US2005158329A1PendingUtilityA1

Novel phytol derived immunoadjuvants and their use in vaccine formulations

58
Priority: Jan 21, 2004Filed: Jan 21, 2004Published: Jul 21, 2005
Est. expiryJan 21, 2024(expired)· nominal 20-yr term from priority
Inventors:Swapan Kumar Ghosh
A61K 39/39A61K 2039/55511A61K 31/045
58
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Claims

Abstract

This invention relates to a novel immunoadjuvant, an adjuvant component, and vaccines containing the adjuvant component. The adjuvant includes phytol or a phytol derivative. The adjuvant component, when combined with a soluble or particulate antigen, provides a vaccine with an enhanced ability to induce both humoral and cytotoxic immune responses while displaying reduced toxicity and/or adverse side effects over vaccines that include the antigen but without the benefit of this adjuvant component.

Claims

exact text as granted — not AI-modified
1 . A composition comprising: 
 a vaccine preparation effective for treatment of a mammal in unit dosage form including:    an effective amount of an antigen;    an adjuvant component comprising phytol, isophytol, or a phytol derivative, said antigen homogenously dispersed in the adjuvant component; and optionally a carrier.    
     
     
         2 . The composition of  claim 1  wherein the adjuvant component comprises phytol.  
     
     
         3 . The composition of  claim 1  wherein the adjuvant component comprises isophytol.  
     
     
         4 . The composition of  claim 1  wherein the adjuvant component comprises phytanol.  
     
     
         5 . The composition of  claim 1  wherein the adjuvant component comprises a phytol derivative selected from the group consisting of: phytanol; 1-chloro-3,7,11,15-tetramethyl hexadec-2-ene; iodo-3,7,11,15-tetramethyl hexadeca-2-ene; 1-amino-3,7,11,15-tetramethyl hexadec-2-ene; 3,7,11,15-tetramethyl-hexadec-2-en-1-al; 3,7,11,15-tetramethyl-1-hexadecanal; 3,7,11,15-tetramethyl-1-hexadec-2-enyl acetate; 3,7,11,15-tetramethyl-1-hexadecanyl acetate; 1-chloro-3,7,11,15-tetramethyl hexadecane; 1-iodo-3,7,11,15-tetramethyl hexadecane; 1-amino-3,7,11,15-tetramethyl hexadecane; 1-methyl amino-3,7,11,15-tetramethyl hexadecane; stereoisomers and mixtures thereof.  
     
     
         6 . The composition of  claim 1  wherein the adjuvant component comprises phytol or a phytol derivative of the formula I or II:  
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group of chemical moieties, ions, or radicals consisting of: Br − , Cl − ; I − ; —NH 2 , —NO 2 , OH, PO 4   32 , HPO 4   − , NHR 2 , OC(O)R 2 , OR 2 , wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.  
       
     
     
         7 . The composition of  claim 1  wherein the antigen includes a T-independent antigen.  
     
     
         8 . The composition of  claim 7  wherein the antigen is selected from the group consisting of: polysaccharides, pneumococcus polysaccharides, bacterial lipopolysaccharides, synthetic lipoolysacchrarides, and hapten-polysaccharide conjugates.  
     
     
         9 . The composition of  claim 1  wherein the antigen includes a T-dependent antigen.  
     
     
         10 . The composition of  claim 9  wherein the antigen is selected from the group consisting of: proteins, peptides, lipoproteins, glycoproteins, gangliosides, cerebrosides, nucleoproteins, eukaroytic cellular isolates, and prokaryotic cellular isolates.  
     
     
         11 . The composition of  claim 1  wherein the carrier is sterile water at pH 7.0.  
     
     
         12 . The composition of  claim 1  wherein the carrier is comprises physiological buffers that include carbonates, bicarbonates, phosphates.  
     
     
         13 . The composition of  claim 1  wherein the vaccine composition is an oil-in-water emulsion.  
     
     
         14 . The composition of  claim 13  comprising a surfactant or emulsifier.  
     
     
         15 . The composition of  claim 14  wherein the emulsifier is selected from the group consisting of: phospholipids, lysophosphoglycerides, spingomyelin, phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl inositol and mixtures thereof.  
     
     
         16 . The composition of  claim 1  wherein the vaccine composition comprises the phytol or the phytol derivative and the antigen in a weight ratio of between about 1:4 to about 1:1.  
     
     
         17 - 26 . (canceled)  
     
     
         27 . A composition comprising a vaccine preparation in unit dosage form including an effective amount of an antigen conjugated directly to phytanol or a phytol derivative and a surfactant mixed in equal volume, and optionally a carrier or buffer solution.  
     
     
         28 . The composition of  claim 27  comprising between 4 and 100 micrograms of the antigen conjugated directly to phytanol or a phytol derivative.  
     
     
         29 . The composition of  claim 27  comprising between about 0.05 to about 0.1% (wt/v) of the surfactant.  
     
     
         30 . A composition comprising: 
 a vaccine preparation in unit dosage form including:    an effective amount of an antigen;    an adjuvant component comprising a phytol derivative; and optionally a liquid carrier.    
     
     
         31 . The composition of  claim 30  wherein the adjuvant component comprises a phytol derivative selected from the group consisting of: phytanol; 1-chloro-3,7,11,15-tetramethyl hexadec-2-ene; iodo-3,7,11,15-tetramethyl hexadeca-2-ene; 1-amino-3,7,11,15-tetramethyl hexadec-2-ene; 3,7,11,15-tetramethyl-hexadec-2-en-1-al; 3,7,11,15-tetramethyl-1-hexadecanal; 3,7,11,15-tetramethyl-1-hexadec-2-enyl acetate; 3,7,11,15-tetramethyl-1-hexadecanyl acetate; 1-chloro-3,7,11,15-tetramethyl hexadecane; 1-iodo-3,7,11,15-tetramethyl hexadecane; 1-amino-3,7,11,15-tetramethyl hexadecane; 1-methyl amino-3,7,11,15-tetramethyl hexadecane; stereoisomers and mixtures thereof.  
     
     
         32 . The composition of  claim 30  wherein the adjuvant component comprises a phytol derivative of the formula I:  
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group of chemical moieties, ions, or radicals consisting of: Br − , Cl − ; I − ; —NH 2 , —NO 2 , OH, PO 4   32 , HPO 4   − , NHR 2 , OC(O)R 2 , and OR 2 , wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.  
       
     
     
         33 . The composition of  claim 32  wherein R 1  is selected from —NH 2  or NHR 2  wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.  
     
     
         34 . The composition of  claim 32  wherein R 1  is selected from the group of chemical moieties consisting of: OH, OC(O)R 2 , and OR 2 , wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.  
     
     
         35 . The composition of  claim 32  wherein R 1  is selected from the group of chemical moieties consisting of: OH, PO 4   32 , and HPO 4   − .  
     
     
         36 . The composition of  claim 32  wherein R 1  is selected from the group of chemical moieties consisting of: Br − , Cl − ; and I − .  
     
     
         37 . The composition of  claim 32  comprising an emulsifier selected from the group consisting of: phospholipids such as phosphoglycerides, lysophosphoglycerides, spingomyelin, phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl inositol and mixtures thereof.  
     
     
         38 . The composition of  claim 32  comprising a surfactant selected from the group consisting of: mannide monooleates, 1,4-sorbitan, mono- and triesters, and polyoxyethylene derivatives of stearic acid.  
     
     
         39 . The composition of  claim 32  wherein the antigen is selected from the group consisting of: polysaccharides, pneumococcus polysaccharides, bacterial lipopolysaccharides, synthetic lipoolysacchrarides, and hapten-polysaccharide conjugates.  
     
     
         40 . The composition of  claim 32  wherein the antigen is selected from the group consisting of: proteins, peptides, lipoproteins, glycoproteins, ganliosides, cerebrosides, nucleoproteins, eukaroytic cellular isolates, and prokaryotic cellular isolates.  
     
     
         41 . The composition of  claim 30  wherein the adjuvant component comprises a phytol derivative of the formula II:  
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group of chemical moieties, ions, or radicals consisting of: Br − , Cl − ; I − ; —NH 2 , —NO 2 , OH, PO 4   32 , HPO 4   − , NHR 2 , OC(O)R 2 , OR 2 , wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.  
       
     
     
         42 . The composition of  claim 41  wherein R 1  is selected from —NH 2  or NHR 2  wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.  
     
     
         43 . The composition of  claim 41  wherein R 1  is selected from the group of chemical moieties consisting of: OH, OC(O)R 2 , and OR 2 , wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.  
     
     
         44 . The composition of  claim 41  wherein R 1  is selected from the group of chemical moieties consisting of: OH, PO 4   32 , and HPO 4   − .  
     
     
         45 . The composition of  claim 41  wherein R 1  is selected from the group of chemical moieties consisting of: Br − , Cl − ; and I − .  
     
     
         46 . The composition of  claim 41  comprising an emulsifier selected from the group consisting of: phosphoglycerides, lysophosphoglycerides, spingomyelin, phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl inositol and mixtures thereof.  
     
     
         47 . The composition of  claim 41  comprising a surfactant selected from the group consisting of: mannide monooleates, 1,4-sorbitan, mono- and triesters, and polyoxyethylene derivatives of stearic acid.  
     
     
         48 . The composition of  claim 41  wherein the antigen is selected from the group consisting of: polysaccharides, pneumococcus polysaccharides, bacterial lipopolysaccharides, synthetic lipoolysacchrarides, and hapten-polysaccharide conjugates.  
     
     
         49 . The composition of  claim 41  wherein the antigen is selected from the group consisting of: proteins, peptides, lipoproteins, glycoproteins, ganliosides, cerebrosides, nucleoproteins, eukaroytic cellular isolates, and prokaryotic cellular isolates.  
     
     
         50 . A method of enhancing the immunogenicity of a vaccine composition, said method comprising: 
 selecting an antigen eliciting a desired immunogenic response in a mammal, and combining the antigen with the phytol derivative of  claim 32  in a physiological acceptable carrier.    
     
     
         51 . A method of treating a patient, said method comprising: 
 preparing a vaccine formulation containing an antigen eliciting a desired immunogenic response in a mammal, and combining the antigen with the phytol derivative of  claim 32  in a physiological acceptable carrier; and    administering the vaccine formulation to the patient.    
     
     
         52 . A method of enhancing the immunogenicity of a vaccine composition, said method comprising: 
 selecting an antigen eliciting a desired immunogenic response in a mammal, and combining the antigen with the phytol derivative of  claim 41  in a physiological acceptable carrier.    
     
     
         53 . A method of treating a patient, said method comprising: 
 preparing a vaccine formulation containing an antigen eliciting a desired immunogenic response in a mammal, and combining the antigen with the phytol derivative of  claim 41  in a physiological acceptable carrier; and    administering the vaccine formulation to the patient.    
     
     
         54 . The composition of  claim 1  wherein the adjuvant component comprises phytol or a phytol derivative of the formula I or II:  
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group of ions consisting of: Br − , Cl − , and I − .  
       
     
     
         55 . The composition of  claim 1  wherein the adjuvant component comprises phytol or a phytol derivative of the formula I or II:  
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group of chemical moieties consisting of: —NH 2 , —NO 2 , and NHR 2 , wherein R is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate  
       
     
     
         56 . The composition of  claim 1  wherein the adjuvant component comprises phytol or a phytol derivative of the formula I or II:  
       
         
           
           
               
               
           
         
         wherein R 1  is selected from the group of chemical moieties, ions, or radicals consisting of: OH, OC(O)R 2 , OR 2 , wherein R 2  is a hydrocarbyl having 1 to 10 carbon atoms or a carbohydrate.

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