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US4185089A Expired / Lapsed US ⏱️ 0.0 years remaining

Immunological adjuvant constituted by the p-amino-phenyl derivative of N-acetyl-muramyl-L-alanyl-D-isoglutamine

Assignee: Bpifrance Financement SA
•
Filing: 1977-10-25
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Granted: 1980-01-22
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Expires: 1997-10-25
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Abstract

Abstract The adjuvant is 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propiony l-L-alanyl-D-isoglutamine, which compound in its beta glucoside form, corresponds with the formula <IMAGE> It is notably useful for favoring immunitory responses relative to antigens of low immunogenicity.

Inventors

  • 👤 Marcel Derrien
  • 👤 Edgar Lederer
  • 👤 Francoise M. Audibert
  • 👤 Louis Chedid
  • 👤 Jean Choay
  • 👤 Pierre LeFrancier

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 13:31
CPC Classifications
A; A61; A61K; A61K39/00; A61K39/39; A61P; A61P37/00; A61P37/02; A61P37/04; C; C07; C07K; C07K9/00; C07K9/001; C07K9/005; A61K2039/555; A61K2039/55511; A61K2039/5555

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 13 words
2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine, which compound, in its β glucoside form, corresponds to the formula ##STR3##
Claim 2
Dependent Claim 13 words
2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine, which compound, in its β glucoside form, corresponds to the formula ##STR3##
Claim 3
Dependent Claim 17 words
A biological composition which comprises a pharmaceutically acceptable carrier and an effective amount of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 4
Dependent Claim 17 words
A biological composition which comprises a pharmaceutically acceptable carrier and an effective amount of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 5
Dependent Claim 18 words
The composition according to claim 2, which is an injectable emulsion containing an effective dose of the compound.
Claim 6
Dependent Claim 13 words
The composition according to claim 3, which is a water and oil emulsion.
Claim 7
Dependent Claim 15 words
The composition according to claim 3, wherein the oil is constituted by a metabolisable oil.
Claim 8
Dependent Claim 16 words
The composition according to claim 2, wherein the compound therein is associated with an immunogenic agent.
Claim 9
Dependent Claim 17 words
Vaccine composition for human use containing an immunogenic agent and an effective dose of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 10
Dependent Claim 17 words
Vaccine composition for human use containing an immunogenic agent and an effective dose of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 11
Dependent Claim 17 words
Vaccine composition for veterinary use containing an immunogenic agent and an effective dose of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 12
Dependent Claim 17 words
Vaccine composition for veterinary use containing an immunogenic agent and an effective dose of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 13
Independent Claim 22 words
A method of treating diseases in humans or animals by administrering as an immunological adjuvant, an effective amount of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 14
Independent Claim 22 words
A method of treating diseases in humans or animals by administrering as an immunological adjuvant, an effective amount of the compound 2-(p-amino-phenyl-2-acetamido-2-deoxy-3-O-D-gluco-pyranosyl)-D-propionyl-L-alanyl-D-isoglutamine.
Claim 15
Dependent Claim 10 words
The composition of claim 2 which comprises also an immunogen.
Claim 16
Dependent Claim 16 words
The composition of claim 2 which has no pyrogenicity at dosage where the compound is adjuvant.
Claim 17
Dependent Claim 12 words
The composition of claim 10 wherein the immunogen is a weak immunogen.
Claim 18
Dependent Claim 18 words
The composition of claim 2 wherein the compound is in unit dosage of about 25 to 100 mg.
Claim 19
Dependent Claim 14 words
The method of claim 9 which comprises causing an immunogenic reaction but no pyrogenicity.

References Cited (Backward Citations)

US4082735A Cited
US4082736A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-01-21 1983-07-23 1984-01-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-01-21 1987-07-23 1988-01-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-01-21 1991-07-23 1992-01-22 $7700.00 Window Closed / Lapsed

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