CA2153733A1 - Compositions immunogenes a base d'oligosaccharides - Google Patents
Compositions immunogenes a base d'oligosaccharidesInfo
- Publication number
- CA2153733A1 CA2153733A1 CA002153733A CA2153733A CA2153733A1 CA 2153733 A1 CA2153733 A1 CA 2153733A1 CA 002153733 A CA002153733 A CA 002153733A CA 2153733 A CA2153733 A CA 2153733A CA 2153733 A1 CA2153733 A1 CA 2153733A1
- Authority
- CA
- Canada
- Prior art keywords
- polysaccharide
- conjugate
- carrier
- composition
- oligosaccharide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 131
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 130
- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 230000002163 immunogen Effects 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 51
- 229920001282 polysaccharide Polymers 0.000 claims description 131
- 239000005017 polysaccharide Substances 0.000 claims description 131
- 150000004676 glycans Chemical class 0.000 claims description 120
- 150000001720 carbohydrates Chemical class 0.000 claims description 41
- 238000005859 coupling reaction Methods 0.000 claims description 38
- 238000010168 coupling process Methods 0.000 claims description 37
- 230000008878 coupling Effects 0.000 claims description 34
- 238000002965 ELISA Methods 0.000 claims description 31
- 230000001580 bacterial effect Effects 0.000 claims description 27
- 238000003556 assay Methods 0.000 claims description 26
- 230000005764 inhibitory process Effects 0.000 claims description 25
- 239000002671 adjuvant Substances 0.000 claims description 20
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 18
- 230000001629 suppression Effects 0.000 claims description 15
- 230000014207 opsonization Effects 0.000 claims description 12
- 230000001681 protective effect Effects 0.000 claims description 12
- 230000000890 antigenic effect Effects 0.000 claims description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 230000005847 immunogenicity Effects 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 244000052616 bacterial pathogen Species 0.000 claims description 5
- 230000003612 virological effect Effects 0.000 claims description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 5
- 230000003053 immunization Effects 0.000 claims 1
- 238000002649 immunization Methods 0.000 claims 1
- 102000014914 Carrier Proteins Human genes 0.000 abstract description 8
- 108010078791 Carrier Proteins Proteins 0.000 abstract description 8
- 230000009851 immunogenic response Effects 0.000 abstract 1
- 230000004044 response Effects 0.000 description 74
- 239000000427 antigen Substances 0.000 description 54
- 108091007433 antigens Proteins 0.000 description 54
- 102000036639 antigens Human genes 0.000 description 54
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 48
- 235000014633 carbohydrates Nutrition 0.000 description 30
- 241000699670 Mus sp. Species 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 210000002966 serum Anatomy 0.000 description 27
- 229960005486 vaccine Drugs 0.000 description 27
- 229960000814 tetanus toxoid Drugs 0.000 description 26
- 102000004169 proteins and genes Human genes 0.000 description 23
- 108090000623 proteins and genes Proteins 0.000 description 23
- 238000000926 separation method Methods 0.000 description 20
- 229940031670 conjugate vaccine Drugs 0.000 description 19
- 108010060123 Conjugate Vaccines Proteins 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- 230000005875 antibody response Effects 0.000 description 17
- 239000000969 carrier Substances 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 14
- 210000001541 thymus gland Anatomy 0.000 description 14
- 241000193998 Streptococcus pneumoniae Species 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 13
- 241000588650 Neisseria meningitidis Species 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
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- 230000009467 reduction Effects 0.000 description 11
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- 239000000126 substance Substances 0.000 description 11
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- 239000000872 buffer Substances 0.000 description 10
- 230000001419 dependent effect Effects 0.000 description 10
- 241000699666 Mus <mouse, genus> Species 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 244000052769 pathogen Species 0.000 description 8
- 229920000136 polysorbate Polymers 0.000 description 8
- 150000001718 carbodiimides Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 229960003983 diphtheria toxoid Drugs 0.000 description 7
- 150000002772 monosaccharides Chemical class 0.000 description 7
- 229940049548 pneumovax Drugs 0.000 description 7
- 241000283973 Oryctolagus cuniculus Species 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 6
- -1 alkyl compound Chemical class 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 239000002344 surface layer Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000606768 Haemophilus influenzae Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000282320 Panthera leo Species 0.000 description 5
- 239000006161 blood agar Substances 0.000 description 5
- 206010013023 diphtheria Diseases 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000413 hydrolysate Substances 0.000 description 5
- 230000002480 immunoprotective effect Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
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- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000003053 toxin Substances 0.000 description 5
- 231100000765 toxin Toxicity 0.000 description 5
- 108700012359 toxins Proteins 0.000 description 5
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 4
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241001505901 Streptococcus sp. 'group A' Species 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 238000005341 cation exchange Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 229940047650 haemophilus influenzae Drugs 0.000 description 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 230000002018 overexpression Effects 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 description 4
- 229940124733 pneumococcal vaccine Drugs 0.000 description 4
- 230000000069 prophylactic effect Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 108010059892 Cellulase Proteins 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 101710116435 Outer membrane protein Proteins 0.000 description 3
- 241000193990 Streptococcus sp. 'group B' Species 0.000 description 3
- 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 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000036755 cellular response Effects 0.000 description 3
- 229940106157 cellulase Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 230000000295 complement effect Effects 0.000 description 3
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- 230000001939 inductive effect Effects 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
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- 230000001662 opsonic effect Effects 0.000 description 3
- 238000002731 protein assay Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 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 3
- 239000011534 wash buffer Substances 0.000 description 3
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 2
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
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- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 description 2
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- FYGDTMLNYKFZSV-DZOUCCHMSA-N alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-DZOUCCHMSA-N 0.000 description 2
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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- 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
- 230000008733 trauma Effects 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/02—Bacterial antigens
- A61K39/09—Lactobacillales, e.g. aerococcus, enterococcus, lactobacillus, lactococcus, streptococcus
- A61K39/092—Streptococcus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/55583—Polysaccharides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002153733A CA2153733A1 (fr) | 1995-07-12 | 1995-07-12 | Compositions immunogenes a base d'oligosaccharides |
| NZ337730A NZ337730A (en) | 1995-06-07 | 1996-06-06 | use of an oligosaccharide hapten- carrier conjugate for immunizing against a bacterial or viral pathogen by administering |
| IL12158596A IL121585A0 (en) | 1995-06-07 | 1996-06-06 | Immunogenic and immunostimulatory oligosaccharide compositions and methods of preparing and using them |
| KR1019970707283A KR19990007777A (ko) | 1995-06-07 | 1996-06-06 | 면역성 및 면역자극성 올리고당 조성물 및 이를 제조하고 이용하는 방법 |
| EP96917311A EP0831894A1 (fr) | 1995-06-07 | 1996-06-06 | Compositions oligasaccharidiques immunogenes et immunostimulatrices et leurs procedes de production et d'utilisations |
| AU59944/96A AU725279B2 (en) | 1995-06-07 | 1996-06-06 | Immunogenic and immunostimulatory oligosaccharide compositions and methods of making and using them |
| JP9500049A JPH11506110A (ja) | 1995-06-07 | 1996-06-06 | 免疫原性および免疫刺激性オリゴサッカライド組成物ならびにそれらの作製法および使用法 |
| CZ973278A CZ327897A3 (cs) | 1995-06-07 | 1996-06-06 | Imunogenní a imunostimulační oligosacharidové kompozice, způsoby jejich přípravy a použití |
| NZ309713A NZ309713A (en) | 1995-06-07 | 1996-06-06 | Oligosaccharides of S pneumoniae serotype 8 and their use in a vaccine |
| PCT/CA1996/000387 WO1996040225A1 (fr) | 1995-06-07 | 1996-06-06 | Compositions oligasaccharidiques immunogenes et immunostimulatrices et leurs procedes de production et d'utilisations |
| NO974727A NO974727L (no) | 1995-06-07 | 1997-10-13 | Immunogene og immunostimulatoriske oligosakkarid sammensetninger og fremgangsmåter for fremstilling derav |
| MX9707944A MX9707944A (es) | 1995-06-07 | 1997-10-15 | Composiciones de oligosacaridos inmunigenicos e inmunoestimulatorios y metodos para fabricarlos y utilizarlos. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002153733A CA2153733A1 (fr) | 1995-07-12 | 1995-07-12 | Compositions immunogenes a base d'oligosaccharides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2153733A1 true CA2153733A1 (fr) | 1997-01-13 |
Family
ID=4156211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002153733A Abandoned CA2153733A1 (fr) | 1995-06-07 | 1995-07-12 | Compositions immunogenes a base d'oligosaccharides |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2153733A1 (fr) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11123417B2 (en) | 2018-02-05 | 2021-09-21 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11147864B2 (en) | 2018-02-05 | 2021-10-19 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| EP3678694A4 (fr) * | 2017-09-07 | 2021-10-20 | Merck Sharp & Dohme Corp. | Procédés de formulation de polysaccharides pneumococciques pour conjugaison à une protéine porteuse |
| US11224652B2 (en) | 2016-08-05 | 2022-01-18 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11241489B2 (en) | 2016-08-05 | 2022-02-08 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11400162B2 (en) | 2017-02-24 | 2022-08-02 | Merck Sharp & Dohme Llc | Processes for the formulation of pneumococcal polysaccharides for conjugation to a carrier protein |
| US11951162B2 (en) | 2018-04-18 | 2024-04-09 | Sk Bioscience Co., Ltd. | Streptococcus pneumoniae capsular polysaccharides and immunogenic conjugate thereof |
-
1995
- 1995-07-12 CA CA002153733A patent/CA2153733A1/fr not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11224652B2 (en) | 2016-08-05 | 2022-01-18 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11241489B2 (en) | 2016-08-05 | 2022-02-08 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11400162B2 (en) | 2017-02-24 | 2022-08-02 | Merck Sharp & Dohme Llc | Processes for the formulation of pneumococcal polysaccharides for conjugation to a carrier protein |
| EP3678694A4 (fr) * | 2017-09-07 | 2021-10-20 | Merck Sharp & Dohme Corp. | Procédés de formulation de polysaccharides pneumococciques pour conjugaison à une protéine porteuse |
| US11123417B2 (en) | 2018-02-05 | 2021-09-21 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11147864B2 (en) | 2018-02-05 | 2021-10-19 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11911452B2 (en) | 2018-02-05 | 2024-02-27 | Sanofi Pasteur Inc. | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US11951162B2 (en) | 2018-04-18 | 2024-04-09 | Sk Bioscience Co., Ltd. | Streptococcus pneumoniae capsular polysaccharides and immunogenic conjugate thereof |
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| Date | Code | Title | Description |
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| FZDE | Dead |
Effective date: 20060228 |