SK15699A3 - Modified oligosaccharides, process for their preparation and pharmaceutical composition containing them - Google Patents

Modified oligosaccharides, process for their preparation and pharmaceutical composition containing them Download PDF

Info

Publication number: SK15699A3
Authority: SK; Slovakia
Prior art keywords: carbon atoms; group; alkyl; aryl; cycloalkyl
Prior art date: 1996-08-08

Application number

SK156-99A

Other languages

English (en)

Slovak (sk)

Inventor

Gebhard Thoma

Rolf Banteli

Willy Kinzy

Original Assignee

Novartis Ag

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.)

1996-08-08

Filing date

1997-08-06

Publication date

1999-07-12

1997-08-06 Application filed by Novartis Ag filed Critical Novartis Ag

1999-07-12 Publication of SK15699A3 publication Critical patent/SK15699A3/sk

Links

238000002360 preparation method Methods 0.000 title claims description 34
238000000034 method Methods 0.000 title claims description 20
230000008569 process Effects 0.000 title claims description 8
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
229920001542 oligosaccharide Polymers 0.000 title 1
150000002482 oligosaccharides Chemical class 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims description 417
150000001875 compounds Chemical class 0.000 claims description 172
125000000217 alkyl group Chemical group 0.000 claims description 129
125000000753 cycloalkyl group Chemical group 0.000 claims description 92
125000003118 aryl group Chemical group 0.000 claims description 91
-1 sulfonyl Chemical group 0.000 claims description 88
125000001072 heteroaryl group Chemical group 0.000 claims description 75
125000003710 aryl alkyl group Chemical group 0.000 claims description 73
125000001424 substituent group Chemical group 0.000 claims description 67
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 64
229910052739 hydrogen Inorganic materials 0.000 claims description 64
125000004475 heteroaralkyl group Chemical group 0.000 claims description 61
239000001257 hydrogen Substances 0.000 claims description 48
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 42
125000003342 alkenyl group Chemical group 0.000 claims description 39
125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
229910052799 carbon Inorganic materials 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
125000004404 heteroalkyl group Chemical group 0.000 claims description 14
150000003839 salts Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 12
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 11
125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 9
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 9
125000004104 aryloxy group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
229930182830 galactose Natural products 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 5
150000008267 fucoses Chemical class 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 4
239000000539 dimer Substances 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
239000013638 trimer Substances 0.000 claims description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 abstract description 3
OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 abstract description 3
MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 abstract description 3
239000000178 monomer Substances 0.000 abstract description 3
229950006780 n-acetylglucosamine Drugs 0.000 abstract description 3
NIGUVXFURDGQKZ-UQTBNESHSA-N alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc Chemical class O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@]3(O[C@H]([C@H](NC(C)=O)[C@@H](O)C3)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O NIGUVXFURDGQKZ-UQTBNESHSA-N 0.000 abstract description 2
CERZMXAJYMMUDR-QBTAGHCHSA-N 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid Chemical group N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO CERZMXAJYMMUDR-QBTAGHCHSA-N 0.000 abstract 1
XBSNXOHQOTUENA-KRAHZTDDSA-N alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->3)-[alpha-L-Fuc-(1->4)]-D-GlcNAc Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@]3(O[C@H]([C@H](NC(C)=O)[C@@H](O)C3)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](NC(C)=O)C(O)O[C@@H]1CO XBSNXOHQOTUENA-KRAHZTDDSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 65
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
239000011734 sodium Substances 0.000 description 39
239000000203 mixture Substances 0.000 description 38
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
125000006239 protecting group Chemical group 0.000 description 32
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 28
239000002904 solvent Substances 0.000 description 28
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
150000002431 hydrogen Chemical group 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
239000000460 chlorine Substances 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
238000010265 fast atom bombardment Methods 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
238000005481 NMR spectroscopy Methods 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
238000003818 flash chromatography Methods 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
108010001515 Galectin 4 Proteins 0.000 description 13
102100039556 Galectin-4 Human genes 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
229910052786 argon Inorganic materials 0.000 description 13
229910052700 potassium Inorganic materials 0.000 description 13
230000008878 coupling Effects 0.000 description 12
238000010168 coupling process Methods 0.000 description 12
238000005859 coupling reaction Methods 0.000 description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
102100039558 Galectin-3 Human genes 0.000 description 11
XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
239000000377 silicon dioxide Substances 0.000 description 11
108010001517 Galectin 3 Proteins 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
239000006260 foam Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
125000002947 alkylene group Chemical group 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
150000002016 disaccharides Chemical class 0.000 description 9
239000012038 nucleophile Substances 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
238000004108 freeze drying Methods 0.000 description 8
150000002256 galaktoses Chemical class 0.000 description 8
238000002523 gelfiltration Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
239000012300 argon atmosphere Substances 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
210000000265 leukocyte Anatomy 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
229910052708 sodium Inorganic materials 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
150000004043 trisaccharides Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical group C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229910001415 sodium ion Inorganic materials 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
150000008481 L-fucoses Chemical class 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000005342 ion exchange Methods 0.000 description 5
125000001624 naphthyl group Chemical group 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000004366 reverse phase liquid chromatography Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
102000015689 E-Selectin Human genes 0.000 description 4
108010024212 E-Selectin Proteins 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
125000004450 alkenylene group Chemical group 0.000 description 4
125000001118 alkylidene group Chemical group 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
150000007942 carboxylates Chemical group 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 4
238000010828 elution Methods 0.000 description 4
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
235000000346 sugar Nutrition 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 3
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 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 3
101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 3
102000003800 Selectins Human genes 0.000 description 3
108090000184 Selectins Proteins 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
125000003158 alcohol group Chemical group 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
230000008614 cellular interaction Effects 0.000 description 3
XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
150000002301 glucosamine derivatives Chemical class 0.000 description 3
150000002337 glycosamines Chemical class 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
230000003993 interaction Effects 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
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PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000008458 response to injury Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003333 secondary alcohols Chemical group 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229960002930 sirolimus Drugs 0.000 description 1
QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
DVWOYOSIEJRHKW-UIRZNSHLSA-M sodium (2S)-2-[[(2S)-2-[[(4,4-difluorocyclohexyl)-phenylmethoxy]carbonylamino]-4-methylpentanoyl]amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonate Chemical compound FC1(CCC(CC1)C(OC(=O)N[C@H](C(=O)N[C@H](C(S(=O)(=O)[O-])O)C[C@H]1C(NCC1)=O)CC(C)C)C1=CC=CC=C1)F.[Na+] DVWOYOSIEJRHKW-UIRZNSHLSA-M 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003527 tetrahydropyrans Chemical class 0.000 description 1
125000005710 tetrahydropyranylene group Chemical group 0.000 description 1
150000004044 tetrasaccharides Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
229940035024 thioglycerol Drugs 0.000 description 1
150000003569 thioglycosides Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000002948 undecyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7008—Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Rheumatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

SK156-99A 1996-08-08 1997-08-06 Modified oligosaccharides, process for their preparation and pharmaceutical composition containing them SK15699A3 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
EP96810526		1996-08-08
EP96810527		1996-08-08
EP96810636		1996-09-26
PCT/EP1997/004279 WO1998006730A1 (en)	1996-08-08	1997-08-06	Modified oligosaccharides

Publications (1)

Publication Number	Publication Date
SK15699A3 true SK15699A3 (en)	1999-07-12

Family

ID=27237868

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK156-99A SK15699A3 (en)	1996-08-08	1997-08-06	Modified oligosaccharides, process for their preparation and pharmaceutical composition containing them

Country Status (19)

Country	Link
EP (1)	EP0920437A1 (cs)
JP (1)	JP2000516224A (cs)
KR (1)	KR20000029862A (cs)
CN (1)	CN1227563A (cs)
AR (1)	AR008283A1 (cs)
AU (1)	AU720381B2 (cs)
BR (1)	BR9711117A (cs)
CA (1)	CA2260854A1 (cs)
CO (1)	CO4900075A1 (cs)
CZ (1)	CZ39099A3 (cs)
ID (1)	ID18010A (cs)
IL (1)	IL127908A0 (cs)
NO (1)	NO990497L (cs)
NZ (1)	NZ334048A (cs)
PE (1)	PE99298A1 (cs)
PL (1)	PL331286A1 (cs)
SK (1)	SK15699A3 (cs)
TR (1)	TR199900245T2 (cs)
WO (1)	WO1998006730A1 (cs)

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US5888984A (en) *	1994-05-12	1999-03-30	Dermal Research Laboratories, Inc.	Pharmaceutical composition of complex carbohydrates and essential oils and methods of using the same
EP1165097B1 (en)	1999-02-01	2007-05-02	Dermal Research Laboratories, Inc.	A pharmaceutical composition of complex carbohydrates and their use
US7879824B2 (en)	2001-07-31	2011-02-01	Dermal Research Laboratories, Inc.	Methods of preventing or treating diseases and conditions using complex carbohydrates
JP2006502986A (ja) *	2002-07-03	2006-01-26	グリコミメティクス，インコーポレイテッド	新脈管形成に関与する医学的状態の診断および治療のための組成物および方法
JP4603888B2 (ja)	2002-10-11	2010-12-22	アステラスファルマユーロープベスローテンフェンノートシャップ	Ｐ−セレクチンに対する親和性を有しグルコースをベースとする化合物
WO2005054264A2 (en) *	2003-11-19	2005-06-16	Glycomimetics, Inc.	Glycomimetic antagonists for both e- and p-selectins
EP1763533B1 (en)	2003-11-19	2008-01-09	GlycoMimetics, Inc.	Specific antagonist for both e- and p-selectins
US20090036386A1 (en) *	2005-05-25	2009-02-05	Glycomimetics, Inc	Heterobifunctional compounds for selectin inhibition
CN101291946B (zh)	2005-08-09	2011-06-29	糖模拟物有限公司	对来自假单胞菌的pa-il凝集素、pa-iil凝集素或其两者的糖模拟物抑制剂
PL2264043T3 (pl)	2005-09-02	2018-04-30	Glycomimetics, Inc.	Heterobifunkcyjne inhibitory pan-selektyny
AU2008216794A1 (en) *	2007-02-09	2008-08-21	Glycomimetics, Inc.	Methods of use of glycomimetics with replacements for hexoses and N-acetyl hexosamines
WO2009073911A1 (en)	2007-12-10	2009-06-18	Mater Medical Research Institute	Treatment and prophylaxis
WO2009126556A1 (en)	2008-04-08	2009-10-15	Glycomimetics, Inc.	Pan-selectin inhibitor with enhanced pharmacokinetic activity
US8921328B2 (en)	2010-09-14	2014-12-30	Glycomimetics, Inc.	E-selectin antagonists
KR102055958B1 (ko)	2011-12-22	2019-12-13	글리코미메틱스, 인크.	E-셀렉틴 길항제 화합물, 조성물, 및 이용 방법
US9867841B2 (en)	2012-12-07	2018-01-16	Glycomimetics, Inc.	Compounds, compositions and methods using E-selectin antagonists for mobilization of hematopoietic cells
JP6689854B2 (ja)	2014-12-03	2020-04-28	グリコミメティクス，インコーポレイテッド	Ｅ−セレクチンおよびｃｘｃｒ４ケモカイン受容体のヘテロ二官能性阻害剤
JP2019502727A (ja)	2016-01-22	2019-01-31	グリコミメティクス，インコーポレイテッド	Ｐａ−ｉｌおよび／またはｐａ−ｉｉｌレクチンの糖模倣体阻害剤
WO2017151708A1 (en)	2016-03-02	2017-09-08	Glycomimetics, Inc.	Methods for the treatment and/or prevention of cardiovescular disease by inhibition of e-selectin
US11433086B2 (en)	2016-08-08	2022-09-06	Glycomimetics, Inc.	Combination of T-cell checkpoint inhibitors with inhibitors of e-selectin or CXCR4, or with heterobifunctional inhibitors of both E-selectin and CXCR4
AU2017341065B2 (en)	2016-10-07	2023-04-06	Crescent Biopharma, Inc.	Highly potent multimeric E-selectin antagonists
EP3596096A1 (en)	2017-03-15	2020-01-22	GlycoMimetics, Inc.	Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists
JP7275131B2 (ja)	2017-11-30	2023-05-17	グリコミメティクス，インコーポレイテッド	骨髄浸潤リンパ球を動員する方法、およびその使用
KR20200104889A (ko)	2017-12-29	2020-09-04	글리코미메틱스, 인크.	E-셀렉틴 및 갈렉틴-3의 이종이기능성 억제제
CN108299525B (zh) *	2018-01-05	2021-03-26	佛山科学技术学院	路易斯寡糖-x的合成方法
KR20200128025A (ko)	2018-03-05	2020-11-11	글리코미메틱스, 인크.	급성 골수성 백혈병 및 관련 병태의 치료 방법
US11845771B2 (en)	2018-12-27	2023-12-19	Glycomimetics, Inc.	Heterobifunctional inhibitors of E-selectin and galectin-3
CN109762032A (zh) *	2019-01-16	2019-05-17	天津科技大学	一种磺酸化路易斯x三糖及其合成方法和应用

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CA2157489A1 (en) *	1993-03-04	1994-09-15	Masaaki Numata	Lewis-associated compound, process for producing the same, and anti-inflammatory
CZ298895A3 (en) *	1993-05-14	1996-04-17	Cytel Corp	Compound analogous to sialyl lex, pharmaceutical composition containing thereof and process for preparing lactosammonium salt
MX9704893A (es) *	1994-12-28	1997-10-31	Sumitomo Pharma	Derivados de lewis x y procesos para producir los mismos.

1997
- 1997-08-06 IL IL12790897A patent/IL127908A0/xx unknown
- 1997-08-06 NZ NZ334048A patent/NZ334048A/xx unknown
- 1997-08-06 KR KR1019997001025A patent/KR20000029862A/ko not_active Withdrawn
- 1997-08-06 CN CN97197077A patent/CN1227563A/zh active Pending
- 1997-08-06 TR TR1999/00245T patent/TR199900245T2/xx unknown
- 1997-08-06 CZ CZ99390A patent/CZ39099A3/cs unknown
- 1997-08-06 CA CA002260854A patent/CA2260854A1/en not_active Abandoned
- 1997-08-06 JP JP10509358A patent/JP2000516224A/ja active Pending
- 1997-08-06 PL PL97331286A patent/PL331286A1/xx unknown
- 1997-08-06 AU AU43788/97A patent/AU720381B2/en not_active Ceased
- 1997-08-06 AR ARP970103580A patent/AR008283A1/es unknown
- 1997-08-06 EP EP97941916A patent/EP0920437A1/en not_active Withdrawn
- 1997-08-06 WO PCT/EP1997/004279 patent/WO1998006730A1/en not_active Ceased
- 1997-08-06 BR BR9711117-1A patent/BR9711117A/pt not_active Application Discontinuation
- 1997-08-06 SK SK156-99A patent/SK15699A3/sk unknown
- 1997-08-07 PE PE1997000688A patent/PE99298A1/es not_active Application Discontinuation
- 1997-08-08 CO CO97045596A patent/CO4900075A1/es unknown
- 1997-08-08 ID IDP972766A patent/ID18010A/id unknown
1999
- 1999-02-03 NO NO990497A patent/NO990497L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CZ39099A3 (cs)	1999-05-12
AR008283A1 (es)	1999-12-29
WO1998006730A1 (en)	1998-02-19
CN1227563A (zh)	1999-09-01
CA2260854A1 (en)	1998-02-19
NZ334048A (en)	2000-05-26
TR199900245T2 (xx)	1999-05-21
CO4900075A1 (es)	2000-03-27
PL331286A1 (en)	1999-07-05
JP2000516224A (ja)	2000-12-05
NO990497L (no)	1999-03-24
IL127908A0 (en)	1999-11-30
ID18010A (id)	1998-02-19
AU4378897A (en)	1998-03-06
AU720381B2 (en)	2000-06-01
KR20000029862A (ko)	2000-05-25
EP0920437A1 (en)	1999-06-09
NO990497D0 (no)	1999-02-03
BR9711117A (pt)	1999-09-08
PE99298A1 (es)	1999-01-21

Publication	Publication Date	Title
SK15699A3 (en)	1999-07-12	Modified oligosaccharides, process for their preparation and pharmaceutical composition containing them
US11919921B2 (en)	2024-03-05	Galactoside inhibitor of galectins
JP3915116B2 (ja)	2007-05-16	新規ピラゾール誘導体及びそれらを含有する糖尿病治療薬
JP4553488B2 (ja)	2010-09-29	カルボキシメチルガラクトース誘導体
SK177897A3 (en)	1998-08-05	Diglycosylated 1,2-diols as mimetics of sialyl-lewis x and sialyl-lewis a
EP0912613B1 (fr)	2002-09-25	Polysaccharides synthetiques, procede pour leur preparation et compositions pharmaceutiques les contenant
JPS61148193A (ja)	1986-07-05	腫瘍治療剤
EP0801071A1 (en)	1997-10-15	Lewis x derivative and process for producing the same
JPH0899989A (ja)	1996-04-16	新規糖脂質誘導体およびその製造用中間体
EP3819302B1 (en)	2022-10-19	Fucosylated chondroitin sulfate oligosaccharide, preparation method therefor, composition thereof and use thereof
JPH05194602A (ja)	1993-08-03	硫酸化グリコサミノグリカノイド誘導体
EP3492484A1 (en)	2019-06-05	Novel galactoside inhibitor of galectins
CA2204204C (en)	2006-02-28	Carbohydrate derivatives
CA2442979C (en)	2010-02-16	Process for the preparation of 2'-halo-.beta.-l-arabinofuranosyl nucleosides
Hashihayata et al.	2003	Convergent total syntheses of oligosaccharides by one-pot sequential stereoselective glycosylations
JPH09183789A (ja)	1997-07-15	新規な硫酸化及び燐酸化糖誘導体、その製法及び用途
EP0643718A1 (en)	1995-03-22	IMMUNOSUPPRESSIVE AND TOLEROGENIC MODIFIED LEWIS?C AND LacNAc COMPOUNDS
US20150105543A1 (en)	2015-04-16	Synthesis
MXPA99001287A (en)	1999-06-01	Modified oligosaccharides
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