CA2720771C - Triterpene saponins, methods of synthesis, and uses thereof - Google Patents
Triterpene saponins, methods of synthesis, and uses thereof Download PDFInfo
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- CA2720771C CA2720771C CA2720771A CA2720771A CA2720771C CA 2720771 C CA2720771 C CA 2720771C CA 2720771 A CA2720771 A CA 2720771A CA 2720771 A CA2720771 A CA 2720771A CA 2720771 C CA2720771 C CA 2720771C
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- 238000000034 method Methods 0.000 title claims description 49
- 238000003786 synthesis reaction Methods 0.000 title abstract description 14
- 230000015572 biosynthetic process Effects 0.000 title description 12
- 229930182493 triterpene saponin Natural products 0.000 title description 2
- -1 triterpene glycoside saponin Chemical class 0.000 claims abstract description 238
- 239000000203 mixture Substances 0.000 claims abstract description 102
- OILHVNROWDFZDW-UHFFFAOYSA-N prosapogenin Natural products CC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(CO)C(O)C(O)C6O)C(C)(C=O)C5CCC34C)C2C1)C(=O)O OILHVNROWDFZDW-UHFFFAOYSA-N 0.000 claims abstract description 59
- ZNFRITHWVZXJRK-UHFFFAOYSA-N Vitalboside A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OC(CO)C(O)C(O)C1O ZNFRITHWVZXJRK-UHFFFAOYSA-N 0.000 claims abstract description 13
- VTXFLUJNMHWAAT-UHFFFAOYSA-N alternoside VII Natural products CC1(C)CC(O)C2(CO)C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(C(O)C(OC7OC(CO)C(O)C(O)C7O)C6O)C(=O)O)C(C)(C)C5CCC34C)C2C1 VTXFLUJNMHWAAT-UHFFFAOYSA-N 0.000 claims abstract description 13
- IAGSHEHQJJTLLR-UHFFFAOYSA-N sapindoside B Natural products OC1C(C)OC(OC2C(OCC(O)C2O)OC2C(C3C(C4C(C5(CCC6(CCC(C)(C)CC6C5=CC4)C(O)=O)C)(C)CC3)(C)CC2)(C)CO)C(O)C1OC1OCC(O)C(O)C1O IAGSHEHQJJTLLR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 267
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 260
- 229910052757 nitrogen Inorganic materials 0.000 claims description 157
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 156
- 229910052760 oxygen Inorganic materials 0.000 claims description 125
- 239000001301 oxygen Substances 0.000 claims description 125
- 229910052717 sulfur Inorganic materials 0.000 claims description 125
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 124
- 239000011593 sulfur Substances 0.000 claims description 124
- 229910052739 hydrogen Inorganic materials 0.000 claims description 122
- 239000001257 hydrogen Substances 0.000 claims description 120
- 125000001931 aliphatic group Chemical group 0.000 claims description 110
- 125000005842 heteroatom Chemical group 0.000 claims description 108
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 55
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 54
- 125000006239 protecting group Chemical group 0.000 claims description 51
- 125000002252 acyl group Chemical group 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 150000001720 carbohydrates Chemical class 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 150000002148 esters Chemical class 0.000 claims description 38
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 23
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 150000001241 acetals Chemical class 0.000 claims description 20
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 20
- PIGTXFOGKFOFTO-UHFFFAOYSA-N prosapogenin Chemical compound C12CC(C)(C)CCC2(C(O)=O)C(O)CC(C2(CCC3C4(C=O)C)C)(C)C1=CCC2C3(C)CCC4OC1OC(C(O)=O)C(O)C(O)C1O PIGTXFOGKFOFTO-UHFFFAOYSA-N 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 18
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 18
- 229910052720 vanadium Inorganic materials 0.000 claims description 18
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 16
- 150000005215 alkyl ethers Chemical class 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 238000004587 chromatography analysis Methods 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000002015 acyclic group Chemical group 0.000 claims description 10
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 9
- 150000002170 ethers Chemical class 0.000 claims description 8
- 150000002243 furanoses Chemical class 0.000 claims description 8
- 229930182470 glycoside Natural products 0.000 claims description 8
- 150000003214 pyranose derivatives Chemical group 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- 150000002338 glycosides Chemical class 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 4
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 claims description 2
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 abstract description 76
- 229930182490 saponin Natural products 0.000 abstract description 44
- DRHZYJAUECRAJM-DWSYSWFDSA-N (2s,3s,4s,5r,6r)-6-[[(3s,4s,4ar,6ar,6bs,8r,8ar,12as,14ar,14br)-8a-[(2s,3r,4s,5r,6r)-3-[(2s,3r,4s,5r,6s)-5-[(2s,3r,4s,5r)-4-[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5-[(3s,5s, Chemical compound O([C@H]1[C@H](O)[C@H](O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O1)O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@H]5CC(C)(C)CC[C@@]5([C@@H](C[C@@]4(C)[C@]3(C)CC[C@H]2[C@@]1(C=O)C)O)C(=O)O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O[C@H]1[C@@H]([C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@](O)(CO)CO3)O)[C@H](O)CO2)O)[C@H](C)O1)O)O)OC(=O)C[C@@H](O)C[C@H](OC(=O)C[C@@H](O)C[C@@H]([C@@H](C)CC)O[C@H]1[C@@H]([C@@H](O)[C@H](CO)O1)O)[C@@H](C)CC)C(O)=O)[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O DRHZYJAUECRAJM-DWSYSWFDSA-N 0.000 abstract description 39
- 150000007949 saponins Chemical class 0.000 abstract description 32
- 239000001397 quillaja saponaria molina bark Substances 0.000 abstract description 27
- 230000003389 potentiating effect Effects 0.000 abstract description 12
- 238000002955 isolation Methods 0.000 abstract description 9
- 238000000746 purification Methods 0.000 abstract description 6
- 238000011156 evaluation Methods 0.000 abstract description 5
- 238000010189 synthetic method Methods 0.000 abstract description 4
- 230000001571 immunoadjuvant effect Effects 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000001093 anti-cancer Effects 0.000 abstract description 2
- 229940022399 cancer vaccine Drugs 0.000 abstract description 2
- 238000011161 development Methods 0.000 abstract description 2
- 239000000568 immunological adjuvant Substances 0.000 abstract description 2
- 229960004854 viral vaccine Drugs 0.000 abstract description 2
- YDQIRODFTJGGMP-UHFFFAOYSA-N Prosapogenin Chemical compound C12CC(C)(C)CCC2(C(=O)OC2C(C(O)C(O)C(CO)O2)O)CCC(C2(CCC34)C)(CO)C1=CCC2C3(C)CC(O)C(O)C4(C)C(=O)OC1OC(CO)C(O)C(O)C1O YDQIRODFTJGGMP-UHFFFAOYSA-N 0.000 abstract 1
- 231100001231 less toxic Toxicity 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 192
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 145
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 120
- 239000000243 solution Substances 0.000 description 91
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
- 101150041968 CDC13 gene Proteins 0.000 description 69
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 59
- 108091007433 antigens Proteins 0.000 description 59
- 102000036639 antigens Human genes 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 59
- 239000000427 antigen Substances 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 238000010898 silica gel chromatography Methods 0.000 description 49
- 229960005486 vaccine Drugs 0.000 description 46
- 235000017709 saponins Nutrition 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 229910001868 water Inorganic materials 0.000 description 41
- 235000014633 carbohydrates Nutrition 0.000 description 38
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 37
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 206010028980 Neoplasm Diseases 0.000 description 35
- 238000005481 NMR spectroscopy Methods 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 29
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 28
- 150000002772 monosaccharides Chemical class 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- 239000008194 pharmaceutical composition Substances 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
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- 229920001542 oligosaccharide Polymers 0.000 description 22
- 150000002482 oligosaccharides Chemical class 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229940086542 triethylamine Drugs 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 241000699670 Mus sp. Species 0.000 description 16
- 102000007079 Peptide Fragments Human genes 0.000 description 16
- 108010033276 Peptide Fragments Proteins 0.000 description 16
- 239000000546 pharmaceutical excipient Substances 0.000 description 16
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 15
- 229940079593 drug Drugs 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 14
- 239000000284 extract Substances 0.000 description 14
- 241000894007 species Species 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 235000009001 Quillaja saponaria Nutrition 0.000 description 13
- 201000011510 cancer Diseases 0.000 description 13
- 238000006206 glycosylation reaction Methods 0.000 description 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 13
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 12
- 241001454523 Quillaja saponaria Species 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
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- 239000003795 chemical substances by application Substances 0.000 description 12
- 150000002016 disaccharides Chemical class 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 230000028993 immune response Effects 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- UZQJVUCHXGYFLQ-AYDHOLPZSA-N [(2s,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-4-[(2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-(hy Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2[C@@]1(C=O)C)C)(C)CC(O)[C@]1(CCC(CC14)(C)C)C(=O)O[C@H]1[C@@H]([C@@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O[C@H]4[C@@H]([C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)[C@H](O)[C@@H](CO)O4)O)[C@H](O)[C@@H](CO)O3)O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UZQJVUCHXGYFLQ-AYDHOLPZSA-N 0.000 description 11
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 11
- 238000002255 vaccination Methods 0.000 description 11
- 230000003612 virological effect Effects 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
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- 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
- PIGTXFOGKFOFTO-PPEDVFHSSA-N CC1(C)CC[C@@]2([C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O)[C@@](C)(C=O)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O Chemical compound CC1(C)CC[C@@]2([C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O)[C@@](C)(C=O)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O PIGTXFOGKFOFTO-PPEDVFHSSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 125000000837 carbohydrate group Chemical group 0.000 description 8
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
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- 239000002808 molecular sieve Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 239000011734 sodium Substances 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- 231100000419 toxicity Toxicity 0.000 description 8
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- 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
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Priority Applications (1)
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| CN102112484B (zh) | 2008-04-08 | 2015-03-04 | 索隆-基特林癌症研究协会 | 三萜皂苷、其合成方法和用途 |
| CN102068446B (zh) * | 2011-01-10 | 2013-08-21 | 武汉道一堂医药研究院 | 三萜皂苷化合物在制备抗病原微生物药物中的应用 |
| AU2013204005B2 (en) * | 2012-05-23 | 2015-04-16 | Oncology Research International Limited | Improved synthesis |
| CN111499679B (zh) | 2013-01-04 | 2021-07-06 | 台湾浩鼎生技股份有限公司 | 具有较高碳水化合物抗原密度的疫苗及新颖皂素佐剂 |
| US10806119B2 (en) | 2013-06-05 | 2020-10-20 | Yeda Research And Development Co. Ltd. | Plant with altered content of steroidal alkaloids |
| NZ714555A (en) | 2013-09-17 | 2020-03-27 | Obi Pharma Inc | Compositions of a carbohydrate vaccine for inducing immune responses and uses thereof in cancer treatment |
| JP6774943B2 (ja) | 2014-05-30 | 2020-10-28 | メモリアル スローン ケタリング キャンサー センター | 極小サポニンアナログ、その合成および使用 |
| US10676723B2 (en) | 2015-05-11 | 2020-06-09 | David Gordon Bermudes | Chimeric protein toxins for expression by therapeutic bacteria |
| AR105910A1 (es) | 2015-09-04 | 2017-11-22 | Obi Pharma Inc | Matrices de glicano y método de uso |
| US20180327436A1 (en) * | 2015-11-06 | 2018-11-15 | Adjuvance Technologies, Inc. | Triterpene saponin analogues |
| EP3436482A4 (en) | 2016-03-29 | 2020-03-11 | OBI Pharma, Inc. | ANTIBODIES, PHARMACEUTICAL COMPOSITIONS AND METHODS |
| US10980894B2 (en) | 2016-03-29 | 2021-04-20 | Obi Pharma, Inc. | Antibodies, pharmaceutical compositions and methods |
| CA3021548A1 (en) | 2016-04-22 | 2017-10-26 | Obi Pharma, Inc. | Cancer immunotherapy by immune activation or immune modulation via globo series antigens |
| WO2018022933A1 (en) | 2016-07-27 | 2018-02-01 | Obi Pharma, Inc. | Immunogenic/therapeutic glycan compositions and uses thereof |
| KR102528998B1 (ko) | 2016-07-29 | 2023-05-03 | 오비아이 파머 인코퍼레이티드 | 인간 항체, 제약 조성물 및 방법 |
| CN110290800A (zh) | 2016-11-21 | 2019-09-27 | 台湾浩鼎生技股份有限公司 | 缀合生物分子、医药组合物及方法 |
| US11129906B1 (en) | 2016-12-07 | 2021-09-28 | David Gordon Bermudes | Chimeric protein toxins for expression by therapeutic bacteria |
| JP2020516657A (ja) * | 2017-04-13 | 2020-06-11 | アジュバンス・テクノロジーズ・インコーポレーテッド | トリテルペンサポニン合成、中間体及びアジュバントの組み合わせ |
| SG10202108075YA (en) * | 2017-04-25 | 2021-09-29 | Adjuvance Technologies Inc | Triterpene saponin analogues |
| JP7177082B2 (ja) * | 2017-04-25 | 2022-11-22 | アジュバンス・テクノロジーズ・インコーポレーテッド | トリテルペンサポニン類似物 |
| CA3075822A1 (en) * | 2017-10-16 | 2019-04-25 | Adjuvance Technologies, Inc. | Triterpene saponin analogues |
| CA3085356A1 (en) | 2017-12-29 | 2019-07-04 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectin and galectin-3 |
| US12497429B2 (en) * | 2018-03-20 | 2025-12-16 | The Uab Research Foundation | Saponin-based vaccine adjuvants |
| WO2020006176A1 (en) | 2018-06-27 | 2020-01-02 | Obi Pharma, Inc. | Glycosynthase variants for glycoprotein engineering and methods of use |
| US12041907B2 (en) | 2018-09-06 | 2024-07-23 | Yeda Research And Development Co. Ltd. | Cellulose-synthase-like enzymes and uses thereof |
| EP3849521A1 (en) | 2018-09-14 | 2021-07-21 | Massachusetts Institute Of Technology | Nanoparticle vaccine adjuvant and methods of use thereof |
| BR112021012482A2 (pt) | 2018-12-27 | 2021-09-08 | Glycomimetics, Inc. | C-glicosídeos inibidores de galectina-3 |
| US11845771B2 (en) | 2018-12-27 | 2023-12-19 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| US20220409721A1 (en) * | 2019-11-05 | 2022-12-29 | Adjuvance Technologies, Inc. | Varicella zoster |
| US20230128815A1 (en) * | 2020-03-23 | 2023-04-27 | Adjuvance Technologies, Inc. | Adjuvant compounds, salt forms, and formulations |
| US20250282811A1 (en) * | 2021-10-02 | 2025-09-11 | Desert King Chile S.A | A 3-o-monodesmosidic saponins extract, stable at physiological ph, method for preparing it from a quillaja plant extract cultured with a microbial consortium, uses and such microbial consortium |
| EP4190359A1 (en) | 2021-12-03 | 2023-06-07 | Asociación Centro de Investigación Cooperativa en Biociencias - CIC bioGUNE | Saponin-based adjuvants and vaccines |
| US20230190920A1 (en) | 2021-12-19 | 2023-06-22 | Massachusetts Institute Of Technology | Compositions and methods for long-lasting germinal center responses to a priming immunization |
| WO2023139145A1 (en) | 2022-01-19 | 2023-07-27 | Asociación Centro De Investigación Cooperativa En Biociencias-Cic Biogune | Saponin-based adjuvants and vaccines |
| WO2024218268A1 (en) | 2023-04-20 | 2024-10-24 | Asociación Centro De Investigación Cooperativa En Biociencias-Cic Biogune | Saponin derivatives as adjuvants and photoaffinity probes |
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| JPS6112695A (ja) * | 1984-06-28 | 1986-01-21 | Rikagaku Kenkyusho | シアル酸誘導体 |
| US5057540A (en) * | 1987-05-29 | 1991-10-15 | Cambridge Biotech Corporation | Saponin adjuvant |
| US5583112A (en) | 1987-05-29 | 1996-12-10 | Cambridge Biotech Corporation | Saponin-antigen conjugates and the use thereof |
| JPH09169648A (ja) * | 1995-12-22 | 1997-06-30 | Nippon Shinyaku Co Ltd | 医薬組成物 |
| CA2273922C (en) * | 1996-12-02 | 2008-08-05 | Aquila Biopharmaceuticals, Inc. | Novel saponin compositions and uses thereof |
| US6231859B1 (en) | 1996-12-02 | 2001-05-15 | Aquila Biopharmaceuticals, Inc. | Saponin adjuvant compositions |
| BR9809149A (pt) | 1997-05-20 | 2000-08-01 | Galenica Pharmaceuticals Inc | Análogos de triterpeno saponina dotados de adjuvante e atividade imonoestimulatória |
| US6080725A (en) | 1997-05-20 | 2000-06-27 | Galenica Pharmaceuticals, Inc. | Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof |
| WO1998056415A1 (en) * | 1997-06-11 | 1998-12-17 | Aquila Biopharmaceuticals, Inc. | Purified saponins as oral adjuvants |
| AU5565599A (en) | 1998-08-14 | 2000-03-06 | Dante J. Marciani | Chemically modified saponins and the use thereof as adjuvants |
| US7457415B2 (en) | 1998-08-20 | 2008-11-25 | Akikaze Technologies, Llc | Secure information distribution system utilizing information segment scrambling |
| US6716428B1 (en) | 1999-10-06 | 2004-04-06 | The Ohio State University Research Foundation | Antigenic modification of polypeptides |
| US20040242502A1 (en) * | 2003-04-08 | 2004-12-02 | Galenica Pharmaceuticals, Inc. | Semi-synthetic saponin analogs with carrier and immune stimulatory activities for DNA and RNA vaccines |
| WO2006116876A1 (en) * | 2005-05-04 | 2006-11-09 | National Research Council Of Canada | Method for production of saponaria from microspores |
| CN100335073C (zh) * | 2005-08-19 | 2007-09-05 | 浙江大学 | 木鳖子含三萜皂甙成分提取物的制备方法 |
| CN102112484B (zh) * | 2008-04-08 | 2015-03-04 | 索隆-基特林癌症研究协会 | 三萜皂苷、其合成方法和用途 |
| CN101322734B (zh) | 2008-07-22 | 2013-05-29 | 沈阳药科大学 | 具有抗炎免疫作用的轮叶党参总皂苷及其制备方法 |
| JP6774943B2 (ja) * | 2014-05-30 | 2020-10-28 | メモリアル スローン ケタリング キャンサー センター | 極小サポニンアナログ、その合成および使用 |
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