DD295854A5 - Lipid-a-austauschstoffe mit immunoaktivierender und antitumorwirkung - Google Patents
Lipid-a-austauschstoffe mit immunoaktivierender und antitumorwirkung Download PDFInfo
- Publication number
- DD295854A5 DD295854A5 DD90342041A DD34204190A DD295854A5 DD 295854 A5 DD295854 A5 DD 295854A5 DD 90342041 A DD90342041 A DD 90342041A DD 34204190 A DD34204190 A DD 34204190A DD 295854 A5 DD295854 A5 DD 295854A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- carbon atoms
- groups
- substituted
- hydroxy
- Prior art date
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- 230000000259 anti-tumor effect Effects 0.000 title description 2
- -1 phosphoryl group Chemical group 0.000 claims abstract description 860
- 150000001875 compounds Chemical class 0.000 claims abstract description 361
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 131
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 86
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 238000003745 diagnosis Methods 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 238000011321 prophylaxis Methods 0.000 claims abstract description 8
- 210000000987 immune system Anatomy 0.000 claims abstract description 7
- 201000010099 disease Diseases 0.000 claims abstract description 4
- 208000035475 disorder Diseases 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 234
- 239000000203 mixture Substances 0.000 claims description 174
- 238000006243 chemical reaction Methods 0.000 claims description 173
- 125000001931 aliphatic group Chemical group 0.000 claims description 137
- 125000001424 substituent group Chemical group 0.000 claims description 133
- 125000005843 halogen group Chemical group 0.000 claims description 78
- 125000002252 acyl group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 239000003153 chemical reaction reagent Substances 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000001589 carboacyl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- 125000001153 fluoro group Chemical group F* 0.000 claims description 34
- 229910019142 PO4 Inorganic materials 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 239000010452 phosphate Substances 0.000 claims description 31
- 125000006239 protecting group Chemical group 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 230000007547 defect Effects 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 238000009938 salting Methods 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 25
- 239000011737 fluorine Substances 0.000 abstract description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 6
- 241001465754 Metazoa Species 0.000 abstract description 6
- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 150000002632 lipids Chemical class 0.000 abstract description 3
- 230000026731 phosphorylation Effects 0.000 abstract description 3
- 238000006366 phosphorylation reaction Methods 0.000 abstract description 3
- 210000002925 A-like Anatomy 0.000 abstract description 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 230000007812 deficiency Effects 0.000 abstract 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 201
- 239000000243 solution Substances 0.000 description 121
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
- 238000000862 absorption spectrum Methods 0.000 description 93
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 90
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 60
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 59
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- 238000004458 analytical method Methods 0.000 description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
- 229920006395 saturated elastomer Polymers 0.000 description 47
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 46
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 42
- 239000003480 eluent Substances 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 38
- 238000004440 column chromatography Methods 0.000 description 37
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
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- 239000007864 aqueous solution Substances 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
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- 229910052739 hydrogen Inorganic materials 0.000 description 22
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- 239000003054 catalyst Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 20
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
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- 230000035484 reaction time Effects 0.000 description 12
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
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- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 9
- 238000010531 catalytic reduction reaction Methods 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
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- 229910052794 bromium Inorganic materials 0.000 description 8
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- 238000002143 fast-atom bombardment mass spectrum Methods 0.000 description 8
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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- OAXNNMJBIUHKBG-XCFPRLNISA-N [(2r,3r,4r,5r)-5,6-dihydroxy-2-[[(3r)-3-hydroxytetradecanoyl]amino]-1-oxo-4-phosphonooxyhexan-3-yl] (3r)-3-tetradecanoyloxytetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]([C@H](OP(O)(O)=O)[C@H](O)CO)[C@H](C=O)NC(=O)C[C@H](O)CCCCCCCCCCC OAXNNMJBIUHKBG-XCFPRLNISA-N 0.000 description 6
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000628 margaroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical group SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RXXXGJINTARBNA-UHFFFAOYSA-N n-ethyl-n-(trichloro-$l^{4}-sulfanyl)ethanamine Chemical compound CCN(CC)S(Cl)(Cl)Cl RXXXGJINTARBNA-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
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- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
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- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
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- 230000002285 radioactive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- FEQPHYCEZKWPNE-UHFFFAOYSA-K trichlororhodium;triphenylphosphane Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FEQPHYCEZKWPNE-UHFFFAOYSA-K 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000004951 trihalomethoxy group Chemical group 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 231100000402 unacceptable toxicity Toxicity 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
-
- 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
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Fats And Perfumes (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1321153A JP2839921B2 (ja) | 1988-12-27 | 1989-12-11 | リピドａモノサッカライド類縁体 |
| JP3733990 | 1990-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD295854A5 true DD295854A5 (de) | 1991-11-14 |
Family
ID=26376476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90342041A DD295854A5 (de) | 1989-12-11 | 1990-06-25 | Lipid-a-austauschstoffe mit immunoaktivierender und antitumorwirkung |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5792840A (cs) |
| EP (1) | EP0437016B1 (cs) |
| KR (1) | KR0183315B1 (cs) |
| CN (1) | CN1029405C (cs) |
| AT (1) | ATE137504T1 (cs) |
| CA (1) | CA2019972C (cs) |
| CZ (1) | CZ285583B6 (cs) |
| DD (1) | DD295854A5 (cs) |
| DE (1) | DE69026808T2 (cs) |
| DK (1) | DK0437016T3 (cs) |
| ES (1) | ES2088970T3 (cs) |
| GR (1) | GR3020131T3 (cs) |
| HU (1) | HU217114B (cs) |
| IE (1) | IE74209B1 (cs) |
| PT (1) | PT94481B (cs) |
| RU (2) | RU1836378C (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0653434A1 (en) * | 1993-11-12 | 1995-05-17 | Tanabe Seiyaku Co., Ltd. | Glucosamine derivative, process for preparing the same and synthetic intermediate thereof |
| US5750664A (en) | 1995-06-05 | 1998-05-12 | Eisai Co., Ltd. | Substituted liposaccharides useful in the treatment and prevention of endotoxemia |
| US6368604B1 (en) | 1997-09-26 | 2002-04-09 | University Of Maryland Biotechnology Institute | Non-pyrogenic derivatives of lipid A |
| CN1372564A (zh) * | 2000-02-10 | 2002-10-02 | 三井化学株式会社 | 选择性制备1－磷酸化糖衍生物端基异构体的方法和制备核苷的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1984004526A1 (en) * | 1983-05-06 | 1984-11-22 | Wisconsin Alumni Res Found | Monosaccharide compounds having immunostimulating activity |
| GB2211503B (en) * | 1985-06-28 | 1990-01-31 | Sandoz Ltd | New saccharides, their preparation and pharmaceutical compositions containing them |
| NL8601551A (nl) * | 1985-06-28 | 1987-01-16 | Sandoz Ag | Nieuwe saccharides, hun bereiding en farmaceutische samenstellingen, die hen bevatten. |
| DE3731953A1 (de) * | 1987-09-23 | 1989-04-06 | Sandoz Ag | Neue saccharide, verfahren zu ihrer herstellung und ihre verwendung |
| US4746742A (en) * | 1985-11-28 | 1988-05-24 | Toho Yakuhin Kogyo Kabushiki Kaisha | Analogs of nonreducing monosaccharide moiety of lipid A |
| US4912094B1 (en) * | 1988-06-29 | 1994-02-15 | Ribi Immunochem Research Inc. | Modified lipopolysaccharides and process of preparation |
| DE3834377A1 (de) * | 1988-10-10 | 1990-04-12 | Medav Digitale Signalverarbeit | Verfahren zur automatischen erkennung und klassifizierung von digital quadratur-amplituden-modulierten signalen mit unbekannten parametern |
| DE3834877A1 (de) * | 1988-10-13 | 1990-05-03 | Sandoz Ag | Neue saccharide, verfahren zu ihrer herstellung und ihre verwendung |
-
1990
- 1990-06-25 RU SU904830600A patent/RU1836378C/ru active
- 1990-06-25 DD DD90342041A patent/DD295854A5/de not_active IP Right Cessation
- 1990-06-25 PT PT94481A patent/PT94481B/pt not_active IP Right Cessation
- 1990-06-26 CN CN90106805A patent/CN1029405C/zh not_active Expired - Fee Related
- 1990-06-26 HU HU903991A patent/HU217114B/hu not_active IP Right Cessation
- 1990-06-26 CZ CS903185A patent/CZ285583B6/cs not_active IP Right Cessation
- 1990-06-26 IE IE231290A patent/IE74209B1/en unknown
- 1990-06-27 AT AT90307045T patent/ATE137504T1/de not_active IP Right Cessation
- 1990-06-27 EP EP90307045A patent/EP0437016B1/en not_active Expired - Lifetime
- 1990-06-27 DE DE69026808T patent/DE69026808T2/de not_active Expired - Fee Related
- 1990-06-27 CA CA002019972A patent/CA2019972C/en not_active Expired - Fee Related
- 1990-06-27 DK DK90307045.6T patent/DK0437016T3/da active
- 1990-06-27 ES ES90307045T patent/ES2088970T3/es not_active Expired - Lifetime
-
1992
- 1992-09-09 RU SU925052656A patent/RU2076107C1/ru active
-
1994
- 1994-07-26 US US08/280,298 patent/US5792840A/en not_active Expired - Fee Related
-
1996
- 1996-05-31 GR GR960401511T patent/GR3020131T3/el unknown
-
1998
- 1998-09-11 KR KR1019980037538A patent/KR0183315B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HK1006312A1 (en) | 1999-02-19 |
| ATE137504T1 (de) | 1996-05-15 |
| ES2088970T3 (es) | 1996-10-01 |
| RU2076107C1 (ru) | 1997-03-27 |
| KR0183315B1 (ko) | 1999-04-01 |
| PT94481A (pt) | 1991-08-14 |
| CN1052481A (zh) | 1991-06-26 |
| CZ285583B6 (cs) | 1999-09-15 |
| CN1029405C (zh) | 1995-08-02 |
| EP0437016B1 (en) | 1996-05-01 |
| IE74209B1 (en) | 1997-07-16 |
| GR3020131T3 (en) | 1996-08-31 |
| PT94481B (pt) | 1997-02-28 |
| RU1836378C (ru) | 1993-08-23 |
| US5792840A (en) | 1998-08-11 |
| DK0437016T3 (da) | 1996-08-12 |
| IE902312A1 (en) | 1991-06-19 |
| EP0437016A2 (en) | 1991-07-17 |
| DE69026808T2 (de) | 1997-01-09 |
| CZ318590A3 (cs) | 1999-06-16 |
| CA2019972A1 (en) | 1991-06-11 |
| DE69026808D1 (de) | 1996-06-05 |
| HU217114B (hu) | 1999-11-29 |
| EP0437016A3 (en) | 1991-07-24 |
| CA2019972C (en) | 2000-08-08 |
| HUT55793A (en) | 1991-06-28 |
| HU903991D0 (en) | 1990-11-28 |
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| ENJ | Ceased due to non-payment of renewal fee |