BRPI0611447A2 - imunógenos para vacinas contra meningite a - Google Patents
imunógenos para vacinas contra meningite a Download PDFInfo
- Publication number
- BRPI0611447A2 BRPI0611447A2 BRPI0611447-4A BRPI0611447A BRPI0611447A2 BR PI0611447 A2 BRPI0611447 A2 BR PI0611447A2 BR PI0611447 A BRPI0611447 A BR PI0611447A BR PI0611447 A2 BRPI0611447 A2 BR PI0611447A2
- Authority
- BR
- Brazil
- Prior art keywords
- oligosaccharide
- mannose
- formula
- unit
- protein
- Prior art date
Links
- 229960005486 vaccine Drugs 0.000 title claims abstract description 43
- 201000009906 Meningitis Diseases 0.000 title claims abstract description 23
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 171
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 163
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 146
- 238000000034 method Methods 0.000 claims abstract description 133
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 95
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 95
- 125000006850 spacer group Chemical group 0.000 claims abstract description 56
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 31
- 230000001268 conjugating effect Effects 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 103
- -1 heteroacyl Chemical group 0.000 claims description 57
- 125000006239 protecting group Chemical group 0.000 claims description 48
- 150000004676 glycans Chemical class 0.000 claims description 41
- 230000002163 immunogen Effects 0.000 claims description 39
- 229920001282 polysaccharide Polymers 0.000 claims description 38
- 239000005017 polysaccharide Substances 0.000 claims description 38
- 150000001412 amines Chemical class 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 32
- 150000001540 azides Chemical class 0.000 claims description 31
- 150000001720 carbohydrates Chemical group 0.000 claims description 30
- 229910019142 PO4 Inorganic materials 0.000 claims description 25
- 239000010452 phosphate Substances 0.000 claims description 25
- 238000006751 Mitsunobu reaction Methods 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229910052698 phosphorus Inorganic materials 0.000 claims description 21
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical group OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 20
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 18
- 239000000427 antigen Substances 0.000 claims description 18
- 108091007433 antigens Proteins 0.000 claims description 18
- 102000036639 antigens Human genes 0.000 claims description 18
- 239000011574 phosphorus Substances 0.000 claims description 18
- 239000002671 adjuvant Substances 0.000 claims description 17
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- 239000012039 electrophile Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000000746 purification Methods 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 150000002703 mannose derivatives Chemical class 0.000 claims description 11
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 10
- 230000001588 bifunctional effect Effects 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 230000000269 nucleophilic effect Effects 0.000 claims description 9
- 108010071134 CRM197 (non-toxic variant of diphtheria toxin) Proteins 0.000 claims description 8
- 241000588724 Escherichia coli Species 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229940037003 alum Drugs 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- CPGRMGOILBSUQC-UHFFFAOYSA-N phosphoryl azide Chemical compound [N-]=[N+]=NP(=O)(N=[N+]=[N-])N=[N+]=[N-] CPGRMGOILBSUQC-UHFFFAOYSA-N 0.000 claims description 7
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 229960000814 tetanus toxoid Drugs 0.000 claims description 5
- URARQBMUQIRZQO-CBPJZXOFSA-N (3S,4R,5S,6R)-3-azido-6-(hydroxymethyl)oxane-2,4,5-triol Chemical compound OC[C@H]1OC(O)[C@@H](N=[N+]=[N-])[C@@H](O)[C@@H]1O URARQBMUQIRZQO-CBPJZXOFSA-N 0.000 claims description 4
- OTLLEIBWKHEHGU-UHFFFAOYSA-N 2-[5-[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-4-phosphonooxyhexanedioic acid Chemical compound C1=NC=2C(N)=NC=NC=2N1C(C(C1O)O)OC1COC1C(CO)OC(OC(C(O)C(OP(O)(O)=O)C(O)C(O)=O)C(O)=O)C(O)C1O OTLLEIBWKHEHGU-UHFFFAOYSA-N 0.000 claims description 4
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 4
- 241000193998 Streptococcus pneumoniae Species 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229960003983 diphtheria toxoid Drugs 0.000 claims description 4
- 231100000776 exotoxin Toxicity 0.000 claims description 4
- 239000002095 exotoxin Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 230000002035 prolonged effect Effects 0.000 claims description 4
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 108010088751 Albumins Proteins 0.000 claims description 3
- 102000009027 Albumins Human genes 0.000 claims description 3
- 231100000699 Bacterial toxin Toxicity 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 201000005702 Pertussis Diseases 0.000 claims description 3
- 239000000688 bacterial toxin Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- PWEBUXCTKOWPCW-UHFFFAOYSA-L squarate Chemical compound [O-]C1=C([O-])C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-L 0.000 claims description 3
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- 125000002743 phosphorus functional group Chemical group 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 241001478240 Coccus Species 0.000 claims 1
- JXASPPWQHFOWPL-UHFFFAOYSA-N Tamarixin Natural products C1=C(O)C(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 JXASPPWQHFOWPL-UHFFFAOYSA-N 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 38
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- 241000588650 Neisseria meningitidis Species 0.000 description 28
- 102000014914 Carrier Proteins Human genes 0.000 description 27
- 108010078791 Carrier Proteins Proteins 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 19
- 125000000837 carbohydrate group Chemical group 0.000 description 17
- 230000009851 immunogenic response Effects 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 15
- 239000000499 gel Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 150000004713 phosphodiesters Chemical group 0.000 description 14
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
- 238000004448 titration Methods 0.000 description 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 12
- 230000003053 immunization Effects 0.000 description 12
- 238000002649 immunization Methods 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 11
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 10
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 238000002965 ELISA Methods 0.000 description 8
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 239000000539 dimer Substances 0.000 description 8
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 8
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 8
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 6
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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 5
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- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 5
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- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 3
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229940031937 polysaccharide vaccine Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 241000737598 recombinant Hepatitis B virus Species 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- BYMVZHORNHZYPQ-UHFFFAOYSA-N sodium;diethyl phosphite Chemical compound [Na+].CCOP([O-])OCC BYMVZHORNHZYPQ-UHFFFAOYSA-N 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 150000003569 thioglycosides Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 229960002175 thyroglobulin Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- AYPRHVFFCLKSBU-UHFFFAOYSA-N trifluoromethanesulfonoperoxoic acid Chemical compound OOS(=O)(=O)C(F)(F)F AYPRHVFFCLKSBU-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- QGDIJZMKEQCRBX-UHFFFAOYSA-N zinc;ethene Chemical compound [Zn+2].[CH-]=C.[CH-]=C QGDIJZMKEQCRBX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67828905P | 2005-05-06 | 2005-05-06 | |
| US60/678,289 | 2005-05-06 | ||
| PCT/IB2006/001703 WO2006120576A2 (en) | 2005-05-06 | 2006-05-08 | Immunogens for meningitidis-a vaccines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0611447A2 true BRPI0611447A2 (pt) | 2010-09-08 |
Family
ID=36942242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0611447-4A BRPI0611447A2 (pt) | 2005-05-06 | 2006-05-08 | imunógenos para vacinas contra meningite a |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8062641B2 (https=) |
| EP (1) | EP1885734B1 (https=) |
| JP (2) | JP2008540398A (https=) |
| CN (1) | CN101282984B (https=) |
| AU (1) | AU2006245440B2 (https=) |
| BR (1) | BRPI0611447A2 (https=) |
| CA (1) | CA2606890C (https=) |
| ES (1) | ES2533248T3 (https=) |
| MX (1) | MX2007013881A (https=) |
| NZ (1) | NZ563940A (https=) |
| PL (1) | PL1885734T3 (https=) |
| PT (1) | PT1885734E (https=) |
| RU (1) | RU2412944C2 (https=) |
| WO (1) | WO2006120576A2 (https=) |
| ZA (1) | ZA200710558B (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX339524B (es) | 2001-10-11 | 2016-05-30 | Wyeth Corp | Composiciones inmunogenicas novedosas para la prevencion y tratamiento de enfermedad meningococica. |
| US8398983B2 (en) | 2005-06-27 | 2013-03-19 | Glaxosmithkline Biologicals, S.A. | Immunogenic composition |
| AR064642A1 (es) | 2006-12-22 | 2009-04-15 | Wyeth Corp | Polinucleotido vector que lo comprende celula recombinante que comprende el vector polipeptido , anticuerpo , composicion que comprende el polinucleotido , vector , celula recombinante polipeptido o anticuerpo , uso de la composicion y metodo para preparar la composicion misma y preparar una composi |
| GB0700562D0 (en) * | 2007-01-11 | 2007-02-21 | Novartis Vaccines & Diagnostic | Modified Saccharides |
| AU2014200640B2 (en) * | 2007-01-11 | 2016-06-16 | Glaxosmithkline Biologicals Sa | Modified saccharides |
| US8828952B2 (en) | 2007-10-16 | 2014-09-09 | Progen Pharmaceuticals Limited | Sulfated oligosaccharide derivatives |
| KR101594228B1 (ko) | 2010-08-23 | 2016-02-15 | 와이어쓰 엘엘씨 | 네이세리아 메닌기티디스 ｒＬＰ２０８６ 항원의 안정한 제제 |
| ES2744471T3 (es) | 2010-09-04 | 2020-02-25 | Glaxosmithkline Biologicals Sa | Ensayos de anticuerpos bactericidas para evaluar la inmunogenia y la potencia de vacunas de sacárido capsular meningocócico |
| NZ607224A (en) | 2010-09-10 | 2014-11-28 | Wyeth Llc | Non-lipidated variants of neisseria meningitidis orf2086 antigens |
| CN102417521B (zh) * | 2010-09-28 | 2014-05-07 | 中国医学科学院医药生物技术研究所 | 一种非环核苷类抗病毒药物磷酸单酯化合物的制备方法 |
| WO2012103444A2 (en) * | 2011-01-28 | 2012-08-02 | Purdue Research Foundation | Immunogenic compositions and reagents for preparing |
| US9616139B2 (en) | 2011-07-12 | 2017-04-11 | The General Hospital Corporation | Conjugating amines |
| RU2476444C1 (ru) * | 2011-07-15 | 2013-02-27 | Российская Федерация, от имени которой выступает Министерство промышленности и торговли Российской Федерации (Минпромторг России) | СПОСОБ ПОЛУЧЕНИЯ КОНЪЮГАТА НОНА-β-(1→3)-ГЛЮКОЗИДА С БЫЧЬИМ СЫВОРОТОЧНЫМ АЛЬБУМИНОМ СКВАРАТНЫМ МЕТОДОМ |
| MX359256B (es) | 2012-03-09 | 2018-09-19 | Pfizer | Composiciones de neisseria meningitidis y metodos de las mismas. |
| SA115360586B1 (ar) | 2012-03-09 | 2017-04-12 | فايزر انك | تركيبات لعلاج الالتهاب السحائي البكتيري وطرق لتحضيرها |
| WO2014130613A2 (en) * | 2013-02-22 | 2014-08-28 | Amgen Inc. | Carbohydrate phosphonate derivatives as modulators of glycosylation |
| US9802987B2 (en) | 2013-03-08 | 2017-10-31 | Pfizer Inc. | Immunogenic fusion polypeptides |
| HK1224300A1 (zh) * | 2013-07-07 | 2017-08-18 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | 合成针对1型肺炎链球菌的疫苗 |
| RU2662968C2 (ru) | 2013-09-08 | 2018-07-31 | Пфайзер Инк. | Иммуногенная композиция против neisseria meningitidis (варианты) |
| JP6526692B2 (ja) * | 2014-02-25 | 2019-06-05 | エムエスディー ウェルカム トラスト ヒルマン ラボラトリーズ プライベート リミテッドＭｓｄ Ｗｅｌｌｃｏｍｅ Ｔｒｕｓｔ Ｈｉｌｌｅｍａｎ Ｌａｂｏｒａｔｏｒｉｅｓ Ｐｖｔ．Ｌｔｄ． | 髄膜炎菌（Ｎｅｉｓｓｅｒｉａ ｍｅｎｉｎｇｉｔｉｄｉｓ）血清型Ｘの新規の合成オリゴマー及びその調製方法 |
| BR112017006447A2 (pt) * | 2014-10-09 | 2017-12-12 | Msd Wellcome Trust Hilleman Laboratories Pvt Ltd | processo de conjugação e conjugados sintéticos de oligossacarídeo-proteína obtidos dos mesmos |
| AU2016221318B2 (en) | 2015-02-19 | 2020-06-25 | Pfizer Inc. | Neisseria meningitidis compositions and methods thereof |
| KR102906912B1 (ko) | 2016-09-02 | 2026-01-05 | 사노피 파스퇴르 인크 | 네이세리아 메닌기티디스 백신 |
| AU2018215585B2 (en) | 2017-01-31 | 2022-03-17 | Pfizer Inc. | Neisseria meningitidis compositions and methods thereof |
| WO2018173068A1 (en) * | 2017-03-21 | 2018-09-27 | Msd Wellcome Trust Hilleman Laboratories Pvt. Ltd. | A novel synthetic neisseria meningitidis serogroup a oligomer and process for synthesizing thereof |
| CA3120451A1 (en) | 2018-11-22 | 2020-05-28 | Idorsia Pharmaceuticals Ltd | Stable vaccine against clostridium difficile with modifications to the ps-ii saccharide |
| EP4034157A1 (en) | 2019-09-27 | 2022-08-03 | Pfizer Inc. | Neisseria meningitidis compositions and methods thereof |
| CN118178643B (zh) * | 2024-04-28 | 2024-11-29 | 亚培烯科技(上海)有限公司 | 饱和α烯烃低聚物作为佐剂在动物疫苗中的应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356170A (en) | 1981-05-27 | 1982-10-26 | Canadian Patents & Development Ltd. | Immunogenic polysaccharide-protein conjugates |
| US6114309A (en) * | 1997-11-21 | 2000-09-05 | Incara Research Laboratories | Combinatorial library of moenomycin analogs and methods of producing same |
| JP4774496B2 (ja) * | 2001-06-14 | 2011-09-14 | 独立行政法人産業技術総合研究所 | α−マンノシダーゼ |
| PT1777236T (pt) * | 2002-03-26 | 2017-02-13 | Glaxosmithkline Biologicals Sa | Sacáridos modificados possuindo estabilidade melhorada em água para utilização como um medicamento |
| GB0220198D0 (en) * | 2002-08-30 | 2002-10-09 | Chiron Spa | Modified saccharides,conjugates thereof and their manufacture |
| ES2461350T3 (es) * | 2003-01-30 | 2014-05-19 | Novartis Ag | Vacunas inyectables contra múltiples serogrupos de meningococos |
| RU2250113C2 (ru) * | 2003-06-04 | 2005-04-20 | Институт биоорганической химии им. академиков М.М.Шемякина и Ю.А.Овчинникова Российской академии наук | Способ приготовления бивалентной вакцины для профилактики менингококковой инфекции |
-
2006
- 2006-05-08 ES ES06765581.1T patent/ES2533248T3/es active Active
- 2006-05-08 AU AU2006245440A patent/AU2006245440B2/en not_active Ceased
- 2006-05-08 NZ NZ563940A patent/NZ563940A/en not_active IP Right Cessation
- 2006-05-08 US US11/913,765 patent/US8062641B2/en active Active
- 2006-05-08 WO PCT/IB2006/001703 patent/WO2006120576A2/en not_active Ceased
- 2006-05-08 EP EP06765581.1A patent/EP1885734B1/en active Active
- 2006-05-08 JP JP2008509538A patent/JP2008540398A/ja not_active Withdrawn
- 2006-05-08 PT PT06765581T patent/PT1885734E/pt unknown
- 2006-05-08 MX MX2007013881A patent/MX2007013881A/es active IP Right Grant
- 2006-05-08 CA CA2606890A patent/CA2606890C/en active Active
- 2006-05-08 BR BRPI0611447-4A patent/BRPI0611447A2/pt not_active Application Discontinuation
- 2006-05-08 CN CN2006800243581A patent/CN101282984B/zh not_active Expired - Fee Related
- 2006-05-08 RU RU2007145219/05A patent/RU2412944C2/ru active
- 2006-05-08 PL PL06765581T patent/PL1885734T3/pl unknown
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2007
- 2007-12-04 ZA ZA200710558A patent/ZA200710558B/xx unknown
-
2013
- 2013-04-05 JP JP2013079295A patent/JP5699174B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2533248T3 (es) | 2015-04-08 |
| CN101282984B (zh) | 2013-05-08 |
| EP1885734B1 (en) | 2015-01-14 |
| US20090304734A1 (en) | 2009-12-10 |
| AU2006245440A1 (en) | 2006-11-16 |
| JP5699174B2 (ja) | 2015-04-08 |
| JP2008540398A (ja) | 2008-11-20 |
| NZ563940A (en) | 2010-11-26 |
| CN101282984A (zh) | 2008-10-08 |
| RU2007145219A (ru) | 2009-06-20 |
| MX2007013881A (es) | 2008-10-22 |
| JP2013136639A (ja) | 2013-07-11 |
| RU2412944C2 (ru) | 2011-02-27 |
| EP1885734A2 (en) | 2008-02-13 |
| ZA200710558B (en) | 2010-04-28 |
| AU2006245440B2 (en) | 2012-04-19 |
| CA2606890A1 (en) | 2006-11-16 |
| CA2606890C (en) | 2014-02-04 |
| PL1885734T3 (pl) | 2015-08-31 |
| WO2006120576A2 (en) | 2006-11-16 |
| PT1885734E (pt) | 2015-03-04 |
| WO2006120576A3 (en) | 2007-07-12 |
| US8062641B2 (en) | 2011-11-22 |
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