US2016030581A1PendingUtilityA1

Biodegradable drug delivery compositions

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Assignee: MEDINCELLPriority: Dec 29, 2010Filed: Oct 14, 2015Published: Feb 4, 2016
Est. expiryDec 29, 2030(~4.5 yrs left)· nominal 20-yr term from priority
Inventors:Georges Gaudriault
A61P 25/24A61P 25/18A61K 38/26C08L 67/04C08G 63/66A61K 31/167A61K 47/34A61K 31/519A61K 31/485A61K 9/0024A61K 9/0019A61K 47/20A01N 25/10A61K 31/7048A61K 47/50
55
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Claims

Abstract

A biodegradable drug delivery compositions comprising a triblock copolymer containing a polyester and a polyethylene glycol and a diblock copolymer containing a polyester and an end-capped polyethylene glycol, as well as a pharmaceutically active principle is disclosed.

Claims

exact text as granted — not AI-modified
1 . (canceled) 
     
     
         2 . A biodegradable drug delivery composition comprising:
 (a) a biodegradable triblock copolymer having the formula:
   poly(lactic-co-glycolic acid) v -poly(ethylene glycol) w -poly(lactic-co-glycolic acid) x    
   wherein v and x are the number of repeat units ranging from 24 to 682 and w is the number of repeat units ranging from 4 to 273 and v=x or v≠x;   (b) a biodegradable diblock copolymer having the formula:
   methoxy poly(ethylene glycol) y -poly(lactic-co-glycolic acid) z    
   wherein y and z are the number of repeat units, with y ranging from 3 to 45 and z ranging from 7 to 327, wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable CA diblock copolymer of (b) is 1:3 to 1:8 or 1:1 to 1:19 or 3:2 to 1:19 in said biodegradable drug composition, which is insoluble in an aqueous environment; and   (c) at least one pharmaceutically active principle.   
     
     
         3 . A biodegradable drug delivery composition comprising:
 (a) a biodegradable triblock copolymer present in an amount of 3.0% to 45% (w %/w %) of the total composition having the formula:
   poly(lactic-co-glycolic acid) v -poly(ethylene glycol) w -poly(lactic-co-glycolic acid) x    
   wherein v and x are the number of repeat units ranging from 24 to 682 and w is the number of repeat units ranging from 4 to 273, v and x being lactyl or lactoyl repeat units and w being ethylene glycol repeat units and v=x or v≠x;   (b) a biodegradable diblock copolymer present in an amount of 8.0% to 50% (w %/w %) having the formula:
   methoxy poly(ethylene glycol) y -poly(lactic-co-glycolic acid) z    
   wherein y and z are the number of repeat units, with y ranging from 3 to 45 and z ranging from 7 to 327, y being the number of ethylene glycol repeat units and z the number of lactyl or lactoyl repeat units wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable CA diblock copolymer of (b) is 1:3 to 1:8 or 1:1 to 1:19 or 3:2 to 1:19 in said biodegradable drug composition, which is insoluble in an aqueous environment; and   (c) at least one pharmaceutically active principle present in an amount of 1% to 20% (w %/w %) of the total composition.   
     
     
         4 . The biodegradable drug delivery composition according to  claim 2 , wherein said composition is an injectable liquid and forms an implant when injected into the body or are small solid particles or rod implants or spatial formulations. 
     
     
         5 . The biodegradable drug delivery composition according to  claim 2 , wherein the ratio of the biodegrdable triblock copolymer of (a) and the biodegradable diblock copolymer of (b) is selected from the group of 1:1, 1:2, 1:3, 1:4 and 1:5. 
     
     
         6 . The biodegradable drug delivery composition according to  claim 2 , wherein the size of the polyethylene glycol chain ranges from 200 Da to 12 kDa or 194 Da to 12 kDa and the size of the methoxy polyethylene glycol chain ranges from 100 Da to 2 kDa or 164 Da to 2 kDa. 
     
     
         7 . The biodegradable drug delivery composition according to  claim 2 , further comprising a pharmaceutically acceptable vehicle. 
     
     
         8 . The biodegradable drug delivery composition according to  claim 2 , wherein the at least one pharmaceutically active principle is present in an amount of 1% to 20% (w %/w %) of the total composition. 
     
     
         9 . The biodegradable drug delivery composition according to  claim 2 , wherein the copolymers are present in an amount of 20% to 50% (w %/w %) of the total composition. 
     
     
         10 . The biodegradable drug delivery composition according to  claim 2 , wherein the triblock copolymer is present in an amount of 3.0% to 45% (w %/w %) of the total composition. 
     
     
         11 . The biodegradable drug delivery composition according to  claim 2 , wherein the diblock copolymer is present in an amount of 8.0% to 50% (w %/w %) of the total composition. 
     
     
         12 . The biodegradable drug delivery composition according to  claim 2 , wherein the polylactic repeat unit to ethylene oxide molar ratio in the composition is between 0.5 to 3.5 or 0.5 to 22.3 in the triblock and 2 to 6 or 0.8 to 13 in the diblock. 
     
     
         13 . The biodegradable drug composition according to  claim 2 , further comprising an organic solvent selected from the group of benzyl alcohol, benzyl benzoate, dimethyl isosorbide (DMI), dimethyl sulfoxide (DMSO), ethyl acetate, ethyl benzoate, ethyl lactate, glycerol formal, methyl ethyl ketone, methyl isobutyl ketone, N-ethyl-2-pyrrolidone, N-methyl-2-pyrrolidinone (NMP), pyrrolidone-2, tetraglycol, triacetin, tributyrin, tripropionin and mixtures thereof. 
     
     
         14 . The biodegradable drug composition according to  claim 3 , further comprising an organic solvent selected from the group of benzyl alcohol, benzyl benzoate, dimethyl isosorbide (DMI), dimethyl sulfoxide (DMSO), ethyl acetate, ethyl benzoate, ethyl lactate, glycerol formal, methyl ethyl ketone, methyl isobutyl ketone, N-ethyl-2-pyrrolidone, N-methyl-2-pyrrolidinone (NMP), pyrrolidone-2, tetraglycol, triacetin, tributyrin, tripropionin and mixtures thereof. 
     
     
         15 . The biodegradable drug delivery composition according to  claim 14 , wherein said composition is an injectable liquid and forms an implant when injected into the body or are small solid particles or rod implants or spatial formulations. 
     
     
         16 . A biodegradable drug delivery composition comprising:
 (a) a biodegradable triblock copolymer having the formula:
   poly(lactic-co-glycolic acid) v -poly(ethylene glycol) w -poly(lactic-co-glycolic acid) x    
   wherein v and x are the number of repeat units ranging from 24 to 682 and w is the number of repeat units ranging from 4 to 273 and v=x or v≠x;   (b) a biodegradable diblock copolymer having the formula:
   methoxy poly(ethylene glycol) y -poly(lactic acid) z    
   wherein y and z are the number of repeat units, with y ranging from 3 to 45 and z ranging from 7 to 327, wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable CA diblock copolymer of (b) is 1:3 to 1:8 or 1:1 to 1:19 or 3:2 to 1:19 in said biodegradable drug composition, which is insoluble in an aqueous environment; and   (c) at least one pharmaceutically active principle.   
     
     
         17 . A biodegradable drug delivery composition comprising:
 (a) a biodegradable triblock copolymer present in an amount of 3.0% to 45% (w %/w %) of the total composition having the formula:
   poly(lactic-co-glycolic acid) v -poly(ethylene glycol) w -poly(lactic-co-glycolic acid) x    
   wherein v and x are the number of repeat units ranging from 24 to 682 and w is the number of repeat units ranging from 4 to 273, v and x being lactyl or lactoyl repeat units and w being ethylene glycol repeat units and v=x or v≠x;   (b) a biodegradable diblock copolymer present in an amount of 8.0& to 50% (w %/w %) having the formula:
   methoxy poly(ethylene glycol) y -poly(lactic acid) z    
   wherein y and z are the number of repeat units, with y ranging from 3 to 45 and z ranging from 7 to 327, y being the number of ethylene glycol repeat units and z the number of lactyl or lactoyl repeat units wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable CA diblock copolymer of (b) is 1:3 to 1:8 or 1:1 to 1:19 or 3:2 to 1:19 in said biodegradable drug composition, which is insoluble in an aqueous environment; and   (c) at least one pharmaceutically active principle present in an amount of 1% to 20% (w %/w %) of the total composition.   
     
     
         18 . The biodegradable drug delivery composition according to  claim 16 , wherein said composition is an injectable liquid and forms an implant when injected into the body or are small solid particles or rod implants or spatial formulations. 
     
     
         19 . The biodegradable drug delivery composition according to  claim 16 , wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable diblock copolymer of (b) is selected from the group of 1:1, 1:2, 1:3, 1:4 and 1:5. 
     
     
         20 . The biodegradable drug delivery composition according to  claim 16 , wherein the size of the polyethylene glycol chain ranges from 200 Da to 12 kDa or 194 Da to 12 kDa and the size of the methoxy polyethylene glycol chain ranges from 100 Da to 2 kDa or 164 Da to 2 kDa. 
     
     
         21 . The biodegradable drug delivery composition according to  claim 16 , further comprising a pharmaceutically acceptable vehicle. 
     
     
         22 . The biodegradable drug delivery composition according to  claim 16 , wherein the at least one pharmaceutically active principle is present in an amount of 1% to 20% (w %/w %) of the total composition. 
     
     
         23 . The biodegradable drug delivery composition according to  claim 16 , wherein the copolymers are present in an amount of 20% to 50% (w %/w %) of the total composition. 
     
     
         24 . The biodegradable drug delivery composition according to  claim 16 , wherein the triblock copolymer is present in an amount of 3.0% to 45% (w %/w %) of the total composition. 
     
     
         25 . The biodegradable drug delivery composition according to  claim 16 , wherein the diblock copolymer is present in an amount of 8.0% to 50% (w %/w %) of the total composition. 
     
     
         26 . The biodegradable drug delivery composition according to  claim 16 , wherein the polylactic repeat unit to ethylene oxide molar ratio in the composition is between 0.5 to 3.5 or 0.5 to 22.3 in the triblock and 2 to 6 or 0.8 to 13 in the diblock. 
     
     
         27 . The biodegradable drug composition according to  claim 16 , further comprising an organic solvent selected from the group of benzyl alcohol, benzyl benzoate, dimethyl isosorbide (DMI), dimethyl sulfoxide (DMSO), ethyl acetate, ethyl benzoate, ethyl lactate, glycerol formal, methyl ethyl ketone, methyl isobutyl ketone, N-ethyl-2-pyrrolidone, N-methyl-2-pyrrolidinone (NMP), pyrrolidone-2, tetraglycol, triacetin, tributyrin, tripropionin and mixtures thereof. 
     
     
         28 . The biodegradable drug composition according to  claim 17 , further comprising an organic solvent selected from the group of benzyl alcohol, benzyl benzoate, dimethyl isosorbide (DMI), dimethyl sulfoxide (DMSO), ethyl acetate, ethyl benzoate, ethyl lactate, glycerol formal, methyl ethyl ketone, methyl isobutyl ketone, N-ethyl-2-pyrrolidone, N-methyl-2-pyrrolidinone (NMP), pyrrolidone-2, tetraglycol, triacetin, tributyrin, tripropionin and mixtures thereof. 
     
     
         29 . The biodegradable drug delivery composition according to  claim 28 , wherein said composition is an injectable liquid and forms an implant when injected into the body or are small solid particles or rod implants or spatial formulations. 
     
     
         30 . A biodegradable drug delivery composition comprising:
 (a) a biodegradable triblock copolymer having the formula:
   poly(lactic acid) v -poly(ethylene glycol) w -poly(lactic acid) x    
   wherein v and x are the number of repeat units ranging from 24 to 682 and w is the number of repeat units ranging from 4 to 273 and v=x or  14   x;      (b) a biodegradable diblock copolymer having the formula:
   methoxy poly(ethylene glycol) y -poly(lactic-co-glycolic acid) z    
   wherein y and z are the number of repeat units, with y ranging from 3 to 45 and z ranging from 7 to 327, wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable CA diblock copolymer of (b) is 1:3 to 1:8 or 1:1 to 1:19 or 3:2 to 1:19 in said biodegradable drug composition, which is insoluble in an aqueous environment; and   (c) at least one pharmaceutically active principle.   
     
     
         31 . A biodegradable drug delivery composition comprising:
 (a) a biodegradable triblock copolymer present in an amount of 3.0% to 45% (w %/w %) of the total composition having the formula:
   poly(lactic acid) v -poly(ethylene glycol) w -poly(lactic acid) x    
   wherein v and x are the number of repeat units ranging from 24 to 682 and w is the number of repeat units ranging from 4 to 273, v and x being lactyl or lactoyl repeat units and w being ethylene glycol repeat units and v=x or v≠x;   (b) a biodegradable diblock copolymer present in an amount of 8.0& to 50% (w %/w %) having the formula:
   methoxy poly(ethylene glycol) y -poly(lactic-co-glycolic acid) z    
   wherein y and z are the number of repeat units, with y ranging from 3 to 45 and z ranging from 7 to 327, y being the number of ethylene glycol repeat units and z the number of lactyl or lactoyl repeat units wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable CA diblock copolymer of (b) is 1:3 to 1:8 or 1:1 to 1:19 or 3:2 to 1:19 in said biodegradable drug composition, which is insoluble in an aqueous environment; and   (c) at least one pharmaceutically active principle present in an amount of 1% to 20% (w %/w %) of the total composition.   
     
     
         32 . The biodegradable drug delivery composition according to  claim 30 , wherein said composition is an injectable liquid and forms an implant when injected into the body or are small solid particles or rod implants or spatial formulations. 
     
     
         33 . The biodegradable drug delivery composition according to  claim 30 , wherein the ratio of the biodegradable triblock copolymer of (a) and the biodegradable diblock copolymer of (b) is selected from the group of 1:1, 1:2, 1:3, 1:4 and 1:5. 
     
     
         34 . The biodegradable drug delivery composition according to  claim 30 , wherein the size of the polyethylene glycol chain ranges from 200 Da to 12 kDa or 194 Da to 12 kDa and the size of the methoxy polyethylene glycol chain ranges from 100 Da to 2 kDa or 164 Da to 2 kDa. 
     
     
         35 . The biodegradable drug delivery composition according to  claim 30 , further comprising a pharmaceutically acceptable vehicle. 
     
     
         36 . The biodegradable drug delivery composition according to  claim 30 , wherein the at least one pharmaceutically active principle is present in an amount of 1% to 20% (w %/w %) of the total composition. 
     
     
         37 . The biodegradable drug delivery composition according to  claim 30 , wherein the copolymers are present in an amount of 20% to 50% (w %/w %) of the total composition. 
     
     
         38 . The biodegradable drug delivery composition according to  claim 30 , wherein the triblock copolymer is present in an amount of 3.0% to 45% (w %/w %) of the total composition. 
     
     
         39 . The biodegradable drug delivery composition according to  claim 30 , wherein the diblock copolymer is present in an amount of 8.0% to 50% (w %/w %) of the total composition. 
     
     
         40 . The biodegradable drug delivery composition according to  claim 30 , wherein the polylactic repeat unit to ethylene oxide molar ratio in the composition is between 0.5 to 3.5 or 0.5 to 22.3 in the triblock and 2 to 6 or 0.8 to 13 in the diblock. 
     
     
         41 . The biodegradable drug composition according to  claim 30 , further comprising an organic solvent selected from the group of benzyl alcohol, benzyl benzoate, dimethyl isosorbide (DMI), dimethyl sulfoxide (DMSO), ethyl acetate, ethyl benzoate, ethyl lactate, glycerol formal, methyl ethyl ketone, methyl isobutyl ketone, N-ethyl-2-pyrrolidone, N-methyl-2-pyrrolidinone (NMP), pyrrolidone-2, tetraglycol, triacetin, tributyrin, tripropionin and mixtures thereof. 
     
     
         42 . The biodegradable drug composition according to  claim 31 , further comprising an organic solvent selected from the group of benzyl alcohol, benzyl benzoate, dimethyl isosorbide (DMI), dimethyl sulfoxide (DMSO), ethyl acetate, ethyl benzoate, ethyl lactate, glycerol formal, methyl ethyl ketone, methyl isobutyl ketone, N-ethyl-2-pyrrolidone, N-methyl-2-pyrrolidinone (NMP), pyrrolidone-2, tetraglycol, triacetin, tributyrin, tripropionin and mixtures thereof. 
     
     
         43 . The biodegradable drug delivery composition according to  claim 42 , wherein said composition is an injectable liquid and forms an implant when injected into the body or are small solid particles or rod implants or spatial formulations.

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