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 USEInfo
- Publication number
- 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
- Authority
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- Argentina
- Prior art keywords
- alkyl
- aryl
- sulfonyl
- conh2
- substituted
- Prior art date
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 24
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 20
- 125000000217 alkyl group Chemical group 0.000 abstract 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 15
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 13
- 125000000524 functional group Chemical group 0.000 abstract 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 11
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 10
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 10
- 125000003118 aryl group Chemical group 0.000 abstract 9
- 125000001153 fluoro group Chemical group F* 0.000 abstract 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 7
- 229910006069 SO3H Inorganic materials 0.000 abstract 7
- 125000003277 amino group Chemical group 0.000 abstract 7
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 7
- 150000003573 thiols Chemical class 0.000 abstract 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 5
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 abstract 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 5
- 125000004104 aryloxy group Chemical group 0.000 abstract 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 5
- 229910052794 bromium Inorganic materials 0.000 abstract 5
- 229910052801 chlorine Inorganic materials 0.000 abstract 5
- 239000000460 chlorine Substances 0.000 abstract 5
- 229910052740 iodine Inorganic materials 0.000 abstract 5
- 239000011630 iodine Substances 0.000 abstract 5
- 229920006395 saturated elastomer Polymers 0.000 abstract 5
- 102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- 108010046094 fatty-acid amide hydrolase Proteins 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- 125000005157 alkyl carboxy group Chemical group 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- -1 fluorosulfonyl Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000005764 inhibitory process Effects 0.000 abstract 2
- 125000002346 iodo group Chemical group I* 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000005026 carboxyaryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US930207P | 2007-12-27 | 2007-12-27 |
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| Publication Number | Publication Date |
|---|---|
| AR069970A1 true AR069970A1 (en) | 2010-03-03 |
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| Application Number | Title | Priority Date | Filing Date |
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| ARP080105707A AR069970A1 (en) | 2007-12-27 | 2008-12-23 | 3-N-PHENYL-1,3,4-OXADIAZOLONES 5-0-SUBSTITUTED FOR MEDICAL USE |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP2238131A1 (en) |
| JP (1) | JP2011507952A (en) |
| KR (1) | KR20100111691A (en) |
| CN (1) | CN101959881A (en) |
| AR (1) | AR069970A1 (en) |
| AU (1) | AU2008344032A1 (en) |
| BR (1) | BRPI0821482A2 (en) |
| CA (1) | CA2710743A1 (en) |
| CL (1) | CL2008003895A1 (en) |
| IL (1) | IL206419A0 (en) |
| MX (1) | MX2010006995A (en) |
| TW (1) | TW200932732A (en) |
| WO (1) | WO2009084970A1 (en) |
| ZA (1) | ZA201005306B (en) |
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| TW201028406A (en) * | 2008-12-23 | 2010-08-01 | Bial Portela & Ca Sa | 5-O-substituted 3-N-aryl-1,3,4-oxadiazolones for medical use |
| AR076687A1 (en) * | 2009-05-18 | 2011-06-29 | Infinity Pharmaceuticals Inc | ISOXAZOLINS AS INHIBITORS OF THE AMIDAHIDROLASA OF FATTY ACIDS AND PHARMACEUTICAL COM-POSITIONS CONTAINING THEM |
| 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 |
| WO2011123719A2 (en) | 2010-03-31 | 2011-10-06 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating abdominal, visceral and pelvic pain |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3931843A1 (en) * | 1989-09-23 | 1991-04-04 | Bayer Ag | SUBSTITUTED 1,3,4-OXA (THIA) DIAZOLINONE PROCESS FOR THEIR PREPARATION AND THEIR USE OF THE CONTROL OF ENDOPARASITES |
| DE19942354A1 (en) * | 1999-09-04 | 2001-03-08 | Aventis Pharma Gmbh | Substituted 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one, their manufacture and use in medicinal products |
| AU2002347985A1 (en) * | 2001-11-15 | 2003-06-10 | Eli Lilly And Company | Peroxisome proliferator activated receptor alpha agonists |
| DE10208987A1 (en) * | 2002-02-28 | 2003-09-11 | Aventis Pharma Gmbh | Substituted 3-phenyl-5-alkoxy-1,3,4-oxidiazol-2-ones, their preparation and use in drugs |
| US20090111778A1 (en) * | 2005-11-18 | 2009-04-30 | Richard Apodaca | 2-Keto-Oxazoles as Modulators of Fatty Acid Amide Hydrolase |
-
2008
- 2008-12-23 CN CN2008801276810A patent/CN101959881A/en active Pending
- 2008-12-23 CA CA2710743A patent/CA2710743A1/en not_active Abandoned
- 2008-12-23 TW TW097150238A patent/TW200932732A/en unknown
- 2008-12-23 AR ARP080105707A patent/AR069970A1/en unknown
- 2008-12-23 WO PCT/PT2008/000054 patent/WO2009084970A1/en not_active Ceased
- 2008-12-23 BR BRPI0821482-4A patent/BRPI0821482A2/en not_active IP Right Cessation
- 2008-12-23 CL CL2008003895A patent/CL2008003895A1/en unknown
- 2008-12-23 AU AU2008344032A patent/AU2008344032A1/en not_active Abandoned
- 2008-12-23 EP EP08866782A patent/EP2238131A1/en not_active Withdrawn
- 2008-12-23 MX MX2010006995A patent/MX2010006995A/en not_active Application Discontinuation
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- 2008-12-23 JP JP2010540610A patent/JP2011507952A/en not_active Withdrawn
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| AU2008344032A1 (en) | 2009-07-09 |
| TW200932732A (en) | 2009-08-01 |
| AU2008344032A8 (en) | 2010-08-19 |
| ZA201005306B (en) | 2011-04-28 |
| CL2008003895A1 (en) | 2010-06-25 |
| MX2010006995A (en) | 2010-08-18 |
| JP2011507952A (en) | 2011-03-10 |
| CA2710743A1 (en) | 2009-07-09 |
| CN101959881A (en) | 2011-01-26 |
| WO2009084970A1 (en) | 2009-07-09 |
| IL206419A0 (en) | 2010-12-30 |
| EP2238131A1 (en) | 2010-10-13 |
| KR20100111691A (en) | 2010-10-15 |
| BRPI0821482A2 (en) | 2015-07-14 |
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