IL286493B - Triterpene saponin analogues, methods of producing same, compositions comprising same and uses thereof - Google Patents

Info

Publication number

IL286493B

IL286493B IL286493A IL28649321A IL286493B IL 286493 B IL286493 B IL 286493B IL 286493 A IL286493 A IL 286493A IL 28649321 A IL28649321 A IL 28649321A IL 286493 B IL286493 B IL 286493B

Authority

IL

Israel

Prior art keywords

group

nitrogen

oxygen

sulfur

antigen

Prior art date

2015-11-06

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 36
• 238000004519 manufacturing process Methods 0.000 title description 4
• 229930182493 triterpene saponin Natural products 0.000 title description 2
• 238000002360 preparation method Methods 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 175
• 239000000427 antigen Substances 0.000 claims description 46
• 102000036639 antigens Human genes 0.000 claims description 46
• 108091007433 antigens Proteins 0.000 claims description 46
• 239000008194 pharmaceutical composition Substances 0.000 claims description 39
• 150000003839 salts Chemical class 0.000 claims description 26
• 241000894006 Bacteria Species 0.000 claims description 16
• 208000016604 Lyme disease Diseases 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 230000002194 synthesizing effect Effects 0.000 claims description 7
• 241000589968 Borrelia Species 0.000 claims description 6
• 241000589969 Borreliella burgdorferi Species 0.000 claims description 6
• 244000274051 Cornus kousa Species 0.000 claims description 6
• 241000700605 Viruses Species 0.000 claims description 6
• 206010013023 diphtheria Diseases 0.000 claims description 6
• 241001148605 Borreliella garinii Species 0.000 claims description 5
• 208000002672 hepatitis B Diseases 0.000 claims description 5
• 241000588832 Bordetella pertussis Species 0.000 claims description 4
• 201000005702 Pertussis Diseases 0.000 claims description 4
• 241000589970 Spirochaetales Species 0.000 claims description 4
• 206010043376 Tetanus Diseases 0.000 claims description 4
• 241000193403 Clostridium Species 0.000 claims 2
• 241000186216 Corynebacterium Species 0.000 claims 2
• 241000700721 Hepatitis B virus Species 0.000 claims 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 294
• -1 triterpene glycoside saponin Chemical class 0.000 description 254
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 185
• 229910052757 nitrogen Inorganic materials 0.000 description 184
• 229910052717 sulfur Chemical group 0.000 description 165
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 164
• 239000011593 sulfur Chemical group 0.000 description 164
• 229910052760 oxygen Inorganic materials 0.000 description 163
• 239000001301 oxygen Chemical group 0.000 description 162
• 125000005842 heteroatom Chemical group 0.000 description 155
• 125000001931 aliphatic group Chemical group 0.000 description 112
• 229910052739 hydrogen Inorganic materials 0.000 description 109
• 239000001257 hydrogen Substances 0.000 description 108
• 239000002671 adjuvant Substances 0.000 description 95
• 125000003710 aryl alkyl group Chemical group 0.000 description 81
• 125000000623 heterocyclic group Chemical group 0.000 description 79
• 125000000041 C6-C10 aryl group Chemical group 0.000 description 75
• 125000002252 acyl group Chemical group 0.000 description 70
• 229910052736 halogen Inorganic materials 0.000 description 66
• 150000002367 halogens Chemical group 0.000 description 60
• 150000002431 hydrogen Chemical group 0.000 description 57
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
• 239000000203 mixture Substances 0.000 description 56
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 53
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 50
• 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 43
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
• 229960005486 vaccine Drugs 0.000 description 39
• 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 description 37
• 125000003118 aryl group Chemical group 0.000 description 37
• 150000001720 carbohydrates Chemical class 0.000 description 37
• 239000000243 solution Substances 0.000 description 36
• 150000002148 esters Chemical class 0.000 description 33
• 229920006395 saturated elastomer Polymers 0.000 description 33
• 230000015572 biosynthetic process Effects 0.000 description 32
• 235000014633 carbohydrates Nutrition 0.000 description 32
• 238000003786 synthesis reaction Methods 0.000 description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 31
• 235000019439 ethyl acetate Nutrition 0.000 description 28
• 239000011541 reaction mixture Substances 0.000 description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
• 150000001241 acetals Chemical class 0.000 description 23
• 150000005215 alkyl ethers Chemical class 0.000 description 23
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 23
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 23
• 125000001072 heteroaryl group Chemical group 0.000 description 23
• 229930182490 saponin Natural products 0.000 description 22
• 235000017709 saponins Nutrition 0.000 description 22
• 125000000217 alkyl group Chemical group 0.000 description 21
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 21
• 125000001424 substituent group Chemical group 0.000 description 21
• 238000006243 chemical reaction Methods 0.000 description 20
• 238000010898 silica gel chromatography Methods 0.000 description 20
• 238000000746 purification Methods 0.000 description 19
• SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 125000006239 protecting group Chemical group 0.000 description 18
• MQUFAARYGOUYEV-UWEXFCAOSA-N Quillaic acid Natural products CC1(C)CC[C@@]2([C@H](O)C[C@]3(C)C(=CC[C@H]4[C@@]5(C)CC[C@H](O)[C@](C)(C=O)[C@H]5CC[C@@]34C)[C@H]2C1)C(=O)O MQUFAARYGOUYEV-UWEXFCAOSA-N 0.000 description 17
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 17
• 241000894007 species Species 0.000 description 17
• 239000001397 quillaja saponaria molina bark Substances 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 230000000694 effects Effects 0.000 description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 13
• 230000003389 potentiating effect Effects 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 12
• 125000004122 cyclic group Chemical group 0.000 description 12
• 150000002243 furanoses Chemical class 0.000 description 12
• 230000028993 immune response Effects 0.000 description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 150000003214 pyranose derivatives Chemical group 0.000 description 12
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 11
• 125000002015 acyclic group Chemical group 0.000 description 11
• 150000007949 saponins Chemical class 0.000 description 11
• 239000003814 drug Substances 0.000 description 10
• 125000005843 halogen group Chemical group 0.000 description 10
• 239000000543 intermediate Substances 0.000 description 10
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
• 150000001408 amides Chemical class 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 150000002772 monosaccharides Chemical class 0.000 description 9
• 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 description 9
• 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
• 241001465754 Metazoa Species 0.000 description 8
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
• PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 125000002947 alkylene group Chemical group 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 229910052799 carbon Inorganic materials 0.000 description 7
• 231100000419 toxicity Toxicity 0.000 description 7
• 230000001988 toxicity Effects 0.000 description 7
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 241000282414 Homo sapiens Species 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 241001454523 Quillaja saponaria Species 0.000 description 6
• 235000009001 Quillaja saponaria Nutrition 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
• 229940037003 alum Drugs 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
• 239000003795 chemical substances by application Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 239000003937 drug carrier Substances 0.000 description 6
• 230000002949 hemolytic effect Effects 0.000 description 6
• 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• 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 6
• 150000004043 trisaccharides Chemical class 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
• 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 5
• 150000001721 carbon Chemical group 0.000 description 5
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• 231100000252 nontoxic Toxicity 0.000 description 5
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• MQUFAARYGOUYEV-UAWZMHPWSA-N quillaic acid Chemical compound C1C[C@H](O)[C@@](C)(C=O)[C@@H]2CC[C@@]3(C)[C@]4(C)C[C@@H](O)[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MQUFAARYGOUYEV-UAWZMHPWSA-N 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 238000011282 treatment Methods 0.000 description 5
• HBMPTLRLIMPVIH-VAMGGRTRSA-N (2s,3r,4r)-3-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2h-pyran Chemical compound C([C@@H]1[C@@H]([C@@H](C=CO1)OCC=1C=CC=CC=1)N=[N+]=[N-])OCC1=CC=CC=C1 HBMPTLRLIMPVIH-VAMGGRTRSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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• 208000035473 Communicable disease Diseases 0.000 description 4
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• 206010028980 Neoplasm Diseases 0.000 description 4
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• 238000010521 absorption reaction Methods 0.000 description 4
• 125000005137 alkenylsulfonyl group Chemical group 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
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• 239000003963 antioxidant agent Substances 0.000 description 4
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• 125000004429 atom Chemical group 0.000 description 4
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• 201000011510 cancer Diseases 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
• 150000002016 disaccharides Chemical class 0.000 description 4
• 235000019441 ethanol Nutrition 0.000 description 4
• CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 4
• 125000000524 functional group Chemical group 0.000 description 4
• 230000002163 immunogen Effects 0.000 description 4
• 230000001965 increasing effect Effects 0.000 description 4
• 238000002955 isolation Methods 0.000 description 4
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
• 235000019341 magnesium sulphate Nutrition 0.000 description 4
• 229920001282 polysaccharide Polymers 0.000 description 4
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• 125000006413 ring segment Chemical group 0.000 description 4
• 238000000926 separation method Methods 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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