LT3446B - Fucolsylated glycosides as inhibitor of bacterial adherence - Google Patents

Fucolsylated glycosides as inhibitor of bacterial adherence Download PDF

Info

Publication number: LT3446B
Authority: LT; Lithuania
Prior art keywords: fucal; alkyl; group; bridge; compound
Prior art date: 1993-06-25

Application number

LTIP1978A

Other languages

English (en)

Lithuanian (lt)

Inventor

Karin Eklind

Hans Loenn

Anna-Karin Tiden

Original Assignee

Astra Ab

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.)

1993-06-25

Filing date

1994-06-27

Publication date

1995-10-25

1994-06-27 Application filed by Astra Ab filed Critical Astra Ab

1995-01-31 Publication of LTIP1978A publication Critical patent/LTIP1978A/xx

1995-10-25 Publication of LT3446B publication Critical patent/LT3446B/lt

Links

229930182470 glycoside Natural products 0.000 title claims abstract description 13
150000002338 glycosides Chemical class 0.000 title claims description 5
230000001580 bacterial effect Effects 0.000 title description 4
239000003112 inhibitor Substances 0.000 title description 2
-1 oligosaccharide glycoside Chemical class 0.000 claims abstract description 123
150000001875 compounds Chemical class 0.000 claims abstract description 121
238000002360 preparation method Methods 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
210000001156 gastric mucosa Anatomy 0.000 claims abstract description 7
208000015181 infectious disease Diseases 0.000 claims abstract description 6
238000011321 prophylaxis Methods 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 4
238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 92
239000000203 mixture Substances 0.000 claims description 70
125000000217 alkyl group Chemical group 0.000 claims description 49
239000011159 matrix material Substances 0.000 claims description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 24
125000003118 aryl group Chemical group 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 claims description 18
108091006905 Human Serum Albumin Proteins 0.000 claims description 16
102000008100 Human Serum Albumin Human genes 0.000 claims description 16
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
150000002772 monosaccharides Chemical class 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
241000590002 Helicobacter pylori Species 0.000 claims description 12
238000009472 formulation Methods 0.000 claims description 12
125000000524 functional group Chemical group 0.000 claims description 12
229940037467 helicobacter pylori Drugs 0.000 claims description 12
125000004043 oxo group Chemical group O=* 0.000 claims description 12
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 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
108091003079 Bovine Serum Albumin Proteins 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
229940098773 bovine serum albumin Drugs 0.000 claims description 10
230000002496 gastric effect Effects 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 8
239000004098 Tetracycline Substances 0.000 claims description 8
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
235000019364 tetracycline Nutrition 0.000 claims description 8
150000003522 tetracyclines Chemical class 0.000 claims description 8
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 claims description 6
PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 claims description 6
208000025865 Ulcer Diseases 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 6
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 6
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 claims description 6
WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 claims description 5
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 description 5
208000007882 Gastritis Diseases 0.000 claims description 5
WQZGKKKJIJFFOK-DHVFOXMCSA-N L-galactose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-DHVFOXMCSA-N 0.000 claims description 5
WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 claims description 5
WQZGKKKJIJFFOK-QRXFDPRISA-N L-gulose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QRXFDPRISA-N 0.000 claims description 5
WQZGKKKJIJFFOK-ZNVMLXAYSA-N L-idopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-ZNVMLXAYSA-N 0.000 claims description 5
WQZGKKKJIJFFOK-JFNONXLTSA-N L-mannopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-JFNONXLTSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
GZCGUPFRVQAUEE-ZXXMMSQZSA-N aldehydo-D-idose Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-ZXXMMSQZSA-N 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
229910052797 bismuth Inorganic materials 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 5
229920001223 polyethylene glycol Polymers 0.000 claims description 5
125000001443 terpenyl group Chemical group 0.000 claims description 5
231100000397 ulcer Toxicity 0.000 claims description 5
HWSISDHAHRVNMT-UHFFFAOYSA-N Bismuth subnitrate Chemical compound O[NH+]([O-])O[Bi](O[N+]([O-])=O)O[N+]([O-])=O HWSISDHAHRVNMT-UHFFFAOYSA-N 0.000 claims description 4
229930182566 Gentamicin Natural products 0.000 claims description 4
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 4
IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 claims description 4
230000004913 activation Effects 0.000 claims description 4
229960004821 amikacin Drugs 0.000 claims description 4
LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 4
150000001413 amino acids Chemical class 0.000 claims description 4
229940126575 aminoglycoside Drugs 0.000 claims description 4
229960003022 amoxicillin Drugs 0.000 claims description 4
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 4
229960000723 ampicillin Drugs 0.000 claims description 4
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 4
229940069428 antacid Drugs 0.000 claims description 4
239000003159 antacid agent Substances 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
239000003782 beta lactam antibiotic agent Substances 0.000 claims description 4
150000001621 bismuth Chemical class 0.000 claims description 4
229960001482 bismuth subnitrate Drugs 0.000 claims description 4
229960000782 bismuth subsalicylate Drugs 0.000 claims description 4
230000000903 blocking effect Effects 0.000 claims description 4
229960000603 cefalotin Drugs 0.000 claims description 4
OKBVVJOGVLARMR-QSWIMTSFSA-N cefixime Chemical compound S1C(N)=NC(C(=N\OCC(O)=O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 OKBVVJOGVLARMR-QSWIMTSFSA-N 0.000 claims description 4
229960002129 cefixime Drugs 0.000 claims description 4
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 claims description 4
229960001380 cimetidine Drugs 0.000 claims description 4
CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims description 4
229960003405 ciprofloxacin Drugs 0.000 claims description 4
229960002626 clarithromycin Drugs 0.000 claims description 4
AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 claims description 4
229960003722 doxycycline Drugs 0.000 claims description 4
IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 claims description 4
229960002549 enoxacin Drugs 0.000 claims description 4
229960003276 erythromycin Drugs 0.000 claims description 4
XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 claims description 4
229960001596 famotidine Drugs 0.000 claims description 4
229960002518 gentamicin Drugs 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
229960000318 kanamycin Drugs 0.000 claims description 4
229930027917 kanamycin Natural products 0.000 claims description 4
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 4
229930182823 kanamycin A Natural products 0.000 claims description 4
MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims description 4
229960003174 lansoprazole Drugs 0.000 claims description 4
239000003120 macrolide antibiotic agent Substances 0.000 claims description 4
229940041033 macrolides Drugs 0.000 claims description 4
OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 claims description 4
229960001180 norfloxacin Drugs 0.000 claims description 4
229960000381 omeprazole Drugs 0.000 claims description 4
229940127240 opiate Drugs 0.000 claims description 4
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 4
229960005019 pantoprazole Drugs 0.000 claims description 4
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 claims description 4
229960000620 ranitidine Drugs 0.000 claims description 4
229940083037 simethicone Drugs 0.000 claims description 4
MNQYNQBOVCBZIQ-JQOFMKNESA-A sucralfate Chemical compound O[Al](O)OS(=O)(=O)O[C@@H]1[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](COS(=O)(=O)O[Al](O)O)O[C@H]1O[C@@]1(COS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)O1 MNQYNQBOVCBZIQ-JQOFMKNESA-A 0.000 claims description 4
229960004291 sucralfate Drugs 0.000 claims description 4
229960002180 tetracycline Drugs 0.000 claims description 4
229930101283 tetracycline Natural products 0.000 claims description 4
229940040944 tetracyclines Drugs 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
229910000014 Bismuth subcarbonate Inorganic materials 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
239000003242 anti bacterial agent Substances 0.000 claims description 3
MGLUJXPJRXTKJM-UHFFFAOYSA-L bismuth subcarbonate Chemical compound O=[Bi]OC(=O)O[Bi]=O MGLUJXPJRXTKJM-UHFFFAOYSA-L 0.000 claims description 3
229940036358 bismuth subcarbonate Drugs 0.000 claims description 3
229960004645 bismuth subcitrate Drugs 0.000 claims description 3
ZQUAVILLCXTKTF-UHFFFAOYSA-H bismuth;tripotassium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [K+].[K+].[K+].[Bi+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZQUAVILLCXTKTF-UHFFFAOYSA-H 0.000 claims description 3
229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
229960000282 metronidazole Drugs 0.000 claims description 3
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 3
229960000564 nitrofurantoin Drugs 0.000 claims description 3
NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 claims description 3
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239000002132 β-lactam antibiotic Substances 0.000 claims description 3
229940124586 β-lactam antibiotics Drugs 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
RJZNFXWQRHAVBP-UHFFFAOYSA-I aluminum;magnesium;pentahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Al+3] RJZNFXWQRHAVBP-UHFFFAOYSA-I 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000003827 glycol group Chemical group 0.000 claims description 2
239000000348 glycosyl donor Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
239000000347 magnesium hydroxide Substances 0.000 claims description 2
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238000004519 manufacturing process Methods 0.000 claims description 2
SGXXNSQHWDMGGP-IZZDOVSWSA-N nizatidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CSC(CN(C)C)=N1 SGXXNSQHWDMGGP-IZZDOVSWSA-N 0.000 claims description 2
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230000028327 secretion Effects 0.000 claims description 2
125000002657 sphingoid group Chemical group 0.000 claims description 2
125000002345 steroid group Chemical group 0.000 claims description 2
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
239000004599 antimicrobial Substances 0.000 claims 4
SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims 3
WKJGTOYAEQDNIA-IOOZKYRYSA-N (6r,7r)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate Chemical compound O.C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 WKJGTOYAEQDNIA-IOOZKYRYSA-N 0.000 claims 3
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 3
ZREIPSZUJIFJNP-UHFFFAOYSA-K bismuth subsalicylate Chemical compound C1=CC=C2O[Bi](O)OC(=O)C2=C1 ZREIPSZUJIFJNP-UHFFFAOYSA-K 0.000 claims 3
JIFPTBLGXRKRAO-UHFFFAOYSA-K aluminum;magnesium;hydroxide;sulfate Chemical compound [OH-].[Mg+2].[Al+3].[O-]S([O-])(=O)=O JIFPTBLGXRKRAO-UHFFFAOYSA-K 0.000 claims 2
229960003563 calcium carbonate Drugs 0.000 claims 2
229960005091 chloramphenicol Drugs 0.000 claims 2
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235000007586 terpenes Nutrition 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
150000004044 tetrasaccharides Chemical class 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
229940035024 thioglycerol Drugs 0.000 description 1
125000001239 threonyl group Chemical group 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000011200 topical administration Methods 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
230000010415 tropism Effects 0.000 description 1
125000005454 tryptophanyl group Chemical group 0.000 description 1
125000002233 tyrosyl group Chemical group 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
125000002948 undecyl group Chemical group [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
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
125000002114 valyl group Chemical group 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Communicable Diseases (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Saccharide Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

LTIP1978A 1993-06-25 1994-06-27 Fucolsylated glycosides as inhibitor of bacterial adherence LT3446B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK93761A DK76193D0 (da)	1993-06-25	1993-06-25	Kulhydratderivater

Publications (2)

Publication Number	Publication Date
LTIP1978A LTIP1978A (en)	1995-01-31
LT3446B true LT3446B (en)	1995-10-25

Family

ID=8097261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP1978A LT3446B (en)	1993-06-25	1994-06-27	Fucolsylated glycosides as inhibitor of bacterial adherence

Country Status (9)

Country	Link
EP (1)	EP0706528A1 (da)
JP (1)	JPH08512026A (da)
AU (1)	AU7089194A (da)
CA (1)	CA2164961A1 (da)
DK (1)	DK76193D0 (da)
IL (1)	IL110074A0 (da)
IS (1)	IS4181A (da)
LT (1)	LT3446B (da)
WO (1)	WO1995000527A1 (da)

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SE9901007D0 (sv) *	1999-03-19	1999-03-19	Thomas Boren	Use of fucosylated sialylated N-acetyl lactosamin carbohydrate structures for inhibition of bacterial adherence
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
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
EP2692740A1 (en) *	2012-07-30	2014-02-05	Le Centre National De La Recherche Scientifique	Glycan compositions, processes for preparing the same and their uses as a drug
US9867841B2 (en)	2012-12-07	2018-01-16	Glycomimetics, Inc.	Compounds, compositions and methods using E-selectin antagonists for mobilization of hematopoietic cells
CN105101972A (zh) *	2013-01-31	2015-11-25	先锋国际良种公司	用于改善植物生长和产量的合成型脂质几丁寡糖
EP3013365B1 (en) *	2013-06-26	2019-06-05	Academia Sinica	Rm2 antigens and use thereof
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
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KR20200104889A (ko)	2017-12-29	2020-09-04	글리코미메틱스, 인크.	E-셀렉틴 및 갈렉틴-3의 이종이기능성 억제제
KR20200128025A (ko)	2018-03-05	2020-11-11	글리코미메틱스, 인크.	급성 골수성 백혈병 및 관련 병태의 치료 방법
JP2021534196A (ja)	2018-08-23	2021-12-09	シージェンインコーポレイテッド	抗ｔｉｇｉｔ抗体
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1993
- 1993-06-25 DK DK93761A patent/DK76193D0/da not_active Application Discontinuation
1994
- 1994-06-17 EP EP94919945A patent/EP0706528A1/en not_active Withdrawn
- 1994-06-17 JP JP7502720A patent/JPH08512026A/ja active Pending
- 1994-06-17 AU AU70891/94A patent/AU7089194A/en not_active Abandoned
- 1994-06-17 WO PCT/SE1994/000604 patent/WO1995000527A1/en not_active Ceased
- 1994-06-17 CA CA002164961A patent/CA2164961A1/en not_active Abandoned
- 1994-06-21 IL IL11007494A patent/IL110074A0/xx unknown
- 1994-06-22 IS IS4181A patent/IS4181A/is unknown
- 1994-06-27 LT LTIP1978A patent/LT3446B/lt not_active IP Right Cessation

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Also Published As

Publication number	Publication date
IL110074A0 (en)	1994-10-07
AU7089194A (en)	1995-01-17
WO1995000527A1 (en)	1995-01-05
LTIP1978A (en)	1995-01-31
IS4181A (is)	1994-12-26
CA2164961A1 (en)	1995-01-05
EP0706528A1 (en)	1996-04-17
JPH08512026A (ja)	1996-12-17
DK76193D0 (da)	1993-06-25

Legal Events

Date	Code	Title	Description
1997-01-27	MM9A	Lapsed patents	Effective date: 19960627

Publication	Publication Date	Title
LT3446B (en)	1995-10-25	Fucolsylated glycosides as inhibitor of bacterial adherence
EP0714903B1 (de)	2002-05-15	Kohlenhydratkonjugate als Inhibitoren der Zelladhäsion
JP6028284B2 (ja)	2016-11-16	新規硫酸化オリゴ糖誘導体
EP1720889B1 (en)	2014-11-26	Sulfated oligosaccharide derivatives
JP2003527346A (ja)	2003-09-16	合成オリゴマンノシド並びにその調製および使用
EP1575619A1 (en)	2005-09-21	Oligosaccharides and conjugates thereof for the treatement of pseudomonas bacteria infection
US20040219158A1 (en)	2004-11-04	Compositions and methods for diagnosis and therapy of medical conditions involving infection with pseudomonas bacteria
CZ2001637A3 (cs)	2001-10-17	Fosfoglykolipidová sloučenina, její pouľití a farmaceutické kompozice ji obsahující
WO2005027936A2 (en)	2005-03-31	Pharmaceutical compositions and therapeutical treatment with oligo-beta-(1, 3)-glucans
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
US20240024489A1 (en)	2024-01-25	Protected disaccharides, their process of preparation and their use in the synthesis of zwitterionic oligosaccharides, and conjugates thereof
DE10138935B4 (de)	2007-08-02	Synthetische Verbindungen vom Nicht-Mucintyp oder ihre mit einem Träger konjugierten Verbindungen, unter deren Verwendung hergestellte monoclonale Antikörper, diese umfassende Antitumormittel Immunstimulantien und Mittel gegen das humane Immundefizienzvirus
JPH09509931A (ja)	1997-10-07	胃潰瘍及び十二指腸潰瘍を治療及び阻止する方法
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CN117651707A (zh)	2024-03-05	新的合成的tlr4受体激动剂
CA2253913A1 (en)	1997-11-13	Bismuth salt of sialyloligosaccharide and a method for treating and inhibiting gastric and duodenal ulcers with same
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HK1197915A (en)	2015-02-27	Sulfated oligosaccharide derivatives
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