AU749627B2 - Use of hyaluronic acid derivatives in the preparation of biomaterials with a physical haemostatic and plugging activity and a preventive activity in the formation of adhesions following anastomosis - Google Patents
Use of hyaluronic acid derivatives in the preparation of biomaterials with a physical haemostatic and plugging activity and a preventive activity in the formation of adhesions following anastomosis Download PDFInfo
- Publication number
- AU749627B2 AU749627B2 AU92555/98A AU9255598A AU749627B2 AU 749627 B2 AU749627 B2 AU 749627B2 AU 92555/98 A AU92555/98 A AU 92555/98A AU 9255598 A AU9255598 A AU 9255598A AU 749627 B2 AU749627 B2 AU 749627B2
- Authority
- AU
- Australia
- Prior art keywords
- hyaluronic acid
- derivative
- biomaterials
- acid
- solution
- 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
Links
- 239000012620 biological material Substances 0.000 title claims abstract description 43
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims description 163
- 229940030225 antihemorrhagics Drugs 0.000 title claims description 14
- 230000000025 haemostatic effect Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 28
- 230000003872 anastomosis Effects 0.000 title abstract description 22
- 230000015572 biosynthetic process Effects 0.000 title abstract description 11
- 230000000694 effects Effects 0.000 title description 6
- 230000003449 preventive effect Effects 0.000 title description 2
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 27
- 239000005017 polysaccharide Substances 0.000 claims abstract description 27
- 150000004676 glycans Chemical class 0.000 claims abstract description 7
- 230000004888 barrier function Effects 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 136
- 229920002674 hyaluronan Polymers 0.000 claims description 135
- 229960003160 hyaluronic acid Drugs 0.000 claims description 133
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 54
- -1 aliphatic alcohols Chemical class 0.000 claims description 49
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
- 150000004804 polysaccharides Chemical class 0.000 claims description 31
- 239000001384 succinic acid Substances 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000000499 gel Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910001385 heavy metal Chemical class 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 229920002148 Gellan gum Polymers 0.000 claims description 12
- 238000001356 surgical procedure Methods 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 102000008186 Collagen Human genes 0.000 claims description 9
- 108010035532 Collagen Proteins 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 9
- 229920001436 collagen Polymers 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 235000010443 alginic acid Nutrition 0.000 claims description 8
- 229920000615 alginic acid Polymers 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 230000006870 function Effects 0.000 claims description 7
- 241000894007 species Species 0.000 claims description 7
- 229920001059 synthetic polymer Polymers 0.000 claims description 7
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 6
- 229920001817 Agar Polymers 0.000 claims description 6
- 229920000936 Agarose Polymers 0.000 claims description 6
- 229920002101 Chitin Polymers 0.000 claims description 6
- 229920001661 Chitosan Polymers 0.000 claims description 6
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 6
- 239000008272 agar Substances 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000216 gellan gum Substances 0.000 claims description 6
- 235000010492 gellan gum Nutrition 0.000 claims description 6
- 229920001206 natural gum Polymers 0.000 claims description 6
- 239000001814 pectin Substances 0.000 claims description 6
- 235000010987 pectin Nutrition 0.000 claims description 6
- 229920001285 xanthan gum Polymers 0.000 claims description 6
- 230000002785 anti-thrombosis Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical class O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 4
- 229920002230 Pectic acid Polymers 0.000 claims description 4
- 229920000954 Polyglycolide Polymers 0.000 claims description 4
- 239000000783 alginic acid Substances 0.000 claims description 4
- 229960001126 alginic acid Drugs 0.000 claims description 4
- 150000004781 alginic acids Chemical class 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 4
- 229940088710 antibiotic agent Drugs 0.000 claims description 4
- 229960004676 antithrombotic agent Drugs 0.000 claims description 4
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 239000004745 nonwoven fabric Substances 0.000 claims description 4
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 claims description 4
- 229920003175 pectinic acid Polymers 0.000 claims description 4
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 4
- 239000010318 polygalacturonic acid Substances 0.000 claims description 4
- 239000004633 polyglycolic acid Substances 0.000 claims description 4
- 239000004626 polylactic acid Substances 0.000 claims description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 108010049003 Fibrinogen Proteins 0.000 claims description 3
- 102000008946 Fibrinogen Human genes 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 108090000190 Thrombin Proteins 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 229920001222 biopolymer Polymers 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 229940012952 fibrinogen Drugs 0.000 claims description 3
- 239000003102 growth factor Substances 0.000 claims description 3
- 239000003094 microcapsule Substances 0.000 claims description 3
- 239000004005 microsphere Substances 0.000 claims description 3
- 229920005615 natural polymer Polymers 0.000 claims description 3
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 229920005749 polyurethane resin Polymers 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 229960004072 thrombin Drugs 0.000 claims description 3
- 229920001277 pectin Polymers 0.000 claims 2
- 241000722985 Fidia Species 0.000 claims 1
- 241000286819 Malo Species 0.000 claims 1
- 241000600169 Maro Species 0.000 claims 1
- 230000002792 vascular Effects 0.000 abstract description 10
- 210000001124 body fluid Anatomy 0.000 abstract description 4
- 239000010839 body fluid Substances 0.000 abstract description 4
- 239000002250 absorbent Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 231100000241 scar Toxicity 0.000 abstract description 2
- 230000002439 hemostatic effect Effects 0.000 abstract 2
- 230000009772 tissue formation Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 178
- 239000000243 solution Substances 0.000 description 130
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 235000019441 ethanol Nutrition 0.000 description 55
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 43
- 239000012153 distilled water Substances 0.000 description 42
- 238000005670 sulfation reaction Methods 0.000 description 39
- 239000002244 precipitate Substances 0.000 description 38
- 230000019635 sulfation Effects 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 27
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 15
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 15
- 210000003462 vein Anatomy 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000005119 centrifugation Methods 0.000 description 14
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 13
- 125000004494 ethyl ester group Chemical group 0.000 description 13
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 13
- 229940014800 succinic anhydride Drugs 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 12
- 238000013019 agitation Methods 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 12
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 10
- 210000001367 artery Anatomy 0.000 description 10
- 239000003456 ion exchange resin Substances 0.000 description 10
- 229920003303 ion-exchange polymer Polymers 0.000 description 10
- 229910052709 silver Inorganic materials 0.000 description 10
- 239000004332 silver Substances 0.000 description 10
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000003381 deacetylation reaction Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000011701 zinc Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229920002385 Sodium hyaluronate Polymers 0.000 description 8
- 235000019445 benzyl alcohol Nutrition 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229940010747 sodium hyaluronate Drugs 0.000 description 8
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 8
- 208000032843 Hemorrhage Diseases 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 7
- 230000000740 bleeding effect Effects 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 238000004108 freeze drying Methods 0.000 description 7
- 239000010931 gold Substances 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 7
- 230000003381 solubilizing effect Effects 0.000 description 7
- 229910052725 zinc Inorganic materials 0.000 description 7
- 208000007536 Thrombosis Diseases 0.000 description 6
- 238000002316 cosmetic surgery Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 150000003222 pyridines Chemical class 0.000 description 6
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 206010016654 Fibrosis Diseases 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229910001923 silver oxide Inorganic materials 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 230000035322 succinylation Effects 0.000 description 5
- 238000010613 succinylation reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 241000786363 Rhampholeon spectrum Species 0.000 description 4
- 238000006640 acetylation reaction Methods 0.000 description 4
- 239000003146 anticoagulant agent Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 230000004761 fibrosis Effects 0.000 description 4
- 229960002442 glucosamine Drugs 0.000 description 4
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 4
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 210000003141 lower extremity Anatomy 0.000 description 4
- 238000002278 reconstructive surgery Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- 150000003751 zinc Chemical class 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 101710134784 Agnoprotein Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003047 N-acetyl group Chemical group 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229940014041 hyaluronate Drugs 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 3
- 230000001180 sulfating effect Effects 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 230000003878 venous anastomosis Effects 0.000 description 3
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- PAPMYQLKLNRZIR-UHFFFAOYSA-N Cotarnine Chemical compound C1CN(C)C(O)C2=C1C=C1OCOC1=C2OC PAPMYQLKLNRZIR-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 206010018852 Haematoma Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 230000003881 arterial anastomosis Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 210000001520 comb Anatomy 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000003527 fibrinolytic agent Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 2
- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 1
- KIUKXJAPPMFGSW-YXBJCWEESA-N (2s,4s,5r,6s)-6-[(2s,3r,5s,6r)-3-acetamido-2-[(3s,4r,5r,6r)-6-[(3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@@H]3[C@@H]([C@@H](O)C(O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)C(C(O)=O)O1 KIUKXJAPPMFGSW-YXBJCWEESA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 1
- KLTIMEXKPRJOIS-UHFFFAOYSA-N 2-chloro-1-methyl-2H-pyridine hydroiodide Chemical compound I.CN1C=CC=CC1Cl KLTIMEXKPRJOIS-UHFFFAOYSA-N 0.000 description 1
- RPHLQSHHTJORHI-UHFFFAOYSA-N Adrenochrome Chemical compound O=C1C(=O)C=C2N(C)CC(O)C2=C1 RPHLQSHHTJORHI-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 108010027612 Batroxobin Proteins 0.000 description 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
- 101100115778 Caenorhabditis elegans dac-1 gene Proteins 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- HBGOLJKPSFNJSD-UHFFFAOYSA-N Etamsylate Chemical compound CC[NH2+]CC.OC1=CC=C(O)C(S([O-])(=O)=O)=C1 HBGOLJKPSFNJSD-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- 229920002201 Oxidized cellulose Polymers 0.000 description 1
- 102000007079 Peptide Fragments Human genes 0.000 description 1
- 108010033276 Peptide Fragments Proteins 0.000 description 1
- 229920000331 Polyhydroxybutyrate Polymers 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 208000031737 Tissue Adhesions Diseases 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 1
- 102000002852 Vasopressins Human genes 0.000 description 1
- 108010004977 Vasopressins Proteins 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000000061 acid fraction Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 229960002892 adrenalone Drugs 0.000 description 1
- PZMVOUYYNKPMSI-UHFFFAOYSA-N adrenalone Chemical compound CNCC(=O)C1=CC=C(O)C(O)=C1 PZMVOUYYNKPMSI-UHFFFAOYSA-N 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 229960002210 batroxobin Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229950006142 carbazochrome salicylate Drugs 0.000 description 1
- 229960004353 carbazochrome sodium sulfonate Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000000064 cholinergic agonist Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000012321 colectomy Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000000600 disaccharide group Chemical group 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosanyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 1
- XDEURYRPQDIBSL-UHFFFAOYSA-N dopaminechrome (keto form) Chemical compound O=C1C(=O)C=C2CCNC2=C1 XDEURYRPQDIBSL-UHFFFAOYSA-N 0.000 description 1
- 238000012976 endoscopic surgical procedure Methods 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 229940011899 ethamsylate Drugs 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 150000002302 glucosamines Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002406 microsurgery Methods 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- KDZPIXVLPYVHDO-UHFFFAOYSA-N oxamarin Chemical compound O1C(=O)C=C(C)C2=C1C=C(OCCN(CC)CC)C(OCCN(CC)CC)=C2 KDZPIXVLPYVHDO-UHFFFAOYSA-N 0.000 description 1
- 229950005161 oxamarin Drugs 0.000 description 1
- 229940107304 oxidized cellulose Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940043200 pentothal Drugs 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000005015 poly(hydroxybutyrate) Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000250 revascularization Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000036573 scar formation Effects 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HLFCZZKCHVSOAP-WXIWBVQFSA-M sodium;(5e)-5-(carbamoylhydrazinylidene)-1-methyl-6-oxo-2,3-dihydroindole-2-sulfonate Chemical compound [Na+].NC(=O)N\N=C/1C(=O)C=C2N(C)C(S([O-])(=O)=O)CC2=C\1 HLFCZZKCHVSOAP-WXIWBVQFSA-M 0.000 description 1
- CELKBRMLNUNCIP-HTFHIHPASA-M sodium;2-hydroxybenzoate;[(e)-(3-hydroxy-1-methyl-6-oxo-2,3-dihydroindol-5-ylidene)amino]urea Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O.NC(=O)N\N=C/1C(=O)C=C2N(C)CC(O)C2=C\1 CELKBRMLNUNCIP-HTFHIHPASA-M 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- SZNQDPUZKFSCNG-UHFFFAOYSA-N sulmarin Chemical compound C1=C(OS(O)(=O)=O)C(OS(O)(=O)=O)=CC2=C1OC(=O)C=C2C SZNQDPUZKFSCNG-UHFFFAOYSA-N 0.000 description 1
- 229950010209 sulmarin Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000002885 thrombogenetic effect Effects 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229960001555 tolonium chloride Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 235000019143 vitamin K2 Nutrition 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
- 239000003357 wound healing promoting agent Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 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
- 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
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- 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
- A61L31/04—Macromolecular materials
- A61L31/041—Mixtures of macromolecular compounds
-
- 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
- A61L31/04—Macromolecular materials
- A61L31/042—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/418—Agents promoting blood coagulation, blood-clotting agents, embolising agents
-
- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/04—Materials for stopping bleeding
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Surgery (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITPD97A000170 | 1997-07-28 | ||
| IT97PD000170A IT1294797B1 (it) | 1997-07-28 | 1997-07-28 | Uso dei derivati dell'acido ialuronico nella preparazione di biomateriali aventi attivita' emostatica fisica e tamponante |
| PCT/EP1998/004716 WO1999004828A2 (en) | 1997-07-28 | 1998-07-28 | Use of hyaluronic acid derivatives in the preparation of biomaterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU9255598A AU9255598A (en) | 1999-02-16 |
| AU749627B2 true AU749627B2 (en) | 2002-06-27 |
Family
ID=11391877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU92555/98A Ceased AU749627B2 (en) | 1997-07-28 | 1998-07-28 | Use of hyaluronic acid derivatives in the preparation of biomaterials with a physical haemostatic and plugging activity and a preventive activity in the formation of adhesions following anastomosis |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7202230B2 (enExample) |
| EP (1) | EP0999859B1 (enExample) |
| JP (1) | JP4417547B2 (enExample) |
| AT (1) | ATE311208T1 (enExample) |
| AU (1) | AU749627B2 (enExample) |
| CA (1) | CA2298733C (enExample) |
| DE (1) | DE69832616T2 (enExample) |
| DK (1) | DK0999859T3 (enExample) |
| ES (1) | ES2253827T3 (enExample) |
| IL (2) | IL134140A0 (enExample) |
| IT (1) | IT1294797B1 (enExample) |
| WO (1) | WO1999004828A2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1306679B1 (it) * | 1999-06-29 | 2001-10-02 | Fidia Advanced Biopolymers Srl | Uso dei derivati dell'acido ialuronico per la preparazione dicomposizoni farmaceutiche e biomateriali per la prevenzione della |
| WO2001097826A2 (en) * | 2000-06-16 | 2001-12-27 | University Of Medicine And Dentistry Of New Jersey | Hemostatic compositions, devices and methods |
| US7094428B2 (en) | 2000-06-16 | 2006-08-22 | The University Of Medicine And Dentistry Of New Jersey | Hemostatic compositions, devices and methods |
| US6235796B1 (en) * | 2000-06-26 | 2001-05-22 | Sarfaraz K. Niazi | Use of fluorocarbons for the prevention of surgical adhesions |
| EP1659143A4 (en) * | 2003-07-28 | 2008-10-08 | Teijin Ltd | HYDROGEL SENSITIVE AT TEMPERATURE |
| DE10349722A1 (de) * | 2003-10-23 | 2005-06-16 | Beschorner, Katharina, Dr. | Zusammensetzung zur Arthrose-/Arthritisbehandlung, insbesondere von Gelenken |
| RU2369408C2 (ru) * | 2004-07-09 | 2009-10-10 | Ферросан А/С | Гемостатическая композиция, включающая гиалуроновую кислоту |
| ITPD20040245A1 (it) * | 2004-10-08 | 2005-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali costituiti da acido ialuronico solfatato e gellano utilizzabili nella prevenzione delle adesioni spinali |
| DE602005009978D1 (de) * | 2004-12-14 | 2008-11-06 | Fidia Advanced Biopolymers Srl | Verfahren zur herstellung von zwei- und dreidimensionalen polymergerüsten |
| ITPD20040312A1 (it) * | 2004-12-15 | 2005-03-15 | Fidia Advanced Biopolymers Srl | Protesi e o supporto per la sostituzione, riparazione, rigenerazione del menisco |
| ITPD20050206A1 (it) | 2005-07-07 | 2007-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali in forma di fibra da impiegarsi come dispositivi medici nel trattamento delle ferite e loro processi di produzione |
| ITMI20051415A1 (it) * | 2005-07-22 | 2007-01-23 | Fidia Advanced Biopolymers Srl | Biomateriali a base di corbossimetilcellulosa salificata con zinco associata a derivati dell'acido ialuronico da impiegarsi come dispositivi medici con attivita' antimicrobica ed antifungina e loro processo di produzione |
| WO2007103993A2 (en) * | 2006-03-07 | 2007-09-13 | Axle International | Bioactive scaffold for therapeutic and adhesion prevention applications |
| ITPD20060219A1 (it) | 2006-05-31 | 2007-12-01 | Fidia Farmaceutici | Composizioni farmaceutiche contenenti acido ialuronico solfatato nel trattamento dell'osteoartrosi |
| CA2716872C (en) | 2008-02-29 | 2015-02-10 | Ferrosan Medical Devices A/S | Device for promotion of hemostasis and/or wound healing |
| US8343942B2 (en) | 2008-04-04 | 2013-01-01 | University Of Utah Research Foundation | Methods for treating interstitial cystitis |
| JP5758797B2 (ja) | 2008-04-04 | 2015-08-05 | ユニバーシティ・オブ・ユタ・リサーチ・ファウンデイション | アルキル化半合成グリコサミノグリカンエーテルならびにその製造および使用方法 |
| EP2324064B1 (en) * | 2008-09-02 | 2017-11-08 | Tautona Group LP | Threads of hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
| TWI458833B (zh) | 2010-05-11 | 2014-11-01 | Univ China Medical | 奈米金屬分散液及其製法 |
| JP6062917B2 (ja) | 2011-03-23 | 2017-01-18 | ザ ユニバーシティ オブ ユタ リサーチ ファウンデイション | 泌尿器科の炎症の治療及び予防の方法 |
| CA2865349C (en) | 2012-03-06 | 2021-07-06 | Ferrosan Medical Devices A/S | Pressurized container containing haemostatic paste |
| RU2636240C2 (ru) | 2012-06-12 | 2017-11-21 | Ферросан Медикал Дивайсиз А/С | Сухая гемостатическая композиция |
| EP3010419B1 (en) | 2013-06-21 | 2020-05-20 | Ferrosan Medical Devices A/S | Vacuum expanded dry composition and syringe for retaining same |
| BR112016013322B1 (pt) | 2013-12-11 | 2020-07-21 | Ferrosan Medical Devices A/S | métodos para preparação de uma composição seca e para reconstituir uma composição seca, composição seca, uso de uma composição seca, e, kit |
| SMT202200083T1 (it) | 2014-02-27 | 2022-03-21 | Synartro Ab | Coniugati di ialuronano con sostanze farmaceuticamente attive, metodi e composizioni |
| RU2715235C2 (ru) | 2014-10-13 | 2020-02-26 | Ферросан Медикал Дивайсиз А/С | Сухая композиция для использования при гемостазе и заживлении ран |
| CA2970710A1 (en) | 2014-12-24 | 2016-06-30 | Ferrosan Medical Devices A/S | Syringe for retaining and mixing first and second substances |
| CN107771093B (zh) | 2015-07-03 | 2021-06-15 | 弗罗桑医疗设备公司 | 用于混合两种组分和用于在存储条件下保持真空的注射器 |
| KR20180027126A (ko) * | 2016-09-06 | 2018-03-14 | (주)한국비엠아이 | 가교화 히알루론산 유도체 매트릭스가 포함된 지혈 조성물 |
| WO2018053111A1 (en) | 2016-09-15 | 2018-03-22 | University Of Utah Research Foundation | In situ gelling compositions for the treatment or prevention of inflammation and tissue damage |
| CN112368028A (zh) | 2018-05-09 | 2021-02-12 | 弗罗桑医疗设备公司 | 用于制备止血组合物的方法 |
| CN111228653A (zh) | 2018-11-13 | 2020-06-05 | 格莱科米拉治疗公司 | 用电离辐射加强癌症治疗的方法 |
| KR101980063B1 (ko) * | 2019-01-25 | 2019-05-17 | 주식회사 휴메딕스 | 히알루론산을 포함하는 스펀지형 생분해성 지혈제 조성물 |
| CN113754795B (zh) * | 2021-10-19 | 2023-03-10 | 澳门大学 | 磺酸化透明质酸类化合物、其制备方法及其应用 |
| CN116688216A (zh) * | 2023-05-26 | 2023-09-05 | 北京福爱乐科技发展有限公司 | 一种生物可降解医用凝胶及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992020349A1 (en) * | 1991-05-20 | 1992-11-26 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| WO1995025751A1 (en) * | 1994-03-23 | 1995-09-28 | Fidia Advanced Biopolymers Srl | Novel heparin-like sulfated polysaccharides |
| WO1997007833A2 (en) * | 1995-08-29 | 1997-03-06 | Fidia Advanced Biopolymers, S.R.L. | Biomaterials for preventing post-surgical adhesions comprised of hyaluronic acid derivatives |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| US5202431A (en) | 1985-07-08 | 1993-04-13 | Fidia, S.P.A. | Partial esters of hyaluronic acid |
| IT1203814B (it) | 1986-06-30 | 1989-02-23 | Fidia Farmaceutici | Esteri dell'acido alginico |
| IT1198449B (it) | 1986-10-13 | 1988-12-21 | F I D I Farmaceutici Italiani | Esteri di alcoli polivalenti di acido ialuronico |
| IT1219587B (it) * | 1988-05-13 | 1990-05-18 | Fidia Farmaceutici | Polisaccaridi carbossiilici autoreticolati |
| GB8911177D0 (en) * | 1989-05-16 | 1989-07-05 | Vilain Jean | Alginate gel pharmaceutical product |
| IT1247157B (it) | 1991-02-11 | 1994-12-12 | Fidia Spa | Canali di guida biodegradabili e bioassorbibili da impiegare per la rigenerazione nervosa. |
| US5332809A (en) | 1991-02-11 | 1994-07-26 | Fidia S.P.A. | Partial esters of gellan |
| GB9109367D0 (en) * | 1991-05-01 | 1991-06-26 | Merck Sharp & Dohme | Surgical dressing |
| IT1247472B (it) | 1991-05-31 | 1994-12-17 | Fidia Spa | Processo per la preparazione di microsfere contenenti componenti biologicamente attivi. |
| IT1254704B (it) | 1991-12-18 | 1995-10-09 | Mini Ricerca Scient Tecnolog | Tessuto non tessuto essenzialmente costituito da derivati dell'acido ialuronico |
| IT1264322B (it) | 1992-07-30 | 1996-09-23 | Lanfranco Callegaro | Esteri di gellano autoreticolato, procedimento di preparazione e loro applicazioni farmaceutiche e biomedico-sanitarie |
| IT1259141B (it) | 1992-08-03 | 1996-03-11 | Fidia Spa | Canali di guida biodegradabili e bioriassorbibili da impiegare per la riparazione tissutale come adiuvante in interventi chirurgici |
| FR2723847A1 (fr) * | 1994-08-29 | 1996-03-01 | Debiopharm Sa | Compositions antithrombotiques et non hemorragiques a base d'heparine, procede pour leur preparation et applications therapeutiques. |
| IT1281877B1 (it) * | 1995-05-10 | 1998-03-03 | Fidia Advanced Biopolymers Srl | Sali di metalli pesanti di succinil derivati dell'acido ialuronico e loro impiego come potenziali agenti terapeutici |
| GB9514361D0 (en) * | 1995-07-13 | 1995-09-13 | Bristol Myers Squibb Co | A film for topical use in the treatment of wounds |
| IT1282994B1 (it) * | 1996-05-10 | 1998-04-03 | Inalco Spa | Derivati del polisaccaride k5 aventi elevata attivita' anticoagulante |
| IT1287698B1 (it) | 1996-08-29 | 1998-08-18 | Fidia Advanced Biopolymers Srl | Fili da sutura essenzialmente costituiti da derivati esterei dello acido ialuronico |
-
1997
- 1997-07-28 IT IT97PD000170A patent/IT1294797B1/it active IP Right Grant
-
1998
- 1998-07-28 EP EP98945104A patent/EP0999859B1/en not_active Expired - Lifetime
- 1998-07-28 ES ES98945104T patent/ES2253827T3/es not_active Expired - Lifetime
- 1998-07-28 WO PCT/EP1998/004716 patent/WO1999004828A2/en not_active Ceased
- 1998-07-28 AT AT98945104T patent/ATE311208T1/de active
- 1998-07-28 CA CA002298733A patent/CA2298733C/en not_active Expired - Lifetime
- 1998-07-28 IL IL13414098A patent/IL134140A0/xx active IP Right Grant
- 1998-07-28 JP JP2000503879A patent/JP4417547B2/ja not_active Expired - Fee Related
- 1998-07-28 AU AU92555/98A patent/AU749627B2/en not_active Ceased
- 1998-07-28 DE DE69832616T patent/DE69832616T2/de not_active Expired - Lifetime
- 1998-07-28 DK DK98945104T patent/DK0999859T3/da active
-
2000
- 2000-01-20 IL IL134140A patent/IL134140A/en not_active IP Right Cessation
-
2002
- 2002-05-07 US US10/139,878 patent/US7202230B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992020349A1 (en) * | 1991-05-20 | 1992-11-26 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| WO1995025751A1 (en) * | 1994-03-23 | 1995-09-28 | Fidia Advanced Biopolymers Srl | Novel heparin-like sulfated polysaccharides |
| WO1997007833A2 (en) * | 1995-08-29 | 1997-03-06 | Fidia Advanced Biopolymers, S.R.L. | Biomaterials for preventing post-surgical adhesions comprised of hyaluronic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1294797B1 (it) | 1999-04-15 |
| ES2253827T3 (es) | 2006-06-01 |
| WO1999004828A3 (en) | 1999-06-10 |
| AU9255598A (en) | 1999-02-16 |
| DE69832616T2 (de) | 2006-08-17 |
| US20030060448A1 (en) | 2003-03-27 |
| CA2298733A1 (en) | 1999-02-04 |
| ITPD970170A1 (it) | 1999-01-28 |
| JP4417547B2 (ja) | 2010-02-17 |
| IL134140A (en) | 2006-08-20 |
| CA2298733C (en) | 2009-09-01 |
| EP0999859B1 (en) | 2005-11-30 |
| EP0999859A2 (en) | 2000-05-17 |
| HK1028210A1 (en) | 2001-02-09 |
| IL134140A0 (en) | 2001-04-30 |
| JP2001510713A (ja) | 2001-08-07 |
| WO1999004828A2 (en) | 1999-02-04 |
| ATE311208T1 (de) | 2005-12-15 |
| DK0999859T3 (da) | 2006-03-27 |
| US7202230B2 (en) | 2007-04-10 |
| DE69832616D1 (de) | 2006-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU749627B2 (en) | Use of hyaluronic acid derivatives in the preparation of biomaterials with a physical haemostatic and plugging activity and a preventive activity in the formation of adhesions following anastomosis | |
| AU738788B2 (en) | N-sulphated hyaluronic acid compounds, derivatives thereof and a process for their preparation | |
| US5502042A (en) | Methods and compositions for treating wounds | |
| US7345117B1 (en) | Sulphated hyaluronic acid and sulphated derivatives thereof covalently bound to polyurethanes, and the process for their preparation | |
| CZ20011650A3 (cs) | Zesítěné hyaluronové kyseliny | |
| IL140604A (en) | Amides of hyaluronic acid and the derivatives thereof and a process for their preparation | |
| JP2008302235A (ja) | ヒアルロン酸誘導体からなる術後癒着予防用生体適合材料 | |
| Chen et al. | An aminocaproic acid-grafted chitosan derivative with superior antibacterial and hemostatic properties for the prevention of secondary bleeding | |
| US20100260845A1 (en) | Biocompatible and Biodegradable Biopolymer Matrix | |
| MXPA00001044A (es) | Uso de derivados de acido hialuronico en la preparacion de biomateriales con una actividad hemostatica fisica y obturadora, y una actividad preventiva en la formacion de adhesiones enseguida de anastomosis | |
| HK1028210B (en) | Use of hyaluronic acid derivatives in the preparation of biomaterials | |
| JPH03165775A (ja) | サクシニルキトサンより構成された医用材料 | |
| Widiyanti et al. | Synthesis and characterization of cryogel apple pectin-chitosan as physical barrier intraperitoneal antiadhesion postsurgical | |
| de la Harpe | A 3D Monofilament Biosuture for Microvascular Surgery Applications | |
| EP2637712B1 (en) | Biocompatible and biodegradable composite material for use in surgery and process for production thereof | |
| HK1025105B (en) | N-sulphated hyaluronic acid compounds, derivatives thereof and a process for their preparation | |
| JPH01303152A (ja) | 止血材およびその製造法 | |
| ITPD980022A1 (it) | Composti n-solfatati dell'acido ialuronico e dei suoi derivati ad atti vita' anticoagualante e antitrombotica e processo per la preparazione | |
| MXPA01004712A (en) | Cross-linked hyaluronic acids and medical uses thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |