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US 9,562,031 B1Granted
Phenethyldihydrobenzodioxolones and methods of use
AssigneeSequoia Sciences, Inc.
InventorsRussell B Williams, Gary Eldridge, Courtney M. Starks, Peter Robert Guzzo, Zhongping Huang
Life of this patent
Estimating the term…
Abstract
The present invention generally relates to phenethyldihydrobenzodioxolone compounds and compositions useful for reducing or inhibiting tumor growth. It also relates to methods of use and the preparation of phenethyldihydrobenzodioxolone compounds.
Claims43
A compound according to formula:
- or stereoisomers thereof, wherein R1 is selected from the group consisting of methoxy, ethoxy, —SCH3, —SCH2CH3, and —NR8R9;
- R2 is selected from the group consisting of hydrogen, hydroxyl, alkoxy, amino, aminoalkyl, aminoalkenyl, aminoalkynyl, halide, haloalkyl, hydroxyalkyl, —NHCN, aminocarbonyl, hydroxyaminocarbonyl, alkylaminocarbonyl, acyloxy, nitrile, —CH2CN, lower alkyl, substituted lower alkyl, lower alkenyl, lower alkynyl, —SH, —SCH3, alkoxycarbonyl, alkylcarbonylamino, —NHC(O)—O-lower alkyl, —NHC(O)—O-lower alkenyl, —NHC(O)—O-lower alkynyl, —NHCO-cyclopropyl, —NHCO— haloalkyl, —NHSO2CH3, —NHCSNHCH3, sulfoximine, —CH═NOH, —SOCH3, —SO2CH3, —NHSO2CH3, and —SO2NH2;
- R3 is selected from the group consisting of hydrogen, halide, haloalkyl, hydroxyl, amino, methylamino, —CH2OH, methoxy, lower alkyl, lower alkenyl, lower alkynyl, acyloxy, alkylcarbonylamino, —C(O)OCH3, nitrile, and —CH2CN;
- R4 is selected from the group consisting of lower alkyl, substituted lower alkyl, lower alkenyl, substituted lower alkenyl, lower alkynyl, substituted lower alkynyl, alkoxy, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkyl ether, alkylthio, alkenylthio, alkynylthio, thioalkyl ether;
- R8 and R9 are independently selected from the group consisting of hydrogen, lower alkyl, substituted lower alkyl, lower alkenyl, and cycloalkyl, or pharmaceutically acceptable salts, solvates, or prodrugs thereof;
- provided that R2 is not methoxy when R1 is methoxy, R3 is hydrogen, and R4 is 2-propenyl.
3 more elements
A compound selected from the group consisting of:
- or enantiomers thereof, or pharmaceutically acceptable salts, or solvates thereof.
A compound selected from the group consisting of:
- or enantiomers thereof, or pharmaceutically acceptable salts, or solvates thereof.
A compound selected from the group consisting of:
- or enantiomers thereof, or pharmaceutically acceptable salts, or solvates thereof.
A compound selected from the group consisting of:
- or enantiomers thereof, or pharmaceutically acceptable salts, or solvates thereof.
A compound selected from the group consisting of:
- or pharmaceutically acceptable salts, or solvates thereof, wherein the compound is the (+)-enantiomer.
A compound selected from the group consisting of:
- 6-allyl-7a-(1-(2-fluoro-4-methoxyphenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5 (6H)-one,
- 6-allyl-7a-(1-(2-fluoro-5-hydroxy-4-methoxyphenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one,
- 6-allyl-7a-(1-(2,5-difluoro-4-methoxyphenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5 (6H)-one,
- 6-allyl-7a-(1-(2,5-difluoro-4-(methylamino)phenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one,
- 7a-(1-(2-fluoro-4-methoxyphenyl)propan-2-yl)-7,7a-dihydro-6-propylbenzo[d][1,3]dioxol-5 (6H)-one,
- 7a-(1-(2-fluoro-5-hydroxy-4-methoxyphenyl)propan-2-yl)-7,7a-dihydro-6-propylbenzo[d][1,3]dioxol-5(6H)-one,
- 7a-(1-(2,5-difluoro-4-methoxyphenyl)propan-2-yl)-7,7a-dihydro-6-propylbenzo[d][1,3]dioxol-5(6H)-one,
- 7a-(1-(2,5-difluoro-4-(methylamino)phenyl)propan-2-yl)-7,7a-dihydro-6-propylbenzo[d][1,3]dioxol-5(6H)-one,
- 6-(but-3-en-2-yl)-7a-(1-(2-fluoro-4-methoxyphenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one,
- 6-(but-3-en-2-yl)-7a-(1-(2-fluoro-5-hydroxy-4-methoxyphenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one,
- 6-(but-3-en-2-yl)-7a-(1-(2,5-difluoro-4-methoxyphenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one,
- 6-(but-3-en-2-yl)-7a-(1-(2,5-difluoro-4-(methylamino)phenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one, or
- pharmaceutically acceptable salts, or solvates thereof.
10 more elements
A compound according to the formula:
- or stereoisomers thereof, wherein R1 is selected from the group consisting of methoxy, ethoxy, —SCH3, —NHCH3, and —N(CH3)2;
- R2 is selected from the group consisting of hydrogen, hydroxyl, methoxy, ethoxy, amino, aminoalkyl, aminoalkenyl, fluoro, chloro, aminocarbonyl, hydroxyaminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, acetoxy, nitrile, lower alkyl, lower alkenyl, lower alkynyl, alkoxycarbonyl, and alkylcarbonylamino;
- R3 is selected from the group consisting of hydrogen, fluoro, chloro, lower alkyl, lower alkenyl, haloalkyl, acetoxy, —C(O)OCH3, nitrile, and —CH2CN;
- R4 is selected from the group consisting of lower alkyl, substituted lower alkyl, lower alkenyl, substituted lower alkenyl, lower alkynyl, substituted lower alkynyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkyl ether, and thioalkyl ether;
- R6 is selected from the group consisting of hydrogen, halide, methoxy, ethoxy, methyl, ethyl, propyl, nitrile, and acetoxy;
- R7 is selected from the group consisting of hydrogen, halide, hydroxyl, amino, methoxy, ethoxy, methyl, ethyl, propyl, nitrile, and acetoxy, or pharmaceutically acceptable salts, or solvates thereof;
- provided that when R2 is hydrogen R3 is not hydrogen and only one of either R6 or R7 are hydrogen;
- R2, R3, R6, and R7 are all not hydrogen;
- and R2 is not methoxy when R1 is methoxy, R3, R5, and R6 are hydrogen, and R4 is 2-propenyl.
6 more elements
A compound having the chemical structure:
- or stereoisomers thereof, or pharmaceutically acceptable salts and solvates thereof.
A compound having the chemical structure:
- or stereoisomers thereof, or pharmaceutically acceptable salts and solvates thereof.
A compound according to the formula:
- or enantiomers thereof, wherein R2 is selected from the group consisting of —NHCO—C1—O5 alkyl, —NHCO—C2—O5 alkenyl, —NHC(O)—O—C1-C5 alkyl, —NHC(O)—O—C2—O5 alkenyl, and said alkyl and alkenyl groups may be optionally substituted by independent replacement of one, two, or three hydrogen atoms thereon with substituents selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, gem-dimethyl, cyclopropyl, oxo, sulfoxide, acetoxy, hydroxyl, halide, CF3, CCl3, nitrile, amino, methylamino, dimethylamino, ethylamino, diethylamino, tert-butylamino, aminocarbonyl, methylaminocarbonyl, methylcarbonylamino, —CH═NOH, —COOH, —SOCH3, —SO2CH3, —NHSO2CH3, —SO2NH2, —C(O)OCH3, —C(O)CH3, —SH, —SCH3, and —SCH2CH3;
- R3 is selected from the group consisting of hydrogen and fluoro;
- R4 is selected from the group consisting of lower alkyl, substituted lower alkyl, lower alkenyl, substituted lower alkenyl, lower alkynyl, substituted lower alkynyl, alkyl ether, and thioalkyl ether, or pharmaceutically acceptable salts, solvates, or prodrugs thereof.
Dependencies are inferred from the claim text.