IP Library › Patent Application 16348433
Patent Application
App. No. 16/348,433

MITOMYCIN C PRODRUG LIPOSOME FORMULATIONS AND USES THEREOF

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Patent No.
US None
App. No.
16/348,433
Abstract

The present invention provides MMC prodrug compounds and liposomal MMC prodrugs and compositions thereof for the treatment of cancer. The compositions include liposomes containing a phosphatidylcholine lipid, a sterol, a PEG-lipid and a MMC prodrug. The present invention also provides liposomal compositions for the treatment of cancer comprising administering to a patient in need thereof a liposome, wherein the liposome comprises: a phosphatidylcholine lipid; a sterol; a PEG-lipid and a MMC prodrug or a pharmaceutically-acceptable salt thereof.

Claims (32)

1 . A compound having the formula:

wherein R and R′ are independently selected from the group consisting of: an alkyl and alkylaryl;

X is selected from the group consisting of: S, Se, and O; and

Y is selected from the group consisting of: a piperadinyl, a piperazinyl, a pyridinyl, dimethylamino, diethylamino, dipropylamino, morpholino, HO—CH 2 CH 2 NH—, (HO—CH 2 CH 2 ) 2 N—, HO—CH 2 CH 2 —N(Me)—, C 6 H 4 CH 2 NH—, and C 6 H 4 CH 2 N(Me).

2 . A compound having the formula selected from the group consisting of:

or a pharmaceutical salt thereof.

3 . (canceled)

4 . (canceled)

5 . A liposomal composition comprising:

i) a liposome comprising:

a) a phosphatidylcholine lipid,

b) a sterol,

c) a PEG-lipid, and

d) a MMC prodrug; and

ii) a pharmaceutically acceptable excipient;

wherein the MMC prodrug is a compound having the formula:

wherein R and R′ are independently selected from the group consisting of: an alkyl and alkylaryl;

X is selected from the group consisting of: S, Se, and O; and

Y is selected from the group consisting of: a piperadinyl, a piperazinyl, a pyridinyl, dimethylamino, diethylamino, dipropylamino, morpholino, HO—CH 2 CH 2 NH—, (HO—CH 2 CH 2 ) 2 N—, HO—CH 2 CH 2 —N(Me)—, C 6 H 4 CH 2 NH—, and C 6 H 4 CH 2 N(Me).

6 . The liposomal composition of claim 5 , wherein the MMC prodrug is selected from the group consisting of:

or a pharmaceutical salt thereof.

7 . A method of preparing a liposomal MMC prodrug, the method comprising:

a) forming a first liposome having a lipid bilayer comprising a phosphatidylcholine lipid and a sterol, wherein the lipid bilayer encapsulates an interior compartment comprising an aqueous solution; and

b) loading the first liposome with a MMC prodrug, or a pharmaceutically acceptable salt, to form a loaded liposome;

wherein the MMC prodrug is a compound having the formula:

wherein R and R′ are independently selected from the group consisting of: an alkyl and alkylaryl;

X is selected from the group consisting of: S, Se, and O; and

Y is selected from the group consisting of: a piperadinyl, a piperazinyl, a pyridinyl, dimethylamino, diethylamino, dipropylamino, morpholino, HO—CH 2 CH 2 NH—, (HO—CH 2 CH 2 ) 2 N—, HO—CH 2 CH 2 —N(Me)—, C 6 H 4 CH 2 NH—, and C 6 H 4 CH 2 N(Me);

thereby forming the liposomal MMC prodrug.

8 . (canceled)

9 . The method of claim 7 , wherein the interior compartment of the first liposome further comprises a thiol-containing compound.

10 . The method of claim 9 , wherein the MMC prodrug and thiol-containing compound undergo a disulfide exchange resulting in a MMC prodrug conjugate.