Low-viscosity liquid crystal compound

Abstract

The present invention relates to a liquid crystal compound that can be used as a base for injection formulations. The present invention provides an amphipathic compound having the following general formula (I): wherein X and Y each denotes a hydrogen atom or together denote an oxygen atom, n denotes an integer from 0 to 2, m denotes the integer 1 or 2, and R denotes a hydrophilic group generated by removal of one hydroxyl group from any one selected from the group consisting of glycerol, erythritol, pentaerythritol, diglycerol, triglycerol, xylose, sorbitol, ascorbic acid, glucose, galactose, mannose, dipentaerythritol, maltose, mannitol, and xylitol; as well as a base for injection formulations and depot formulation comprising the same.

1 . An amphipathic compound having the following general formula (I): 
       
         
           
           
               
               
           
         
         wherein X and Y each denotes a hydrogen atom or together denote an oxygen atom, n denotes the integer 0, m denotes the integer 1 or 2, and R denotes a hydrophilic group generated by removal of one hydroxyl group from any one selected from the group consisting of glycerol, erythritol, pentaerythritol, diglycerol, triglycerol, xylose, sorbitol, ascorbic acid, glucose, galactose, mannose, dipentaerythritol, maltose, mannitol, and xylitol. 
       
     
     
         2 . The compound according to  claim 1 , which has viscosity of 11.0 Pa·s or less as determined at 25° C. 
     
     
         3 . The compound according to  claim 1 , wherein X and Y together denote an oxygen atom, and R denotes a hydrophilic group generated by removal of one hydroxyl group from glycerol or diglycerol. 
     
     
         4 . The compound according to  claim 3 , wherein the compound is selected from the group consisting of:
 mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)glycerol,   mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)diglycerol,   mono-O-(3,7,11-trimethyldodec-2-enoyl)glycerol, and   mono-O-(3,7,11-trimethyldodec-2-enoyl)diglycerol.   
     
     
         5 . The compound according to  claim 1 , wherein R denotes a hydrophilic group generated by removal of one hydroxyl group from any one selected from the group consisting of erythritol, pentaerythritol, triglycerol, xylose, sorbitol, ascorbic acid, glucose, galactose, mannose, dipentaerythritol, maltose, mannitol, and xylitol. 
     
     
         6 . The compound according to  claim 5 , wherein the compound is selected from the group consisting of:
 mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)erythritol,   mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)pentaerythritol,   1-O-(3,7,11,15-tetramethylhexadec-2-enyl)-D-xylopyranoside,   mono-O-(3,7,11,15-tetramethylhexadec-2-enyl)erythritol,   mono-O-(3,7,11,15-tetramethylhexadec-2-enyl)pentaerythritol,   mono-O-(3,7,11-trimethyldodec-2-enoyl)erythritol,   mono-O-(3,7,11-trimethyldodec-2-enoyl)pentaerythritol,   1-O-(3,7,11-trimethyldodec-2-enyl)-D-xylopyranoside,   mono-O-(3,7,11-trimethyldodec-2-enyl)erythritol, and   mono-O-(3,7,11-trimethyldodec-2-enyl)pentaerythritol.   
     
     
         7 . The compound according to  claim 1 , wherein the compound is:
 mono-O-(3,7,11-trimethyldodec-2-enyl)glycerol, or   mono-O-(3,7,11-trimethyldodec-2-enyl)diglycerol.   
     
     
         8 . A base for injection formulations, which comprises at least one type of the compound according to  claim 1 . 
     
     
         9 . A depot formulation, which comprises the base according to  claim 8 . 
     
     
         10 . A composition comprising the compound according to  claim 1  and an active ingredient. 
     
     
         11 . The composition according to  claim 10 , wherein the composition further comprises an aqueous medium, and said amphipathic compound forms a non-lamellar liquid crystal in the composition. 
     
     
         12 . A method for administering an active ingredient to a subject, comprising administering the composition according to  claim 10 , wherein said amphipathic compound forms a non-lamellar liquid crystal in a living body of the subject. 
     
     
         13 . A method for administering an active ingredient to a subject, comprising administering the composition according to  claim 11 , wherein said amphipathic compound forms a non-lamellar liquid crystal in a living body of the subject.