GB1572368A - Pharmaceutical compositions containing glycolipids - Google Patents
Pharmaceutical compositions containing glycolipids Download PDFInfo
- Publication number
- GB1572368A GB1572368A GB2661577A GB2661577A GB1572368A GB 1572368 A GB1572368 A GB 1572368A GB 2661577 A GB2661577 A GB 2661577A GB 2661577 A GB2661577 A GB 2661577A GB 1572368 A GB1572368 A GB 1572368A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- glycolipid
- active ingredient
- acid residue
- acid
- 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
Links
- 229930186217 Glycolipid Natural products 0.000 title claims description 68
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 claims description 69
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 46
- CUEQHYJSSUSIFI-UHFFFAOYSA-N corynomycolic acid Chemical compound CCCCCCCCCCCCCCCC(O)C(C(O)=O)CCCCCCCCCCCCCC CUEQHYJSSUSIFI-UHFFFAOYSA-N 0.000 claims description 34
- 239000004480 active ingredient Substances 0.000 claims description 30
- 108091007433 antigens Proteins 0.000 claims description 29
- 102000036639 antigens Human genes 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 20
- 229930006000 Sucrose Natural products 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000005720 sucrose Substances 0.000 claims description 20
- 239000004382 Amylase Substances 0.000 claims description 18
- 229930091371 Fructose Natural products 0.000 claims description 17
- 239000005715 Fructose Substances 0.000 claims description 17
- 244000005700 microbiome Species 0.000 claims description 17
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 241001465754 Metazoa Species 0.000 claims description 15
- 239000000427 antigen Substances 0.000 claims description 15
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 14
- 239000008103 glucose Substances 0.000 claims description 14
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 241000699670 Mus sp. Species 0.000 claims description 9
- 210000004027 cell Anatomy 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 claims description 7
- 108010088751 Albumins Proteins 0.000 claims description 7
- 102000009027 Albumins Human genes 0.000 claims description 7
- 241000186216 Corynebacterium Species 0.000 claims description 7
- 102000002322 Egg Proteins Human genes 0.000 claims description 7
- 108010000912 Egg Proteins Proteins 0.000 claims description 7
- 239000003708 ampul Substances 0.000 claims description 7
- 235000014103 egg white Nutrition 0.000 claims description 7
- 210000000969 egg white Anatomy 0.000 claims description 7
- 238000000855 fermentation Methods 0.000 claims description 7
- 230000004151 fermentation Effects 0.000 claims description 7
- 241000186063 Arthrobacter Species 0.000 claims description 6
- 241000186359 Mycobacterium Species 0.000 claims description 6
- 241000187561 Rhodococcus erythropolis Species 0.000 claims description 6
- 241000186367 Mycobacterium avium Species 0.000 claims description 5
- 241000187654 Nocardia Species 0.000 claims description 5
- 230000009089 cytolysis Effects 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 201000006512 mast cell neoplasm Diseases 0.000 claims description 4
- 208000006971 mastocytoma Diseases 0.000 claims description 4
- 239000006187 pill Substances 0.000 claims description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 4
- 229920000053 polysorbate 80 Polymers 0.000 claims description 4
- 230000002285 radioactive effect Effects 0.000 claims description 4
- 210000004989 spleen cell Anatomy 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
- 241000520094 Mycobacterium paraffinicum Species 0.000 claims description 3
- 241000187563 Rhodococcus ruber Species 0.000 claims description 3
- 239000006196 drop Substances 0.000 claims description 3
- 239000007928 intraperitoneal injection Substances 0.000 claims description 3
- 241001522132 Corynebacterium pseudodiphtheriticum Species 0.000 claims description 2
- 241000203720 Pimelobacter simplex Species 0.000 claims description 2
- 231100000403 acute toxicity Toxicity 0.000 claims description 2
- 230000007059 acute toxicity Effects 0.000 claims description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 125000005313 fatty acid group Chemical group 0.000 claims 4
- 241000187480 Mycobacterium smegmatis Species 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 241000700198 Cavia Species 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 206010040914 Skin reaction Diseases 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 230000002708 enhancing effect Effects 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000035483 skin reaction Effects 0.000 description 4
- 231100000430 skin reaction Toxicity 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 230000036039 immunity Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 108010047620 Phytohemagglutinins Proteins 0.000 description 2
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 2
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- -1 fatty acid ester Chemical class 0.000 description 2
- 210000000548 hind-foot Anatomy 0.000 description 2
- 238000009169 immunotherapy Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000001885 phytohemagglutinin Effects 0.000 description 2
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 241000187653 Nocardia globerula Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- XETCRXVKJHBPMK-MJSODCSWSA-N trehalose 6,6'-dimycolate Chemical compound C([C@@H]1[C@H]([C@H](O)[C@@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](COC(=O)C(CCCCCCCCCCC3C(C3)CCCCCCCCCCCCCCCCCC)C(O)CCCCCCCCCCCCCCCCCCCCCCCCC)O2)O)O1)O)OC(=O)C(C(O)CCCCCCCCCCCCCCCCCCCCCCCCC)CCCCCCCCCCC1CC1CCCCCCCCCCCCCCCCCC XETCRXVKJHBPMK-MJSODCSWSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7586676A JPS533514A (en) | 1976-06-25 | 1976-06-25 | Adjuvant containing sugarlipid as effective component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1572368A true GB1572368A (en) | 1980-07-30 |
Family
ID=13588592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2661577A Expired GB1572368A (en) | 1976-06-25 | 1977-06-24 | Pharmaceutical compositions containing glycolipids |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS533514A (cg-RX-API-DMAC7.html) |
| FR (1) | FR2355506A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1572368A (cg-RX-API-DMAC7.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399683A (en) * | 1993-03-26 | 1995-03-21 | Inflazyme Pharmaceuticals, Inc. | Mirror amide cord factors and mirror thioester cord factors for diagnosis of tuberculosis |
| WO2004012751A1 (ja) * | 2002-08-02 | 2004-02-12 | Sumitomo Pharmaceuticals Company, Limited | 細菌細胞壁骨格成分製剤 |
| US8052981B2 (en) | 1999-11-30 | 2011-11-08 | Protherics Medicines Development Limited | Mono- and disaccharide derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5428830A (en) * | 1977-08-09 | 1979-03-03 | Ichirou Azuma | Immunological treating agent of tumor containing glycolipid as effective component |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1426042A (en) * | 1971-11-26 | 1976-02-25 | Anvar | water-soluble immunological adjuvants |
| JPS5048186A (cg-RX-API-DMAC7.html) * | 1973-08-29 | 1975-04-30 | ||
| JPS5129291A (en) * | 1974-09-02 | 1976-03-12 | Kyowa Hakko Kogyo Kk | Hatsukohonyorukato oyobi shotonoshibosanesuteru no seizoho |
| JPS5129292A (ja) * | 1974-09-02 | 1976-03-12 | Kyowa Hakko Kogyo Kk | Hatsukohonyorugurukoosu oyobi toreharoosu no shibosanesuteru no seizoho |
| FR2319373A1 (fr) * | 1975-07-29 | 1977-02-25 | Anvar | Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi obtenus |
-
1976
- 1976-06-25 JP JP7586676A patent/JPS533514A/ja active Pending
-
1977
- 1977-06-24 FR FR7719379A patent/FR2355506A1/fr active Granted
- 1977-06-24 GB GB2661577A patent/GB1572368A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399683A (en) * | 1993-03-26 | 1995-03-21 | Inflazyme Pharmaceuticals, Inc. | Mirror amide cord factors and mirror thioester cord factors for diagnosis of tuberculosis |
| US8052981B2 (en) | 1999-11-30 | 2011-11-08 | Protherics Medicines Development Limited | Mono- and disaccharide derivatives |
| US8637659B2 (en) | 1999-11-30 | 2014-01-28 | Protherics Medicines Development Limited | Mono-and disaccharide derivatives |
| WO2004012751A1 (ja) * | 2002-08-02 | 2004-02-12 | Sumitomo Pharmaceuticals Company, Limited | 細菌細胞壁骨格成分製剤 |
| JPWO2004012751A1 (ja) * | 2002-08-02 | 2006-09-21 | 大日本住友製薬株式会社 | 細菌細胞壁骨格成分製剤 |
| JP4726485B2 (ja) * | 2002-08-02 | 2011-07-20 | 大日本住友製薬株式会社 | 細菌細胞壁骨格成分製剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2355506A1 (fr) | 1978-01-20 |
| FR2355506B1 (cg-RX-API-DMAC7.html) | 1981-06-19 |
| JPS533514A (en) | 1978-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930624 |