DK174348B1 - Pentasaccharider, tetrasaccharider og mellemprodukter i form af pentasaccharider, tetrasaccharider og disaccharider til fremstilling af pentasaccharider, samt fremgangsmåde til fremstilling af pentasaccharider - Google Patents

Pentasaccharider, tetrasaccharider og mellemprodukter i form af pentasaccharider, tetrasaccharider og disaccharider til fremstilling af pentasaccharider, samt fremgangsmåde til fremstilling af pentasaccharider Download PDF

Info

Publication number: DK174348B1
Authority: DK; Denmark
Prior art keywords: benzyl; acetyl; hydrogen; groups; alkyl
Prior art date: 1982-01-15

Application number

DK14383A

Other languages

Danish (da)

English (en)

Other versions

DK14383A (da

DK14383D0 (da

Inventor

Maurice Petitou

Jean-Claude Lormeau

Jean Choay

Jean-Claude Jacquinet

Pierre Sinay

Mahmoud Nassr

Original Assignee

Sanofi Synthelabo

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.)

1982-01-15

Filing date

1983-01-14

Publication date

2002-12-23

1982-01-15 Priority claimed from FR8200621A external-priority patent/FR2519987A1/fr

1982-02-01 Priority claimed from FR8201575A external-priority patent/FR2520744A1/fr

1982-02-16 Priority claimed from FR8202526A external-priority patent/FR2521566A1/fr

1982-05-28 Priority claimed from FR8209392A external-priority patent/FR2527614A1/fr

1982-06-22 Priority claimed from FR8210891A external-priority patent/FR2528853A1/fr

1982-06-22 Priority claimed from FR8210892A external-priority patent/FR2528854A1/fr

1982-07-02 Priority claimed from FR8211679A external-priority patent/FR2529557A1/fr

1982-08-06 Priority claimed from FR8213804A external-priority patent/FR2531436A1/fr

1982-09-20 Priority claimed from FR8215804A external-priority patent/FR2533220A1/fr

1982-09-20 Priority claimed from FR8215803A external-priority patent/FR2533219A1/fr

1982-10-27 Priority claimed from FR8218003A external-priority patent/FR2535324A1/fr

1983-01-14 Publication of DK14383D0 publication Critical patent/DK14383D0/da

1983-01-14 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

1983-07-16 Publication of DK14383A publication Critical patent/DK14383A/da

2002-12-23 Publication of DK174348B1 publication Critical patent/DK174348B1/da

2002-12-23 Application granted granted Critical

Links

150000002016 disaccharides Chemical class 0.000 title claims description 33
238000000034 method Methods 0.000 title claims description 31
239000000543 intermediate Substances 0.000 title claims description 30
230000008569 process Effects 0.000 title claims description 20
150000004044 tetrasaccharides Chemical class 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title description 27
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 77
150000001875 compounds Chemical class 0.000 claims description 76
229910052739 hydrogen Inorganic materials 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 66
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 58
238000006243 chemical reaction Methods 0.000 claims description 50
125000000217 alkyl group Chemical group 0.000 claims description 39
-1 monochloroacetyl Chemical group 0.000 claims description 36
239000002904 solvent Substances 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 29
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 16
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 14
150000002772 monosaccharides Chemical class 0.000 claims description 13
238000005670 sulfation reaction Methods 0.000 claims description 13
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 11
230000019635 sulfation Effects 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000001340 alkali metals Chemical class 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 9
238000006482 condensation reaction Methods 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
230000001180 sulfating effect Effects 0.000 claims description 9
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
230000000903 blocking effect Effects 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 17
125000005843 halogen group Chemical group 0.000 claims 7
BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 claims 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
239000003513 alkali Substances 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 134
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 75
239000000203 mixture Substances 0.000 description 68
239000000243 solution Substances 0.000 description 67
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
230000015572 biosynthetic process Effects 0.000 description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
238000001704 evaporation Methods 0.000 description 31
238000003786 synthesis reaction Methods 0.000 description 31
230000008020 evaporation Effects 0.000 description 30
150000002338 glycosides Chemical group 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
238000005755 formation reaction Methods 0.000 description 22
239000006188 syrup Substances 0.000 description 22
235000020357 syrup Nutrition 0.000 description 22
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 21
239000007795 chemical reaction product Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 19
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
125000006239 protecting group Chemical group 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
238000011282 treatment Methods 0.000 description 17
238000010828 elution Methods 0.000 description 16
125000001424 substituent group Chemical group 0.000 description 15
238000004809 thin layer chromatography Methods 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000000921 elemental analysis Methods 0.000 description 14
125000000524 functional group Chemical group 0.000 description 14
229930182470 glycoside Natural products 0.000 description 14
150000002482 oligosaccharides Chemical class 0.000 description 14
239000002253 acid Substances 0.000 description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
229920001542 oligosaccharide Polymers 0.000 description 13
239000007858 starting material Substances 0.000 description 13
238000005481 NMR spectroscopy Methods 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
238000001816 cooling Methods 0.000 description 11
238000002329 infrared spectrum Methods 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
239000005457 ice water Substances 0.000 description 10
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230000007935 neutral effect Effects 0.000 description 10
239000012071 phase Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
230000000694 effects Effects 0.000 description 8
AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical group O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 description 8
235000000346 sugar Nutrition 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
150000001721 carbon Chemical group 0.000 description 7
229960002897 heparin Drugs 0.000 description 7
150000002905 orthoesters Chemical class 0.000 description 7
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UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
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HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical group 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 6
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239000012300 argon atmosphere Substances 0.000 description 6
238000005893 bromination reaction Methods 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
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235000017557 sodium bicarbonate Nutrition 0.000 description 6
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UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
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LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 5
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239000002609 medium Substances 0.000 description 5
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YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
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238000007920 subcutaneous administration Methods 0.000 description 4
229910052713 technetium Inorganic materials 0.000 description 4
GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
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125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
QQZMDXUEROTLLD-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QQZMDXUEROTLLD-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
206010043554 thrombocytopenia Diseases 0.000 description 1
229960000103 thrombolytic agent Drugs 0.000 description 1
201000005665 thrombophilia Diseases 0.000 description 1
239000010936 titanium Substances 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
238000012546 transfer Methods 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
POSZUTFLHGNLHX-KSBRXOFISA-N tris maleate Chemical compound OCC(N)(CO)CO.OCC(N)(CO)CO.OC(=O)\C=C/C(O)=O POSZUTFLHGNLHX-KSBRXOFISA-N 0.000 description 1
229960005356 urokinase Drugs 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Landscapes

Polysaccharides And Polysaccharide Derivatives (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

DK14383A 1982-01-15 1983-01-14 Pentasaccharider, tetrasaccharider og mellemprodukter i form af pentasaccharider, tetrasaccharider og disaccharider til fremstilling af pentasaccharider, samt fremgangsmåde til fremstilling af pentasaccharider DK174348B1 (da)

Applications Claiming Priority (22)

Application Number	Priority Date	Filing Date	Title
FR8200621		1982-01-15
FR8200621A FR2519987A1 (fr)	1982-01-15	1982-01-15	Trisaccharides a structures d-glucosamine, acide d-glucuronique, d-glucosamine et leur preparation
FR8201575		1982-02-01
FR8201575A FR2520744A1 (fr)	1982-02-01	1982-02-01	Nouveaux derives d'osides et leur preparation
FR8202526A FR2521566A1 (fr)	1982-02-16	1982-02-16	Nouveaux tetrasaccharides et leur preparation
FR8202526		1982-02-16
FR8209392		1982-05-28
FR8209392A FR2527614A1 (fr)	1982-05-28	1982-05-28	Nouveaux derives de disaccharides formes de motifs a structure respectivement glucosamine et acide uronique et leur preparation
FR8210892A FR2528854A1 (fr)	1982-06-22	1982-06-22	Nouveaux derives de tetrasaccharides et leur preparation
FR8210892		1982-06-22
FR8210891A FR2528853A1 (fr)	1982-06-22	1982-06-22	Nouveaux trisaccharides a structure d-glucosamine, acide l-iduronique, d-glucosamine et leur preparation
FR8210891		1982-06-22
FR8211679A FR2529557A1 (fr)	1982-07-02	1982-07-02	Nouveaux disaccharides contenant un motif a-l-idopyranose, et leur preparation
FR8211679		1982-07-02
FR8213804		1982-08-06
FR8213804A FR2531436A1 (fr)	1982-08-06	1982-08-06	Pentasaccharides substitues possedant des proprietes biologiques, leur preparation et leurs applications en tant que medicaments
FR8215804A FR2533220A1 (fr)	1982-09-20	1982-09-20	Nouveaux disaccharides formes de motifs a structure acide d-glucuronique et d-glucosamine et procede pour leur preparation
FR8215803		1982-09-20
FR8215804		1982-09-20
FR8215803A FR2533219A1 (fr)	1982-09-20	1982-09-20	Nouveaux disaccharides formes de motifs a structure d-glucosamine et acide l-iduronique et procede pour leur preparation
FR8218003		1982-10-27
FR8218003A FR2535324A1 (fr)	1982-10-27	1982-10-27	Station perfectionnee pour l'epuration d'eaux usees

Publications (3)

Publication Number	Publication Date
DK14383D0 DK14383D0 (da)	1983-01-14
DK14383A DK14383A (da)	1983-07-16
DK174348B1 true DK174348B1 (da)	2002-12-23

Family

ID=27581614

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK14383A DK174348B1 (da)	1982-01-15	1983-01-14	Pentasaccharider, tetrasaccharider og mellemprodukter i form af pentasaccharider, tetrasaccharider og disaccharider til fremstilling af pentasaccharider, samt fremgangsmåde til fremstilling af pentasaccharider

Country Status (5)

Country	Link
JP (1)	JP2510454B2 (de)
AT (1)	ATE33496T1 (de)
CA (1)	CA1265132A (de)
DE (2)	DE10299025I2 (de)
DK (1)	DK174348B1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10072039B2 (en)	2013-07-25	2018-09-11	Scinopharm Taiwan, Ltd.	Process for the production of Fondaparinux sodium
EP3024840B1 (de) *	2013-07-25	2019-10-02	ScinoPharm Taiwan, Ltd.	Verfahren zur herstellung von fondaparinux-natrium

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1136620A (en) *	1979-01-08	1982-11-30	Ulf P.F. Lindahl	Heparin fragments having selective anticoagulation activity
AT377493B (de) *	1979-09-19	1985-03-25	Wiedmer Ernst	Schraubverschluss mit einem garantiering fuer einen behaelter zur anzeige der erstmaligen oeffnung des behaelters
IL61201A (en) *	1979-10-05	1984-09-30	Choay Sa	Oligosaccharides having no more than 8 saccharide moieties,their obtention from heparin and pharmaceutical compositions containing them
FR2504535B1 (fr) *	1981-04-28	1987-08-14	Choay Sa	Disaccharides derives d'un acide uronique et d'une glucosamine et compositions pharmaceutiques les contenant pour le controle de la coagulation sanguine

1983
- 1983-01-13 CA CA000419417A patent/CA1265132A/en not_active Expired
- 1983-01-14 DK DK14383A patent/DK174348B1/da not_active IP Right Cessation
- 1983-01-17 AT AT83400110T patent/ATE33496T1/de active
- 1983-01-17 DE DE2002199025 patent/DE10299025I2/de active Active
- 1983-01-17 DE DE8383400110T patent/DE3376265D1/de not_active Expired
1992
- 1992-04-08 JP JP4115407A patent/JP2510454B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPH05331182A (ja)	1993-12-14
ATE33496T1 (de)	1988-04-15
DE10299025I2 (de)	2002-11-07
JP2510454B2 (ja)	1996-06-26
DE3376265D1 (en)	1988-05-19
DK14383A (da)	1983-07-16
CA1265132A (en)	1990-01-30
DK14383D0 (da)	1983-01-14

Legal Events

Date	Code	Title	Description
2003-02-03	PUP	Patent expired

Publication	Publication Date	Title
DK175970B1 (da)	2005-10-03	Fremgangsmåde til organisk syntese af oligosaccharider indeholdende galactosamin-uronsyre-mönstre, ved fremgangsmåden opnåede oligosaccharider og biologisk anvendelse af sådanne oligosaccharider
US4818816A (en)	1989-04-04	Process for the organic synthesis of oligosaccharides and derivatives thereof
EP0084999B1 (de)	1988-04-13	Verfahren zur Herstellung von organischen Oligosacchariden übereinstimmend mit Fragmenten von natürlichen Muco-Polysacchariden, die erhaltenen Oligosaccharide und ihre biologische Verwendung
Orgueira et al.	2003	Modular synthesis of heparin oligosaccharides
EP2464668B1 (de)	2022-12-07	Verfahren zur herstellung von fondaparinuxnatrium und nützliche zwischenprodukte für seine synthese
Jacquinet et al.	1984	Synthesis of heparin fragments. A chemical synthesis of the trisaccharide O-(2-deoxy-2-sulfamido-3, 6-di-O-sulfo-α-d-glucopyranosyl)-(1→ 4)-O-(2-O-sulfo-α-l-idopyranosyluronic acid)-(1→ 4)-2-deoxy-2-sulfamido-6-O-sulfo-d-glucopyranose heptasodium salt
SU1470196A3 (ru)	1989-03-30	Способ получени 1,4 @ -дисахаридов,состо щих из звеньев структуры @ -Глюкозамина и гликуроновой кислоты
JP2005505565A (ja)	2005-02-24	合成ヘパリン五糖
KR100324583B1 (ko)	2002-11-13	3-데옥시올리고사카라이드,상기화합물을제조하는방법및상기화합물을함유하는약제학적조성물
FR2751334A1 (fr)	1998-01-23	Polysaccharides synthetiques, procede pour leur preparation et compositions pharmaceutiques les contenant
DK174284B1 (da)	2002-11-11	Biologisk aktive tetrasaccharider
Petitou et al.	1991	A new, highly potent, heparin-like pentasaccharide fragment containing a glucose residue instead of a glucosamine
Suda et al.	1996	Synthesis and biological activity of a model disaccharide containing a key unit in heparin for binding to platelets
Duchaussoy et al.	1999	Assessment through chemical synthesis of the size of the heparin sequence involved in thrombin inhibition
Petitou et al.	1998	Introducing a C-interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties
JPS58170797A (ja)	1983-10-07	オリゴサッカライド及びその誘導体の製造方法
CA1265132A (en)	1990-01-30	Process for the organic synthesis of oligosaccharides and derivatives thereof
Sheppard	2024	Synthetic sulfated saccharides in cell signalling
Trouilleux et al.	2019	Kilogram‐scale Production of Synthetic Heparin Analogs: Some Chemical Considerations
Kawatkar	2004	Heparan sulfate synthesis: challenges and prospects
IE54472B1 (en)	1989-10-25	Process for the organic synthesis of oligosaccharides corresponding to fragments of natural mucopolysaccharides, oligosaccharides therby obtained and their biological applications
Wongsrisupphakul	2018	Glycosylation of 2-nitro-1-thioglycoside as glycosyl donor
Joshi	2018	Chemical synthesis of 3-o-sulfated heparan sulfate oligosaccharides as diagnostic biomarkers and standards for exploring protein-carbohydrate interactions
Desoky	2010	Synthesis of Sulfated Carbohydrates Using Sulfuryl Imidazolium Salts
FR2531436A1 (fr)	1984-02-10	Pentasaccharides substitues possedant des proprietes biologiques, leur preparation et leurs applications en tant que medicaments