US 2022/0117930 A2Published application

Medicinal use of serrulatane diterpenes

AssigneeThe University of Sydney

InventorsColin Charles DUKE, Rujee Kyokajee DUKE, Van Hoan TRAN

Life of this patent

Estimating the term…

Abstract

The present disclosure is drawn to methods of treating diseases or disorders, and uses of preparing medicaments. The methods of administering and/or preparation of medicaments can include the use of a compound of Formula (I) disclosed herein, or a geometric isomer, stereoisomer, and/or pharmaceutically acceptable salt or solvate thereof.

Claims35

Dependent claims

A method of treating a disease or disorder, the method comprising administering a therapeutically effective amount of a compound according to a compound of Formula (I),

a geometric isomer, stereoisomer, pharmaceutically acceptable salt or solvate thereof,
wherein:
(i) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC1-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl, OC(O)C4-5alkadienyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl, OC(O)C4-5alkadienyl or ═O;
R3 is independently H, OH, OC1-5alkyl or OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or OC(O)C4-5alkadienyl;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or OC(O)C4-5alkadienyl;
and
A - - - B is CH═C or CH2—CH,
or
(ii) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC(O)C1-5alkyl, OC(O)Ph or OC(O)C2-5 alkenyl;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC(O)C1-5alkyl, OC(O)Ph or OC(O)C2-5alkenyl;
and
A - - - B is CH═C or CH2—CH,
or
(iii) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl, OC(O)Ph or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl, OC(O)Ph or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
and
A - - - B is CH═C or CH2—CH,
or
(iv) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(v) X is CH2;
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(vi) X is CHOH;
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(vii) X is C(O);
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH.

68 more elements

Use of a compound according to Formula (I) in the preparation of a medicament for treating a disease or disorder, wherein formula (I) is

a geometric isomer, stereoisomer, pharmaceutically acceptable salt or solvate thereof,
wherein:
(i) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl, OC(O)C4-5alkadienyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl, OC(O)C4-5alkadienyl or ═O;
R3 is independently H, OH, OC1-5alkyl or OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or OC(O)C4-5alkadienyl;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or OC(O)C4-5alkadienyl;
and
A - - - B is CH═C or CH2—CH,
or
(ii) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC(O)C1-5alkyl, OC(O)Ph or OC(O)C2-5alkenyl;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC(O)C1-5alkyl, OC(O)Ph or OC(O)C2-5alkenyl;
and
A - - - B is CH═C or CH2—CH,
or
(iii) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl, OC(O)Ph or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl, OC(O)Ph or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
and
A - - - B is CH═C or CH2—CH,
or
(iv) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(v) X is CH2;
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(vi) X is CHOH;
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(vii) X is C(O);
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH.

68 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/123,539Filed 16 Dec 2020
Priority: 5 Mar 2019
Published: 21 Apr 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification33 codes

A61K 31/122
Ketones: having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
A61K 31/05
Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates: phenols
A61K 31/085
Ethers or acetals: having an ether linkage to aromatic ring nuclear carbon
A61K 31/216
Of carboxylic acids: of acids having aromatic rings, e.g. benactizyne, clofibrate

Family

Application16/330,676Continuation in part · filed 5 Mar 2019
Application17/123,539Continuation in part
US 10,912,742 B2Related patent
US 11,331,299 B2Related patent
US 2019/0282514 A1Published application
US 2021/0212982 A1Published application
US 2022/0117930 A2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

A method of treating a disease or disorder, the method comprising administering a therapeutically effective amount of a compound according to a compound of Formula (I),

a geometric isomer, stereoisomer, pharmaceutically acceptable salt or solvate thereof,
wherein:
(i) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC1-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl, OC(O)C4-5alkadienyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl, OC(O)C4-5alkadienyl or ═O;
R3 is independently H, OH, OC1-5alkyl or OC(O)C1-5alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or OC(O)C4-5alkadienyl;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC4-5alkadienyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or OC(O)C4-5alkadienyl;
and
A - - - B is CH═C or CH2—CH,
or
(ii) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC2-5 alkenyl, OC(O)C1-5alkyl, OC(O)Ph, OC(O)C2-5alkenyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC(O)C1-5alkyl, OC(O)Ph or OC(O)C2-5 alkenyl;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC2-5alkenyl, OC(O)C1-5alkyl, OC(O)Ph or OC(O)C2-5alkenyl;
and
A - - - B is CH═C or CH2—CH,
or
(iii) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl, OC(O)Ph or ═O;
R2 is independently H, OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl, OC(O)Ph or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
and
A - - - B is CH═C or CH2—CH,
or
(iv) X is CH2, CHOH or C(O);
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
where X is CH2, CHOH or C(O), R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(v) X is CH2;
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(vi) X is CHOH;
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH,
or
(vii) X is C(O);
R1 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R2 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
R3 is independently H, OH, OC1-5alkyl, OC(O)C1-5 alkyl or ═O;
and no more than one of R1, R2 and R3 can be H;
R4 is OH, OC1-5alkyl, OCH2Ph, OC(O)C1-5alkyl or OC(O)Ph;
or X and R3 form a six-membered ether ring or lactone ring, or a six membered ring containing a hemiacetal carbon atom or an acetal carbon atom wherein R4 is respectively OH or OC1-5alkyl or OC(O)C1-5alkyl;
and
A - - - B is CH═C or CH2—CH.

68 more elements

Facts

Application

17/123,539Filed 16 Dec 2020

Priority

5 Mar 2019

Published

21 Apr 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification33 codes

A61K 31/122
Ketones: having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
A61K 31/05
Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates: phenols
A61K 31/085
Ethers or acetals: having an ether linkage to aromatic ring nuclear carbon
A61K 31/216
Of carboxylic acids: of acids having aromatic rings, e.g. benactizyne, clofibrate

Family

Application16/330,676Continuation in part · filed 5 Mar 2019

Application17/123,539Continuation in part

US 10,912,742 B2Related patent

US 11,331,299 B2Related patent

US 2019/0282514 A1Published application

US 2021/0212982 A1Published application

US 2022/0117930 A2This patent

From the US filing history. Foreign family members aren’t listed.