CA2281614C - Monomers derived from hydroxy acids and polymers prepared therefrom - Google Patents
Monomers derived from hydroxy acids and polymers prepared therefrom Download PDFInfo
- Publication number
- CA2281614C CA2281614C CA002281614A CA2281614A CA2281614C CA 2281614 C CA2281614 C CA 2281614C CA 002281614 A CA002281614 A CA 002281614A CA 2281614 A CA2281614 A CA 2281614A CA 2281614 C CA2281614 C CA 2281614C
- Authority
- CA
- Canada
- Prior art keywords
- poly
- group
- hydrogen
- amide
- carbon atoms
- 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.)
- Expired - Lifetime
Links
- 239000000178 monomer Substances 0.000 title abstract description 47
- 229920000642 polymer Polymers 0.000 title description 79
- 150000001261 hydroxy acids Chemical class 0.000 title description 10
- -1 Poly(amide carbonates Chemical class 0.000 claims abstract description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000000338 in vitro Methods 0.000 claims description 10
- 238000012377 drug delivery Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000001727 in vivo Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 3
- 230000035755 proliferation Effects 0.000 claims description 3
- 239000002407 tissue scaffold Substances 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims 4
- 239000000599 controlled substance Substances 0.000 claims 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 229920001279 poly(ester amides) Polymers 0.000 abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 description 27
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 26
- 230000015556 catabolic process Effects 0.000 description 26
- 238000000034 method Methods 0.000 description 24
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 14
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 14
- BRNNQLLASRVTMB-SFHVURJKSA-N ethyl (2s)-3-(4-hydroxyphenyl)-2-[3-(4-hydroxyphenyl)propanoylamino]propanoate Chemical compound C([C@@H](C(=O)OCC)NC(=O)CCC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BRNNQLLASRVTMB-SFHVURJKSA-N 0.000 description 13
- 210000001519 tissue Anatomy 0.000 description 13
- 229960004441 tyrosine Drugs 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000012620 biological material Substances 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 229960000448 lactic acid Drugs 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 229920000954 Polyglycolide Polymers 0.000 description 5
- 150000001718 carbodiimides Chemical class 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 239000007857 degradation product Substances 0.000 description 5
- 239000004310 lactic acid Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 229920000747 poly(lactic acid) Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZJSQZQMVXKZAGW-UHFFFAOYSA-N 2H-benzotriazol-4-ol hydrate Chemical compound O.OC1=CC=CC2=C1N=NN2 ZJSQZQMVXKZAGW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 229920006237 degradable polymer Polymers 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- SBBWEQLNKVHYCX-JTQLQIEISA-N ethyl L-tyrosinate Chemical compound CCOC(=O)[C@@H](N)CC1=CC=C(O)C=C1 SBBWEQLNKVHYCX-JTQLQIEISA-N 0.000 description 4
- 229920001230 polyarylate Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910014033 C-OH Inorganic materials 0.000 description 3
- 229920001634 Copolyester Polymers 0.000 description 3
- 229910014570 C—OH Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- OAOSXODRWGDDCV-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine;4-methylbenzenesulfonic acid Chemical compound CN(C)C1=CC=NC=C1.CC1=CC=C(S(O)(=O)=O)C=C1 OAOSXODRWGDDCV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001308 poly(aminoacid) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000000807 solvent casting Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- COMSBNSFYYEQOJ-INIZCTEOSA-N (2s)-3-(4-hydroxyphenyl)-2-[3-(4-hydroxyphenyl)propanoylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CCC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 COMSBNSFYYEQOJ-INIZCTEOSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- LFPLRGMCQXEYDO-UHFFFAOYSA-N 4-[1-(4-carboxyphenoxy)propoxy]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1OC(CC)OC1=CC=C(C(O)=O)C=C1 LFPLRGMCQXEYDO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 150000008553 L-tyrosines Chemical class 0.000 description 1
- ODYCAZSSUVCHNU-XLAORIBOSA-N Laurencin Natural products CC[C@H]1C[C@H](CC=CC[C@@H]1Br)[C@@H](CC=CC#C)OC(=O)C ODYCAZSSUVCHNU-XLAORIBOSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000031737 Tissue Adhesions Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000015191 beet juice Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229920013641 bioerodible polymer Polymers 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004098 cellular respiration Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000037029 cross reaction Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- A61L—METHODS 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
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
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- A61L—METHODS 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A61L—METHODS 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
- A61L31/00—Materials 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
- A61L31/04—Macromolecular materials
- A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS 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
- A61L31/00—Materials 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
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/148—Materials at least partially resorbable by the body
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
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- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6858—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/045—Aromatic polycarbonates containing aliphatic unsaturation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/1641—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/18—Block or graft polymers
- C08G64/183—Block or graft polymers containing polyether sequences
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3314—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic
- C08G65/3315—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic
- C08G65/3317—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic phenolic
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
- A61K9/204—Polyesters, e.g. poly(lactide-co-glycolide)
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Vascular Medicine (AREA)
- Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Materials Engineering (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Transplantation (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
- Materials For Medical Uses (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Graft Or Block Polymers (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3821397P | 1997-02-18 | 1997-02-18 | |
| US60/038,213 | 1997-02-18 | ||
| US6465697P | 1997-11-07 | 1997-11-07 | |
| US6490597P | 1997-11-07 | 1997-11-07 | |
| US60/064,905 | 1997-11-07 | ||
| US60/064,656 | 1997-11-07 | ||
| PCT/US1998/003127 WO1998036013A1 (en) | 1997-02-18 | 1998-02-18 | Monomers derived from hydroxy acids and polymers prepared therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2281614A1 CA2281614A1 (en) | 1998-08-20 |
| CA2281614C true CA2281614C (en) | 2008-11-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002281614A Expired - Lifetime CA2281614C (en) | 1997-02-18 | 1998-02-18 | Monomers derived from hydroxy acids and polymers prepared therefrom |
Country Status (9)
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| US (1) | US6284862B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP0961801B1 (cg-RX-API-DMAC7.html) |
| JP (3) | JP4410857B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE259386T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU729552B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2281614C (cg-RX-API-DMAC7.html) |
| DE (1) | DE69821600T2 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA99007662A (cg-RX-API-DMAC7.html) |
| WO (1) | WO1998036013A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (71)
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| US6120491A (en) * | 1997-11-07 | 2000-09-19 | The State University Rutgers | Biodegradable, anionic polymers derived from the amino acid L-tyrosine |
| CA2281614C (en) * | 1997-02-18 | 2008-11-18 | Rutgers, The State University Of New Jersey | Monomers derived from hydroxy acids and polymers prepared therefrom |
| US6468519B1 (en) | 1997-09-10 | 2002-10-22 | Rutgers, The State University Of New Jersey | Polyanhydrides with biologically active degradation products |
| US7122615B1 (en) | 1998-09-10 | 2006-10-17 | Rutgers, The State University Of New Jersey | Polyanhydrides with therapeutically useful degradation products |
| US6486214B1 (en) | 1997-09-10 | 2002-11-26 | Rutgers, The State University Of New Jersey | Polyanhydride linkers for production of drug polymers and drug polymer compositions produced thereby |
| US6602497B1 (en) | 1997-11-07 | 2003-08-05 | Rutgers, The State University | Strictly alternating poly(alkylene oxide ether) copolymers |
| DE69825619T2 (de) * | 1997-11-07 | 2005-09-01 | Rutgers, The State University | Strikt alternierende poly(alkylenoxid)copolymere |
| US6623521B2 (en) | 1998-02-17 | 2003-09-23 | Md3, Inc. | Expandable stent with sliding and locking radial elements |
| US20070233272A1 (en) * | 1999-02-23 | 2007-10-04 | Boyce Todd M | Shaped load-bearing osteoimplant and methods of making same |
| US8133421B2 (en) | 1999-02-23 | 2012-03-13 | Warsaw Orthopedic, Inc. | Methods of making shaped load-bearing osteoimplant |
| JP2002541925A (ja) * | 1999-04-16 | 2002-12-10 | ラトガーズ，ザ ステイト ユニバーシティ | 組織工学用多孔質ポリマー足場 |
| US6103255A (en) | 1999-04-16 | 2000-08-15 | Rutgers, The State University | Porous polymer scaffolds for tissue engineering |
| US6426145B1 (en) * | 1999-05-20 | 2002-07-30 | Scimed Life Systems, Inc. | Radiopaque compositions for visualization of medical devices |
| US6685928B2 (en) | 1999-12-07 | 2004-02-03 | Rutgers, The State University Of New Jersey | Therapeutic compositions and methods |
| US20040038948A1 (en) | 1999-12-07 | 2004-02-26 | Uhrich Kathryn E. | Therapeutic compositions and methods |
| US7521061B2 (en) | 1999-12-31 | 2009-04-21 | Rutgers, The State University Of New Jersey | Pharmaceutical formulation for regulating the timed release of biologically active compounds based on a polymer matrix |
| AU784226B2 (en) * | 1999-12-31 | 2006-02-23 | Rutgers, The State University | Pharmaceutical formulation for regulating the timed release of biologically active compounds based on a polymer matrix |
| EP1251864A4 (en) | 1999-12-31 | 2006-02-22 | Univ Rutgers | PHARMACEUTICAL FORMULATION COMPRISING A POLYMERIC MIXTURE AND AN ACTIVE COMPOUND FOR TIME-RELEASED RELEASE |
| WO2002009769A2 (en) | 2000-07-27 | 2002-02-07 | Rutgers, The State University Of New Jersey | Therapeutic azo-compounds for drug delivery |
| JP5244279B2 (ja) | 2000-07-27 | 2013-07-24 | ラトガーズ，ザ ステイト ユニバーシティ | 治療用ポリエステルおよびポリアミド |
| WO2003065928A2 (en) | 2002-02-07 | 2003-08-14 | Rutgers, The State University Of New Jersey | Therapeutic polyesters and polyamides |
| CA2531894C (en) * | 2003-09-25 | 2014-02-11 | Rutgers, The State University | Inherently radiopaque polymeric products for embolotherapy |
| US7368169B2 (en) * | 2003-12-01 | 2008-05-06 | Rutgers, The State University Of New Jersey | Hydrazide compounds with angiogenic activity |
| CA2555026A1 (en) * | 2004-01-30 | 2005-08-18 | Osteotech, Inc. | Stacking implants for spinal fusion |
| JP5107706B2 (ja) | 2004-07-08 | 2012-12-26 | レヴァ メディカル、 インコーポレイテッド | 医療用途向けの側鎖結晶性ポリマー |
| US8703113B2 (en) | 2004-07-08 | 2014-04-22 | Reva Medical Inc. | Side-chain crystallizable polymers for medical applications |
| US7763065B2 (en) | 2004-07-21 | 2010-07-27 | Reva Medical, Inc. | Balloon expandable crush-recoverable stent device |
| US20060034891A1 (en) * | 2004-08-12 | 2006-02-16 | Laurie Lawin | Biodegradable controlled release bioactive agent delivery device |
| US20060034769A1 (en) * | 2004-08-13 | 2006-02-16 | Rutgers, The State University | Radiopaque polymeric stents |
| EP1955716B1 (en) * | 2004-08-13 | 2014-04-30 | Rutgers, The State University | Radiopaque polymeric stents |
| US8292944B2 (en) | 2004-12-17 | 2012-10-23 | Reva Medical, Inc. | Slide-and-lock stent |
| US8007775B2 (en) | 2004-12-30 | 2011-08-30 | Advanced Cardiovascular Systems, Inc. | Polymers containing poly(hydroxyalkanoates) and agents for use with medical articles and methods of fabricating the same |
| US7202325B2 (en) | 2005-01-14 | 2007-04-10 | Advanced Cardiovascular Systems, Inc. | Poly(hydroxyalkanoate-co-ester amides) and agents for use with medical articles |
| US7914574B2 (en) | 2005-08-02 | 2011-03-29 | Reva Medical, Inc. | Axially nested slide and lock expandable device |
| US9149378B2 (en) | 2005-08-02 | 2015-10-06 | Reva Medical, Inc. | Axially nested slide and lock expandable device |
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| US8007526B2 (en) | 2005-12-01 | 2011-08-30 | Bezwada Biomedical, Llc | Difunctionalized aromatic compounds and polymers therefrom |
| US8287914B2 (en) | 2006-01-12 | 2012-10-16 | Rutgers, The State University Of New Jersey | Biomimetic hydroxyapatite synthesis |
| AU2007236549B2 (en) | 2006-04-07 | 2011-11-03 | The University Of Melbourne | Porous polymer blend structures |
| EP2010595A4 (en) | 2006-04-07 | 2010-09-08 | Univ Queensland | POROUS POLYMER STRUCTURES |
| US8507639B2 (en) * | 2006-09-11 | 2013-08-13 | Boston Scientific Scimed, Inc. | Radiopaque amide polymers and medical devices formed thereof |
| EP2102144A4 (en) | 2006-09-13 | 2011-03-23 | Univ Rutgers | ACTIVE SUBSTANCES AND THEIR OLIGOMERS AND POLYMERS |
| JP5165686B2 (ja) * | 2006-10-17 | 2013-03-21 | ラトガース，ザ ステート ユニバーシティ | Ｎ−置換モノマーおよびポリマー |
| US20100166854A1 (en) * | 2006-10-30 | 2010-07-01 | Rutgers, The State University Of New Jersey | Electrospun matrices for delivery of hydrophilic and lipophilic compounds |
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| EP2459638B1 (en) | 2009-07-31 | 2017-09-27 | Rutgers, The State University of New Jersey | Monomers and phase-separated biocompatible polymer compositions prepared therefrom for medical uses |
| JP6031355B2 (ja) | 2009-10-11 | 2016-11-24 | ラトガース，ザ ステート ユニバーシティ オブ ニュー ジャージー | 医療装置のための生体適合性重合体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2621916B1 (fr) * | 1987-10-19 | 1990-03-09 | Bioeurope | Derives de la l-tyrosine solubles dans l'eau et procede pour leur preparation |
| US5216115A (en) * | 1990-06-12 | 1993-06-01 | Rutgers, The State University Of New Jersey | Polyarylate containing derivatives of the natural amino acid L-tyrosine |
| US5099060A (en) * | 1990-06-12 | 1992-03-24 | Rutgers, The State University Of New Jersey | Synthesis of amino acid-derived bioerodible polymers |
| US5198507A (en) | 1990-06-12 | 1993-03-30 | Rutgers, The State University Of New Jersey | Synthesis of amino acid-derived bioerodible polymers |
| US5587507A (en) | 1995-03-31 | 1996-12-24 | Rutgers, The State University | Synthesis of tyrosine derived diphenol monomers |
| CA2281614C (en) * | 1997-02-18 | 2008-11-18 | Rutgers, The State University Of New Jersey | Monomers derived from hydroxy acids and polymers prepared therefrom |
-
1998
- 1998-02-18 CA CA002281614A patent/CA2281614C/en not_active Expired - Lifetime
- 1998-02-18 EP EP98906536A patent/EP0961801B1/en not_active Expired - Lifetime
- 1998-02-18 MX MXPA99007662A patent/MXPA99007662A/es unknown
- 1998-02-18 AU AU61735/98A patent/AU729552B2/en not_active Expired
- 1998-02-18 DE DE69821600T patent/DE69821600T2/de not_active Expired - Lifetime
- 1998-02-18 JP JP53600898A patent/JP4410857B2/ja not_active Expired - Fee Related
- 1998-02-18 WO PCT/US1998/003127 patent/WO1998036013A1/en not_active Ceased
- 1998-02-18 US US09/367,735 patent/US6284862B1/en not_active Expired - Lifetime
- 1998-02-18 AT AT98906536T patent/ATE259386T1/de not_active IP Right Cessation
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2008
- 2008-07-08 JP JP2008178161A patent/JP4411355B2/ja not_active Expired - Fee Related
-
2009
- 2009-08-17 JP JP2009188682A patent/JP2010006820A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0961801B1 (en) | 2004-02-11 |
| JP2010006820A (ja) | 2010-01-14 |
| AU729552B2 (en) | 2001-02-01 |
| DE69821600D1 (de) | 2004-03-18 |
| DE69821600T2 (de) | 2005-01-05 |
| JP2009019040A (ja) | 2009-01-29 |
| JP2001514618A (ja) | 2001-09-11 |
| WO1998036013A1 (en) | 1998-08-20 |
| ATE259386T1 (de) | 2004-02-15 |
| JP4411355B2 (ja) | 2010-02-10 |
| EP0961801A1 (en) | 1999-12-08 |
| MXPA99007662A (es) | 2002-07-22 |
| AU6173598A (en) | 1998-09-08 |
| EP0961801A4 (en) | 2000-05-03 |
| JP4410857B2 (ja) | 2010-02-03 |
| CA2281614A1 (en) | 1998-08-20 |
| US6284862B1 (en) | 2001-09-04 |
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