CA2353642A1 - Biocompatible crosslinked polymers - Google Patents

Biocompatible crosslinked polymers Download PDF

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Publication number
CA2353642A1
CA2353642A1 CA002353642A CA2353642A CA2353642A1 CA 2353642 A1 CA2353642 A1 CA 2353642A1 CA 002353642 A CA002353642 A CA 002353642A CA 2353642 A CA2353642 A CA 2353642A CA 2353642 A1 CA2353642 A1 CA 2353642A1
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crosslinker
functional groups
biocompatible
functional
polymer
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CA2353642C (en
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Amarpreet S. Sawhney
Peter G. Edelman
Chandrashekhar P. Pathak
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0019Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0024Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/74Synthetic polymeric materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/46Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14Macromolecular materials
    • A61L27/18Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/52Hydrogels or hydrocolloids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/58Materials at least partially resorbable by the body
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04Macromolecular materials
    • A61L31/06Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/145Hydrogels or hydrocolloids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/148Materials at least partially resorbable by the body
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P41/00Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91Polymers modified by chemical after-treatment
    • C08G63/912Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08Lactones or lactides

Abstract

Biocompatible crosslinked polymers, and methods for their preparation and us e, are disclosed in which the biocompatible crosslinked polymers are formed fro m water soluble precursors having electrophilic and nucleophilic groups capabl e of reacting and crosslinking in situ. Methods for making the resulting biocompatible crosslinked polymers biodegradable or not are provided, as are methods for controlling the rate of degradation. The crosslinking reactions may be carried out in situ on organs or tissues or outside the body. Applications for such biocompatible crosslinked polymers and their precursor s include controlled delivery of drugs, prevention of post-operative adhesions , coating of medical devices such as vascular grafts, wound dressings and surgical sealants.

Claims (33)

1. A method for preparing a biocompatible crosslinked polymer, comprising:
providing a biocompatible small molecule crosslinker having n crosslinker functional groups, wherein n is two or more, and wherein the crosslinker functional groups are either electrophilic or nucleophilic;
dissolving the biocompatible small molecule crosslinker in a first solvent to form a crosslinker solution;
providing a biocompatible functional polymer having m functional polymer functional groups, wherein m is two or more and the sum of n and m is five or more, and wherein the functional polymer functional groups are nucleophilic if the crosslinker functional groups are electrophilic, and the functional polymer functional groups are electrophilic if the crosslinker functional groups are nucleophilic;
dissolving the biocompatible functional polymer in a second solvent to form a functional polymer solution; and combining the crosslinker and functional polymer solutions to react the crosslinker functional groups with the functional polymer functional groups.
2. The method of claim 1, wherein combining the crosslinker and functional polymer solutions further comprises combining the crosslinker and functional polymer solutions in an animal or human body.
3. The method of claim 1, wherein providing a biocompatible small molecule crosslinker further comprises providing a biocompatible small molecule crosslinker having a solubility of at least 1 g/100 ml in an aqueous solution.
4. The method of claim 1, wherein providing a biocompatible small molecule crosslinker further comprises providing a biocompatible small molecule crosslinker having crosslinker functional groups that are electrophilic.
5. The method of claim 4, wherein providing a biocompatible small molecule crosslinker having crosslinker functional groups that are electrophilic further comprises providing a biocompatible small molecule crosslinker wherein the electrophilic crosslinker functional groups are N-hydroxysuccinimide groups.
6. The method of claim 5, wherein providing a biocompatible functional polymer further comprises providing a biocompatible functional polymer wherein the functional polymer functional groups are amines.
7. The method of claim 1, wherein providing a biocompatible small molecule crosslinker further comprises providing a biocompatible small molecule crosslinker having crosslinker functional groups that are nucleophilic.
8. The method of claim 7, wherein providing a biocompatible small molecule crosslinker having crosslinker functional groups that are nucleophilic further comprises providing a biocompatible small molecule crosslinker wherein the crosslinker functional groups are amines.
9. The method of claim 8, wherein providing a biocompatible functional polymer further comprises providing a biocompatible functional polymer wherein the functional polymer functional groups are N-hydroxysuccinimide groups.
10. The method of claim 1, wherein providing a biocompatible small molecule crosslinker further comprises providing a biocompatible small molecule crosslinker having a biodegradable link.
11. The method of claim 1, wherein providing a biocompatible functional polymer further comprises providing a biocompatible functional polymer having a biodegradable link.
12. The method of claim 1, wherein combining the crosslinker and functional polymer solutions further comprises reacting the crosslinker functional groups and the functional polymer functional groups to produce a biodegradable link.
13. The method of claim 1, further comprising:
providing a visualization agent; and dissolving the visualization agent in the first solvent.
14. The method of claim 1, further comprising:
providing a visualization agent; and dissolving the visualization agent in the second solvent.
15. A biocompatible small molecule crosslinker having n functional groups, wherein n is two or more.
16. The biocompatible small molecule crosslinker of claim 15, wherein the biocompatible small molecule crosslinker has a solubility of at least 1 g/100 ml in an aqueous solution.
17. The biocompatible small molecule crosslinker of claim 15, wherein the functional groups are nucleophilic.
18, The biocompatible small molecule crosslinker of claim 17, wherein the functional groups are amines.
19. The biocompatible small molecule crosslinker of claim 15, wherein the biocompatible small molecule crosslinker further comprises a biodegradable link.
20. A biocompatible crosslinked polymer, comprising:
at least one biocompatible small molecule crosslinker regions;
at least one biocompatible functional polymer regions, wherein the biocompatible crosslinked polymer comprises at least three links between the crosslinker regions and the functional polymer regions, and the links are a reaction product of electrophilic functional groups with nucleophilic functional groups.
21. The biocompatible crosslinked polymer of claim 20, wherein the biocompatible small molecule crosslinker regions each have a solubility of at least 1 g/100 ml in an aqueous solution.
22. The biocompatible crosslinked polymer of claim 20, wherein the biocompatible crosslinked polymer further comprises at least one biodegradable link.
23. The biocompatible crosslinked polymer of claim 20, wherein at least one of the links between the crosslinker and functional polymer regions is biodegradable.
24. A method for preventing surgical adhesions, the method comprising:
providing, at a surgical site, a first solution comprising a biocompatible small molecule crosslinker having n crosslinker functional groups, wherein n is two or more, and wherein the crosslinker functional groups are either electrophilic or nucleophilic;
providing, at the surgical site, a second solution comprising a biocompatible functional polymer having m functional polymer functional groups, wherein m is two or more and the sum of n and m is five or more, and wherein the functional polymer functional groups are nucleophilic if the crosslinker functional groups are electrophilic, and the functional polymer functional groups are electrophilic if the crosslinker functional groups are nucleophilic; and combining the first and second solutions to react the crosslinker functional groups with the functional polymer functional groups and produce a biocompatible crosslinked polymer at the surgical site.
25. The method of claim 24, wherein providing a first solution further comprises providing a first solution comprising a biocompatible small molecule crosslinker having a solubility of at least 1 g/100 ml in an aqueous solution.
26. A method for drug delivery comprising:
providing a first solution comprising a biocompatible small molecule crosslinker having n crosslinker functional groups, wherein n is two or more, and wherein the crosslinker functional groups are either electrophilic or nucleophilic;

providing a second solution comprising a biocompatible functional polymer having m functional polymer functional groups, wherein m is two or more and the sum of n and m is five or more, and wherein the functional polymer functional groups are nucleophilic if the crosslinker functional groups are electrophilic, and the functional polymer functional groups are electrophilic if the crosslinker functional groups are nucleophilic;
providing a drug;
combining the first and second solutions and the drug to react the crosslinker functional groups with the functional polymer functional groups and produce a biocompatible crosslinked polymer entrapping the drug;
and injecting or implanting the biocompatible crosslinked polymer in an animal or human body.
27. The method of claim 26, wherein providing a first solution further comprises providing a first solution comprising a biocompatible small molecule crosslinker having a solubility of at least 1 g/100 ml in an aqueous solution.
28. A method for drug delivery comprising:
providing, in an animal or human body, a first solution comprising a biocompatible small molecule crosslinker having n crosslinker functional groups, wherein n is two or more, and wherein the crosslinker functional groups are either electrophilic or nucleophilic;
providing, in the body, a second solution comprising a biocompatible functional polymer having m functional polymer functional groups, wherein m is two or more and the sum of n and m is five or more, and wherein the functional polymer functional groups are nucleophilic if the crosslinker functional groups are electrophilic, and the functional polymer functional groups are electrophilic if the crosslinker functional groups are nucleophilic;
providing, in the body, a drug; and combining, in the body, the first and second solutions and the drug to react the crosslinker functional groups with the functional polymer functional groups and form a biocompatible crosslinked polymer entrapping the drug.
29. The method of claim 28, wherein providing a first solution further comprises providing a first solution comprising a biocompatible small molecule crosslinker having a solubility of at least 1 g/100 ml in an aqueous solution.
30. A method for completely or partially blocking, augmenting, sealing or filling a natural or surgically-created void, lumen or space in an animal or human body, the method comprising:
providing a first solution comprising a biocompatible small molecule crosslinker having n crosslinker functional groups, wherein n is two or more, and wherein the crosslinker functional groups are either electrophilic or nucleophilic;
providing a second solution comprising a biocompatible functional polymer having m functional polymer functional groups, wherein m is two or more and the sum of n and m is five or more, and wherein the functional polymer functional groups are nucleophilic if the crosslinker functional groups are electrophilic, and the functional polymer functional groups are electrophilic if the crosslinker functional groups are nucleophilic;
combining the first and second solutions solutions to react the crosslinker functional groups with the functional polymer functional groups and produce a biocompatible crosslinked polymer; and injecting or implanting the biocompatible crosslinked polymer in the void, lumen or space.
31. The method of claim 30, wherein providing a first solution further comprises providing a first solution comprising a biocompatible small molecule crosslinker having a solubility of at least 1 g/100 ml in an aqueous solution.
32. A method for completely or partially blocking, augmenting, sealing or filling a natural or surgically-created void, lumen or space in an animal or human body. the method comprising:
providing, in the void, lumen or space, a first solution comprising a biocompatible small molecule crosslinker having n crosslinker functional groups, wherein n is two or more, and wherein the crosslinker functional groups are either electrophilic or nucleophilic;
providing, in the void, lumen or space, a second solution comprising a biocompatible functional polymer having m functional polymer functional groups, wherein m is two or more and the sum of n and m is five or more, and wherein the functional polymer functional groups are nucleophilic if the crosslinker functional groups are electrophilic, and the functional polymer functional groups are electrophilic if the crosslinker functional groups are nucleophilic; and combining the first and second solutions to react the crosslinker functional groups with the functional polymer functional groups and produce a biocompatible crosslinked polymer in the void, lumen or space.
33. The method of claim 32, wherein providing a first solution further comprises providing a first solution comprising a biocompatible small molecule crosslinker having a solubility of at least 1 g/100 ml in an aqueous solution.
CA002353642A 1998-12-04 1999-12-03 Biocompatible crosslinked polymers Expired - Lifetime CA2353642C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11084998P 1998-12-04 1998-12-04
US60/110,849 1998-12-04
PCT/US1999/028718 WO2000033764A1 (en) 1998-12-04 1999-12-03 Biocompatible crosslinked polymers

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CA2353642A1 true CA2353642A1 (en) 2000-06-15
CA2353642C CA2353642C (en) 2009-11-10

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US (4) US6566406B1 (en)
EP (1) EP1137373A4 (en)
JP (2) JP2002531217A (en)
AU (1) AU2707500A (en)
CA (1) CA2353642C (en)
WO (1) WO2000033764A1 (en)

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