FR2533827A1 - Composition possedant des proprietes immunoregulatrices, notamment d'adjuvants immunologiques non specifiques, a base de muramylpeptide et d'un derive d'aluminium - Google Patents
Composition possedant des proprietes immunoregulatrices, notamment d'adjuvants immunologiques non specifiques, a base de muramylpeptide et d'un derive d'aluminium Download PDFInfo
- Publication number
- FR2533827A1 FR2533827A1 FR8216485A FR8216485A FR2533827A1 FR 2533827 A1 FR2533827 A1 FR 2533827A1 FR 8216485 A FR8216485 A FR 8216485A FR 8216485 A FR8216485 A FR 8216485A FR 2533827 A1 FR2533827 A1 FR 2533827A1
- Authority
- FR
- France
- Prior art keywords
- sep
- muramyl
- composition according
- peptide
- group
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract description 12
- 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 title abstract description 10
- 150000001398 aluminium Chemical class 0.000 title abstract 2
- 239000000568 immunological adjuvant Substances 0.000 title description 3
- 230000004957 immunoregulator effect Effects 0.000 title description 3
- 239000002671 adjuvant Substances 0.000 claims abstract description 29
- -1 alpha -n-butyl Chemical group 0.000 claims abstract description 24
- 230000002163 immunogen Effects 0.000 claims abstract description 11
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 239000000427 antigen Substances 0.000 claims description 35
- 102000036639 antigens Human genes 0.000 claims description 35
- 108091007433 antigens Proteins 0.000 claims description 35
- 229960005486 vaccine Drugs 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003338 L-glutaminyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229940024606 amino acid Drugs 0.000 claims description 3
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- GDFAOVXKHJXLEI-UHFFFAOYSA-N L-N-Boc-N-methylalanine Natural products CNC(C)C(O)=O GDFAOVXKHJXLEI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims description 2
- 125000000415 L-cysteinyl group Chemical group O=C([*])[C@@](N([H])[H])([H])C([H])([H])S[H] 0.000 claims description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 2
- 229930182816 L-glutamine Natural products 0.000 claims description 2
- 125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 claims description 2
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001176 L-lysyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims description 2
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000000769 L-threonyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@](O[H])(C([H])([H])[H])[H] 0.000 claims description 2
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 claims description 2
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- 125000002252 acyl group Chemical group 0.000 claims description 2
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- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- ZDXPYRJPNDTMRX-GSVOUGTGSA-N D-glutamine Chemical compound OC(=O)[C@H](N)CCC(N)=O ZDXPYRJPNDTMRX-GSVOUGTGSA-N 0.000 claims 1
- 229930195715 D-glutamine Natural products 0.000 claims 1
- 125000002061 L-isoleucyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@](C([H])([H])[H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000003798 L-tyrosyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- NOXFMRMRRUXMEJ-NQYRFPRJSA-N (2R)-2-[[(2S)-2-[acetyl-[(3R,4R,5S,6R)-3-amino-4-[(1R)-1-carboxyethoxy]-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid Chemical compound C(C)(=O)N([C@@H](C)C(=O)N[C@H](CCC(N)=O)C(=O)O)C1[C@H](N)[C@@H](O[C@@H](C(=O)O)C)[C@H](O)[C@H](O1)CO NOXFMRMRRUXMEJ-NQYRFPRJSA-N 0.000 abstract description 2
- 230000002480 immunoprotective effect Effects 0.000 abstract description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 abstract 1
- 230000003014 reinforcing effect Effects 0.000 abstract 1
- 230000004044 response Effects 0.000 description 22
- 241000699670 Mus sp. Species 0.000 description 11
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 230000035931 haemagglutination Effects 0.000 description 8
- 230000009471 action Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 108060003951 Immunoglobulin Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
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- 210000005260 human cell Anatomy 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
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- 238000002255 vaccination Methods 0.000 description 2
- HJCMDXDYPOUFDY-CRCLSJGQSA-N (2r)-5-amino-2-[[(2s)-2-azaniumylpropanoyl]amino]-5-oxopentanoate Chemical compound C[C@H]([NH3+])C(=O)N[C@@H](C([O-])=O)CCC(N)=O HJCMDXDYPOUFDY-CRCLSJGQSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 208000001718 Immediate Hypersensitivity Diseases 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 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 1
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010045240 Type I hypersensitivity Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 230000004523 agglutinating effect Effects 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical class O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010216 atopic IgE responsiveness Diseases 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000863 peptide conjugate Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
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- 238000012353 t test Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- 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
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55505—Inorganic adjuvants
-
- 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
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/5555—Muramyl dipeptides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8216485A FR2533827A1 (fr) | 1982-09-30 | 1982-09-30 | Composition possedant des proprietes immunoregulatrices, notamment d'adjuvants immunologiques non specifiques, a base de muramylpeptide et d'un derive d'aluminium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8216485A FR2533827A1 (fr) | 1982-09-30 | 1982-09-30 | Composition possedant des proprietes immunoregulatrices, notamment d'adjuvants immunologiques non specifiques, a base de muramylpeptide et d'un derive d'aluminium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2533827A1 true FR2533827A1 (fr) | 1984-04-06 |
| FR2533827B1 FR2533827B1 (enrdf_load_stackoverflow) | 1985-04-05 |
Family
ID=9277889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8216485A Granted FR2533827A1 (fr) | 1982-09-30 | 1982-09-30 | Composition possedant des proprietes immunoregulatrices, notamment d'adjuvants immunologiques non specifiques, a base de muramylpeptide et d'un derive d'aluminium |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2533827A1 (enrdf_load_stackoverflow) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0268271A3 (en) * | 1986-11-19 | 1990-04-25 | Sour Pliva Farmaceutska, Kemijska Prehrambena I Kozmeticka Industrija, N.Sol.O. | Metal complexes of n-acetyl-glucosaminyl-n-acetal-muramoyl-l-alanyl-d-isoglutaminyl-(l)-meso-diamino-pimelyl-(d-amide)-(l)-d-alanyl-d-alanine and their use in the manufacture of pharmaceuticals |
| US5112606A (en) * | 1986-01-10 | 1992-05-12 | Sadao Shiosaka | Method of producing antibodies using colloidal metal as carrier |
| FR2672495A1 (fr) * | 1991-02-08 | 1992-08-14 | Vacsyn France Sa | Compositions immunomodulatrices, a base de produits comportant au moins un groupe phosphate ou sulfate, et un gel d'un compose d'aluminium. |
| FR2692149A1 (fr) * | 1992-06-12 | 1993-12-17 | Vacsyn France Sa | Composition adjuvante de l'immunité humorale et à médiation cellulaire n'induisant pas de réponse vis-à-vis de déterminants auto-antigéniques. |
| WO1996019237A1 (fr) * | 1994-12-21 | 1996-06-27 | Vacsyn S.A. | Vaccin presentant une immunogenicite accrue |
| FR2730936A1 (fr) * | 1994-12-21 | 1996-08-30 | Vacsyn Sa | Vaccin presentant une immunogenicite accrue |
| WO1999015185A1 (en) * | 1997-09-22 | 1999-04-01 | Lisovenko, Vasily Trofimovich | Agent for modifying the proliferation, functional activity and death of natural and tumoral cells |
| US6274552B1 (en) | 1993-03-18 | 2001-08-14 | Cytimmune Sciences, Inc. | Composition and method for delivery of biologically-active factors |
| US6528051B2 (en) | 1997-11-10 | 2003-03-04 | Cytimmune Sciences, Inc. | Methods and compositions for enhancing immune response |
| EP1038532A4 (en) * | 1997-04-11 | 2003-08-13 | Oleg Vitallievich Kaljuzhin | IMMUNO MODULATOR AND PHARMACEUTICAL COMPOSITIONS WITH ANTITUM PROPERTIES, AND A FOOD ADDITIVE |
| US6649746B1 (en) | 1999-05-07 | 2003-11-18 | University Of Virginia Patent Foundation | Biological production of stable glutamine, poly-glutamine derivatives in transgenic organisms and their use for therapeutic purposes |
| US7229841B2 (en) | 2001-04-30 | 2007-06-12 | Cytimmune Sciences, Inc. | Colloidal metal compositions and methods |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010055581A1 (en) | 1994-03-18 | 2001-12-27 | Lawrence Tamarkin | Composition and method for delivery of biologically-active factors |
| JP2008504216A (ja) | 2003-12-02 | 2008-02-14 | サイトイミューン サイエンシズ インコーポレイテッド | モノクローナル抗体の生成のための方法および組成物 |
| CA2706700A1 (en) | 2007-11-08 | 2009-05-14 | Cytimmune Sciences, Inc. | Compositions and methods for generating antibodies |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1189340A (en) * | 1967-09-13 | 1970-04-22 | American Cyanamid Co | Antigen-Adjuvant Composition |
| FR2035805A1 (enrdf_load_stackoverflow) * | 1968-08-20 | 1970-12-24 | Miles Lab | |
| FR2288527A2 (fr) * | 1974-10-22 | 1976-05-21 | Anvar | Compositions contenant de la n-acetyl-muramyl- l-alanyl - d-isoglutamine ou de l'acide n-acetyl-muramyl-l-alanyl - d-glutamique, exemptes d'huile et ayant des proprietes adjuvantes |
| FR2343483A1 (fr) * | 1976-03-10 | 1977-10-07 | Anvar | L'ester methylique de la 2- (2-acetamido-2-deoxy-3-o-d-glucopyranosyl) -d-propionyl-l-alanyl-d-isoglutamine et le diester methylique de l'acide 2- (2-acetamido-2-deoxy-3-o-d-glucopyranosyl) -d-propionyl-l-alanyl-d-glutamique et medicaments les contenant |
| FR2369292A1 (fr) * | 1976-11-02 | 1978-05-26 | Anvar | Agents adjuvants immunit |
| EP0013651A1 (fr) * | 1979-01-12 | 1980-07-23 | ANVAR Agence Nationale de Valorisation de la Recherche | Muramyl-peptides fixés sur polymères peptidiques et médicaments les contenant |
-
1982
- 1982-09-30 FR FR8216485A patent/FR2533827A1/fr active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1189340A (en) * | 1967-09-13 | 1970-04-22 | American Cyanamid Co | Antigen-Adjuvant Composition |
| FR2035805A1 (enrdf_load_stackoverflow) * | 1968-08-20 | 1970-12-24 | Miles Lab | |
| FR2288527A2 (fr) * | 1974-10-22 | 1976-05-21 | Anvar | Compositions contenant de la n-acetyl-muramyl- l-alanyl - d-isoglutamine ou de l'acide n-acetyl-muramyl-l-alanyl - d-glutamique, exemptes d'huile et ayant des proprietes adjuvantes |
| FR2343483A1 (fr) * | 1976-03-10 | 1977-10-07 | Anvar | L'ester methylique de la 2- (2-acetamido-2-deoxy-3-o-d-glucopyranosyl) -d-propionyl-l-alanyl-d-isoglutamine et le diester methylique de l'acide 2- (2-acetamido-2-deoxy-3-o-d-glucopyranosyl) -d-propionyl-l-alanyl-d-glutamique et medicaments les contenant |
| FR2369292A1 (fr) * | 1976-11-02 | 1978-05-26 | Anvar | Agents adjuvants immunit |
| EP0013651A1 (fr) * | 1979-01-12 | 1980-07-23 | ANVAR Agence Nationale de Valorisation de la Recherche | Muramyl-peptides fixés sur polymères peptidiques et médicaments les contenant |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112606A (en) * | 1986-01-10 | 1992-05-12 | Sadao Shiosaka | Method of producing antibodies using colloidal metal as carrier |
| EP0268271A3 (en) * | 1986-11-19 | 1990-04-25 | Sour Pliva Farmaceutska, Kemijska Prehrambena I Kozmeticka Industrija, N.Sol.O. | Metal complexes of n-acetyl-glucosaminyl-n-acetal-muramoyl-l-alanyl-d-isoglutaminyl-(l)-meso-diamino-pimelyl-(d-amide)-(l)-d-alanyl-d-alanine and their use in the manufacture of pharmaceuticals |
| FR2672495A1 (fr) * | 1991-02-08 | 1992-08-14 | Vacsyn France Sa | Compositions immunomodulatrices, a base de produits comportant au moins un groupe phosphate ou sulfate, et un gel d'un compose d'aluminium. |
| FR2692149A1 (fr) * | 1992-06-12 | 1993-12-17 | Vacsyn France Sa | Composition adjuvante de l'immunité humorale et à médiation cellulaire n'induisant pas de réponse vis-à-vis de déterminants auto-antigéniques. |
| WO1993025236A1 (fr) * | 1992-06-12 | 1993-12-23 | Vacsyn S.A. | Composition adjuvante de l'immunite humorale et a mediation cellulaire n'induisant pas de reponse vis-a-vis de determinants auto-antigeniques |
| US6274552B1 (en) | 1993-03-18 | 2001-08-14 | Cytimmune Sciences, Inc. | Composition and method for delivery of biologically-active factors |
| WO1996019237A1 (fr) * | 1994-12-21 | 1996-06-27 | Vacsyn S.A. | Vaccin presentant une immunogenicite accrue |
| FR2730935A1 (fr) * | 1994-12-21 | 1996-08-30 | Vacsyn Sa | Vaccin presentant une immunogenicite accrue |
| FR2730936A1 (fr) * | 1994-12-21 | 1996-08-30 | Vacsyn Sa | Vaccin presentant une immunogenicite accrue |
| US6063380A (en) * | 1994-12-21 | 2000-05-16 | Vacsyn S.A. | Enhanced immunogenic vaccine |
| EP1038532A4 (en) * | 1997-04-11 | 2003-08-13 | Oleg Vitallievich Kaljuzhin | IMMUNO MODULATOR AND PHARMACEUTICAL COMPOSITIONS WITH ANTITUM PROPERTIES, AND A FOOD ADDITIVE |
| WO1999015185A1 (en) * | 1997-09-22 | 1999-04-01 | Lisovenko, Vasily Trofimovich | Agent for modifying the proliferation, functional activity and death of natural and tumoral cells |
| US6528051B2 (en) | 1997-11-10 | 2003-03-04 | Cytimmune Sciences, Inc. | Methods and compositions for enhancing immune response |
| US7387900B2 (en) | 1997-11-10 | 2008-06-17 | Cytimmune Sciences, Inc. | Colloidal metal compositions and methods |
| US6649746B1 (en) | 1999-05-07 | 2003-11-18 | University Of Virginia Patent Foundation | Biological production of stable glutamine, poly-glutamine derivatives in transgenic organisms and their use for therapeutic purposes |
| US7229841B2 (en) | 2001-04-30 | 2007-06-12 | Cytimmune Sciences, Inc. | Colloidal metal compositions and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2533827B1 (enrdf_load_stackoverflow) | 1985-04-05 |
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