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US 6,610,738 B2Granted
N-disubstituted carbamoyloxy flavones
AssigneeBiogal Pharmaceutical Company, Ltd.
InventorsIldiko B. Mihókné, György Tóth, Sándor Molnár, Tivadar Tamás, György Sulyok, Eva K. Mudráné
Life of this patent
Estimating the term…
Abstract
The invention relates to new flavone derivaties which have at least one N-disubstituted carbamoyloxy unit (OOCNR6(R7))coupled directly to one or both aromatic rings of the flavone molecule.
Claims34
A compound of the formula
- wherein each of R1, R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OOCNR6(R7), in which each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different;
- OR8, wherein R8 is hydrogen, methyl or ethyl
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl or ethyl;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3, R4 and R5 is OOCNR6(R7) and wherein at least one of R4 and R5 is other than hydrogen.
10 more elements
A compound of the formula
- wherein R4 is OOCNR6(R7), in which each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different, and wherein R4 occurs in the 2′, 3′ or 4′ position;
- and
- wherein each of R1, R2, R3, and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OR8, wherein R8 is hydrogen, methyl, or ethyl;
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN.
9 more elements
A compound of the formula
- wherein
- R1 is OOCNR6(R7), in which each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different;
- and
- wherein R1 occurs in the 5, 6, 7, or 8 position;
- and
- wherein each of R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OR8, wherein R8 is hydrogen;
- methyl;
- or ethyl;
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR11,
- wherein R11 is hydrogen;
- sodium;
- potassium;
- or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen;
- methyl;
- or ethyl;
- NO2;
- and
- CN;
- and wherein at least one of R4 and R5 is other than hydrogen.
21 more elements
A compound of the formula
- wherein each of R1 and R4 is OOCNR6(R7) and R1 occurs in the 5, 6, 7, or 8 position and R4 occurs in the 2′, 3′, or 4′ position, and each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different;
- and
- wherein each of R2, R3, and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OR8, wherein R8 is hydrogen, methyl, or ethyl;
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN.
9 more elements
A compound of the formula
- wherein
- R1, R2, R3 and R4 are selected from the group consisting of:
- hydrogen;
- OOCNR5(R6), wherein each of R5 and R6 is methyl or ethyl and in which each of R5 and R6 may be the same or different;
- OR7, wherein R7 is methyl or ethyl;
- wherein each of R8 and R9 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR10, wherein R10 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR11R12, wherein each of R11 and R12 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3 and R4 is OOCNR5(R6);
- and wherein at least one of R3 and R4 is other than hydrogen.
12 more elements
A compound of the formula
- wherein each of R1, R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OOCNR6(R7), in which each of R6 and R7 is hydrogen, or a lower alkyl of 1 to 4 carbon atoms and in which each of R6 and R7 may be the same or different;
- OR8, wherein R8 is hydrogen, or a lower alkyl of 1 to 4 carbon atoms;
- wherein each of R9 and R10 is hydrogen or a lower alkyl of 1 to 4 carbon atoms;
- a halogen atom selected from the group consisting of fluoride, chloride, bromide and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or a lower alkyl of 1 to 4 carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen or a lower alkyl of 1 to 4 carbon atoms;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3, R4 and R5 is OOCNR6(R7);
- and wherein at least one of R4 and R5 is other than hydrogen.
11 more elements
A pharmaceutical composition comprising a compound of the formula
- wherein each of R1, R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OOCNR6(R7), in which each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different;
- OR8, wherein R8 is hydrogen, methyl or ethyl
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl or ethyl;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3, R4 and R5 is OOCNR6(R7);
- and a pharmaceutically acceptable carrier for said compound.
11 more elements
A pharmaceutical composition comprising a compound of the formula
- wherein R4 is OOCNR6(R7), in which each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different, and wherein R4 occurs in the 2, 3 or 4 position;
- and
- wherein each of R1, R2, R3, and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OR8, wherein R8 is hydrogen, methyl, or ethyl;
- wherein each of R9 and R10 hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR11 wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN;
- and a pharmaceutically acceptable carrier for said compound.
10 more elements
A pharmaceutical composition comprising a compound of the formula
- wherein
- R1 is OOCNR6(R7), in which each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different;
- and wherein R1 occurs in the 5, 6, 7, or 8 position;
- and
- wherein each of R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OR8, wherein R8 is hydrogen, methyl, or ethyl;
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN;
- and a pharmaceutically acceptable carrier for said compound.
12 more elements
A pharmaceutical composition comprising a compound of the formula
- wherein each of R1 and R4 is OOCNR6(R7) and R1 occurs in the 5, 6, 7, or 8 position and R4 occurs in the 2, 3, or 4 position, and each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different;
- and
- wherein each of R2, R3, and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OR8, wherein R8 is hydrogen, methyl, or ethyl;
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN;
- and a pharmaceutically acceptable carrier for said compound.
10 more elements
A pharmaceutical composition comprising a compound of the formula
- wherein
- R1, R2, R3 and R4 are selected from the group consisting of:
- hydrogen;
- OOCNR5(R6), wherein each of R5 and R6 is methyl or ethyl and in which each of R5 and R6 may be the same or different;
- OR7, wherein R7 methyl or ethyl;
- wherein each of R8 and R9 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR10, wherein R10 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR11R12, wherein each of R11 and R12 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3 and R4 is OOCNR5(R6);
- and a pharmaceutically acceptable carrier for said compound.
12 more elements
A pharmaceutical composition comprising a compound of the formula
- wherein each of R1, R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OOCNR6 (R7), in which each of R6 and R7 is hydrogen, or a lower alkyl of 1 to 4 carbon atoms and in which each of R6 and R7 may be the same or different;
- OR8, wherein R6 is hydrogen, or a lower alkyl of 1 to 4 carbon atoms;
- wherein each of R9 and R10 is hydrogen or a lower alkyl of 1 to 4 carbon atoms;
- a halogen atom selected from the group consisting of fluoride, chloride, bromide and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or a lower alkyl of 1 to 4 carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen or a lower alkyl of 1 to 4 carbon atoms;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3, R4 and R5 is OOCNR6 (R7);
- and a pharmaceutically acceptable carrier for said compound.
11 more elements
A method for inhibiting acetyicholine esterase activity by administering;
- to a host in need of acetylcholine esterase inhibition, an effective therapeutic acetyicholine esterase amount of a compound of the formula
- wherein each of R1, R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OOCNR6 (R7), in which each of R6 and R7 is hydrogen, methyl or ethyl and in which each of R6 and R7 may be the same or different;
- OR8, wherein R8 is hydrogen, methyl or ethyl
- wherein each of R9 and R10 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen, methyl or ethyl;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3, R4 and R5 is OOCNR6 (R7).
11 more elements
A method for inhibiting acetylcholine esterase activity by administering;
- to a host in need of acetylcholine esterase inhibition, an effective therapeutic acetylcholine esterase amount of a compound of the formula
- wherein
- R1, R2, R3 and R4 are selected from the group consisting of:
- hydrogen;
- OOCNR5 (R6), wherein each of R5 and R6 is methyl or ethyl and in which each of R5 and R6 may be the same or different;
- OR7, wherein R7 methyl or ethyl;
- wherein each of R8 and R9 is hydrogen or methyl;
- a halogen atom selected from the group consisting of fluoride, chloride, and iodide;
- COOR10, wherein R10 is hydrogen, sodium, potassium, or an alkyl of one to two carbon atoms;
- CONR11 R12, wherein each of R11 and R12 is hydrogen, methyl, or ethyl;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3 and R4 is OOCNR5 (R6).
12 more elements
A method for inhibiting acetyicholine esterase activity by administering;
- to a host in need of acetyicholine esterase inhibition, an effective therapeutic acetylcholine esterase amount of a compound of the formula
- wherein each of R1, R2, R3, R4 and R5 is a substituent selected from the group consisting of:
- hydrogen;
- OOCNR6 (R7), in which each of R6 and R7 is hydrogen, or a lower alkyl of 1 to 4 carbon atoms and in which each of R6 and R7 may be the same or different;
- OR8, wherein R8 is hydrogen, or a lower alkyl of 1 to 4 carbon atoms;
- wherein each of R9 and R10 is hydrogen or a lower alkyl of 1 to 4 carbon atoms;
- a halogen atom selected from the group consisting of fluoride, chloride, bromide and iodide;
- COOR11, wherein R11 is hydrogen, sodium, potassium, or a lower alkyl of 1 to 4 carbon atoms;
- CONR12R13, wherein each of R12 and R13 is hydrogen or a lower alkyl of 1 to 4 carbon atoms;
- NO2;
- and
- CN;
- and
- wherein at least one of R1, R2, R3, R4 and R5 is OOCNR6 (R7).
11 more elements
Dependencies are inferred from the claim text.