ZA200301692B - Polysaccharides with antithrombotic activity comprising at least a covalent bond with biotin or a biotin derivative. - Google Patents
Polysaccharides with antithrombotic activity comprising at least a covalent bond with biotin or a biotin derivative. Download PDFInfo
- Publication number
- ZA200301692B ZA200301692B ZA200301692A ZA200301692A ZA200301692B ZA 200301692 B ZA200301692 B ZA 200301692B ZA 200301692 A ZA200301692 A ZA 200301692A ZA 200301692 A ZA200301692 A ZA 200301692A ZA 200301692 B ZA200301692 B ZA 200301692B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- tri
- glucopyranosyl
- sulphonato
- group
- Prior art date
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- 150000004676 glycans Chemical class 0.000 title claims description 48
- 229920001282 polysaccharide Polymers 0.000 title claims description 43
- 239000005017 polysaccharide Substances 0.000 title claims description 43
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 title claims description 33
- 229960002685 biotin Drugs 0.000 title claims description 17
- 235000020958 biotin Nutrition 0.000 title claims description 17
- 239000011616 biotin Substances 0.000 title claims description 17
- 150000001615 biotins Chemical class 0.000 title claims description 15
- 230000002785 anti-thrombosis Effects 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 claims description 68
- 239000002253 acid Substances 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 29
- 150000002772 monosaccharides Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 159000000000 sodium salts Chemical class 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 108090001008 Avidin Proteins 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 8
- 230000009424 thromboembolic effect Effects 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 108010090804 Streptavidin Proteins 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 230000015271 coagulation Effects 0.000 claims description 6
- 238000005345 coagulation Methods 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 230000007170 pathology Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000003132 pyranosyl group Chemical group 0.000 claims description 5
- 238000013171 endarterectomy Methods 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 150000008266 deoxy sugars Chemical class 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 150000002402 hexoses Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000003780 insertion Methods 0.000 claims description 3
- 230000037431 insertion Effects 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- 150000002972 pentoses Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 206010002388 Angina unstable Diseases 0.000 claims description 2
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 2
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 206010061216 Infarction Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 2
- 208000010378 Pulmonary Embolism Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 230000002255 enzymatic effect Effects 0.000 claims description 2
- 238000001631 haemodialysis Methods 0.000 claims description 2
- 230000013632 homeostatic process Effects 0.000 claims description 2
- 230000007574 infarction Effects 0.000 claims description 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 230000001732 thrombotic effect Effects 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 1
- 241000766754 Agra Species 0.000 claims 1
- 125000005640 glucopyranosyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 79
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 50
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 239000000741 silica gel Substances 0.000 description 40
- 229910002027 silica gel Inorganic materials 0.000 description 40
- 150000001875 compounds Chemical class 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- -1 for example Chemical class 0.000 description 32
- 239000000203 mixture Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000004809 thin layer chromatography Methods 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 238000004587 chromatography analysis Methods 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 150000002482 oligosaccharides Polymers 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 229920001542 oligosaccharide Polymers 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000003146 anticoagulant agent Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 229920005654 Sephadex Polymers 0.000 description 10
- 239000012507 Sephadexâą Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 229960002897 heparin Drugs 0.000 description 8
- 229920000669 heparin Polymers 0.000 description 8
- 229940127219 anticoagulant drug Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000002808 molecular sieve Substances 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 108090000190 Thrombin Proteins 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229960004072 thrombin Drugs 0.000 description 6
- 108010074860 Factor Xa Proteins 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 150000004804 polysaccharides Polymers 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229930182475 S-glycoside Natural products 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229960004676 antithrombotic agent Drugs 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003569 thioglycosides Chemical class 0.000 description 4
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004133 Sodium thiosulphate Substances 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 229940126540 compound 41 Drugs 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 3
- 229940127215 low-molecular weight heparin Drugs 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 3
- 239000001120 potassium sulphate Substances 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
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- Biochemistry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
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- Communicable Diseases (AREA)
- Obesity (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0012094A FR2814463B1 (fr) | 2000-09-22 | 2000-09-22 | Nouveaux polysaccharides a activite antithrombotique comprenant au moins une liaison covalente avec la biotine ou un derive de la biotine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200301692B true ZA200301692B (en) | 2004-03-01 |
Family
ID=8854579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200301692A ZA200301692B (en) | 2000-09-22 | 2003-02-28 | Polysaccharides with antithrombotic activity comprising at least a covalent bond with biotin or a biotin derivative. |
Country Status (39)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2814463B1 (fr) * | 2000-09-22 | 2002-11-15 | Sanofi Synthelabo | Nouveaux polysaccharides a activite antithrombotique comprenant au moins une liaison covalente avec la biotine ou un derive de la biotine |
| FR2874924B1 (fr) | 2004-09-09 | 2006-12-01 | Sanofi Aventis Sa | Hexadecasaccharides biotinyles, leur preparation et leur utilisation therapeutique |
| TWI403334B (zh) * | 2004-12-23 | 2013-08-01 | Merck Sharp & Dohme | ć ć«çç©çŽ æźćșäčæèĄæ ééæć¶ć |
| TWI376234B (en) * | 2005-02-01 | 2012-11-11 | Msd Oss Bv | Conjugates of a polypeptide and an oligosaccharide |
| UA94593C2 (ru) * | 2005-10-10 | 2011-05-25 | Đ.Đ. ĐŃĐłĐ°ĐœĐŸĐœ | ĐĐœŃĐžŃŃĐŸĐŒĐ±ĐŸĐ·ĐœŃĐ” ĐŽĐČĐŸĐčĐœŃĐ” ĐžĐœĐłĐžĐ±ĐžŃĐŸŃŃ Ń Đ±ĐžĐŸŃĐžĐœĐŸĐČĐŸĐč ĐŒĐ”ŃĐșĐŸĐč |
| HRP20110331T1 (hr) * | 2005-10-10 | 2011-06-30 | N.V. Organon | Antikoagulantno-antitrombotski dvojni inhibitori, koji sadrĆŸe biotinski biljeg |
| CN1317035C (zh) * | 2005-10-24 | 2007-05-23 | ć€©æŽ„ć€§ćŠ | ćșäșé °èŒćșçćŸźçČèĄšéąć€éçç©ćèœć ćç»èŁ æčæł |
| EP1886696A1 (en) * | 2006-08-03 | 2008-02-13 | Endotis Pharma | Conjugates of antithrombin binding oligosaccharide derivatives and therapeutic proteins |
| FR2912409B1 (fr) * | 2007-02-14 | 2012-08-24 | Sanofi Aventis | Heparines de bas poids moleculaire comprenant au moins une liaison covalente avec la biotine ou un derive de la biotine leur procede de preparation,leur utilisation |
| EP2145624A1 (en) | 2008-07-18 | 2010-01-20 | Sanofi-Aventis | Use of idrabiotaparinux for decreasing the incidence of bleedings during an antithrombotic treatment |
| EP2233143A1 (en) | 2009-03-24 | 2010-09-29 | Sanofi-Aventis | Use of idrabiotaparinux for decreasing the incidence of bleedings during an antithrombotic treatment |
| TW201006479A (en) * | 2008-07-18 | 2010-02-16 | Sanofi Aventis | Use of idrabiotaparinux for decreasing the incidence of bleedings during an antithrombotic treatment |
| FR2935386B1 (fr) * | 2008-08-26 | 2010-09-10 | Sanofi Aventis | Nouveaux polysaccharides a activite antithrombotique comprenant une liaion covalente avec une chaine amine |
| WO2010029552A1 (en) * | 2008-09-10 | 2010-03-18 | Transpharma Medical Ltd. | Transdermal delivery of oligosaccharides |
| JP5783908B2 (ja) | 2008-12-19 | 2015-09-24 | ăčăăŒăăč ăăĄăŒăă·ă„ăŒăăŁă«ă«ăș ă€ăłăłăŒăăŹă€ăăă | æ»ææ§ăæČ»çăăæčæł |
| FR2952935B1 (fr) | 2009-11-20 | 2011-12-02 | Sanofi Aventis | Procede de preparation du n-biotinyl-6-aminocaproate de n succinimidyle |
| CN102892411B (zh) | 2009-12-18 | 2015-01-21 | æ©ć€ææŻèŻäžć Źćž | ć«æćæçäœèçłçèŻç©ćŁæćć |
| CZ302669B6 (cs) * | 2010-03-29 | 2011-08-24 | Univerzita Palackého v Olomouci | Efektivnà zpusob biotinylace aminosloucenin pomocà syntézy na pevné fåzi pro potreby afinitnà chromatografie |
| CZ302510B6 (cs) * | 2010-03-29 | 2011-06-22 | Univerzita Palackého v Olomouci | Efektivnà zpusob biotinylace sloucenin s karboxylovou skupinou pomocà syntézy na pevné fåzi pro potreby afinitnà chromatografie |
| EP3572074B1 (en) | 2010-03-31 | 2021-01-06 | Supernus Pharmaceuticals, Inc. | Stabilized formulations of molindone |
| EP2614089A1 (fr) * | 2010-09-10 | 2013-07-17 | Sanofi-Aventis | Polysaccharides biotinyles a activite antithrombotique et presentant une stabilite metabolique amelioree |
| FR2964660B1 (fr) * | 2010-09-10 | 2012-09-28 | Sanofi Aventis | Nouveaux polysaccharides biotinyles a activite antithrombotique et presentant une stabilite metabolique amelioree |
| EP2484366A1 (en) | 2011-02-07 | 2012-08-08 | Sanofi | Idrabiotaparinux for the treatment of pulmonary embolism and for the secondary prevention of venous thromboembolic events |
| CN103917552B (zh) | 2011-06-17 | 2017-03-29 | ćĄćæą éșŠçčæŻć Źćž | ć ·æçćèĄ°æćé«æŽ»æ§çćæäșçł |
| EP3524251A1 (en) * | 2012-11-13 | 2019-08-14 | Supernus Pharmaceuticals, Inc. | Method of treatment of aggression |
| WO2015195404A1 (en) | 2014-06-20 | 2015-12-23 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Methods for detection of an analyte by movement of tethered microparticles |
| WO2016205239A1 (en) | 2015-06-15 | 2016-12-22 | The United States Of America, As Represented By The Secretary Department Of Health And Human Services | Non-hormonal mammalian sperm decoy contraception based on the n-terminus of the zp2 protein |
| WO2018076025A1 (en) | 2016-10-21 | 2018-04-26 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Molecular nanotags |
| CN108976318B (zh) * | 2017-06-01 | 2021-03-30 | éŠéœć»ç§ć€§ćŠ | ć-6-(çç©çŽ é °èșćș)-6-è±æ°§-ÎČ-çŻçłçČŸćć ¶ć¶ć€æčæłććșçš |
| WO2019133727A1 (en) | 2017-12-29 | 2019-07-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Universal influenza virus probe set for enrichment of any influenza virus nucleic acid |
| AU2020310172A1 (en) | 2019-07-09 | 2022-03-03 | Optimvia Llc | Methods for synthesizing anticoagulant polysaccharides |
| WO2021075165A1 (ja) * | 2019-10-17 | 2021-04-22 | æ ȘćŒäŒç€ŸăȘăŒăăăăăŻăŒăŻæèĄç 究æ | é ç·ăąăžă„ăŒă« |
| WO2022056078A1 (en) | 2020-09-11 | 2022-03-17 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Rnase h-assisted detection assay for rna (radar) |
| WO2024191684A1 (en) | 2023-03-10 | 2024-09-19 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Detection of hepatitis c virus ribonucleic acid from whole blood using reverse transcription loop-mediated isothermal amplification |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960884A (en) * | 1974-04-24 | 1976-06-01 | Sergei Ivanovich Zavyalov | Method of preparing racemic biotin |
| AU563351C (en) * | 1982-01-15 | 2003-06-19 | Glaxo Group Limited | Synthesis of oligosaccharides |
| IL102758A (en) * | 1991-08-23 | 1997-03-18 | Akzo Nv | Glycosaminoglycanoid derivatives, their preparation and pharmaceutical compositions comprising them |
| US20010023288A1 (en) * | 1999-07-07 | 2001-09-20 | Wilbur D. Scott | Trifunctional reagent for conjugation to a biomolecule |
| WO2000002050A1 (en) * | 1998-07-07 | 2000-01-13 | Department Of Radiation Oncology, University Of Washington | Trifunctional reagent for conjugation to a biomolecule |
| FR2751334B1 (fr) * | 1996-07-19 | 1998-10-16 | Sanofi Sa | Polysaccharides synthetiques, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2773801B1 (fr) * | 1998-01-19 | 2000-05-12 | Sanofi Sa | Nouveaux pentasaccharides, procedes pour leurs preparations et compositions pharmaceutiques les contenant |
| FR2773804B1 (fr) * | 1998-01-19 | 2000-02-18 | Sanofi Sa | Polysaccharides de synthese, procede pour leur preparation et compositions pharmaceutiques le contenant |
| GB2335490B (en) * | 1998-03-20 | 2003-05-14 | Ortho Clinical Diagnostics | An assay surface that permits an analyte releasiing step |
| WO2000006608A1 (en) | 1998-07-31 | 2000-02-10 | Seikagaku Corporation | Novel glycosaminoglycan and drug compositions containing the same |
| FR2814463B1 (fr) * | 2000-09-22 | 2002-11-15 | Sanofi Synthelabo | Nouveaux polysaccharides a activite antithrombotique comprenant au moins une liaison covalente avec la biotine ou un derive de la biotine |
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2000
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2001
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