CA3003483C - Triterpene saponin analogues - Google Patents
Triterpene saponin analogues Download PDFInfo
- Publication number
- CA3003483C CA3003483C CA3003483A CA3003483A CA3003483C CA 3003483 C CA3003483 C CA 3003483C CA 3003483 A CA3003483 A CA 3003483A CA 3003483 A CA3003483 A CA 3003483A CA 3003483 C CA3003483 C CA 3003483C
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- antigen
- nitrogen
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- sulfur
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- 229930182493 triterpene saponin Natural products 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 239000000427 antigen Substances 0.000 claims abstract description 46
- 102000036639 antigens Human genes 0.000 claims abstract description 46
- 108091007433 antigens Proteins 0.000 claims abstract description 46
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000002252 acyl group Chemical group 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 24
- 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 9
- 241000700605 Viruses Species 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 241000589968 Borrelia Species 0.000 claims description 6
- 241000589969 Borreliella burgdorferi Species 0.000 claims description 6
- 241001148605 Borreliella garinii Species 0.000 claims description 6
- 244000274051 Cornus kousa Species 0.000 claims description 6
- 206010013023 diphtheria Diseases 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 241000589970 Spirochaetales 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
- 206010043376 Tetanus Diseases 0.000 claims description 4
- 241000186216 Corynebacterium Species 0.000 claims 2
- 241000700721 Hepatitis B virus Species 0.000 claims 2
- 241000193403 Clostridium Species 0.000 claims 1
- 241000193449 Clostridium tetani Species 0.000 claims 1
- -1 triterpene glycoside saponin Chemical class 0.000 abstract description 245
- 239000002671 adjuvant Substances 0.000 abstract description 98
- 239000000203 mixture Substances 0.000 abstract description 72
- 229930182490 saponin Natural products 0.000 abstract description 55
- 239000001397 quillaja saponaria molina bark Substances 0.000 abstract description 46
- 238000003786 synthesis reaction Methods 0.000 abstract description 44
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 abstract description 22
- 230000003389 potentiating effect Effects 0.000 abstract description 14
- 230000028993 immune response Effects 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 10
- 230000003053 immunization Effects 0.000 abstract description 7
- 238000002649 immunization Methods 0.000 abstract description 7
- 238000011282 treatment Methods 0.000 abstract description 7
- 208000035473 Communicable disease Diseases 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 296
- 229910052757 nitrogen Inorganic materials 0.000 description 186
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 185
- 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
- 125000005842 heteroatom Chemical group 0.000 description 163
- 229910052760 oxygen Inorganic materials 0.000 description 162
- 239000001301 oxygen Chemical group 0.000 description 162
- 125000001931 aliphatic group Chemical group 0.000 description 117
- 239000001257 hydrogen Substances 0.000 description 107
- 229910052739 hydrogen Inorganic materials 0.000 description 107
- 125000003710 aryl alkyl group Chemical group 0.000 description 80
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 75
- 125000000623 heterocyclic group Chemical group 0.000 description 73
- 229910052736 halogen Inorganic materials 0.000 description 66
- 150000002367 halogens Chemical group 0.000 description 60
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 59
- 150000002431 hydrogen Chemical group 0.000 description 58
- 239000000243 solution Substances 0.000 description 57
- 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 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 235000017709 saponins Nutrition 0.000 description 54
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
- 230000015572 biosynthetic process Effects 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 42
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 39
- 229960005486 vaccine Drugs 0.000 description 39
- 125000003118 aryl group Chemical group 0.000 description 38
- 150000001720 carbohydrates Chemical class 0.000 description 35
- 229920006395 saturated elastomer Polymers 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 150000002148 esters Chemical class 0.000 description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 31
- 235000014633 carbohydrates Nutrition 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 238000010898 silica gel chromatography Methods 0.000 description 30
- 150000007949 saponins Chemical class 0.000 description 27
- 150000001241 acetals Chemical class 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- 238000000746 purification Methods 0.000 description 25
- 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 24
- 150000005215 alkyl ethers Chemical class 0.000 description 23
- 125000000217 alkyl group Chemical group 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 23
- 125000001072 heteroaryl group Chemical group 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- 125000006239 protecting group Chemical group 0.000 description 18
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 241000894007 species Species 0.000 description 17
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 16
- 241000699670 Mus sp. Species 0.000 description 16
- 238000007792 addition Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 13
- 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 13
- 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 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 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 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 description 13
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 12
- 150000002243 furanoses Chemical class 0.000 description 12
- 230000002949 hemolytic effect Effects 0.000 description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 150000003214 pyranose derivatives Chemical group 0.000 description 12
- 150000004043 trisaccharides Chemical class 0.000 description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 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 description 11
- 125000002015 acyclic group Chemical group 0.000 description 10
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- 125000005843 halogen group Chemical group 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000282414 Homo sapiens Species 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
- 241001465754 Metazoa Species 0.000 description 9
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- 235000009001 Quillaja saponaria Nutrition 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
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- STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 5
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| CN111212846B (zh) | 2017-10-16 | 2023-05-26 | 佐剂技术公司 | 三萜皂苷类似物 |
| US20190275134A1 (en) | 2018-03-12 | 2019-09-12 | Janssen Pharmaceuticals, Inc | Vaccines against urinary tract infections |
| JP2023500676A (ja) | 2019-11-05 | 2023-01-10 | アジュバンス・テクノロジーズ・インコーポレーテッド | 水痘帯状疱疹 |
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