IP Library Granted Patent US 9,320,804
Granted Patent B2
US 9,320,804 · App. 13/395,610 · Granted Apr 26, 2016

Implantable bio-resorbable polymer

Inventors: Laurence Moine (Saint-Cloud, FR); Laurent Bedouet (Paris, FR); Alexandre Laurent (Courbevoie, FR); Denis Labarre (Villebon, FR); Michel Wassef (Paris, FR); Van Nga Nguyen (Antony, FR)
Assignees: OCCLUGEL; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); UNIVERSITE PARIS-SUD 11; ASSISTANCE PUBLIQUE—HOPITAUX DE PARIS; UNIVERSITE PARIS DIDEROT PARIS 7
A61K47/48176A61K47/48869C08F290/061C08F290/062C08L55/005C08L2205/02
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Quick Facts
Patent No.
US 9,320,804
App. No.
13/395,610
Granted
Apr 26, 2016
Kind
B2
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.

Claims (51)

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 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 ).

Assignments (5)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 058630 FRAME: 0874. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER. Recorded May 4, 2022
From: UNIVERSITÉ PARIS-SUD
To: UNIVERSITÉ PARIS-SACLAY
Reel/Frame 059952/0787 →
CHANGE OF NAME Recorded Mar 25, 2022
From: UNIVERSITÉ DE PARIS
To: UNIVERSITÉ PARIS CITÉ
Reel/Frame 059504/0225 →
MERGER Recorded Jan 12, 2022
From: UNIVERSITÉ PARIS-SUD
To: UNIVERSITÉ PARIS-SACLAY
Reel/Frame 058630/0874 →
MERGER Recorded Jul 12, 2021
From: UNIVERSITE PARIS DIDEROT - PARIS 7
To: UNIVERSITE DE PARIS
Reel/Frame 056817/0647 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2012
From: MOINE, LAURENCE; BEDOUET, LAURENT; LAURENT, ALEXANDRE; LABARRE, DENIS; WASSEF, MICHEL; NGUYEN, VAN NGA
To: OCCLUGEL; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); UNIVERSITE PARIS-SUD 11; ASSISTANCE PUBLIQUE - HOPITAUX DE PARIS; UNIVERSITE PARIS DIDEROT PARIS 7
Reel/Frame 028346/0235 →
Priority Claims (1)
EP 09305830 · Sep 10, 2009 · regional
Continuity (2)
Provisional Application 61241183 · Sep 10, 2009
Related Publication 20120230937A1 · Sep 13, 2012