AR074622A1 - Derivados de acido ciclopentanocarboxilico condensados sustituidos con acilamino y su uso como productos farmaceuticos - Google Patents

Derivados de acido ciclopentanocarboxilico condensados sustituidos con acilamino y su uso como productos farmaceuticos

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Publication number
AR074622A1
AR074622A1 ARP090101536A ARP090101536A AR074622A1 AR 074622 A1 AR074622 A1 AR 074622A1 AR P090101536 A ARP090101536 A AR P090101536A AR P090101536 A ARP090101536 A AR P090101536A AR 074622 A1 AR074622 A1 AR 074622A1
Authority
AR
Argentina
Prior art keywords
series consisting
alkyl
ring
hydrogen
independently
Prior art date
Application number
ARP090101536A
Other languages
English (en)
Original Assignee
Sanofi Aventis
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=39870123&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR074622(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR074622A1 publication Critical patent/AR074622A1/es

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    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/62—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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Abstract

Son valiosos compuestos activos farmacéuticos. Específicamente, son inhibidores del receptor del gen de diferenciación endotelial 2 (Edg-2, EDG2), que es activado por ácido lisofosfatídico (LPA) y también se denomina receptor LPA1, y son útiles para el tratamiento de enfermedades tales como aterosclerosis, infarto de miocardio e insuficiencia cardiaca, por ejemplo. Se refiere además a procedimientos para preparar los compuestos de la fórmula (1), a su uso y a composiciones farmacéuticas que los comprenden. Reivindicación 1: Un compuesto de la fórmula (1), en cualquiera de sus formas estereoisoméricas o una mezcla de formas estereoisoméricas en cualquier relación, o su sal fisiológicamente aceptable, o un solvato fisiológicamente aceptable de cualquiera de ellos, en el que el anillo A es un anillo cicloalcano de 3 a 7 miembros, un anillo benceno o un anillo heterocíclico aromático monocíclico de 5 ó 6 miembros que comprende 1 ó 2 miembros de anillo hetero idénticos o diferentes seleccionados de la serie que consiste en N, N(R0), O y S, donde el anillo cicloalcano está opcionalmente sustituido con uno o más sustituyentes idénticos o diferentes seleccionados de la serie que consiste en flúor y alquilo C1-4, y el anillo benceno y los anillos heterocíclicos están opcionalmente sustituidos por uno o más sustituyentes idénticos o diferentes seleccionados de la serie que consiste en halógeno, R1, HO-, R1-O-, R1-C(O)-O-, R1-, S(O)2-O-, R1-S(O)m-, H2N-, R1-NH-, R1-N(R1)-, R1C(O)-NH-, R1-C(O)-N(R71)-, R1S(O)2-NH-, R1S(O)2-N(R71)-, R1-C(O)-, HO-C(O)-, R1-O-C(O)-, H2N-C(O)-, R1-NH-C(O)-, R1-N(R1)-C(O)-, H2N-S(O)2-, R1-NH-S(O)2-, R1-N(R1)-S(O)2-, NC-, O2N-, fenilo y Het; Y se selecciona de la serie que consiste en N(R10), S, O, C(R12)=C(R13), N=C(R14) y C(R15)=N; Z se selecciona de la serie que consiste en N y C(R16); R0 se selecciona de la serie que consiste en hidrógeno y R2; R1, R2, R11, R30, R33, R35, R54, R55, R57 y R58 se seleccionan, independientemente de cada grupo R1, R2, R11, R30, R33, R35, R54, R55, R57 y R58, de la serie que consiste en alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7 y cicloalquil C3-7-alquilo C1-4 que están todos opcionalmente sustituidos con uno o más sustituyentes R70 idénticos o diferentes; R3 y R5 se seleccionan, independientemente uno del otro, de la serie que consiste en hidrógeno, alquilo C1-4, fenil-alquilo C1-4, fenilo e hidroxi; R4 y R6 se seleccionan, independientemente uno del otro, de la serie que consiste en hidrógeno y alquilo C1-4; R10 se selecciona de la serie que consiste en hidrógeno y R11; R12, R13, R14, R15 y R16 se seleccionan, independientemente uno de otro, de la serie que consiste en hidrógeno, halógeno, alquilo C1-4, HO-alquilo C1-4, alquil C1-4-O-, alquil C1-4-S(O)m-, H2N-, alquil C1-4-NH-, alquil C1-4-N(alquilo C1-4)-, alquil C1-4-C(O)-, NC- y O2N-; R20 se selecciona de la serie que consiste en hidrógeno y alquilo C1-4; uno de los grupos R21 y R22 es un grupo de la fórmula: R24-R23-, y el otro de los grupos R21 y R22 se selecciona de la serie que consiste en hidrógeno, halógeno, R30, HO-, R30-O-, R30-C(O)-O-, R30-S(O)2-O-, R30-S(O)m-, H2N-, R30-NH-, R30-N(R30)-, R30-C(O)-NH-, R30-C(O)-N(R71), R30-S(O)2-NH-, R30-S(O)2-N(R71)-, R30-C(O)-, HO-C(O)-, R30-O-C(O)-, H2N-C(O)-, R30-NH-C(O)-, R30-N(R30)-C(O)-, H2N-S(O)2-, R30-NH-S(O)2-, R30-N(R30)-S(O)2-, NC-, O2N- y Het1; R23 es un enlace directo o una cadena que consiste en 1 a 5 miembros de cadena donde 0, 1 ó 2 miembros de la cadena son miembros de cadena hetero idénticos o diferentes seleccionados de la serie que consiste en N(R25), O, S, S(O) y S(O)2, pero dos miembros de cadena hetero pueden estar presentes en posiciones adyacentes solamente si uno de ellos se selecciona de la serie que consiste en S(O) y S(O)2 y el otro se selecciona de la serie que consiste en N(R25), O y S, y los otros miembros de cadena son grupos C(R26)(R26) idénticos o diferentes, donde dos grupos adyacentes C(R26)(R26) pueden conectarse entre sí por un doble enlace o un triple enlace; R24 se selecciona de la serie que consiste en hidrógeno, R31, HO-, R31-O-, R31-C(O)-O-, R31-S(O)m-, H2N-, R31-NH-, R31-N(R31)-, R31-C(O)-NH-, R31-C(O)-N(R71)-, R31-S(O)2-NH-, R31-S(O)2-N(R71)-, R31-C(O)-, HO-C(O)-, R31-O-C(O)-, H2N-C(O)-, R31-NH-C(O)-, R31-N(R31)-C(O)-, H2N-S(O)2-, R31-NH-S(O)2-, R31-N(R31)-S(O)2-, NC- y un anillo monocíclico, bicíclico o tricíclico de 3 a 10 miembros que está saturado o insaturado y contiene 0, 1, 2 ó 3 miembros de anillo hetero idénticos o diferentes seleccionados de la serie que consiste en N, N(R32), O, S, S(O) y S(O)2, donde el anillo está opcionalmente sustituido en los átomos de carbono del anillo por uno o más sustituyente idénticos o diferentes seleccionados de la serie que consiste en halógeno, R33, HO-, R33-O-, R33-C(O)-O-, R33-S(O)2-O-, R33-S(O)m-, H2N-, R33-NH-, R33-N(R33)-, R33-C(O)-NH-, R33-C(O)-N(R71)-, R33-S(O)2-NH-, R33-S(O)2-N(R71)-, H2N-S(O)2-NH-, R33-NH-S(O)2-NH-, R33-N(R33)-S(O)2-NH-, H2N-S(O)2-N(R71)-, R33-NH-S(O)2-N(71)-, R33-N(R33)-S(O)2-N(R71)-, R33-C(O)-, HO-C(O)-, R33-O-C(O)-, H2N-C(O)-, R33-NH-C(O)-, R33-N(R33)-C(O)-, H2N-S(O)2-, R33-NH-S(O)2-, R33-N(R33)-S(O)2-, NC-, O2N-, oxo, fenilo y Het, siempre que el número total de átomos C, N, O y S presente en los dos grupos R23 y R24, sea por lo menos 5; R25 se selecciona de la serie que consiste en hidrógeno y alquilo C1-4; R26, independientemente de cada grupo R26, se selecciona de la serie que consiste en hidrógeno, flúor, alquilo C1-4 y HO-, o dos grupos R26 unidos al mismo átomo de carbono son oxo, o dos de los grupos R26 o un grupo R25 y un grupo R26, junto con los miembros de cadena comprendidos, forman un anillo monocíclico de 3 a 7 miembros que está saturado y contiene 0, 1 ó 2 miembros de anillo hetero idénticos o diferentes seleccionados de la serie que consiste en N, N(R34), O, S, S(O) y S(O)2, donde el anillo está opcionalmente sustituido en átomos de carbono del anillo por uno o más sustituyentes idénticos o diferentes seleccionados de la serie que consiste en flúor y alquilo C1-4; R31 se selecciona de la serie que consiste en alquilo C1-6, alquenilo C2-6 y alquinilo C2-6, todos opcionalmente sustituidos con uno o más sustituyentes R70 idénticos o diferentes; R32 y R34 se seleccionan, independientemente uno del otro, de la serie que consiste en hidrógeno, R35, R35-S(O)2-, R35-C(O)-, R35-O-C(O)-, fenilo y Het; R50 se selecciona de la serie que consiste en R51-O- y R52-N(R53)-; R51 se selecciona de la serie que consiste en hidrógeno y R54; R52 se selecciona de la serie que consiste en hidrógeno, R55, NC- y R56-S(O)2-; R53 se selecciona de la serie que consiste en hidrógeno y R57; R56 se selecciona de la serie que consiste en R58 y fenilo; R60, independientemente de cada grupo R60, se selecciona de la serie que consiste en hidrógeno y alquilo C1-4; R70 se selecciona de la serie que consiste en HO-, R71-O-, R71-C(O)-O-, R71-S(O)m-, H2N-, R71-NH-, R71-N(R71)-, R71-C(O)-NH-, R71-C(O)-N(R71)-, R11-S(O)2-NH-, R71-S(O)2-N(R71)-, HO-C(O)-, R71-O-C(O)-, H2N-C(O)-, R71-NH-C(O)-, R71-N(R71)-C(O), H2N-S(O)2-, R71-NH-S(O)2-, R71-N(R71)-S(O)2-, NC-, oxo, fenilo y Het2; R71, independientemente de cada grupo R71, se selecciona entre alquilo C1-4, cicloalquilo C3-4 y cicloalquil C3-4-alquilo C1-2-; Het, independientemente de cada grupo Het, es un anillo heterocíclico de 4 a 7 miembros monocíclico que comprende 1, 2 ó 3 miembros de anillo hetero idénticos o diferentes seleccionados de la serie que consiste en N, N(R60), O, S, S(O) y S(O)2, donde el anillo está saturado o insaturado y está opcionalmente sustituido con, uno o más sustituyentes idénticos o diferentes seleccionados de la serie que consiste en halógeno, alquilo C1-4 y R70; Het1 es un anillo heterocíclico de 4 a 7 miembros monocíclico que comprende 1 ó 2 miembros de anillo hetero idénticos o diferentes seleccionados de la serie que consiste en N, N(R60), O, S, S(O) y S(O)2, donde el anillo esta saturado y está opcionalmente sustituido con uno o más sustituyentes idénticos o diferentes seleccionados de la serie que consiste en flúor y alquilo C1-4; Het2 es un anillo heterocíclico de 5 miembros o 6 miembros monocíclico que comprende 1, 2 ó 3 miembros de anillo hetero idénticos o diferentes de la serie que consiste en N, N(R60), O y S, donde el anillo es aromático y está opcionalmente sustituido con uno o más sustituyentes idénticos o diferentes seleccionados de la serie que consiste en halógeno, alquilo C1-4, alquil C1-4-O- y NC-; m, independientemente de cada número m, es un número entero seleccionado de la serie que consiste en 0, 1 y 2; fenilo, independientemente de cada grupo fenilo, está opcionalmente sustituido con uno o más sustituyentes idénticos o diferentes seleccionados de la serie que consiste en halógeno, alquilo C1-4, alquil C1-4-O- y NC-, a menos que se especifique lo contrario; cicloalquilo, independientemente del grupo cicloalquilo, e independientemente de cualquier otro sustituyente en el cicloalquilo, está opcionalmente sustituido con uno o más sustituyentes idénticos o diferentes seleccionados de flúor y alquilo C1-4; alquilo, alquenilo y alquinilo, independientemente del grupo alquilo, alquenilo y alquinilo, e independientemente de cualquier otro sustituyente en alquilo, alquenilo y alquinilo, está opcionalmente sustituido con uno o más sustituyentes flúor; siempre que el compuesto de la fórmula (1) no sea ácido 2-[(6,2',4'-triclorobifenil-3-carbonil)amino]indano-2-carboxílico, ácido 2-[(6-cloro-[1,1',4',1']terfenil-3-carbonil)amino]indano-2-carboxílico, 2-(4-cloro-3-feniletinil-benzoilamino)-indano-2-carboxílico, ácido 5-(4-cloro-fenil)-2-[4-(2-metil-1H-benzoimidazol-1-ilmetil)-benzoilamino]-indano-2-carboxílico o éter etílico de ácido 5-(4-cloro-fenil)-2-[4-(2-metil-1H-benzoimidazol-1-ilmetil)-benzoilamino]-indano-2-carboxílico.
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