DE60219653T2 - Pharmazeutische zusammensetzung mit chito-oligomeren - Google Patents
Pharmazeutische zusammensetzung mit chito-oligomeren Download PDFInfo
- Publication number
- DE60219653T2 DE60219653T2 DE60219653T DE60219653T DE60219653T2 DE 60219653 T2 DE60219653 T2 DE 60219653T2 DE 60219653 T DE60219653 T DE 60219653T DE 60219653 T DE60219653 T DE 60219653T DE 60219653 T2 DE60219653 T2 DE 60219653T2
- Authority
- DE
- Germany
- Prior art keywords
- oligomers
- chito
- treatment
- chitin
- chain length
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims abstract description 38
- 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 claims abstract description 37
- 229920002101 Chitin Polymers 0.000 claims abstract description 35
- 229950006780 n-acetylglucosamine Drugs 0.000 claims abstract description 30
- 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 claims abstract description 29
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229960002442 glucosamine Drugs 0.000 claims abstract description 20
- 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 claims abstract description 19
- 230000006196 deacetylation Effects 0.000 claims abstract description 19
- 238000003381 deacetylation reaction Methods 0.000 claims abstract description 19
- 208000012659 Joint disease Diseases 0.000 claims abstract description 17
- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 16
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 230000004054 inflammatory process Effects 0.000 claims description 11
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 208000024891 symptom Diseases 0.000 claims description 8
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000000552 rheumatic effect Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 24
- 238000000034 method Methods 0.000 abstract description 6
- 230000002757 inflammatory effect Effects 0.000 abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 229920001661 Chitosan Polymers 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- 229920002674 hyaluronan Polymers 0.000 description 11
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[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@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-MNSSHETKSA-N 0.000 description 11
- 229940099552 hyaluronan Drugs 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 10
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 10
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 108010022172 Chitinases Proteins 0.000 description 8
- 102000012286 Chitinases Human genes 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 101000883515 Homo sapiens Chitinase-3-like protein 1 Proteins 0.000 description 7
- 206010003246 arthritis Diseases 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 102100038196 Chitinase-3-like protein 1 Human genes 0.000 description 6
- 101710128038 Hyaluronan synthase Proteins 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229920001542 oligosaccharide Polymers 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 210000001612 chondrocyte Anatomy 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- XHMJOUIAFHJHBW-VFUOTHLCSA-N glucosamine 6-phosphate Chemical compound N[C@H]1[C@H](O)O[C@H](COP(O)(O)=O)[C@H](O)[C@@H]1O XHMJOUIAFHJHBW-VFUOTHLCSA-N 0.000 description 5
- 210000001503 joint Anatomy 0.000 description 5
- 210000002540 macrophage Anatomy 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000000968 intestinal effect Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000029663 wound healing Effects 0.000 description 4
- 102000016611 Proteoglycans Human genes 0.000 description 3
- 108010067787 Proteoglycans Proteins 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000007071 enzymatic hydrolysis Effects 0.000 description 3
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 150000002337 glycosamines Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 201000003068 rheumatic fever Diseases 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 102100037839 Acidic mammalian chitinase Human genes 0.000 description 2
- 101710178876 Acidic mammalian chitinase Proteins 0.000 description 2
- GSXOAOHZAIYLCY-UHFFFAOYSA-N D-F6P Natural products OCC(=O)C(O)C(O)C(O)COP(O)(O)=O GSXOAOHZAIYLCY-UHFFFAOYSA-N 0.000 description 2
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229920002683 Glycosaminoglycan Polymers 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- BGWGXPAPYGQALX-ARQDHWQXSA-N beta-D-fructofuranose 6-phosphate Chemical compound OC[C@@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O BGWGXPAPYGQALX-ARQDHWQXSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 210000000845 cartilage Anatomy 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229940097043 glucuronic acid Drugs 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 210000001179 synovial fluid Anatomy 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- XLEYFDVVXLMULC-UHFFFAOYSA-N 2',4',6'-trihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=C(O)C=C1O XLEYFDVVXLMULC-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 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
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000005469 Chitin Synthase Human genes 0.000 description 1
- 108700040089 Chitin synthases Proteins 0.000 description 1
- 101710203678 Chitinase-like protein Proteins 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000252212 Danio rerio Species 0.000 description 1
- 101100377506 Drosophila melanogaster 14-3-3zeta gene Proteins 0.000 description 1
- -1 Flakes Substances 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 102000003918 Hyaluronan Synthases Human genes 0.000 description 1
- 108090000320 Hyaluronan Synthases Proteins 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 206010023232 Joint swelling Diseases 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-OZRXBMAMSA-N N-acetyl-beta-D-mannosamine Chemical compound CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-OZRXBMAMSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 208000008558 Osteophyte Diseases 0.000 description 1
- DPTYILOGADPXRZ-RXDSZOQSSA-N Penta-N-acetylchitopentaose Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 DPTYILOGADPXRZ-RXDSZOQSSA-N 0.000 description 1
- HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 description 1
- HDYANYHVCAPMJV-UHFFFAOYSA-N Uridine diphospho-D-glucuronic acid Natural products O1C(N2C(NC(=O)C=C2)=O)C(O)C(O)C1COP(O)(=O)OP(O)(=O)OC1OC(C(O)=O)C(O)C(O)C1O HDYANYHVCAPMJV-UHFFFAOYSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 241000269370 Xenopus <genus> Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940100228 acetyl coenzyme a Drugs 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 230000019552 anatomical structure morphogenesis Effects 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WMWKTCPGFOEPBD-YGIWDPDDSA-N azane;(2s,3s,4s,5r,6r)-6-[[[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound N.C([C@@H]1[C@H]([C@H]([C@@H](O1)N1C(NC(=O)C=C1)=O)O)O)OP(O)(=O)OP(O)(=O)O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O WMWKTCPGFOEPBD-YGIWDPDDSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008414 cartilage metabolism Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 108010040093 cellulose synthase Proteins 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical group O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 150000002016 disaccharides Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 210000001647 gastrula Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000008273 hexosamines Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 102000054350 human CHI3L1 Human genes 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 230000008407 joint function Effects 0.000 description 1
- 208000018937 joint inflammation Diseases 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000005033 mesothelial cell Anatomy 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- FUHDMRPNDKDRFE-LPUYKFNUSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r)-5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy- Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)NC(C)=O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 FUHDMRPNDKDRFE-LPUYKFNUSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000003349 osteoarthritic effect Effects 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 210000001258 synovial membrane Anatomy 0.000 description 1
- 210000002437 synoviocyte Anatomy 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 230000008189 vertebrate development Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Polymers & Plastics (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Materials Engineering (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IS6085A IS6085A (is) | 2001-09-26 | 2001-09-26 | Lyfjablanda með kítósan óligómerum |
| IS608501 | 2001-09-26 | ||
| PCT/IS2002/000016 WO2003026677A1 (en) | 2001-09-26 | 2002-09-26 | Pharmaceutical composition comprising chito-oligomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60219653D1 DE60219653D1 (de) | 2007-05-31 |
| DE60219653T2 true DE60219653T2 (de) | 2008-01-03 |
Family
ID=36700489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60219653T Expired - Lifetime DE60219653T2 (de) | 2001-09-26 | 2002-09-26 | Pharmazeutische zusammensetzung mit chito-oligomeren |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7985741B2 (https=) |
| EP (1) | EP1435976B1 (https=) |
| JP (1) | JP4613008B2 (https=) |
| KR (1) | KR20040062548A (https=) |
| AT (1) | ATE359797T1 (https=) |
| CA (1) | CA2507926C (https=) |
| DE (1) | DE60219653T2 (https=) |
| DK (1) | DK1435976T3 (https=) |
| ES (1) | ES2284935T3 (https=) |
| IS (2) | IS6085A (https=) |
| PT (1) | PT1435976E (https=) |
| SI (1) | SI1435976T1 (https=) |
| WO (1) | WO2003026677A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003054208A2 (en) * | 2001-12-13 | 2003-07-03 | Ism Biopolymer Inc. | Method of modulating release of saccharides and uses thereof |
| GB0321996D0 (en) * | 2003-09-19 | 2003-10-22 | Novartis Nutrition Ag | Organic compounds |
| EP1670486A4 (en) * | 2003-10-01 | 2009-04-01 | Optimer Pharmaceuticals Inc | TREATMENT OF A CONDITION IN A MAMMALIAN WITH ADMINISTRATION OF AMINO SUGAR AND USES THEREOF |
| US20070082851A1 (en) * | 2003-11-24 | 2007-04-12 | Optimer Pharmaceuticals Inc. | Treatment of a condition in a mammal with administration of Compounds and Methods of Use |
| WO2005112948A1 (ja) * | 2004-05-21 | 2005-12-01 | Tottori University | 創傷の治療又は処置のための薬剤 |
| AU2006257177A1 (en) * | 2005-06-14 | 2006-12-21 | Genis Ehf. | Compositions of partially deacetylated chitin derivatives |
| WO2007001282A2 (en) * | 2005-06-16 | 2007-01-04 | E.I. Dupont De Nemours And Company | Low molecular weight polyglucosamines and polygalactosamines |
| US7485718B2 (en) | 2005-06-16 | 2009-02-03 | E. I. Du Pont De Nemours And Company | Chemical synthesis of low molecular weight polyglucosamines and polygalactosamines |
| KR100831335B1 (ko) * | 2006-06-22 | 2008-05-22 | 부경대학교 산학협력단 | 인간 피부 섬유아세포에서 메트릭스메탈로프로테이나제-2의 발현 및 활성을 억제시키는키토올리고사카라이드 화합물 및 이를 함유한 메트릭스메탈로프로테이나제-2 억제제 |
| EP2318014B1 (en) * | 2008-07-18 | 2016-09-14 | Genís hf. | New composition for treating autoimmune disorders |
| KR20100060634A (ko) * | 2008-11-28 | 2010-06-07 | (주)아모레퍼시픽 | 미토콘드리아 활성화를 위한 조성물 |
| KR101729137B1 (ko) * | 2009-07-28 | 2017-04-26 | (주)아모레퍼시픽 | 키토올리고당을 함유하는 피로회복용 조성물 |
| JP6141265B2 (ja) | 2011-06-03 | 2017-06-07 | マグワイア アビー， エルエルシー | 関節の潤滑性を改善するための方法、組成物及び物品 |
| AR090026A1 (es) | 2011-09-08 | 2014-10-15 | Novozymes Bioag As | Metodos y composiciones para tratamiento de semillas |
| ES2970761T3 (es) | 2011-09-14 | 2024-05-30 | Novozymes Bioag As | Uso de lipoquitooligosacáridos y/o quitooligosacáridos en combinación con microorganismos solubilizadores de fosfato para potenciar el crecimiento de las plantas |
| RU2564844C1 (ru) | 2011-09-23 | 2015-10-10 | Новозимс Биоаг А/С | Хитоолигосахариды и способы их применения для усиления роста растений |
| AU2012312006B2 (en) * | 2011-09-23 | 2015-10-29 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing corn growth |
| JP6232048B2 (ja) | 2012-04-23 | 2017-11-15 | ジェニス エイチエフ． | 骨移植片代用材としての部分的に脱アセチル化されたキチンを含む自硬性の生体活性セメント組成物 |
| JP6285497B2 (ja) * | 2016-06-07 | 2018-02-28 | 株式会社エバーライフ | 鶏冠抽出物含有経口組成物及び鶏冠抽出物の香味に由来する摂取困難性の改善方法 |
| KR101673368B1 (ko) | 2016-07-14 | 2016-11-08 | 김기혁 | 공정가스 반응물의 콜드트랩 장치 |
| CA3256512A1 (en) * | 2022-04-21 | 2023-10-26 | Therapeutikos, Inc. | METHODS OF TREATING INFLAMMATION |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5919122B2 (ja) * | 1976-10-12 | 1984-05-02 | 味の素株式会社 | 水溶性部分脱アセチル化キチン及びその製造法 |
| US4532134A (en) * | 1981-04-06 | 1985-07-30 | Malette William Graham | Method of achieving hemostasis, inhibiting fibroplasia, and promoting tissue regeneration in a tissue wound |
| JP2527317B2 (ja) * | 1986-12-19 | 1996-08-21 | ライオン株式会社 | 骨疾患治療剤 |
| US6184037B1 (en) * | 1996-05-17 | 2001-02-06 | Genemedicine, Inc. | Chitosan related compositions and methods for delivery of nucleic acids and oligonucleotides into a cell |
| CA2274510C (en) * | 1996-12-13 | 2010-02-16 | Lescarden, Inc. | Treatment of osteoarthritis by administering poly-n-acetyl-d-glucosamine |
| JP3062592B2 (ja) * | 1997-05-30 | 2000-07-10 | 農林水産省食品総合研究所長 | ２−アセチルアミノ−４−Ｏ−（２−アミノ−２−デオキシ−β−Ｄ −グルコピラノシル）−２−デオキシ−Ｄ −グルコースおよびその塩の製造法 |
| US6492350B2 (en) * | 2000-01-27 | 2002-12-10 | Jdc (Hawaii) Inc. | Chitin oligosaccharides and/or chitosan oligosaccharides for preventing or treating common cold or treating pain |
| EP1127574A1 (en) * | 2000-02-22 | 2001-08-29 | Food Industry Research and Development Institute | Use of chitinous materials for inhibiting cellular nitric oxide production |
| CA2313836C (en) * | 2000-03-15 | 2009-06-09 | Cargill, Incorporated | Chitosan and method of preparing chitosan |
| US20020119949A1 (en) * | 2001-02-26 | 2002-08-29 | Asa Hellman | Prophylactic teat treatment |
| AU2006257177A1 (en) * | 2005-06-14 | 2006-12-21 | Genis Ehf. | Compositions of partially deacetylated chitin derivatives |
-
2001
- 2001-09-26 IS IS6085A patent/IS6085A/is unknown
-
2002
- 2002-09-26 EP EP02777769A patent/EP1435976B1/en not_active Expired - Lifetime
- 2002-09-26 US US10/490,637 patent/US7985741B2/en active Active
- 2002-09-26 DK DK02777769T patent/DK1435976T3/da active
- 2002-09-26 KR KR10-2004-7004323A patent/KR20040062548A/ko not_active Ceased
- 2002-09-26 JP JP2003530312A patent/JP4613008B2/ja not_active Expired - Lifetime
- 2002-09-26 AT AT02777769T patent/ATE359797T1/de active
- 2002-09-26 PT PT02777769T patent/PT1435976E/pt unknown
- 2002-09-26 DE DE60219653T patent/DE60219653T2/de not_active Expired - Lifetime
- 2002-09-26 WO PCT/IS2002/000016 patent/WO2003026677A1/en not_active Ceased
- 2002-09-26 SI SI200230558T patent/SI1435976T1/sl unknown
- 2002-09-26 CA CA2507926A patent/CA2507926C/en not_active Expired - Lifetime
- 2002-09-26 ES ES02777769T patent/ES2284935T3/es not_active Expired - Lifetime
-
2004
- 2004-03-22 IS IS7193A patent/IS2783B/is unknown
-
2011
- 2011-06-20 US US13/164,397 patent/US8415326B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IS2783B (is) | 2012-05-15 |
| US7985741B2 (en) | 2011-07-26 |
| DK1435976T3 (da) | 2007-08-27 |
| EP1435976B1 (en) | 2007-04-18 |
| EP1435976A1 (en) | 2004-07-14 |
| JP2005507891A (ja) | 2005-03-24 |
| ATE359797T1 (de) | 2007-05-15 |
| US20050004073A1 (en) | 2005-01-06 |
| CA2507926A1 (en) | 2003-04-03 |
| KR20040062548A (ko) | 2004-07-07 |
| ES2284935T3 (es) | 2007-11-16 |
| WO2003026677A1 (en) | 2003-04-03 |
| US20110257381A1 (en) | 2011-10-20 |
| CA2507926C (en) | 2011-12-20 |
| SI1435976T1 (sl) | 2007-08-31 |
| JP4613008B2 (ja) | 2011-01-12 |
| IS7193A (is) | 2004-03-22 |
| IS6085A (is) | 2003-03-27 |
| US8415326B2 (en) | 2013-04-09 |
| DE60219653D1 (de) | 2007-05-31 |
| PT1435976E (pt) | 2007-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60219653T2 (de) | Pharmazeutische zusammensetzung mit chito-oligomeren | |
| DE60009574T2 (de) | Chondroitinsulfat aus lachsen | |
| Roberts | Structure of chitin and chitosan | |
| Xie et al. | Preparation, characterization and antioxidant activities of acetylated polysaccharides from Cyclocarya paliurus leaves | |
| DE68917009T2 (de) | Sulfaminoderivate von Chondroitinsulfat, Dermatansulfat und Hyaluronsäure und ihre pharmakologischen Eigenschaften. | |
| DE60025328T3 (de) | Verfahren zur herstellung von mehrfach vernetzten hyaluronsäurederivaten | |
| US6946551B2 (en) | Preparation of hyaluronic acid from eggshell membrane | |
| CN114133419B (zh) | 一种低分子量乙酰化透明质酸盐及其制备方法和应用 | |
| DE69228362T2 (de) | Hochmolekulare, N,O-sulfatierte Heparosane; Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| JP2005529191A (ja) | バイオマスからの細胞壁誘導体及びその調製法 | |
| WO2002042484A2 (de) | Verfahren zur herstellung von pektinhydrolyseprodukten | |
| DE69722434T2 (de) | Buttersäure-ester mit antiproliferativer wirkung und diese enthaltende pharmazeutische zusammensetzungen | |
| DE69535565T2 (de) | Verwendung von desulfatiertem Heparin | |
| DD285606A5 (de) | Verfahren zur herstellung von selektiv o-azylierten glucosaminoglycanen | |
| JP2587268B2 (ja) | 低粘度ヒアルロン酸又はその塩の製造方法 | |
| DE10221055A1 (de) | Verfahren zur hämokompatiblen Beschichtung von Oberflächen | |
| Ibram | Studies on chitosan, chitin and chitooligosaccharides and their biomedical properties | |
| US4098661A (en) | Method of producing neoschizophyllan having novel pharmacological activity | |
| DE69931038T2 (de) | Neue polysaccharidderivate, verfahren zu ihrer herstellung und medizinische zusammensetzungen die diese als aktives bestandteil enthalten | |
| CN1309667A (zh) | 半纤维素类原料的提取 | |
| WO1992013541A1 (de) | Die verwendung substituierter polysaccharide zur behandlung von degenerativen gelenkerkrankungen | |
| JP3955652B2 (ja) | 合成アミノ糖類誘導体及びその製造方法 | |
| CH633043A5 (en) | Process for preparing aminosugar derivatives | |
| DE4242813A1 (https=) | ||
| EP1473308A1 (de) | Stärkederivate zur klinischen, insbesondere parenteralen Anwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8381 | Inventor (new situation) |
Inventor name: EINARSSON, JON M., IS-101 REYKJAVIK, IS Inventor name: GISLASON, JOHANNES, IS-105 REYKJAVIK, IS Inventor name: PETER, MARTIN, 14476 GOLM, DE Inventor name: BAHRKE, SVEN, 14476 GOLM, DE |
|
| 8364 | No opposition during term of opposition |