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US 2015/0307429 A1Published application
Prenylated hydroxystilbenes
AssigneeThe University of Sydney
InventorsColin Charles Duke, Van Hoan Tran, Rujee Kyokajee Duke
Life of this patent
Estimating the term…
Abstract
Prenylated stilbene compounds and the use of such compounds in the treatment of diseases and medical disorders, for example cancer, skin ageing, inflammation, bacterial or fungal infection and immunosuppression.
Claims126
1-69. (canceled)
A method for treating cancer comprising administering a therapeutically effective amount of a compound of formula (I),
- wherein:
- R1 is independently H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHCH(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2, wherein at least one of R1 is OH and at least one of R1 is CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHCH(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2 or OCH═CHC(CH3)═CH2;
- R2 is selected from OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHCH(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R3 is selected from H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHCH(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R4 is selected from, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- n is an integer selected from the group consisting of 1, 2, 3 and 4;
- and
- A----B is selected from CH═CH, CH2—CH2, CH═CHX, or CH2—CH2X, where X═(CH2)pCH2, and p is an integer selected from the group consisting of 0, 1, 2 and 3;
- provided that:
- (i) when R2 is OH, R3 is H or OH, A----B is CH═CH, n is 3 and two of the R1 groups are OH located in the meta positions, and the third R1 group is located in the para position, then the third R1 group is not CH═CHCH(CH3)2 or CH2CH═C(CH3)2;
- (ii) when R2 is OH and R3 is H, A---B is CH═CH, n is 4 and two of the R1 groups are CH2CH═C(CH3)2, at least one of the CH2CH═C(CH3)2 groups is not located in an ortho position;
- and
- (iii) when R2 is OH and R3 is H, A---B is CH═CH, n is 3 and one of the R1 groups is CH2CH═C(CH3)2, the CH2CH═C(CH3)2 group is not located in an ortho position;
- or pharmaceutically acceptable salts, solvates, or a pharmaceutical composition including said compounds, to a patient in need thereof.
11 more elements
A method for treating cancer comprising administering a therapeutically effective amount of a compound of formula (I),
- wherein:
- R1 is independently H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2, wherein at least one of R1 is OH and at least one of R1 is CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R2 is selected from OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R3 is selected from OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R4 is selected from, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- n is an integer selected from the group consisting of 1, 2, 3 and 4;
- and
- A----B is selected from CH═CH, CH2—CH2, CH═CHX, or CH2—CH2X, where X═(CH2)pCH2, and p is an integer selected from the group consisting of 0, 1, 2 and 3;
- or pharmaceutically acceptable salts, solvates, or a pharmaceutical composition including said compound, to a patient in need thereof.
6 more elements
A method for treating cancer comprising administering a therapeutically effective amount of a compound of formula (Ia),
- wherein:
- R1a, R1b, R1c and R1d are each independently H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHCH(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2, wherein at least one of R1a-1d is OH and at least one of R1a-1d is CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHCH(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2 or OCH═CHC(CH3)═CH2;
- R2 is selected from OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R3 is selected from H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R4 is selected from, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- and
- A----B is selected from CH═CH, CH2—CH2, CH═CHX, or CH2—CH2X, where X═(CH2)pCH2, and p is an integer selected from the group consisting of 0, 1, 2 and 3;
- provided that:
- (i) when R2 is OH, R3 is H or OH, A----B is CH═CH, R1a is H, R1b and R1d are OH, then R1c is not CH═CHCH(CH3)2 or CH2CH═C(CH3)2;
- or pharmaceutically acceptable salts, solvates, or a pharmaceutical composition including said compounds, to a patient in need thereof.
7 more elements
A method for treating cancer comprising administering a therapeutically effective amount of a compound of formula (Ia),
- wherein:
- R1a, R1b, R1c and R1d are each independently H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2, wherein at least one of R1a-1d is OH and at least one of R1a-1d is CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2 or OCH═CHC(CH3)═CH2;
- R2 is selected from OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R3 is selected from OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R4 is selected from, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- and
- A----B is selected from CH═CH, CH2—CH2, CH═CHX, or CH2—CH2X, where X═(CH2)pCH2, and p is an integer selected from the group consisting of 0, 1, 2 and 3;
- or pharmaceutically acceptable salts, solvates, or a pharmaceutical composition including said compounds, to a patient in need thereof.
5 more elements
A method according to claim 23, wherein the cancer is leukemia.
A method according to claim 23, wherein the cancer is melanoma.
A method for treating cancer comprising administering a therapeutically effective amount of a compound of formula (Ia),
- wherein:
- R1a and R1c are each independently selected from H or CH2CH═C(CH3)2;
- R1b is selected from OH, OCH3 or OCH2CH═C(CH3)2;
- R1d is OH;
- wherein at least one of R1a or R1c is CH2CH═C(CH3)2 and/or R1b is OCH2CH═C(CH3)2;
- R2 is selected from OH or OCH3;
- R3 is selected from H, OH or OCH3;
- and A----B is CH═CH;
- provided that:
- (i) when R2 is OH, R3 is H or OH, R1a is H, R1c is CH═CHCH(CH3)2, then R1b is not OH;
- or pharmaceutically acceptable salts, solvates, or a pharmaceutical composition including said compounds, to a patient in need thereof.
8 more elements
A method for treating cancer comprising administering a therapeutically effective amount of a compound of formula (Ia),
- wherein:
- R1a and R1c are each independently selected from H or CH2CH═C(CH3)2;
- R1b is selected from OH, OCH3 or OCH2CH═C(CH3)2;
- R1d is OH;
- wherein at least one of R1a or R1c is CH2CH═C(CH3)2 and/or R1b is OCH2CH═C(CH3)2;
- R2 is selected from OH or OCH3;
- R3 is selected from OH or OCH3;
- and A----B is CH═CH;
- or pharmaceutically acceptable salts, solvates, or a pharmaceutical composition including said compounds, to a patient in need thereof.
6 more elements
A compound of formula (Ia)
- or pharmaceutically acceptable salts or solvates thereof, wherein:
- R1a is selected from, H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R1b is selected from, H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R1c is selected from H, OH, OR4a, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R1d is selected from H, OH, OR4a, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- wherein at least one of R1a-1d is OH and at least one of R1a-1d is CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R2 is selected from OH, OR4, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R3 is selected from H, OH, OR4, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R4 is selected from, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- R4a is selected from, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- and
- A----B is selected from CH═CH, CH═CHX, or —CH2—CH2X, where X═(CH2)pCH2 and p is an integer selected from the group consisting of 0, 1, 2 and 3;
- provided that:
- (i) when R3 is H and R2 is OH or OCH2CH═C(CH3)2, then R1b and R1d are independently not OH or OCH2CH═C(CH3)2;
- (ii) when R3 is H, one of R1a-1d is H and at least one of R1a-1d is CH2CH═C(CH3)2, then A---B is not CH═CH.
- (iii) when R2 is OH, R3 is H or OH, A----B is CH═CH, R1a is H, R1b and R1d are OH, then R1c is not CH═CHCH(CH3)2 or CH2CH═C(CH3)2;
13 more elements
A compound of formula (Ia)
- or pharmaceutically acceptable salts or solvates thereof, wherein:
- R1a is selected from, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- le is selected from, H, OH, OR4, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R1c is selected from H, OH, OR4a, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R1d is selected from H, OH, OR4a, CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- wherein at least one of R1a-1d is OH and at least one of R1a-1d is CH2CH═C(CH3)2, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R2 and R3 are each independently selected from OH, OR4, OCH2CH═C(CH3)2, CH═CHC(CH3)═CH2, OCH═CHCH(CH3)2, or OCH═CHC(CH3)═CH2;
- R4 is selected from, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- R4a is selected from, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl or benzyl;
- and
- A----B is selected from CH═CH, CH═CHX, or —CH2—CH2X, where X═(CH2)pCH2 and p is an integer selected from the group consisting of 0, 1, 2 and 3.
8 more elements
A compound of formula (Ia)
- or pharmaceutically acceptable salts or solvates thereof, wherein:
- R1a and R1c are each independently selected from H or CH2CH═C(CH3)2;
- R1b is selected from OH, OCH3 or OCH2CH═C(CH3)2;
- R1d is OH;
- wherein at least one of R1a or R1c is CH2CH═C(CH3)2 and/or R1b is OCH2CH═C(CH3)2;
- R2 is selected from OH or OCH3;
- R3 is selected from H, OH or OCH3;
- and A----B is CH═CH;
- provided that:
- (i) when R2 is OH, R3 is H or OH,88 R1a is H, R1c is CH═CHCH(CH3)2, then R1b is not OH.
7 more elements
A compound of formula (Ia)
- or pharmaceutically acceptable salts or solvates thereof, wherein:
- R1a is CH2CH═C(CH3)2;
- R1b is selected from OH, OCH3 or OCH2CH═C(CH3)2;
- R1c is selected from H or CH2CH═C(CH3)2;
- R1d is OH;
- wherein at least one of R1a or R1c is CH2CH═C(CH3)2 and/or R1b is OCH2CH═C(CH3)2;
- R2 is selected from OH or OCH3;
- R3 is selected from H, OH or OCH3;
- and A----B is CH═CH.
6 more elements
A compound according to structure USYDS18:
A compound according to structure USYDS15:
A method of preparing a compound having the formula
- comprising:
- (i) treating the carboxylic acid with a suitable agent to provide the acid chloride as follows;
- (ii) condensation of the corresponding acid chloride with an aryl alkene as follows;
- (iii) deprotection of the acetate group and alkylation as follows:
- wherein, R5 is selected from the group consisting of OEt, OPr, OiPr, OBu, OiBu, OtBu, and OBn;
- and
- R6 and R7 are each independently selected from the group consisting of OMe, OEt, OPr, OiPr, OBu, OiBu, OtBu, and OBn.
4 more elements
Dependencies are inferred from the claim text.