US RE49,741 E1
Drug delivery system for administration of poorly water soluble pharmaceutically active substances
Julian Aleksov, Lidingo (SE); and Igor Lokot, Uppsala (SE)
Assigned to Vivesto AB, Uppsala (SE)
Filed by Vivesto AB, Uppsala (SE)
Filed on Jun. 12, 2020, as Appl. No. 16/899,848.
Application 14/633,177 is a continuation of application No. 12/809,252, granted, now 8,999,382, issued on Apr. 7, 2015, previously published as PCT/SE2008/051515, filed on Dec. 18, 2008.
Application 16/899,848 is a reissue of application No. 14/633,177, filed on Feb. 27, 2015, granted, now 9,993,438, issued on Jun. 12, 2018.
Claims priority of application No. PCT/SE2007/001127 (WO), filed on Dec. 19, 2007.
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 9/51 (2006.01); A61K 9/14 (2006.01); A61K 31/337 (2006.01); A61K 38/13 (2006.01)
CPC A61K 9/5123 (2013.01) [A61K 9/145 (2013.01); A61K 31/337 (2013.01); A61K 38/13 (2013.01)] 23 Claims
 
[ 6. A drug delivery system comprising nanoparticles formed of a combination of a sodium salt of the methyl ester of N-all-trans-retinoyl cysteic acid and a sodium salt of the methyl ester of N-13-cis-retinoyl cysteic acid, and paclitaxel, wherein the nanoparticles are essentially amorphous and have an effective average particle size of about 8-30 nm;
wherein the weight ratio of sodium salt of the methyl ester of N-all-trans-retinoyl cysteic acid to sodium salt of methyl ester of N-13-cis-retinoyl cysteic acid is about 1:1;
wherein a weight-to-weight ratio of said combination of sodium salt of the methyl ester of N-all-trans-retinoyl cysteic acid and sodium salt of the methyl ester of N-13-cis-retinoyl cysteic acid, to paclitaxel is in the range from 1:1 to 1.5:1,
wherein the nanoparticles are prepared by a method which comprises the steps of:
providing a solution of a combination of sodium salt of the methyl ester of N-all-trans-retinoyl cysteic acid and a sodium salt of the methyl ester of N-13-cis-retinoyl cysteic acid;
adding an organic solution of paclitaxel to said solution;
and evaporating the resulting solution, leaving the nanoparticles in essentially amorphous form. ]