CA2256504A1 - Novel anticoagulant glycosides and pharmaceutical compositions thereof - Google Patents

Novel anticoagulant glycosides and pharmaceutical compositions thereof Download PDF

Info

Publication number: CA2256504A1
Authority: CA; Canada
Prior art keywords: group; formula; azido; deoxy; dithio
Prior art date: 1996-06-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002256504A

Other languages

English (en)

French (fr)

Inventor

Sandor Boros

Imre Moravcsik

Eva Kovacsne Bozo

Janos Kuszmann

Gabriella Szabo

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Richter Gedeon Vegyeszeti Gyar Nyrt

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-06-25

Filing date

1997-06-23

Publication date

1997-12-31

1997-06-23 Application filed by Individual filed Critical Individual

1997-12-31 Publication of CA2256504A1 publication Critical patent/CA2256504A1/en

Status Abandoned legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
239000003146 anticoagulant agent Substances 0.000 title claims description 6
229930182470 glycoside Natural products 0.000 title description 30
150000002338 glycosides Chemical class 0.000 title description 29
229940127219 anticoagulant drug Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 147
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 67
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 58
-1 hydroxy, azido, amino Chemical group 0.000 claims abstract description 52
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 50
239000001257 hydrogen Substances 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 31
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 27
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 20
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 18
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 4
150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
150000007524 organic acids Chemical class 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims description 64
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 37
150000002431 hydrogen Chemical class 0.000 claims description 12
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000000463 material Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000003814 drug Substances 0.000 claims 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract description 4
230000001225 therapeutic effect Effects 0.000 abstract description 4
230000002429 anti-coagulating effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 180
239000000243 solution Substances 0.000 description 89
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 78
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
239000000203 mixture Substances 0.000 description 69
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 63
125000003118 aryl group Chemical group 0.000 description 59
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 50
238000005481 NMR spectroscopy Methods 0.000 description 49
238000004440 column chromatography Methods 0.000 description 43
239000011541 reaction mixture Substances 0.000 description 41
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
238000000034 method Methods 0.000 description 33
125000001841 imino group Chemical group [H]N=* 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 24
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 24
MVPUXVBBHWUOFS-UHFFFAOYSA-N 4-sulfanylbenzonitrile Chemical compound SC1=CC=C(C#N)C=C1 MVPUXVBBHWUOFS-UHFFFAOYSA-N 0.000 description 23
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
229910052799 carbon Inorganic materials 0.000 description 19
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 17
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 16
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 16
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
239000011347 resin Substances 0.000 description 14
229920005989 resin Polymers 0.000 description 14
229920001467 poly(styrenesulfonates) Polymers 0.000 description 13
239000007858 starting material Substances 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 11
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 11
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
229910000042 hydrogen bromide Inorganic materials 0.000 description 8
229910000037 hydrogen sulfide Inorganic materials 0.000 description 8
239000000047 product Substances 0.000 description 8
125000003944 tolyl group Chemical group 0.000 description 8
125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 7
239000000010 aprotic solvent Substances 0.000 description 7
125000001246 bromo group Chemical group Br* 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
238000010992 reflux Methods 0.000 description 7
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
239000005695 Ammonium acetate Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
239000012359 Methanesulfonyl chloride Substances 0.000 description 6
235000019257 ammonium acetate Nutrition 0.000 description 6
229940043376 ammonium acetate Drugs 0.000 description 6
230000002785 anti-thrombosis Effects 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
125000004185 ester group Chemical group 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
125000002346 iodo group Chemical group I* 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
LKFCPWBGBPJDRC-UHFFFAOYSA-M potassium;thiobenzate Chemical compound [K+].[O-]C(=S)C1=CC=CC=C1 LKFCPWBGBPJDRC-UHFFFAOYSA-M 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 4
150000001720 carbohydrates Chemical group 0.000 description 4
XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
230000014508 negative regulation of coagulation Effects 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
150000002971 pentose derivatives Chemical class 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 4
UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 3
AOYOBWSGCQMROU-UHFFFAOYSA-N 2-sulfanylbenzonitrile Chemical compound SC1=CC=CC=C1C#N AOYOBWSGCQMROU-UHFFFAOYSA-N 0.000 description 3
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000003379 elimination 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
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000012022 methylating agents‎ Substances 0.000 description 3
UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 3
230000003472 neutralizing effect Effects 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 3
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
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
QZNHVMNXXQCWLU-UHFFFAOYSA-N 4-nitrobenzenethiol;4-sulfanylbenzonitrile Chemical compound SC1=CC=C(C#N)C=C1.[O-][N+](=O)C1=CC=C(S)C=C1 QZNHVMNXXQCWLU-UHFFFAOYSA-N 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
241000700159 Rattus Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
YFHNDHXQDJQEEE-UHFFFAOYSA-N acetic acid;hydrazine Chemical compound NN.CC(O)=O YFHNDHXQDJQEEE-UHFFFAOYSA-N 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
229960004217 benzyl alcohol Drugs 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
229910000011 cadmium carbonate Inorganic materials 0.000 description 2
GKDXQAKPHKQZSC-UHFFFAOYSA-L cadmium(2+);carbonate Chemical compound [Cd+2].[O-]C([O-])=O GKDXQAKPHKQZSC-UHFFFAOYSA-L 0.000 description 2
150000001719 carbohydrate derivatives Chemical class 0.000 description 2
229940068911 chloride hexahydrate Drugs 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
230000006196 deacetylation Effects 0.000 description 2
238000003381 deacetylation reaction Methods 0.000 description 2
150000004252 dithioacetals Chemical class 0.000 description 2
230000008030 elimination Effects 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
VOAPTKOANCCNFV-UHFFFAOYSA-N hexahydrate;hydrochloride Chemical compound O.O.O.O.O.O.Cl VOAPTKOANCCNFV-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
238000003328 mesylation reaction Methods 0.000 description 2
125000005905 mesyloxy group Chemical group 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
238000009738 saturating Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 2
229940071536 silver acetate Drugs 0.000 description 2
229940096017 silver fluoride Drugs 0.000 description 2
REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000005691 triesters Chemical class 0.000 description 2
IJJLRUSZMLMXCN-SLPGGIOYSA-N (2r,3r,4s,5r)-2,3,4,6-tetrahydroxy-5-sulfanylhexanal Chemical compound OC[C@@H](S)[C@@H](O)[C@H](O)[C@@H](O)C=O IJJLRUSZMLMXCN-SLPGGIOYSA-N 0.000 description 1
ABXYOVCSAGTJAC-JGWLITMVSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=S ABXYOVCSAGTJAC-JGWLITMVSA-N 0.000 description 1
QWVJFKXOINHVGD-IOVATXLUSA-N (3r,4s,5s)-thiane-2,3,4,5-tetrol Chemical class O[C@@H]1CSC(O)[C@H](O)[C@H]1O QWVJFKXOINHVGD-IOVATXLUSA-N 0.000 description 1
XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
241001465754 Metazoa Species 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
229910004679 ONO2 Inorganic materials 0.000 description 1
229930182475 S-glycoside Natural products 0.000 description 1
ZUWZHGIJTPZRAX-UHFFFAOYSA-N S.NN Chemical compound S.NN ZUWZHGIJTPZRAX-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
108700043492 SprD Proteins 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
206010047249 Venous thrombosis Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 1
WIVZZUMHGBWZRW-VYJXPWFOSA-N [(2r,3s,4s,5r)-4,5,6-triacetyloxy-2-methylthian-3-yl] acetate Chemical compound C[C@H]1SC(OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O WIVZZUMHGBWZRW-VYJXPWFOSA-N 0.000 description 1
ADLJEAHDCMGZSZ-UHFFFAOYSA-N acetic acid;ethyl acetate;pyridine;hydrate Chemical compound O.CC(O)=O.CCOC(C)=O.C1=CC=NC=C1 ADLJEAHDCMGZSZ-UHFFFAOYSA-N 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
150000003569 thioglycosides Chemical class 0.000 description 1
238000002328 two-dimensional heteronuclear correlation spectroscopy Methods 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002256504A 1996-06-25 1997-06-23 Novel anticoagulant glycosides and pharmaceutical compositions thereof Abandoned CA2256504A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
HU9601756A HUP9601756A3 (en)	1996-06-25	1996-06-25	New anticoagulant glycosides and pharmaceutical compositions containing them
HUP9601756		1996-06-25
PCT/HU1997/000031 WO1997049716A1 (en)	1996-06-25	1997-06-23	Novel anticoagulant glycosides and pharmaceutical compositions thereof

Publications (1)

Publication Number	Publication Date
CA2256504A1 true CA2256504A1 (en)	1997-12-31

Family

ID=89994082

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002256504A Abandoned CA2256504A1 (en)	1996-06-25	1997-06-23	Novel anticoagulant glycosides and pharmaceutical compositions thereof

Country Status (9)

Country	Link
EP (1)	EP0907656A1 (de)
JP (1)	JP2000512989A (de)
AU (1)	AU3354797A (de)
CA (1)	CA2256504A1 (de)
CZ (1)	CZ414998A3 (de)
HU (1)	HUP9601756A3 (de)
PL (1)	PL330727A1 (de)
SK (1)	SK175798A3 (de)
WO (1)	WO1997049716A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1043321A1 (de)	1999-03-29	2000-10-11	Nisshin Flour Milling Co., Ltd.	Verfahren zur Herstellung von Tetrahydropyranderivaten
SG10201603288XA (en)	2012-03-28	2016-05-30	Fujifilm Corp	Salt Of 1-(2-Deoxy-2-Fluoro-4-Thio-beta-D-Arabinofuranosyl)Cytosine
KR20170001722A (ko)	2012-08-13	2017-01-04	후지필름 가부시키가이샤	1-(2-데옥시-2-플루오로-4-티오-β-D-아라비노푸라노실)시토신의 합성 중간체, 티오뉴클레오시드의 합성 중간체, 및 그들의 제조법
EP3109245B1 (de)	2014-02-18	2018-01-03	FUJIFILM Corporation	Verfahren zur herstellung eines thiolanskelettartigen glycokonjugats und thiolanskelettartiges glycokonjugat
JP6204223B2 (ja)	2014-02-19	2017-09-27	富士フイルム株式会社	チオピラノース化合物等の製造方法
TWI678373B (zh)	2014-10-31	2019-12-01	日商富士軟片股份有限公司	硫代核苷衍生物或其鹽及醫藥組合物
IL265044B2 (en)	2016-08-31	2025-02-01	Fujifilm Corp	An antitumor preparation containing the substances nab-paclitaxel and 1-(2-deoxy-2-fluoro-4-thio-D-beta-arabinofurnosyl)cytosine, a kit containing these substances and their uses
WO2019146130A1 (ja)	2018-01-29	2019-08-01	富士フイルム株式会社	胆道がん用抗腫瘍剤および胆道がんの処置方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2614893B1 (fr) *	1987-05-04	1989-12-22	Fournier Innovation Synergie	Nouveaux b-d-phenyl-thioxylosides, leur procede de preparation et leur application en therapeutique
IE63544B1 (en) *	1988-10-18	1995-05-17	Fournier Ind & Sante	Novel Beta-d-phenylthioxylosides their method of preparation and their use in therapy
FR2660313B1 (fr) *	1990-04-02	1992-07-03	Fournier Ind & Sante	Nouveau sulfonyl-phenyl-betha-d-thioxylosides, leur procede de preparation et leur utilisation en therapeutique.

1996
- 1996-06-25 HU HU9601756A patent/HUP9601756A3/hu unknown
1997
- 1997-06-23 WO PCT/HU1997/000031 patent/WO1997049716A1/en not_active Ceased
- 1997-06-23 CZ CZ984149A patent/CZ414998A3/cs unknown
- 1997-06-23 JP JP10502570A patent/JP2000512989A/ja active Pending
- 1997-06-23 AU AU33547/97A patent/AU3354797A/en not_active Abandoned
- 1997-06-23 PL PL97330727A patent/PL330727A1/xx unknown
- 1997-06-23 SK SK1757-98A patent/SK175798A3/sk unknown
- 1997-06-23 EP EP97929440A patent/EP0907656A1/de not_active Withdrawn
- 1997-06-23 CA CA002256504A patent/CA2256504A1/en not_active Abandoned

Also Published As

Publication number	Publication date
HUP9601756A2 (en)	1997-12-29
CZ414998A3 (cs)	1999-03-17
JP2000512989A (ja)	2000-10-03
AU3354797A (en)	1998-01-14
EP0907656A1 (de)	1999-04-14
HU9601756D0 (en)	1996-08-28
SK175798A3 (en)	1999-05-07
WO1997049716A1 (en)	1997-12-31
PL330727A1 (en)	1999-05-24
HUP9601756A3 (en)	1999-05-28

Legal Events

Date	Code	Title	Description
2002-06-25	FZDE	Discontinued

Publication	Publication Date	Title
EP1654269B1 (de)	2014-10-15	Neue verbindungen
Mori et al.	1989	A highly stereoselective and practical synthesis of cyclomannohexaose, Cyclo {→ 4)-[α-D-Manp-(1→ 4)-] 5-α-D-Manp-(1→}, a manno isomer of cyclomaltohexaose
US6759523B2 (en)	2004-07-06	Antimicrobial 2-deoxystreptamine compounds
WO1995029682A1 (en)	1995-11-09	BINDING OF E-SELECTIN, P-SELECTIN OR L-SELECTIN TO SIALYL-LEWISx OR SIALYL-LEWIS?a¿
SK3342003A3 (en)	2003-08-05	Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same
US5744597A (en)	1998-04-28	Stereoselective anion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
CA2256504A1 (en)	1997-12-31	Novel anticoagulant glycosides and pharmaceutical compositions thereof
KR930005990B1 (ko)	1993-07-01	β-D-페닐티오크실로시드 화합물과 그의 제조방법
JP2516769B2 (ja)	1996-07-24	新規なアントラサイクリン
US5034517A (en)	1991-07-23	Process for producing 2,6-dideoxy-2-fluoro-L-talopyranose
EP0230013B1 (de)	1992-06-17	Anthracyclinderivate, ihre Verwendung als Antitumorsubstanzen und ihre Herstellung
JP2540400B2 (ja)	1996-10-02	Ｌ−タロピラノシド誘導体の製造方法
Jürs et al.	2005	Alternative approaches towards glycosylated eight-membered ring compounds employing Claisen rearrangement of mono and disaccharide allyl vinyl ether precursors
US6620921B1 (en)	2003-09-16	Glucofuranoses
US20090137793A1 (en)	2009-05-28	Disaccharide compounds
JP2003512473A (ja)	2003-04-02	ハイグロマイシン誘導体
KR100418167B1 (ko)	2004-02-11	항균제로서의 하이그로마이신 ａ 유도체
CA2162186C (en)	1998-12-15	Pradimicin derivatives
US5246961A (en)	1993-09-21	β-d-phenylthioxylosides, and their use as therapeutic agents
KR920000620B1 (ko)	1992-01-17	신규 안트라사이클린 글리코사이드 유도체
EP0912587A1 (de)	1999-05-06	Stereospezifische mannolysierung mit hoher ausbeute
JPH06256377A (ja)	1994-09-13	新規なアンスラサイクリン誘導体
JPH0689041B2 (ja)	1994-11-09	オリゴガラクチュロン酸の製造法
JPH02275894A (ja)	1990-11-09	３―デオキシマイカミノシルタイロノライド化合物
WO1998024792A1 (en)	1998-06-11	Anticoagulant glycosides and pharmaceutical compositions thereof