AR044703A1 - Cis-2,4,5 triaril- imidazolinas y su actividad antiproliferativa - Google Patents

Cis-2,4,5 triaril- imidazolinas y su actividad antiproliferativa

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Publication number
AR044703A1
AR044703A1 ARP040102068A ARP040102068A AR044703A1 AR 044703 A1 AR044703 A1 AR 044703A1 AR P040102068 A ARP040102068 A AR P040102068A AR P040102068 A ARP040102068 A AR P040102068A AR 044703 A1 AR044703 A1 AR 044703A1
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AR
Argentina
Prior art keywords
lower alkyl
substituted
group
heterocycle
chosen
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ARP040102068A
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English (en)
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Hoffmann La Roche
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Publication of AR044703A1 publication Critical patent/AR044703A1/es

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    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/10—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 carbon chain containing aromatic rings
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D403/10—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 carbon chain containing aromatic rings
    • 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
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Estos compuestos inhiben la interacción de la proteína MDM2 con un péptido del tipo p53 y tienen actividad antiproliferativa. Reivindicación 1: Por lo menos un compuesto elegido entre los compuestos de la fórmula (1), en la que: X1 y X2 son halógeno; X3 es alcoxi inferior; R se elige entre un resto del grupo de fórmulas (2), en las que: R1 se elige entre el grupo formado por: N-alquilo inferior; heterociclo sin sustituir y heterociclo sustituido con uno o varios sustituyentes elegidos entre el grupo formado por: NH2, NH-C(O)-alquilo inferior, C(O)-alquilo inferior, C(O)-alcoxi inferior, oxo, heterociclo y alquilo inferior sustituido con hidroxi; R2 se elige entre hidrógeno y metilo; R3 se elige entre el grupo formado por: heteroarilo; heterociclo; y CH2-R7; R4 se elige entre el grupo formado por: C(O)-alcoxi inferior; alcoxi inferior; -CH2-N-alquilo inferior; CH2-heterociclo; CH2-heterociclo sustituido con oxo; arilo; NH-C(S)-alquilo inferior; NH-C(S)-N-arilo y NH- C(O)-R8; R5 se elige entre el grupo formado por oxo; heteroarilo; arilo sustituido con un sustituyente elegido entre alcoxi inferior y flúor; C(S)-N-alquilo inferior; C(S)-N-arilo; C(O)-CH2-R12; C(O)-R13; SO2-R14 y alquilo inferior sustituido con un sustituyente elegido entre R15 y C(O)-R16; R6 se elige entre el grupo formado por: alquilo inferior sustituido con N-alquilo inferior; heterociclo inferior sustituido con heterociclo; alquilo inferior sustituido con heterociclo sustituido con uno o dos sustituyentes elegidos entre alquilo inferior, alquilo inferior sustituido con hidroxilalquilo inferior sustituido con alcoxi inferior y oxo; R7 se elige entre el grupo formado por: ciano; hidroxi; alcoxi inferior; heteroarilo; heterociclo; heterociclo sustituido con oxo; N-alquilo inferior; y arilo sustituido con un sustituyente elegido entre el grupo formado por SO2NH2, alcoxi inferior e hidroxi; R8 se elige entre el grupo formado por: N-alquilo inferior; heterociclo; heterociclo sustituido con un sustituyente elegido entre el grupo formado por oxo, C(O)-NH2 y C(O)-NH-alquilo inferior; CH2-R9 y CH2-R10; R9 se elige entre el grupo formado por: NH2; N-alquilo inferior; N-alquilo inferior sustituido con un sustituyente elegido entre hidroxi y alcoxi inferior; C(O)-NH-alcoxi inferior; C(O)-NH-benciloxi; C(O)-heterociclo sustituido con un sustituyente elegido entre trifluormetilo e hidroxi y C(O)-NH-R11; R10 se elige entre un heterociclo y heterociclo sustituido con uno o varios grupos elegidos entre el grupo formado por C(O)-alquilo inferior, C(O)-NH2, C(O)-N-alquilo inferior, alquilo inferior sustituido con hidroxi, hidroxi, alcoxi inferior y oxo; R11 se elige entre alquilo inferior; y alquilo inferior sustituido con un sustituyente elegido entre el grupo formado por alcoxi, heteroarilo sustituido con alquilo inferior, ciano y trifluormetilo; R12 se elige entre el grupo formado por alcoxi inferior; NH2; N-alquilo inferior; N-alquilo inferior sustituido con un sustituyente elegido entre hidroxi y alcoxi inferior; heteroarilo; y heterociclo sustituido con R17; R13 se elige entre el grupo formado por: heteroarilo; heteroarilo sustituido con uno o dos sustituyentes elegidos entre el grupo formado por alquilo inferior, arilo y halógeno; heterociclo; heterociclo sustituido con uno o varios sustituyentes elegidos entre el grupo formado por alquilo inferior, arilo y halógeno; C(O)-alquilo inferior; C(O)-NH2; C(O)-N-alquilo inferior; y oxo; R14 se elige entre el grupo formado por: trifluormetilo; alquilo inferior; arilo sustituido con alquilo inferior; NH2; N-alquilo inferior; N-alquilo inferior sustituido con un sustituyente elegido entre alcoxi inferior y ciano; heteroarilo; heteroarilo sustituido con un sustituyente elegido entre el grupo formado por halógeno, hidroxi, oxo, C(O)-alcoxi inferior, alquilo inferior y alquilo inferior sustituido con hidroxilo; heterociclo y heterociclo sustituido con un sustituyente elegido entre el grupo formado por halógeno, hidroxi, oxo, C(O)-alcoxi inferior, alquilo inferior y alquilo inferior sustituido con hidroxilo; R15 se elige entre el grupo formado por alcoxi inferior; ciano; trifluormetilo; N-alquilo inferior; SO2-alquilo inferior; C(O)-alquilo inferior; SO2-NH2; SO2-N-alquilo inferior; heteroarilo y heterociclo; R16 se elige entre el grupo formado por: alcoxi inferior; NH2; N-alquilo inferior; N-alcoxi inferior; N-benciloxi; N-alquilo inferior sustituido con R18; heterociclo y heterociclo sustituido con uno o dos sustituyentes elegidos entre el grupo formado por hidroxi, alcoxi, trifluormetilo, C(O)-alquilo inferior, C(O)-NH2, C(O)-N-alquilo inferior, alquilo inferior sustituido con hidroxi y oxo; R17 se elige entre el grupo formado por: C(O) -alquilo inferior; C(O)-NH2; C(O)-N-alquilo inferior; hidroxi; oxo y alquilo inferior sustituido con hidroxi; y R18 se elige entre el grupo formado por: alcoxi inferior; ciano; trifluormetilo; heterociclo e hidroxilo; o una sal o un éster farmacéuticamente aceptable del mismo.
ARP040102068A 2003-06-17 2004-06-15 Cis-2,4,5 triaril- imidazolinas y su actividad antiproliferativa AR044703A1 (es)

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US47935103P 2003-06-17 2003-06-17

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ARP040102068A AR044703A1 (es) 2003-06-17 2004-06-15 Cis-2,4,5 triaril- imidazolinas y su actividad antiproliferativa

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EP (1) EP1638942A1 (es)
JP (1) JP2006527712A (es)
KR (1) KR100768021B1 (es)
CN (1) CN100465163C (es)
AR (1) AR044703A1 (es)
AU (1) AU2004254187A1 (es)
BR (1) BRPI0411841A (es)
CA (1) CA2528119A1 (es)
CL (1) CL2004001484A1 (es)
MX (1) MXPA05013279A (es)
RU (1) RU2319696C2 (es)
TW (1) TW200510387A (es)
WO (1) WO2005003097A1 (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100031783A (ko) * 2005-03-16 2010-03-24 에프. 호프만-라 로슈 아게 시스-２，４，５-트리아릴-이미다졸린 및 항암 약제로서의 그의 용도
AU2006319248B2 (en) * 2005-12-01 2012-09-27 F.Hoffman-La Roche Ag 2,4,5-triphenyl imidazoline derivatives as inhibitors of the interaction between P53 and MDM2 proteins for use as anticancer agents
US8114095B2 (en) * 2006-11-10 2012-02-14 Bausch & Lomb Incorporated Intraocular lens injection apparatus and method
BRPI0720546A2 (pt) 2006-12-14 2015-06-23 Daiichi Sankyo Co Ltd Composto, inibidor, medicamento, agente antitumor, composição farmacêutica, método para tratar câncer, e, uso do composto
US7625895B2 (en) * 2007-04-12 2009-12-01 Hoffmann-Le Roche Inc. Diphenyl-dihydro-imidazopyridinones
WO2009151069A1 (ja) 2008-06-12 2009-12-17 第一三共株式会社 ４，７－ジアザスピロ［２．５］オクタン環構造を有するイミダゾチアゾール誘導体
CN102356085A (zh) 2009-01-16 2012-02-15 第一三共株式会社 具有脯氨酸环结构的咪唑并噻唑衍生物
IT1396520B1 (it) 2009-12-10 2012-12-14 Nuovo Pignone Spa Accoppiamento per bilanciamento rotore
WO2013054153A1 (en) 2011-10-11 2013-04-18 INSERM (Institut National de la Santé et de la Recherche Médicale) Nutlin compounds for use in he treatment of pulmonary hypertension
CN109152843A (zh) 2016-05-20 2019-01-04 豪夫迈·罗氏有限公司 Protac抗体缀合物及其使用方法
WO2023056069A1 (en) 2021-09-30 2023-04-06 Angiex, Inc. Degrader-antibody conjugates and methods of using same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2030158A1 (en) * 1989-11-22 1991-05-23 Nahed K. Ahmed Cancer treatments
DE10043456A1 (de) * 2000-09-04 2002-03-14 Merck Patent Gmbh Verwendung von Ectoin oder Ectoin-Derivaten zur Stabilisierung von p53
RU2305095C2 (ru) * 2001-12-18 2007-08-27 Ф.Хоффманн-Ля Рош Аг Цис-2,4,5-трифенилимидазолины и фармацевтическая композиция на их основе

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TW200510387A (en) 2005-03-16
MXPA05013279A (es) 2006-03-09
RU2319696C2 (ru) 2008-03-20
BRPI0411841A (pt) 2006-08-08
CA2528119A1 (en) 2005-01-13
JP2006527712A (ja) 2006-12-07
CN1809538A (zh) 2006-07-26
KR20060021902A (ko) 2006-03-08
WO2005003097A1 (en) 2005-01-13
CN100465163C (zh) 2009-03-04
AU2004254187A1 (en) 2005-01-13
KR100768021B1 (ko) 2007-10-18
EP1638942A1 (en) 2006-03-29
RU2006100730A (ru) 2006-08-10
CL2004001484A1 (es) 2005-05-27

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