DD297165A5 - Neue sulfatierte polysaccharide, physiologisch vertraegliche salze davon und verfahren zu ihrer herstellung - Google Patents
Neue sulfatierte polysaccharide, physiologisch vertraegliche salze davon und verfahren zu ihrer herstellung Download PDFInfo
- Publication number
- DD297165A5 DD297165A5 DD90343252A DD34325290A DD297165A5 DD 297165 A5 DD297165 A5 DD 297165A5 DD 90343252 A DD90343252 A DD 90343252A DD 34325290 A DD34325290 A DD 34325290A DD 297165 A5 DD297165 A5 DD 297165A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- reaction
- fgag
- sulfated polysaccharides
- physiologically acceptable
- sodium
- Prior art date
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 34
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 26
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 67
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003814 drug Substances 0.000 claims abstract description 17
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims abstract description 15
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims abstract description 15
- 229940079593 drug Drugs 0.000 claims abstract description 15
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 13
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims abstract description 10
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims abstract description 8
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940097043 glucuronic acid Drugs 0.000 claims abstract description 8
- 239000000843 powder Substances 0.000 claims abstract description 7
- 241000251511 Holothuroidea Species 0.000 claims abstract description 6
- 238000004458 analytical method Methods 0.000 claims abstract description 6
- 230000015271 coagulation Effects 0.000 claims abstract description 6
- 238000005345 coagulation Methods 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 35
- 230000000694 effects Effects 0.000 claims description 33
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 13
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 12
- 108090000190 Thrombin Proteins 0.000 claims description 12
- 229960002897 heparin Drugs 0.000 claims description 12
- 229920000669 heparin Polymers 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229960004072 thrombin Drugs 0.000 claims description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 10
- 238000002955 isolation Methods 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 235000011056 potassium acetate Nutrition 0.000 claims description 5
- 230000002429 anti-coagulating effect Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- FNEHAOQZWPHONV-UHFFFAOYSA-N 9h-carbazole;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C3=CC=CC=C3NC2=C1 FNEHAOQZWPHONV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000004019 antithrombin Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 230000001858 anti-Xa Effects 0.000 claims description 2
- 239000003146 anticoagulant agent Substances 0.000 claims description 2
- 229940127219 anticoagulant drug Drugs 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims 8
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000002523 gelfiltration Methods 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- 238000005342 ion exchange Methods 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 7
- 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 abstract description 3
- ZRKHIAJIHKHTDY-UHFFFAOYSA-N 5-methylbenzene-1,3-diol;hydrochloride Chemical compound Cl.CC1=CC(O)=CC(O)=C1 ZRKHIAJIHKHTDY-UHFFFAOYSA-N 0.000 abstract 1
- PGWTYMLATMNCCZ-UHFFFAOYSA-M azure A Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 PGWTYMLATMNCCZ-UHFFFAOYSA-M 0.000 abstract 1
- 239000011734 sodium Chemical class 0.000 description 41
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 40
- 229910052708 sodium Inorganic materials 0.000 description 40
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 39
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 159000000000 sodium salts Chemical class 0.000 description 20
- 238000005119 centrifugation Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 210000002381 plasma Anatomy 0.000 description 8
- 239000000829 suppository Substances 0.000 description 8
- 239000011777 magnesium Chemical class 0.000 description 7
- OHJKXVLJWUPWQG-PNRHKHKDSA-N Heparinsodiumsalt Chemical compound O[C@@H]1[C@@H](NS(O)(=O)=O)[C@@H](O)O[C@H](COS(O)(=O)=O)[C@H]1O[C@H]1[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O)[C@H](C(O)=O)O1 OHJKXVLJWUPWQG-PNRHKHKDSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 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 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- 108010000499 Thromboplastin Proteins 0.000 description 3
- 102000002262 Thromboplastin Human genes 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000014508 negative regulation of coagulation Effects 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- 108090000935 Antithrombin III Proteins 0.000 description 2
- 241000965254 Apostichopus japonicus Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010054218 Factor VIII Proteins 0.000 description 2
- 102000001690 Factor VIII Human genes 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000258195 Holothuria Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 108010019160 Pancreatin Proteins 0.000 description 2
- 102000004211 Platelet factor 4 Human genes 0.000 description 2
- 108090000778 Platelet factor 4 Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000529895 Stercorarius Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000012691 depolymerization reaction Methods 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229960000301 factor viii Drugs 0.000 description 2
- 238000001641 gel filtration chromatography Methods 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- -1 iron ions Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229940055695 pancreatin Drugs 0.000 description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- KCYCGNHQFGTGSS-UWVGGRQHSA-N (2S,5S)-5-amino-4-oxo-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-carboxylic acid Chemical compound O=C1[C@@H](N)CCC2=CC=CC3=C2N1[C@H](C(O)=O)C3 KCYCGNHQFGTGSS-UWVGGRQHSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001213448 Actinopyga Species 0.000 description 1
- 241001188173 Actinopyga echinites Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-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
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 102000004411 Antithrombin III Human genes 0.000 description 1
- 102100022977 Antithrombin-III Human genes 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241001137883 Cucumaria Species 0.000 description 1
- 241000122213 Cucumaria echinata Species 0.000 description 1
- 241001505481 Cucumaria frondosa Species 0.000 description 1
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000156978 Erebia Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 108010014173 Factor X Proteins 0.000 description 1
- 108010074860 Factor Xa Proteins 0.000 description 1
- 241000941624 Holothuria atra Species 0.000 description 1
- 241001213463 Holothuria edulis Species 0.000 description 1
- 241001213462 Holothuria leucospilota Species 0.000 description 1
- 241000451664 Holothuria pervicax Species 0.000 description 1
- 241000133638 Holothuria scabra Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000251512 Leptosynapta inhaerens Species 0.000 description 1
- 241001674233 Molpadia musculus Species 0.000 description 1
- 241000251508 Paracaudina chilensis Species 0.000 description 1
- 241001295374 Parastichopus nigripunctatus Species 0.000 description 1
- 241000915706 Pentacta Species 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000258161 Stichopus Species 0.000 description 1
- 241000887536 Stichopus horrens Species 0.000 description 1
- 241000980131 Synapta maculata Species 0.000 description 1
- 241000941622 Thelenota Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 229960005348 antithrombin iii Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- 229940112016 barium acetate Drugs 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000440 effect on coagulation Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical class CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000009024 positive feedback mechanism Effects 0.000 description 1
- 229960004109 potassium acetate Drugs 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
-
- 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
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD90343252A DD297165A5 (de) | 1989-02-06 | 1990-08-06 | Neue sulfatierte polysaccharide, physiologisch vertraegliche salze davon und verfahren zu ihrer herstellung |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2829989 | 1989-02-06 | ||
| DD90343252A DD297165A5 (de) | 1989-02-06 | 1990-08-06 | Neue sulfatierte polysaccharide, physiologisch vertraegliche salze davon und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD297165A5 true DD297165A5 (de) | 1992-01-02 |
Family
ID=12244736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90343252A DD297165A5 (de) | 1989-02-06 | 1990-08-06 | Neue sulfatierte polysaccharide, physiologisch vertraegliche salze davon und verfahren zu ihrer herstellung |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0408770B1 (fr) |
| JP (1) | JP2714718B2 (fr) |
| KR (1) | KR970000528B1 (fr) |
| AT (1) | ATE138938T1 (fr) |
| AU (1) | AU634521B2 (fr) |
| CA (1) | CA2026992C (fr) |
| DD (1) | DD297165A5 (fr) |
| DE (1) | DE69027256T2 (fr) |
| DK (1) | DK0408770T3 (fr) |
| ES (1) | ES2087907T3 (fr) |
| HU (1) | HU211988A9 (fr) |
| WO (1) | WO1990008784A1 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0491027A (ja) * | 1990-08-02 | 1992-03-24 | Taiho Yakuhin Kogyo Kk | 抗ヒト免疫不全症ウィルス剤 |
| AU644464B2 (en) * | 1990-08-02 | 1993-12-09 | Taiho Pharmaceutical Co., Ltd. | Anti-human immunodeficiency virus agent |
| US6255296B1 (en) * | 1994-01-11 | 2001-07-03 | Endomatrix, Inc. | Composition and method for treating a patient susceptible to or suffering from a cardiovascular disorder or disease |
| KR100240544B1 (ko) * | 1995-12-20 | 2000-01-15 | 고바야시 유끼오 | 혈관 내막 비후 억제제 |
| US5876762A (en) * | 1996-08-05 | 1999-03-02 | Coastside Bio Resources | Process for obtaining medically active fractions from sea cucumbers |
| US6399105B1 (en) | 1999-01-20 | 2002-06-04 | Peter Donald Collin | Sea cucumber carotenoid lipid fraction products and methods of use |
| FR2797768B1 (fr) | 1999-09-01 | 2003-06-13 | Ifremer | Utilisation d'un polysaccharide sulfate de bas poids moleculaire pour l'obtention d'un medicament actif contre la thrombose vasculaire |
| EP2980103B1 (fr) | 2013-03-26 | 2020-11-04 | Jiuzhitang Co., Ltd. | Dérivé de glycosaminoglycane de faible poids moléculaire, composition pharmaceutique de celui-ci, procédé de préparation de celui-ci et utilisation de celui-ci |
| CN103788222B (zh) | 2014-01-08 | 2016-08-31 | 中国科学院昆明植物研究所 | Fuc3S4S取代的低聚糖胺聚糖及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3118588C2 (de) * | 1981-05-11 | 1983-07-07 | Luitpold-Werk, Chemisch-Pharmazeutische Fabrik, 8000 München | Verfahren zur Herstellung eines injizierbaren hochreinen Chondroitinpolysulfates, hiernach erhältliches Produkt und pharmazeutische Zusammensetzung |
| JPS63128001A (ja) * | 1986-11-19 | 1988-05-31 | Taiho Yakuhin Kogyo Kk | Fgag及びその塩、その製造方法並びにそれを含有する播種性血管内凝固症候群治療剤 |
| JP2785611B2 (ja) * | 1992-10-13 | 1998-08-13 | 宇部興産株式会社 | 被処理鋼板材コイルの先端口出し装置 |
-
1990
- 1990-02-06 DE DE69027256T patent/DE69027256T2/de not_active Expired - Fee Related
- 1990-02-06 DK DK90902694.0T patent/DK0408770T3/da active
- 1990-02-06 JP JP2502725A patent/JP2714718B2/ja not_active Expired - Fee Related
- 1990-02-06 CA CA002026992A patent/CA2026992C/fr not_active Expired - Fee Related
- 1990-02-06 WO PCT/JP1990/000141 patent/WO1990008784A1/fr not_active Ceased
- 1990-02-06 AU AU50325/90A patent/AU634521B2/en not_active Ceased
- 1990-02-06 AT AT90902694T patent/ATE138938T1/de not_active IP Right Cessation
- 1990-02-06 EP EP90902694A patent/EP0408770B1/fr not_active Expired - Lifetime
- 1990-02-06 ES ES90902694T patent/ES2087907T3/es not_active Expired - Lifetime
- 1990-08-06 DD DD90343252A patent/DD297165A5/de unknown
- 1990-10-06 KR KR1019900702212A patent/KR970000528B1/ko not_active Expired - Fee Related
-
1995
- 1995-06-30 HU HU95P/P00729P patent/HU211988A9/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2714718B2 (ja) | 1998-02-16 |
| KR970000528B1 (ko) | 1997-01-13 |
| EP0408770A1 (fr) | 1991-01-23 |
| WO1990008784A1 (fr) | 1990-08-09 |
| ATE138938T1 (de) | 1996-06-15 |
| KR910700269A (ko) | 1991-03-14 |
| DE69027256T2 (de) | 1996-12-19 |
| DE69027256D1 (de) | 1996-07-11 |
| EP0408770A4 (en) | 1992-03-18 |
| CA2026992C (fr) | 1998-11-10 |
| CA2026992A1 (fr) | 1990-08-07 |
| AU634521B2 (en) | 1993-02-25 |
| AU5032590A (en) | 1990-08-24 |
| EP0408770B1 (fr) | 1996-06-05 |
| HU211988A9 (en) | 1996-01-29 |
| DK0408770T3 (da) | 1996-10-07 |
| ES2087907T3 (es) | 1996-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3102621C2 (fr) | ||
| DE69023957T2 (de) | Sulfatierte Polysaccharide, Antikoagulierungs- und Antikomplementärmittel, hergestellt aus Fukanen aus braunen Algen, und Verfahren zu deren Herstellung. | |
| DE68917040T2 (de) | Heparinderivate und Verfahren zu deren Herstellung. | |
| DE3851973T2 (de) | Heparine mit niedrigem Molekulargewicht und regelmässiger Struktur, ihre Herstellung und biologische Verwendungen. | |
| DE69012154T2 (de) | Heparinderivate und Verfahren zu ihrer Herstellung. | |
| AT398976B (de) | Gemische von polysacchariden mit niedrigem molekulargewicht, deren herstellungsverfahren und verwendung | |
| DE2833898C2 (fr) | ||
| DE69228362T2 (de) | Hochmolekulare, N,O-sulfatierte Heparosane; Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE68921633T2 (de) | Oligosaccharide mit antiatherosclerotischer wirkung. | |
| DE69016383T2 (de) | Supersulfatierte Heparine. | |
| DD251355A5 (de) | Verfahren zur herstellung von oligosacchariden | |
| JPS59133202A (ja) | 解重合及び超硫酸化ヘパリン、その製造方法並びに製薬組成物 | |
| DE69722434T2 (de) | Buttersäure-ester mit antiproliferativer wirkung und diese enthaltende pharmazeutische zusammensetzungen | |
| DE69708862T2 (de) | Derivate von k5 polysaccharid mit hoher, blutgerinnungshemmender wirkung | |
| DE3689493T2 (de) | Verfahren zur Herstellung von reinem natürlichen Heparansulfat und Dermatansulfat und ihre pharmazeutische Verwendung. | |
| EP0504645B1 (fr) | Utilisation d'oligosaccharides sulphatés pour le traitement des maladies artériosclérotiques et pour la prévention de la resténose | |
| US5519010A (en) | Sulfated polysaccharide, pharmaceutically acceptable salt thereof, process for preparing same and medicament containing same as effective component | |
| DE69806468T2 (de) | Glykosaminoglykane mit hoher antithrombotischer wirkung | |
| DE68916878T2 (de) | Selektiv O-acylierte Glycosaminoglykane. | |
| DE69814140T2 (de) | Kohlenhydrat-derivate | |
| DE2751570A1 (de) | Carboxymethylierte beta-1,3-glucane, verfahren zu deren herstellung und antitumormittel | |
| DE68904264T2 (de) | Fragmente und fraktionen von heparin mit wirkung gegen hiv. | |
| DE69223153T2 (de) | Dermatansulfat mit trombolytischer wirkung und arzneiformen welche dieses enthalten | |
| DE60208528T2 (de) | Hochsulfatierte derivate von k5-polysacchariden und ihre herstellung | |
| DE3787996T2 (de) | Heparine, frei von E.D.T.A., Fraktionen und Fragmente von Heparin, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, welche diese enthalten. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RPI | Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act) | ||
| RPV | Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act) | ||
| RPI | Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act) | ||
| RPV | Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act) | ||
| ASS | Change of applicant or owner |
Owner name: KOTAI KASEI CO., LTD., OAZA MOTOHARA, SAITAMA Effective date: 19960116 Owner name: TAIHO PHARMACEUTICAL CO., LTD., TOKYO Effective date: 19960116 |
|
| IF04 | In force in the year 2004 |
Expiry date: 20100807 |