-6-haloalquil, C6-15-aril, heteroarilo de 5-15 miembros, C3-10 cicloalquil, y heterocicloalquilo de 3-15 miembros, en el cual dichos grupos de C1-6-alquil, C2-6-alquinil, C1-6-haloalquil, C6-15-aril, heteroarilo de 5-15 miembros , C3-10 cicloalquil, y heterocicloalquilo de 3-15 miembros se sustituyen opcionalmente por uno o mas sustituyentes independientemente elegidos de C1-6-alquil, halogeno, C3-10 cicloalquil, heterocicloalquilo de 3-10 miembros-(R87)x, -N(R86)2, ciano, C2-6- alquinil, =O, y -OR86; o R12 y R13, R22 y R23, R32 y R33, R42 y R43, R52 y R53, o R62 y R63 pueden formar, junto con el átomo de nitrogeno al cual se unen, un grupo heterocicloalquilo de 3-15 miembros o un grupo heteroarilo de 5-15 miembros, en el cual dicho grupo heterocicloalquilo de 3-15 miembros o grupo heteroarilo de 5-15 miembros se sustituye opcionalmente por uno o mas sustituyentes independientemente elegidos de C1-6-alquil, halogeno, y -OH; R76 y R86 en cada frecuencia se eligen independientemente de H, C1-6-alquil-(R78)x, y -C(=O)-C1-6-alquil; R77 y R87 en cada frecuencia se eligen independientemente de C1-6-alquil; R78 en cada frecuencia es independientemente elegido de =O y fenil; R79 en cada frecuencia es =O; n en cada frecuencia es independientemente elegido de 0, 1, y 2; y x en cada frecuencia es independientemente elegido de 0, 1, 2, 3, 4, 5, y 6; con la condicion de que el compuesto no sea: (a); (b); (c), caracterizado porque R=H o-C(=O)CF3; (d), caracterizado porque R=Br, Cl, CH3, o CF3; (e), caracterizado porque R=Br, Cl, o CH3; (f), caracterizado porque X = grupo de formulas (3); (g); (h), caracterizado porque R = H, etil, -C(=O)CH3, -C(=O)CH(CH3)2, -C(=O)CH2OCH3, -C(=O)NHCH(CH3)2, -C(=O)CH2NHC(O)CH3, - C(=O)CHF2, -C(=O)CF3, -C(=O)NHCH2CH3, -C(=O)CH2N(CH3)2, formula (4), 2-piridil, o S-(=O)2CH3, y R' = ciclopropil, ciclobutil, -CH2-ciclopropil, etil, -CH(CH3)2, propil, metil, formula (5), -(CH2)2OCH3, o formula (6); o (i) formula (7).
ARP070104687A 2006-10-23 2007-10-23 Derivados biciclicos fusionados de 2,4-diaminopirimidina como inhibidores de alk y c-met AR063527A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US85356206P 2006-10-23 2006-10-23
PCT/US2007/022496 WO2008051547A1 (en) 2006-10-23 2007-10-23 Fused bicyclic derivatives of 2,4-diaminopyrimidine as alk and c-met inhibitors

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AR063527A1 true AR063527A1 (es) 2009-01-28

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US (2) US8148391B2 (es)
EP (2) EP2684874B1 (es)
JP (1) JP5512274B2 (es)
CN (1) CN101535276B (es)
AR (1) AR063527A1 (es)
AU (1) AU2007309427B2 (es)
CA (1) CA2669111C (es)
CL (1) CL2007003049A1 (es)
ES (2) ES2633318T3 (es)
HK (1) HK1147748A1 (es)
IL (1) IL198150A (es)
MX (1) MX2009004426A (es)
NZ (1) NZ576425A (es)
TW (1) TWI432427B (es)
WO (1) WO2008051547A1 (es)

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MX2009006081A (es) 2006-12-08 2009-06-17 Irmc Llc Compuestos y composiciones como inhibidores de cinasa de proteina.

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EP2222647B1 (en) 2015-08-05
US20090221555A1 (en) 2009-09-03
CA2669111C (en) 2016-04-12
AU2007309427A1 (en) 2008-05-02
MX2009004426A (es) 2009-08-12
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EP2684874B1 (en) 2017-05-17
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AU2007309427B2 (en) 2013-02-28
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