NZ207622A - Xylane sulphates and pharmaceutical compositions - Google Patents
Xylane sulphates and pharmaceutical compositionsInfo
- Publication number
- NZ207622A NZ207622A NZ207622A NZ20762284A NZ207622A NZ 207622 A NZ207622 A NZ 207622A NZ 207622 A NZ207622 A NZ 207622A NZ 20762284 A NZ20762284 A NZ 20762284A NZ 207622 A NZ207622 A NZ 207622A
- Authority
- NZ
- New Zealand
- Prior art keywords
- xylane
- solution
- weight
- sulfatation
- xxx
- Prior art date
Links
- 150000003467 sulfuric acid derivatives Chemical class 0.000 title claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000005194 fractionation Methods 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 13
- 230000002785 anti-thrombosis Effects 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- 238000000108 ultra-filtration Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 150000002972 pentoses Chemical class 0.000 claims description 11
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical compound CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000000055 hyoplipidemic effect Effects 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- PINRUEQFGKWBTO-UHFFFAOYSA-N 3-methyl-5-phenyl-1,3-oxazolidin-2-imine Chemical compound O1C(=N)N(C)CC1C1=CC=CC=C1 PINRUEQFGKWBTO-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 108010013563 Lipoprotein Lipase Proteins 0.000 claims 1
- 102000043296 Lipoprotein lipases Human genes 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 206010003230 arteritis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 238000001631 haemodialysis Methods 0.000 claims 1
- 230000000322 hemodialysis Effects 0.000 claims 1
- 210000003141 lower extremity Anatomy 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 239000003524 antilipemic agent Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 38
- 239000012153 distilled water Substances 0.000 description 32
- 239000011780 sodium chloride Substances 0.000 description 19
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000012510 hollow fiber Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 239000003480 eluent Substances 0.000 description 10
- 229940097043 glucuronic acid Drugs 0.000 description 10
- 230000000717 retained effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 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 description 8
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 8
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 229920000669 heparin Polymers 0.000 description 8
- 229960002897 heparin Drugs 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical class CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 239000003146 anticoagulant agent Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 230000007928 solubilization Effects 0.000 description 4
- 238000005063 solubilization Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940127219 anticoagulant drug Drugs 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000020764 fibrinolysis Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010074860 Factor Xa Proteins 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
- 102000005686 Serum Globulins Human genes 0.000 description 2
- 108010045362 Serum Globulins Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001858 anti-Xa Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000003480 fibrinolytic effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 230000002008 hemorrhagic effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 235000019626 lipase activity Nutrition 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- -1 polysaccharide sulfates Chemical class 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 230000009424 thromboembolic effect Effects 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 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
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- 206010051055 Deep vein thrombosis Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000009233 Stachytarpheta cayennensis Nutrition 0.000 description 1
- 241000862969 Stella Species 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 229940127090 anticoagulant agent Drugs 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- OOULUYZFLXDWDQ-UHFFFAOYSA-L barium perchlorate Chemical compound [Ba+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O OOULUYZFLXDWDQ-UHFFFAOYSA-L 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 208000001297 phlebitis Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 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
- C08B37/14—Hemicellulose; 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
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
-
- 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
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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Pharmacology & Pharmacy (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Detergent Compositions (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8305170A FR2543145B1 (fr) | 1983-03-24 | 1983-03-24 | Nouveaux sulfates de xylanes, leur procede de preparation et leur activite anti-thrombotique et hypolipemiante |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ207622A true NZ207622A (en) | 1986-08-08 |
Family
ID=9287351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ207622A NZ207622A (en) | 1983-03-24 | 1984-03-23 | Xylane sulphates and pharmaceutical compositions |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4699900A (en, 2012) |
| EP (1) | EP0125152B1 (en, 2012) |
| JP (1) | JPS6063203A (en, 2012) |
| KR (1) | KR860001394B1 (en, 2012) |
| AT (1) | ATE24520T1 (en, 2012) |
| AU (1) | AU561588B2 (en, 2012) |
| CA (1) | CA1221090A (en, 2012) |
| DE (1) | DE3461808D1 (en, 2012) |
| DK (1) | DK55784A (en, 2012) |
| ES (1) | ES8500962A1 (en, 2012) |
| FR (1) | FR2543145B1 (en, 2012) |
| GR (1) | GR79831B (en, 2012) |
| IL (1) | IL70846A0 (en, 2012) |
| NZ (1) | NZ207622A (en, 2012) |
| PT (1) | PT78179B (en, 2012) |
| ZA (1) | ZA842176B (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2543145B1 (fr) * | 1983-03-24 | 1986-10-17 | Sanofi Sa | Nouveaux sulfates de xylanes, leur procede de preparation et leur activite anti-thrombotique et hypolipemiante |
| FR2572731B1 (fr) * | 1984-11-07 | 1987-03-06 | Sanofi Sa | Nouveaux sulfates de xylanes de bas poids moleculaires, leur procede de preparation et leur activite antithrombotique et hypolipemiante par voie orale |
| FR2574663B1 (fr) * | 1984-12-17 | 1987-01-16 | Sanofi Sa | Nouvelle composition therapeutique a activite antithrombotique et hypolipemiante a base de xylanes et d'un acide organique |
| US4820693A (en) * | 1986-05-22 | 1989-04-11 | Angiogenics, Ltd. | Method and composition for arresting angiogenesis and capillary, cell or membrane leakage |
| US4966890A (en) * | 1986-04-04 | 1990-10-30 | Angiogenics, Ltd. | Method and composition for arresting angiogenesis and capillary, cell or membrane leakage |
| US5063210A (en) * | 1989-04-20 | 1991-11-05 | Lange Iii Louis G | Use of sulfated polysaccharides to decrease cholesterol and fatty acid absorption |
| US5017565A (en) * | 1989-04-20 | 1991-05-21 | Lange Iii Louis G | Use of sulfated polysaccharides to inhibit pancreatic cholesterol esterase |
| US5484777A (en) * | 1989-04-20 | 1996-01-16 | Lange, Iii; Louis G. | Pancreatic cholesterol esterase inhibitor |
| DE3917982A1 (de) * | 1989-06-02 | 1990-12-06 | Behringwerke Ag | Verwendung von xylanpolyhydrogensulfaten zur therapie von zellproliferations-bedingten erkrankungen |
| FR2655267B1 (fr) * | 1989-12-04 | 1992-04-03 | Roussel Uclaf | Nouveau derive sulfate du galactanne extrait de klebsiella, procede de preparation, application a titre de medicaments et compositions pharmaceutiques le renfermant. |
| US5141928B1 (en) * | 1989-12-20 | 1995-11-14 | Brujo Inc | Ophthalmic medication |
| US5382570A (en) * | 1990-04-23 | 1995-01-17 | Akzo, N.V. | Sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type |
| US5378829A (en) * | 1990-04-23 | 1995-01-03 | Akzo N.V. | Sulfated glycosaminoglycanoid derivatives of the heparin and heparan sulfate type |
| US5668274A (en) * | 1991-04-23 | 1997-09-16 | Akzo Nobel N.V. | Sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type |
| IL102758A (en) * | 1991-08-23 | 1997-03-18 | Akzo Nv | Glycosaminoglycanoid derivatives, their preparation and pharmaceutical compositions comprising them |
| US5639469A (en) * | 1994-06-15 | 1997-06-17 | Minnesota Mining And Manufacturing Company | Transmucosal delivery system |
| US6255295B1 (en) | 1996-12-23 | 2001-07-03 | Nutramax Laboratories, Inc. | Aminosugar, glycosaminoglycan or glycosaminoglycan-like compounds, and s-adenosylmethionine composition for the protection, treatment, repair, and reduction of inflammation of connective tissue |
| US20070141181A1 (en) * | 1998-02-13 | 2007-06-21 | Nutramax Laboratories, Inc. | Use of anabolic agents, anti-catabolic agents, antioxidant agents, and analgesics for protection, treatment and repair of connective tissues in humans and animals |
| US6797289B2 (en) * | 1998-02-13 | 2004-09-28 | Nutramax Laboratories, Inc. | Use of anabolic agents, anti-catabolic agents, antioxidant agents, and analgesics for protection, treatment and repair of connective tissues in humans and animals |
| US6451771B1 (en) | 1999-02-12 | 2002-09-17 | Nutramax Laboratories, Inc. | Use of anabolic agents anti-catabolic agents and antioxidant agents for protection treatment and repair of connective tissues in humans and animals |
| ES2251289B1 (es) * | 2004-02-27 | 2007-07-01 | Bioiberica, S.A. | Nuevo uso terapeutico de un grupo de polisacaridos sulfatados. |
| WO2009047699A1 (en) * | 2007-10-10 | 2009-04-16 | Alembic Limited | An improved process for the preparation of an amorphous form of pentosan polysulfate or salts thereof |
| AU2008100725B4 (en) * | 2008-07-04 | 2008-10-02 | Parnell Technologies Pty Ltd | A sulfated polysaccharide compound for clinical use |
| WO2011088418A2 (en) * | 2010-01-15 | 2011-07-21 | Mount Sinai School Of Medicine | Inhibition of tnf-alpha induced activation of nfkb by pentosan polysulfate |
| WO2012101544A1 (en) * | 2011-01-29 | 2012-08-02 | Alembic Pharmaceuticals Limited | An improved process for the preparation of pentosan polysulfate or salts thereof |
| WO2012114349A1 (en) * | 2011-02-23 | 2012-08-30 | Cadila Healthcare Limited | An improved process for the preparation of pentosan polysulfate sodium |
| 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 |
| BR112020003908B1 (pt) | 2016-08-31 | 2023-01-24 | Oji Holdings Corporation | Método para produzir um ingrediente farmacêutico ativo incluindo polissulfato de pentosano |
| 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 |
| MX390883B (es) | 2017-05-31 | 2025-03-21 | Oji Holdings Corp | Preparacion hidratante topica |
| BR112020004787A2 (pt) | 2017-09-12 | 2020-09-24 | Oji Holdings Corporation | polissulfato de pentosano, composição farmacêutica, anticoagulante, e, método para produzir polissulfato de pentosano |
| PT3730521T (pt) * | 2017-12-20 | 2023-06-19 | Oji Holdings Corp | Polissulfato de pentosano e medicamento contendo polissulfato de pentosano |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH290145A (de) * | 1944-06-13 | 1953-04-15 | Kaulla Kurt Nikolai Dr Med Von | Verfahren zur Herstellung von Schwefelsäureestern des Xylans. |
| FR1050576A (fr) * | 1951-02-06 | 1954-01-08 | Wander Ag Dr A | Procédé pour la préparation de sels alcalins de l'ester sulfurique du xylane |
| US3290263A (en) * | 1962-08-02 | 1966-12-06 | Colonial Sugar Refining Co | Process of reacting sugars with reagents wherein the sugar is dissolved in monohydric alcohols containing grouping |
| ES343957A1 (es) * | 1967-08-09 | 1968-10-01 | Rocador Sa | Procedimiento de obtencion de polisacaridos sulfatados an- tilipemicos activos por via oral. |
| US4098995A (en) * | 1976-07-12 | 1978-07-04 | American Cyanamid Company | Polygalactosido-sucrose poly(h-)sulfate salts |
| US4301153A (en) * | 1977-03-21 | 1981-11-17 | Riker Laboratories, Inc. | Heparin preparation |
| US4122250A (en) * | 1977-08-22 | 1978-10-24 | Gottfried Schmer | Separation of high-activity heparin by affinity chromatography |
| US4221907A (en) * | 1979-07-09 | 1980-09-09 | American Cyanamid Company | Substituted O-α-D and O-β-D-multi-galactopyranosyl and glucopyranosyl 1→4 and 1→6 galactopyranosyl 1→6 α-D-glucopyranoses |
| DE2945595A1 (de) * | 1979-11-12 | 1981-05-21 | Sandoz-Patent-GmbH, 7850 Lörrach | Verfahren zur herstellung von niedermolekularem heparin bzw. seinen salzen |
| 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 |
| FR2543145B1 (fr) * | 1983-03-24 | 1986-10-17 | Sanofi Sa | Nouveaux sulfates de xylanes, leur procede de preparation et leur activite anti-thrombotique et hypolipemiante |
-
1983
- 1983-03-24 FR FR8305170A patent/FR2543145B1/fr not_active Expired
-
1984
- 1984-02-01 IL IL70846A patent/IL70846A0/xx unknown
- 1984-02-08 DK DK55784A patent/DK55784A/da not_active Application Discontinuation
- 1984-02-09 AU AU24412/84A patent/AU561588B2/en not_active Ceased
- 1984-03-01 PT PT78179A patent/PT78179B/pt unknown
- 1984-03-02 ES ES530266A patent/ES8500962A1/es not_active Expired
- 1984-03-02 GR GR73987A patent/GR79831B/el unknown
- 1984-03-05 DE DE8484400438T patent/DE3461808D1/de not_active Expired
- 1984-03-05 AT AT84400438T patent/ATE24520T1/de not_active IP Right Cessation
- 1984-03-05 EP EP84400438A patent/EP0125152B1/fr not_active Expired
- 1984-03-12 CA CA000449345A patent/CA1221090A/fr not_active Expired
- 1984-03-21 KR KR1019840001491A patent/KR860001394B1/ko not_active Expired
- 1984-03-23 US US06/592,527 patent/US4699900A/en not_active Expired - Fee Related
- 1984-03-23 NZ NZ207622A patent/NZ207622A/en unknown
- 1984-03-23 ZA ZA842176A patent/ZA842176B/xx unknown
- 1984-03-24 JP JP59057193A patent/JPS6063203A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3461808D1 (en) | 1987-02-05 |
| IL70846A0 (en) | 1984-05-31 |
| ZA842176B (en) | 1984-10-31 |
| EP0125152B1 (fr) | 1986-12-30 |
| KR840008376A (ko) | 1984-12-14 |
| US4699900A (en) | 1987-10-13 |
| AU561588B2 (en) | 1987-05-14 |
| DK55784A (da) | 1984-09-25 |
| ES530266A0 (es) | 1984-11-01 |
| ES8500962A1 (es) | 1984-11-01 |
| CA1221090A (fr) | 1987-04-28 |
| KR860001394B1 (ko) | 1986-09-22 |
| DK55784D0 (da) | 1984-02-08 |
| AU2441284A (en) | 1984-09-27 |
| JPS6063203A (ja) | 1985-04-11 |
| FR2543145A1 (fr) | 1984-09-28 |
| FR2543145B1 (fr) | 1986-10-17 |
| EP0125152A1 (fr) | 1984-11-14 |
| ATE24520T1 (de) | 1987-01-15 |
| PT78179B (fr) | 1986-04-24 |
| GR79831B (en, 2012) | 1984-10-31 |
| PT78179A (fr) | 1984-04-01 |
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