HRP970083A2 - Polysaccharide precipitation process - Google Patents
Polysaccharide precipitation processInfo
- Publication number
- HRP970083A2 HRP970083A2 HR9608546.9A HRP970083A HRP970083A2 HR P970083 A2 HRP970083 A2 HR P970083A2 HR P970083 A HRP970083 A HR P970083A HR P970083 A2 HRP970083 A2 HR P970083A2
- Authority
- HR
- Croatia
- Prior art keywords
- polysaccharides
- polysaccharide
- process according
- salt
- pneumococcus
- Prior art date
Links
- 229920001282 polysaccharide Polymers 0.000 title claims description 77
- 239000005017 polysaccharide Substances 0.000 title claims description 77
- 238000000034 method Methods 0.000 title claims description 30
- 238000001556 precipitation Methods 0.000 title claims description 9
- 150000004676 glycans Chemical class 0.000 title 1
- 150000004804 polysaccharides Chemical class 0.000 claims description 70
- 230000001580 bacterial effect Effects 0.000 claims description 11
- 239000003599 detergent Substances 0.000 claims description 11
- 229960005486 vaccine Drugs 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 108090000623 proteins and genes Proteins 0.000 claims description 10
- 102000004169 proteins and genes Human genes 0.000 claims description 10
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 8
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 8
- 230000021615 conjugation Effects 0.000 claims description 7
- 238000001212 derivatisation Methods 0.000 claims description 7
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- -1 Polysaccharide salt Chemical class 0.000 claims description 4
- 229940037003 alum Drugs 0.000 claims description 4
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 229920001586 anionic polysaccharide Polymers 0.000 claims description 3
- 150000004836 anionic polysaccharides Chemical class 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 241000606790 Haemophilus Species 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000002163 immunogen Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 101000597577 Gluconacetobacter diazotrophicus (strain ATCC 49037 / DSM 5601 / CCUG 37298 / CIP 103539 / LMG 7603 / PAl5) Outer membrane protein Proteins 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000872 buffer Substances 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical class CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000011026 diafiltration Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000005137 deposition process Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- BWLMCOKQHQOEEE-BYPYZUCNSA-N (2s)-2-amino-4-(carboxymethylsulfanyl)butanoic acid Chemical compound OC(=O)[C@@H](N)CCSCC(O)=O BWLMCOKQHQOEEE-BYPYZUCNSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010052285 Membrane Proteins Proteins 0.000 description 2
- 101150044960 PSPN gene Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 229940049548 pneumovax Drugs 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000005549 size reduction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 108010060123 Conjugate Vaccines Proteins 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 108010067390 Viral Proteins Proteins 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005864 bromoacetylation reaction Methods 0.000 description 1
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 229960004830 cetylpyridinium Drugs 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229940031670 conjugate vaccine Drugs 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229940099500 cystamine Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940009976 deoxycholate Drugs 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000012806 monitoring device Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229940031999 pneumococcal conjugate vaccine Drugs 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 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
- 230000007704 transition Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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
- A61K39/102—Pasteurellales, e.g. Actinobacillus, Pasteurella; Haemophilus
-
- 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
- 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
-
- 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
- A61K2039/55505—Inorganic adjuvants
-
- 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
- A61K2039/6068—Other bacterial proteins, e.g. OMP
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1163196P | 1996-02-14 | 1996-02-14 | |
| GB9608546A GB9608546D0 (en) | 1996-04-25 | 1996-04-25 | Polysaccharide precipitation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP970083A2 true HRP970083A2 (en) | 1998-04-30 |
Family
ID=26309205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR9608546.9A HRP970083A2 (en) | 1996-02-14 | 1997-02-13 | Polysaccharide precipitation process |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0897427B1 (de) |
| JP (1) | JP3990455B2 (de) |
| AR (1) | AR005869A1 (de) |
| AT (1) | ATE280834T1 (de) |
| AU (1) | AU724862B2 (de) |
| CA (1) | CA2245588C (de) |
| DE (1) | DE69731380T2 (de) |
| DK (1) | DK0897427T3 (de) |
| ES (1) | ES2229336T3 (de) |
| HR (1) | HRP970083A2 (de) |
| PT (1) | PT897427E (de) |
| TW (1) | TW411344B (de) |
| WO (1) | WO1997030171A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0115176D0 (en) | 2001-06-20 | 2001-08-15 | Chiron Spa | Capular polysaccharide solubilisation and combination vaccines |
| US20070184072A1 (en) * | 2005-04-08 | 2007-08-09 | Wyeth | Multivalent pneumococcal polysaccharide-protein conjugate composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2388563A1 (fr) * | 1977-04-29 | 1978-11-24 | Fabre Sa Pierre | Vaccins acellulaires perfectionnes contenant des polysaccharides capsulaires |
| BE889979A (fr) * | 1981-08-14 | 1982-02-15 | Smith Kline Rit | Procede de preparation de polysaccharides bacteriens capsulaires antigeniques purifies, produits obtenus et leur utilisation |
| US4686102A (en) * | 1984-04-12 | 1987-08-11 | American Cyanamid Company | Multivalent pneumococcal vaccine and preparation thereof |
| 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 |
| US4877613A (en) * | 1987-08-05 | 1989-10-31 | Biotech Connections, Inc. | Process for preparing veterinary acellular vaccines against gram-negative nonenteric pathogenic bacilli |
| US5192540A (en) * | 1988-04-19 | 1993-03-09 | American Cyanamid Company | Haemophilus influenzae type b oxidized polysaccharide-outer membrane protein conjugate vaccine |
| SK18594A3 (en) * | 1991-08-16 | 1994-08-10 | Merck & Co Inc | Method of production of capsular polysacharide without lipid and endotoxine |
| US5371197A (en) * | 1991-09-24 | 1994-12-06 | Merck & Co., Inc. | Protein-dimeric polysaccharide conjugate vaccine |
| US5445817A (en) * | 1992-08-21 | 1995-08-29 | The United States Of America As Represented By The Department Of Health And Human Services | Pertussis toxin used as a carrier protein with non-charged saccharides in conjugate vaccines |
-
1997
- 1997-02-10 DK DK97906903T patent/DK0897427T3/da active
- 1997-02-10 ES ES97906903T patent/ES2229336T3/es not_active Expired - Lifetime
- 1997-02-10 AT AT97906903T patent/ATE280834T1/de active
- 1997-02-10 PT PT97906903T patent/PT897427E/pt unknown
- 1997-02-10 WO PCT/US1997/002124 patent/WO1997030171A1/en active IP Right Grant
- 1997-02-10 EP EP97906903A patent/EP0897427B1/de not_active Expired - Lifetime
- 1997-02-10 JP JP52943597A patent/JP3990455B2/ja not_active Expired - Fee Related
- 1997-02-10 DE DE69731380T patent/DE69731380T2/de not_active Expired - Lifetime
- 1997-02-10 AU AU22677/97A patent/AU724862B2/en not_active Ceased
- 1997-02-10 CA CA002245588A patent/CA2245588C/en not_active Expired - Fee Related
- 1997-02-12 AR ARP970100560A patent/AR005869A1/es active IP Right Grant
- 1997-02-13 HR HR9608546.9A patent/HRP970083A2/hr not_active Application Discontinuation
- 1997-02-13 TW TW086101813A patent/TW411344B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69731380T2 (de) | 2006-02-23 |
| DK0897427T3 (da) | 2005-02-14 |
| AU724862B2 (en) | 2000-10-05 |
| ATE280834T1 (de) | 2004-11-15 |
| EP0897427B1 (de) | 2004-10-27 |
| AR005869A1 (es) | 1999-07-21 |
| CA2245588C (en) | 2006-05-09 |
| PT897427E (pt) | 2005-01-31 |
| AU2267797A (en) | 1997-09-02 |
| CA2245588A1 (en) | 1997-08-21 |
| JP2000506383A (ja) | 2000-05-30 |
| JP3990455B2 (ja) | 2007-10-10 |
| WO1997030171A1 (en) | 1997-08-21 |
| EP0897427A1 (de) | 1999-02-24 |
| TW411344B (en) | 2000-11-11 |
| DE69731380D1 (de) | 2004-12-02 |
| ES2229336T3 (es) | 2005-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODBC | Application rejected |