ES2659516T3 - Antígenos sulfoglucolipídicos, su procedimiento de preparación y su uso contra la tuberculosis - Google Patents
Antígenos sulfoglucolipídicos, su procedimiento de preparación y su uso contra la tuberculosis Download PDFInfo
- Publication number
- ES2659516T3 ES2659516T3 ES08702217.4T ES08702217T ES2659516T3 ES 2659516 T3 ES2659516 T3 ES 2659516T3 ES 08702217 T ES08702217 T ES 08702217T ES 2659516 T3 ES2659516 T3 ES 2659516T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- formula
- tuberculosis
- integer
- chosen
- 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.)
- Active
Links
- 201000008827 tuberculosis Diseases 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 8
- 239000000427 antigen Substances 0.000 title claims description 6
- 102000036639 antigens Human genes 0.000 title claims description 6
- 108091007433 antigens Proteins 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000001924 fatty-acyl group Chemical group 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 239000002184 metal Substances 0.000 claims abstract description 3
- 238000000338 in vitro Methods 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 5
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229960005486 vaccine Drugs 0.000 claims description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 2
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000012190 activator Substances 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 238000006277 sulfonation reaction Methods 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 1
- 108090000978 Interleukin-4 Proteins 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 239000012472 biological sample Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 210000004443 dendritic cell Anatomy 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000008105 immune reaction Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000000523 sample Substances 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 241000894006 Bacteria Species 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 4
- 0 C*C(OC(C1OC2=O)C(OC(*(*)C3*)OC(CO)C3O)OC(CO)C1OC2=C[C@@](C)C[C@@](C)C[C@@](C)CC(C)(C)CC(C)(C)C)=O Chemical compound C*C(OC(C1OC2=O)C(OC(*(*)C3*)OC(CO)C3O)OC(CO)C1OC2=C[C@@](C)C[C@@](C)C[C@@](C)CC(C)(C)CC(C)(C)C)=O 0.000 description 3
- 229930186217 Glycolipid Natural products 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 125000000647 trehalose group Chemical group 0.000 description 3
- 101000608750 Arachis hypogaea Alpha-methyl-mannoside-specific lectin Proteins 0.000 description 2
- 101000771730 Tropidolaemus wagleri Waglerin-3 Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 125000005313 fatty acid group Chemical group 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002163 immunogen Effects 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000186366 Mycobacterium bovis Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 206010041232 sneezing Diseases 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- -1 substituent fatty acids Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005844 sulfoglycolipids Chemical class 0.000 description 1
- 208000032922 susceptibility to mycobacterium tuberculosis Diseases 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- 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
-
- 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
- A61P31/06—Antibacterial agents for tuberculosis
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/569—Immunoassay; Biospecific binding assay; Materials therefor for microorganisms, e.g. protozoa, bacteria, viruses
- G01N33/56911—Bacteria
- G01N33/5695—Mycobacteria
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/195—Assays involving biological materials from specific organisms or of a specific nature from bacteria
- G01N2333/35—Assays involving biological materials from specific organisms or of a specific nature from bacteria from Mycobacteriaceae (F)
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cell Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Food Science & Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07290097 | 2007-01-24 | ||
| EP07290097A EP1950218A1 (en) | 2007-01-24 | 2007-01-24 | Sulfoglycolipid antigens, their process of preparation, and their use against tuberculosis |
| PCT/IB2008/000053 WO2008090425A1 (en) | 2007-01-24 | 2008-01-11 | Sulfoglycolipid antigens, their process of preparation, and their use against tuberculosis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2659516T3 true ES2659516T3 (es) | 2018-03-16 |
Family
ID=38080940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08702217.4T Active ES2659516T3 (es) | 2007-01-24 | 2008-01-11 | Antígenos sulfoglucolipídicos, su procedimiento de preparación y su uso contra la tuberculosis |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8268801B2 (https=) |
| EP (2) | EP1950218A1 (https=) |
| JP (1) | JP5547491B2 (https=) |
| CN (1) | CN101622266B (https=) |
| BR (1) | BRPI0806400A8 (https=) |
| ES (1) | ES2659516T3 (https=) |
| WO (1) | WO2008090425A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8288509B2 (en) * | 2002-02-22 | 2012-10-16 | National Hospital Organization Kinki-chuo Chest Medical center | Therapeutic agent for infections, and treatment method using the same |
| JP6195848B2 (ja) | 2012-01-27 | 2017-09-13 | ザ、リージェンツ、オブ、ザ、ユニバーシティ、オブ、カリフォルニアＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｃａｌｉｆｏｒｎｉａ | 糖ポリマーを用いた生体分子の安定化 |
| JP5945756B1 (ja) * | 2015-06-01 | 2016-07-05 | マイクロ波化学株式会社 | ショ糖脂肪酸エステルの製造方法 |
| JP6276806B2 (ja) * | 2016-05-30 | 2018-02-07 | マイクロ波化学株式会社 | ショ糖脂肪酸エステルの製造方法 |
| CN106488925B (zh) * | 2015-06-01 | 2019-04-23 | 微波化学有限公司 | 蔗糖脂肪酸酯的制造方法 |
| JP5952980B1 (ja) * | 2016-02-17 | 2016-07-13 | マイクロ波化学株式会社 | ショ糖ステアリン酸エステルの製造方法 |
| NL2017204B1 (en) * | 2016-06-08 | 2017-12-18 | Kei International Ltd | Solid substrate comprising antigens immobilised thereto, biosensor comprising said solid substrate and method for detecting the presence of mycobacterial material in a sample |
| NL2016913B1 (en) * | 2016-06-08 | 2017-12-18 | Kei International Ltd | Solid substrate comprising antigens immobilised thereto and use thereof in a method for detecting the presence of mycobacterial material in a sample |
| WO2017211314A1 (en) | 2016-06-08 | 2017-12-14 | Kei International Limited | Method for detecting presence of mycobacterial material in sample using immobilised mannosyl phosphoketide antigen |
| NL2021443B1 (en) | 2018-08-08 | 2020-02-20 | Kei International Ltd | Synthetic antigens for tuberculosis detection |
| NL2022166B1 (en) | 2018-12-10 | 2020-07-02 | Kei International Ltd | Nitrocellulose sheet comprising immobilized immunoglobulins and lipid based antigens and use thereof |
| FR3092112B1 (fr) | 2019-01-29 | 2023-01-06 | Arkema France | Huile de base lubrifiante synthetisee a partir d’esters de polyols et d’acides gras biosources |
| FR3092113B1 (fr) * | 2019-01-29 | 2023-04-21 | Arkema France | Huile de base lubrifiante synthetisee a partir desters d’alcool de sucre |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1469007A1 (en) * | 2003-04-18 | 2004-10-20 | Centre National De La Recherche Scientifique (Cnrs) | Sulfoglycolipid antigens, their extraction from mycobacterieum tuberculosis, and their use against tuberculosis |
-
2007
- 2007-01-24 EP EP07290097A patent/EP1950218A1/en not_active Withdrawn
-
2008
- 2008-01-11 BR BRPI0806400A patent/BRPI0806400A8/pt not_active Application Discontinuation
- 2008-01-11 EP EP08702217.4A patent/EP2125849B1/en not_active Not-in-force
- 2008-01-11 US US12/524,091 patent/US8268801B2/en not_active Expired - Fee Related
- 2008-01-11 ES ES08702217.4T patent/ES2659516T3/es active Active
- 2008-01-11 WO PCT/IB2008/000053 patent/WO2008090425A1/en not_active Ceased
- 2008-01-11 JP JP2009546828A patent/JP5547491B2/ja not_active Expired - Fee Related
- 2008-01-11 CN CN2008800060908A patent/CN101622266B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101622266B (zh) | 2013-09-11 |
| JP2010516748A (ja) | 2010-05-20 |
| BRPI0806400A8 (pt) | 2018-10-23 |
| EP2125849B1 (en) | 2017-11-15 |
| US8268801B2 (en) | 2012-09-18 |
| CN101622266A (zh) | 2010-01-06 |
| WO2008090425A1 (en) | 2008-07-31 |
| US20100166801A1 (en) | 2010-07-01 |
| EP1950218A1 (en) | 2008-07-30 |
| JP5547491B2 (ja) | 2014-07-16 |
| BRPI0806400A2 (pt) | 2011-09-06 |
| EP2125849A1 (en) | 2009-12-02 |
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