Implantable bio-resorbable polymer

Patent metadata

Field	Value
Publication number	US-9320804-B2
Application number	US-201013395610-A
Country	US
Kind code	B2
Filing date	Sep 9, 2010
Priority date	Sep 10, 2009
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

The present invention relates to a polymer obtained from the polymerization of: (i) at least one monomer of formula (I) (CH 2 ═CR 1 )CO—K (I) wherein: K represents 0-Z or NH—Z, Z representing (CR 2 R 3 ) m —CH 3 , (CH 2 —CH 2 —O) m —H, (CH 2 —CH 2 —O) m —CH 3 , (CH 2 ) m —NR 4 R 5 with m representing an integer from 1 to 30; R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or a C1-C6 alkyl; and (ii) at least one bio-resorbable block copolymer cross-linker.

First claim

The invention claimed is:

1. A polymer obtained from the polymerization of:
(i) at least one monomer of formula (I)
(CH 2 ═CR 1 )CO—K  (I)

 wherein:
—K represents O—Z or NH—Z, Z representing (CR 2 R 3 ) m —CH 3 , (CH 2 —CH 2 —O) m —H, (CH 2 —CH 2 —O) m —CH 3 , (CH 2 ) m —NR 4 R 5 with m representing an integer from 1 to 30;
—R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or a C1-C6 alkyl; and

(ii) at least one bio-resorbable block copolymer cross-linker, wherein the bio-resorbable block copolymer cross-linker is linear and presents (CH 2 ═(CR 6 ))— groups at both extremities, wherein R 6 independently represents H or a C1-C6 alkyl, and wherein the block of the bio-resorbable block copolymer cross-linker is selected from the group consisting of:
polyethylene glycol (PEG), poly-lactic acid (PLA), poly-glycolic acid (PGA) and poly-lactic-glycolic acid (PLGA), and combinations thereof, wherein the monomer is poly(ethylene glycol) methyl ether methacrylate and wherein the bio-resorbable block copolymer cross-linker is (CH 2 ═CCH 3 )CO-PLGA-PEG-PLGA-CO(CCH 3 ═CH 2 ).

2. The polymer according to claim 1 , which is in the form of a film, a foam, a particle, in particular a spherical particle, a lump, a thread, or a sponge.

3. A pharmaceutical composition comprising at least one polymer in association with a pharmaceutically acceptable carrier, wherein the polymer is obtained from the polymerization of:
(i) at least one monomer of formula (I)
(CH 2 ═CR 1 )CO—K  (I)

 wherein:
—K represents O—Z or NH—Z, Z representing (CR 2 R 3 ) m —CH 3 , (CH 2 —CH 2 —O ) m —H, (CH 2 —CH 2 —O) m —CH 3 , (CH 2 ) m —NR 4 R 5 with m representing an integer from 1 to 30;
—R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or a C1-C6 alkyl; and

(ii) at least one bio-resorbable block copolymer cross-linker, wherein the bio-resorbable block copolymer cross-linker is linear and presents (CH 2 =(CR 6 ))— groups at both extremities, wherein R 6 independently represents H or a C1-C6 alkyl, and wherein the block of the bio-resorbable block copolymer cross-linker is selected from the group consisting of:
 polyethylene glycol (PEG), poly-lactic acid (PLA), poly-glycolic acid (PGA) and poly-lactic-glycolic acid (PLGA), and combinations thereof,. wherein the monomer is poly(ethylene glycol) methyl ether methacrylate and wherein the bio-resorbable block copolymer cross-linker is (CH 2 ═CCH 3 )CO-PLGA-PEG-PLGA-CO(CCH 3 ═CH 2 ).

4. An implant comprising a pharmaceutical composition comprising at least one polymer in association with a pharmaceutically acceptable carrier, wherein the polymer is obtained from the polymerization of:
(i) at least one monomer of formula (I)
(CH 2 ═CR 1 )CO—K  (I)

 wherein:
—K represents O—Z or NH—Z, Z representing (CR 2 R 3 ) m —CH 3 , (CH 2 —CH 2 —O) m —H, (CH 2 —CH 2 —O) m —CH 3 , (CH 2 ) m —NR 4 R 5 with m representing an integer from 1 to 30;
—R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or a C1-C6 alkyl; and

(ii) at least one bio-resorbable block copolymer cross-linker, wherein the bio-resorbable block copolymer cross-linker is linear and presents (CH 2 ═(CR 6 ))— groups at both extremities, wherein R 6 independently represents H or a C1-C6 alkyl, and wherein the block of the bio-resorbable block copolymer cross-linker is selected from the group consisting of:
 polyethylene glycol (PEG), poly-lactic acid (PLA), poly-glycolic acid (PGA) and poly-lactic-glycolic acid (PLGA), and combinations thereof, wherein the monomer is poly(ethylene glycol) methyl ether methacrylate and wherein the bio-resorbable block copolymer cross-linker is (CH 2 ═CCH 3 )CO-PLGA-PEG-PLGA-CO(CCH 3 ═CH 2 ).

5. An injectable pharmaceutical comprising a pharmaceutical composition comprising at least one polymer in association with a pharmaceutically acceptable carrier, wherein the polymer is obtained from the polymerization of:
(i) at least one monomer of formula (I)
(CH 2 ═CR 1 )CO—K  (I)

 wherein:
—K represents O—Z or NH—Z, Z representing (CR 2 R 3 ) m —CH 3 , (CH 2 —CH 2 —O) m —H, (CH 2 —CH 2 —O) m —CH 3 , (CH 2 ) m —NR 4 R 5 with m representing an integer from 1 to 30;
—R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or a C1-C6 alkyl; and

(ii) at least one bio-resorbable block copolymer cross-linker, wherein the bio-resorbable block copolymer cross-linker is linear and presents (CH 2 ═(CR 6 ))— groups at both extremities, wherein R 6 independently represents H or a C1-C6 alkyl, and wherein the block of the bio-resorbable block copolymer cross-linker is selected from the group consisting of:
 polyethylene glycol (PEG), poly-lactic acid (PLA), poly-glycolic acid (PGA) and poly-lactic-glycolic acid (PLGA), and combinations thereof, wherein the monomer is poly(ethylene glycol) methyl ether methacrylate and wherein the bio- resorbable block copolymer cross-linker is (CH 2 ═CCH 3 )CO-PLGA-PEG-PLGA-CO(CCH 3 ═CH 2 ).

6. The implant of claim 4 suitable for implantation into tissues, internal anatomical spaces, body cavities, ducts and vessels.

7. A method for treating a condition selected from the group consisting of inflammation and cancer comprising administering a therapeutically effective amount of a pharmaceutical composition to a patient in need of treatment, wherein the pharmaceutical composition comprises at least one polymer in association with a pharmaceutically acceptable carrier, wherein the polymer is obtained from the polymerization of:
(i) at least one monomer of formula (I)
(CH 2 ═CR 1 )CO—K  (I)

 wherein:
—K represents O—Z or NH—Z, Z representing (CR 2 R 3 ) m —CH 3 , (CH 2 —CH 2 —O) m —H, (CH 2 —CH 2 —O) m —CH 3 , (CH 2 ) m —NR 4 R 5 with m representing an integer from 1 to 30;
—R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or a C1 -C6 alkyl; and

(ii) at least one bio-resorbable block copolymer cross-linker, wherein the bio-resorbable block copolymer cross-linker is linear and presents (CH 2 =(CR 6 ))— groups at both extremities, wherein R 6 independently represents H or a C1-C6 alkyl, and wherein the block of the bio-resorbable block copolymer cross-linker is selected from the group consisting of:
 polyethylene glycol (PEG), poly-lactic acid (PLA), poly-glycolic acid (PGA) and poly-lactic-glycolic acid (PLGA), and combinations thereof, wherein the monomer is poly(ethylene glycol) methyl ether methacrylate and wherein the bio- resorbable block copolymer cross-linker is (CH 2 ═CCH 3 )CO-PLGA-PEG-PLGA-CO(CCH 3 ═CH 2 ).

8. The pharmaceutical composition according to claim 3 , wherein the at least one polymer is in association with a drug or a prodrug.

9. A method for implanting a pharmaceutical composition to a patient in need thereof, comprising implanting an effective amount of the pharmaceutical composition into said patient at a location selected from tissues, internal anatomical spaces, body cavities, ducts and vessels, wherein the pharmaceutical composition comprises at least one polymer in association with a pharmaceutically acceptable carrier, wherein the polymer is obtained from the polymerization of:
(i) at least one monomer of formula (I)
(CH 2 ═CR 1 )CO—K  (I)

 wherein:
—K represents O—Z or NH—Z, Z representing (CR 2 R 3 ) m —Ch 3 , (CH 2 —CH 2 —O ) m —H, (CH 2 —CH 2 —O) m —CH 3 , (CH 2 ) m —NR 4 R 5 with m representing an integer from 1 to 30;
—R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or a C1-C6 alkyl; and

(ii) at least one bio-resorbable block copolymer cross-linker, wherein the bio-resorbable block copolymer cross-linker is linear and presents (CH 2 ═(CR 6 ))— groups at both extremities, wherein R 6 independently represents H or a C1-C6 alkyl, and wherein the block of the bio-resorbable block copol

Assignees

• Moine Laurence
• Bedouet Laurent
• Laurent Alexandre
• Labarre Denis
• Wassef Michel
• Nguyen Van Nga
• Occlugel
• Centre Nat Rech Scient
• Univ Paris Sud 11
• Assistance Publique—Hopitaux de Paris
• Univ Paris Diderot Paris 7

Inventors

• Moine Laurence
• Bedouet Laurent
• Laurent Alexandre
• Labarre Denis
• Wassef Michel
• Nguyen Van Nga

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• C08F290/06 Primary

  Polymers provided for in subclass C08G · CPC title

• C08F290/061

  Polyesters; Polycarbonates · CPC title

• C08L2205/02

  containing two or more polymers of the same C08L -group · CPC title