SU1277905A3 - Способ получени натриевых солей производных мурамилпептидов - Google Patents
Способ получени натриевых солей производных мурамилпептидов Download PDFInfo
- Publication number
- SU1277905A3 SU1277905A3 SU802954161A SU2954161A SU1277905A3 SU 1277905 A3 SU1277905 A3 SU 1277905A3 SU 802954161 A SU802954161 A SU 802954161A SU 2954161 A SU2954161 A SU 2954161A SU 1277905 A3 SU1277905 A3 SU 1277905A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compound
- mmol
- conh
- alanyl
- sodium salt
- Prior art date
Links
- 159000000000 sodium salts Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 4
- 125000001446 muramyl group Chemical group N[C@@H](C=O)[C@@H](O[C@@H](C(=O)*)C)[C@H](O)[C@H](O)CO 0.000 abstract description 3
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 3
- 239000011734 sodium Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 5
- 230000003308 immunostimulating effect Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- 101100517284 Caenorhabditis elegans nsun-1 gene Proteins 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- NJUISRMVIKYYCN-UHFFFAOYSA-N acetic acid;chloroform;methanol;hydrate Chemical compound O.OC.CC(O)=O.ClC(Cl)Cl NJUISRMVIKYYCN-UHFFFAOYSA-N 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 208000035196 congenital hypomyelinating 2 neuropathy Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 201000000459 head and neck squamous cell carcinoma Diseases 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000000108 ultra-filtration Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/005—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
-
- 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
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)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH689379 | 1979-07-25 | ||
| AU66581/81A AU6658181A (en) | 1979-07-25 | 1981-01-23 | Increasing antibiotic action of antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1277905A3 true SU1277905A3 (ru) | 1986-12-15 |
Family
ID=34862371
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802954161A SU1277905A3 (ru) | 1979-07-25 | 1980-07-24 | Способ получени натриевых солей производных мурамилпептидов |
| SU813350700A SU1277906A3 (ru) | 1979-07-25 | 1981-10-29 | Способ получени натриевых солей производных мурамилпептидов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813350700A SU1277906A3 (ru) | 1979-07-25 | 1981-10-29 | Способ получени натриевых солей производных мурамилпептидов |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US4414204A (OSRAM) |
| EP (1) | EP0025495B1 (OSRAM) |
| JP (1) | JPS5649397A (OSRAM) |
| KR (1) | KR840001617B1 (OSRAM) |
| AU (2) | AU541147B2 (OSRAM) |
| CA (1) | CA1183129A (OSRAM) |
| CS (1) | CS276965B6 (OSRAM) |
| CY (1) | CY1381A (OSRAM) |
| DD (1) | DD153843A5 (OSRAM) |
| DE (1) | DE3068304D1 (OSRAM) |
| DK (1) | DK161025C (OSRAM) |
| ES (1) | ES8105971A1 (OSRAM) |
| FI (1) | FI75578C (OSRAM) |
| GR (1) | GR69314B (OSRAM) |
| HK (1) | HK85787A (OSRAM) |
| HU (1) | HU188861B (OSRAM) |
| IE (1) | IE50145B1 (OSRAM) |
| IL (1) | IL60676A (OSRAM) |
| MX (1) | MX9203368A (OSRAM) |
| MY (1) | MY8700554A (OSRAM) |
| NO (1) | NO157177C (OSRAM) |
| NZ (1) | NZ194432A (OSRAM) |
| PL (2) | PL131613B1 (OSRAM) |
| PT (1) | PT71607A (OSRAM) |
| SG (1) | SG38187G (OSRAM) |
| SU (2) | SU1277905A3 (OSRAM) |
| ZA (1) | ZA804487B (OSRAM) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1582884A (en) * | 1977-05-19 | 1981-01-14 | Beecham Group Ltd | Clavulanic acid derivatives their preparation and use |
| ZA804670B (en) * | 1979-08-03 | 1981-07-29 | Beecham Group Ltd | Derivatives of clavulanic acid, a process for their preparation and their use |
| FI803077A7 (fi) * | 1979-10-12 | 1981-04-13 | Ciba Geigy Ag | Foerfarande foer framstaellning av myramylpeptider |
| EP0053893B1 (en) * | 1980-12-09 | 1985-03-20 | Beecham Group Plc | Derivatives of clavulanic acid, their preparation and their use |
| NZ199200A (en) * | 1980-12-23 | 1984-07-31 | Beecham Group Ltd | Clavulanic acid derivatives and pharmaceutical compositions |
| EP0056560A1 (de) * | 1981-01-19 | 1982-07-28 | Ciba-Geigy Ag | Antibiotische Präparate mit gesteigerter Wirksamkeit, Verfahren zu deren Herstellung und Verfahren zur Steigerung der antibiotischen Wirkung von Antibiotika |
| GR78246B (OSRAM) * | 1981-01-23 | 1984-09-26 | Ciba Geigy Ag | |
| US5189017A (en) * | 1982-07-23 | 1993-02-23 | Ciba-Geigy Corporation | Use of sugar derivatives for the prophylaxis and treatment of virus infections |
| US5334583A (en) * | 1982-07-23 | 1994-08-02 | Ciba-Geigy Corp. | Use of sugar derivatives for the prophylaxis and treatment of virus infections |
| EP0102319B1 (de) * | 1982-07-23 | 1987-08-19 | Ciba-Geigy Ag | Verwendung von Muramylpeptiden oder deren Analogen zur Prophylaxe und Therapie von Virusinfektionen |
| DE3367596D1 (en) * | 1982-07-23 | 1987-01-02 | Ciba Geigy Ag | Muramyl peptides and method for their preparation |
| US4746651A (en) * | 1983-11-01 | 1988-05-24 | Scripps Clinic And Research Foundation | Antimicrobial chemotherapeutic potentiation using substituted nucleoside derivatives |
| US5171568A (en) * | 1984-04-06 | 1992-12-15 | Chiron Corporation | Recombinant herpes simplex gb-gd vaccine |
| FR2564096B1 (fr) * | 1984-05-11 | 1988-02-19 | Anvar | Derives lipophiles de muramylpeptides ayant des proprietes d'activation des macrophages, compositions les contenant et procede pour les obtenir |
| ATE45744T1 (de) * | 1984-07-25 | 1989-09-15 | Ciba Geigy Ag | Phosphatidylverbindungen, verfahren zu ihrer herstellung und ihre verwendung. |
| EP0174912A3 (de) * | 1984-09-13 | 1986-06-04 | Ciba-Geigy Ag | Phosphorverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CA1260393A (en) * | 1984-10-16 | 1989-09-26 | Lajos Tarcsay | Liposomes of synthetic lipids |
| GB8524001D0 (en) * | 1985-09-30 | 1985-11-06 | Glaxo Group Ltd | Pharmaceutical composition |
| US4873322A (en) * | 1986-01-24 | 1989-10-10 | Ciba-Geigy Corporation | Saccharide derivatives and processes for their manufacture |
| US4916118A (en) * | 1986-08-18 | 1990-04-10 | Board Of Regents, The University Of Texas System | Pharmaceutical administration systems containing chemotactic peptides |
| US5149529A (en) * | 1988-04-08 | 1992-09-22 | Board Of Trustees Of Leland Chiron Corporation | Compositions and treatment for herpes simplex |
| US4950645A (en) * | 1988-07-08 | 1990-08-21 | Immunotherapeutics, Inc. | Composition for macrophage activation |
| US5416070A (en) * | 1988-07-08 | 1995-05-16 | Immunotherapeutics, Inc. | Composition for macrophage activation |
| US4994440A (en) * | 1989-02-13 | 1991-02-19 | Creaven Patrick J | Method for the treatment of renal cell carcinoma |
| GB9320820D0 (en) * | 1993-10-08 | 1993-12-01 | Biokine Tech Ltd | Compounds for medicinal use |
| US6156319A (en) * | 1994-07-25 | 2000-12-05 | The Trustees Of The University Of Pennsylvania | Soluble herpesvirus glycoprotein complex vaccine |
| US6080427A (en) * | 1997-04-17 | 2000-06-27 | Bristol-Myers Squibb Company | Cefadroxil monohydrate tablet formulation |
| AUPP059897A0 (en) * | 1997-11-27 | 1998-01-08 | Fujisawa Pharmaceutical Co., Ltd. | New use of bicozamycin |
| US20040029842A1 (en) * | 2001-12-18 | 2004-02-12 | Gardner Wallace J. | Triglyceride lowering, common cold and pneumonia prevention composition comprising tetracycline, and methods of treating or preventing diseases using same |
| EP1670508B1 (en) | 2003-02-28 | 2012-10-24 | Trustees Of The University Of Pennsylvania | Compositions, methods and kits relating to poxvirus subunit vaccines |
| US20050079187A1 (en) * | 2003-10-14 | 2005-04-14 | Gardner Wallace J. | Composition, kit and method for reducing plaque formation, tooth decay and incidence of caries |
| EP1781338A4 (en) * | 2004-07-19 | 2010-02-10 | Baylor College Medicine | MODULATION OF CYTOKIN SIGNALING REGULATORS AND APPLICATIONS FOR IMMUNOTHERAPY |
| US7868159B2 (en) * | 2005-06-23 | 2011-01-11 | Baylor College Of Medicine | Modulation of negative immune regulators and applications for immunotherapy |
| US8367052B2 (en) | 2007-03-26 | 2013-02-05 | General Regeneratives Holdings Inc. | Methods for promoting protection and regeneration of bone marrow using CXCL9 and anti-CXCL9 antibodies |
| CN101932339B (zh) * | 2007-11-30 | 2014-10-29 | 贝勒医学院 | 树突细胞疫苗组合物及其应用 |
| CN105126072B (zh) | 2009-03-25 | 2020-05-15 | 德克萨斯大学系统董事会 | 用于刺激哺乳动物对病原体的先天免疫抵抗力的组合物 |
| US9808504B2 (en) | 2009-09-22 | 2017-11-07 | Yale University | Immunogenic epitopes as targets for universal cancer vaccines |
| KR101955365B1 (ko) | 2011-07-12 | 2019-03-07 | 필라델피아 헬스 앤드 에듀케이션 코포레이션 디/비/에이 드렉셀 유니버시티 컬리지 오브 메디슨 | 신규한 클로스트리듐 디피실(Clostridium Difficile) DNA 백신 |
| RU2491922C1 (ru) * | 2012-04-26 | 2013-09-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государственная сельскохозяйственная академия имени профессора И.И. Иванова | Способ повышения биоцидного и лечебного действия крема-суспензии с энрофлоксацином |
| RU2527330C2 (ru) * | 2012-07-05 | 2014-08-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государственная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Способ повышения биоцидного и лечебного действия крема - суспензии с метронидазолом |
| EP2951199A4 (en) | 2013-01-31 | 2016-07-20 | Univ Jefferson | Fusion proteins for the modulation of regulatory and effector T cells |
| WO2015116178A1 (en) | 2014-01-31 | 2015-08-06 | Thomas Jefferson University | Fusion proteins for modulating regulatory and effector t cells |
| WO2016044839A2 (en) | 2014-09-19 | 2016-03-24 | The Board Of Regents Of The University Of Texas System | Compositions and methods for treating viral infections through stimulated innate immunity in combination with antiviral compounds |
| US10610564B2 (en) | 2015-02-26 | 2020-04-07 | Stc.Unm | IRGM and precision autophagy controls for antimicrobial and inflammatory disease states and methods of detection of autophagy |
| EP3389643B1 (en) | 2015-12-15 | 2023-05-03 | Bharat Biotech International Limited | Novel muramyl peptide derivative compound, synthesis and uses thereof |
| ES2913073T3 (es) | 2016-04-29 | 2022-05-31 | Icahn School Med Mount Sinai | Direccionamiento del sistema inmunitario innato para inducir tolerancia a largo plazo y resolver la acumulación de macrófagos en aterosclerosis |
| US20220089670A1 (en) | 2018-12-28 | 2022-03-24 | University Of Rochester | Gene Therapy for BEST1 Dominant Mutations |
| BR112023018950A2 (pt) | 2021-03-19 | 2024-02-27 | Icahn School Med Mount Sinai | Composto, composições nanobiológica e farmacêutica, métodos para tratar um distúrbio de proliferação celular, para tratar sepse e para ativar um receptor nod2, processo para fabricação de uma composição nanobiológica e kit |
| WO2025096754A1 (en) | 2023-10-31 | 2025-05-08 | Musc Foundation For Research Development | The use of enolase inhibitor pomhex for treatment of fibrosis |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7308450A (OSRAM) * | 1972-06-20 | 1973-12-27 | ||
| US4001395A (en) * | 1972-06-20 | 1977-01-04 | Agence Nationale De Valorisation De La Recherche (Anvar) | Hydrosoluble extracts of mycobacteria |
| US4186194A (en) * | 1973-10-23 | 1980-01-29 | Agence Nationale De Valorisation De La Recherche (Anvar) | Water soluble agents effective as immunological adjuvants for stimulating, in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
| CH613709A5 (en) | 1975-12-10 | 1979-10-15 | Ciba Geigy Ag | Process for the preparation of glucosamine derivatives |
| US4082736A (en) * | 1976-04-26 | 1978-04-04 | Syntex (U.S.A.) Inc. | Novel immunological adjuvant compounds and methods of preparation thereof |
| US4082735A (en) * | 1976-04-26 | 1978-04-04 | Syntex (U.S.A.) Inc. | Novel immunological adjuvant compounds and methods of preparation thereof |
| GB1563561A (en) * | 1976-06-23 | 1980-03-26 | Daiichi Seiyaku Co | Muramyldipeptide derivatives and process for the preparation thereof |
| FR2368282A1 (fr) * | 1976-10-22 | 1978-05-19 | Anvar | Adjuvant immunologique constitue par le p-amino-phenyl de n-acetyl-muramyl-l-alanyl-d-isoglutamine |
| US4268505A (en) * | 1978-04-13 | 1981-05-19 | Kureha Kagaku Kogyo Kabushiki Kaisha | Pharmaceutical composition comprising a nitrogen-containing polysaccharide and an antibiotic agent, and a method of treating an infectious disease therewith |
| FI803077A7 (fi) * | 1979-10-12 | 1981-04-13 | Ciba Geigy Ag | Foerfarande foer framstaellning av myramylpeptider |
-
1980
- 1980-07-21 FI FI802294A patent/FI75578C/fi not_active IP Right Cessation
- 1980-07-22 NO NO802200A patent/NO157177C/no unknown
- 1980-07-23 GR GR62524A patent/GR69314B/el unknown
- 1980-07-23 CA CA000356860A patent/CA1183129A/en not_active Expired
- 1980-07-23 ES ES493633A patent/ES8105971A1/es not_active Expired
- 1980-07-24 IE IE1533/80A patent/IE50145B1/en unknown
- 1980-07-24 ZA ZA00804487A patent/ZA804487B/xx unknown
- 1980-07-24 HU HU801854A patent/HU188861B/hu unknown
- 1980-07-24 PT PT71607A patent/PT71607A/pt unknown
- 1980-07-24 DK DK319480A patent/DK161025C/da not_active IP Right Cessation
- 1980-07-24 NZ NZ194432A patent/NZ194432A/xx unknown
- 1980-07-24 IL IL60676A patent/IL60676A/xx unknown
- 1980-07-24 SU SU802954161A patent/SU1277905A3/ru active
- 1980-07-25 KR KR1019800002947A patent/KR840001617B1/ko not_active Expired
- 1980-07-25 EP EP80104395A patent/EP0025495B1/de not_active Expired
- 1980-07-25 PL PL1980225870A patent/PL131613B1/pl unknown
- 1980-07-25 PL PL1980231704A patent/PL127481B1/pl unknown
- 1980-07-25 AU AU60788/80A patent/AU541147B2/en not_active Expired
- 1980-07-25 DE DE8080104395T patent/DE3068304D1/de not_active Expired
- 1980-07-25 CY CY138180A patent/CY1381A/xx unknown
- 1980-07-25 JP JP10233680A patent/JPS5649397A/ja active Granted
- 1980-07-25 DD DD80222879A patent/DD153843A5/de not_active IP Right Cessation
- 1980-07-25 CS CS805262A patent/CS276965B6/cs not_active IP Right Cessation
-
1981
- 1981-01-21 US US06/226,966 patent/US4414204A/en not_active Expired - Fee Related
- 1981-01-23 AU AU66581/81A patent/AU6658181A/en not_active Abandoned
- 1981-07-16 US US06/283,759 patent/US4406890A/en not_active Expired - Lifetime
- 1981-10-29 SU SU813350700A patent/SU1277906A3/ru active
-
1987
- 1987-04-25 SG SG381/87A patent/SG38187G/en unknown
- 1987-11-19 HK HK857/87A patent/HK85787A/xx not_active IP Right Cessation
- 1987-12-30 MY MY554/87A patent/MY8700554A/xx unknown
-
1992
- 1992-06-25 MX MX9203368A patent/MX9203368A/es unknown
Non-Patent Citations (1)
| Title |
|---|
| Патент СССР Р 660589, кл. С 07 С 103/52, 30.04.79. * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1277905A3 (ru) | Способ получени натриевых солей производных мурамилпептидов | |
| SU1181540A3 (ru) | Способ получени сульфамоилзамещенного производного фенэтиламина и его кислотной соли | |
| CH676715A5 (OSRAM) | ||
| KR100190808B1 (ko) | 유도체화된디에틸렌트리아민펜타아세트산착물및이를함유하는조영제조성물 | |
| US4304726A (en) | Process for the preparation of cholesterol derivatives | |
| SU976849A3 (ru) | Способ получени производных изоциануровой кислоты | |
| SU1419520A3 (ru) | Способ получени производных метилендифосфоновой кислоты и ее щелочных солей | |
| AU653202B2 (en) | Oral gallium complexes | |
| RU2036929C1 (ru) | Эфиры эстрамастина или их фармацевтически приемлемые соли и способ их получения | |
| DE3026214A1 (de) | Salicylsaeure-derivate, ihre pharmazeutisch vertraeglichen salze und verfahren zu ihrer herstellung | |
| SU508176A3 (ru) | Способ получени аминопроизводных бензофенона | |
| FR2467856A1 (fr) | (2r-cis)-(3-methyloxyranyl)-phosphonate de mono-(2-ammonium-2-hydroxymethyl-1,3-propane-diol), procede pour sa preparation et compositions pharmaceutiques qui le contiennent | |
| RU2037494C1 (ru) | Производные 2-азабицикло(2,2,1)гепт-5-ен-2-уксусной кислоты | |
| GB2098989A (en) | Lysine salts | |
| US2447361A (en) | dl-nu-cyclohexylacetylserine hexahydrobenzyl amide | |
| SU1028250A3 (ru) | Способ получени @ -глюкофуранозид-6-ил- @ -нитрозомочевин | |
| JPH09104693A (ja) | グリコシド類、グリコシドの無糖分解産物およびその誘導体 | |
| EP0209511B1 (fr) | Chlorhydrates de chlorures de dérivés d'aminoalkyl-2 hydroxy-9 ellipticinium et compositions pharmaceutiques en contenant | |
| US4313926A (en) | Method for the preparation of a scintillographic agent | |
| EP0309971A2 (en) | New spergualin-related compound and pharmaceutical composition | |
| RU2128185C1 (ru) | 3-0-сукциноил-11-оксо-урсоловая кислота и ее диаммонийная соль, проявляющая иммуностимулирующую активность | |
| SU1373323A3 (ru) | Способ получени 2-амино-9-(2-оксиэтоксиметил)-9Н-пурина (его варианты) | |
| GB2102812A (en) | Therapeutically active compounds from species of rubia synthetic derivatives thereof, methods for the production thereof and pharmaceutical compositions comprising the same | |
| EP0411624A2 (en) | Saccharide derivatives of protocatechualdehyde | |
| FI62283C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-2'-karboxifenyl-4-klorantranilsyraderivat |