CA1068688A - Preparation d'ethers de monosaccharides - Google Patents

Preparation d'ethers de monosaccharides

Info

Publication number: CA1068688A
Authority: CA; Canada
Prior art keywords: group; carbon atoms; residue; propyl; chain length
Prior art date: 1975-03-28
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

Application number

CA248,641A

Other languages

English (en)

Inventor

Paul Gordon

Bruce Ronsen

Shrikant V. Kulkarni

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Alseres Pharmaceuticals Inc

Original Assignee

Strategic Medial Research Corp

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.)

1975-03-28

Filing date

1976-03-24

Publication date

1979-12-25

1975-03-28 Priority claimed from US05/563,080 external-priority patent/US4056322A/en

1976-03-24 Application filed by Strategic Medial Research Corp filed Critical Strategic Medial Research Corp

1979-12-25 Application granted granted Critical

1979-12-25 Publication of CA1068688A publication Critical patent/CA1068688A/fr

Status Expired legal-status Critical Current

Links

150000002772 monosaccharides Chemical class 0.000 title claims abstract description 46
238000002360 preparation method Methods 0.000 title description 9
150000002170 ethers Chemical class 0.000 title description 6
238000000034 method Methods 0.000 claims abstract description 76
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 68
238000006243 chemical reaction Methods 0.000 claims abstract description 44
150000002771 monosaccharide derivatives Chemical class 0.000 claims abstract description 41
150000004820 halides Chemical class 0.000 claims abstract description 36
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
150000007529 inorganic bases Chemical class 0.000 claims abstract description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
125000004185 ester group Chemical group 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 17
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
239000007787 solid Substances 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
230000002378 acidificating effect Effects 0.000 claims abstract description 14
150000002402 hexoses Chemical class 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
239000000460 chlorine Substances 0.000 claims abstract description 11
150000002386 heptoses Chemical class 0.000 claims abstract description 11
150000007524 organic acids Chemical group 0.000 claims abstract description 11
239000003960 organic solvent Substances 0.000 claims abstract description 11
125000004036 acetal group Chemical group 0.000 claims abstract description 10
150000002972 pentoses Chemical class 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
150000002576 ketones Chemical class 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
239000000126 substance Substances 0.000 claims abstract description 9
150000001299 aldehydes Chemical class 0.000 claims abstract description 8
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
150000001340 alkali metals Chemical class 0.000 claims abstract description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 7
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
125000004122 cyclic group Chemical group 0.000 claims abstract description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 5
229910052740 iodine Inorganic materials 0.000 claims abstract description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
239000011630 iodine Substances 0.000 claims abstract description 4
229910052751 metal Inorganic materials 0.000 claims abstract description 4
239000002184 metal Substances 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
239000011593 sulfur Substances 0.000 claims abstract description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 66
-1 hydrocarbon radical Chemical group 0.000 claims description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
150000003254 radicals Chemical class 0.000 claims description 24
238000006460 hydrolysis reaction Methods 0.000 claims description 22
230000007062 hydrolysis Effects 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 15
239000012736 aqueous medium Substances 0.000 claims description 14
229930195733 hydrocarbon Natural products 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 12
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
230000001590 oxidative effect Effects 0.000 claims description 11
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 8
239000008103 glucose Substances 0.000 claims description 7
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 description 6
229960003082 galactose Drugs 0.000 claims description 6
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 5
239000002516 radical scavenger Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
150000001924 cycloalkanes Chemical class 0.000 claims description 2
150000004679 hydroxides Chemical class 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 8
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 4
229930182830 galactose Natural products 0.000 claims 3
150000002256 galaktoses Chemical class 0.000 claims 3
150000002303 glucose derivatives Chemical class 0.000 claims 3
KEJGAYKWRDILTF-JDDHQFAOSA-N (3ar,5s,6s,6ar)-5-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol Chemical compound O1C(C)(C)OC[C@@H]1[C@@H]1[C@H](O)[C@H]2OC(C)(C)O[C@H]2O1 KEJGAYKWRDILTF-JDDHQFAOSA-N 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
239000012024 dehydrating agents‎ Substances 0.000 claims 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 35
150000003839 salts Chemical group 0.000 abstract description 10
150000001412 amines Chemical class 0.000 abstract description 9
241001465754 Metazoa Species 0.000 abstract description 6
230000000840 anti-viral effect Effects 0.000 abstract description 5
239000006227 byproduct Substances 0.000 abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
239000003921 oil Substances 0.000 description 25
235000019198 oils Nutrition 0.000 description 25
239000000047 product Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 16
230000003287 optical effect Effects 0.000 description 15
241000700605 Viruses Species 0.000 description 14
238000004817 gas chromatography Methods 0.000 description 14
239000000376 reactant Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000009835 boiling Methods 0.000 description 10
201000010099 disease Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229960001701 chloroform Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
229940079593 drug Drugs 0.000 description 8
AVVWPBAENSWJCB-IVMDWMLBSA-N D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-IVMDWMLBSA-N 0.000 description 7
239000007789 gas Substances 0.000 description 7
210000004072 lung Anatomy 0.000 description 7
239000002243 precursor Substances 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
241000709661 Enterovirus Species 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011707 mineral Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229940032330 sulfuric acid Drugs 0.000 description 6
239000000725 suspension Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
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 description 5
210000004027 cell Anatomy 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
229930195735 unsaturated hydrocarbon Natural products 0.000 description 5
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 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
241000991587 Enterovirus C Species 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
238000010420 art technique Methods 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
206010022000 influenza Diseases 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
229930195734 saturated hydrocarbon Natural products 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
238000006959 Williamson synthesis reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical class [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
239000011324 bead Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
230000000120 cytopathologic effect Effects 0.000 description 3
230000008034 disappearance Effects 0.000 description 3
230000000857 drug effect Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012535 impurity Substances 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000002054 inoculum Substances 0.000 description 3
231100001160 nonlethal Toxicity 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000002245 particle Substances 0.000 description 3
150000003214 pyranose derivatives Chemical class 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
230000001629 suppression Effects 0.000 description 3
OCWGRWAYARCRTQ-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CC(Cl)CN(C)C OCWGRWAYARCRTQ-UHFFFAOYSA-N 0.000 description 2
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
241000710188 Encephalomyocarditis virus Species 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000003443 antiviral agent Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000005779 cell damage Effects 0.000 description 2
208000037887 cell injury Diseases 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
238000007429 general method Methods 0.000 description 2
208000037797 influenza A Diseases 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
230000007505 plaque formation Effects 0.000 description 2
238000012545 processing Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
241000712461 unidentified influenza virus Species 0.000 description 2
238000005406 washing Methods 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
GLCIWWDTRSPYRQ-VARJHODCSA-N (3R,4R,5S)-5-[(1S)-1,2-dihydroxypent-2-enyl]oxolane-2,3,4-triol Chemical compound CCC=C(O)[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O GLCIWWDTRSPYRQ-VARJHODCSA-N 0.000 description 1
DFMFZTRATASQTP-VARJHODCSA-N (3r,4r,5s)-5-[(1s)-1,2-dihydroxy-3-methylbut-2-enyl]oxolane-2,3,4-triol Chemical compound CC(C)=C(O)[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O DFMFZTRATASQTP-VARJHODCSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
FSNGFFWICFYWQC-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine;hydron;chloride Chemical compound Cl.ClCCN1CCCC1 FSNGFFWICFYWQC-UHFFFAOYSA-N 0.000 description 1
KCQMALZNENFGKK-UHFFFAOYSA-N 2-(2-chloroethyl)-1-methylpyrrolidine;hydron;chloride Chemical compound Cl.CN1CCCC1CCCl KCQMALZNENFGKK-UHFFFAOYSA-N 0.000 description 1
ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
WGPZPQXUPCXORP-UHFFFAOYSA-N 2-chloro-3,3-dimethylbutan-2-amine Chemical compound CC(C)(C)C(C)(N)Cl WGPZPQXUPCXORP-UHFFFAOYSA-N 0.000 description 1
RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 description 1
QDOJNWFOCOWAPO-UHFFFAOYSA-N 4-chloro-1-methylpiperidine;hydron;chloride Chemical compound Cl.CN1CCC(Cl)CC1 QDOJNWFOCOWAPO-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
IPBUERDNRWYKON-UHFFFAOYSA-N 5-chloro-n,n-dimethylpentan-1-amine;hydrochloride Chemical compound Cl.CN(C)CCCCCCl IPBUERDNRWYKON-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
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 description 1
WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 1
WQZGKKKJIJFFOK-RSVSWTKNSA-N D-altro-hexose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-RSVSWTKNSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
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 1
241000450599 DNA viruses Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
208000032843 Hemorrhage Diseases 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
241000264060 Lethrinus Species 0.000 description 1
208000005647 Mumps Diseases 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
108010019160 Pancreatin Proteins 0.000 description 1
208000000474 Poliomyelitis Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
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 description 1
GZCGUPFRVQAUEE-KAZBKCHUSA-N aldehydo-D-talose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KAZBKCHUSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
210000004102 animal cell Anatomy 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001723 carbon free-radicals Chemical class 0.000 description 1
150000005323 carbonate salts Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 1
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000007596 consolidation process Methods 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
210000004748 cultured cell Anatomy 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000001035 drying Methods 0.000 description 1
241001493065 dsRNA viruses Species 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
229940097043 glucuronic acid Drugs 0.000 description 1
230000035931 haemagglutination Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
210000003292 kidney cell Anatomy 0.000 description 1
230000002147 killing effect Effects 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960000448 lactic acid Drugs 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
208000010805 mumps infectious disease Diseases 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
229940116315 oxalic acid Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229940055695 pancreatin Drugs 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
- 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
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Materials Engineering (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Crystallography & Structural Chemistry (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA248,641A 1975-03-28 1976-03-24 Preparation d'ethers de monosaccharides Expired CA1068688A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/563,080 US4056322A (en)	1973-12-14	1975-03-28	Preparation of ethers of monosaccharides

Publications (1)

Publication Number	Publication Date
CA1068688A true CA1068688A (fr)	1979-12-25

Family

ID=24249032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA248,641A Expired CA1068688A (fr)	1975-03-28	1976-03-24	Preparation d'ethers de monosaccharides

Country Status (11)

Country	Link
JP (1)	JPS51118714A (fr)
AU (1)	AU1227276A (fr)
BE (1)	BE840091A (fr)
CA (1)	CA1068688A (fr)
CH (1)	CH623060A5 (fr)
DD (1)	DD126039A5 (fr)
DE (1)	DE2612717A1 (fr)
FR (1)	FR2305442A2 (fr)
GB (1)	GB1545831A (fr)
IT (1)	IT1058702B (fr)
SE (1)	SE7603682L (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK17685D0 (da) *	1985-01-14	1985-01-14	Hans Goeran Magnusson	Glycosidderivater
US20020165168A1 (en) *	1995-12-16	2002-11-07	Joachim Bunger	Use of sugar derivatives as antimicrobial, antimycotic and/or antiviral active substances
JP6055293B2 (ja) *	2012-11-27	2016-12-27	公益財団法人野口研究所	エーテル化合物製造法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1493710A1 (de) *	1965-05-08	1969-06-04	Bayer Ag	Verfahren zur Herstellung von niedrigmolekularen Glycidylaethern mehrwertiger Phenole
DE1793336C3 (de) *	1967-09-11	1974-10-03	Ciba-Geigy Ag, Basel (Schweiz)	D-Glucofuranoside, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
JPS5118195B2 (fr) *	1972-06-19	1976-06-08
US3939145A (en) *	1973-03-01	1976-02-17	Strategic Medical Research Corporation	Novel ethereally monosubstituted monosaccharides
IN141230B (fr) *	1973-12-14	1977-02-05	Strategic Medical Res Corp

1976
- 1976-03-23 AU AU12272/76A patent/AU1227276A/en not_active Expired
- 1976-03-24 CA CA248,641A patent/CA1068688A/fr not_active Expired
- 1976-03-25 DE DE19762612717 patent/DE2612717A1/de active Pending
- 1976-03-26 CH CH383476A patent/CH623060A5/fr not_active IP Right Cessation
- 1976-03-26 SE SE7603682A patent/SE7603682L/xx unknown
- 1976-03-26 DD DD192076A patent/DD126039A5/xx unknown
- 1976-03-26 BE BE165610A patent/BE840091A/fr unknown
- 1976-03-26 GB GB12262/76A patent/GB1545831A/en not_active Expired
- 1976-03-26 FR FR7608919A patent/FR2305442A2/fr active Pending
- 1976-03-29 JP JP51033700A patent/JPS51118714A/ja active Pending
- 1976-03-29 IT IT21696/76A patent/IT1058702B/it active

Also Published As

Publication number	Publication date
FR2305442A2 (fr)	1976-10-22
DD126039A5 (fr)	1977-06-15
IT1058702B (it)	1982-05-10
DE2612717A1 (de)	1976-10-14
GB1545831A (en)	1979-05-16
AU1227276A (en)	1977-09-29
SE7603682L (sv)	1976-09-29
CH623060A5 (en)	1981-05-15
BE840091A (fr)	1976-09-27
JPS51118714A (en)	1976-10-18

Publication	Publication Date	Title
US4056322A (en)	1977-11-01	Preparation of ethers of monosaccharides
US4017608A (en)	1977-04-12	Therapeutic composition and method of therapeutically treating warm blooded animals therewith
US4395405A (en)	1983-07-26	Alkyl-ketohexopyranoside derivatives and method of use
USRE32268E (en)	1986-10-21	Therapeutic composition and method of therapeutically treating warm blooded animals therewith
DE2409654A1 (de)	1974-09-12	Therapeutisches mittel
CA1068688A (fr)	1979-12-25	Preparation d'ethers de monosaccharides
CA1047032A (fr)	1979-01-23	Esters d'adriamycine
EP0051280B1 (fr)	1984-07-11	Dérivés glycosidiques d'anthracyclines, méthode pour leur préparation, dérivés intermédiaires et leur préparation et compositions pharmaceutiques
US4016261A (en)	1977-04-05	Therapeutic composition and method of therapeutically treating warm blooded animals therewith
US3939146A (en)	1976-02-17	Novel ethereal monosubstitutions of monosaccharide derivatives
CA2132303A1 (fr)	1993-09-30	Derives antiviraux de type acide phosphonique tires d'analogues de la purine
CA1269369A (fr)	1990-05-22	Derives du complexe 13-384 oligosaccharide- antibiotique, procede de preparation et composes pharmaceutiques les contenant
JP2519205B2 (ja)	1996-07-31	全−シス−１，３，５−トリアミノ−２，４，６−シクロヘキサントリオ−ル誘導体
JP2806621B2 (ja)	1998-09-30	新規アントラサイクリン類及びその製造方法
USRE30379E (en)	1980-08-19	Ethereal monosubstitutions of monosaccharide derivatives
USRE30354E (en)	1980-07-29	Novel ethereally monosubstituted monosaccharides
GB2067989A (en)	1981-08-05	Bis-moranoline derivatives
JP3170280B2 (ja)	2001-05-28	新規かつ改良されたエーテル性置換保護モノサッカライドの溶媒不在合成方法およびそれらの選択的加水分解
EP0089678B1 (fr)	1986-09-24	Dérivés de 2-béta-D-ribofuranosylsélénazole-4-carboxamide et méthodes pour leur production
USRE33000E (en)	1989-07-25	Therapeutic composition and method of treating viruses
PL77035B1 (fr)	1975-02-28
DE2455026A1 (de)	1975-07-03	Therapeutisches mittel
Miljković et al.	1984	Removal of sugar dithioacetal group with N-bromosuccinimide
US5753695A (en)	1998-05-19	Flavilium compounds and method of using
EP0474358A2 (fr)	1992-03-11	Utilisation de conduritol pour l'inhibition d'une augmentation du taux de sucre dans le sang