NO323870B1 - Fremgangsmate for a konjugere et peptid til et polysakkarid. - Google Patents
Fremgangsmate for a konjugere et peptid til et polysakkarid. Download PDFInfo
- Publication number
- NO323870B1 NO323870B1 NO19984341A NO984341A NO323870B1 NO 323870 B1 NO323870 B1 NO 323870B1 NO 19984341 A NO19984341 A NO 19984341A NO 984341 A NO984341 A NO 984341A NO 323870 B1 NO323870 B1 NO 323870B1
- Authority
- NO
- Norway
- Prior art keywords
- polysaccharide
- peptide
- conjugate
- group
- amino
- Prior art date
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 181
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 157
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 157
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 123
- 238000000034 method Methods 0.000 title claims abstract description 41
- 230000001268 conjugating effect Effects 0.000 title claims description 3
- 230000008569 process Effects 0.000 title abstract description 3
- -1 amino, hydroxyl Chemical group 0.000 claims abstract description 36
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims abstract description 28
- 150000004804 polysaccharides Polymers 0.000 claims abstract description 24
- 125000006850 spacer group Chemical group 0.000 claims abstract description 21
- 230000021615 conjugation Effects 0.000 claims abstract description 18
- 125000003277 amino group Chemical group 0.000 claims description 33
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000000524 functional group Chemical group 0.000 claims description 15
- 125000000539 amino acid group Chemical group 0.000 claims description 11
- 238000001212 derivatisation Methods 0.000 claims description 11
- 229920001184 polypeptide Polymers 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 230000001419 dependent effect Effects 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 7
- PVGATNRYUYNBHO-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(2,5-dioxopyrrol-1-yl)butanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCCN1C(=O)C=CC1=O PVGATNRYUYNBHO-UHFFFAOYSA-N 0.000 claims description 6
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims description 6
- 230000001588 bifunctional effect Effects 0.000 claims description 6
- 230000001580 bacterial effect Effects 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 4
- 210000004899 c-terminal region Anatomy 0.000 claims description 4
- 239000002158 endotoxin Substances 0.000 claims description 4
- 229920006008 lipopolysaccharide Polymers 0.000 claims description 4
- 125000003047 N-acetyl group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- LLXVXPPXELIDGQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(2,5-dioxopyrrol-1-yl)benzoate Chemical compound C=1C=CC(N2C(C=CC2=O)=O)=CC=1C(=O)ON1C(=O)CCC1=O LLXVXPPXELIDGQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- JJAHTWIKCUJRDK-UHFFFAOYSA-N succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate Chemical compound C1CC(CN2C(C=CC2=O)=O)CCC1C(=O)ON1C(=O)CCC1=O JJAHTWIKCUJRDK-UHFFFAOYSA-N 0.000 claims description 2
- PMJWDPGOWBRILU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[4-(2,5-dioxopyrrol-1-yl)phenyl]butanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCCC(C=C1)=CC=C1N1C(=O)C=CC1=O PMJWDPGOWBRILU-UHFFFAOYSA-N 0.000 claims 1
- 239000000562 conjugate Substances 0.000 abstract description 49
- 125000005647 linker group Chemical group 0.000 abstract description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 18
- 230000028993 immune response Effects 0.000 abstract description 14
- 230000002163 immunogen Effects 0.000 abstract description 9
- 229920001231 Polysaccharide peptide Polymers 0.000 abstract description 8
- 239000000863 peptide conjugate Substances 0.000 abstract description 7
- 108010022457 polysaccharide peptide Proteins 0.000 abstract description 7
- 230000001681 protective effect Effects 0.000 abstract description 4
- 230000007774 longterm Effects 0.000 abstract description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract description 2
- 244000000010 microbial pathogen Species 0.000 abstract description 2
- 229960002317 succinimide Drugs 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- 239000002671 adjuvant Substances 0.000 description 20
- 235000018102 proteins Nutrition 0.000 description 19
- 102000004169 proteins and genes Human genes 0.000 description 19
- 108090000623 proteins and genes Proteins 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000427 antigen Substances 0.000 description 13
- 102000036639 antigens Human genes 0.000 description 13
- 108091007433 antigens Proteins 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 11
- 229960005486 vaccine Drugs 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000193998 Streptococcus pneumoniae Species 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000003172 aldehyde group Chemical group 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 5
- 230000007717 exclusion Effects 0.000 description 5
- 230000005847 immunogenicity Effects 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000005875 antibody response Effects 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 4
- 210000000987 immune system Anatomy 0.000 description 4
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000947238 Neisseria meningitidis serogroup C Species 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003275 alpha amino acid group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006268 reductive amination reaction Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 102000014914 Carrier Proteins Human genes 0.000 description 2
- 108010078791 Carrier Proteins Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 241000921898 Neisseria meningitidis serogroup A Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 229920002684 Sepharose Polymers 0.000 description 2
- 241000194019 Streptococcus mutans Species 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 2
- 206010013023 diphtheria Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- 230000003053 immunization Effects 0.000 description 2
- 238000002649 immunization Methods 0.000 description 2
- 230000006054 immunological memory Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229960003151 mercaptamine Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 230000037452 priming Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- NKUZQMZWTZAPSN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-bromoacetate Chemical compound BrCC(=O)ON1C(=O)CCC1=O NKUZQMZWTZAPSN-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- SGNXVBOIDPPRJJ-PSASIEDQSA-N 1-[(1r,6r)-9-azabicyclo[4.2.1]non-4-en-5-yl]ethanone Chemical compound CC(=O)C1=CCC[C@@H]2CC[C@H]1N2 SGNXVBOIDPPRJJ-PSASIEDQSA-N 0.000 description 1
- AASYSXRGODIQGY-UHFFFAOYSA-N 1-[1-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(CCCCC)N1C(=O)C=CC1=O AASYSXRGODIQGY-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- VOUAQYXWVJDEQY-QENPJCQMSA-N 33017-11-7 Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)NCC(=O)NCC(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)CCC1 VOUAQYXWVJDEQY-QENPJCQMSA-N 0.000 description 1
- AIHDUTVBOYDXOW-UHFFFAOYSA-N 4-(dimethylamino)pyridin-1-ium-1-carbonitrile Chemical compound CN(C)C1=CC=[N+](C#N)C=C1 AIHDUTVBOYDXOW-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 108010075254 C-Peptide Proteins 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 201000007336 Cryptococcosis Diseases 0.000 description 1
- 241000221204 Cryptococcus neoformans Species 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 108010053187 Diphtheria Toxin Proteins 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 241000606790 Haemophilus Species 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- 241000588650 Neisseria meningitidis Species 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 241000607764 Shigella dysenteriae Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 108010055044 Tetanus Toxin Proteins 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 241001467018 Typhis Species 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- 239000002253 acid Chemical group 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000000240 adjuvant effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003948 anatoxin Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
- 229940099500 cystamine Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical group OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 235000004400 serine Nutrition 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 125000005629 sialic acid group Chemical group 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940118376 tetanus toxin Drugs 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 235000008521 threonine Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 235000002374 tyrosine Nutrition 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/646—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent the entire peptide or protein drug conjugate elicits an immune response, e.g. conjugate vaccines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97100884 | 1997-01-21 | ||
| PCT/EP1998/000654 WO1998031393A2 (en) | 1997-01-21 | 1998-01-21 | Polysaccharide-peptide-conjugates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO984341D0 NO984341D0 (no) | 1998-09-18 |
| NO984341L NO984341L (no) | 1998-11-11 |
| NO323870B1 true NO323870B1 (no) | 2007-07-16 |
Family
ID=8226387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19984341A NO323870B1 (no) | 1997-01-21 | 1998-09-18 | Fremgangsmate for a konjugere et peptid til et polysakkarid. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6472506B1 (pt) |
| EP (1) | EP0959905B1 (pt) |
| JP (1) | JP4290766B2 (pt) |
| KR (1) | KR100593466B1 (pt) |
| AT (1) | ATE451124T1 (pt) |
| AU (1) | AU722315B2 (pt) |
| CA (1) | CA2246760C (pt) |
| DE (1) | DE69841362D1 (pt) |
| DK (1) | DK0959905T3 (pt) |
| ES (1) | ES2335557T3 (pt) |
| NO (1) | NO323870B1 (pt) |
| NZ (1) | NZ331578A (pt) |
| PT (1) | PT959905E (pt) |
| WO (1) | WO1998031393A2 (pt) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040001842A1 (en) * | 1997-05-12 | 2004-01-01 | Dov Michaeli | Immunogenic compositions to the CCK-B/gastrin receptor and methods for the treatment of tumors |
| DE19821859A1 (de) * | 1998-05-15 | 1999-12-09 | M Alexander Schmidt | Darstellung immunogener (Kapsel-)Polysaccharid-Konjugate durch orientierte Kupplung synthetischer T-Zell-Epitope zur Erzeugung von Vakzinen gegen N.meningitidis |
| US7223845B2 (en) | 1998-06-16 | 2007-05-29 | The Board Of Regents Of The University Of Oklahoma | Synthetic glycosulfopeptides and methods of synthesis thereof |
| AU773542B2 (en) * | 1998-06-16 | 2004-05-27 | Board Of Regents Of The University Of Oklahoma, The | Glycosulfopeptides and methods of synthesis and use thereof |
| US6858211B1 (en) * | 1998-07-20 | 2005-02-22 | The United States Of America As Represented By The Department Of Health And Human Services | Vaccines against Escherichia coli O157 infection |
| US7723296B2 (en) | 2001-01-18 | 2010-05-25 | Genzyme Corporation | Methods for introducing mannose-6-phosphate and other oligosaccharides onto glycoproteins and its application thereof |
| YU66103A (sh) * | 2001-01-23 | 2006-05-25 | Aventis Pasteur | Vakcina multivalentnog konjugata meningokokalnog polisaharid-proteina |
| US20030091574A1 (en) | 2001-03-23 | 2003-05-15 | Gevas Philip C. | Combination treatment of pancreatic cancer |
| US20090191232A1 (en) | 2001-05-04 | 2009-07-30 | Gevas Philip C | Combination therapy for the treatment of tumors |
| US20030035806A1 (en) * | 2001-05-11 | 2003-02-20 | D'ambra Anello J. | Novel meningitis conjugate vaccine |
| GB0115176D0 (en) | 2001-06-20 | 2001-08-15 | Chiron Spa | Capular polysaccharide solubilisation and combination vaccines |
| GB0220198D0 (en) * | 2002-08-30 | 2002-10-09 | Chiron Spa | Modified saccharides,conjugates thereof and their manufacture |
| US6695447B1 (en) | 2002-09-30 | 2004-02-24 | Eastman Kodak Company | Ink jet recording element |
| US20050118199A1 (en) * | 2003-10-07 | 2005-06-02 | Esser Mark T. | Process for covalently conjugating polysaccharides to microspheres or biomolecules |
| WO2006032980A1 (en) | 2004-09-22 | 2006-03-30 | Receptor Biologix, Inc. | Monoclonal antibolies to progastrin |
| TWI264608B (en) * | 2005-04-08 | 2006-10-21 | Delta Electronics Inc | Light tunnel module |
| ES2346693T3 (es) * | 2005-10-06 | 2010-10-19 | Nestec S.A. | Enterococos probioticos que permiten mejorar la unidad. |
| TW200745163A (en) * | 2006-02-17 | 2007-12-16 | Syntonix Pharmaceuticals Inc | Peptides that block the binding of IgG to FcRn |
| FR2899110A1 (fr) * | 2006-03-31 | 2007-10-05 | Sanofi Pasteur Sa | Polysaccharides capsulaires de type 5 et de type 8 des souches surproductrices de staphylococcus aureus |
| LT2457920T (lt) | 2007-01-18 | 2018-02-12 | Genzyme Corporation | Oligosacharidai, apimantys aminooksigrupę, ir jų konjugatai |
| EA201070231A1 (ru) * | 2007-08-09 | 2010-10-29 | Синтоникс Фармасьютикалз, Инк. | Иммуномодулирующие пептиды |
| JP2009242372A (ja) * | 2008-03-11 | 2009-10-22 | Yokohama City Univ | 均一な糖鎖構造を有するエリスロポエチン誘導体 |
| WO2010014909A1 (en) * | 2008-08-01 | 2010-02-04 | Syntonix Pharmaceuticals, Inc. | Immunomodulatory peptides |
| JP5658167B2 (ja) | 2008-12-16 | 2015-01-21 | ジェンザイム・コーポレーション | オリゴ糖−タンパク複合体 |
| NZ597007A (en) | 2009-05-14 | 2013-09-27 | Sanofi Pasteur | Meningococcus vaccine containing lipooligosaccharide (los) from modified strains of l6 immunotype neisseria meningitidis |
| EP2429658B1 (fr) | 2009-05-14 | 2016-04-20 | Sanofi Pasteur | Procédé pour adjuver le lipopolysaccharide (LPS) des bactéries à gram-négatif |
| GB201003922D0 (en) | 2010-03-09 | 2010-04-21 | Glaxosmithkline Biolog Sa | Conjugation process |
| WO2013082149A1 (en) | 2011-11-28 | 2013-06-06 | Case Western Reserve University | Polysaccharide therapeutic conjugates |
| WO2015184453A1 (en) | 2014-05-30 | 2015-12-03 | Case Western Reserve University | Retinylamine derivitives for treatment of ocular disorders |
| US11129845B2 (en) | 2014-06-18 | 2021-09-28 | Case Western Reserve University | Compositions and methods for the delivery of nucleic acids |
| US10925980B2 (en) | 2014-08-04 | 2021-02-23 | Case Western Reserve University | Molecular probes and methods of use |
| US11407786B2 (en) | 2015-06-18 | 2022-08-09 | Case Western Reserve University | Compositions and methods for the delivery of nucleic acids |
| WO2018232230A1 (en) | 2017-06-15 | 2018-12-20 | Cancer Advances Inc. | Compositions and methods for inducing humoral and cellular immunities against tumors and cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695624A (en) * | 1984-05-10 | 1987-09-22 | Merck & Co., Inc. | Covalently-modified polyanionic bacterial polysaccharides, stable covalent conjugates of such polysaccharides and immunogenic proteins with bigeneric spacers, and methods of preparing such polysaccharides and conjugates and of confirming covalency |
| NZ214503A (en) | 1984-12-20 | 1990-02-26 | Merck & Co Inc | Covalently-modified neutral bacterial polysaccharides, stable covalent conjugates of such polysaccharides and immunogenic proteins, and methods of preparing such polysaccharides and conjugates |
| EP0326111A3 (en) | 1988-01-29 | 1989-12-27 | New York Blood Center, Inc. | Peptide derivatives rendered immunogenic when administered with alum as an adjuvant |
| CA2047033A1 (en) | 1990-07-19 | 1992-01-20 | Elizabeth E. Sugg | Cyclic hiv principal neutralizing determinant peptides |
-
1998
- 1998-01-21 AT AT98906928T patent/ATE451124T1/de active
- 1998-01-21 NZ NZ331578A patent/NZ331578A/xx not_active IP Right Cessation
- 1998-01-21 US US09/155,077 patent/US6472506B1/en not_active Expired - Fee Related
- 1998-01-21 KR KR1019980707414A patent/KR100593466B1/ko not_active IP Right Cessation
- 1998-01-21 JP JP53376898A patent/JP4290766B2/ja not_active Expired - Fee Related
- 1998-01-21 AU AU62957/98A patent/AU722315B2/en not_active Ceased
- 1998-01-21 DE DE69841362T patent/DE69841362D1/de not_active Expired - Lifetime
- 1998-01-21 ES ES98906928T patent/ES2335557T3/es not_active Expired - Lifetime
- 1998-01-21 PT PT98906928T patent/PT959905E/pt unknown
- 1998-01-21 CA CA2246760A patent/CA2246760C/en not_active Expired - Fee Related
- 1998-01-21 WO PCT/EP1998/000654 patent/WO1998031393A2/en active IP Right Grant
- 1998-01-21 DK DK98906928.1T patent/DK0959905T3/da active
- 1998-01-21 EP EP98906928A patent/EP0959905B1/en not_active Expired - Lifetime
- 1998-09-18 NO NO19984341A patent/NO323870B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2335557T3 (es) | 2010-03-29 |
| DE69841362D1 (de) | 2010-01-21 |
| JP2000507974A (ja) | 2000-06-27 |
| WO1998031393A2 (en) | 1998-07-23 |
| PT959905E (pt) | 2010-02-05 |
| JP4290766B2 (ja) | 2009-07-08 |
| US6472506B1 (en) | 2002-10-29 |
| CA2246760A1 (en) | 1998-07-23 |
| NO984341L (no) | 1998-11-11 |
| EP0959905B1 (en) | 2009-12-09 |
| AU722315B2 (en) | 2000-07-27 |
| AU6295798A (en) | 1998-08-07 |
| CA2246760C (en) | 2012-01-10 |
| NO984341D0 (no) | 1998-09-18 |
| KR20000064696A (ko) | 2000-11-06 |
| EP0959905A2 (en) | 1999-12-01 |
| ATE451124T1 (de) | 2009-12-15 |
| WO1998031393A3 (en) | 1998-09-11 |
| DK0959905T3 (da) | 2010-04-06 |
| NZ331578A (en) | 2000-05-26 |
| KR100593466B1 (ko) | 2007-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2246760C (en) | Polysaccharide-peptide-conjugates | |
| AU771330B2 (en) | Immunogenic beta-propionamido-linked polysaccharide protein conjugate useful as a vaccine produced using an N-acryloylated polysaccharide | |
| CA1340958C (en) | Synthetic peptides representing a t-cell epitope as a carrier molecule for conjugate vaccines | |
| Pozsgay | Oligosaccharide-protein conjugates as vaccine candidates against bacteria | |
| HUT64237A (en) | Improved vaccina preparatives | |
| NO321705B1 (no) | Vaksiner med modifiserte meningokokk/polysakkarid-konjugater | |
| Reichel et al. | Synthetic carbohydrate-based vaccines: synthesis of an L-glycero-D-manno-heptose antigen–T-epitope–lipopeptide conjugate | |
| CA2249409C (en) | Iga1 protease fragment as carrier peptide | |
| MXPA98007617A (es) | Conjugados de polisacaridos peptidos | |
| RU2249463C2 (ru) | Иммуногенный конъюгат бета-пропионамид-связанного полисахарида с белком, использующийся в качестве вакцины | |
| WO1998031791A9 (en) | Iga1 protease fragment as carrier peptide | |
| AU779038B2 (en) | IGA1 protease fragment as carrier peptide | |
| MXPA98007634A (en) | Iga1 protease fragment as carrier peptide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |