AR092491A1 - Derivados de imidazolin-5-ona utiles como inhibidores de fasn para el tratamiento contra el cancer - Google Patents
Derivados de imidazolin-5-ona utiles como inhibidores de fasn para el tratamiento contra el cancerInfo
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Abstract
Se dan a conocer compuestos, composiciones y métodos para el tratamiento de varios trastornos, síndromes, enfermedades y afecciones, que incluyen aquellos mediados por la inhibición de la enzima ácido graso sintasa (FASN), tales como cáncer, obesidad y trastornos relacionados, y trastornos relacionados con el hígado. Reivindicación 1: Un compuesto de la fórmula (1) en donde R¹ y R² se toman junto con el átomo de carbono al que están ligados para formar una estructura de anillos opcionalmente sustituida seleccionada del grupo que consiste en (a) cicloalquilo C₃₋₈; en donde el cicloalquilo C₃₋₈ se sustituye opcionalmente con uno a dos grupos R¹¹; (b) cicloalquilo C₅₋₆ fusionado con benzo; en donde el cicloalquilo C₅₋₆ fusionado con benzo está ligado a través de un átomo de carbono de la porción de cicloalquilo C₅₋₆ de la estructura de anillos; en donde el cicloalquilo C₅₋₆ fusionado con benzo se sustituye opcionalmente con uno a dos grupos R¹¹; y (c) heterociclilo saturado de 4 a 8 miembros; en donde el heterociclilo saturado de 4 a 8 miembros contiene un heteroátomo seleccionado del grupo que consiste en O, S y N; en donde el S se sustituye opcionalmente con uno a dos oxo; en donde el N se sustituye con R¹⁰; siempre que el heteroátomo no esté presente en la posición 2 con relación al átomo de carbono de la imidazolin-5-ona; y en donde el heterociclilo saturado de 4 a 8 miembros se sustituye opcionalmente con un grupo R¹¹ y, además se sustituye opcionalmente con un grupo R¹²; en donde R¹⁰ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, -CH₂-(alquilo C₁₋₄ sustituido con hidroxilo), alquilo C₂₋₄-O-alquilo C₁₋₄, -(alquenilo C₂₋₄), -(alquil C₁₋₄)-fenilo, -C(O)-NRARB, -C(O)-(alquil C₁₋₃)-NRARB, -C(O)-(alquilo C₁₋₄), -C(O)-(alquilo C₁₋₂ fluorizado), -C(O)-(cicloalquilo C₃₋₆), -C(O)-fenilo, -C(O)-(heteroarilo de 5 a 6 miembros), un resto de fórmula (2) ó (3), -C(O)O-(alquilo C₁₋₄), -SO₂-(alquilo C₁₋₄), SO₂-NRARB, fenilo, y heteroarilo de 5 a 6 miembros; en donde Z¹ se selecciona del grupo que consiste en -CH₂-, -O-, -N(RC)-, -S-, -S(O)- y -SO₂-; en donde RA, RB y RC se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₄; y en donde el fenilo o heteroarilo de 5 a 6 miembros ya sea solo o como parte de un grupo sustituyente, se sustituye, además, opcionalmente con uno a dos sustituyentes independientemente seleccionados del grupo que consiste en halógeno, hidroxilo, ciano, NRARB, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, alcoxi C₁₋₄, y alcoxi C₁₋₄ fluorizado; en donde cada R¹¹ se selecciona independientemente del grupo que consiste en hidroxi, oxo, halógeno, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, alcoxi C₁₋₄, alcoxi C₁₋₄ fluorizado, alquilo C₁₋₄ sustituido con hidroxi, -(alquilo C₁₋₄)-O-(alquilo C₁₋₄), -(alquilo C₁₋₄)-fenilo, -ciano, -NRDRE, -C(O)-NRDRE, -C(O)-(alquilo C₁₋₄), -C(O)-fenilo, -C(O)-(heteroarilo de 5 a 6 miembros), un resto de fórmula (2) ó (4), -C(O)OH, -C(O)O-(alquilo C₁₋₄), -SO₂-(alquilo C₁₋₄), SO₂-NRDRE, fenilo y heteroarilo de 5 a 6 miembros; en donde Z² se selecciona del grupo que consiste en -CH₂-, -O-, -N(RC)-, -S-, -S(O)- y -SO₂-; en donde RD, RE y RF se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₄; y en donde el fenilo o heteroarilo de 5 a 6 miembros ya sea solo o como parte de un grupo sustituyente, se sustituye, además, opcionalmente con uno a dos sustituyentes independientemente seleccionados del grupo que consiste en halógeno, hidroxi, ciano, NRDRE, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, alcoxi C₁₋₄ y alcoxi C₁₋₄ fluorizado; y en donde R¹² se selecciona del grupo que consiste en hidroxi, oxo, halógeno, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, alcoxi C₁₋₄, alcoxi C₁₋₄ fluorizado, y alquilo C₁₋₄ sustituido con hidroxi; m es un entero de 0 a 1; y n es un entero de 0 a 2; siempre que, cuando n es 2, entonces m es 1; el resto de fórmula (5) selecciona del grupo que consiste en azetidin-3-ilo, pirrolidin-3-ilo, pirrolidin-3R-ilo, pirrolidin-3S-ilo, piperidin-3-ilo, piperidin-3R-ilo, piperidin-2S-ilo, y piperidin-4-ilo; a es un entero de 0 a 1; L¹ se selecciona del grupo que consiste en -C(O)-, -C(O)O-, -C(O)-NRL-, -C(S)-, -SO₂-, y -SO₂-NRL; en donde RL se selecciona de grupo que consiste en hidrógeno y alquilo C₁₋₄; R³ se selecciona del grupo que consiste en alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, alquilo C₁₋₄ sustituido con hidroxi, alquenilo C₂₋₄, cicloalquilo C₃₋₆, -(alquilo C₁₋₄)-(cicloalquilo C₃₋₆), heterociclilo saturado de 4 a 6 miembros, -(alquilo C₁₋₄)-(heterociclilo saturado de 4 a 6 miembros), -(alquenilo C₂₋₄)-(heterociclilo saturado de 5 a 6 miembros), heteroarilo de 5 a 6 miembros, -(alquilo C₁₋₄)-(heteroarilo de 5 a 6 miembros), -(alquenilo C₂₋₄)-(heteroarilo de 5 a 6 miembros), y NRVRW; en donde RV y RW se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₄; en donde cicloalquilo C₃₋₆, heterociclilo saturado de 4 a 6 miembros o heteroarilo de 5 a 6 miembros, ya sea solo o como parte de un grupo sustituyente, se sustituyen opcionalmente con uno a dos sustituyentes independientemente seleccionados del grupo que consiste en halógeno, hidroxilo, ciano, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, -(alquilo C₁₋₄)-OH, alcoxi C₁₋₄, alcoxi C₁₋₄ fluorizado, y NRGRH; en donde RG y RH se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₄; el resto de fórmula (6) se selecciona del grupo que consiste en el grupo de formulas (7); b es un entero de 0 a 2; cada R⁴ se selecciona independientemente del grupo que consiste en hidroxi, halógeno, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, alcoxi C₁₋₄, alcoxi C₁₋₄ fluorizado, ciano, y NRJRK; en donde RJ y RK se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₄; siempre que cada grupo R⁴ esté ligado a un átomo de carbono; siempre que, cuando el resto de fórmula (6) se selecciona del grupo que consiste en el grupo de formulas (8), y esté sustituido con -(R⁴)ᵇ, entonces b es un entero de 0 a 1; R⁵ se selecciona del grupo que consiste en (a) el compuesto de formula (9)y (b) el compuesto de fórmula (10); en donde el anillo A¹ se selecciona del grupo que consiste en arilo, heteroarilo y heterociclilo parcialmente insaturado; c es un entero de 0 a 2; cada R⁶ se selecciona independientemente del grupo que consiste en hidroxi, oxo, halógeno, ciano, nitro, alquilo C₁₋₄, alquilo C₁₋₄ fluorizado, alquilo C₁₋₄ sustituido con hidroxi, -(alquilo C₁₋₄)-CN, -(alquilo C₁₋₄)-O-(alquilo C₁₋₄, alcoxi C₁₋₄, alcoxi C₁₋₄ fluorizado, -SO₂-(alquilo C₁₋₄), -NRMRN, -(alquilo C₁₋₄)-NRPRQ, -C(O)-(alquilo C₁₋₄), -C(O)-(alquilo C₁₋₂ fluorizado), -C(O)-NRMRN, -C(O)OH, -C(O)O-(alquilo C₁₋₄), -NRM-C(O)H, -NRM-C(O)-(alquilo C₁₋₄), -NRM-SO₂-(alquilo C₁₋₄), cicloalquilo C₃₋₆, -ciano-(cicloalquilo C₃₋₆), -(alquilo C₁₋₄)-(cicloalquilo C₃₋₆), -S-(cicloalquilo C₃₋₆), -SO-(cicloalquilo C₃₋₆), -SO₂-(cicloalquilo C₃₋₆), -NH-(cicloalquilo C₃₋₆), -NH-SO₂-(cicloalquilo C₃₋₆), oxetanilo, -(alquilo C₁₋₂)-oxetanilo, tetrahidrofuranilo, -(alquilo C₁₋₂)-tetrahidro-furanilo, tetrahidropiranilo, y -(alquilo C₁₋₂)-tetrahidro-piranilo; en donde RM y RN se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₄; en donde RP y RQ se seleccionan independientemente del grupo que consiste en hidrógeno y alquilo C₁₋₄; alternativamente RP y RQ se toman junto con el átomo de nitrógeno al que están ligados para formar un heterociclilo saturado de 5 a 6 miembros; tal heterociclilo saturado de 5 a 6 miembros se sustituye opcionalmente con un sustituyente seleccionado del grupo que consiste en halógeno, alquilo C₁₋₄, y alquilo C₁₋₄ fluorizado; en donde el anillo A² se selecciona
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US20170119786A1 (en) * | 2011-03-08 | 2017-05-04 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
WO2014039769A1 (en) * | 2012-09-07 | 2014-03-13 | Janssen Pharmaceutica Nv | Imidazolin-5-one derivatives useful as fatty acid snthase (fasn) inhibitors for|the treatment of cancer |
EP3083600B1 (en) * | 2013-12-17 | 2018-09-26 | Janssen Pharmaceutica NV | Imidazolin-5-one derivatives useful as fasn inhibitors for the treatment of cancer |
WO2016079317A1 (en) | 2014-11-20 | 2016-05-26 | Vib Vzw | Means and methods for treatment of early-onset parkinson's disease |
MX2017016370A (es) | 2015-06-18 | 2018-04-11 | Cephalon Inc | Derivados de 4-bencil y 4-benzoil piperidina sustituidos. |
AU2016280255A1 (en) | 2015-06-18 | 2018-02-08 | Cephalon, Inc. | 1, 4-substituted piperidine derivatives |
JP2019533714A (ja) * | 2016-11-11 | 2019-11-21 | 3−ブイ・バイオサイエンシーズ・インコーポレイテッド3−V Biosciences,Inc. | 脂質合成の複素環式モジュレーター |
TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
US10902613B2 (en) | 2019-03-20 | 2021-01-26 | Bi Incorporated | Systems and methods for textural zone identification |
US10692345B1 (en) | 2019-03-20 | 2020-06-23 | Bi Incorporated | Systems and methods for textural zone monitoring |
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BRPI0312649A2 (pt) * | 2002-07-09 | 2017-05-16 | Fasgen Llc | compostos, composições farmacêuticas contendo os mesmos, e processos de uso para os mesmos. |
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2013
- 2013-09-06 WO PCT/US2013/058416 patent/WO2014039769A1/en active Application Filing
- 2013-09-06 US US14/020,122 patent/US20150099730A1/en not_active Abandoned
- 2013-09-06 JP JP2015531220A patent/JP6285442B2/ja not_active Expired - Fee Related
- 2013-09-06 CA CA2884355A patent/CA2884355C/en not_active Expired - Fee Related
- 2013-09-06 EP EP13762696.6A patent/EP2892892B1/en active Active
- 2013-09-09 AR ARP130103205A patent/AR092491A1/es unknown
-
2015
- 2015-09-11 US US14/851,738 patent/US10077261B2/en active Active
-
2018
- 2018-07-19 US US16/040,004 patent/US20180327401A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CA2884355C (en) | 2022-05-17 |
US20150099730A1 (en) | 2015-04-09 |
WO2014039769A1 (en) | 2014-03-13 |
US10077261B2 (en) | 2018-09-18 |
US20160002219A1 (en) | 2016-01-07 |
US20180327401A1 (en) | 2018-11-15 |
EP2892892B1 (en) | 2017-05-31 |
EP2892892A1 (en) | 2015-07-15 |
JP2015527397A (ja) | 2015-09-17 |
CA2884355A1 (en) | 2014-03-13 |
JP6285442B2 (ja) | 2018-02-28 |
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