AR069970A1 - 3-N-PHENYL-1,3,4-OXADIAZOLONES 5-0-SUBSTITUTED FOR MEDICAL USE - Google Patents

3-N-PHENYL-1,3,4-OXADIAZOLONES 5-0-SUBSTITUTED FOR MEDICAL USE

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AR069970A1
AR069970A1 ARP080105707A ARP080105707A AR069970A1 AR 069970 A1 AR069970 A1 AR 069970A1 AR P080105707 A ARP080105707 A AR P080105707A AR P080105707 A ARP080105707 A AR P080105707A AR 069970 A1 AR069970 A1 AR 069970A1
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alkyl
aryl
sulfonyl
conh2
substituted
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ARP080105707A
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Spanish (es)
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Araujo Soares Da Silva Patricio Manuel Vieira
Laszlo Erno Kiss
Santos Ferreira Humberto Dos
David Alexander Learmonth
Alexander Beliaev
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Bial Portela & Ca Sa
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Publication of AR069970A1 publication Critical patent/AR069970A1/en

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Abstract

Composiciones farmacéuticas, usos para la inhibicion de FAAH (amida hidrolasa de ácido graso), y procedimiento de preparacion. Reivindicacion 1: Compuesto caracterizado por la formula (1), en la que R1 a R5 independientemente uno de otro representan: hidrogeno; alquilo C1-6, cicloalquilo C3-8, arilo C6-10, aril C6-10-alquilo C1-8, alcoxi C1-6, ariloxi C6-10, aril C6-10-ariloxi C1-8, alcoxi C1-6-carbonilo, ariloxi C6-10-carbonilo, aril C6-10-alcoxi C1-8-carbonilo, alquil C1-6-carbonilo, aril C6-10-carbonilo, aril C6-10-alquil C1-8-carbonilo, alquil C1-6-carboxi, aril C6-10-carboxi, alquil C1-6-mercaptilo, aril C6-10-mercaptilo, alquil C1-6-mercaptocarbonilo, cicloalquil C3-8-mercaptocarbonilo, aril C6-10-mercaptocarbonilo, alquil C1-6-mercaptocarboxi, aril C6-10-mercaptocarboxi, alquil C1-6-sulfonilo, aril C6-10-sulfonilo, alquil C1-6-sulfoxi, aril C6-10-sulfoxi, en el que cada uno está opcionalmente sustituido una o varias veces por alquilo C1-6, alcoxi C1-6, ariloxi C6-10, CO2H; SO3H; CONH2, SO2NH2, CONH2 o SO2NH2 en el que el grupo funcional amino está sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10 o aril C6-10-alquilo C1-4 y en el que en caso de un grupo funcional amino sustituido por dialquilo C1-6 los restos alquilo pueden combinarse para formar anillos de 5 o 6 miembros; amino; amino sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10, aril C6-10-alquilo C1-4, alquil C1-6-carbonilo, aril C6-10-carbonilo, alquil C1-6-sulfonilo y aril C6-10-sulfonilo; tiol; hidroxilo; nitro; ciano; fluoro; cloro; bromo; yodo; CF3 o OCF3, CO2H; SO3H; amino; amino sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10, aril C6-10-alquilo C1-6, alquil C1-6-carbonilo, aril C6-10-carbonilo, alquil C1-6-sulfonilo y aril C6-10-sulfonilo; un amino disustituido de la formula (2) en la que o representa 0 o 1 y W representa O, CH2, o NR6, seleccionándose R6 de hidrogeno y alquilo C1-6 y en la que los grupos metileno en la formula (2) pueden estar opcionalmente sustituidos una o dos veces por alquilo C1-6, fluoro o cloro; CONH2, SO2NH2 CONH2 o SO2NH2 donde el grupo funcional amino está sustituido una o dos veces por restos seleccionados de alquilo C1-6, arilo C6-10 o aril C6-10-alquilo C1-6 y donde en el caso de un grupo funcional amino sustituido por dialquilo C1-6 los restos alquilo pueden estar combinados para formar anillos de 5 o 6 miembros; tiol; hidroxilo; nitro; ciano; fluorosulfonilo; halogeno seleccionado de fluoro, cloro, bromo o yodo; CF3, OCF3 o un sistema de anillo heterocíclico saturado, insaturado o aromático de hasta 10 átomos, opcionalmente sustituido una o varias veces por alquilo C1-6 alcoxi C1-6, COOH; SO3H; CONH2, SO2NH2, CONH2 o SO2NH2 en el que el grupo funcional amino está sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10 o aril C6-10-alquilo C1-4 y en el que en el caso de un grupo funcional amino sustituido por dialquilo C1-6 los restos alquilo pueden combinarse para formar anillos de 5 o 6 miembros; amino; amino sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10, aril C6-10-alquilo C1-4, alquil C1-6-carbonilo, aril C6-10-carbonilo, alquil C1-6-sulfonilo y aril C6-10-sulfonilo; tiol; hidroxilo; nitro; ciano; fluoro; cloro; bromo; yodo; CF3 o OCF3 y donde dos o más cualesquiera de R1 a R5 pueden estar combinados para formar sistemas de homo- o heteroanillos saturados, insaturados o aromáticos anillados; n representa 0 o 1; m representa 0, 1, 2, 3, 4, 5 o 6; X representa O o S; Y representa a) hidrogeno; b) alquilo C1-18, alquileno C2-18 mono- o poliinsaturado, cicloalquilo C3-8, arilo C6-10, aril C6-10-alquilo C1-8, alcoxi C1-6, ariloxi C6-10, aril C6-10-alcoxi C1-8, alcoxi C1-6-carbonilo, ariloxi C6-10-carbonilo, aril C6-10-alcoxi C1-8-carbonilo, alquil C1-6-carbonilo, aril C6-10-carbonilo, aril C6-10-alquil C1-8-carbonilo, alquil C1-6-carboxi, aril C6-10-carboxi, alquil C1-6-mercaptilo, aril C6-10-mercaptilo, alquil C1-6-mercaptocarbonilo, cicloalquil C3-C8-mercaptocarbonilo, aril C6-10-mercaptocarbonilo, alquil C1-6-mercaptocarboxi, aril C6-10-mercaptocarboxi, alquil C1-C6-sulfonilo, aril C6-10-sulfonilo, alquil C1-6-sulfoxi, aril C6-10-sulfoxi, o un sistema de anillo heterocíclico saturado, insaturado o aromático de hasta 10 átomos, en el que cada uno está opcionalmente sustituido una o varias veces por: bi) alquilo C1-6, cicloalquilo C3-8, arilo C6-10, aril C6-10-alquilo C1-8, alcoxi C1-6, ariloxi C6-10, aril C6-10-alcoxi C1-8, alcoxi C1-6-carbonilo, ariloxi C6-10-carbonilo, aril C6-10-alcoxicarbonilo C1-8, alquil C1-6-carbonilo, aril C6-10-carbonilo, aril C6-10-alquil C1-6-carbonilo, alquil C1-6-carboxi, aril C6-10-carboxi, alquil C1-6-mercaptilo, aril C6-10-mercaptilo, alquil C1-6-mercaptocarbonilo, cicloalquil C3-8-mercaptocarbonilo, aril C6-10-mercaptocarbonilo, alquil C1-6-mercaptocarboxi, aril C6-10-mercaptocarboxi, alquil C1-6-sulfonilo, aril C6-10-sulfonilo, alquil C1-6-sulfoxi, aril C6-10-sulfoxi; estando cada uno opcionalmente sustituido una o varias veces por alquilo C1-6, alcoxi C1-6, CONH2, SO2NH2 CONH2 o SO2NH2 donde el grupo funcional amino está sustituido una o dos veces por alquilo C1-6, SO3H; CO2H; amino; amino sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10, aril C6-10-alquilo C1-6, alquil C1-6-carbonilo, aril C6-10-carbonilo, alquil C1-6-sulfonilo y aril C6-10-sulfonilo; tiol; hidroxilo; nitro; ciano; fluoro; cloro; bromo; yodo; CF3 o OCF3, en el que varios de los sustituyentes en b1) pueden combinarse para formar sistemas de homo- o heteroanillos saturados, insaturados o aromáticos anillados; o por b2) hidroxi; tiol; nitro; ciano; fluoro; cloro; bromo; yodo; CF3, CO2H; SO3H; OCF3, CONH2, SO2NH2, CONH2 o SO2NN2 en el que el grupo funcional amino está sustituido una o dos veces por restos seleccionados de alquilo C1-6, arilo C6-10, o aril C6-10-alquilo C1-6 y en el que en el caso de un grupo funcional amino sustituido por dialquilo C1-6 los restos alquilo pueden estar combinados para formar anillos de 5 o 6 miembros; amino; amino sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10, aril C6-10-alquilo C1-8, alquil C1-6-carbonilo, aril C6-10-carbonilo, alquil C1-6-sulfonilo y aril C6-10-sulfonilo; o un amino disustituido de la formula (2) en la que o representa 0 o 1 y W representa O, CH2, o NR6, seleccionándose R6 de hidrogeno y alquilo C1-6 y en la que los grupos metileno en la formula (2) pueden estar opcionalmente sustituidos una o dos veces por alquilo C1-6, fluoro o cloro; o por b3) un sistema de anillo heterocíclico saturado, insaturado o aromático de hasta 10 átomos, opcionalmente sustituido una o varias veces por alquilo C1-6, alcoxi C1-6, COOH; SO3H; CONH2, SO2NH2, CONH2 o SO2NH2 en el que el grupo funcional amino está sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10 o aril C6-10-alquilo C1-4 y en el que en el caso de un grupo funcional amino sustituido por dialquilo C1-6 los restos alquilo pueden combinarse para formar anillos de 5 o 6 miembros; amino; amino sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10, aril C6-10-alquilo C1-4, alquil C1-6-carbonilo, aril C6-10-carbonilo, alquil C1-6-sulfonilo y aril C6-10-sulfonilo; tiol; hidroxilo; nitro; ciano; fluoro; cloro; bromo; yodo; CF3 o OCF3, c) SO3H; amino; amino sustituido una o más veces por restos seleccionados de alquilo C1-6, arilo C6-10, aril C6-10-alquilo C1-8, alquil C1-6-carbonilo, aril C6-10-carbonilo, alquil C1-6-sulfonilo y aril C6-10-sulfonilo; CONH2, SO2NH2 CONH2 o SO2NH2 en el que el grupo funcional amino está sustituido una o dos veces por restos seleccionados de alquilo C1-6, arilo C6-10 o aril C6-10-alquilo C1-6 y en el que en el caso de un grupo funcional amino sustituido por dialquilo C1-6 los restos alquilo pueden estar combinados para formar anillos de 5 o 6 miembros; tiol; hidroxilo; nitro; ciano; fluorosulfonilo; halogeno seleccionado de fluoro, cloro, bromo o yodo; CF3 o OCF3 o un estereoisomero, sal farmacéuticamente aceptable o éster, o un profármaco de los mismos para inhibicion de amida hidrolasa de ácidos grasos (FAAH).Pharmaceutical compositions, uses for the inhibition of FAAH (fatty acid amide hydrolase), and preparation process. Claim 1: Compound characterized by formula (1), wherein R1 to R5 independently of one another represent: hydrogen; C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, C6-10 aryl-C1-8 alkyl, C1-6 alkoxy, C6-10 aryloxy, C6-10 aryl-C1-8 aryloxy, C1-6 alkoxy carbonyl, C6-10 aryloxycarbonyl, C6-10 aryl-C1-8 alkoxycarbonyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C6-10 arylC 1-8 alkylcarbonyl, C1- alkyl 6-carboxy, C6-10-carboxy aryl, C1-6-mercaptyl alkyl, C6-10-mercaptyl aryl, C1-6-mercaptocarbonyl alkyl, C3-8-mercaptocarbonyl cycloalkyl, C6-10-mercaptocarbonyl, C1-6 alkyl -mercaptocarboxy, C6-10-mercaptocarboxy aryl, C1-6-sulfonyl alkyl, C6-10-sulfonyl aryl, C1-6-sulfoxy alkyl, C6-10-sulfoxy aryl, in which each is optionally substituted once or several times by C1-6 alkyl, C1-6 alkoxy, C6-10 aryloxy, CO2H; SO3H; CONH2, SO2NH2, CONH2 or SO2NH2 in which the amino functional group is substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl or C6-10 aryl-C1-4 alkyl and in which case an amino functional group substituted by C1-6 dialkyl alkyl moieties can be combined to form 5 or 6 member rings; Not me; amino substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl, C6-10 aryl-C1-4 alkyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C1-6 alkyl sulfonyl and C6-10-sulfonyl aryl; thiol; hydroxyl; nitro; cyano; fluoro; chlorine; bromine; iodine; CF3 or OCF3, CO2H; SO3H; Not me; amino substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl, C6-10 aryl-C1-6 alkyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C1-6 alkyl sulfonyl and C6-10-sulfonyl aryl; a disubstituted amino of the formula (2) in which o represents 0 or 1 and W represents O, CH2, or NR6, R6 being selected from hydrogen and C1-6 alkyl and in which the methylene groups in the formula (2) can be optionally substituted once or twice by C1-6 alkyl, fluoro or chloro; CONH2, SO2NH2 CONH2 or SO2NH2 where the amino functional group is substituted once or twice by moieties selected from C1-6 alkyl, C6-10 aryl or C6-10 aryl-C1-6 alkyl and where in the case of an amino functional group substituted by C1-6 dialkyl the alkyl moieties may be combined to form 5 or 6 member rings; thiol; hydroxyl; nitro; cyano; fluorosulfonyl; halogen selected from fluoro, chloro, bromo or iodo; CF3, OCF3 or a saturated, unsaturated or aromatic heterocyclic ring system of up to 10 atoms, optionally substituted once or several times by C1-6 alkyl C1-6 alkoxy, COOH; SO3H; CONH2, SO2NH2, CONH2 or SO2NH2 in which the amino functional group is substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl or C6-10 aryl-C1-4 alkyl and in which case of an amino functional group substituted by C1-6 dialkyl the alkyl moieties can be combined to form 5 or 6 member rings; Not me; amino substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl, C6-10 aryl-C1-4 alkyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C1-6 alkyl sulfonyl and C6-10-sulfonyl aryl; thiol; hydroxyl; nitro; cyano; fluoro; chlorine; bromine; iodine; CF3 or OCF3 and where any two or more of R1 to R5 may be combined to form saturated, unsaturated or aromatic ring-shaped homo- or hetero-ring systems; n represents 0 or 1; m represents 0, 1, 2, 3, 4, 5 or 6; X represents O or S; Y represents a) hydrogen; b) C1-18 alkyl, mono- or polyunsaturated C2-18 alkylene, C3-8 cycloalkyl, C6-10 aryl, C6-10 aryl-C1-8 alkyl, C1-6 alkoxy, C6-10 aryloxy, C6-10 aryl -C 1-8 alkoxy, C 1-6 alkoxycarbonyl, C6-10 aryloxycarbonyl, C6-10 aryl-C 1-8 alkoxycarbonyl, C 1-6 alkylcarbonyl, C6-10 arylcarbonyl, C6-10 aryl -C 1-8 alkylcarbonyl, C 1-6 alkylcarboxy, C 1-10 arylcarboxy, C 1-6 alkyl mercaptyl, C 1-10 aryl-mercaptyl, C 1-6 alkyl mercaptocarbonyl, C 3-6 cycloalkyl mercaptocarbonyl, C6-10-mercaptocarbonyl aryl, C1-6-mercaptocarboxy alkyl, C6-10-mercaptocarboxy aryl, C1-C6-sulfonyl alkyl, C6-10-sulfonyl aryl, C1-6-sulfoxy alkyl, C6-10-sulfoxy aryl, or a saturated, unsaturated or aromatic heterocyclic ring system of up to 10 atoms, in which each is optionally substituted once or several times by: bi) C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, C6-10 aryl -C 1-8 alkyl, C 1-6 alkoxy, C6-10 aryloxy, C6-10 aryl-C 1-8 alkoxy, C 1-6 alkoxycarbonyl, C6-10 aryloxycarbonyl, C6-10 aryl-C1-8 alkoxycarbonyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C6-10 arylC1-6 alkylcarbonyl, C1-6 alkylcarboxy, C6-10 carboxy aryl, C1-6-mercaptyl alkyl, C6-10-mercaptyl aryl, C1-6-mercaptocarbonyl alkyl, C3-8-mercaptocarbonyl cycloalkyl, C6-10-mercaptocarbonyl, C1-6-mercaptocarboxy alkyl, C6-10-mercaptocarboxy aryl, alkyl C1-6-sulfonyl, C6-10-aryl sulfonyl, C1-6-sulfoxy alkyl, C6-10-sulfoxy aryl; each optionally substituted once or several times by C1-6 alkyl, C1-6 alkoxy, CONH2, SO2NH2 CONH2 or SO2NH2 where the amino functional group is substituted once or twice by C1-6 alkyl, SO3H; CO2H; Not me; amino substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl, C6-10 aryl-C1-6 alkyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C1-6 alkyl sulfonyl and C6-10-sulfonyl aryl; thiol; hydroxyl; nitro; cyano; fluoro; chlorine; bromine; iodine; CF3 or OCF3, in which several of the substituents in b1) can be combined to form saturated, unsaturated or aromatic ring-shaped homo- or hetero-ring systems; or by b2) hydroxy; thiol; nitro; cyano; fluoro; chlorine; bromine; iodine; CF3, CO2H; SO3H; OCF3, CONH2, SO2NH2, CONH2 or SO2NN2 in which the amino functional group is substituted once or twice by moieties selected from C1-6 alkyl, C6-10 aryl, or C6-10 aryl-C1-6 alkyl and wherein in the case of an amino functional group substituted by C1-6 dialkyl the alkyl moieties may be combined to form 5 or 6 member rings; Not me; amino substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl, C6-10 aryl-C1-8 alkyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C1-6 alkyl sulfonyl and C6-10-sulfonyl aryl; or a disubstituted amino of the formula (2) in which o represents 0 or 1 and W represents O, CH2, or NR6, R6 being selected from hydrogen and C1-6 alkyl and in which the methylene groups in the formula (2) they may be optionally substituted once or twice by C1-6 alkyl, fluoro or chloro; or by b3) a saturated, unsaturated or aromatic heterocyclic ring system of up to 10 atoms, optionally substituted once or several times by C1-6 alkyl, C1-6 alkoxy, COOH; SO3H; CONH2, SO2NH2, CONH2 or SO2NH2 in which the amino functional group is substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl or C6-10 aryl-C1-4 alkyl and in which case of an amino functional group substituted by C1-6 dialkyl the alkyl moieties can be combined to form 5 or 6 member rings; Not me; amino substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl, C6-10 aryl-C1-4 alkyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C1-6 alkyl sulfonyl and C6-10-sulfonyl aryl; thiol; hydroxyl; nitro; cyano; fluoro; chlorine; bromine; iodine; CF3 or OCF3, c) SO3H; Not me; amino substituted one or more times by moieties selected from C1-6 alkyl, C6-10 aryl, C6-10 aryl-C1-8 alkyl, C1-6 alkylcarbonyl, C6-10 arylcarbonyl, C1-6 alkyl sulfonyl and C6-10-sulfonyl aryl; CONH2, SO2NH2 CONH2 or SO2NH2 in which the amino functional group is substituted once or twice by moieties selected from C1-6 alkyl, C6-10 aryl or C6-10 aryl-C1-6 alkyl and in which in the case of an amino functional group substituted by C1-6 dialkyl the alkyl moieties may be combined to form 5 or 6 member rings; thiol; hydroxyl; nitro; cyano; fluorosulfonyl; halogen selected from fluoro, chloro, bromo or iodo; CF3 or OCF3 or a stereoisomer, pharmaceutically acceptable salt or ester, or a prodrug thereof for fatty acid amide hydrolase (FAAH) inhibition.

ARP080105707A 2007-12-27 2008-12-23 3-N-PHENYL-1,3,4-OXADIAZOLONES 5-0-SUBSTITUTED FOR MEDICAL USE AR069970A1 (en)

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WO2010151160A1 (en) * 2009-06-24 2010-12-29 Bial - Portela & Ca., S.A. O-substituted 3-n-heteroaryl-1,3,4-oxadiazolones for medical use
US20130150346A1 (en) 2010-01-08 2013-06-13 Quest Ventures Ltd. Use of FAAH Inhibitors for Treating Parkinson's Disease and Restless Legs Syndrome
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