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 agentsInfo
- 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
Links
- 239000003814 drug Substances 0.000 title claims abstract 6
- 210000001519 tissues Anatomy 0.000 title claims abstract 5
- 239000000017 hydrogel Substances 0.000 title claims 2
- 229940079593 drugs Drugs 0.000 title abstract 2
- 239000003795 chemical substances by application Substances 0.000 title 2
- 238000006065 biodegradation reaction Methods 0.000 title 1
- 230000002209 hydrophobic Effects 0.000 claims abstract 15
- 239000000203 mixture Substances 0.000 claims abstract 14
- 239000000499 gel Substances 0.000 claims abstract 9
- -1 poly(ethylene oxide) Polymers 0.000 claims 5
- 239000007864 aqueous solution Substances 0.000 claims 4
- 239000000463 material Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 239000011149 active material Substances 0.000 claims 3
- 238000004132 cross linking Methods 0.000 claims 3
- 239000011859 microparticle Substances 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- 238000001879 gelation Methods 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 150000002540 isothiocyanates Chemical class 0.000 claims 2
- 239000002502 liposome Substances 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 230000035699 permeability Effects 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrugs Drugs 0.000 claims 2
- 150000003460 sulfonic acids Chemical class 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 206010022114 Injury Diseases 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 229920002732 Polyanhydride Polymers 0.000 claims 1
- 229920001748 Polybutylene Polymers 0.000 claims 1
- 229920001273 Polyhydroxy acid Polymers 0.000 claims 1
- 229920001710 Polyorthoester Polymers 0.000 claims 1
- 229920000388 Polyphosphate Polymers 0.000 claims 1
- 229920001451 Polypropylene glycol Polymers 0.000 claims 1
- 210000003491 Skin Anatomy 0.000 claims 1
- 238000005299 abrasion Methods 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000000593 degrading Effects 0.000 claims 1
- 230000001419 dependent Effects 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 150000004676 glycans Polymers 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 239000000693 micelle Substances 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 1
- 229920001308 poly(aminoacid) Polymers 0.000 claims 1
- 229920002627 poly(phosphazenes) Polymers 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000001205 polyphosphate Substances 0.000 claims 1
- 235000011176 polyphosphates Nutrition 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 150000004804 polysaccharides Polymers 0.000 claims 1
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 1
- 150000003432 sterols Chemical class 0.000 claims 1
- 235000003702 sterols Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
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
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.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
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 |
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
ID=21697509
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/012285 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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2000
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2002
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