JPS6412279B2 - - Google Patents
Info
- Publication number
- JPS6412279B2 JPS6412279B2 JP55020348A JP2034880A JPS6412279B2 JP S6412279 B2 JPS6412279 B2 JP S6412279B2 JP 55020348 A JP55020348 A JP 55020348A JP 2034880 A JP2034880 A JP 2034880A JP S6412279 B2 JPS6412279 B2 JP S6412279B2
- Authority
- JP
- Japan
- Prior art keywords
- muramyl
- acetyl
- methyl
- peptide
- alanyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000002671 adjuvant Substances 0.000 claims description 13
- 239000000427 antigen Substances 0.000 claims description 11
- 102000036639 antigens Human genes 0.000 claims description 10
- 108091007433 antigens Proteins 0.000 claims description 10
- 230000001571 immunoadjuvant effect Effects 0.000 claims description 10
- 239000000568 immunological adjuvant Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- NKUHWWPUOXOIIR-CRCLSJGQSA-N (4r)-5-amino-4-[[(2s)-2-azaniumylpropanoyl]amino]-5-oxopentanoate Chemical compound C[C@H](N)C(=O)N[C@@H](C(N)=O)CCC(O)=O NKUHWWPUOXOIIR-CRCLSJGQSA-N 0.000 claims 2
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 230000001861 immunosuppressant effect Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 claims 1
- 239000000644 isotonic solution Substances 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- 210000004877 mucosa Anatomy 0.000 claims 1
- 239000002504 physiological saline solution Substances 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 35
- 238000000034 method Methods 0.000 description 27
- 108090000765 processed proteins & peptides Proteins 0.000 description 17
- 230000000694 effects Effects 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000012634 fragment Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000009471 action Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 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 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000010647 peptide synthesis reaction Methods 0.000 description 6
- -1 halogen acids Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000028993 immune response Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical class NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 230000002163 immunogen Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000001698 pyrogenic effect Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- MNLRQHMNZILYPY-MDMHTWEWSA-N N-acetyl-alpha-D-muramic acid Chemical compound OC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O MNLRQHMNZILYPY-MDMHTWEWSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 150000001720 carbohydrates Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 229960005486 vaccine Drugs 0.000 description 3
- MSFSPUZXLOGKHJ-PGYHGBPZSA-N 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose Chemical compound OC(=O)[C@@H](C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O MSFSPUZXLOGKHJ-PGYHGBPZSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 108010013639 Peptidoglycan Proteins 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000000240 adjuvant effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 108010015899 Glycopeptides Proteins 0.000 description 1
- 102000002068 Glycopeptides Human genes 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- GDFAOVXKHJXLEI-UHFFFAOYSA-N L-N-Boc-N-methylalanine Natural products CNC(C)C(O)=O GDFAOVXKHJXLEI-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 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 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical group NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 230000035931 haemagglutination Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000007124 immune defense Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 229940088592 immunologic factor Drugs 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical group [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000003705 ribosome Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- 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)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7904316A FR2449697A1 (fr) | 1979-02-20 | 1979-02-20 | Nouveaux muramyl-peptides substitues sur un azote peptidique et medicaments les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55113800A JPS55113800A (en) | 1980-09-02 |
| JPS6412279B2 true JPS6412279B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-02-28 |
Family
ID=9222210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2034880A Granted JPS55113800A (en) | 1979-02-20 | 1980-02-20 | Muramyllpeptide type comound and drug containing it |
Country Status (5)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4368190A (en) * | 1980-04-17 | 1983-01-11 | Merck & Co., Inc. | Immunologically active dipeptidyl 4-O-,6-O-acyl-2-amino-2-deoxy-D-glucose derivatives and methods for their preparation |
| JPS57144225A (en) * | 1981-03-04 | 1982-09-06 | Tadao Kokubu | Antigenetic preparation for treating nonspecific allergic diseases and its preparation |
| US4770874A (en) * | 1983-08-22 | 1988-09-13 | Syntex (U.S.A.) Inc. | Polyoxypropylene-polyoxyethylene block polymer based adjuvants |
| US4606918A (en) * | 1983-08-22 | 1986-08-19 | Syntex (U.S.A.) Inc. | Polyoxypropylene-polyoxyethylene block polymer based adjuvants |
| US4772466A (en) * | 1983-08-22 | 1988-09-20 | Syntex (U.S.A.) Inc. | Vaccines comprising polyoxypropylene-polyoxyethylene block polymer based adjuvants |
| US4933179A (en) * | 1983-08-22 | 1990-06-12 | Syntex (U.S.A.) Inc. | Feline leukemia virus antigen vaccines |
| US4765980A (en) * | 1986-04-28 | 1988-08-23 | International Minerals & Chemical Corp. | Stabilized porcine growth hormone |
| US5554372A (en) * | 1986-09-22 | 1996-09-10 | Emory University | Methods and vaccines comprising surface-active copolymers |
| 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 |
| DE69230041T2 (de) * | 1991-11-19 | 2000-01-05 | Peptech (Uk) Ltd., London | Muramylverbindungen zur behandlung von septischem schock |
| US5462735A (en) * | 1993-06-10 | 1995-10-31 | The United States Of America As Represented By The Secretary Of Agriculture | Pasteurella haemolytica subunit vaccine containing capsular polysaccharide and muramyl dipeptide |
| EP3387005B1 (en) * | 2015-12-10 | 2022-08-24 | Bharat Biotech International Limited | Novel muramyl peptide derivative compound, synthesis and uses thereof |
| US12134664B2 (en) | 2015-12-10 | 2024-11-05 | Bharat Biotech International Ltd. | Muramyl peptide derivatives |
| CN108883080B (zh) * | 2015-12-15 | 2021-12-21 | 巴拉特生物技术国际有限公司 | 胞壁酰肽衍生物化合物、其合成及其用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2321896A1 (fr) | 1975-08-29 | 1977-03-25 | Anvar | Agents adjuvants immunologiques actifs en solution aqueuse |
| FR2326930A1 (fr) | 1975-10-09 | 1977-05-06 | Anvar | Agents hydrosolubles depresseurs non specifiques des reponses immunitaires |
| CH613709A5 (en) | 1975-12-10 | 1979-10-15 | Ciba Geigy Ag | Process for the preparation of glucosamine derivatives |
| US4082735A (en) | 1976-04-26 | 1978-04-04 | Syntex (U.S.A.) Inc. | Novel immunological adjuvant compounds and methods of preparation thereof |
| GB1571133A (en) * | 1976-04-26 | 1980-07-09 | Syntex Inc | Immuniological adjuvant peptidoglycans compounds and methods of preparation thereof |
| US4082736A (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 |
| EP0003833B2 (de) * | 1978-02-24 | 1990-12-19 | Ciba-Geigy Ag | Antigenderivate, Verfahren zu deren Herstellung, diese enthaltende pharmazeutische Präparate |
-
1979
- 1979-02-20 FR FR7904316A patent/FR2449697A1/fr active Granted
-
1980
- 1980-02-20 JP JP2034880A patent/JPS55113800A/ja active Granted
- 1980-02-20 EP EP80400242A patent/EP0015810B1/fr not_active Expired
- 1980-02-20 DE DE8080400242T patent/DE3066729D1/de not_active Expired
-
1982
- 1982-01-06 US US06/337,503 patent/US4427659A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3066729D1 (en) | 1984-04-05 |
| EP0015810B1 (fr) | 1984-02-29 |
| EP0015810A1 (fr) | 1980-09-17 |
| US4427659A (en) | 1984-01-24 |
| JPS55113800A (en) | 1980-09-02 |
| FR2449697B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-07-09 |
| FR2449697A1 (fr) | 1980-09-19 |
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