CA2453892A1 - Alkyd-lactone copolymers for medical applications - Google Patents
Alkyd-lactone copolymers for medical applications Download PDFInfo
- Publication number
- CA2453892A1 CA2453892A1 CA002453892A CA2453892A CA2453892A1 CA 2453892 A1 CA2453892 A1 CA 2453892A1 CA 002453892 A CA002453892 A CA 002453892A CA 2453892 A CA2453892 A CA 2453892A CA 2453892 A1 CA2453892 A1 CA 2453892A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- glycerol
- polymer
- lactide
- group
- 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.)
- Granted
Links
- 229920001577 copolymer Polymers 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract 32
- 150000007519 polyprotic acids Polymers 0.000 claims abstract 27
- 239000000203 mixture Substances 0.000 claims abstract 22
- 239000000178 monomer Substances 0.000 claims abstract 20
- 150000002596 lactones Chemical class 0.000 claims abstract 19
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract 16
- 239000007795 chemical reaction product Substances 0.000 claims abstract 15
- 229920000249 biocompatible polymer Polymers 0.000 claims abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 33
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 21
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 15
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims 11
- -1 monopalmitoyl Chemical compound 0.000 claims 11
- 229940014800 succinic anhydride Drugs 0.000 claims 11
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims 9
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims 8
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical group O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims 8
- SJDLIJNQXLJBBE-UHFFFAOYSA-N 1,4-dioxepan-2-one Chemical compound O=C1COCCCO1 SJDLIJNQXLJBBE-UHFFFAOYSA-N 0.000 claims 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 8
- 150000002148 esters Chemical class 0.000 claims 8
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 8
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 8
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims 8
- JJTUDXZGHPGLLC-QWWZWVQMSA-N (3r,6r)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@@H](C)OC1=O JJTUDXZGHPGLLC-QWWZWVQMSA-N 0.000 claims 7
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 7
- DZKLSFQAIYUHCL-UHFFFAOYSA-N 1,2-dihydroxy-2-(hydroxymethyl)icosan-3-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)C(O)(CO)CO DZKLSFQAIYUHCL-UHFFFAOYSA-N 0.000 claims 7
- AOLNDUQWRUPYGE-UHFFFAOYSA-N 1,4-dioxepan-5-one Chemical compound O=C1CCOCCO1 AOLNDUQWRUPYGE-UHFFFAOYSA-N 0.000 claims 7
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims 7
- SRIWKSRCGIWUSJ-UHFFFAOYSA-N C(CCCCCCCC=C/CC=C/CCCCC)(=O)C(CO)(O)CO Chemical compound C(CCCCCCCC=C/CC=C/CCCCC)(=O)C(CO)(O)CO SRIWKSRCGIWUSJ-UHFFFAOYSA-N 0.000 claims 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 7
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims 7
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 7
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 7
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 7
- 235000015165 citric acid Nutrition 0.000 claims 7
- 239000001630 malic acid Substances 0.000 claims 7
- 235000011090 malic acid Nutrition 0.000 claims 7
- RFJIYBACSXLSEQ-UHFFFAOYSA-N monostearoylglycerol Natural products CCCCCCCCCCCCCCCCCOCC(O)CO RFJIYBACSXLSEQ-UHFFFAOYSA-N 0.000 claims 7
- 239000011975 tartaric acid Substances 0.000 claims 7
- 235000002906 tartaric acid Nutrition 0.000 claims 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 7
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims 7
- HSVDYEDYDOKETI-UHFFFAOYSA-N 1,2-dihydroxy-2-(hydroxymethyl)octadecan-3-one Chemical compound CCCCCCCCCCCCCCCC(=O)C(O)(CO)CO HSVDYEDYDOKETI-UHFFFAOYSA-N 0.000 claims 6
- VGXPIUIRKFTNDS-UHFFFAOYSA-N 1,2-dihydroxy-2-(hydroxymethyl)octan-3-one Chemical compound CCCCCC(=O)C(O)(CO)CO VGXPIUIRKFTNDS-UHFFFAOYSA-N 0.000 claims 6
- PIYNUZCGMLCXKJ-UHFFFAOYSA-N 1,4-dioxane-2,6-dione Chemical compound O=C1COCC(=O)O1 PIYNUZCGMLCXKJ-UHFFFAOYSA-N 0.000 claims 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 6
- VJWXKKBAEQSRLE-UHFFFAOYSA-N 1,2-dihydroxy-2-(hydroxymethyl)dodecan-3-one Chemical compound CCCCCCCCCC(=O)C(O)(CO)CO VJWXKKBAEQSRLE-UHFFFAOYSA-N 0.000 claims 5
- QLQZSLBHQXQBSP-UHFFFAOYSA-N 1,2-dihydroxy-2-(hydroxymethyl)tetradecan-3-one Chemical compound CCCCCCCCCCCC(=O)C(O)(CO)CO QLQZSLBHQXQBSP-UHFFFAOYSA-N 0.000 claims 5
- 150000008064 anhydrides Chemical class 0.000 claims 5
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Chemical class 0.000 claims 4
- 239000001361 adipic acid Substances 0.000 claims 4
- 235000011037 adipic acid Nutrition 0.000 claims 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 4
- 235000011087 fumaric acid Nutrition 0.000 claims 4
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims 4
- 150000004820 halides Chemical class 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 4
- 239000011976 maleic acid Substances 0.000 claims 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- 239000001384 succinic acid Substances 0.000 claims 4
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims 3
- 239000012867 bioactive agent Substances 0.000 claims 3
- 239000001530 fumaric acid Substances 0.000 claims 3
- 150000001252 acrylic acid derivatives Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000000812 cholinergic antagonist Substances 0.000 claims 2
- 238000000576 coating method Methods 0.000 claims 2
- 239000012948 isocyanate Chemical group 0.000 claims 2
- 150000002513 isocyanates Chemical group 0.000 claims 2
- 150000002540 isothiocyanates Chemical group 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 150000002734 metacrylic acid derivatives Chemical group 0.000 claims 2
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 claims 1
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 1
- GCVOJEPQFHWJRN-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)C(CO)(O)CO.C(CCCCCCCCC)(=O)C(CO)(O)CO Chemical compound C(CCCCCCCCCCC)(=O)C(CO)(O)CO.C(CCCCCCCCC)(=O)C(CO)(O)CO GCVOJEPQFHWJRN-UHFFFAOYSA-N 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 102000003886 Glycoproteins Human genes 0.000 claims 1
- 108090000288 Glycoproteins Proteins 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- 239000000150 Sympathomimetic Substances 0.000 claims 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims 1
- 229920003232 aliphatic polyester Polymers 0.000 claims 1
- 239000002269 analeptic agent Substances 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 230000000578 anorexic effect Effects 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 230000000507 anthelmentic effect Effects 0.000 claims 1
- 239000000921 anthelmintic agent Substances 0.000 claims 1
- 230000003288 anthiarrhythmic effect Effects 0.000 claims 1
- 230000002456 anti-arthritic effect Effects 0.000 claims 1
- 230000001088 anti-asthma Effects 0.000 claims 1
- 230000001142 anti-diarrhea Effects 0.000 claims 1
- 230000002686 anti-diuretic effect Effects 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 230000000118 anti-neoplastic effect Effects 0.000 claims 1
- 229940035678 anti-parkinson drug Drugs 0.000 claims 1
- 230000001139 anti-pruritic effect Effects 0.000 claims 1
- 230000001754 anti-pyretic effect Effects 0.000 claims 1
- 230000002921 anti-spasmodic effect Effects 0.000 claims 1
- 239000003416 antiarrhythmic agent Substances 0.000 claims 1
- 229940124346 antiarthritic agent Drugs 0.000 claims 1
- 239000000924 antiasthmatic agent Substances 0.000 claims 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
- 229940125681 anticonvulsant agent Drugs 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 229940125714 antidiarrheal agent Drugs 0.000 claims 1
- 239000003793 antidiarrheal agent Substances 0.000 claims 1
- 229940124538 antidiuretic agent Drugs 0.000 claims 1
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- 229940030225 antihemorrhagics Drugs 0.000 claims 1
- 229940125715 antihistaminic agent Drugs 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 229940005486 antimigraine preparations Drugs 0.000 claims 1
- 239000002579 antinauseant Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 239000003908 antipruritic agent Substances 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
- 229940005529 antipsychotics Drugs 0.000 claims 1
- 239000002221 antipyretic Substances 0.000 claims 1
- 229940125716 antipyretic agent Drugs 0.000 claims 1
- 229940124575 antispasmodic agent Drugs 0.000 claims 1
- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 230000000975 bioactive effect Effects 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 230000001713 cholinergic effect Effects 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 230000001085 cytostatic effect Effects 0.000 claims 1
- 239000000850 decongestant Substances 0.000 claims 1
- 229940124581 decongestants Drugs 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 150000002238 fumaric acids Chemical class 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 239000002874 hemostatic agent Substances 0.000 claims 1
- 230000002439 hemostatic effect Effects 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 239000003326 hypnotic agent Substances 0.000 claims 1
- 230000000147 hypnotic effect Effects 0.000 claims 1
- 229940125721 immunosuppressive agent Drugs 0.000 claims 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims 1
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 claims 1
- 229940035363 muscle relaxants Drugs 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 claims 1
- 230000002445 parasympatholytic effect Effects 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 239000003368 psychostimulant agent Substances 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 229940125723 sedative agent Drugs 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 230000001975 sympathomimetic effect Effects 0.000 claims 1
- 229940064707 sympathomimetics Drugs 0.000 claims 1
- 229920001059 synthetic polymer Polymers 0.000 claims 1
- 239000003204 tranquilizing agent Substances 0.000 claims 1
- 230000002936 tranquilizing effect Effects 0.000 claims 1
- 229940124549 vasodilator Drugs 0.000 claims 1
- 239000003071 vasodilator agent Substances 0.000 claims 1
Classifications
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
-
- 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
- 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
-
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/58—Materials at least partially resorbable by the body
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
Abstract
The present invention is directed to biodegradable, biocompatible polymers that are the reaction product of a polybasic acid or derivative thereof, a monoglyceride and a lactone monomer, as well as medical devices and compositions containing such polymers.
Claims (44)
1. A composition, comprising: a synthetic, biodegradable, biocompatible polymer comprising the reaction product of a polybasic acid or derivative thereof, a monoglyceride and a lactone monomer.
2. The composition of claim 1 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acids maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
3. The composition of claim 1 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
4. The composition of claim 3 wherein said polybasic acid derivative is succinic anhydride.
5. The composition of claim 3 wherein said polybasic acid is succinic acid.
6. The composition of claim 1 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.
7. The composition of claim Z wherein said polymer is branched.
8. The composition of claim 1 wherein said polymer comprises the reaction product of said monoglyceride, said lactone monomer, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.
9. The composition of claim 1 wherein said polymer comprises the reaction product of said polybasic acid or derivative thereof, said lactone monomer, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl, glycerol, monomyrisitayl glycerol, monocaproyl, glycerol, monodecanoyl glycerol monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
10. The composition of claim 1 wherein said polymer comprises the reaction product of said monoglyceride, said polybasic acid or derivative thereof, and at least two lactone monomers selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.
11. The composition of claim 1 wherein said polymer further comprises an end-capping moiety selected from the group consisting of alkyls, alkenyls, alkynyls, acrylates, methacrylates, amines, isocyanates and isothiocyanates.
12. The composition of claim 1, further comprising an effective amount of a bioactive agent.
13. The composition of claim 12 wherein said bioactive agent is selected from the group consisting of antiinfectives, analgesics, anorexics, antihelmintics, antiarthritics, antiasthmatics, anticonvulsants, antidepressants, antidiuretics, antidiarrheals, antihistamines, antiinflammatory agents, antimigraine preparations, antinauseants, antineoplastics, antiparkinsonism drugs, antipruritics, antipsychotics, antipyretics, antispasmodics, anticholinergics, sympathomimetics, xanthine derivatives, calcium channel blockers, beta-blockers, antiarrhythmics, antihypertensives, diuretics, vasodilators, central nervous system stimulants, decongestants, hormones, steroids, hypnotics, immunosuppressives, muscle relaxants, parasympatholytics, psychostimulants, sedatives, tranquilizers, naturally derived or genetically engineered proteins, growth factors, polysaccharides, glycoproteins, or lipoproteins, oligonucleotides, antibodies, antigens, cholinergics, chemotherapeutics, hemostatics, clot dissolving agents, radioactive agents and cystostatics.
14. The composition of claim 1 comprising a microdispersion, said microdispersion comprising a solid polymer phase dispersed in a liquid polymer phase, wherein one of said solid polymer and said liquid polymer comprise the reaction product of a polybasic acid or derivative thereof, a monoglyceride, and a lactone monomer; wherein said solid polymer has a melting point between about 25°C and about 70°C, and wherein said liquid polymer has a melting point below about 25°C.
15. The composition of claim 14 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
16. The composition of claim 15 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
17. The composition of claim 16 wherein said polybasic acid derivative is succinic anhydride.
18 . The composition of claim 16 wherein said polybasic acid is succinic acid.
19. The composition of claim 14 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,3 dioxepan-2-one.
20. The composition of claim 14 further comprising an effective amount of a bioactive agent.
21. The composition of claim 14 wherein both said solid polymer and raid liquid polymer comprise the reaction product of a polybasic acid or derivative thereof, a monoglyceride, and a lactone monomer.
22. A medical device comprising a coatings said coating comprising, a synthetic, biodegradable, biocompatible polymer comprising the reaction product of a polybasic acid or derivative thereof, a monoglyceride, and a lactone monomer.
23. The medical device of claim 22 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
24. The medical device of claim 22 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
25. The medical device of claim 24 wherein said polybasic acid derivative is succinic anhydride.
26. The medical device of claim 24 wherein said polybasic acid is succinic acid.
27. The medical device of claim 22 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.
28. The medical device of Claim 22 wherein said polymer is branched.
29. The medical device of claim 22 wherein said polymer comprises the reaction product of said monoglyceride, said lactone monomer, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.
30. The medical device of claim 22 wherein said polymer comprises the reaction product of said polybasic acid or derivative thereof, said lactone monomer, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
31. The medical device of claim 22 wherein said polymer comprises the reaction product of said monoglyceride, said polybasic acid or derivative thereof, and at least two lactone monomers selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.
32. The medical device of claim 22 wherein said polymer further comprises an end-capping moiety selected from the group consisting of alkyls, alkenyls, alkynyls, acrylates, methacrylates, amines, isocyanates and isothiocyanates.
33. The medical device of claim 22, further comprising an effective amount of a bioactive accent.
34. The medical device of claim 22 further comprising an aliphatic polyester prepared from the group of monomers selected from the group consisting of glycolide, L-lactide, D-lactide, meso-lactide, rac-lactide, .epsilon.-caprolactone, trimethylene carbonate, p-dioxanone, 1,4-dioxanone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one and substituted derivatives thereof.
35. A synthetic polymer comprising the reaction product of:
a polybasic acid or derivative thereof;
a monoglyceride; and a lactone monomer.
a polybasic acid or derivative thereof;
a monoglyceride; and a lactone monomer.
36. The polymer of claim 35 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
37. The polymer of claim 35 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, menolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
38. The polymer of claim 37 wherein said polybasic acid derivative is succinic anhydride.
39. The polymer of claim 37 wherein said polybasic acid is succinic acid.
40. The polymer of claim 35 wherein said lactone monomer is selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimetlylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.
41. The polymer of claim 35 wherein said polymer is branched.
42. The polymer of claim 35 wherein said polymer comprises the reaction product of said monoglyceride, said lactone monomer, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycclic anhydride.
43. The polymer of claim 35 wherein said polymer comprises the reaction product of said polybasic acid or derivative thereof, sail lactone monomer, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, moncdecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
44. The polymer of claim 35 wherein said polymer comprises the reaction product of said monoglyceride, said polybasic acid or derivative thereof, and at least two lactone monomers selected from the group consisting of glycolide, d-lactide, l-lactide, meso-lactide, epsilon-caprolactone, para-dioxanone, trimethylene carbonate, 1,4 dioxepan-2-one, and 1,5 dioxepan-2-one.
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| US10/322,132 | 2002-12-18 |
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| DE (1) | DE60311741T2 (en) |
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-
2002
- 2002-12-18 US US10/322,132 patent/US6967234B2/en not_active Expired - Lifetime
-
2003
- 2003-12-09 AU AU2003266799A patent/AU2003266799B2/en not_active Ceased
- 2003-12-17 AT AT03257963T patent/ATE353674T1/en not_active IP Right Cessation
- 2003-12-17 EP EP03257963A patent/EP1430914B1/en not_active Expired - Lifetime
- 2003-12-17 DE DE60311741T patent/DE60311741T2/en not_active Expired - Lifetime
- 2003-12-17 KR KR1020030092573A patent/KR101080623B1/en not_active IP Right Cessation
- 2003-12-17 ES ES03257963T patent/ES2282578T3/en not_active Expired - Lifetime
- 2003-12-17 TW TW092135675A patent/TWI344379B/en not_active IP Right Cessation
- 2003-12-18 CA CA2453892A patent/CA2453892C/en not_active Expired - Fee Related
- 2003-12-18 CN CNB200310125500XA patent/CN1294201C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1521212A (en) | 2004-08-18 |
| EP1430914A1 (en) | 2004-06-23 |
| DE60311741T2 (en) | 2007-10-31 |
| CA2453892C (en) | 2011-11-01 |
| US6967234B2 (en) | 2005-11-22 |
| TW200422063A (en) | 2004-11-01 |
| US20040122205A1 (en) | 2004-06-24 |
| CN1294201C (en) | 2007-01-10 |
| DE60311741D1 (en) | 2007-03-29 |
| AU2003266799B2 (en) | 2009-12-10 |
| AU2003266799A1 (en) | 2004-07-08 |
| ES2282578T3 (en) | 2007-10-16 |
| KR101080623B1 (en) | 2011-11-08 |
| TWI344379B (en) | 2011-07-01 |
| KR20040054542A (en) | 2004-06-25 |
| EP1430914B1 (en) | 2007-02-14 |
| ATE353674T1 (en) | 2007-03-15 |
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| EEER | Examination request | ||
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