CU22904A1 - Oligosacáridos derivados de ribosa- ribitol-fosfato, métodos para prepararlos, inmunógenos que los comprenden y vacunas que comprenden dichos inmunógenos - Google Patents
Oligosacáridos derivados de ribosa- ribitol-fosfato, métodos para prepararlos, inmunógenos que los comprenden y vacunas que comprenden dichos inmunógenosInfo
- Publication number
- CU22904A1 CU22904A1 CU1999121A CU1999121A CU22904A1 CU 22904 A1 CU22904 A1 CU 22904A1 CU 1999121 A CU1999121 A CU 1999121A CU 1999121 A CU1999121 A CU 1999121A CU 22904 A1 CU22904 A1 CU 22904A1
- Authority
- CU
- Cuba
- Prior art keywords
- immunogens
- vaccines
- methods
- oligosaccharides
- disaccharide
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 10
- 229960005486 vaccine Drugs 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 abstract 7
- 229920001542 oligosaccharide Polymers 0.000 abstract 6
- 150000002482 oligosaccharides Chemical class 0.000 abstract 6
- 150000002016 disaccharides Chemical class 0.000 abstract 4
- 241000606768 Haemophilus influenzae Species 0.000 abstract 3
- 230000015572 biosynthetic process Effects 0.000 abstract 3
- 229940045808 haemophilus influenzae type b Drugs 0.000 abstract 3
- 238000003786 synthesis reaction Methods 0.000 abstract 3
- 150000004676 glycans Chemical class 0.000 abstract 2
- 238000006384 oligomerization reaction Methods 0.000 abstract 2
- 229920001282 polysaccharide Polymers 0.000 abstract 2
- 239000005017 polysaccharide Substances 0.000 abstract 2
- 125000006850 spacer group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000015271 coagulation Effects 0.000 abstract 1
- 238000005345 coagulation Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001514 detection method Methods 0.000 abstract 1
- 238000011026 diafiltration Methods 0.000 abstract 1
- 238000000502 dialysis Methods 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 238000002523 gelfiltration Methods 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 229920002521 macromolecule Polymers 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229960005030 other vaccine in atc Drugs 0.000 abstract 1
- 238000006068 polycondensation reaction Methods 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 238000011002 quantification Methods 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 230000003252 repetitive effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 238000000108 ultra-filtration Methods 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds 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
- A61K39/02—Bacterial antigens
- A61K39/102—Pasteurellales, e.g. Actinobacillus, Pasteurella; Haemophilus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Mycology (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
Abstract
La presente invención se relaciona con una nueva mezcla de oligosacáridos obtenida por síntesis y compuesta por una serie 4,5,6,7,8,....24,25 de al menos cinco sustancias que difieren entre sí solo por n, donde n>4 y <25. Cada componente de la mezcla responde a la estructura 1, que representa la unidad repetitiva del polisacárido capsular del Haemophilus influenzae tipo B como un espaciador para la coagulación a un carrier en uno solo de sus dos extremos (R1 o R2) en una posición predisenada en la síntesis. La invención también se relaciona con los inmunógenos que contienen estas mezclas oligosacarídicas, con las vacunas que contienen esos inmunógenos y a los métodos para preparar estos oligosacáridos en forma de mezclas. Además, la invención contempla el uso de las vacunas ya sean solas o en combinación con otras vacunas para la prevención de las infecciones causadas por el Haemophilus influenzae tipo B. Se describen métodos para sintetizar estas mezclas de oligosacáridos caracterizados porque el proceso de oligomerización es una policondensación en una sola etapa entre el disacárido intermediario, un promotor y el espaciador, donde a través de la manipulación de sus proporciones, el orden de adición y el tiempo de reacción es posible el control de la n promedio, donde n está entre 4 y 25. El proceso de separación de los oligosacáridos inmunológicamente inactivos de la mezcla es un proceso que incluye la diafiltración, ultrafiltración, diálisis, gel filtración o proceso de exclusión molecular relacionados. Se describen también métodos para la síntesis del disacárido intermediario requerido para la oligomerización y que se caracteriza por una dibencilación selectiva aplicada al disacárido 4 que permite su transformación en el disacárido 5 en una sola etapa, lo que hace el proceso más corto y más eficiente. El compuesto 4 es obtenido puro en una secuencia de reacciones de menos de 11 etapas sin recurrir a procesos cromatográficos. Las macromoléculas que contienen la mezcla de oligosacáridos asociadas con un material polimérico se describen igualmente al igual que su uso en la detección y cuantificación de anticuerpos contra el polisacárido capsular del Haemophilus influenzae tipo B.
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CU1999121A CU22904A1 (es) | 1999-08-30 | 1999-08-30 | Oligosacáridos derivados de ribosa- ribitol-fosfato, métodos para prepararlos, inmunógenos que los comprenden y vacunas que comprenden dichos inmunógenos |
| KR1020027002706A KR100818163B1 (ko) | 1999-08-30 | 2000-08-15 | 리보즈-리비톨-인산염의 올리고당 유도체 및 이를포함하는 백신 |
| AT00956040T ATE308551T1 (de) | 1999-08-30 | 2000-08-15 | Oligosaccharide die sich vom ribose-ribtol- phosphat herleiten und impfstoffe, die diese oligosaccharide enthalten |
| DE60023722T DE60023722T2 (de) | 1999-08-30 | 2000-08-15 | Oligosaccharide, die sich vom Ribose-Ribtol-Phosphat herleiten und Impfstoffe, die diese Oligosaccharide enthalten |
| US10/070,101 US6765091B1 (en) | 1999-08-30 | 2000-08-15 | Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them |
| SI200030780T SI1212334T1 (sl) | 1999-08-30 | 2000-08-15 | Oligosaharidi, izvedeni iz riboza-ribitol-fosfata, in vakcine, ki vsebujejo te oligosaharide |
| UA2002021613A UA75579C2 (en) | 1999-08-30 | 2000-08-15 | Process for synthesis of oligosaccharides mixture |
| BRPI0013686A BRPI0013686B8 (pt) | 1999-08-30 | 2000-08-15 | procedimento para sintetizar uma mistura de oligossacarídeos |
| CA2382602A CA2382602C (en) | 1999-08-30 | 2000-08-15 | Oligosaccharides derivatives of ribose-ribitol-phosphate and vaccines containing them |
| PCT/CU2000/000003 WO2001016146A1 (es) | 1999-08-30 | 2000-08-15 | Oligosacáridos derivados de ribosa-ribitol-fosfato y vacunas que los contienen |
| NZ517464A NZ517464A (en) | 1999-08-30 | 2000-08-15 | Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them |
| CNB008134731A CN1205217C (zh) | 1999-08-30 | 2000-08-15 | 核糖－核糖醇－磷酸之寡糖衍生物及含有它们的疫苗 |
| ES00956040T ES2252045T3 (es) | 1999-08-30 | 2000-08-15 | Oligosacaridos derivados de ribosa-ribitol-fosfato y vacunas que los contienen. |
| HK03102864.6A HK1050693B (en) | 1999-08-30 | 2000-08-15 | Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them |
| CZ2002721A CZ2002721A3 (cs) | 1999-08-30 | 2000-08-15 | Směsi oligosacharidů, způsob jejich syntézy a syntézy disacharidu meziproduktu a derivátů disacharidu, imunogen, vakcina, makromolekuly a pouľití disacharidů a makromolekul |
| MXPA02002066A MXPA02002066A (es) | 1999-08-30 | 2000-08-15 | Oligosacaridos derivados de ribosa-ribitol-fosfato y vacunas que los contienen. |
| EP00956040A EP1212334B1 (en) | 1999-08-30 | 2000-08-15 | Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them |
| DK00956040T DK1212334T3 (da) | 1999-08-30 | 2000-08-15 | Oligosaccharidderivater fra ribose-ribitol-fosfat og vacciner indeholdende disse |
| EA200200314A EA005381B1 (ru) | 1999-08-30 | 2000-08-15 | Олигосахаридные производные рибоза-рибит-фосфата и содержащие их вакцины |
| JP2001519710A JP4850377B2 (ja) | 1999-08-30 | 2000-08-15 | リボース−リビトールホスフェートのオリゴ糖誘導体とそれを含むワクチン |
| AU68173/00A AU780816B2 (en) | 1999-08-30 | 2000-08-15 | Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them |
| CO00064095A CO5180646A1 (es) | 1999-08-30 | 2000-08-28 | Procedimiento de sintesis de mezclas de oligosacaridos que comprenden unidades repetitivas de (fosfato-ribosa-ribitol)n o (ribosa-ribitol-fosfato)n |
| ARP000104496A AR025435A1 (es) | 1999-08-30 | 2000-08-29 | Metodo para sintetizar mezclas de oligosacaridos derivados de (fosfato-ribosa-ribitol)n o de (ribosa-ribitol-fosfato)n y disacaridos intermedios de los mismos |
| ZA200201667A ZA200201667B (en) | 1999-08-30 | 2002-02-27 | Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CU1999121A CU22904A1 (es) | 1999-08-30 | 1999-08-30 | Oligosacáridos derivados de ribosa- ribitol-fosfato, métodos para prepararlos, inmunógenos que los comprenden y vacunas que comprenden dichos inmunógenos |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CU22904A1 true CU22904A1 (es) | 2004-01-23 |
Family
ID=5459405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CU1999121A CU22904A1 (es) | 1999-08-30 | 1999-08-30 | Oligosacáridos derivados de ribosa- ribitol-fosfato, métodos para prepararlos, inmunógenos que los comprenden y vacunas que comprenden dichos inmunógenos |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6765091B1 (es) |
| EP (1) | EP1212334B1 (es) |
| JP (1) | JP4850377B2 (es) |
| KR (1) | KR100818163B1 (es) |
| CN (1) | CN1205217C (es) |
| AR (1) | AR025435A1 (es) |
| AT (1) | ATE308551T1 (es) |
| AU (1) | AU780816B2 (es) |
| BR (1) | BRPI0013686B8 (es) |
| CA (1) | CA2382602C (es) |
| CO (1) | CO5180646A1 (es) |
| CU (1) | CU22904A1 (es) |
| CZ (1) | CZ2002721A3 (es) |
| DE (1) | DE60023722T2 (es) |
| DK (1) | DK1212334T3 (es) |
| EA (1) | EA005381B1 (es) |
| ES (1) | ES2252045T3 (es) |
| MX (1) | MXPA02002066A (es) |
| NZ (1) | NZ517464A (es) |
| SI (1) | SI1212334T1 (es) |
| UA (1) | UA75579C2 (es) |
| WO (1) | WO2001016146A1 (es) |
| ZA (1) | ZA200201667B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1713508A2 (en) * | 2004-01-29 | 2006-10-25 | Biosynexus Incorporated | Use of amino-oxy functional groups in the preparation of vaccine conjugates |
| US8647621B2 (en) | 2009-07-27 | 2014-02-11 | Fina Biosolutions, Llc | Method of producing protein-carbohydrate vaccines reduced in free carbohydrate |
| WO2011011879A1 (en) | 2009-07-31 | 2011-02-03 | National Research Council Of Canada | H. pylori lipopolysaccharide outer core epitope |
| US9044517B2 (en) | 2009-12-17 | 2015-06-02 | Fina Biosolutions, Llc | Activation of polysaccharides via the cyanylating agent, 1-cyano-4-pyrrolidinopyridinium tetrafluoroborate (CPPT), in the preparation of polysaccharide/protein conjugate vaccines |
| WO2011133191A1 (en) * | 2010-04-23 | 2011-10-27 | Serum Institute Of India, Ltd. | Simple method for simultaneous removal of multiple impurities from culture supernatants to ultralow levels |
| SG11201811350QA (en) | 2016-07-28 | 2019-01-30 | Max Planck Gesellschaft | Stable hydrolysis-resistant synthetic polyribosylribitolphosphate derivatives as vaccines against haemophilus influenzae type b |
| AU2019239890B2 (en) * | 2018-03-23 | 2025-01-30 | Koranex Capital | Precision glycoconjugates as therapeutic tools |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ223009A (en) * | 1986-12-31 | 1990-06-26 | Nl Rivm Of Thoven | Oligosaccharides containing d-ribose d-ribitol and phosphate units mimicing haemophilus influenzae type b antigens |
| EP0320942A3 (en) * | 1987-12-18 | 1989-10-04 | American Cyanamid Company | Novel polysaccharides novel macromolecular conjugates of the polysaccharides |
| US5843463A (en) * | 1990-12-21 | 1998-12-01 | Antexbiologics, Inc. | Adhesin-oligosaccharide conjugate vaccine for Haemophilus influenzae |
-
1999
- 1999-08-30 CU CU1999121A patent/CU22904A1/es unknown
-
2000
- 2000-08-15 NZ NZ517464A patent/NZ517464A/en not_active IP Right Cessation
- 2000-08-15 CN CNB008134731A patent/CN1205217C/zh not_active Expired - Lifetime
- 2000-08-15 EP EP00956040A patent/EP1212334B1/en not_active Expired - Lifetime
- 2000-08-15 DE DE60023722T patent/DE60023722T2/de not_active Expired - Lifetime
- 2000-08-15 BR BRPI0013686A patent/BRPI0013686B8/pt not_active IP Right Cessation
- 2000-08-15 AU AU68173/00A patent/AU780816B2/en not_active Ceased
- 2000-08-15 CA CA2382602A patent/CA2382602C/en not_active Expired - Fee Related
- 2000-08-15 AT AT00956040T patent/ATE308551T1/de active
- 2000-08-15 SI SI200030780T patent/SI1212334T1/sl unknown
- 2000-08-15 JP JP2001519710A patent/JP4850377B2/ja not_active Expired - Fee Related
- 2000-08-15 UA UA2002021613A patent/UA75579C2/uk unknown
- 2000-08-15 US US10/070,101 patent/US6765091B1/en not_active Expired - Lifetime
- 2000-08-15 KR KR1020027002706A patent/KR100818163B1/ko not_active Expired - Fee Related
- 2000-08-15 ES ES00956040T patent/ES2252045T3/es not_active Expired - Lifetime
- 2000-08-15 MX MXPA02002066A patent/MXPA02002066A/es active IP Right Grant
- 2000-08-15 EA EA200200314A patent/EA005381B1/ru not_active IP Right Cessation
- 2000-08-15 WO PCT/CU2000/000003 patent/WO2001016146A1/es not_active Ceased
- 2000-08-15 CZ CZ2002721A patent/CZ2002721A3/cs unknown
- 2000-08-15 DK DK00956040T patent/DK1212334T3/da active
- 2000-08-28 CO CO00064095A patent/CO5180646A1/es active IP Right Grant
- 2000-08-29 AR ARP000104496A patent/AR025435A1/es not_active Application Discontinuation
-
2002
- 2002-02-27 ZA ZA200201667A patent/ZA200201667B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1205217C (zh) | 2005-06-08 |
| SI1212334T1 (sl) | 2006-04-30 |
| US6765091B1 (en) | 2004-07-20 |
| DK1212334T3 (da) | 2006-03-20 |
| EP1212334A1 (fr) | 2002-06-12 |
| BRPI0013686B1 (pt) | 2016-07-26 |
| DE60023722T2 (de) | 2006-07-20 |
| CN1376158A (zh) | 2002-10-23 |
| NZ517464A (en) | 2004-03-26 |
| KR20020068501A (ko) | 2002-08-27 |
| UA75579C2 (en) | 2006-05-15 |
| CA2382602A1 (en) | 2001-03-08 |
| AR025435A1 (es) | 2002-11-27 |
| AU6817300A (en) | 2001-03-26 |
| BRPI0013686B8 (pt) | 2021-05-25 |
| MXPA02002066A (es) | 2004-07-30 |
| JP4850377B2 (ja) | 2012-01-11 |
| ZA200201667B (en) | 2003-08-27 |
| JP2003528032A (ja) | 2003-09-24 |
| EA200200314A1 (ru) | 2002-10-31 |
| KR100818163B1 (ko) | 2008-03-31 |
| BR0013686A (pt) | 2002-08-13 |
| ES2252045T3 (es) | 2006-05-16 |
| WO2001016146A1 (es) | 2001-03-08 |
| CO5180646A1 (es) | 2002-07-30 |
| AU780816B2 (en) | 2005-04-21 |
| EP1212334B1 (en) | 2005-11-02 |
| CA2382602C (en) | 2010-02-16 |
| HK1050693A1 (en) | 2003-07-04 |
| ATE308551T1 (de) | 2005-11-15 |
| EA005381B1 (ru) | 2005-02-24 |
| DE60023722D1 (de) | 2005-12-08 |
| CZ2002721A3 (cs) | 2002-07-17 |
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