JP4610197B2 - 単糖のアノマー誘導体 - Google Patents
単糖のアノマー誘導体 Download PDFInfo
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- JP4610197B2 JP4610197B2 JP2003580313A JP2003580313A JP4610197B2 JP 4610197 B2 JP4610197 B2 JP 4610197B2 JP 2003580313 A JP2003580313 A JP 2003580313A JP 2003580313 A JP2003580313 A JP 2003580313A JP 4610197 B2 JP4610197 B2 JP 4610197B2
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- 150000001875 compounds Chemical class 0.000 claims description 106
- 238000000034 method Methods 0.000 claims description 78
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- 239000011347 resin Substances 0.000 claims description 47
- 229920005989 resin Polymers 0.000 claims description 47
- 230000015572 biosynthetic process Effects 0.000 claims description 42
- 238000003786 synthesis reaction Methods 0.000 claims description 34
- -1 tantagel Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000006239 protecting group Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 150000001241 acetals Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
- 150000001540 azides Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
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- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
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- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 6
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- 150000002466 imines Chemical class 0.000 claims description 6
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- 229940124530 sulfonamide Drugs 0.000 claims description 6
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- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical class COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 230000003100 immobilizing effect Effects 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 238000001308 synthesis method Methods 0.000 claims description 3
- FZTIWOBQQYPTCJ-UHFFFAOYSA-N 4-[4-(4-carboxyphenyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(O)=O)C=C1 FZTIWOBQQYPTCJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 6
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 239000012039 electrophile Substances 0.000 claims 1
- 238000007429 general method Methods 0.000 description 148
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
- 239000000243 solution Substances 0.000 description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- 239000002904 solvent Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- 239000007787 solid Substances 0.000 description 29
- 235000000346 sugar Nutrition 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000012071 phase Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- 0 C[C@](C1OC(C)=O)[C@@](*)*(C2)C2[C@]1O Chemical compound C[C@](C1OC(C)=O)[C@@](*)*(C2)C2[C@]1O 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 150000001720 carbohydrates Chemical class 0.000 description 14
- 239000007790 solid phase Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000014633 carbohydrates Nutrition 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 11
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 125000004404 heteroalkyl group Chemical group 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000003776 cleavage reaction Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000007017 scission Effects 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- FBPFZTCFMRRESA-FBXFSONDSA-N Allitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-FBXFSONDSA-N 0.000 description 7
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 7
- 229930182474 N-glycoside Natural products 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
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- 238000005804 alkylation reaction Methods 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 5
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 5
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- 125000005001 aminoaryl group Chemical group 0.000 description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
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- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 5
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 4
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
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- YCLBQZBBDBAELT-UHFFFAOYSA-N [5-[(2-acetyloxyacetyl)amino]-4-hydroxy-2-[(4-methoxyphenyl)methoxymethyl]oxan-3-yl]-diazonioazanide Chemical compound C1=CC(OC)=CC=C1COCC1C(N=[N+]=[N-])C(O)C(NC(=O)COC(C)=O)CO1 YCLBQZBBDBAELT-UHFFFAOYSA-N 0.000 description 3
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- 125000005214 aminoheteroaryl group Chemical group 0.000 description 3
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- WUCLSQKRLCSPCF-UHFFFAOYSA-N diazonio-[2-[(4-methoxyphenyl)methoxymethyl]-5-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]-4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]oxan-3-yl]azanide Chemical compound C1=CC(OC)=CC=C1COCC1C(N=[N+]=[N-])C(OCC(=O)OC(C)(C)C)C(NC(=O)CCNC(=O)OC(C)(C)C)CO1 WUCLSQKRLCSPCF-UHFFFAOYSA-N 0.000 description 3
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- 239000000556 agonist Substances 0.000 description 2
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPS1434A AUPS143402A0 (en) | 2002-03-28 | 2002-03-28 | Anomeric derivatives of monosaccharides |
| AUPS1434 | 2002-03-28 | ||
| PCT/AU2003/000384 WO2003082846A1 (en) | 2002-03-28 | 2003-03-28 | Anomeric derivatives of monosaccharides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005526813A JP2005526813A (ja) | 2005-09-08 |
| JP2005526813A5 JP2005526813A5 (enExample) | 2006-03-16 |
| JP4610197B2 true JP4610197B2 (ja) | 2011-01-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003580313A Expired - Fee Related JP4610197B2 (ja) | 2002-03-28 | 2003-03-28 | 単糖のアノマー誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7737287B2 (enExample) |
| EP (1) | EP1487812A4 (enExample) |
| JP (1) | JP4610197B2 (enExample) |
| CN (1) | CN100537556C (enExample) |
| AU (1) | AUPS143402A0 (enExample) |
| CA (1) | CA2480578C (enExample) |
| DE (1) | DE03745223T1 (enExample) |
| WO (1) | WO2003082846A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7138531B2 (en) | 2001-10-15 | 2006-11-21 | Kemin Pharma B.V.B.A. | Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity |
| AU2002950657A0 (en) | 2002-08-08 | 2002-09-12 | Alchemia Limited | Derivatives of monosaccharides for drug discovery |
| AU2002951995A0 (en) | 2002-10-11 | 2002-10-31 | Alchemia Limited | Classes of compounds that interact with gpcrs |
| US7125854B2 (en) | 2003-01-07 | 2006-10-24 | Kemin Pharma B.V.B.A. | Bicyclic carbohydrates as antiprotozoal bioactive for the treatment of infections caused by parasites |
| JP4707397B2 (ja) | 2003-01-07 | 2011-06-22 | ケミン・ファーマ・ヨーロッパ・ビー・ブイ・ビー・エイ | Ｃ型肝炎及びウシウイルス性下痢のウイルスのようなフラビウイルス科に分類される種によって引き起こされる感染の治療に有用な二環式炭水化物化合物 |
| US7368475B2 (en) | 2003-03-12 | 2008-05-06 | Kemin Pharma Bvba | Furanose-type bicyclic carbohydrates with biological activity |
| US7098243B2 (en) | 2003-09-16 | 2006-08-29 | Kemin Pharma Europe B.V.B.A. | Bicyclic carbohydrates as antiviral bioactives for the treatment of infections caused by the alphaherpesvirinae HSV-1 and HSV-2 |
| AU2006209794B2 (en) * | 2005-02-04 | 2010-07-08 | Alchemia Limited | Classes of compounds that interact with integrins |
| DE06704810T1 (de) * | 2005-02-04 | 2008-05-21 | Alchemia Ltd., Eight Mile Plains | Mit integrinen interagierende verbindungsklassen |
| PL1934388T3 (pl) * | 2005-10-04 | 2013-04-30 | Alchemia Ltd | Sposób projektowania leków |
| WO2007070947A1 (en) * | 2005-12-22 | 2007-06-28 | Alchemia Ltd | Antibacterial agents |
| WO2021155317A1 (en) | 2020-01-31 | 2021-08-05 | Avilar Therapeutics, Inc. | Asgpr-binding compounds for the degradation of extracellular proteins |
| KR20240017423A (ko) | 2021-05-03 | 2024-02-07 | 아빌라 테라퓨틱스, 인크. | 이뮤노글로불린 및 다른 단백질의 분해를 위한 강력한 asgpr-결합 화합물 |
| US12116382B2 (en) | 2022-11-28 | 2024-10-15 | Hongene Biotech Corporation | Functionalized N-acetylgalactosamine analogs |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5331664A (en) * | 1976-09-02 | 1978-03-25 | Suami T | Production of novel nitroso urea derivatives |
| DE3347522A1 (de) * | 1983-12-30 | 1985-07-11 | Troponwerke GmbH & Co KG, 5000 Köln | N-glycosylierte carbonsaeureamid-derivate als mittel bei der bekaempfung von erkrankungen des rheumatischen formenkreises |
| DE3521994A1 (de) * | 1985-06-20 | 1987-01-02 | Bayer Ag | N-(2-aminoacylamido-2-desoxy-hexosyl)-amide-, -carbamate und -harnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| HU208146B (en) * | 1989-11-14 | 1993-08-30 | Biogal Gyogyszergyar | Process for producing aminobenzoic acid-n-glycoside derivatives |
| US5449785A (en) * | 1991-07-24 | 1995-09-12 | Hoffmann-La Roche Inc. | Cyclohexane derivatives |
| JPH07242684A (ja) * | 1994-03-02 | 1995-09-19 | Japan Tobacco Inc | 新規なグルクロン酸化合物 |
| US5491152A (en) * | 1994-03-23 | 1996-02-13 | The Du Pont Merck Pharmaceutical Company | Derivatives of cyclic ethers and sulfides for the treatment of atherosclerosis |
| WO1997014709A1 (en) * | 1995-10-13 | 1997-04-24 | F. Hoffmann-La Roche Ag | Antisense oligomers |
| AUPO190596A0 (en) * | 1996-08-26 | 1996-09-19 | Alchemia Pty Ltd | Oligosaccharide synthesis |
| JP2002502393A (ja) * | 1997-05-29 | 2002-01-22 | インカラ・ファーマシューティカルズ・コーポレーション | 炭水化物骨格化合物及びライブラリー |
| US6197963B1 (en) * | 1998-08-13 | 2001-03-06 | The Trustees Of The University Of Pennsylvania | Non-peptide peptidomimetics |
| CA2415368A1 (en) * | 2000-07-13 | 2002-01-31 | Yi Jin | Synthesis and antiviral evaluation of nucleic acid based (nab) libraries |
| AUPR079700A0 (en) * | 2000-10-17 | 2000-11-09 | Alchemia Pty Ltd | Combinatorial libraries of monosaccharides |
| AUPR084400A0 (en) | 2000-10-18 | 2000-11-09 | Alchemia Pty Ltd | Immunoadjuvant systems |
-
2002
- 2002-03-28 AU AUPS1434A patent/AUPS143402A0/en not_active Abandoned
-
2003
- 2003-03-28 EP EP03745223A patent/EP1487812A4/en not_active Withdrawn
- 2003-03-28 CA CA2480578A patent/CA2480578C/en not_active Expired - Lifetime
- 2003-03-28 WO PCT/AU2003/000384 patent/WO2003082846A1/en not_active Ceased
- 2003-03-28 US US10/509,092 patent/US7737287B2/en active Active
- 2003-03-28 JP JP2003580313A patent/JP4610197B2/ja not_active Expired - Fee Related
- 2003-03-28 CN CNB038073757A patent/CN100537556C/zh not_active Expired - Lifetime
- 2003-03-28 DE DE03745223T patent/DE03745223T1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US7737287B2 (en) | 2010-06-15 |
| JP2005526813A (ja) | 2005-09-08 |
| WO2003082846A1 (en) | 2003-10-09 |
| EP1487812A1 (en) | 2004-12-22 |
| CN1642932A (zh) | 2005-07-20 |
| EP1487812A4 (en) | 2006-07-26 |
| CA2480578C (en) | 2013-01-08 |
| CN100537556C (zh) | 2009-09-09 |
| DE03745223T1 (de) | 2007-05-03 |
| AUPS143402A0 (en) | 2002-05-09 |
| CA2480578A1 (en) | 2003-10-09 |
| US20050245746A1 (en) | 2005-11-03 |
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