JP6057300B2 - グリコスフィンゴ脂質の調製及びその使用の方法 - Google Patents
グリコスフィンゴ脂質の調製及びその使用の方法 Download PDFInfo
- Publication number
- JP6057300B2 JP6057300B2 JP2013548554A JP2013548554A JP6057300B2 JP 6057300 B2 JP6057300 B2 JP 6057300B2 JP 2013548554 A JP2013548554 A JP 2013548554A JP 2013548554 A JP2013548554 A JP 2013548554A JP 6057300 B2 JP6057300 B2 JP 6057300B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mmol
- formula
- nmr
- synthesis
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 68
- 150000002339 glycosphingolipids Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 138
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 63
- 230000008569 process Effects 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003550 alpha-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- 238000006722 reduction reaction Methods 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 229910000085 borane Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 134
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- 238000003786 synthesis reaction Methods 0.000 description 99
- 230000015572 biosynthetic process Effects 0.000 description 96
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 238000005160 1H NMR spectroscopy Methods 0.000 description 53
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 50
- 239000011734 sodium Substances 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 43
- 239000000243 solution Substances 0.000 description 32
- 239000007858 starting material Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- AYNYHSGJYJNQKG-UHFFFAOYSA-N octadecane-1,3,4-triol Chemical compound CCCCCCCCCCCCCCC(O)C(O)CCO AYNYHSGJYJNQKG-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 108090000695 Cytokines Proteins 0.000 description 10
- 102000004127 Cytokines Human genes 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000028327 secretion Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 150000001540 azides Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 8
- 229940045860 white wax Drugs 0.000 description 8
- MBBYHWZVGHKEBI-UHFFFAOYSA-N 9-carboxynonyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCC(=O)O)C1=CC=CC=C1 MBBYHWZVGHKEBI-UHFFFAOYSA-N 0.000 description 7
- 229930186217 Glycolipid Natural products 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 210000000612 antigen-presenting cell Anatomy 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 210000000581 natural killer T-cell Anatomy 0.000 description 6
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- VQFKFAKEUMHBLV-BYSUZVQFSA-N 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQFKFAKEUMHBLV-BYSUZVQFSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 5
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 125000003147 glycosyl group Chemical group 0.000 description 5
- 230000013595 glycosylation Effects 0.000 description 5
- 238000006206 glycosylation reaction Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 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 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- AERBNCYCJBRYDG-UHFFFAOYSA-N D-ribo-phytosphingosine Natural products CCCCCCCCCCCCCCC(O)C(O)C(N)CO AERBNCYCJBRYDG-UHFFFAOYSA-N 0.000 description 4
- 102100037850 Interferon gamma Human genes 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
- 229940073608 benzyl chloride Drugs 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 230000003308 immunostimulating effect Effects 0.000 description 4
- AERBNCYCJBRYDG-KSZLIROESA-N phytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO AERBNCYCJBRYDG-KSZLIROESA-N 0.000 description 4
- 229940033329 phytosphingosine Drugs 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- CZCPLBIEDAVFKO-UHFFFAOYSA-N 11-(2,4-dichlorophenyl)undecanoic acid Chemical compound OC(=O)CCCCCCCCCCC1=CC=C(Cl)C=C1Cl CZCPLBIEDAVFKO-UHFFFAOYSA-N 0.000 description 3
- HOGYTBYZCRYXBG-UHFFFAOYSA-N 11-(2,4-difluorophenyl)undecanoic acid Chemical compound OC(=O)CCCCCCCCCCC1=CC=C(F)C=C1F HOGYTBYZCRYXBG-UHFFFAOYSA-N 0.000 description 3
- UQXVIUIQASQCLO-UHFFFAOYSA-N 2-(3,4-difluorophenyl)undecanoic acid Chemical compound CCCCCCCCCC(C(O)=O)C1=CC=C(F)C(F)=C1 UQXVIUIQASQCLO-UHFFFAOYSA-N 0.000 description 3
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108010074328 Interferon-gamma Proteins 0.000 description 3
- 108090000978 Interleukin-4 Proteins 0.000 description 3
- 108700018351 Major Histocompatibility Complex Proteins 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000005574 benzylation reaction Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012636 effector Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000002955 immunomodulating agent Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 3
- 239000012285 osmium tetroxide Substances 0.000 description 3
- 229940035671 phytosphingosine hydrochloride Drugs 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 230000020382 suppression by virus of host antigen processing and presentation of peptide antigen via MHC class I Effects 0.000 description 3
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 230000035899 viability Effects 0.000 description 3
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- GDKAAHDFPOWGQE-RXQQAGQTSA-N (2s,3s,4r)-2-aminooctadecane-1,3,4-triol;hydrochloride Chemical compound Cl.CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO GDKAAHDFPOWGQE-RXQQAGQTSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- SBXDJEMFYDWIEO-UHFFFAOYSA-N 11-(4-bromophenyl)-10,11-dihydroxyundecanoic acid Chemical compound OC(=O)CCCCCCCCC(O)C(O)C1=CC=C(Br)C=C1 SBXDJEMFYDWIEO-UHFFFAOYSA-N 0.000 description 2
- PRVHNIHTBLVKPO-UHFFFAOYSA-N 11-(4-bromophenyl)undecanoic acid Chemical compound OC(=O)CCCCCCCCCCC1=CC=C(Br)C=C1 PRVHNIHTBLVKPO-UHFFFAOYSA-N 0.000 description 2
- RNZZJNGFDUVKFG-UHFFFAOYSA-N 11-(4-chlorophenyl)undecanoic acid Chemical compound OC(=O)CCCCCCCCCCC1=CC=C(Cl)C=C1 RNZZJNGFDUVKFG-UHFFFAOYSA-N 0.000 description 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical class OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- 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 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- YUPBWHURNLRZQL-UHFFFAOYSA-N 4-(4-fluorophenoxy)benzaldehyde Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=O)C=C1 YUPBWHURNLRZQL-UHFFFAOYSA-N 0.000 description 2
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 2
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 2
- INIZASNUANALJU-UHFFFAOYSA-N CCCCCCCCCCCCCCC(C(CC)(O)O)O Chemical compound CCCCCCCCCCCCCCC(C(CC)(O)O)O INIZASNUANALJU-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 108010002350 Interleukin-2 Proteins 0.000 description 2
- 102000000588 Interleukin-2 Human genes 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 241000508269 Psidium Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000010976 amide bond formation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229940106189 ceramide Drugs 0.000 description 2
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 230000016396 cytokine production Effects 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 210000004443 dendritic cell Anatomy 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 210000004988 splenocyte Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
- WRBLINBOCHHEKM-NVXWUHKLSA-N (10r,11r)-11-(3,4-difluorophenyl)-10,11-dihydroxyundecanoic acid Chemical compound OC(=O)CCCCCCCC[C@@H](O)[C@H](O)C1=CC=C(F)C(F)=C1 WRBLINBOCHHEKM-NVXWUHKLSA-N 0.000 description 1
- WRBLINBOCHHEKM-RDJZCZTQSA-N (10s,11s)-11-(3,4-difluorophenyl)-10,11-dihydroxyundecanoic acid Chemical compound OC(=O)CCCCCCCC[C@H](O)[C@@H](O)C1=CC=C(F)C(F)=C1 WRBLINBOCHHEKM-RDJZCZTQSA-N 0.000 description 1
- VBEACWDENQMGMX-GZILEVFKSA-N (2S,3S,4R)-2-aminooctadecane-1,3,4-triol hydrochloride Chemical compound Cl.CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO.CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO VBEACWDENQMGMX-GZILEVFKSA-N 0.000 description 1
- YBADLXQNJCMBKR-UHFFFAOYSA-N (4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-N 0.000 description 1
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- PGVRSPIEZYGOAD-UHFFFAOYSA-N 10-bromodecanoic acid Chemical compound OC(=O)CCCCCCCCCBr PGVRSPIEZYGOAD-UHFFFAOYSA-N 0.000 description 1
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 1
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- WCGPCBACLBHDCI-UHFFFAOYSA-N 2,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(F)=C1 WCGPCBACLBHDCI-UHFFFAOYSA-N 0.000 description 1
- KCNISYPADDTFDO-UHFFFAOYSA-N 2,4-dinitrophenylacetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O KCNISYPADDTFDO-UHFFFAOYSA-N 0.000 description 1
- RZWGTXHSYZGXKF-UHFFFAOYSA-N 2-(2-methylphenyl)acetic acid Chemical compound CC1=CC=CC=C1CC(O)=O RZWGTXHSYZGXKF-UHFFFAOYSA-N 0.000 description 1
- YCAKYFIYUHHCKW-UHFFFAOYSA-N 2-(3,4-difluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C(F)=C1 YCAKYFIYUHHCKW-UHFFFAOYSA-N 0.000 description 1
- GXXXUZIRGXYDFP-UHFFFAOYSA-N 2-(4-methylphenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-N 0.000 description 1
- RSOHOXHNJIONSL-UHFFFAOYSA-N 2-(4-tert-butylphenyl)acetamide Chemical compound CC(C)(C)C1=CC=C(CC(N)=O)C=C1 RSOHOXHNJIONSL-UHFFFAOYSA-N 0.000 description 1
- RUAYXHSDAMWEDR-UHFFFAOYSA-N 2-(4-tert-butylphenyl)acetic acid Chemical compound CC(C)(C)C1=CC=C(CC(O)=O)C=C1 RUAYXHSDAMWEDR-UHFFFAOYSA-N 0.000 description 1
- ANWWCIFHSMVRKG-UHFFFAOYSA-N 2-[3,4-bis(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(C(F)(F)F)C(C(F)(F)F)=C1 ANWWCIFHSMVRKG-UHFFFAOYSA-N 0.000 description 1
- BLXXCCIBGGBDHI-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(F)(F)F)=C1 BLXXCCIBGGBDHI-UHFFFAOYSA-N 0.000 description 1
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- VIBOGIYPPWLDTI-UHFFFAOYSA-N 2-naphthylacetic acid Chemical compound C1=CC=CC2=CC(CC(=O)O)=CC=C21 VIBOGIYPPWLDTI-UHFFFAOYSA-N 0.000 description 1
- JPHKMYXKNKLNDF-UHFFFAOYSA-N 3,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1F JPHKMYXKNKLNDF-UHFFFAOYSA-N 0.000 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical compound OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- QWLHJVDRPZNVBS-UHFFFAOYSA-N 4-phenoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OC1=CC=CC=C1 QWLHJVDRPZNVBS-UHFFFAOYSA-N 0.000 description 1
- LEPWUMPXISBPIB-UHFFFAOYSA-N 4-phenylbutanamide Chemical compound NC(=O)CCCC1=CC=CC=C1 LEPWUMPXISBPIB-UHFFFAOYSA-N 0.000 description 1
- WDANSDASCKBVKH-UHFFFAOYSA-N 4-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=C(C=O)C=C1 WDANSDASCKBVKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001251200 Agelas Species 0.000 description 1
- 102000006306 Antigen Receptors Human genes 0.000 description 1
- 108010083359 Antigen Receptors Proteins 0.000 description 1
- 102100036013 Antigen-presenting glycoprotein CD1d Human genes 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 101000716121 Homo sapiens Antigen-presenting glycoprotein CD1d Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 101001044384 Mus musculus Interferon gamma Proteins 0.000 description 1
- 101001043827 Mus musculus Interleukin-2 Proteins 0.000 description 1
- 101001002703 Mus musculus Interleukin-4 Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000243142 Porifera Species 0.000 description 1
- 229930182475 S-glycoside Natural products 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000003428 Staudinger Azide reduction reaction Methods 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000004721 adaptive immunity Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940107161 cholesterol Drugs 0.000 description 1
- 230000004186 co-expression Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000833 heterodimer Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 230000004073 interleukin-2 production Effects 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 210000000207 lymphocyte subset Anatomy 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CLOXAWYNXXEWBT-UHFFFAOYSA-N tert-butyl n-(3-oxocyclopentyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(=O)C1 CLOXAWYNXXEWBT-UHFFFAOYSA-N 0.000 description 1
- QBJZBHSUMZGEFY-UHFFFAOYSA-N tert-butylcarbamic acid;carbamic acid Chemical compound NC(O)=O.CC(C)(C)NC(O)=O QBJZBHSUMZGEFY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003569 thioglycosides Chemical class 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty 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
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Epidemiology (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161430117P | 2011-01-05 | 2011-01-05 | |
| US61/430,117 | 2011-01-05 | ||
| PCT/US2012/020388 WO2012094540A2 (en) | 2011-01-05 | 2012-01-05 | Methods for preparation of glycosphingolipids and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016209071A Division JP6259887B2 (ja) | 2011-01-05 | 2016-10-25 | グリコスフィンゴ脂質の調製及びその使用の方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014504593A JP2014504593A (ja) | 2014-02-24 |
| JP2014504593A5 JP2014504593A5 (enExample) | 2015-02-19 |
| JP6057300B2 true JP6057300B2 (ja) | 2017-01-11 |
Family
ID=45688966
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013548554A Active JP6057300B2 (ja) | 2011-01-05 | 2012-01-05 | グリコスフィンゴ脂質の調製及びその使用の方法 |
| JP2016209071A Active JP6259887B2 (ja) | 2011-01-05 | 2016-10-25 | グリコスフィンゴ脂質の調製及びその使用の方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016209071A Active JP6259887B2 (ja) | 2011-01-05 | 2016-10-25 | グリコスフィンゴ脂質の調製及びその使用の方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US9181292B2 (enExample) |
| EP (1) | EP2661440B1 (enExample) |
| JP (2) | JP6057300B2 (enExample) |
| KR (1) | KR102005003B1 (enExample) |
| CN (1) | CN103748103A (enExample) |
| AU (2) | AU2012204336C1 (enExample) |
| BR (1) | BR112013017382B1 (enExample) |
| CA (1) | CA2854725C (enExample) |
| CO (1) | CO6761397A2 (enExample) |
| ES (1) | ES2654382T3 (enExample) |
| HK (1) | HK1197068A1 (enExample) |
| IL (1) | IL227333B (enExample) |
| MX (1) | MX345764B (enExample) |
| RU (1) | RU2636587C2 (enExample) |
| WO (1) | WO2012094540A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017061481A (ja) * | 2011-01-05 | 2017-03-30 | ナショナル タイワン ユニバーシティ | グリコスフィンゴ脂質の調製及びその使用の方法 |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7960139B2 (en) | 2007-03-23 | 2011-06-14 | Academia Sinica | Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells |
| JP5986745B2 (ja) | 2008-07-15 | 2016-09-06 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | Ｐｔｆｅ様のアルミニウム・コート・ガラススライド上のグリカンアレイおよび関連する方法 |
| US11377485B2 (en) | 2009-12-02 | 2022-07-05 | Academia Sinica | Methods for modifying human antibodies by glycan engineering |
| US10087236B2 (en) | 2009-12-02 | 2018-10-02 | Academia Sinica | Methods for modifying human antibodies by glycan engineering |
| US10338069B2 (en) | 2010-04-12 | 2019-07-02 | Academia Sinica | Glycan arrays for high throughput screening of viruses |
| AU2011250970B2 (en) | 2010-05-10 | 2016-12-15 | Sinica, Academia | Zanamivir phosphonate congeners with anti-influenza activity and determining oseltamivir susceptibility of influenza viruses |
| US10227290B2 (en) * | 2012-02-07 | 2019-03-12 | The Regents Of The University Of California | Glycosphingolipids for use in modulating immune responses |
| US10130714B2 (en) | 2012-04-14 | 2018-11-20 | Academia Sinica | Enhanced anti-influenza agents conjugated with anti-inflammatory activity |
| AU2013306098A1 (en) | 2012-08-18 | 2015-02-12 | Academia Sinica | Cell-permeable probes for identification and imaging of sialidases |
| US9547009B2 (en) | 2012-08-21 | 2017-01-17 | Academia Sinica | Benzocyclooctyne compounds and uses thereof |
| EP2727929A1 (en) * | 2012-10-30 | 2014-05-07 | Wittycell | Method of preparation of alpha galactosyl ceramides compounds |
| US10086054B2 (en) | 2013-06-26 | 2018-10-02 | Academia Sinica | RM2 antigens and use thereof |
| WO2014210564A1 (en) | 2013-06-27 | 2014-12-31 | Academia Sinica | Glycan conjugates and use thereof |
| AU2014317889B2 (en) * | 2013-09-06 | 2020-03-05 | Academia Sinica | Human iNKT cell activation using glycolipids with altered glycosyl groups |
| TW201620939A (zh) | 2014-01-16 | 2016-06-16 | 中央研究院 | 治療及檢測癌症之組合物及方法 |
| US10150818B2 (en) | 2014-01-16 | 2018-12-11 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| TWI687428B (zh) | 2014-03-27 | 2020-03-11 | 中央研究院 | 反應性標記化合物及其用途 |
| US10118969B2 (en) | 2014-05-27 | 2018-11-06 | Academia Sinica | Compositions and methods relating to universal glycoforms for enhanced antibody efficacy |
| AU2015267047A1 (en) | 2014-05-27 | 2017-01-05 | Academia Sinica | Anti-CD20 glycoantibodies and uses thereof |
| AU2015267051B2 (en) | 2014-05-27 | 2022-03-17 | Academia Sinica | Fucosidase from bacteroides and methods using the same |
| JP7062361B2 (ja) | 2014-05-27 | 2022-05-06 | アカデミア シニカ | 抗ｈｅｒ２糖操作抗体群およびその使用 |
| WO2015184001A1 (en) | 2014-05-28 | 2015-12-03 | Academia Sinica | Anti-tnf-alpha glycoantibodies and uses thereof |
| US9879042B2 (en) * | 2014-09-08 | 2018-01-30 | Academia Sinica | Human iNKT cell activation using glycolipids |
| US10495645B2 (en) | 2015-01-16 | 2019-12-03 | Academia Sinica | Cancer markers and methods of use thereof |
| US9975965B2 (en) | 2015-01-16 | 2018-05-22 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| AU2015378564A1 (en) | 2015-01-24 | 2017-07-13 | Academia Sinica | Novel glycan conjugates and methods of use thereof |
| WO2017083830A1 (en) * | 2015-11-13 | 2017-05-18 | La Jolla Institute For Allergy And Immunology | Sphingamide compounds and methods for binding inkt cells |
| EP3387447A4 (en) | 2015-12-11 | 2019-08-28 | Opko Diagnostics, LLC | FLUID SYSTEMS WITH INCUBATION SAMPLES AND / OR REAGENTS |
| EP3397387B1 (en) | 2015-12-29 | 2021-03-24 | Opko Diagnostics, LLC | Fluid collection device and related methods |
| CN109195996A (zh) | 2016-03-08 | 2019-01-11 | 中央研究院 | N-聚醣及其阵列的模组化合成方法 |
| KR102588027B1 (ko) | 2016-08-22 | 2023-10-12 | 초 파마 인크. | 항체, 결합 단편 및 사용 방법 |
| PT3681512T (pt) * | 2017-09-13 | 2021-10-06 | Abivax | Abx196 para uso no tratamento do cancro da bexiga |
| CN110835361A (zh) * | 2019-10-21 | 2020-02-25 | 山东大学 | 一类唾液酸糖基给体及其制备方法和应用 |
| WO2021142581A1 (zh) * | 2020-01-13 | 2021-07-22 | 郑州市御合源生物科技有限公司 | 一种糖苷化合物及其制备方法和应用 |
| EP4274541A1 (en) * | 2021-01-06 | 2023-11-15 | Evonik Operations GmbH | Hydroxy-substituted sphingolipids |
| CN114805454B (zh) * | 2021-01-21 | 2023-07-18 | 中国科学院生态环境研究中心 | α-半乳糖神经酰胺类化合物及其制备方法和用途 |
| AU2022228420A1 (en) | 2021-03-01 | 2023-10-05 | Deciduous Therapeutics, Inc. | Compounds for activating invariant natural killer t-cells and methods of use in eliminating inflammatory senescent cells |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0676429B2 (ja) | 1987-03-09 | 1994-09-28 | 理化学研究所 | ラクト系列スフィンゴ糖脂質の合成法 |
| JP2588729B2 (ja) * | 1987-10-05 | 1997-03-12 | 塩野義製薬株式会社 | スフィンゴシン誘導体 |
| AU683026B2 (en) | 1992-10-22 | 1997-10-30 | Kirin Pharma Kabushiki Kaisha | Novel shingoglycolipid and use thereof |
| CA2142153A1 (en) * | 1994-03-04 | 1995-09-05 | Jacques Banville | Sulfated .beta.-glycolipid derivatives as cell adhesion inhibitors |
| JPH11269189A (ja) * | 1998-03-19 | 1999-10-05 | Nissin Food Prod Co Ltd | 免疫調節作用を有する化合物 |
| CN1405172A (zh) | 2001-08-13 | 2003-03-26 | 青岛海洋大学 | 一种乳糖胺脂及其制备方法和应用 |
| DE10258007B4 (de) * | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
| WO2006037159A1 (en) | 2004-10-04 | 2006-04-13 | Alchemia Limited | Selective inhibitors |
| US7923013B2 (en) | 2004-12-28 | 2011-04-12 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NKT cells |
| JP5090928B2 (ja) | 2004-12-28 | 2012-12-05 | ザ ロックフェラー ユニバーシティ | Ｎｋｔ細胞に対する抗原としての糖脂質及びその類似体 |
| EP2390255B1 (en) * | 2006-04-03 | 2016-07-13 | Technion Research & Development Foundation Ltd. | Novel aminoglycosides and uses thereof in the treatment of genetic disorders |
| US8420607B2 (en) | 2006-06-30 | 2013-04-16 | University Of Georgia Research Foundation, Inc. | Anthrax carbohydrates, synthesis and uses thereof |
| CN101012254A (zh) | 2006-08-29 | 2007-08-08 | 中国海洋大学 | 一种α－半乳糖鞘糖脂的2’－OH衍生物及其制备方法 |
| KR100868959B1 (ko) * | 2006-12-30 | 2008-11-17 | 재단법인서울대학교산학협력재단 | 알파-갈락토실세라마이드 유도체, 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는면역보조용 약학적 조성물 |
| EP2144594A4 (en) | 2007-04-13 | 2012-12-05 | Academia Sinica | ALPHA-GALACTOSYL CERAMIDE ANALOGUES AND THEIR USE IN IMMUNOTHERAPIES |
| US20090137793A1 (en) | 2007-11-19 | 2009-05-28 | Academia Sinica | Disaccharide compounds |
| CN102066393B (zh) | 2008-05-16 | 2014-07-02 | 格莱克特生物技术公司 | 半乳糖苷抑制剂的合成 |
| US7928077B2 (en) | 2008-07-11 | 2011-04-19 | Academia Sinica | Alpha-galactosyl ceramide analogs and their use as immunotherapies |
| ES2654382T3 (es) | 2011-01-05 | 2018-02-13 | National Taiwan University | Método para la preparación de glucoesfingolípidos |
-
2012
- 2012-01-05 ES ES12704939.3T patent/ES2654382T3/es active Active
- 2012-01-05 HK HK14110574.7A patent/HK1197068A1/xx unknown
- 2012-01-05 BR BR112013017382-3A patent/BR112013017382B1/pt active IP Right Grant
- 2012-01-05 AU AU2012204336A patent/AU2012204336C1/en active Active
- 2012-01-05 WO PCT/US2012/020388 patent/WO2012094540A2/en not_active Ceased
- 2012-01-05 EP EP12704939.3A patent/EP2661440B1/en active Active
- 2012-01-05 JP JP2013548554A patent/JP6057300B2/ja active Active
- 2012-01-05 MX MX2013007888A patent/MX345764B/es active IP Right Grant
- 2012-01-05 CN CN201280011839.4A patent/CN103748103A/zh active Pending
- 2012-01-05 US US13/344,557 patent/US9181292B2/en active Active
- 2012-01-05 CA CA2854725A patent/CA2854725C/en active Active
- 2012-01-05 RU RU2013136531A patent/RU2636587C2/ru active
- 2012-01-05 KR KR1020137020635A patent/KR102005003B1/ko active Active
-
2013
- 2013-07-04 IL IL227333A patent/IL227333B/en active IP Right Grant
- 2013-07-05 CO CO13159964A patent/CO6761397A2/es unknown
-
2015
- 2015-10-07 US US14/877,897 patent/US10654880B2/en active Active
-
2016
- 2016-10-25 JP JP2016209071A patent/JP6259887B2/ja active Active
-
2017
- 2017-07-21 AU AU2017206277A patent/AU2017206277B2/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017061481A (ja) * | 2011-01-05 | 2017-03-30 | ナショナル タイワン ユニバーシティ | グリコスフィンゴ脂質の調製及びその使用の方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US9181292B2 (en) | 2015-11-10 |
| AU2012204336C1 (en) | 2017-08-03 |
| JP6259887B2 (ja) | 2018-01-10 |
| IL227333A0 (en) | 2013-09-30 |
| US10654880B2 (en) | 2020-05-19 |
| KR102005003B1 (ko) | 2019-07-29 |
| AU2012204336A1 (en) | 2013-08-22 |
| BR112013017382A2 (pt) | 2016-10-04 |
| US20120178705A1 (en) | 2012-07-12 |
| MX2013007888A (es) | 2014-09-11 |
| AU2012204336B2 (en) | 2017-05-04 |
| CN103748103A (zh) | 2014-04-23 |
| EP2661440A2 (en) | 2013-11-13 |
| KR20140036147A (ko) | 2014-03-25 |
| AU2017206277B2 (en) | 2019-05-02 |
| CA2854725A1 (en) | 2013-07-12 |
| RU2013136531A (ru) | 2015-02-10 |
| US20160229881A1 (en) | 2016-08-11 |
| WO2012094540A2 (en) | 2012-07-12 |
| EP2661440B1 (en) | 2017-09-27 |
| RU2636587C2 (ru) | 2017-11-24 |
| WO2012094540A3 (en) | 2012-08-30 |
| BR112013017382B1 (pt) | 2021-03-16 |
| JP2017061481A (ja) | 2017-03-30 |
| IL227333B (en) | 2018-01-31 |
| CO6761397A2 (es) | 2013-09-30 |
| AU2017206277A1 (en) | 2017-08-10 |
| ES2654382T3 (es) | 2018-02-13 |
| MX345764B (es) | 2017-02-15 |
| CA2854725C (en) | 2019-10-22 |
| JP2014504593A (ja) | 2014-02-24 |
| HK1197068A1 (en) | 2015-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6259887B2 (ja) | グリコスフィンゴ脂質の調製及びその使用の方法 | |
| JP3717512B2 (ja) | 新規スフィンゴ糖脂質およびその使用 | |
| JP5090928B2 (ja) | Ｎｋｔ細胞に対する抗原としての糖脂質及びその類似体 | |
| CN102816189B (zh) | α-半乳糖神经酰胺衍生物、其药物可接受的盐、制备方法和含有其作为活性成分的用于免疫佐剂的药物组合物 | |
| US8551959B2 (en) | Glycolipid and use thereof | |
| US8163290B2 (en) | Glycolipids and analogues thereof as antigens for NKT cells | |
| EP2877481B1 (en) | Organic compounds | |
| TWI595878B (zh) | 製備鞘糖脂之方法及其用途 | |
| Murphy et al. | R-Galactosylceramides and analogues− Important immunomodulators for use as vaccine adjuvants | |
| JP3800434B2 (ja) | 擬似糖脂質 | |
| NZ613614B2 (en) | Sphingoglycolipid compounds and uses |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141224 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20141225 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20151224 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160304 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160624 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20160624 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160929 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20161026 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20161129 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6057300 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |