AR044514A1 - ALFA CARBOXYLIC ACIDS REPLACED AS PPAR MODULATORS - Google Patents

ALFA CARBOXYLIC ACIDS REPLACED AS PPAR MODULATORS

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AR044514A1
AR044514A1 ARP040101236A ARP040101236A AR044514A1 AR 044514 A1 AR044514 A1 AR 044514A1 AR P040101236 A ARP040101236 A AR P040101236A AR P040101236 A ARP040101236 A AR P040101236A AR 044514 A1 AR044514 A1 AR 044514A1
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Argentina
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cr11r12
alkyl
links
heterocyclyl
ring
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ARP040101236A
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Pfizer
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Abstract

Acidos carboxílicos a-substituidos, las composiciones farmacéuticas conteniendo cantidades eficaces de dichos compuestos o sus sales, son útiles para tratar PPAR, específicamente trastornos relacionados con PPAR a/g tales como diabetes, dislipidemia, obesidad y trastornos inflamatorios. Reivindicación 1: Un compuesto de fórmula (1) o una sal o solvato farmacéuticamente aceptable del mismo, en el que, el anillo Q es arilo C6-10 o heterociclilo de (4-10) eslabones; R1 es H, halo, alquilo C1-8, alcoxi C1-8, CN, CF3, -O-CF3, -O-SO2-alquilo C1-8, -O-SO2-(CR11R12)tarilo C6-10, -(CR11R12)tcicloalquil C3-10-(CR11R12)t, -(CR11R12)t-cicloalquil C3-10-(CR11R12)t-O-, -(CR11R12)taril C6-10-(CR11R12)t, -(CR11R12)t-aril C6-10-(CR11R12)t- O-, -(CR11R12)t-heterociclil de (4-10) eslabones-(CR11R12)t, o -(CR11R12)t- heterociclil de (4-10) eslabones-(CR11R12)t-O-; en el que los átomos de carbono del anillo R1 están opcionalmente substituidos con 1 a 3 grupos R13; y los átomos de nitrógeno en el anillo de R1 están opcionalmente substituidos con 1 a 3 alquilo C1-8; R2 es H, alquilo C1-8, -(CR11R12)t-cicloalquilo C3-10, -(CR11R12)t-arilo C6-10, o -(CR11R12)t heterociclilo de (4-10) eslabones; y en el que los átomos de carbono de R2 están opcionalmente substituidos con 1 a 3 grupos R13; y los átomos de nitrógeno en el anillo de R2 están opcionalmente substituidos con 1 a 3 alquilo C1-8; R3 se selecciona entre el grupo constituido por las fórmulas (2), (3), (4) y (5); Y es -(C=O)- o -SO2-; Y" es NR10 u -O-; p es 0, 1 ó 2; cada q, r, y t son independientemente 0, 1, 2, 3, 4 ó 5; cada n es independientemente 0, 1, 2, 3 ó 4; cada k es independientemente 1, 2, o 3; cada m y s son independientemente 0, 1, 2 ó 3; cada j es 0, 1 ó 2; cada R4 es -(CR11R12)n-, -(CR11R12)n-S-(CR11R12)n-, -(CR11R12)n-NR10-, -(CR11R12)n-NR10-(CR11R12)n-O-, -(CR11R12)n-O-(CR11R12)k-NR10-, -(CR11R12)n-O- (CR11R12)n-, -(CR11R12)n-O-(CR11R12)k-O-(CR11R12)n-, -(CR11R12)n-CR11=CR12-(CR11R12)n-, o -CH=CH-(CR11R12)-O-(CH2)n-; cada R5 es un enlace o -(CR11R12)m-Z-(CR11R12)s; en el que Z es -CR11R12-, -O-NR10a-, o -S(O)j-; cada R6 es -(C=O)-OH, -(C=O)-OM+, -(C=O)-alquilo C1-8, -(C=O)-O-alquilo C1-8, -(C=O)-NR10R11, -(C=O)-NR10-SO2-R11, -SO2-NH- R10, -NH-SO2-R10, -(C=O)-NH-CºN, o R6 tiene una fórmula (6) o (7); M+ es un catión de metal alcalino o un catión de metal alcalinotérreo; cada R7 y R8 es independientemente H, alquilo C1-8, alcoxi C1-8, -(CR11R12)tcicloalquilo C3-10, - (CR11R12)tarilo C6-10, -(CR11R12)taril C6-10-O-, -(CR11R12)t heterociclilo de (4-10) eslabones o -(CR11R12)t heterociclil de (4-10) eslabones-O-; o R7 y R8 pueden opcionalmente tomarse juntos con el carbono al que están unidos para formar un cicloalquilo C3-10 o un heterociclilo de (3-10) eslabones; cada Ar1, Ar2, Ar3, y Ar4 representa arilo C6-10 o heterociclilo de (5-10) eslabones; en el que los átomos de carbono en el anillo de cada Ar1, Ar2, Ar3, y Ar4 están opcionalmente substituidos con uno a tres grupos R13; el anillo A representa un anillo de 3, 4, 5, 6 o 7 eslabones conteniendo opcionalmente 1 a 4 heteroátomos que pueden ser el mismo o diferente y que se seleccionan entre -N(R10a)-, O, y S(O)j, en el que j es 0, 1 ó 2, con la condición de que el anillo no contenga dos átomos de O ó S(O)j adyacentes, y en el que los átomos de carbono del resto A en el anillo estén opcionalmente substituidos con uno a tres grupos R13; R9 es alquilo C1-8, -(CR11R12)tarilo C6- 10 o -(CR11R12)t heterociclilo de (4-10) eslabones, en los que t son independientemente 0, 1, 2, 3, 4, o 5, en el que dichos grupos R9 están substituidos con 1 a 3 grupos independientemente seleccionados entre -(CR11R12)qNR10R11, - (CR11R12)qNR10alcanoilo C1-6, -(CR11R12)qO(CR11R12)rR10, y -(CR11R12)qR10; y en el que los restos heterociclilo, arilo y alquilo de los grupos anteriores están opcionalmente substituido con uno a tres grupos R13; R9a y R10 son independientemente H o alquilo C1-8; R11 y R12 son independientemente H, alquilo C1-8, hidroxi, o alcoxi C1-6; R10a se selecciona entre H, alquilo C1-8, -(C=O)-R14, -SO2NR15R16, o -S(O)jalquilo C1-6; cada R13 y R13a se seleccionan independientemente entre el grupo constituido por halo, ciano, nitro, trifluorometoxi, trifluorometilo, azido, hidroxi, alcoxi C1-6, alquilo C1-10, alquenilo C2-6, alquinilo C2-6, -O-(CR11R12)k-O-(CR11R12)n-, -(C=O)-R14, -(C=O)-O-R15, -O-(C=O)-R15, -NR15(C=O)-R16, -NR15(C=O)-O-R16, - (C=O)-NR15R16, -NR15R16, -NR15OR16, -SO2NR15R16, -S(O)jalquilo C1-6, -O-SO2-R14, -NR15-SO2-R16, R15-(CR11R12)tarilo C6-10, -(CR11R12)t heterociclilo de (4-10) eslabones,- (CR11R12)q(C=O)(CR11R12)tarilo C6-10, -CR11R12)q(C=O)(CR11R12)t heterociclilo de (4-10) eslabones, -(CR11R12)tO(CR11R12)qarilo C6-10, -(CR11R12)tO(CR11R12)qheterociclilo de (4-10) eslabones, -(CR11R12)qSO2(CR11R12)tarilo C6-10, y -(CR11R12)qSO2(CR11R12)t heterociclilo de (4-10) eslabones; 1 o 2 átomos de carbono en el anillo de los restos heterocíclicos de los grupos anteriores R13 y R13a están opcionalmente substituidos con 1 a 3 substituyentes seleccionados independientemente entre halo, ciano, nitro, trifluorometilo, trifluorometoxi, azido, -OR15, -(C=O)-R15, -(C=O)- O-R15, -O-(C=O)-R15, -NR15(C=O)-R16, -(C=O)-NR15R16, -NR15R16, -NR15OR16, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, -(CR11R12)tarilo C6-10, y -(CR11R12)t heterociclilo de (4-10) eslabones; cada R14, R15, y R16 se selecciona independientemente entre H, alquilo C1-6, -(CR11R12)t arilo C6-10, y -(CR11R12)t heterociclilo de (4-10) eslabones; 1 o 2 átomos de carbono en el anillo del grupo heterocíclico están opcionalmente substituidos con un resto oxo (=O), y los restos alquilo, arilo y heterocíclicos de los grupos anteriores R14, R15 y R16 están opcionalmente substituidos con 1 a 3 substituyentes seleccionados independientemente entre halo, ciano, nitro, -NR11R12, trifluorometilo, trifluorometoxi, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, hidroxi, y alcoxi C1-6; R17 es H, alquilo C1-8, -O-alquilo C1-8, halo, CN, OH, CF3, o -O-CF3; y en el que cualquiera de los substituyentes anteriormente mencionados comprenden un grupo CH3(metilo), CH2 (metileno), o CH (metino) que no está unido a un grupo halo, SO o SO2 o a un átomo de N, O ó S opcionalmente se soporta sobre dicho grupo un substituyente seleccionado entre hidroxi, halo, alquilo C1-4, alcoxi C1-4, -NH2, -NHalquilo C1-8, y -N(alquilo C1-8)2.A-substituted carboxylic acids, pharmaceutical compositions containing effective amounts of said compounds or their salts, are useful for treating PPAR, specifically disorders related to PPAR a / g such as diabetes, dyslipidemia, obesity and inflammatory disorders. Claim 1: A compound of formula (1) or a pharmaceutically acceptable salt or solvate thereof, wherein, the Q ring is C6-10 aryl or heterocyclyl of (4-10) links; R1 is H, halo, C1-8 alkyl, C1-8 alkoxy, CN, CF3, -O-CF3, -O-SO2-C1-8 alkyl, -O-SO2- (CR11R12) C6-10 taryl, - ( CR11R12) t-cycloalkyl C3-10- (CR11R12) t, - (CR11R12) t-cycloalkyl C3-10- (CR11R12) tO-, - (CR11R12) taril C6-10- (CR11R12) t, - (CR11R12) t-aryl C6-10- (CR11R12) t- O-, - (CR11R12) t-heterocyclyl of (4-10) links- (CR11R12) t, or - (CR11R12) t- heterocyclyl of (4-10) links- (CR11R12 ) tO-; wherein the carbon atoms of the R1 ring are optionally substituted with 1 to 3 R13 groups; and the nitrogen atoms in the ring of R1 are optionally substituted with 1 to 3 C1-8 alkyl; R2 is H, C1-8 alkyl, - (CR11R12) t-C3-10 cycloalkyl, - (CR11R12) t-aryl C6-10, or - (CR11R12) t heterocyclyl of (4-10) links; and wherein the carbon atoms of R2 are optionally substituted with 1 to 3 R13 groups; and the nitrogen atoms in the R2 ring are optionally substituted with 1 to 3 C1-8 alkyl; R3 is selected from the group consisting of formulas (2), (3), (4) and (5); Y is - (C = O) - or -SO2-; Y "is NR10 or -O-; p is 0, 1 or 2; each q, r, and t are independently 0, 1, 2, 3, 4 or 5; each n is independently 0, 1, 2, 3 or 4 ; each k is independently 1, 2, or 3; each mys are independently 0, 1, 2 or 3; each j is 0, 1 or 2; each R4 is - (CR11R12) n-, - (CR11R12) nS- ( CR11R12) n-, - (CR11R12) n-NR10-, - (CR11R12) n-NR10- (CR11R12) nO-, - (CR11R12) nO- (CR11R12) k-NR10-, - (CR11R12) nO- (CR11R12 ) n-, - (CR11R12) nO- (CR11R12) kO- (CR11R12) n-, - (CR11R12) n-CR11 = CR12- (CR11R12) n-, or -CH = CH- (CR11R12) -O- ( CH2) n-; each R5 is a bond or - (CR11R12) mZ- (CR11R12) s; where Z is -CR11R12-, -O-NR10a-, or -S (O) j-; each R6 is - (C = O) -OH, - (C = O) -OM +, - (C = O) -C 1-8 alkyl, - (C = O) -O-C 1-8 alkyl, - (C = O) - NR10R11, - (C = O) -NR10-SO2-R11, -SO2-NH- R10, -NH-SO2-R10, - (C = O) -NH-CºN, or R6 has a formula (6) or ( 7); M + is an alkali metal cation or an alkaline earth metal cation; each R7 and R8 is independently H, C1-8 alkyl, C1-8 alkoxy, - (CR11R12) C3-10 tcycloalkyl, - (CR11R12) C6 taryl -10, - (CR11R12) C6-10-O- taryl, - (CR11R12) t heterocyclyl of (4-10) links or - (CR11R12) t heterocyclyl of (4-10) links-O-; or R7 and R8 can optionally be taken together with the carbon to which they are attached to form a C3-10 cycloalkyl or a heterocyclyl of (3-10) links; each Ar1, Ar2, Ar3, and Ar4 represents C6-10 aryl or heterocyclyl of (5-10) links; wherein the carbon atoms in the ring of each Ar1, Ar2, Ar3, and Ar4 are optionally substituted with one to three R13 groups; Ring A represents a ring of 3, 4, 5, 6 or 7 links optionally containing 1 to 4 heteroatoms that can be the same or different and are selected from -N (R10a) -, O, and S (O) j , in which j is 0, 1 or 2, with the proviso that the ring does not contain two adjacent O or S (O) j atoms, and in which the carbon atoms of residue A in the ring are optionally substituted with one to three R13 groups; R9 is C1-8 alkyl, - (CR11R12) C6-10 taryl or - (CR11R12) t heterocyclyl of (4-10) links, in which t are independently 0, 1, 2, 3, 4, or 5, in wherein said R9 groups are substituted with 1 to 3 groups independently selected from - (CR11R12) qNR10R11, - (CR11R12) qNR10alkanoyl C1-6, - (CR11R12) qO (CR11R12) rR10, and - (CR11R12) qR10; and wherein the heterocyclyl, aryl and alkyl moieties of the above groups are optionally substituted with one to three R13 groups; R9a and R10 are independently H or C1-8 alkyl; R11 and R12 are independently H, C1-8 alkyl, hydroxy, or C1-6 alkoxy; R10a is selected from H, C1-8 alkyl, - (C = O) -R14, -SO2NR15R16, or -S (O) C1-6alkyl; each R13 and R13a are independently selected from the group consisting of halo, cyano, nitro, trifluoromethoxy, trifluoromethyl, azido, hydroxy, C1-6 alkoxy, C1-10 alkyl, C2-6 alkenyl, C2-6 alkynyl, -O- ( CR11R12) kO- (CR11R12) n-, - (C = O) -R14, - (C = O) -O-R15, -O- (C = O) -R15, -NR15 (C = O) -R16 , -NR15 (C = O) -O-R16, - (C = O) -NR15R16, -NR15R16, -NR15OR16, -SO2NR15R16, -S (O) C1-6 jalkyl, -O-SO2-R14, -NR15 -SO2-R16, R15- (CR11R12) C6-10 taryl, - (CR11R12) t heterocyclyl of (4-10) links, - (CR11R12) q (C = O) (CR11R12) C6-10 taryl, -CR11R12) q (C = O) (CR11R12) t heterocyclyl of (4-10) links, - (CR11R12) tO (CR11R12) qaryl C6-10, - (CR11R12) tO (CR11R12) qheterocyclyl of (4-10) links, - (CR11R12) qSO2 (CR11R12) C6-10 taryl, and - (CR11R12) qSO2 (CR11R12) t heterocyclyl of (4-10) links; 1 or 2 carbon atoms in the ring of the heterocyclic moieties of the above groups R13 and R13a are optionally substituted with 1 to 3 substituents independently selected from halo, cyano, nitro, trifluoromethyl, trifluoromethoxy, azido, -OR15, - (C = O) -R15, - (C = O) - O-R15, -O- (C = O) -R15, -NR15 (C = O) -R16, - (C = O) -NR15R16, -NR15R16, - NR15OR16, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, - (CR11R12) C6-10 taryl, and - (CR11R12) t heterocyclyl of (4-10) links; each R14, R15, and R16 is independently selected from H, C1-6 alkyl, - (CR11R12) t C6-10 aryl, and - (CR11R12) t heterocyclyl of (4-10) links; 1 or 2 carbon atoms in the ring of the heterocyclic group are optionally substituted with an oxo (= O) moiety, and the alkyl, aryl and heterocyclic moieties of the above groups R14, R15 and R16 are optionally substituted with 1 to 3 selected substituents independently between halo, cyano, nitro, -NR11R12, trifluoromethyl, trifluoromethoxy, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, hydroxy, and C1-6 alkoxy; R17 is H, C1-8 alkyl, -O-C1-8 alkyl, halo, CN, OH, CF3, or -O-CF3; and wherein any of the above-mentioned substituents comprise a CH3 (methyl), CH2 (methylene), or CH (methine) group that is not attached to a halo, SO or SO2 group or to an optionally N, O or S atom a substituent selected from hydroxy, halo, C1-4 alkyl, C1-4 alkoxy, -NH2, -NH C1-8 alkyl, and -N (C1-8 alkyl) 2 is supported on said group.

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