FR2343483A1 - Immunogical adjuvants for weak vaccine antigens - are (2)-acetamido-deoxy (D)-glucopyranosyl (D)-propionyl (L)-alanyl (D)-glutamic acid esters and (D)-isoglutamines - Google Patents

Immunogical adjuvants for weak vaccine antigens - are (2)-acetamido-deoxy (D)-glucopyranosyl (D)-propionyl (L)-alanyl (D)-glutamic acid esters and (D)-isoglutamines

Info

Publication number
FR2343483A1
FR2343483A1 FR7606820A FR7606820A FR2343483A1 FR 2343483 A1 FR2343483 A1 FR 2343483A1 FR 7606820 A FR7606820 A FR 7606820A FR 7606820 A FR7606820 A FR 7606820A FR 2343483 A1 FR2343483 A1 FR 2343483A1
Authority
FR
France
Prior art keywords
glucopyranosyl
alanyl
acetamido
deoxy
propionyl
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
Application number
FR7606820A
Other languages
French (fr)
Other versions
FR2343483B1 (en
Inventor
Francoise Audibert
Louis Chedid
Pierre Lefrancier
Jean Choay
Egar Lederer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bpifrance Financement SA
Original Assignee
Agence National de Valorisation de la Recherche ANVAR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Agence National de Valorisation de la Recherche ANVAR filed Critical Agence National de Valorisation de la Recherche ANVAR
Priority to FR7606820A priority Critical patent/FR2343483A1/en
Priority to US05/775,215 priority patent/US4153684A/en
Priority to AU22992/77A priority patent/AU516843B2/en
Priority to CA273,417A priority patent/CA1098515A/en
Priority to CH305277A priority patent/CH619469A5/en
Priority to GB10110/77A priority patent/GB1573126A/en
Priority to NL7702579A priority patent/NL7702579A/en
Priority to JP2552977A priority patent/JPS52139018A/en
Priority to DE2710454A priority patent/DE2710454C2/en
Priority to BE175701A priority patent/BE852349A/en
Priority to DK105477A priority patent/DK151813C/en
Publication of FR2343483A1 publication Critical patent/FR2343483A1/en
Application granted granted Critical
Publication of FR2343483B1 publication Critical patent/FR2343483B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • 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
    • 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
    • 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

Abstract

2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl- -D-glutamic acid esters and 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl- -D-isoglutamine of formula (I) are novel cpds. (where R1 = -OCnH2n+1 or -NH2; n = 1, 2 or 3; R2 = O-CpH2p+1 and p = 0, 1, 2 or 3 with the condition that p - O when R1 = -NH2). Cpds. (I) are anti-infectious agents and immunological adjuvants used to stimulate an innumitary response in a host to bacterial, viral and parasitory infections and against different tissular antigens. When using (I) it is not necessary to use a particular admin. medium e.g. for injectable solutions it is not necessary to have an oil phase. (I) may be administered by oral, parenteral (injection) or scarification methods or by application to mucous tissues. (I) have low toxicity and are well tolerated when administered parenterally to mice at 100 mg/kg and rabbits at 5 mg/kg. Their admin. with weak vaccine antigens is claimed.
FR7606820A 1976-03-10 1976-03-10 Immunogical adjuvants for weak vaccine antigens - are (2)-acetamido-deoxy (D)-glucopyranosyl (D)-propionyl (L)-alanyl (D)-glutamic acid esters and (D)-isoglutamines Granted FR2343483A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
FR7606820A FR2343483A1 (en) 1976-03-10 1976-03-10 Immunogical adjuvants for weak vaccine antigens - are (2)-acetamido-deoxy (D)-glucopyranosyl (D)-propionyl (L)-alanyl (D)-glutamic acid esters and (D)-isoglutamines
US05/775,215 US4153684A (en) 1976-03-10 1977-03-07 Immunizing and anti-infectious adjuvant agents constituted by N-acetyl-muramyl-L-alanyl-D-glutamic acid derivatives
CA273,417A CA1098515A (en) 1976-03-10 1977-03-08 Immunising and anti-infectious adjuvant agents constituted by esters of the n-acetyl-muramyl-l- alanyl-d-isoglutamine
AU22992/77A AU516843B2 (en) 1976-03-10 1977-03-08 Anti-infectious agent and -methyl esters
GB10110/77A GB1573126A (en) 1976-03-10 1977-03-10 Immunising and anti-infectious adjuvant agents comprising peptide derivatives of muramic acid
NL7702579A NL7702579A (en) 1976-03-10 1977-03-10 PROCESS FOR THE PREPARATION OF IMMUNISING AND ANTI-INFECTIOUS AGENTS.
CH305277A CH619469A5 (en) 1976-03-10 1977-03-10 Process for the preparation of the esters of N-acetyl-muramyl-L-alanyl-D-glutamic acid and of N-acetyl-muramyl-L-alanyl-D-isoglutamine
JP2552977A JPS52139018A (en) 1976-03-10 1977-03-10 Immuno adjuvant and antiinfection adjuvant composed of mainly nnacetyll muramiccllalanyllddglutamic ester or nnacetyllmuramiccllalanylldd isoglutamic ester
DE2710454A DE2710454C2 (en) 1976-03-10 1977-03-10 Esters of N-acetylmuramyl-L-alanyl-D-isoglutamine and mono- and diesters of N-acetylmuramyl-L-alanyl-D-glutamic acid, processes for their preparation and pharmaceutical compositions containing these compounds
BE175701A BE852349A (en) 1976-03-10 1977-03-10 IMMUNE AND ANTI-INFECTIOUS ADJUSTING AGENTS
DK105477A DK151813C (en) 1976-03-10 1977-03-10 METHOD OF ANALOGUE FOR THE PREPARATION OF ESTERS OF N-ACETYL-MURAMYL-L-ALANYL-D-GLUTAMIC ACID AND OF N-ACETYL-MURAMYL-L-ALANYL-D-ISOGLUTAMINE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7606820A FR2343483A1 (en) 1976-03-10 1976-03-10 Immunogical adjuvants for weak vaccine antigens - are (2)-acetamido-deoxy (D)-glucopyranosyl (D)-propionyl (L)-alanyl (D)-glutamic acid esters and (D)-isoglutamines

Publications (2)

Publication Number Publication Date
FR2343483A1 true FR2343483A1 (en) 1977-10-07
FR2343483B1 FR2343483B1 (en) 1979-06-29

Family

ID=9170213

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7606820A Granted FR2343483A1 (en) 1976-03-10 1976-03-10 Immunogical adjuvants for weak vaccine antigens - are (2)-acetamido-deoxy (D)-glucopyranosyl (D)-propionyl (L)-alanyl (D)-glutamic acid esters and (D)-isoglutamines

Country Status (4)

Country Link
AU (1) AU516843B2 (en)
BE (1) BE852349A (en)
CA (1) CA1098515A (en)
FR (1) FR2343483A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2533827A1 (en) * 1982-09-30 1984-04-06 Anvar Composition possessing immunoregulatory properties, in particular of non-specific immunological adjuvants, based on muramyl peptide and an aluminium derivative
US4652449A (en) * 1982-07-05 1987-03-24 Centre National De La Recherche Scientifique (Cnrs) Encapsulating biological active substances into erythrocytes
WO1996031533A1 (en) * 1995-04-07 1996-10-10 Vacsyn S.A. Mdp derivatives and conjugates having haematopoietic function stimulating activity, and compositions containing same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2428050A1 (en) * 1978-06-05 1980-01-04 Anvar OLIGOMERS OF MURAMYL-PEPTIDE COMPOUNDS AND DRUGS CONTAINING THEM
US4256735A (en) 1979-01-29 1981-03-17 Merck & Co., Inc. Immunologically active dipeptidyl saccharides and methods of preparation
US4391800A (en) 1979-04-27 1983-07-05 Merck & Co., Inc. Immunologically active peptidyl disaccharides and methods of preparation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH83A (en) * 1888-11-17 1889-01-10 Fontainemelon Horlogerie Improvements made to the construction of watches of all calibers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH83A (en) * 1888-11-17 1889-01-10 Fontainemelon Horlogerie Improvements made to the construction of watches of all calibers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1975 161 981Z CITE BIKEN J., 1975, 18, 105-111 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4652449A (en) * 1982-07-05 1987-03-24 Centre National De La Recherche Scientifique (Cnrs) Encapsulating biological active substances into erythrocytes
US4752586A (en) * 1982-07-05 1988-06-21 Centre National De La Recherche Scientifique Apparatus for encapsulating biological active substances into erythrocytes
FR2533827A1 (en) * 1982-09-30 1984-04-06 Anvar Composition possessing immunoregulatory properties, in particular of non-specific immunological adjuvants, based on muramyl peptide and an aluminium derivative
WO1996031533A1 (en) * 1995-04-07 1996-10-10 Vacsyn S.A. Mdp derivatives and conjugates having haematopoietic function stimulating activity, and compositions containing same
FR2732604A1 (en) * 1995-04-07 1996-10-11 Vacsyn Sa DERIVATIVES AND CONJUGATES OF THE CDM HAVING A STIMULATORY ACTIVITY OF HEMATOPOIETIC FUNCTION AND COMPOSITIONS CONTAINING SAME

Also Published As

Publication number Publication date
CA1098515A (en) 1981-03-31
FR2343483B1 (en) 1979-06-29
BE852349A (en) 1977-09-12
AU516843B2 (en) 1981-06-25
AU2299277A (en) 1978-09-14

Similar Documents

Publication Publication Date Title
NZ212796A (en) Pharmaceutical compositions containing xanthine derivatives and o-acetylsalicylic acid
KR910004572A (en) Azabicyclo quinolone carboxylic acid
EP0747383A3 (en) Polyamine salts of clavulanic acid
JPS5671074A (en) 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative
IE44190L (en) Glucosamine derivatives
SE8802790L (en) TRIPEPTIDES WITH IMMUNOSTIMULATING AND METASTAS PREVENTION EFFECTS
CA2003289A1 (en) Use of trifluoromethylphenyl-tetrahydropyridines for the preparation of pharmaceutical compositions useful for the treatment of anxiety and anxio-depressive disorders
FR2343483A1 (en) Immunogical adjuvants for weak vaccine antigens - are (2)-acetamido-deoxy (D)-glucopyranosyl (D)-propionyl (L)-alanyl (D)-glutamic acid esters and (D)-isoglutamines
HUP0100680A2 (en) Indole derivatives and medicinal compositions containing the same
Duffy Jr et al. ACTH and cortisone aggravation or suppression of the febrile response of rabbits to bacterial endotoxin
GB1342520A (en) Alpha-alkyl-substituted benzyl or thenyl-benzyloxy derivatives of amines
GB1195200A (en) Pharmaceutical Compositions.
GB1195199A (en) Improvements in Compositions comprising Insulin.
GB1163870A (en) Anti-Seborrhocic Compositions Suitable for Oral Administration
GB1290841A (en)
GB1214247A (en) N,n'-bis-(diphenylalkyl)-alkylene diamines
IE32592L (en) Anthranilic acid derivative
GB1495890A (en) Thioxanthenecarboxylic acid derivative
GB1354830A (en) 1,3-disubstituted thiourea compounds their preparation and use
EP0000644A3 (en) Lower cycloalkyl substituted-benzene derivatives, the preparation thereof and their pharmaceutical compositions
IE31963L (en) Pharmaceutical compositions
JPS525796A (en) Preparation of tetrahydropyrido pyrimidinone derivatives
GB1457237A (en) Cephalosporin compounds
FR2381041A1 (en) Antiulcer hydroxy-substd. di:carboxylic acid derivs. - prepd. e.g. by redn. of hydroxy-iso-canadenoic acid (BE 16.8.78)
KR940002268A (en) 21-chloro-pregnane derivative