CA2512847C - Conjugates obtained by reductive amination of serotype 5 pneumococcus capsular polysaccharide - Google Patents
Conjugates obtained by reductive amination of serotype 5 pneumococcus capsular polysaccharide Download PDFInfo
- Publication number
- CA2512847C CA2512847C CA2512847A CA2512847A CA2512847C CA 2512847 C CA2512847 C CA 2512847C CA 2512847 A CA2512847 A CA 2512847A CA 2512847 A CA2512847 A CA 2512847A CA 2512847 C CA2512847 C CA 2512847C
- Authority
- CA
- Canada
- Prior art keywords
- polysaccharide
- formula
- reductive amination
- conjugate
- aminated
- 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.)
- Expired - Lifetime
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 299
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 287
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 279
- 238000006268 reductive amination reaction Methods 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 79
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 230000002829 reductive effect Effects 0.000 claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 claims abstract description 30
- 238000001228 spectrum Methods 0.000 claims abstract description 20
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims abstract description 13
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 56
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 56
- 229920001184 polypeptide Polymers 0.000 claims description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 44
- 150000003141 primary amines Chemical group 0.000 claims description 22
- NTBYIQWZAVDRHA-JGWLITMVSA-N (2r,3r,4r,5r)-2-amino-3,4,5-trihydroxyhexanal Chemical compound C[C@@H](O)[C@@H](O)[C@H](O)[C@@H](N)C=O NTBYIQWZAVDRHA-JGWLITMVSA-N 0.000 claims description 21
- 125000006850 spacer group Chemical group 0.000 claims description 21
- 239000003638 chemical reducing agent Substances 0.000 claims description 19
- -1 cyanoborohydride Chemical group 0.000 claims description 19
- TVTGZVYLUHVBAJ-UHFFFAOYSA-N UNPD122247 Natural products CC1OC(O)C(N)C(O)C1O TVTGZVYLUHVBAJ-UHFFFAOYSA-N 0.000 claims description 17
- NTBYIQWZAVDRHA-ARQDHWQXSA-N pneumosamine Chemical compound C[C@@H](O)[C@H](O)[C@H](O)[C@H](N)C=O NTBYIQWZAVDRHA-ARQDHWQXSA-N 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 15
- NTBYIQWZAVDRHA-KCDKBNATSA-N (2s,3s,4r,5s)-2-amino-3,4,5-trihydroxyhexanal Chemical compound C[C@H](O)[C@@H](O)[C@@H](O)[C@H](N)C=O NTBYIQWZAVDRHA-KCDKBNATSA-N 0.000 claims description 14
- 239000002262 Schiff base Substances 0.000 claims description 14
- 150000004753 Schiff bases Chemical class 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 14
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 13
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- 125000003172 aldehyde group Chemical group 0.000 claims description 10
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- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
-
- 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
- A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
- A61K2039/6031—Proteins
- A61K2039/6037—Bacterial toxins, e.g. diphteria toxoid [DT], tetanus toxoid [TT]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Microbiology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Mycology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR03/00488 | 2003-01-17 | ||
| FR0300488A FR2850106B1 (fr) | 2003-01-17 | 2003-01-17 | Conjugues obtenus par amination reductrice du polysaccharide capsulaire du pneumocoque de serotype 5 |
| PCT/FR2004/000089 WO2004067574A1 (fr) | 2003-01-17 | 2004-01-16 | Conjugues obtenus par amination reductrice du polysaccharide capsulaire du pneumocoque de serotype 5 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2512847A1 CA2512847A1 (en) | 2004-08-12 |
| CA2512847C true CA2512847C (en) | 2012-08-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2512847A Expired - Lifetime CA2512847C (en) | 2003-01-17 | 2004-01-16 | Conjugates obtained by reductive amination of serotype 5 pneumococcus capsular polysaccharide |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7812006B2 (enExample) |
| EP (1) | EP1590373B1 (enExample) |
| KR (1) | KR101044437B1 (enExample) |
| AT (1) | ATE520718T1 (enExample) |
| AU (1) | AU2004207647B2 (enExample) |
| BR (1) | BRPI0406819B1 (enExample) |
| CA (1) | CA2512847C (enExample) |
| DK (1) | DK1590373T3 (enExample) |
| FR (1) | FR2850106B1 (enExample) |
| IL (1) | IL169689A0 (enExample) |
| MX (1) | MXPA05007533A (enExample) |
| NZ (1) | NZ541254A (enExample) |
| WO (1) | WO2004067574A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7527797B1 (en) | 2000-09-01 | 2009-05-05 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Vibrio cholerae 0139 conjugate vaccines |
| EP2425853A1 (en) * | 2005-04-08 | 2012-03-07 | Wyeth LLC | Multivalent Pneumococcal Polysaccharide-Protein Conjugate Composition |
| US20070184072A1 (en) | 2005-04-08 | 2007-08-09 | Wyeth | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US7709001B2 (en) | 2005-04-08 | 2010-05-04 | Wyeth Llc | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US7955605B2 (en) | 2005-04-08 | 2011-06-07 | Wyeth Llc | Multivalent pneumococcal polysaccharide-protein conjugate composition |
| US8808707B1 (en) | 2006-05-08 | 2014-08-19 | Wyeth Llc | Pneumococcal dosing regimen |
| US9522382B2 (en) * | 2011-09-06 | 2016-12-20 | Biologistics Llc | Affinity/lectin chromatography methods |
| EP2755683B1 (en) * | 2011-09-14 | 2019-04-03 | GlaxoSmithKline Biologicals SA | Methods for making saccharide-protein glycoconjugates |
| US9815886B2 (en) | 2014-10-28 | 2017-11-14 | Adma Biologics, Inc. | Compositions and methods for the treatment of immunodeficiency |
| EP3303357B1 (en) * | 2015-06-08 | 2021-05-12 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Vaccines against streptococcus pneumoniae serotype 5 |
| MX2019007910A (es) | 2016-12-30 | 2019-12-05 | Sutrovax Inc | Conjugados de polipeptido-antigeno con aminoacidos no naturales. |
| US11951165B2 (en) | 2016-12-30 | 2024-04-09 | Vaxcyte, Inc. | Conjugated vaccine carrier proteins |
| WO2018156467A1 (en) * | 2017-02-24 | 2018-08-30 | Merck Sharp & Dohme Corp. | Methods for improving filterability of polysaccharide-protein conjugate reactions |
| US10259865B2 (en) | 2017-03-15 | 2019-04-16 | Adma Biologics, Inc. | Anti-pneumococcal hyperimmune globulin for the treatment and prevention of pneumococcal infection |
| BR112020011414B8 (pt) | 2017-12-06 | 2023-01-31 | Merck Sharp & Dohme | Composições imunogênicas multivalentes compreendendo conjugados de proteína carreadora e polissacarídeo de s. pneumoniae |
| EP3897705A2 (en) | 2018-12-19 | 2021-10-27 | Merck Sharp & Dohme Corp. | Compositions comprising streptococcus pneumoniae polysaccharide-protein conjugates and methods of use thereof |
| US20230405137A1 (en) * | 2020-11-10 | 2023-12-21 | Pfizer Inc. | Immunogenic compositions comprising conjugated capsular saccharide antigens and uses thereof |
| CN120607643B (zh) * | 2025-07-24 | 2026-05-12 | 江苏中慧元通生物科技股份有限公司 | 一种肺炎球菌单价多糖的纯化工艺 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4902506A (en) * | 1983-07-05 | 1990-02-20 | The University Of Rochester | Immunogenic conjugates |
| US4761283A (en) * | 1983-07-05 | 1988-08-02 | The University Of Rochester | Immunogenic conjugates |
| US5153312A (en) * | 1990-09-28 | 1992-10-06 | American Cyanamid Company | Oligosaccharide conjugate vaccines |
| FR2682388B1 (fr) * | 1991-10-10 | 1995-06-09 | Pasteur Merieux Serums Vacc | Procede de preparation d'un oligoside par depolymerisation d'un polyoside issu d'un agent pathogene, oligoside ainsi obtenu et son utilisation notamment comme agent vaccinal. |
| JPH08511007A (ja) | 1993-06-09 | 1996-11-19 | コノート ラボラトリーズ リミテッド | タンデム合成ｈｉｖ−１ペプチド |
| FR2763244B1 (fr) * | 1997-05-14 | 2003-08-01 | Pasteur Merieux Serums Vacc | Composition vaccinale multivalente a porteur mixte |
| EP1035137A1 (en) * | 1999-03-12 | 2000-09-13 | Pasteur Merieux Serums Et Vaccins | Method for the reductive amination of polysaccharides |
| JP2002539273A (ja) | 1999-03-19 | 2002-11-19 | スミスクライン ビーチャム バイオロジカルズ ソシエテ アノニム | ワクチン |
-
2003
- 2003-01-17 FR FR0300488A patent/FR2850106B1/fr not_active Expired - Lifetime
-
2004
- 2004-01-15 US US10/758,142 patent/US7812006B2/en active Active
- 2004-01-16 WO PCT/FR2004/000089 patent/WO2004067574A1/fr not_active Ceased
- 2004-01-16 BR BRPI0406819-0A patent/BRPI0406819B1/pt active IP Right Grant
- 2004-01-16 MX MXPA05007533A patent/MXPA05007533A/es active IP Right Grant
- 2004-01-16 EP EP04702733A patent/EP1590373B1/fr not_active Expired - Lifetime
- 2004-01-16 KR KR1020057013266A patent/KR101044437B1/ko not_active Expired - Lifetime
- 2004-01-16 AU AU2004207647A patent/AU2004207647B2/en not_active Expired
- 2004-01-16 DK DK04702733.9T patent/DK1590373T3/da active
- 2004-01-16 CA CA2512847A patent/CA2512847C/en not_active Expired - Lifetime
- 2004-01-16 AT AT04702733T patent/ATE520718T1/de not_active IP Right Cessation
- 2004-01-16 NZ NZ541254A patent/NZ541254A/en not_active IP Right Cessation
-
2005
- 2005-07-14 IL IL169689A patent/IL169689A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0406819A (pt) | 2005-12-27 |
| KR101044437B1 (ko) | 2011-06-27 |
| WO2004067574A1 (fr) | 2004-08-12 |
| NZ541254A (en) | 2008-07-31 |
| EP1590373B1 (fr) | 2011-08-17 |
| KR20050093838A (ko) | 2005-09-23 |
| US7812006B2 (en) | 2010-10-12 |
| AU2004207647B2 (en) | 2010-07-01 |
| IL169689A0 (en) | 2007-07-04 |
| FR2850106B1 (fr) | 2005-02-25 |
| CA2512847A1 (en) | 2004-08-12 |
| EP1590373A1 (fr) | 2005-11-02 |
| AU2004207647A1 (en) | 2004-08-12 |
| BRPI0406819B1 (pt) | 2017-01-03 |
| FR2850106A1 (fr) | 2004-07-23 |
| BRPI0406819B8 (enExample) | 2021-05-25 |
| DK1590373T3 (da) | 2011-12-05 |
| ATE520718T1 (de) | 2011-09-15 |
| US20040170638A1 (en) | 2004-09-02 |
| MXPA05007533A (es) | 2005-12-05 |
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| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20240116 |