US 9,012,424 B2Granted

Nanogels

Assignee20MED Therapeutics B.V.

InventorsJohannes Franciscus Joseph Engbersen, Arkadi Vladimirovich Zinchenko

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Abstract

The present invention relates to a polymer according to Formulas (1) or (2): The present invention further relates to nanogels and nanoparticles made of a polymer according to general Formulas (1) and (2). The nanogels may comprise a biologically active component such as siRNA, miRNA, DNA, an (oligo)peptide or a proteins.

Claims18

Dependent claims

A PA polymer according to Formula (1) or (2):

wherein:
A is independently selected from a direct carbon-carbon single bond, O, N(R1) and S;
R1 is independently selected from H and CH3;
R2 is independently selected from the group consisting of:
(a) C1-C40 alkylene, wherein the alkylene group may be linear or branched and is optionally substituted and/or is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the alkylene group is interrupted by one or more —S—S— groups;
(b) C3-C40 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the cycloalkylene group is interrupted by one or more —S—S— groups outside the ring;
(c) C6-C40 arylene, wherein the arylene group is optionally substituted;
(d) C6-C40 heteroarylene, wherein the heteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C40 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylarylene group is interrupted by one or more —S—S— groups;
(f) C7-C40 alkylheteroarylene, wherein the alkylheteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylheteroarylene group is interrupted by one or more —S—S— groups;
and
(g) a group wherein two C7-C40 (hetero)arylene groups and/or C7-C40 alkyl(hetero)arylene groups are connected to each other by a —S—S— group, wherein the alkyl part of the alkyl(hetero)arylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R3 is independently selected from the group consisting of:
(a) H;
(b) C1-C10 alkyl, wherein the alkyl group may be linear or branched and is optionally substituted and/or is optionally unsaturated and/or is optionally interrupted by one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(C) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally unsaturated and/or optionally comprises one, two or three heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C12 aryl, wherein the aryl group is optionally substituted;
(e) C6-C12 heteroaryl, wherein the heteroaryl group comprises one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and wherein the heteroaryl group is optionally substituted;
(f) C7-C14 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C14 alkylheteroaryl, wherein the alkylheteroaryl group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R4 is independently selected from the group consisting of:
(a) H;
(b) C1-C10 alkyl, wherein the alkyl group may be linear or branched;
(C) C3-C12 cycloalkyl;
(d) C6-C14 aryl;
(e) C6-C14 heteroaryl, wherein the alkylheteroaryl group comprises one, two or three heteroatoms independently selected from O, N and S;
(f) C7-C14 alkylaryl;
and
(g) C7-C14 alkylheteroaryl, wherein the alkylheteroaryl group comprises one, two or three heteroatoms independently selected from O, N and S;
R5 is independently selected from the group consisting of:
(a) C1-C12 alkylene, wherein the alkylene group may be linear or branched and is optionally substituted and/or is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S:
(b) C3-C12 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(c) C6-C12 arylene, wherein the arylene group is optionally substituted;
(d) C6-C12 heteroarylene, wherein the heteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C12 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(f) C7-C12 alkylheteroarylene, wherein the alkylheteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
POL represents a polymeric core having a weight average molecular weight Mw of about 300 to about 25000;
a=2-64;
and
b=1-50.

39 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/122,668Filed 25 May 2012 · us provisional application
Priority: EP 1116788527 May 2011
Published: US 2014/0135376 A115 May 2014
Granted: 21 Apr 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification17 codes

A61K 47/34
Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates: macromolecular compounds obtained otherwise than by reactions only…
A61K 9/06
Medicinal preparations characterised by special physical form: ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
A61K 31/713
Compounds having three or more nucleosides or nucleotides: double-stranded nucleic acids or oligonucleotides
A61K 47/6903
The conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit: the form being…

Family

Application61/490,674Us provisional application · filed 27 May 2011
US 2014/0135376 A1Pre-grant publication · published 15 May 2014
US 9,012,424 B2This patent

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

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Abstract

A PA polymer according to Formula (1) or (2):

wherein:
A is independently selected from a direct carbon-carbon single bond, O, N(R1) and S;
R1 is independently selected from H and CH3;
R2 is independently selected from the group consisting of:
(a) C1-C40 alkylene, wherein the alkylene group may be linear or branched and is optionally substituted and/or is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the alkylene group is interrupted by one or more —S—S— groups;
(b) C3-C40 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S, and/or wherein the cycloalkylene group is interrupted by one or more —S—S— groups outside the ring;
(c) C6-C40 arylene, wherein the arylene group is optionally substituted;
(d) C6-C40 heteroarylene, wherein the heteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C40 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylarylene group is interrupted by one or more —S—S— groups;
(f) C7-C40 alkylheteroarylene, wherein the alkylheteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and/or wherein an alkyl part of the alkylheteroarylene group is interrupted by one or more —S—S— groups;
and
(g) a group wherein two C7-C40 (hetero)arylene groups and/or C7-C40 alkyl(hetero)arylene groups are connected to each other by a —S—S— group, wherein the alkyl part of the alkyl(hetero)arylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R3 is independently selected from the group consisting of:
(a) H;
(b) C1-C10 alkyl, wherein the alkyl group may be linear or branched and is optionally substituted and/or is optionally unsaturated and/or is optionally interrupted by one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
(C) C3-C12 cycloalkyl, wherein the cycloalkyl group is optionally substituted and/or is optionally unsaturated and/or optionally comprises one, two or three heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(d) C6-C12 aryl, wherein the aryl group is optionally substituted;
(e) C6-C12 heteroaryl, wherein the heteroaryl group comprises one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S, and wherein the heteroaryl group is optionally substituted;
(f) C7-C14 alkylaryl wherein the alkylaryl group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(g) C7-C14 alkylheteroaryl, wherein the alkylheteroaryl group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one, two or three heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
R4 is independently selected from the group consisting of:
(a) H;
(b) C1-C10 alkyl, wherein the alkyl group may be linear or branched;
(C) C3-C12 cycloalkyl;
(d) C6-C14 aryl;
(e) C6-C14 heteroaryl, wherein the alkylheteroaryl group comprises one, two or three heteroatoms independently selected from O, N and S;
(f) C7-C14 alkylaryl;
and
(g) C7-C14 alkylheteroaryl, wherein the alkylheteroaryl group comprises one, two or three heteroatoms independently selected from O, N and S;
R5 is independently selected from the group consisting of:
(a) C1-C12 alkylene, wherein the alkylene group may be linear or branched and is optionally substituted and/or is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S:
(b) C3-C12 cycloalkylene, wherein the cycloalkylene group is optionally substituted and/or is optionally unsaturated and/or optionally comprises one or more heteroatoms in the ring, wherein the heteroatoms are independently selected from O, N and S;
(c) C6-C12 arylene, wherein the arylene group is optionally substituted;
(d) C6-C12 heteroarylene, wherein the heteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the heteroarylene group is optionally substituted;
(e) C7-C12 alkylarylene wherein the alkylarylene group is optionally substituted and/or wherein an alkyl part of the alkylarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
and
(f) C7-C12 alkylheteroarylene, wherein the alkylheteroarylene group comprises one, two or three heteroatoms independently selected from O, N and S and/or wherein the alkylheteroarylene group is optionally substituted, and/or wherein an alkyl part of the alkylheteroarylene group is linear or branched and is optionally unsaturated and/or is optionally interrupted by one or more heteroatoms, wherein the heteroatoms are independently selected from O, N and S;
POL represents a polymeric core having a weight average molecular weight Mw of about 300 to about 25000;
a=2-64;
and
b=1-50.

39 more elements

Facts

Application

14/122,668Filed 25 May 2012 · us provisional application

Priority

EP 1116788527 May 2011

Published

US 2014/0135376 A115 May 2014

Granted

21 Apr 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification17 codes

A61K 47/34
Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates: macromolecular compounds obtained otherwise than by reactions only…
A61K 9/06
Medicinal preparations characterised by special physical form: ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
A61K 31/713
Compounds having three or more nucleosides or nucleotides: double-stranded nucleic acids or oligonucleotides
A61K 47/6903
The conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit: the form being…