JP2006506329A5 - - Google Patents
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- JP2006506329A5 JP2006506329A5 JP2004516828A JP2004516828A JP2006506329A5 JP 2006506329 A5 JP2006506329 A5 JP 2006506329A5 JP 2004516828 A JP2004516828 A JP 2004516828A JP 2004516828 A JP2004516828 A JP 2004516828A JP 2006506329 A5 JP2006506329 A5 JP 2006506329A5
- Authority
- JP
- Japan
- Prior art keywords
- pathogen
- receptor
- pharmaceutical composition
- represented
- group
- Prior art date
- 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.)
- Granted
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- 150000002482 oligosaccharides Polymers 0.000 claims description 77
- 241000588724 Escherichia coli Species 0.000 claims description 26
- 229920001542 oligosaccharide Polymers 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 15
- -1 hydroxy fatty acid Chemical class 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 241000894006 Bacteria Species 0.000 claims description 6
- WPIHMWBQRSAMDE-YCZTVTEBSA-N beta-D-galactosyl-(1->4)-beta-D-galactosyl-N-(pentacosanoyl)sphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC WPIHMWBQRSAMDE-YCZTVTEBSA-N 0.000 claims description 5
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 150000002772 monosaccharides Chemical group 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 4
- 230000002416 diarrheagenic effect Effects 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229930182470 glycoside Natural products 0.000 claims description 2
- 150000002338 glycosides Chemical class 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- DXXSRTXAOPBLSG-HQKKTFEGSA-N isoglobotriosylceramide Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(C)=O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@@H](CO)O1 DXXSRTXAOPBLSG-HQKKTFEGSA-N 0.000 claims description 2
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims description 2
- 108020003175 receptors Proteins 0.000 claims 77
- 230000001717 pathogenic effect Effects 0.000 claims 70
- 244000052769 pathogen Species 0.000 claims 69
- 239000008194 pharmaceutical composition Substances 0.000 claims 66
- 235000013350 formula milk Nutrition 0.000 claims 61
- 150000001875 compounds Chemical class 0.000 claims 39
- 230000002401 inhibitory effect Effects 0.000 claims 32
- 238000000034 method Methods 0.000 claims 14
- 206010012735 Diarrhoea Diseases 0.000 claims 10
- 230000000968 intestinal effect Effects 0.000 claims 10
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims 9
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims 8
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims 8
- 229940106189 ceramide Drugs 0.000 claims 8
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims 8
- 208000019836 digestive system infectious disease Diseases 0.000 claims 8
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims 8
- 239000000047 product Substances 0.000 claims 8
- 108010031099 Mannose Receptor Proteins 0.000 claims 7
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical group CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 claims 7
- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims 7
- 108090000623 proteins and genes Proteins 0.000 claims 7
- 102000004169 proteins and genes Human genes 0.000 claims 7
- 108010061514 sialic acid receptor Proteins 0.000 claims 7
- 230000001225 therapeutic effect Effects 0.000 claims 7
- 208000015181 infectious disease Diseases 0.000 claims 6
- 230000002265 prevention Effects 0.000 claims 6
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims 5
- 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 claims 5
- 239000002537 cosmetic Substances 0.000 claims 5
- 239000003599 detergent Substances 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 229940025703 topical product Drugs 0.000 claims 5
- 230000004931 aggregating effect Effects 0.000 claims 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims 4
- 150000001720 carbohydrates Chemical class 0.000 claims 4
- 235000015872 dietary supplement Nutrition 0.000 claims 4
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 4
- 241000589989 Helicobacter Species 0.000 claims 3
- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000000369 enteropathogenic effect Effects 0.000 claims 3
- 239000005452 food preservative Substances 0.000 claims 3
- 235000019249 food preservative Nutrition 0.000 claims 3
- 230000002458 infectious effect Effects 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000013589 supplement Substances 0.000 claims 3
- 241000607534 Aeromonas Species 0.000 claims 2
- 241000589876 Campylobacter Species 0.000 claims 2
- 241000589875 Campylobacter jejuni Species 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 241000206602 Eukaryota Species 0.000 claims 2
- 241000186781 Listeria Species 0.000 claims 2
- OVRNDRQMDRJTHS-KEWYIRBNSA-N N-acetyl-D-galactosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-KEWYIRBNSA-N 0.000 claims 2
- 229930182474 N-glycoside Natural products 0.000 claims 2
- 241000702670 Rotavirus Species 0.000 claims 2
- 241000607142 Salmonella Species 0.000 claims 2
- 241000607768 Shigella Species 0.000 claims 2
- 241000607598 Vibrio Species 0.000 claims 2
- 241000607626 Vibrio cholerae Species 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- DUKURNFHYQXCJG-JEOLMMCMSA-N alpha-L-Fucp-(1->4)-[beta-D-Galp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical group 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@@H](O)[C@@H](CO)O2)O)[C@@H](NC(C)=O)[C@H](O[C@@H]2[C@H]([C@H](O[C@@H]3[C@H](OC(O)[C@H](O)[C@H]3O)CO)O[C@H](CO)[C@@H]2O)O)O[C@@H]1CO DUKURNFHYQXCJG-JEOLMMCMSA-N 0.000 claims 2
- 125000000837 carbohydrate group Chemical group 0.000 claims 2
- 229940112822 chewing gum Drugs 0.000 claims 2
- 235000015218 chewing gum Nutrition 0.000 claims 2
- 238000002405 diagnostic procedure Methods 0.000 claims 2
- 235000013305 food Nutrition 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- 235000013336 milk Nutrition 0.000 claims 2
- 239000008267 milk Substances 0.000 claims 2
- 210000004080 milk Anatomy 0.000 claims 2
- 239000002324 mouth wash Substances 0.000 claims 2
- 229940051866 mouthwash Drugs 0.000 claims 2
- 230000003071 parasitic effect Effects 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 239000006041 probiotic Substances 0.000 claims 2
- 230000000529 probiotic effect Effects 0.000 claims 2
- 235000018291 probiotics Nutrition 0.000 claims 2
- 125000005629 sialic acid group Chemical group 0.000 claims 2
- 239000003826 tablet Substances 0.000 claims 2
- 239000000606 toothpaste Substances 0.000 claims 2
- 229940034610 toothpaste Drugs 0.000 claims 2
- 231100000033 toxigenic Toxicity 0.000 claims 2
- 230000001551 toxigenic effect Effects 0.000 claims 2
- 241000283690 Bos taurus Species 0.000 claims 1
- 229930182476 C-glycoside Natural products 0.000 claims 1
- 150000000700 C-glycosides Chemical class 0.000 claims 1
- 206010014896 Enterocolitis haemorrhagic Diseases 0.000 claims 1
- 206010017964 Gastrointestinal infection Diseases 0.000 claims 1
- 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 claims 1
- FDJKUWYYUZCUJX-AJKRCSPLSA-N N-glycoloyl-beta-neuraminic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H]1O[C@](O)(C(O)=O)C[C@H](O)[C@H]1NC(=O)CO FDJKUWYYUZCUJX-AJKRCSPLSA-N 0.000 claims 1
- FDJKUWYYUZCUJX-UHFFFAOYSA-N N-glycolyl-beta-neuraminic acid Natural products OCC(O)C(O)C1OC(O)(C(O)=O)CC(O)C1NC(=O)CO FDJKUWYYUZCUJX-UHFFFAOYSA-N 0.000 claims 1
- 229930182475 S-glycoside Natural products 0.000 claims 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims 1
- KBGAYAKRZNYFFG-BOHATCBPSA-N aceneuramic acid Chemical group OC(=O)C(=O)C[C@H](O)[C@@H](NC(=O)C)[C@@H](O)[C@H](O)[C@H](O)CO KBGAYAKRZNYFFG-BOHATCBPSA-N 0.000 claims 1
- 238000004220 aggregation Methods 0.000 claims 1
- 230000002776 aggregation Effects 0.000 claims 1
- 230000000890 antigenic effect Effects 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 235000013361 beverage Nutrition 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 235000013365 dairy product Nutrition 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 210000000981 epithelium Anatomy 0.000 claims 1
- 150000002270 gangliosides Chemical class 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- 150000002341 glycosylamines Chemical class 0.000 claims 1
- 230000002008 hemorrhagic effect Effects 0.000 claims 1
- 210000002865 immune cell Anatomy 0.000 claims 1
- 230000007124 immune defense Effects 0.000 claims 1
- 230000003308 immunostimulating effect Effects 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 210000000936 intestine Anatomy 0.000 claims 1
- 210000000867 larynx Anatomy 0.000 claims 1
- 235000021056 liquid food Nutrition 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000002417 nutraceutical Substances 0.000 claims 1
- 235000021436 nutraceutical agent Nutrition 0.000 claims 1
- 230000002085 persistent effect Effects 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 235000013406 prebiotics Nutrition 0.000 claims 1
- 150000003214 pyranose derivatives Chemical class 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 claims 1
- 239000000057 synthetic resin Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 239000003053 toxin Substances 0.000 claims 1
- 231100000765 toxin Toxicity 0.000 claims 1
- 229940118696 vibrio cholerae Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000011534 incubation Methods 0.000 description 5
- TYALNJQZQRNQNQ-UHFFFAOYSA-N #alpha;2,6-sialyllactose Natural products O1C(C(O)C(O)CO)C(NC(=O)C)C(O)CC1(C(O)=O)OCC1C(O)C(O)C(O)C(OC2C(C(O)C(O)OC2CO)O)O1 TYALNJQZQRNQNQ-UHFFFAOYSA-N 0.000 description 3
- TYALNJQZQRNQNQ-JLYOMPFMSA-N alpha-Neup5Ac-(2->6)-beta-D-Galp-(1->4)-beta-D-Glcp Chemical compound O1[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C[C@@]1(C(O)=O)OC[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)O[C@@H]2CO)O)O1 TYALNJQZQRNQNQ-JLYOMPFMSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- IEQCXFNWPAHHQR-UHFFFAOYSA-N lacto-N-neotetraose Natural products OCC1OC(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)C(NC(=O)C)C(O)C1OC1OC(CO)C(O)C(O)C1O IEQCXFNWPAHHQR-UHFFFAOYSA-N 0.000 description 2
- 229940062780 lacto-n-neotetraose Drugs 0.000 description 2
- RBMYDHMFFAVMMM-PLQWBNBWSA-N neolactotetraose Chemical compound O([C@H]1[C@H](O)[C@H]([C@@H](O[C@@H]1CO)O[C@@H]1[C@H]([C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@@H]1O)O)NC(=O)C)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O RBMYDHMFFAVMMM-PLQWBNBWSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KFEUJDWYNGMDBV-UHFFFAOYSA-N (N-Acetyl)-glucosamin-4-beta-galaktosid Natural products OC1C(NC(=O)C)C(O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 KFEUJDWYNGMDBV-UHFFFAOYSA-N 0.000 description 1
- NQRKYASMKDDGHT-UHFFFAOYSA-N (aminooxy)acetic acid Chemical compound NOCC(O)=O NQRKYASMKDDGHT-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical group N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- KFEUJDWYNGMDBV-LODBTCKLSA-N N-acetyllactosamine Chemical group O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KFEUJDWYNGMDBV-LODBTCKLSA-N 0.000 description 1
- HESSGHHCXGBPAJ-UHFFFAOYSA-N N-acetyllactosamine Natural products CC(=O)NC(C=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O HESSGHHCXGBPAJ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- FYGDTMLNYKFZSV-SKWQFERISA-N alpha-D-Galp-(1->4)-beta-D-Galp-(1->4)-beta-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-SKWQFERISA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000000211 autoradiogram Methods 0.000 description 1
- 230000010065 bacterial adhesion Effects 0.000 description 1
- JMPCSGHAAIDYIN-WASRWFGHSA-N beta-D-GalpNAc-(1->3)-alpha-D-Galp-(1->4)-beta-D-Galp-(1->4)-D-Glcp Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](O[C@@H](O[C@@H]3[C@H](OC(O)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)O[C@H](CO)[C@@H]1O JMPCSGHAAIDYIN-WASRWFGHSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000326 densiometry Methods 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002339 glycosphingolipids Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- ZTFUBGFDKYNHOV-QSADOIOESA-N isoglobotetraosyl ceramide Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(C)=O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O[C@@H]3[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O3)NC(C)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@@H](CO)O1 ZTFUBGFDKYNHOV-QSADOIOESA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000001483 monosaccharide substituent group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002923 oximes Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20021275A FI20021275A0 (fi) | 2002-06-28 | 2002-06-28 | Terapeuttiset koostumukset käytettäväksi ripulien ehkäisyyn tai hoitoon |
| FI20021275 | 2002-06-28 | ||
| FI20030564 | 2003-04-14 | ||
| FI20030564A FI20030564A0 (fi) | 2003-04-14 | 2003-04-14 | Zoonoottisia Helicobacter-lajeja sitovia aineita ja niiden käyttö |
| PCT/FI2003/000528 WO2004002495A1 (en) | 2002-06-28 | 2003-06-30 | Therapeutic compositions for use in prophylaxis or treatment of diarrheas |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006506329A JP2006506329A (ja) | 2006-02-23 |
| JP2006506329A5 true JP2006506329A5 (enExample) | 2006-08-10 |
| JP5219329B2 JP5219329B2 (ja) | 2013-06-26 |
Family
ID=30001920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004516828A Expired - Fee Related JP5219329B2 (ja) | 2002-06-28 | 2003-06-30 | 下痢の予防又は治療用の医薬組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20060014717A1 (enExample) |
| EP (2) | EP1531832B1 (enExample) |
| JP (1) | JP5219329B2 (enExample) |
| AT (1) | ATE428430T1 (enExample) |
| AU (1) | AU2003242799A1 (enExample) |
| DE (1) | DE60327211D1 (enExample) |
| DK (1) | DK1531832T3 (enExample) |
| ES (1) | ES2649736T3 (enExample) |
| IN (1) | IN2004KO01960A (enExample) |
| WO (1) | WO2004002495A1 (enExample) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002952121A0 (en) * | 2002-10-17 | 2002-10-31 | Alchemia Limited | Novel carbohydrate based anti-bacterials |
| HRP20050696B1 (en) | 2003-01-14 | 2008-10-31 | Arena Pharmaceuticals Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| US7132426B2 (en) | 2003-07-14 | 2006-11-07 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| GB0321996D0 (en) * | 2003-09-19 | 2003-10-22 | Novartis Nutrition Ag | Organic compounds |
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| US5225330A (en) * | 1988-08-01 | 1993-07-06 | The United States Of America As Represented By The Department Of Health And Human Services | Diagnostic kit and diagnostic method utilizing carbohydrate receptors |
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| SE9904581D0 (sv) * | 1999-12-15 | 1999-12-15 | A & Science Invest Ab | A novel helicobacter pylori-binding substance and use thereof |
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- 2003-06-30 DE DE60327211T patent/DE60327211D1/de not_active Expired - Lifetime
- 2003-06-30 AT AT03761605T patent/ATE428430T1/de not_active IP Right Cessation
- 2003-06-30 DK DK03761605T patent/DK1531832T3/da active
- 2003-06-30 AU AU2003242799A patent/AU2003242799A1/en not_active Abandoned
- 2003-06-30 ES ES09157883.1T patent/ES2649736T3/es not_active Expired - Lifetime
- 2003-06-30 US US10/518,297 patent/US20060014717A1/en not_active Abandoned
- 2003-06-30 JP JP2004516828A patent/JP5219329B2/ja not_active Expired - Fee Related
- 2003-06-30 WO PCT/FI2003/000528 patent/WO2004002495A1/en not_active Ceased
- 2003-06-30 EP EP09157883.1A patent/EP2272522B1/en not_active Expired - Lifetime
-
2004
- 2004-12-20 IN IN1960KO2004 patent/IN2004KO01960A/en unknown
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