CA2480578C - Anomeric derivatives of monosaccharides - Google Patents
Anomeric derivatives of monosaccharides Download PDFInfo
- Publication number
- CA2480578C CA2480578C CA2480578A CA2480578A CA2480578C CA 2480578 C CA2480578 C CA 2480578C CA 2480578 A CA2480578 A CA 2480578A CA 2480578 A CA2480578 A CA 2480578A CA 2480578 C CA2480578 C CA 2480578C
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- atoms
- moiety
- group
- hydrogen
- 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.)
- Expired - Lifetime
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- 150000002772 monosaccharides Chemical class 0.000 title claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 186
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 125000004429 atom Chemical group 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- -1 guanidiniums Chemical class 0.000 claims description 26
- 150000001720 carbohydrates Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 5
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 5
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 5
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000002466 imines Chemical class 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
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000001409 amidines Chemical class 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000003999 cyclitols Chemical group 0.000 claims 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 24
- 125000005001 aminoaryl group Chemical group 0.000 abstract description 7
- 150000002431 hydrogen Chemical group 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract description 5
- 125000005251 aryl acyl group Chemical group 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 125000005253 heteroarylacyl group Chemical group 0.000 abstract description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 4
- 125000005214 aminoheteroaryl group Chemical group 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract description 4
- 125000004001 thioalkyl group Chemical group 0.000 abstract description 4
- 125000005000 thioaryl group Chemical group 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 2
- 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 113
- 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 81
- 238000000034 method Methods 0.000 description 70
- 230000015572 biosynthetic process Effects 0.000 description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 51
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- 229910001868 water Inorganic materials 0.000 description 45
- 239000011347 resin Substances 0.000 description 43
- 229920005989 resin Polymers 0.000 description 43
- 238000003786 synthesis reaction Methods 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- 239000007787 solid Substances 0.000 description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 235000000346 sugar Nutrition 0.000 description 28
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
- 239000012071 phase Substances 0.000 description 24
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- 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
- 238000006243 chemical reaction Methods 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000014633 carbohydrates Nutrition 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 125000006239 protecting group Chemical group 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000007790 solid phase Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 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
- 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 10
- 229930182474 N-glycoside Natural products 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000029936 alkylation Effects 0.000 description 9
- 238000005804 alkylation reaction Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 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 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
- 238000003776 cleavage reaction Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000000105 evaporative light scattering detection Methods 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 230000007017 scission Effects 0.000 description 8
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 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
- 150000001412 amines Chemical class 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 6
- 150000001793 charged compounds Chemical class 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229930182476 C-glycoside Natural products 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 230000006181 N-acylation Effects 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- ZLDHMFFPUSYDLN-UHFFFAOYSA-N diazonio-[4-hydroxy-5-[(4-methoxy-4-oxobutanoyl)amino]-2-[(4-methoxyphenyl)methoxymethyl]oxan-3-yl]azanide Chemical compound N#[N+][N-]C1C(O)C(NC(=O)CCC(=O)OC)COC1COCC1=CC=C(OC)C=C1 ZLDHMFFPUSYDLN-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 4
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- 239000000816 peptidomimetic Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 108090000765 processed proteins & peptides Chemical group 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229960002920 sorbitol Drugs 0.000 description 4
- NQPHMXWPDCSHTE-UHFFFAOYSA-N trifluoromethanesulfonyl azide Chemical compound FC(F)(F)S(=O)(=O)N=[N+]=[N-] NQPHMXWPDCSHTE-UHFFFAOYSA-N 0.000 description 4
- 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
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 3
- 150000000700 C-glycosides Chemical class 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 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 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000003875 Wang resin Substances 0.000 description 3
- 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 description 3
- 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
- LHORKHUCKGSKCN-UHFFFAOYSA-N [5-amino-4-ethoxy-2-[(4-methoxyphenyl)methoxymethyl]oxan-3-yl]-diazonioazanide Chemical compound [N-]=[N+]=NC1C(OCC)C(N)COC1COCC1=CC=C(OC)C=C1 LHORKHUCKGSKCN-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- FAVAVMFXAKZTMV-UHFFFAOYSA-N dibutylboranyl trifluoromethanesulfonate Chemical compound CCCCB(CCCC)OS(=O)(=O)C(F)(F)F FAVAVMFXAKZTMV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 101150009274 nhr-1 gene Proteins 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 description 3
- 238000010530 solution phase reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 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 3
- 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 3
- 238000005406 washing Methods 0.000 description 3
- NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 description 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- XGWHCWUINQZMQG-UHFFFAOYSA-N C1=CC(OC)=CC=C1COCC1C(N=[N+]=[N-])C(OCC(=O)OC(C)(C)C)C(NC(C)=O)CO1 Chemical compound C1=CC(OC)=CC=C1COCC1C(N=[N+]=[N-])C(OCC(=O)OC(C)(C)C)C(NC(C)=O)CO1 XGWHCWUINQZMQG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 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
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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2480578A1 CA2480578A1 (en) | 2003-10-09 |
| CA2480578C true CA2480578C (en) | 2013-01-08 |
Family
ID=3835023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2480578A Expired - Lifetime CA2480578C (en) | 2002-03-28 | 2003-03-28 | Anomeric derivatives of monosaccharides |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7737287B2 (https=) |
| EP (1) | EP1487812A4 (https=) |
| JP (1) | JP4610197B2 (https=) |
| CN (1) | CN100537556C (https=) |
| AU (1) | AUPS143402A0 (https=) |
| CA (1) | CA2480578C (https=) |
| DE (1) | DE03745223T1 (https=) |
| WO (1) | WO2003082846A1 (https=) |
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 |
| US7125853B2 (en) | 2003-01-07 | 2006-10-24 | Kemin Pharma B.V.B.A. | Bicyclic carbohydrate compounds useful in the treatment of infections caused by Flaviviridae sp., such as hepatitis C and bovine viral diarrhea viruses |
| WO2004062590A2 (en) | 2003-01-07 | 2004-07-29 | Kemin Pharma Europe B.V.B.A. | Bicyclic carbohydrates as antiprotozoal bioactive for the treatment of infections caused by parasites |
| 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 |
| WO2006081616A1 (en) * | 2005-02-04 | 2006-08-10 | Alchemia Limited | Classes of compounds that interact with integrins |
| JP5174672B2 (ja) * | 2005-10-04 | 2013-04-03 | アルケミア リミティッド | 薬物設計の方法 |
| US7989422B2 (en) | 2005-12-22 | 2011-08-02 | Alchemia Limited | Antibacterial agents |
| IL294515A (en) | 2020-01-31 | 2022-09-01 | Avilar Therapeutics Inc | Compounds bind asgpr to degrade extracellular proteins |
| WO2022235699A2 (en) | 2021-05-03 | 2022-11-10 | Avilar Therapeutics, Inc. | Potent asgpr-binding compounds for the degradation of immunoglobulins and other proteins |
| WO2024118503A1 (en) | 2022-11-28 | 2024-06-06 | 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 |
| AU7286696A (en) * | 1995-10-13 | 1997-05-07 | 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 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 CA CA2480578A patent/CA2480578C/en not_active Expired - Lifetime
- 2003-03-28 CN CNB038073757A patent/CN100537556C/zh not_active Expired - Lifetime
- 2003-03-28 EP EP03745223A patent/EP1487812A4/en not_active Withdrawn
- 2003-03-28 JP JP2003580313A patent/JP4610197B2/ja not_active Expired - Fee Related
- 2003-03-28 DE DE03745223T patent/DE03745223T1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1642932A (zh) | 2005-07-20 |
| JP4610197B2 (ja) | 2011-01-12 |
| DE03745223T1 (de) | 2007-05-03 |
| AUPS143402A0 (en) | 2002-05-09 |
| EP1487812A1 (en) | 2004-12-22 |
| EP1487812A4 (en) | 2006-07-26 |
| WO2003082846A1 (en) | 2003-10-09 |
| CN100537556C (zh) | 2009-09-09 |
| CA2480578A1 (en) | 2003-10-09 |
| JP2005526813A (ja) | 2005-09-08 |
| US7737287B2 (en) | 2010-06-15 |
| US20050245746A1 (en) | 2005-11-03 |
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| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230328 |