AR070525A1 - Imidazolidin -2,4- dionas sustituidas con heterociclos , un proceso para su preparacion , medicamentos que las comprenden y su uso - Google Patents

Imidazolidin -2,4- dionas sustituidas con heterociclos , un proceso para su preparacion , medicamentos que las comprenden y su uso

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AR070525A1
AR070525A1 ARP090100402A ARP090100402A AR070525A1 AR 070525 A1 AR070525 A1 AR 070525A1 AR P090100402 A ARP090100402 A AR P090100402A AR P090100402 A ARP090100402 A AR P090100402A AR 070525 A1 AR070525 A1 AR 070525A1
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alkyl
cycloalkyl
aryl
substituted
heteroaryl
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Sanofi Aventis
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    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
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    • 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
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    • 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
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    • 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

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Abstract

Los compuestos son adecuados, por ejemplo como fármacos antiobesidad. Reivindicacion 1: Un compuesto de formula (1) en la que R, R' son cada uno, independientemente, H, (CH2)n-arilo, o alquilo C1-6, en que el radical alquilo C1-6 o arilo puede estar sustituido con halogeno, OR14, S(O)mR12 o NR13R15; o R y R' juntos forman un anillo que tiene de tres a ocho átomos de carbono, en que un átomo de carbono puede estar reemplazado por O, S(O)m, NR13 o NR15; m es 0, 1, 2; n es 0, 1, 2, 3, 4; p es 1, 2, 3, 4, 5; q es 1, 2, 3, 4; r es 2, 3, 4, 5, 6: v es 0, 1, 2, 3, 4; A, D, E, G, L son cada uno independientemente, C o N, en los que, cuando se definen como N el correspondiente sustituyente R1, R2, R3, R4, R5 está ausente, o R2-D=E-R3 o R4-G=L-R5 se definen como S u O y donde el anillo de cinco miembros o de seis miembros puede estar condensado con -(CH2)3- o -(CH2)4- o -CH=CH-CH=CH- para formar un sistema bicíclico; R1, R2, R3, R4, R5 son cada uno independientemente, H, F, CI, Br, I, CN, N3, NC, NO2, CF3, alquilo C1-8, cicloalquilo C3-8, (CH2)q-[cicloalquilo C3-8], (CH2)n-[cicloalquenilo C3-8], (CH2)n-[bicicloalquilo C7-12], (CH2)n-[tricicloalquilo C7-12], adamantan-1-ilo, adamantan-2-ilo, (CH2)n-arilo, (CH2)n-heteroarilo, OCF3, O-R11, NR13R15, NH-CN, S(O)m-R12, SO2-NH2, SO2-N=CHN(CH3)2, SO2-NH-[alquilo C1-8], SO2-NH-[cicloalquilo C3-8], SO2-NH-(CH2)n-arilo, SO2-NH-(CH2)n-heteroarilo, SO2-N[alquilo C1-8]2, SO2-R16, SF5, CO-O[alquilo C1-8], CO-O[cicloalquilo C3-8], CO-O-(CH2)n-arilo, CO-O-(CH2)n-heteroarilo, CONH2, CO-NH-CN, CO-NH-[alquilo C1-8], CO-N[alquilo C1-8]2, CO-NH-[cicloalquilo C3-8], CO-N[cicloalquilo C3-8]2, C(=NH)-O-[alquilo C1-6], C(=NH)-NH2, C(=NH)R16, C(=NR13)NR12R13, (CH2)n-C(=NSO2-R12)NH2, CO-R16, COOH, CO-alquilo C1-8, CO-cicloalquilo C3-8, CO-arilo, CO-heteroarilo, CH(OH)-arilo, CH(OH)-heteroarilo, CH[O-alquil C1-6]-arilo, CH[O-alquil C1-6]-heteroarilo, CHF-arilo, CHF-heteroarilo, CF2-arilo, CF2-heteroarilo, CHO, CH2-OH, CH2-CN, CH2-OR12, CH2-O-(CH2)n-CO-O[alquilo C1-8], CH2-O-(CH2)n-CO-NH2, CH2-O-(CH2)q-COOH, en los que los radicales alquilo, cicloalquilo, cicloalquenilo, bicicloalquilo, bicicloalquenilo y tricicloalquilo pueden estar sustituidos con átomos de fluor y en donde los radicales arilo o heteroarilo pueden estar sustituidos con halogeno, CN, alquilo C1-6, cicloalquilo C3-6, O-alquilo C1-6, OCF3, OH, (CH2)n-arilo, O-(CH2)n-arilo, S(O)m-alquilo C1-6, SO2-NH2, SH, NR12R13, NH-CO-[alquilo C1-6], NH-CO-(CH2)n-arilo, (CH2)n-COOH, (CH2)n-CONH2, (CH2)n-CO-O-alquilo C1-6, o (CH2)n-CO-alquilo C1-6 y en los que los radicales alquilo pueden estar sustituidos con átomos de fluor; R6, R7, R8, R9, R10 son cada uno independientemente, R11, T-heterociclo bicíclico-U-R40, T-aril-U-R40 o T-heteroaril-U-R40, en los que el heterociclo bicíclico o el radical arilo o heteroarilo puede estar condensado a un anillo de carbono aromático o no aromático de 5 o 6 miembros, en el que uno o más grupos CH o CH2 pueden reemplazarse por átomos de oxígeno y en el que el anillo de carbono aromático o no aromático de 5 o 6 miembros puede estar sustituido con F, =O o alquilo C1-6 y en el que el heterociclo bicíclico puede contener de 9 a 12 miembros de anillo y hasta cinco grupos CH o CH2 pueden estar reemplazados independientemente por N, NR20, O, S(O)m o C=O y en los que el radical arilo o heteroarilo o el heterociclo bicíclico puede no estar sustituido o puede estar mono o polisustituido con R11, F, CI, Br, I, CN, N3, NC, NO2, CF3, (CH2)n-O-R11, O-R13, OCF3, (CH2)n-NH-R11, (CH2)n-N[(CH2)q-CO-O-alquilo C1-6]2, (CH2)n-N[(CH2)q-COOH]2, (CH2)n-N[(CH2)q-CONH2]2, (CH2)n-NH-R13, (CH2)n-N(R13)2, (CH2)n-NH-SO2-R16, (CH2)n-NH-(CH2)n-SO2-R12, (CH2)n-NR12-CO-R16, (CH2)n-NR12-CO-NR12R13, (CH2)n-NR12-CO-N(R12)2, (CH2)n-NH-C(=NH)-NH2, (CH2)n-NH-C(=NH)-R16, (CH2)n-NH-C(=NH)-NHR12, (CH2)n-NH-(CH2)n-CO-NH-[alquilo C1-8], (CH2)n-NH-(CH2)n-CO-N[alquilo C1-8]2, (CH2)n-NH-(CH2)n-CO-NH-[cicloalquilo C3-8], (CH2)n-NH-(CH2)n-CO-N[cicloalquilo C3-8]2, (CH2)n-NH-C(CH3)2-CO-O-alquilo C1-8, (CH2)n-NH-C(CH3)2-CO-O-cicloalquilo C3-8, (CH2)n-NH-C(CH3)2-CO-O-(CH2)n-arilo, (CH2)n-NH-C(CH3)2-CO-O-(CH2)n-heteroarilo, (CH2)n-NH-C(CH3)2-CO-NH2, (CH2)n-NH-C(CH3)2-CO-NH-[alquilo C1-8], (CH2)n-NH-C(CH3)2-CO-N[alquilo C1-8]2, (CH2)n-NH-(CH3)2-CO-NH-[cicloalquilo C3-8], (CH2)n-NH-C(CH3)2-CO-N[cicloalquilo C3-8]2, (CH2)n-NH-C(CH3)2-COOH, (CH2)n-S(O)m-R18, S(O)mR12, SO2R16, SO2-N=CH-N(CH3)2, el resto formula (2), SO2-NH-COR12, SO2-NHR12, SO2-N[alquilo C1-8]2, SF5, COOH, CO-NH2, (CH2)q-CN, (CH2)n-CO-NH-CN, (CH2)n-CO-NH-piperidin-1-ilo, (CH2)n-CO-NH-SO2-NHR12, (CH2)N-CO-NH-SO2-R18, (CH2)n-CHO, (CH2)n-C(=NH)-NH2, (CH2)n-C(=NH)-NHOH, (CH2)n-C(=NH)-[NH-O-alquilo C1-6], (CH2)n-C(=NH)(R16), (CH2)n-C(=NR13)-NHR12, (CH2)n-C(=NR12)-NR12R13, (CH2)n-C(=NSO2-R12)-NH2, o (CH2)n-C(=NH)O[alquilo C1-6], en los que los radicales alquilo y cicloalquilo pueden estar sustituidos con átomos de fluor y en los que los radicales arilo o heteroarilo pueden estar sustituidos con halogeno, CN, CF3, alquilo C1-6, cicloalquilo C3-6, O-alquilo C1-6, OCF3, OH, SH, S(O)m-alquilo C1-6, SO2-NH2, NR12R13, NH-CO-[alquilo C1-6], NH-CO-(CH2)n-arilo, (CH2)n-COOH, (CH2)n-CONH2, (CH2)n-COO-alquilo C1-6, (CH2)n-CO-alquilo C1-6, y en los que los radicales alquilo pueden estar sustituidos con átomos de fluor, F, CI, Br, I, CN, N3, NC, NO2, CF3, (CH2)n-O-R11, (CH2)n-O-(CH2)n-CO-O-(CH2)n-NH2, O-R13, OCF3, (CH2)n-NH-R11, (CH2)n-NH-R13, (CH2)n-NH-SO2-R16, (CH2)n-NH-(CH2)n-SO2-R12, (CH2)n-NR12-CO-N(R12)2, (CH2)n-NH-C(=NH)-R16, (CH2)n-NH-C(=NH)-NHR12, (CH2)n-NR12-C(=NR13)-NHR12, (CH2)n-NR12-C(=NR12)-NR12R13, (CH2)n-NH-(CH2)n-CO-NH-[alquilo C1-8], (CH2)n-NH-(CH2)n-CO-N[alquilo C1-8]2, (CH2)n-NH-(CH2)n-CO-NH-[cicloalquilo C3-8], (CH2)n-NH-(CH2)n-CO-N[cicloalquilo C3-8]2, S(O)mR12, SO2R16, SO2-N=CH-N(CH3)2, el resto de formula (2), SO2-NHR12, SO2-N[alquilo C1-8]2, SF5, COOH, CO-NH2, (CH2)q-CN, (CH2)n-CHO, (CH2)n-C(=NH)-NHOH, (CH2)n-C(=NH)(R16), (CH2)n-C(=NR13)-NHR12, (CH2)n-C(=NR12)-NR12R13, (CH2)n-C(=NH)O[alquilo C1-6], en los que los radicales alquilo y cicloalquilo pueden estar sustituidos con átomos de fluor y donde los radicales arilo o heteroarilo pueden estar sustituidos con halogeno, CN, alquilo C1-6, cicloalquilo C3-6, O-alquilo C1-6, OCF3, SH, S(O)m-alquilo C1-6, SO2-NH2, NR12R13, NH-CO-alquilo C1-6, NH-CO-(CH2)n-arilo, (CH2)n-COOH, (CH2)n-CONH2, (CH2)n-CO-[O-alquilo C1-6], (CH2)n-CO-alquilo C1-6, y en los que los radicales alquilo pueden estar sustituidos con átomos de fluor; en los que al menos uno de los radicales R6, R7, R8, R9 y R10 siempre se define como T-heterociclo bicíclico-U-R40, T-aril-U-R40 o T-heteroaril-U-R40; y en los que una de las cuatro parejas de radicales de R6 y R7, o R7 y R8, o R8 y R9, o R9 y R10 pueden formar juntas, en cada caso, los grupos -CH2-CH2-CH2- o -CH2-CH2-CH2-CH2- en los que hasta dos grupos -CH2- se pueden reemplazar por -O- y en donde los grupos -CH2-CH2-CH2- o -CH2-CH2-CH2-CH2- pueden estar sustituidos con F, alquilo C1-8 o =O; T es NR17, O, S(O)m, C(Q1Q2), CO, NR23-CO-NR24, NR23-SO2-NR24, SO2-NR23-SO2, CO-NR23-CO, NR23-C(=NR13)-NR24, NR23-C(=NR22)-NR24, CO-NR23-CR22R23, NR23-SO2-CR22R24, CR22R24-CO-NR23, CR22R23-NR23-SO2, SO2-CR22R23-NR23, SO2-NR23-CR22R23, NR23-CR22R23-SO2, CR23R24-CR23R24-CR23R24 ; U es un enlace, (CH2)n-C(Q1Q2), (CH2)n-O, O-alquilo C1-6, (CH2)n-S(O)m, S(O)m-alquilo C1-6, (CH2)n-NR23, NR23-alquilo C1-6; R40 es un heterociclo, un heterociclo bicíclico o un heterociclo tricíclico, en los que el radical heterocíclico, el radical heterocíclico bicíclico, el radical heterocíclico tricíclico puede estar sustituido con halogeno, CN, CF3, alquilo C1-6, cicloalquilo C3-6, O-alquilo C1-6, OCF3, OH, SH, S(O)m-alquilo C1-6, S(O)m-cicloalquilo C3-6, SO2-NH2, SO3H, S(O)m-R18, NR12R13, NH-CO-[alquilo C1-6], NH-CO-(CH2)n-arilo, (CH2)n-COOH, (CH2)n-CONH2, (CH2)n-COO-alquilo C1-6, (CH2)n-CO-alquilo C1-6, (CH2)n-C(=NR13)NHR12, (CH2)n-C(=NSO2-R12)NH2 o (CH2)n-NR12-C(=NR12)-NR12R13, en la que R40 es un azucar cíclico no sustituido o sustituido, o un ácido de azucar cíclico no sustituido o sustituido; Q1 y Q2 son cada uno independientemente H, alquilo C1-6, F, OH, OR12, O-CO-OR12, O-CO-R12, NH2, NHR12, NHR13, N(R12)2, NHCOR12, o Q1 y Q2 junto con el átomo de carbono al cual están unidos, forman un carbociclo que tiene de 3 a 8 átomos de carbono; R11 es H, alquilo C1-8, alquenilo C2-10, alquinilo C2-10, cicloalquilo C3-8, (CH2)q-[cicloalquilo C3-8], (CH2)n-arilo , (CH2)n-CO-[O-alquilo C1-8], (CH2)n-CO-[O-cicloalquilo C3-8], (CH2)n-CO-[alquilo C1-8], (CH2)n-CO-[cicloalquilo C3-8], (CH2)n-CO-arilo, (CH2)n-CO-heteroarilo, (CH2)q-CO-NH2, (CH2)q-COOH, (CH2)n-P(O)(OH)[O-alquilo C1-6], (CH2)n-P(O)[O-alquilo C1-6]2, (CH2)n-P(O)(OH)(O-CH2-arilo), (CH2)n-P(O)(O-CH2-arilo)2, (CH2)n-P(O)(OH)2, (CH2)n-SO3H, (CH2)n-SO2-NH2, (CH2)n-CO-NH-[alquilo C1-8], (CH2)n-CO-N[alquilo C1-8]2, (CH2)n-CO-NH-[cicloalquilo C3-8], alquenil C2-10-CO-O-[alquilo C1-6], alquenil C2-10-CO-NH2, alquenil C2-10-COOH, alquinil C2-10-COO-[alquilo C1-8], alquinil C2-10-CO-NH2, alquinil C2-10-COOH, (CH2)n-CR21-[CO-O-alquilo C1-6]2, (CH2)n-CR21-(CONH2)2, (CH2)n-CR21(COOH)2, (CH2)n-CR21R22CO-O[alquilo C1-6], (CH2)n-CR21R22-CONH2, (CH2)n-CR21R22-CO-NH-[alquilo C1-8], (CH2)n-CR21R22-CO-N[alquilo C1-8]2, (CH2)n-CR21R22COOH, (CH2)n-CO-R16, (CH2)n-CO-NH-C(CH3)2-COO[alquilo C1-8], (CH2)n-CO-NH-C(CH3)2-CONH2, (CH2)n-CO-NH-C(CH3)2-COOH, en los que los radicales alquilo, alquenilo, alquinilo y cicloalquilo, pueden estar sustituidos con átomos de fluor y en donde el radical arilo o heteroarilo puede estar sustituido con halogeno, CN, alquilo C1-6, cicloalquilo C3-6, O-alquilo C1-6, S(O)m-alquilo C1-6, SO2-NH2, COOH, CONH2, CO-O-alquilo C1-6, CO-alquilo C1-6 y en los que los radicales alquilo pueden estar sustituidos con átomos de fluor; R12 es H, alquilo C1-8, cicloalquilo C1-8, (CH2)n-arilo, (CH2)n-heteroarilo, en los que los radicales alquilo o cicloalquilo pueden estar sustituidos con átomos de fluor, y en los que el radical a
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