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WO1997005185B1 - Multiblock biodegradable hydrogels for use as controlled release agents for drugs delivery and tissue treatment agents - Google Patents

Multiblock biodegradable hydrogels for use as controlled release agents for drugs delivery and tissue treatment agents

Info

Publication number
WO1997005185B1
WO1997005185B1 PCT/US1996/012285 US9612285W WO9705185B1 WO 1997005185 B1 WO1997005185 B1 WO 1997005185B1 US 9612285 W US9612285 W US 9612285W WO 9705185 B1 WO9705185 B1 WO 9705185B1
Authority
WO
WIPO (PCT)
Prior art keywords
macromer
composition
hydrophobic
group
gel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1996/012285
Other languages
French (fr)
Other versions
WO1997005185A3 (en
WO1997005185A2 (en
Filing date
Publication date
Application filed filed Critical
Priority to EP96926138A priority Critical patent/EP0842209B1/en
Priority to DE69636626T priority patent/DE69636626T2/en
Priority to JP9507762A priority patent/JPH11510837A/en
Publication of WO1997005185A2 publication Critical patent/WO1997005185A2/en
Publication of WO1997005185A3 publication Critical patent/WO1997005185A3/en
Publication of WO1997005185B1 publication Critical patent/WO1997005185B1/en
Anticipated expiration legal-status Critical
Priority to MXPA/A/1998/001706A priority patent/MXPA98001706A/en
Ceased legal-status Critical Current

Links

Abstract

Gel-forming macromers including at least four polymeric blocks, at least two of which are hydrophobic and at least one of which is hydrophilic, and including a cross-linkable group are provided. The macromers can be covalently cross-linked to form a gel on a tissue surface in vivo. The gels formed from the macromers have a combination of properties including thermosensitivity and lipophilicity, and are useful in a variety of medical applications including drug delivery and tissue coating.

Claims

AMENDED CLAIMS[received by the International Bureau on 4 April 1997 (04.04.97); original claims 1-50 replaced by amended claims 1-37 (5 pages)]
1. A macromer comprising at least four covalently linked polymeric blocks and at least one crossiinkable group, wherein a) at least one block is hydrophilic b) each hydrophilic block individually has a water solubility of at least 1 gram/liter; and c) at least two blocks are sufficiently hydrophobic to aggregate to form micelles in an aqueous continuous phase, wherein the macromer is capable of being reversibly gelled or crosslinked in solution in response to a change in temperature, ionic concentration or pH, and wherein the crossiinkable group is selected from the group consisting of epoxides, isocyanates, isothiocyanates, aldehydes, amines, sulfonic acids, carboxylic acids and ethylenically unsaturated groups.
2. The macromer of claim 1 wherein the hydrophilic blocks are the same or different and are selected from the group consisting of poly (ethylene glycol), poly(ethylene oxide), poly (vinyl alcohol), poly (vinylpyrrolidone), poly(ethyloxazoline), polysaccharides and amino acid polymers.
3. The macromer of claim 1 wherein the hydrophobic blocks are the same or different and are selected from the group consisting of polypropylene oxide, polybutylene oxide, hydrophobic mixed poly(alkylene oxides), polyhydroxy acids, polylactones,polyamino acids, poly anhydrides, polyorthoesters, polyphosphazenes, and polyphosphates.
4. The macromer of claim 1 wherein the crossiinkable group is selected from the group consisting of epoxides, isocyanates, isothiocyanates, aldehydes, amines, sulfonic acids and carboxylic acids.
5. The macromer of claim 1 wherein the crossiinkable groups comprise ethylenically unsaturated groups. 51
6. The macromer of claim 1, further comprising at least one ionically charged moiety covalently attached to the macromer.
7. The macromer of claim 1 comprising at least two chemically distinct hydrophobic blocks.
8. The macromer of claim 1 wherein the crossiinkable groups are separated by at least one hydrophobic block, wherein the hydrophobic block is capable of degrading under physiological conditions.
9. The macromer of claim 1 wherein at least one hydrophobic block is separated from any crossiinkable group by at least one hydrophilic block.
10. The macromer of claim 1 wherein each hydrophobic block is separated from any other hydrophobic block by a hydrophilic block.
11. The macromer of claim 1 wherein the macromer comprises at least one thermally sensitive region, and wherein a solution of the macromer is capable of gelling or crosslinking to produce a hydrogel with a temperature dependent volume.
12. The macromer of claim 1 wherein the macromer is capable of thermoreversible gelation in an aqueous solution of the macromer at a concentration of at least 2% by weight, and wherein the gelation temperature is between about 0°C and about 65°C.
13. A composition comprising a macromer as described in claim 1 and a therapeutic agent. 52
14. A composition comprising a macromer as described in claim 1 and a hydrophobic material non-covalently associated with the macromer.
15. The composition of claim 14, wherein the hydrophobic material is selected from the group consisting of a hydrocarbon, a lipid, a fatty acid, and a sterol.
16. A composition including a macromer as described in claim 1 and a pharmaceutically acceptable carrier.
17. The composition of claim 16 wherein the carrier is suitable for parenteral administration.
18. The composition of claim 16, wherein the macromer is gelled.
19. The composition of claim 16, wherein the crossiinkable groups on the macromer are covalently crosslinked.
20. The composition of claim 19 further comprising a therapeutic agent.
21. The composition of claim 20, wherein the therapeutic agent is provided in a form selected from the group consisting of particles, microparticles, pro-drug conjugates, or liposomes.
22. The composition of claim 19 wherein the gel is formed on a surface of biological tissue.
23. The composition of claim 19 wherein the gel is formed on a surface of a medical device. 53
24. The composition of claim 19 wherein the gel is formed between opposed surfaces, tending thereby to adhere said surfaces.
25. Use of a macromer as described in claim 1 to prepare a composition for treating a medical condition by applying an aqueous solution of the macromer to tissue in vivo.
26. The use of claim 25 wherein the aqueous solution further comprises a dissolved or suspended therapeutic agent.
27. The use of claim 25 wherein the medical condition is a burn or abrasion of the skin.
28. The use of claim 25 wherein the medical condition is an injury resulting from a surgical intervention.
29. The use of claim 28 wherein the surgery is angioplasty.
30. The use of claim 28 wherein the surgery is conducted through the cannula of a trocar.
31. A method for controlling the rate of delivery of a biologically active material, comprising: a) mixing an active material with a solution of a macromer as described in claim 1 ; b) crosslinking the macromer to form a gel; and c) changing the permeability of the gel to effect controlled delivery of the material.
32. The method of claim 31 wherein the crosslinked gel changes in permeability in response to an effect selected from the group consisting of a change in temperature, a change in ionic concentration, and a change in pH.
33. The method of claim 31 wherein at least one hydrophobic block aggregates in aqueous solution to form a hydrophobic domain.
34. The method of claim 33 wherein the hydrophobicity of said domain is controlled by selecting the hydrophobicity of the block.
35. The method of claim 40 wherein the hydrophobicity of said domain is controlled by adding hydrophobic materials to the gel-forming macromer solution.
36. The method of claim 31 wherein the active material is in the form selected from the group consisting of particles, microparticles, pro-drug conjugates, and liposomes.
37. The method of claim 36 wherein the crosslinked gel forms a microparticle after crosslinking.
PCT/US1996/012285 1995-07-28 1996-07-26 Multiblock biodegradable hydrogels for use as controlled release agents for drugs delivery and tissue treatment agents Ceased WO1997005185A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP96926138A EP0842209B1 (en) 1995-07-28 1996-07-26 Multiblock biodegradable hydrogels for use as controlled release agents for drugs and tissue treatment agents
DE69636626T DE69636626T2 (en) 1995-07-28 1996-07-26 BIODEGRADABLE MULTIBLOKHYDROGENES AND THEIR USE AS CARRIERS FOR CONTROLLED RELEASE PHARMACOLOGICALLY ACTIVE MATERIALS AND TISSUE CONTACT MATERIALS
JP9507762A JPH11510837A (en) 1995-07-28 1996-07-26 Multi-block biodegradable hydrogels for use as controlled release and tissue treatment agents for drug delivery
MXPA/A/1998/001706A MXPA98001706A (en) 1995-09-08 1998-03-03 Articles coated with dependable coatings capable of accepting organic pigment electrofotograf

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US172395P 1995-07-28 1995-07-28
US60/001,723 1995-07-28

Publications (3)

Publication Number Publication Date
WO1997005185A2 WO1997005185A2 (en) 1997-02-13
WO1997005185A3 WO1997005185A3 (en) 1997-03-13
WO1997005185B1 true WO1997005185B1 (en) 1997-05-15

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/012285 Ceased WO1997005185A2 (en) 1995-07-28 1996-07-26 Multiblock biodegradable hydrogels for use as controlled release agents for drugs delivery and tissue treatment agents

Country Status (7)

Country Link
US (5) US6201065B1 (en)
EP (1) EP0842209B1 (en)
JP (2) JPH11510837A (en)
AT (1) ATE342295T1 (en)
CA (1) CA2228118A1 (en)
DE (1) DE69636626T2 (en)
WO (1) WO1997005185A2 (en)

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