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AR071909A1 - Compuesto triazina, composicion que lo comprende y metodo para elaborar el compuesto - Google Patents

Compuesto triazina, composicion que lo comprende y metodo para elaborar el compuesto

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Publication number
AR071909A1
AR071909A1 ARP090101879A ARP090101879A AR071909A1 AR 071909 A1 AR071909 A1 AR 071909A1 AR P090101879 A ARP090101879 A AR P090101879A AR P090101879 A ARP090101879 A AR P090101879A AR 071909 A1 AR071909 A1 AR 071909A1
Authority
AR
Argentina
Prior art keywords
alkyl
optionally substituted
heterocyclyl
amino
membered
Prior art date
Application number
ARP090101879A
Other languages
English (en)
Inventor
Arie Zask
Aranapakam Venkatesan
Santos Osvaldo Dos
Zecheng Chen
Christoph Dehnardt
Jeroen C Verheijen
Tarek S Mansour
Semiramis Ayral-Kaloustian
Joshua Aaron Kaplan
Kevin J Curran
Santos Efren Guillermo Delos
David J Richard
Ariamala Gopalsamy
Mengxiao Shi
Original Assignee
Wyeth 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.)
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Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40911929&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR071909(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Wyeth Corp filed Critical Wyeth Corp
Publication of AR071909A1 publication Critical patent/AR071909A1/es

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    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
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    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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Abstract

Estos compuestos inhiben la quinasa PI3 y mTOR, y se pueden utilizar para tratar enfermedades mediadas por quinasa PI3 e y mTOR, tal como una variedad de c nceres. Se describen metodos para elaborar y utilizar los compuestos de esta solicitud. Tambien se describen aqu¡ varias composiciones que contienen los compuestos de esta solicitud. Reivindicacion 1: Un compuesto de la formula 1 caracterizado porque R1 es como en formulas (2) o (3) en donde R6, R7, R8, R9 se seleccionan cada uno independientemente del grupo que consiste de un  tomo de hidrogeno, y un alquilo C1-6 opcionalmente sustituido con alquenilo C2-6, alcadienilo C4-6, alquinilo C2-6 o alcadinilo C4-6; y uno de R6 y R9, R6 y R8, o R7 y R8 se adhieren por un grupo de ligado (CH2)y, (CH2-X-), o (CH2-X-CH2) en donde uno o dos  tomos de hidrogeno en el grupo de ligado se pueden reemplazar independientemente por alquilo C1-6, (alquilo C1-6)NH-, (alquilo C1-6)2N-, (arilo C6-14)alquil-O-, halo, heterociclilo C1-9 de 3-10 miembros opcionalmente sustituido con alquilo C1-6-, HO-, o H2N-; en donde dos  tomos de hidrogeno cualesquiera en el mismo  tomo de carbono del grupo ligado se puede reemplazar por un  tomo de ox¡geno para formar un sustituyente oxo (=O), y es 1, 2 o 3; X es O, S(O)n, o NR10; n es 0, 1 o 2; la l¡nea intermitente ------ representa un segundo enlace opcional; R10 se selecciona del grupo que consiste de H, alquilo C1-6, -SO2(alquilo C1-6), -COO(alquilo C1-6), -CONH(alquilo C1-6), -CON(alquilo C1-6)2, -CO(alquilo C1-6), y -SO2NHR11; R11 se selecciona del grupo que consiste de H, alquilo C1-6 opcionalmente sustituido con OH, NR11R11 o un heterociclilo C1-6 de 3-7 miembros, -CO(alquilo C1- 6), arilo C6-10 opcionalmente sustituido, y heteroarilo C1-9 opcionalmente sustituido; R2 es arilo C6-14 opcionalmente sustituido-NH-COR3, heteroarilo C1-9 opcionalmente sustituido-NH-COR3, -CH=CH-arilo C6-10-NH-COR3 o -CH=CH-heteroarilo C1-9-NH-COR3; R3 es OR5, NR5R5 o NHR5; R5 se selecciona independientemente del grupo que consiste de alquilo C1-6, alquenilo C3-6, alquinilo C3-6, arilo C6-10 opcionalmente sustituido, haloalquilo C1-6, heteroarilo C1-9 opcionalmente sustituido, hidroxialquilo C1-6, cicloalquilo C3-10 mono o bic¡clico saturado no saturado C3-10 opcionalmente sustituido con OH, NR11R11 o heterociclilo C1-6 de 3-7 miembros, y heterociclilo C1-9 mono o bic¡clico saturado o insaturado de 3-10 miembros; con la condicion que se saturan los anillos heterociclilo y cicloalquilo de tres miembros; o dos grupos R5 tomados juntos con el  tomo de nitrogeno al cual ellos se adhieren para formar un sistema de anillo de 3 a 8 miembros opcionalmente sustituido con alquilo C1-6, cuyo sistema de anillo se satura o no se satura y tiene, en adicion a dicho  tomo de nitrogeno, miembros de anillo de 0 a 2 hetero tomos seleccionados de O, S, S(O), S(O)2 y NR10; R4 se selecciona del grupo que consiste de: a) alquilo C1-6 opcionalmente sustituido con: i) heterociclilo C1-9 de 3-10 miembros opcionalmente sustituido con alquilo C1-6-, ii) H2N-, iii) (alquilo C1-6)NH-, iv) (alquilo C1-6)2N-, v) NH(CH2)aN(alquilo C1-6)2 en donde a es 2, 3 o 4, y vi) CHO, b) alquenilo C3-6, c) alquinilo C3-6, d) -O-alquilo C1-8 opcionalmente sustituido con -O-alquilo C1-8, e) -O-alquenilo C3-8, f) -O-alquinilo C3-8, g) cicloalquilo C3-8 mono o bic¡clico saturado o no saturado, y h) -O-cicloalquilo C3-12 mono o bic¡clico saturado o no saturado, todos los anteriores opcionalmente sustituido con OH, NR11R11 o un heterociclilo C1-6 de 3-7 miembros opcionalmente sustituido con alquilo C1-6-, dado que un OH o NR11R11 no se une directamente en un  tomo de carbono que se une doble o triple a otro  tomo de carbono; i) -CH=CH-arilo C6-10, j) -CH=CH-heteroarilo C1-9, k) arilo C6-10 opcionalmente sustituido; l) heteroarilo C1-9 de 5- 10 miembros opcionalmente sustituido adherido al grupo funcional triazina por v¡a del  tomo de carbono; m) heterociclilo C1-9 mono o bic¡clico saturado o insaturado de 3-10 miembros adherido al grupo funcional triazina a traves de un  tomo de nitrogeno o carbono y opcionalmente sustituido con de 1 a 3 sustituyentes seleccionados independientemente de: OH, NR11R11, alquilo C1-6, (alquilo C1-6)amido-, (alquilo C1-6)C(O)-, (alcoxi C1-6)carbonil-, adamantilo, hidroxialquilo C1-6, o un heterociclilo C1-6 de 3-7 miembros, con la condicion que el heterociclilo de 3 miembros se satura y se adhiere al grupo funcional triazina a traves de un  tomo de nitrogeno, y el heterociclilo bic¡clico de 5 miembros se satura; n) -O-arilo C6-10 opcionalmente sustituido; o) -O-heteroarilo C1-9 opcionalmente sustituido; p) -O- (mono o bic¡clico saturado o insaturado de 3-12 miembros)heterociclilo C1-9 opcionalmente sustituido con (alcoxi C1-6)carbonil-, H2NS(O)2-, o alquilo C1-6 adicionalmente opcionalmente sustituido con OH, NR11R11 o un heterociclilo C1-6 de 3-7 miembros1 con la condicion que se satura el heterociclilo de tres miembros; q) - NHarilo C6-10, r) -NHheteroarilo C1-9, s) -NHNH2, t) -NHNHalquilo C1-6, u) -NHN(alquilo C1-6)2, v) -NHOH, w) -COOH, x) -COO-alquilo C1-6, y) -CONR12R13, z) -NR12R13, los grupos de formulas (4) en donde Z es Ch2, O, S(O)n o NR10; ee) halogeno, ff) arilo C6-14-S(O)2-NH-, gg) R11NHC(O)NH-O-, y hh) heteroarilo C1-4 monociclico de 5 miembros opcionalmente sustituido adherido al grupo funcional triazina por v¡a de un  tomo de nitrogeno; R12 y R13 se seleccionan cada uno independientemente de H, alquilo C1-8 opcionalmente mono o disustituido, alquenilo C3-8 opcionalmente sustituido, y alquinilo C3-8 opcionalmente sustituido, los sustituyentes opcionales se seleccionan de alcoxi C1-6, OH, NR11R11, y heterociclilo C1-6 de 3-7 miembros, dado que un OH o NR11R11 no se une directamente en un  tomo de carbono que se une doble o triple a otro  tomo de carbono; o R12 y R13 tomados junto con el  tomo de nitrogeno al cual ellos se adhieren forman un sistema de anillo de 3 a 8 miembros opcionalmente sustituido con alquilo C1-6, cuyo sistema de anillo se satura o no se satura y tiene, en adicion a dicho  tomo de nitrogeno, miembros de anillo de 0 a 2 hetero tomos seleccionados de O, S(O)n y NR10; o R12 y R13 tomados junto con el  tomo de nitrogeno al cual ellos se adhieren forman los compuestos de formulas (5) en donde a y b son cada uno independientemente -CH2-, O, S, o NR10, y x es 1-3; heteroarilo C1-9 se refiere a un sistema de anillo arom tico de 5-10 miembros que tiene uno o m s anillos y 1; 2; 3 o 4 miembros de anillo seleccionados independientemente de O, NR10 y S(O)n, heterociclilo C1-9 se refiere a un sistema de anillo de 3-10 miembros que tiene uno o m s anillos y 1; 2; 3 o 4 miembros de anillo seleccionados independientemente de O, NR10 y S(O)n, y los grupos arilo y heteroarilo opcionalmente sustituidos se sustituyen o no se sustituyen con 1 o 2 grupos funcionales seleccionados del grupo que consiste de: a) alquilo C1-6 opcionalmente sustituido con OH, NH2, NH(alquilo C1-6), N(alquilo C1-6)2, -NH(CH2)wN(alquilo C1-6)2 en donde w es 2, 3 o 4, o heterociclilo C1-9 de 3-10 miembros opcionalmente sustituido con 1 a 3 sustituyentes alquilo C1-6 seleccionados independientemente; b) halogeno; c) hidroxi; d) NH2, e) NO2, f) SO2NH2, g) COOH; h) COO(alquilo C1-6); i) NHCOO(alquilo C1-6); j) NH(alquilo C1-6); k) N(alquilo C1-6)2, l) C(O)NRaRb, en donde Ra es H o alquilo C1-6, y Rb es H, alquilo C1-6, (arilo C6-14)alquil-, o (heteroarilo C1-9)alquil-; m) -Y-Q, en donde Y es: i) O, ii) NH, iii) N(alquilo C1-6), iv) NHSO2, v) SO2NH, vi) NHCONH, vii) NHCON(alquilo C1-6), viii) S(O)q, q es 0, 1 o 2, ix) -C(O)NH-, x) -C(O)N(CH3)-, xi) -NHC(O)-, xii) C(O), o xiii) ausente, y Q se selecciona de: i) arilo C6-10, opcionalmente sustituido con de 1 a 3 sustituyentes seleccionados independientemente de: A) alcoxi C1-6 opcionalmente sustituido con 1) H2N-, 2) (alquilo C1-6)amino-, 3) di(alquilo C1-6)amino-, 4) heterociclilo C1-9- opcionalmente sustituido por alquilo C1-6-, o 5) hidroxilo, B) (alcoxi C1-6)carbonil-, C) (alcoxi C1-6)C(O)NH-, D) alquilo C1-6- opcionalmente sustituido con 1) H2N-, 2) (alquilo C1-6)amino-, o 3) di(alquilo C1-6)amino-, E) (alquilo C1-6)amino-, F) di(alquilo C1-6)amino-, G) (alquilo C1-6)amido- opcionalmente sustituido con 1) H2N-, 2) (alquilo C1-6)amino-, o 3) di(alquilo C1-6)amino-, H) (alquilo C1-6)carboxiamido-, I) heterociclilo C1-9- opcionalmente sustituido por alquilo C1-6- o hidroxialquilo C1-6-, J) heterociclilo(alquilo C1-6)- opcionalmente sustituido por alquilo C1-6,K) halogeno, L) hidroxilo, M) hidroxialquilo C1-6-, N) perfluoro(C1-6)alquil-, O) H2N-, P) ON-, Q) H2NSO2 R) HO2C-, y S) NC-, ii) heteroarilo C1-9 de 5-10 miembros, opcionalmente sustituido con de 1 a 3 sustituyentes seleccionados independientemente de: A) alcoxi C1-6- opcionalmente sustituido con 1) H2N-, 2) (alquilo C1-6)amino-, 3) di(alquilo C1-6)amino-, 4) heterociclilo C1-9- opcionalmente sustituido por alquilo C1-6-, o 5) hidroxilo, B) (alcoxi C1-6)carbonil-, C) (alcoxi C1-6)C(O)NH-, D) alquilo C1-6- opcionalmente sustituido con 1) H2N-, 2) (alquilo C1-6)amino-, o 3) di(alquilo C1-6)amino-, E) (alquilo C1-6)amino-, F) di(alquilo C1-6)amino-, G) (alquilo C1-6)amido- opcionalmente sustituido con 1) H2N-, 2) (alquilo C1-6)amino-, o 3) di(alquilo C1-6)amino-, H) (alquilo C1-6)carboxiamido-, I) heterociclilo C1-9- opcionalmente sustituido por alquilo C1-6- o hidroxialquilo C1-6, J) heterociclilo(alquilo C1-6)- opcionalmente sustituido por alquilo C1-6-, K) halogeno, L) hidroxilo, M) hidroxialquilo C1-6-, N) perfluoro(C1-6)alquil-, O) H2N-, P) O2N-, Q) H2NSO2, R) HO2C-, y S) NC-, iii) heterociclilo C1-9 de 3-10 miembros, opcionalmente sustituido con de 1 a 3 sustituyentes seleccionados independientemente de: A) alquilo C1-6-, B) heterociclilo(alquilo C1-6)-, C) (arilo C6-14)alquil-, D) acilo C1-8-, E) (alcoxi C1-6)carbonil-, F) (alquilo C1-6)carboxil- , G) halogeno, H) haloalquilo C1-6-, I) hidroxilo, J) hidroxialquilo C1-6, K) H2N-, L) (alquilo C1-6)amino-, M) di(alquilo C1-6)amino-, N) H
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