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US 9,717,801 B2Granted
Glycogen-based cationic polymers
AssigneeAziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A.
InventorsVincenzo Russo, Elisa Liberati, Nicola Cazzolla
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Abstract
The present invention relates to glycogen-based cationic polymers, to complexes of the said cationic polymers with anionic compounds, to pharmaceutical compositions comprising the said complexes, and to the use of the said complexes for delivering or transfecting the said anionic compounds to a specific pharmacological target, such as, for instance an organ, a tissue or a cell.
Claims17
A glycogen-based cationic polymer, which is a polymer comprising at least one repeating unit selected from the group consisting of (a) and (b):
- in which
- groups R, which may be identical or different, are a hydrogen atom, a carboxymethyl group, optionally in salt form with a pharmaceutically acceptable organic or inorganic base, or a group selected from the group consisting of NH2—(C1-C6)alkyl, [N,N-di(C1-C6)alkylamino]-(C1-C6)alkyl, NH2—{[(C1-C6)alkyl-di(C1-C6)alkylammonio]}-(C1-C6) alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonio}-(C1-C6)alkyl, NH2—[(C1-C6)alkylamino]-(C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1-C6)alkyl, [tri(C1-C6)alkylammonio]-(C1-C6)alkyl, and azocyclyl-(C1-C6)alkyl, in which said (C1-C6)alkyl chains, which may be identical or different, are optionally substituted with one or more hydroxyl groups, and
- n is an integer greater than or equal to 1;
- and
- in which
- R1 is a hydrogen atom, a carboxymethyl group, optionally in salt form with a pharmaceutically acceptable organic or inorganic base, or a group comprising nitrogen selected from the group consisting of:
- NH2—(C1-C6)alkyl, [N,N-di(C1-C6)-alkylamino]-(C1-C6)alkyl, NH2—[(C1-C6)alkyl-di(C1-C6)alkylammonio]-(C1-C6)-alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonio}-(C1-C6)alkyl, NH2—[(C1-C6)alkylamino]-(C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1-C6)alkyl, and [tri(C1-C6)alkylammonio]-(C1-C6)-alkyl, in which said (C1-C6)alkyl chains, which may be identical or different, are optionally substituted with one or more hydroxyl groups;
- X1 and X2, which may be identical or different, are a group —OH or a group —NHR2, in which R2 is selected from the group consisting of:
- a hydrogen atom, (C1-C6)alkyl, and H—[NH—(C1-C6)alkyl]p-, where p is an integer greater than or equal to 1 and said groups (C1-C6)alkyl may be identical or different;
- and
- m is an integer greater than or equal to 1;
- with the provisos that
- at least one group from among R, R1, X1 and X2 is a group containing nitrogen, and
- the glycogen-based cationic polymer is different from a product obtained by reacting glycogen with N-(3-chloro-2-hydroxypropyl)-trimethyl ammonium chloride.
11 more elements
A pharmaceutical composition comprising:
- (A) a complex between (1) a glycogen-based cationic polymer, which is a polymer comprising at least one repeating unit chosen from the group consisting of (a) and (b):
- in which
- groups R, which may be identical or different, are a hydrogen atom, a carboxymethyl group, optionally in salt form with a pharmaceutically acceptable organic or inorganic base, or a group selected from the group consisting of NH2—(C1-C6)alkyl, [N,N-di(C1-C6)alkylamino]-(C1-C6)alkyl, NH2—{[(C1-C6)alkyl-di(C1-C6)alkylammonio]}-(C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkyl-di(C1-C6)alkyl-ammonio}-(C1-C6)alkyl, NH2—[(C1-C6)alkylamino]-(C1-C6)alkyl, {[N,N-di-(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1-C6)alkyl, [tri(C1-C6)alkyl-ammonio]-(C1-C6)alkyl, and azocyclyl-(C1-C6)alkyl, in which said (C1-C6)alkyl chains, which may be identical or different, are optionally substituted with one or more hydroxyl groups, and
- n is an integer greater than or equal to 1;
- and
- in which
- R1 is a hydrogen atom, a carboxymethyl group, optionally in salt form with a pharmaceutically acceptable organic or inorganic base, or a group selected from the group consisting of:
- NH2—(C1-C6)alkyl, [N,N-di(C1-C6) alkylamino]-(C1-C6)alkyl, NH2—[(C1-C6)alkyl-di(C1-C6)alkylammonio]-(C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkyl-di(C1-C6)alkylammonio}-(C1-C6)alkyl, NH2—[(C1-C6)alkylamino]-(C1-C6)alkyl, {[N,N-di(C1-C6)alkylamino]-(C1-C6)alkylamino}-(C1-C6)alkyl, and [tri(C1-C6)alkylammonio]-(C1-C6)-alkyl, in which said (C1-C6)alkyl chains, which may be identical or different, are optionally substituted with one or more hydroxyl groups;
- X1 and X2, which may be identical or different, are a group —OH or a group —NHR2, in which R2 is selected from the group consisting of:
- a hydrogen atom, (C1-C6)alkyl, and H—[NH—(C1-C6)alkyl]p-, where p is an integer greater than or equal to 1 and the groups (C1-C6)alkyl may be identical or different;
- and
- m is an integer greater than or equal to 1;
- at least one group from among R, R1, X1 and X2 is a group comprising nitrogen,
- and (2) an anionic compound;
- and
- (B) at least one pharmaceutically acceptable excipient.
13 more elements
Dependencies are inferred from the claim text.