NZ206697A - Depolymerised and supersulphated heparin and pharmaceutical compositions - Google Patents
Depolymerised and supersulphated heparin and pharmaceutical compositionsInfo
- Publication number
- NZ206697A NZ206697A NZ206697A NZ20669783A NZ206697A NZ 206697 A NZ206697 A NZ 206697A NZ 206697 A NZ206697 A NZ 206697A NZ 20669783 A NZ20669783 A NZ 20669783A NZ 206697 A NZ206697 A NZ 206697A
- Authority
- NZ
- New Zealand
- Prior art keywords
- heparin
- depolymerized
- supersulfated
- acid
- heparins
- Prior art date
Links
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class 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 title claims abstract description 82
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- 229920000669 heparin Polymers 0.000 claims abstract description 76
- 229960002897 heparin Drugs 0.000 claims abstract description 75
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 17
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract description 12
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000002785 anti-thrombosis Effects 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
- 230000003480 fibrinolytic effect Effects 0.000 claims abstract description 4
- 230000000055 hyoplipidemic effect Effects 0.000 claims abstract description 4
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 3
- 238000011282 treatment Methods 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- -1 alkali metal salt Chemical class 0.000 claims description 5
- 159000000007 calcium salts Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000003146 anticoagulant agent Substances 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 230000019635 sulfation Effects 0.000 abstract 1
- 238000005670 sulfation reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 16
- 230000000694 effects Effects 0.000 description 12
- 238000001962 electrophoresis Methods 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 11
- 230000001858 anti-Xa Effects 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 210000004347 intestinal mucosa Anatomy 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 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 5
- 229940127215 low-molecular weight heparin Drugs 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 108010013563 Lipoprotein Lipase Proteins 0.000 description 4
- 102000043296 Lipoprotein lipases Human genes 0.000 description 4
- 108090000190 Thrombin Proteins 0.000 description 4
- 230000023555 blood coagulation Effects 0.000 description 4
- 125000000600 disaccharide group Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000020764 fibrinolysis Effects 0.000 description 4
- 239000003055 low molecular weight heparin Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229960004072 thrombin Drugs 0.000 description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 3
- 108010074860 Factor Xa Proteins 0.000 description 3
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 3
- 230000009089 cytolysis Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 229960002442 glucosamine Drugs 0.000 description 3
- 159000000011 group IA salts Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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 compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 102000009123 Fibrin Human genes 0.000 description 2
- 108010073385 Fibrin Proteins 0.000 description 2
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 102000004895 Lipoproteins Human genes 0.000 description 2
- 108090001030 Lipoproteins Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 102000005686 Serum Globulins Human genes 0.000 description 2
- 108010045362 Serum Globulins Proteins 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000002429 anti-coagulating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 2
- 230000004071 biological effect 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
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 229950003499 fibrin Drugs 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000002565 heparin fraction Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 235000019626 lipase activity Nutrition 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000011197 physicochemical method Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010051055 Deep vein thrombosis Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-HNFCZKTMSA-N L-idopyranuronic acid Chemical compound OC1O[C@@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-HNFCZKTMSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 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 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000007068 beta-elimination reaction Methods 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
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- 229940088598 enzyme Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 238000005194 fractionation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- 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
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Public Health (AREA)
- Materials Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8221934A FR2538404B1 (enExample) | 1982-12-28 | 1982-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ206697A true NZ206697A (en) | 1986-10-08 |
Family
ID=9280592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ206697A NZ206697A (en) | 1982-12-28 | 1983-12-22 | Depolymerised and supersulphated heparin and pharmaceutical compositions |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4727063A (enExample) |
| EP (1) | EP0116801B1 (enExample) |
| JP (2) | JPH0629282B2 (enExample) |
| KR (1) | KR910008329B1 (enExample) |
| AT (1) | ATE26281T1 (enExample) |
| AU (1) | AU563289B2 (enExample) |
| CA (1) | CA1210760A (enExample) |
| DE (1) | DE3370632D1 (enExample) |
| DK (1) | DK597983A (enExample) |
| FR (1) | FR2538404B1 (enExample) |
| IE (1) | IE56566B1 (enExample) |
| IL (1) | IL70512A (enExample) |
| NZ (1) | NZ206697A (enExample) |
| ZA (2) | ZA839651B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5550116A (en) * | 1990-12-03 | 1996-08-27 | Sanofi | N,O-sulphated heparosans and pharmaceutical compositions containing them |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2555993B1 (fr) * | 1983-12-06 | 1986-11-07 | Anic Spa | Chitosanes 6-sulfates et procede pour leur preparation |
| US4948881A (en) * | 1982-12-28 | 1990-08-14 | Sanofi | Process for the depolymerization and sulfation of polysaccharides |
| IT1163772B (it) * | 1983-07-13 | 1987-04-08 | Baldacci Lab Spa | Oligosaccaridi eterogenei complessabili ed alfa-idosani ad attivita' terapeutica, procedimento per la loro preparazione e relative composizioni farmaceutiche |
| IT1214609B (it) * | 1985-05-17 | 1990-01-18 | Opocrin Spa | Esosaminoglicani solfati depolimerizzati ad attivita'antitrombotica, fibrinolitica, antinfiammatoria, loro procedimento di preparazione e composizioni farmaceutiche che li contengono. |
| FR2584728B1 (fr) * | 1985-07-12 | 1987-11-20 | Choay Sa | Procede de sulfatation de glycosaminoglycanes et de leurs fragments |
| US5262403A (en) * | 1986-03-10 | 1993-11-16 | Board Of Regents, The University Of Texas System | Glycosaminoglycan derivatives and their use as inhibitors of tumor invasiveness of metastatic profusion-II |
| AR243204A1 (es) * | 1986-11-21 | 1993-07-30 | Ajorca Sa | Un metodo para la depolimerizacion quimica de polisacaridos. |
| EP0356435B1 (en) * | 1987-03-19 | 1995-10-18 | Arthropharm Pty. Limited | Anti-inflammatory compounds and compositions |
| US5668116A (en) * | 1987-03-19 | 1997-09-16 | Anthropharm Pty. Limited | Anti-inflammatory compounds and compositions |
| DE3744119A1 (de) * | 1987-12-24 | 1989-07-06 | Basf Ag | Verwendung von polysulfatierten heparinen |
| AU3434889A (en) * | 1988-03-15 | 1989-10-05 | Jewish Hospital Of St. Louis, The | Inhibition of intestinal cholesterol and fatty acid absorption |
| US4945086A (en) * | 1988-05-03 | 1990-07-31 | The Board Of Trustees Of The Leland Stanford Junior University | Smooth muscle cell growth inhibitor |
| AU630359B2 (en) * | 1988-06-03 | 1992-10-29 | Italfarmaco S.P.A. | Glycosaminoglycan salts, processes for the preparation thereof and pharmaceutical compositions containing them |
| US5484777A (en) * | 1989-04-20 | 1996-01-16 | Lange, Iii; Louis G. | Pancreatic cholesterol esterase inhibitor |
| US5017565A (en) * | 1989-04-20 | 1991-05-21 | Lange Iii Louis G | Use of sulfated polysaccharides to inhibit pancreatic cholesterol esterase |
| US5063210A (en) * | 1989-04-20 | 1991-11-05 | Lange Iii Louis G | Use of sulfated polysaccharides to decrease cholesterol and fatty acid absorption |
| US5340932A (en) * | 1989-08-18 | 1994-08-23 | Ajorca S.A. | Substances with heparin-like structure and their method of production |
| DE69005251T2 (de) * | 1989-10-04 | 1994-05-05 | Akzo Nv | Sulfatierte Glykosaminoglykuronane mit antithrombotischer Wirkung. |
| IT1237518B (it) * | 1989-11-24 | 1993-06-08 | Renato Conti | Eparine supersolfatate |
| WO1991015217A1 (en) * | 1990-04-06 | 1991-10-17 | Washington University | Anticoagulant oligosaccharides |
| IT1243987B (it) * | 1990-10-29 | 1994-06-28 | Derivati Organici Lab | Procedimento per la preparazione di epossi-eparidi prodotti ottenuti ecomposizioni farmaceutiche che li contengono |
| IT1244373B (it) * | 1991-01-18 | 1994-07-08 | Sclavo Spa | Composizioni farmaceutiche per uso orale contenenti eparina a basso peso molecolare, loro preparazione ed uso |
| SE9101155D0 (sv) * | 1991-04-18 | 1991-04-18 | Kabi Pharmacia Ab | Novel heparin derivatives |
| GB9206291D0 (en) * | 1992-03-23 | 1992-05-06 | Cancer Res Campaign Tech | Oligosaccharides having growth factor binding affinity |
| US6750207B1 (en) | 1992-05-01 | 2004-06-15 | Yeda Research And Development Co. Ltd. | Compositions for the regulation of cytokine activity |
| US5861382A (en) * | 1992-05-01 | 1999-01-19 | Yeda Research And Development Co. Ltd. | Methods for regulation of active TNF-α |
| NZ258367A (en) * | 1992-11-10 | 1997-02-24 | Yeda Res & Dev | Oligosaccharide compositions comprising carboxylated and/or sulphated oligosaccharides for use in regulating tnf alpha production |
| FR2704861B1 (fr) * | 1993-05-07 | 1995-07-28 | Sanofi Elf | Fractions d'héparine purifiées, procédé d'obtention et compositions pharmaceutiques les contenant. |
| WO1995033468A1 (en) * | 1994-06-06 | 1995-12-14 | Oestergaard Per Bjoern | A pharmaceutical composition comprising oligosaccharides binding to lipoprotein lipase |
| AU682792B2 (en) | 1994-10-13 | 1997-10-16 | Cv Therapeutics, Inc. | Method of manufacturing non-absorbable synthetic sulfated polysaccharides |
| US5922690A (en) * | 1996-04-25 | 1999-07-13 | Van Gorp; Cornelius L. | Dermatan disulfate, an inhibitor of thrombin generation and activation |
| AU3596797A (en) | 1996-07-09 | 1998-02-02 | Keith A. Crutcher | Methods for the treatment of apolipoprotein e related diseases |
| IT1290814B1 (it) * | 1997-03-24 | 1998-12-11 | Istituto Scient Di Chimica E B | Glicosaminoglicani aventi elevata attivita' antitrombotica |
| US6388060B1 (en) | 1998-11-06 | 2002-05-14 | Vascular Therapeutics Inc. | Process for the sulfation of uronic acid-containing polysaccharides |
| DE29900874U1 (de) | 1999-01-20 | 1999-07-22 | Knoll AG, 67061 Ludwigshafen | Organprotektive Lösungen |
| US6409987B1 (en) | 1999-04-07 | 2002-06-25 | Intimax Corporation | Targeted agents useful for diagnostic and therapeutic applications |
| BR0012202A (pt) * | 1999-06-30 | 2002-04-02 | Hamilton Civic Hospitals Res | Composições de heparina de peso molecular médio (mmwh), método de tratamento de uma condição trombótica, método de prevenção da formação de um trombo, método de inibição da formação de trombos, composição farmacêutica, método de tratamento de trombose venosa profunda, método de prevenção de embolia pulmonar, método de preparação e usos de uma composição de mmwh |
| US8227449B2 (en) | 2000-03-30 | 2012-07-24 | Glycores 2000 S.R.L. | Glycosaminoglycans derived from K5 polysaccharide having high anticoagulant and antithrombotic activities and process for their preparation |
| FR2807918B1 (fr) | 2000-04-21 | 2003-07-04 | Equip Tech Ind Alimentaires | Retourneur avec galets mobiles sur surfaces de guidage |
| IL154771A0 (en) * | 2000-09-08 | 2003-10-31 | Hamilton Civic Hospitals Res | Antithrombotic compositions |
| KR20040066090A (ko) * | 2001-08-31 | 2004-07-23 | 아이박스 리서치, 인코포레이티드 | 사카라이드를 황산화시키기 위한 방법 |
| US7285536B2 (en) * | 2001-12-05 | 2007-10-23 | Yeda Research And Development Co., Ltd. | Anti-cancer therapeutic compounds |
| US8071569B2 (en) * | 2002-09-20 | 2011-12-06 | Mousa Shaker A | Oxidized heparin fractions and their use in inhibiting angiogenesis |
| JP4636818B2 (ja) * | 2004-06-07 | 2011-02-23 | マルホ株式会社 | 多硫酸化コンドロイチン硫酸の製造方法 |
| AU2005265412B2 (en) * | 2004-07-19 | 2010-09-02 | Onconova Therapeutics, Inc. | Formulations for parenteral administration of (e)-2,6-dialkoxystyryl 4-substituted benzylsulfones |
| ES2299795T3 (es) * | 2004-09-13 | 2008-06-01 | Laboratori Derivati Organici S.P.A. | Procedimiento de sulfatacion de la condroitina. |
| AU2006275822B2 (en) * | 2005-07-29 | 2012-02-02 | Onconova Therapeutics, Inc. | Formulation of radioprotective alpha, beta unsaturated aryl sulfones |
| EP2046343B1 (en) * | 2006-07-28 | 2014-05-14 | Onconova Therapeutics, Inc. | Formulations of radioprotective alpha, beta unsaturated aryl sulfones |
| ES2567079T3 (es) * | 2007-11-02 | 2016-04-19 | Momenta Pharmaceuticals, Inc. | Composiciones de polisacáridos que no son anticoagulantes |
| US8592393B2 (en) * | 2007-11-02 | 2013-11-26 | Momenta Pharmaceuticals, Inc. | Polysaccharide compositions and methods of use for the treatment and prevention of disorders associated with progenitor cell mobilization |
| US8569262B2 (en) | 2007-11-02 | 2013-10-29 | Momenta Pharmaceuticals, Inc. | Polysaccharide compositions and methods of use for the treatment and prevention of disorders associated with progenitor cell mobilization |
| RU2408379C2 (ru) * | 2009-03-04 | 2011-01-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Антикоагулянтное средство с противовоспалительной и противоопухолевой активностью |
| CN101597343B (zh) * | 2009-05-07 | 2011-06-15 | 张丽萍 | 一种低分子肝素的基团修饰方法 |
| BR112012026542A2 (pt) | 2010-04-16 | 2016-07-12 | Momenta Pharmaceuticals Inc | abordagem seletiva de tecido |
| WO2011159770A2 (en) | 2010-06-17 | 2011-12-22 | Momenta Pharmaceuticals, Inc. | Methods and compositions for modulating hair growth |
| PH12013502361A1 (en) * | 2011-05-20 | 2014-01-27 | Gnosis Spa | Shark-like chondroitin sulphate and process for the preparation thereof |
| JP2016520613A (ja) | 2013-05-28 | 2016-07-14 | モメンタ ファーマシューティカルズ インコーポレイテッド | 薬学的組成物 |
| CN103833869B (zh) * | 2014-02-26 | 2016-01-20 | 上海中医药大学 | 一种木香硫酸化多糖及其制备方法和用途 |
| US20190002596A1 (en) * | 2015-12-30 | 2019-01-03 | Shenzhen Hepalink Pharmaceutical Group Co., Ltd. | Sulfated heparin oligosaccharide and preparation method and application thereof |
| JP6225321B1 (ja) | 2016-08-31 | 2017-11-08 | 王子ホールディングス株式会社 | ポリ硫酸ペントサンの製造方法 |
| CN111148749A (zh) | 2016-08-31 | 2020-05-12 | 王子控股株式会社 | 酸性低聚木糖的生产方法和酸性低聚木糖 |
| JP6281659B1 (ja) | 2017-02-28 | 2018-02-21 | 王子ホールディングス株式会社 | ポリ硫酸ペントサン、医薬組成物及び抗凝固剤 |
| SG11201911318SA (en) | 2017-05-31 | 2020-01-30 | Oji Holdings Corp | Moisturizing topical preparation |
| AU2018333249B2 (en) | 2017-09-12 | 2023-03-02 | Oji Holdings Corporation | Pentosan polysulfate and method for producing pentosan polysulfate |
| ES2946281T3 (es) | 2017-12-20 | 2023-07-14 | Oji Holdings Corp | Pentosano polisulfato y medicamento que contiene pentosano polisulfato |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE498062A (enExample) * | ||||
| US2599172A (en) * | 1948-11-29 | 1952-06-03 | Searle & Co | Sulfuric acid esters of hyaluronic acid and processes for the production thereof |
| CH277483A (de) * | 1949-10-20 | 1951-08-31 | Hoffmann La Roche | Verfahren zur Herstellung eines hochaktiven blutgerinnungshemmenden Mittels. |
| US2697093A (en) * | 1949-12-16 | 1954-12-14 | Phillips Petroleum Co | Process for production of alkali metal polysaccharide sulfates |
| US2755275A (en) * | 1952-08-29 | 1956-07-17 | Abbott Lab | Process for sulfating chitin |
| ES343957A1 (es) * | 1967-08-09 | 1968-10-01 | Rocador Sa | Procedimiento de obtencion de polisacaridos sulfatados an- tilipemicos activos por via oral. |
| JPS5027884A (enExample) * | 1973-07-12 | 1975-03-22 | ||
| IT1083903B (it) * | 1977-08-09 | 1985-05-25 | Lobo Srl | Oligo-eteropolisaccaridi con attivita' eparinosimili,procedimento per il loro ottenimento e relative composizioni terapeutiche |
| SE7811306L (sv) * | 1978-11-01 | 1980-05-02 | Rothman Gunnvor | Antikoagulationsmedel samt sett for dess framstellning |
| CA1136620A (en) * | 1979-01-08 | 1982-11-30 | Ulf P.F. Lindahl | Heparin fragments having selective anticoagulation activity |
| US4281168A (en) * | 1979-04-02 | 1981-07-28 | The Upjohn Company | 11-Deoxy-inter-oxa-19-oxo-PGE1 compounds |
| JPS56803A (en) * | 1979-06-18 | 1981-01-07 | Mitsubishi Chem Ind Ltd | Preparation of vegetable polysaccharide sulfate ester |
| US4266077A (en) * | 1979-12-26 | 1981-05-05 | American Cyanamid Company | Naphthalenetetrayltetrakis(sulfonylimino)-aryl multicarboxylic acids and salts thereof |
| JPS56120704A (en) * | 1980-01-28 | 1981-09-22 | Hepar Ind Inc | Method of obtaining low molecular weight heparin having heightened pharmacologic property* product manufactured thereby and its use |
| US4281108A (en) * | 1980-01-28 | 1981-07-28 | Hepar Industries, Inc. | Process for obtaining low molecular weight heparins endowed with elevated pharmacological properties, and product so obtained |
| IL70511A (en) | 1982-12-28 | 1990-01-18 | Anic Spa | Process for the concurrent depolymerization and sulfation of polysaccharides at hydroxyl groups |
-
1982
- 1982-12-28 FR FR8221934A patent/FR2538404B1/fr not_active Expired
-
1983
- 1983-12-21 CA CA000443860A patent/CA1210760A/en not_active Expired
- 1983-12-21 IL IL70512A patent/IL70512A/xx not_active IP Right Cessation
- 1983-12-22 NZ NZ206697A patent/NZ206697A/en unknown
- 1983-12-23 AU AU22855/83A patent/AU563289B2/en not_active Ceased
- 1983-12-23 DK DK597983A patent/DK597983A/da not_active Application Discontinuation
- 1983-12-23 IE IE3062/83A patent/IE56566B1/en not_active IP Right Cessation
- 1983-12-26 DE DE8383402533T patent/DE3370632D1/de not_active Expired
- 1983-12-26 EP EP83402533A patent/EP0116801B1/fr not_active Expired
- 1983-12-26 AT AT83402533T patent/ATE26281T1/de active
- 1983-12-27 KR KR1019830006212A patent/KR910008329B1/ko not_active Expired
- 1983-12-28 ZA ZA839651A patent/ZA839651B/xx unknown
- 1983-12-28 JP JP58252446A patent/JPH0629282B2/ja not_active Expired - Lifetime
- 1983-12-28 ZA ZA839652A patent/ZA839652B/xx unknown
- 1983-12-28 JP JP58252447A patent/JPS59133201A/ja active Pending
-
1985
- 1985-05-24 US US06/737,496 patent/US4727063A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5550116A (en) * | 1990-12-03 | 1996-08-27 | Sanofi | N,O-sulphated heparosans and pharmaceutical compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| US4727063A (en) | 1988-02-23 |
| KR840006812A (ko) | 1984-12-03 |
| IL70512A0 (en) | 1984-03-30 |
| FR2538404A1 (enExample) | 1984-06-29 |
| JPS59133201A (ja) | 1984-07-31 |
| ATE26281T1 (de) | 1987-04-15 |
| DK597983A (da) | 1984-06-29 |
| EP0116801B1 (fr) | 1987-04-01 |
| DK597983D0 (da) | 1983-12-23 |
| JPS59133202A (ja) | 1984-07-31 |
| IL70512A (en) | 1989-08-15 |
| JPH0629282B2 (ja) | 1994-04-20 |
| EP0116801A1 (fr) | 1984-08-29 |
| AU563289B2 (en) | 1987-07-02 |
| DE3370632D1 (en) | 1987-05-07 |
| FR2538404B1 (enExample) | 1985-08-23 |
| IE56566B1 (en) | 1991-09-11 |
| IE833062L (en) | 1984-06-28 |
| AU2285583A (en) | 1984-07-05 |
| ZA839652B (en) | 1984-08-29 |
| ZA839651B (en) | 1985-02-27 |
| KR910008329B1 (ko) | 1991-10-12 |
| CA1210760A (en) | 1986-09-02 |
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