ZA200103800B - Cross-linking process of carboxylated polysaccharides. - Google Patents
Cross-linking process of carboxylated polysaccharides. Download PDFInfo
- Publication number
- ZA200103800B ZA200103800B ZA200103800A ZA200103800A ZA200103800B ZA 200103800 B ZA200103800 B ZA 200103800B ZA 200103800 A ZA200103800 A ZA 200103800A ZA 200103800 A ZA200103800 A ZA 200103800A ZA 200103800 B ZA200103800 B ZA 200103800B
- Authority
- ZA
- South Africa
- Prior art keywords
- cross
- process according
- polysaccharide
- carboxy
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 229920001282 polysaccharide Polymers 0.000 title claims description 29
- 239000005017 polysaccharide Substances 0.000 title claims description 29
- 238000004132 cross linking Methods 0.000 title claims description 27
- 230000008569 process Effects 0.000 title claims description 25
- 150000004676 glycans Chemical class 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
- 150000004804 polysaccharides Chemical class 0.000 claims description 26
- 229920002674 hyaluronan Polymers 0.000 claims description 20
- -1 hydroxy, carboxy Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- AONKRVVHOIQJQI-UHFFFAOYSA-M 3-(chloromethyl)-2h-pyridin-2-ylium;iodide Chemical compound [I-].ClCC1=CC=CN=[C+]1 AONKRVVHOIQJQI-UHFFFAOYSA-M 0.000 claims description 11
- 229920000768 polyamine Polymers 0.000 claims description 7
- 229920000615 alginic acid Polymers 0.000 claims description 6
- 235000010443 alginic acid Nutrition 0.000 claims description 6
- 150000004781 alginic acids Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- JFOIBTLTZWOAIC-UHFFFAOYSA-N (4-nitrophenyl) 2,2,2-trifluoroacetate Chemical compound [O-][N+](=O)C1=CC=C(OC(=O)C(F)(F)F)C=C1 JFOIBTLTZWOAIC-UHFFFAOYSA-N 0.000 claims description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims description 2
- 229920001661 Chitosan Polymers 0.000 claims description 2
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 2
- 229920000045 Dermatan sulfate Polymers 0.000 claims description 2
- 229920001503 Glucan Polymers 0.000 claims description 2
- 229920002971 Heparan sulfate Polymers 0.000 claims description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- QJDRFICTELBSSO-UHFFFAOYSA-N triazol-4-ylidenemethanone Chemical compound O=C=C1C=NN=N1 QJDRFICTELBSSO-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 238000005670 sulfation reaction Methods 0.000 claims 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 238000010668 complexation reaction Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000019635 sulfation Effects 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 229960003160 hyaluronic acid Drugs 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 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 compound 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 description 12
- 239000000499 gel Substances 0.000 description 11
- 229920002521 macromolecule Polymers 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000012190 activator Substances 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 150000002016 disaccharides Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000783 alginic acid Substances 0.000 description 3
- 229960001126 alginic acid Drugs 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
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- 239000011347 resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229920002385 Sodium hyaluronate Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229940010747 sodium hyaluronate Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 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 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 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
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 1
- OCFTWDXITKPTCK-UHFFFAOYSA-N 3-(chloromethyl)-2h-pyridin-2-ylium Chemical compound ClCC1=CC=CN=[C+]1 OCFTWDXITKPTCK-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 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 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 239000002250 absorbent Substances 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- 239000007810 chemical reaction solvent Substances 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- 238000009826 distribution Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/005—Crosslinking of cellulose derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/003—Crosslinking of starch
- C08B31/006—Crosslinking of derivatives of starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0084—Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Cosmetics (AREA)
- Materials For Medical Uses (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1998MI002443A IT1303738B1 (it) | 1998-11-11 | 1998-11-11 | Processo di reticolazione di polisaccaridi carbossilati. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200103800B true ZA200103800B (en) | 2002-06-10 |
Family
ID=11381036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200103800A ZA200103800B (en) | 1998-11-11 | 2001-05-10 | Cross-linking process of carboxylated polysaccharides. |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US6734298B1 (zh) |
| EP (1) | EP1137670B1 (zh) |
| JP (1) | JP2002529549A (zh) |
| KR (1) | KR100685454B1 (zh) |
| CN (1) | CN1144818C (zh) |
| AT (1) | ATE291590T1 (zh) |
| AU (1) | AU756158B2 (zh) |
| BR (1) | BR9915238A (zh) |
| CA (1) | CA2350665A1 (zh) |
| CZ (1) | CZ303485B6 (zh) |
| DE (1) | DE69924407T2 (zh) |
| DK (1) | DK1137670T3 (zh) |
| ES (1) | ES2237971T3 (zh) |
| HK (1) | HK1041010B (zh) |
| HU (1) | HU227731B1 (zh) |
| IL (1) | IL143064A0 (zh) |
| IT (1) | IT1303738B1 (zh) |
| NO (1) | NO20012316L (zh) |
| NZ (1) | NZ511308A (zh) |
| PT (1) | PT1137670E (zh) |
| RU (1) | RU2230073C2 (zh) |
| SI (1) | SI1137670T1 (zh) |
| TR (1) | TR200101325T2 (zh) |
| WO (1) | WO2000027886A1 (zh) |
| ZA (1) | ZA200103800B (zh) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITPD980037A1 (it) * | 1998-02-25 | 1999-08-25 | Fidia Advanced Biopolymers Srl | Acido ialuronico solfatato e i suoi derivati legati covalentemente a polimeri sintetici pe la preparazione di biomateriali e per il rivesti |
| IT1303738B1 (it) | 1998-11-11 | 2001-02-23 | Aquisitio S P A | Processo di reticolazione di polisaccaridi carbossilati. |
| IT1303735B1 (it) * | 1998-11-11 | 2001-02-23 | Falorni Italia Farmaceutici S | Acidi ialuronici reticolati e loro usi medici. |
| FR2799196B1 (fr) * | 1999-10-04 | 2002-02-08 | Sod Conseils Rech Applic | Copolymeres reticules a base de copolymeres polycarboxyliques non reticules |
| KR100375299B1 (ko) * | 2000-10-10 | 2003-03-10 | 주식회사 엘지생명과학 | 히알루론산의 가교결합형 아마이드 유도체와 이의 제조방법 |
| US6500947B1 (en) | 2001-08-24 | 2002-12-31 | Weyerhaeuser Company | Superabsorbent polymer |
| KR100493461B1 (ko) * | 2002-02-27 | 2005-06-07 | 재단법인서울대학교산학협력재단 | 접착분자가 부착된 천연고분자, 그의 제조방법 및 그의 용도 |
| FR2839312A1 (fr) * | 2002-05-03 | 2003-11-07 | Roquette Freres | Procede de transformation de matieres amylacees par traitement thermique, en l'absence de solvant, en phase ou semi-seche |
| KR20040009891A (ko) * | 2002-07-26 | 2004-01-31 | 주식회사 엘지생명과학 | 히알루론산의 유도체 겔 및 그 제조방법 |
| KR100523953B1 (ko) * | 2002-08-27 | 2005-10-25 | 주식회사 엘지생명과학 | 천연다당류와 히알루론산의 마이크로비드 및 이의 제조 방법 |
| DE10256558A1 (de) * | 2002-12-04 | 2004-09-16 | Supramol Parenteral Colloids Gmbh | Ester von Polysaccharid Aldonsäuren, Verfahren zu ihrer Herstellung und Verwendung zur Kopplung an pharmazeutische Wirkstoffe |
| US7485719B2 (en) | 2003-02-21 | 2009-02-03 | Terumo Kabushiki Kaisha | Crosslinkable polysaccharide derivative, process for producing the same, crosslinkable polysaccharide composition, and medical treatment material |
| FR2861734B1 (fr) | 2003-04-10 | 2006-04-14 | Corneal Ind | Reticulation de polysaccharides de faible et forte masse moleculaire; preparation d'hydrogels monophasiques injectables; polysaccharides et hydrogels obtenus |
| JP4669919B2 (ja) * | 2003-06-06 | 2011-04-13 | コスモテック株式会社 | 医療用組成物 |
| JP2007526941A (ja) | 2004-02-23 | 2007-09-20 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | バイオマス由来材料を含有する架橋ポリマー |
| WO2005087289A1 (ja) * | 2004-03-15 | 2005-09-22 | Terumo Kabushiki Kaisha | 癒着防止材 |
| EP1769004B1 (de) * | 2004-06-21 | 2017-08-09 | Evonik Degussa GmbH | Wasserabsorbierendes polysaccharid sowie ein verfahren zu seiner herstellung |
| ITMI20041373A1 (it) | 2004-07-09 | 2004-10-09 | Lima Lto S P A | N-metil-ammidi di carbossimetilcellulosa acido alginico o carbossimetalamido |
| US7541396B2 (en) | 2004-12-29 | 2009-06-02 | Weyerhaeuser Nr Company | Method for making carboxyalkyl cellulose |
| US7393905B2 (en) * | 2004-12-29 | 2008-07-01 | Weyerhaeuser Company | Crosslinked mixed carboxylated polymer network |
| US7230049B2 (en) * | 2004-12-29 | 2007-06-12 | Weyerhaeuser Co. | Method of crosslinking a carboxylated polymer using a triazine crosslinking activator |
| US7241836B2 (en) * | 2004-12-29 | 2007-07-10 | Weyerhaeuser Co. | Method of crosslinking a mixture of carboxylated polymers using a triazine crosslinking activator |
| US20060142476A1 (en) * | 2004-12-29 | 2006-06-29 | Weerawarna S A | Crosslinked carboxylated polymer |
| US7300965B2 (en) | 2004-12-29 | 2007-11-27 | Weyerhaeuser Company | Mixed polymer network |
| RU2472809C2 (ru) * | 2005-09-02 | 2013-01-20 | Колбар Лайфсайенс Лтд. | Поперечно сшитые полисахаридные и белковые матрицы и способы их получения |
| AU2007329435B2 (en) * | 2006-12-04 | 2013-06-06 | Johns Hopkins University | Imidated biopolymer adhesive and hydrogel |
| KR100825519B1 (ko) | 2007-01-05 | 2008-04-25 | 주식회사 바이오폴리메드 | 키토산 기재 고분자 접합체 및 그 제조방법 |
| US20080293637A1 (en) * | 2007-05-23 | 2008-11-27 | Allergan, Inc. | Cross-linked collagen and uses thereof |
| US20110077737A1 (en) * | 2007-07-30 | 2011-03-31 | Allergan, Inc. | Tunably Crosslinked Polysaccharide Compositions |
| US8697044B2 (en) | 2007-10-09 | 2014-04-15 | Allergan, Inc. | Crossed-linked hyaluronic acid and collagen and uses thereof |
| SI2818184T1 (sl) | 2007-11-16 | 2019-03-29 | Aclaris Therapeutics, Inc. | Sestava in postopki za zdravljenje purpure |
| US8394784B2 (en) | 2007-11-30 | 2013-03-12 | Allergan, Inc. | Polysaccharide gel formulation having multi-stage bioactive agent delivery |
| US8394782B2 (en) | 2007-11-30 | 2013-03-12 | Allergan, Inc. | Polysaccharide gel formulation having increased longevity |
| US8357795B2 (en) | 2008-08-04 | 2013-01-22 | Allergan, Inc. | Hyaluronic acid-based gels including lidocaine |
| EP3184552B1 (en) | 2008-09-02 | 2020-08-12 | Tautona Group LP | Threads of hyaluronic acid, methods of making thereof and uses thereof |
| US8361926B2 (en) | 2008-11-25 | 2013-01-29 | Evonik Stockhausen, Llc | Water-absorbing polysaccharide and method for producing the same |
| DK2413894T3 (en) * | 2009-04-02 | 2017-04-03 | Allergan Inc | HIGHLY FORMED HYDROGLES FOR SOFTWARE STRENGTH |
| US9114188B2 (en) | 2010-01-13 | 2015-08-25 | Allergan, Industrie, S.A.S. | Stable hydrogel compositions including additives |
| US20110172180A1 (en) | 2010-01-13 | 2011-07-14 | Allergan Industrie. Sas | Heat stable hyaluronic acid compositions for dermatological use |
| JP5749283B2 (ja) | 2010-03-12 | 2015-07-15 | アラーガン・アンデュストリー・ソシエテ・パール・アクシオン・サンプリフィエＡｌｌｅｒｇａｎ Ｉｎｄｕｓｔｒｉｅ Ｓａｓ | 皮膚状態を改善するための流体組成物 |
| DK3078388T3 (da) | 2010-03-22 | 2019-05-20 | Allergan Inc | Tværbundne hydrogeler til blødvævsforøgelse |
| EP2600858A4 (en) * | 2010-08-04 | 2014-03-05 | Tixupharma | SUPRAMOLECULAR COMPLEXES OF POLYANIONIC POLYMERS AND SPERMIDINE FOR WOVEN CARE AND REPAIR |
| US8697057B2 (en) | 2010-08-19 | 2014-04-15 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US8883139B2 (en) | 2010-08-19 | 2014-11-11 | Allergan Inc. | Compositions and soft tissue replacement methods |
| US9005605B2 (en) | 2010-08-19 | 2015-04-14 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US8889123B2 (en) | 2010-08-19 | 2014-11-18 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US9393263B2 (en) | 2011-06-03 | 2016-07-19 | Allergan, Inc. | Dermal filler compositions including antioxidants |
| US9408797B2 (en) | 2011-06-03 | 2016-08-09 | Allergan, Inc. | Dermal filler compositions for fine line treatment |
| CN107412002A (zh) | 2011-06-03 | 2017-12-01 | 阿勒根公司 | 包括抗氧化剂的皮肤填充剂组合物 |
| US20130096081A1 (en) | 2011-06-03 | 2013-04-18 | Allergan, Inc. | Dermal filler compositions |
| US20130244943A1 (en) | 2011-09-06 | 2013-09-19 | Allergan, Inc. | Hyaluronic acid-collagen matrices for dermal filling and volumizing applications |
| US9662422B2 (en) | 2011-09-06 | 2017-05-30 | Allergan, Inc. | Crosslinked hyaluronic acid-collagen gels for improving tissue graft viability and soft tissue augmentation |
| CN103113495A (zh) * | 2013-02-03 | 2013-05-22 | 江苏天竹化工科技有限公司 | 一种可光聚合透明质酸衍生物及其制备方法 |
| ITUD20130119A1 (it) * | 2013-09-12 | 2015-03-13 | Limacorporate Spa | Idrogel biocompatibile per uso biomedico o farmaceutico, polimero intermedio per realizzare detto idrogel biocompatibile e relativo metodo di realizzazione |
| ES2811269T3 (es) | 2014-01-31 | 2021-03-11 | Seikagaku Kogyo Co Ltd | Agente de reticulación de diamina, cuerpo reticulado de polisacárido ácido y material médico |
| WO2016051219A1 (en) | 2014-09-30 | 2016-04-07 | Allergan Industrie, Sas | Stable hydrogel compositions including additives |
| JP6110037B2 (ja) | 2015-01-16 | 2017-04-05 | 生化学工業株式会社 | コンドロイチン硫酸架橋体、並びにこれを含有する組成物、及び眼疾患処置剤 |
| WO2016128783A1 (en) | 2015-02-09 | 2016-08-18 | Allergan Industrie Sas | Compositions and methods for improving skin appearance |
| CN107207627B (zh) | 2015-02-27 | 2022-05-24 | 学校法人常翔学园 | 具有膜透过性肽链的多糖衍生物 |
| US20180086852A1 (en) * | 2015-03-31 | 2018-03-29 | Kewpie Corporation | Hyaluronic Acid Derivative and Manufacturing Method Therefor and Cosmetics, Food Composition, and Pharmaceutical Composition Containing Hyaluronic Acid Derivative |
| CZ306479B6 (cs) * | 2015-06-15 | 2017-02-08 | Contipro A.S. | Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin |
| GB201511218D0 (en) | 2015-06-25 | 2015-08-12 | Goe Ip As | Reservoir treatments |
| CN105566511B (zh) * | 2016-01-27 | 2017-11-03 | 天津医科大学 | 电荷翻转普鲁兰多糖衍生物及其合成方法和用途 |
| CN110961057A (zh) * | 2020-01-16 | 2020-04-07 | 江苏罗格斯生物科技有限公司 | 一种绿色生物水凝胶输送系统及其制备方法 |
| RU2743941C1 (ru) * | 2020-07-29 | 2021-03-01 | Федеральное государственное бюджетное учреждение науки Институт химии Дальневосточного отделения Российской академии наук (ИХ ДВО РАН) | Способ получения биополимерного гидрогеля |
| CN114230678B (zh) * | 2021-12-13 | 2023-09-01 | 珠海通桥医疗科技有限公司 | 一种用于血管内治疗的光交联水凝胶栓塞系统及使用方法 |
| CN114507359A (zh) * | 2022-02-17 | 2022-05-17 | 浙江大学 | 木质素磺酸盐的改性材料制备法及其在纳米农药中的应用 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5257102A (en) * | 1975-11-06 | 1977-05-11 | Sumitomo Chemical Co | Process for preparing carboxylic acid amide |
| US4716224A (en) * | 1984-05-04 | 1987-12-29 | Seikagaku Kogyo Co. Ltd. | Crosslinked hyaluronic acid and its use |
| SE442820B (sv) * | 1984-06-08 | 1986-02-03 | Pharmacia Ab | Gel av tverbunden hyaluronsyra for anvendning som glaskroppssubstitut |
| US4636524A (en) * | 1984-12-06 | 1987-01-13 | Biomatrix, Inc. | Cross-linked gels of hyaluronic acid and products containing such gels |
| US4582865A (en) * | 1984-12-06 | 1986-04-15 | Biomatrix, Inc. | Cross-linked gels of hyaluronic acid and products containing such gels |
| US4605691A (en) * | 1984-12-06 | 1986-08-12 | Biomatrix, Inc. | Cross-linked gels of hyaluronic acid and products containing such gels |
| SE8501022L (sv) * | 1985-03-01 | 1986-09-02 | Pharmacia Ab | Format alster och forfarande for dess framstellning |
| US4713448A (en) * | 1985-03-12 | 1987-12-15 | Biomatrix, Inc. | Chemically modified hyaluronic acid preparation and method of recovery thereof from animal tissues |
| IT1184161B (it) * | 1985-03-14 | 1987-10-22 | Franco Conti | Derivati del chitosano costituiti da complessi di coordinazione con ioni ferrosi |
| 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 |
| SK278783B6 (sk) * | 1989-12-18 | 1998-02-04 | Chemický Ústav Sav | Spôsob naviazania biologicky aktívnych látok obsah |
| DE527942T1 (de) * | 1990-05-04 | 1994-03-03 | Perio Prod Ltd | System zur arzneistoffabgabe im colon. |
| ES2149178T3 (es) * | 1991-08-16 | 2000-11-01 | Miles A Galin | Implante ocular para la camara anterior refractivo, recubierto con un medicamento. |
| JP2855307B2 (ja) * | 1992-02-05 | 1999-02-10 | 生化学工業株式会社 | 光反応性グリコサミノグリカン、架橋グリコサミノグリカン及びそれらの製造方法 |
| CA2076732C (en) * | 1992-04-17 | 2006-05-09 | Kimberly-Clark Worldwide, Inc. | Modified polysaccharides having improved absorbent properties and process for the preparation thereof |
| US5550189A (en) * | 1992-04-17 | 1996-08-27 | Kimberly-Clark Corporation | Modified polysaccharides having improved absorbent properties and process for the preparation thereof |
| US5616568A (en) * | 1993-11-30 | 1997-04-01 | The Research Foundation Of State University Of New York | Functionalized derivatives of hyaluronic acid |
| JP3107726B2 (ja) * | 1994-05-13 | 2000-11-13 | 株式会社クラレ | 水膨潤性高分子ゲル |
| US5690961A (en) * | 1994-12-22 | 1997-11-25 | Hercules Incorporated | Acidic polysaccharides crosslinked with polycarboxylic acids and their uses |
| JP4018181B2 (ja) * | 1995-11-07 | 2007-12-05 | 生化学工業株式会社 | グリコサミノグリカン誘導体およびその製造法 |
| JPH09176204A (ja) * | 1995-12-28 | 1997-07-08 | Kazukiyo Kobayashi | シアロ糖鎖含有機能性物質及びその合成方法 |
| JPH09278803A (ja) * | 1996-04-09 | 1997-10-28 | Kuraray Co Ltd | 医療用手当材 |
| JP3413062B2 (ja) * | 1996-06-19 | 2003-06-03 | キヤノン株式会社 | 糖鎖高分子化合物を含む高分子化合物及びその分解方法 |
| FR2752843B1 (fr) * | 1996-08-30 | 1998-10-16 | Sod Conseils Rech Applic | Copolymeres reticules a base de polymeres polycarboxyliques et leur utilisation comme support de composition pharmaceutique |
| US6642363B1 (en) * | 1996-09-19 | 2003-11-04 | The Regents Of The University Of Michigan | Polymers containing polysaccharides such as alginates or modified alginates |
| US6630457B1 (en) * | 1998-09-18 | 2003-10-07 | Orthogene Llc | Functionalized derivatives of hyaluronic acid, formation of hydrogels in situ using same, and methods for making and using same |
| IT1303738B1 (it) | 1998-11-11 | 2001-02-23 | Aquisitio S P A | Processo di reticolazione di polisaccaridi carbossilati. |
| IT1303735B1 (it) * | 1998-11-11 | 2001-02-23 | Falorni Italia Farmaceutici S | Acidi ialuronici reticolati e loro usi medici. |
-
1998
- 1998-11-11 IT IT1998MI002443A patent/IT1303738B1/it active
-
1999
- 1999-11-09 PT PT99971819T patent/PT1137670E/pt unknown
- 1999-11-09 IL IL14306499A patent/IL143064A0/xx not_active IP Right Cessation
- 1999-11-09 HU HU0104075A patent/HU227731B1/hu not_active IP Right Cessation
- 1999-11-09 CZ CZ20011651A patent/CZ303485B6/cs not_active IP Right Cessation
- 1999-11-09 AU AU13803/00A patent/AU756158B2/en not_active Ceased
- 1999-11-09 CN CNB99813144XA patent/CN1144818C/zh not_active Expired - Fee Related
- 1999-11-09 TR TR2001/01325T patent/TR200101325T2/xx unknown
- 1999-11-09 EP EP99971819A patent/EP1137670B1/en not_active Revoked
- 1999-11-09 BR BR9915238-0A patent/BR9915238A/pt not_active Application Discontinuation
- 1999-11-09 DK DK99971819T patent/DK1137670T3/da active
- 1999-11-09 AT AT99971819T patent/ATE291590T1/de active
- 1999-11-09 CA CA002350665A patent/CA2350665A1/en not_active Abandoned
- 1999-11-09 RU RU2001112487/04A patent/RU2230073C2/ru not_active IP Right Cessation
- 1999-11-09 SI SI9930767T patent/SI1137670T1/xx unknown
- 1999-11-09 ES ES99971819T patent/ES2237971T3/es not_active Expired - Lifetime
- 1999-11-09 US US09/830,744 patent/US6734298B1/en not_active Expired - Lifetime
- 1999-11-09 WO PCT/EP1999/008480 patent/WO2000027886A1/en active IP Right Grant
- 1999-11-09 KR KR1020017005930A patent/KR100685454B1/ko not_active IP Right Cessation
- 1999-11-09 JP JP2000581063A patent/JP2002529549A/ja active Pending
- 1999-11-09 DE DE69924407T patent/DE69924407T2/de not_active Expired - Lifetime
- 1999-11-09 NZ NZ511308A patent/NZ511308A/xx not_active IP Right Cessation
-
2001
- 2001-05-10 ZA ZA200103800A patent/ZA200103800B/en unknown
- 2001-05-10 NO NO20012316A patent/NO20012316L/no not_active Application Discontinuation
-
2002
- 2002-04-11 HK HK02102741.6A patent/HK1041010B/zh not_active IP Right Cessation
-
2004
- 2004-02-26 US US10/787,736 patent/US20040167098A1/en not_active Abandoned
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