US2020338063A1PendingUtilityA1

Pharmaceutical compositions for the treatment of cftr mediated diseases

Assignee: VERTEX PHARMAPriority: Nov 2, 2012Filed: Dec 20, 2019Published: Oct 29, 2020
Est. expiryNov 2, 2032(~6.3 yrs left)· nominal 20-yr term from priority
A61K 45/06A61K 31/47A61K 31/443A61K 9/2095A61K 9/1605A61P 11/00A61P 3/12A61P 1/18A61P 1/00A61K 9/2077A61K 9/2054A61K 9/2027A61K 9/2013A61K 9/2004A61K 9/14A61K 9/10A61K 9/0053A61K 9/20A61P 43/00A61P 1/16
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Claims

Abstract

Pharmaceutical compositions comprising 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid (Compound 1) in Form I and a solid dispersion comprising substantially amorphous N-(5-hydroxy-2,4-ditert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (Compound 2), methods of treating, lessening the severity of, or symptomatically treating CFTR mediated diseases, such as cystic fibrosis, methods of manufacturing, methods of administering, and kits thereof are disclosed.

Claims

exact text as granted — not AI-modified
1 - 48 . (canceled) 
     
     
         49 . A pharmaceutical composition comprising 200 mg of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid (Compound 1) Form I and a solid dispersion comprising 125 mg of substantially amorphous N-(5-hydroxy-2,4-di-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (Compound 2). 
     
     
         50 . The pharmaceutical composition of  claim 49 , wherein the pharmaceutical composition is a tablet. 
     
     
         51 . The tablet of  claim 50 , wherein the tablet comprises 25 to 50 percent by weight of Compound 1 Form I, and 15 to 35 percent by weight solid dispersion comprising substantially amorphous Compound 2. 
     
     
         52 . The tablet of  claim 51 , further comprising:
 microcrystalline cellulose, in an amount of 20 to 30 percent by weight;   croscarmellose sodium, in an amount of 3 to 10 percent by weight;   sodium lauryl sulfate, in an amount of 0.5 to 2 percent by weight;   polyvinylpyrrolidone, in an amount of 0 to 5 percent by weight;   magnesium stearate, in an amount of 0.5 to 2 percent by weight; and   optionally further comprises a colorant and a wax.   
     
     
         53 . The tablet of  claim 52 , having a formulation selected from: 
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                     
                   % by wgt. 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   35 
                 
                     
                   Solid dispersion comprising 
                   28 
                 
                     
                   substantially amorphous 
                     
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   26 
                 
                     
                   Croscarmellose sodium 
                    6 
                 
                     
                   Sodium lauryl sulfate 
                    1 
                 
                     
                   Polyvinylpyrrolidone 
                    3 
                 
                     
                   Magnesium stearate 
                     1; 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                     
                   mg 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   200 
                 
                     
                   Solid dispersion comprising 
                   156 
                 
                     
                   substantially amorphous 
                     
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   150 
                 
                     
                   Croscarmellose sodium 
                    34 
                 
                     
                   Sodium lauryl sulfate 
                    4 
                 
                     
                   Polyvinylpyrrolidone 
                    15 
                 
                     
                   Magnesium stearate 
                     6; 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                     
                   % by wgt. 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   34 
                 
                     
                   Solid dispersion comprising 
                   27 
                 
                     
                   substantially amorphous 
                     
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   25 
                 
                     
                   Croscarmellose sodium 
                    6 
                 
                     
                   Sodium lauryl sulfate 
                    1 
                 
                     
                   Polyvinylpyrrolidone 
                    3 
                 
                     
                   Magnesium stearate 
                    1 
                 
                     
                   Colorant 
                     3; 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                     
                   mg 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   200 
                 
                     
                   Solid dispersion comprising 
                   156 
                 
                     
                   substantially amorphous 
                     
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   150 
                 
                     
                   Croscarmellose sodium 
                    34 
                 
                     
                   Sodium lauryl sulfate 
                    4 
                 
                     
                   Polyvinylpyrrolidone 
                    15 
                 
                     
                   Magnesium stearate 
                    6 
                 
                     
                   Colorant 
                     17; 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
                
               
            
           
         
         and 
       
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                     
                   mg 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   200 
                 
                     
                   Substantially amorphous 
                   125 
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   150 
                 
                     
                   Croscarmellose sodium 
                    34 
                 
                     
                   Sodium lauryl sulfate 
                    4 
                 
                     
                   Polyvinylpyrrolidone 
                    15 
                 
                     
                   Magnesium stearate 
                    6 
                 
                     
                   Colorant 
                     17. 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         54 . A tablet comprising a fixed dosage amount of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid (Compound 1) Form I and a solid dispersion comprising substantially amorphous N-(5-hydroxy-2,4-di-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (Compound 2),
 wherein the tablet comprises 25 to 50 percent by weight Compound 1 Form I and 15 to 35 percent by weight a solid dispersion comprising substantially amorphous Compound 2.   
     
     
         55 . The tablet of  claim 54 , wherein the composition further comprises:
 microcrystalline cellulose, in an amount of 20 to 30 percent by weight;   croscarmellose sodium, in an amount of 3 to 10 percent by weight;   sodium lauryl sulfate, in an amount of 0.5 to 2 percent by weight;   polyvinylpyrrolidone, in an amount of 0 to 5 percent by weight;   magnesium stearate, in an amount of 0.5 to 2 percent by weight; and   optionally comprises a colorant and a wax.   
     
     
         56 . A pharmaceutical composition comprising:
 a) about 100 mg of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid (Compound 1) Form I and about 125 mg of substantially amorphous N-(5-hydroxy-2,4-di-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (Compound 2);   b) about 150 mg of Compound 1 Form I and about 200 mg of substantially amorphous Compound 2; or   c) about 75 mg of Compound 1 Form I and about 100 mg of substantially amorphous Compound 2.   
     
     
         57 . The pharmaceutical composition of  claim 56 , wherein the pharmaceutical composition comprises 100 mg of Compound 1 Form I and 125 mg of substantially amorphous Compound 2. 
     
     
         58 . The pharmaceutical composition of  claim 57 , wherein the pharmaceutical composition is a tablet. 
     
     
         59 . The pharmaceutical composition of claim  48 , wherein the pharmaceutical composition comprises at least 20 percent by weight Compound 1 Form I, and at least 20 percent by weight substantially amorphous Compound 2. 
     
     
         60 . The pharmaceutical composition of  claim 59 , further comprising:
 microcrystalline cellulose, in an amount of 20 to 30 percent by weight;   croscarmellose sodium, in an amount of 3 to 10 percent by weight;   sodium lauryl sulfate, in an amount of 0.5 to 2 percent by weight;   polyvinylpyrrolidone, in an amount of 0 to 5 percent by weight; and   magnesium stearate, in an amount of 0.5 to 2 percent by weight.   
     
     
         61 . The pharmaceutical composition of  claim 59 , having the following formulation: 
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                   Component 
                   % by wgt. 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   20-40 
                 
                     
                   Solid dispersion comprising 
                   30-40 
                 
                     
                   substantially amorphous 
                     
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   20-30 
                 
                     
                   Croscarmellose sodium 
                    1-10 
                 
                     
                   Polyvinylpyrrolidone 
                   1-5 
                 
                     
                   Sodium lauryl sulfate 
                   0.1-1   
                 
                     
                   Magnesium stearate 
                    0.5-1.5. 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         62 . The pharmaceutical composition of  claim 61 , having the following formulation:
 25% of Compound 1 Form I, by weight of the composition;   38% of a solid dispersion comprising substantially amorphous Compound 2, by weight of the composition;   26% of microcrystalline cellulose, by weight of the composition;   6% of croscarmellose sodium, by weight of the composition;   1% of sodium lauryl sulfate, by weight of the composition; and   3% of polyvinylpyrrolidone, by weight of the composition.   
     
     
         63 . The pharmaceutical composition of  claim 57 , having the following formulation: 
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                   Component 
                   mg/Tablet 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   100 
                 
                     
                   Solid dispersion comprising 
                   156 
                 
                     
                   substantially amorphous 
                     
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   108 
                 
                     
                   Croscarmellose sodium 
                    25 
                 
                     
                   Polyvinylpyrrolidone 
                    11 
                 
                     
                   Sodium lauryl sulfate 
                    3 
                 
                     
                   Magnesium stearate 
                     4. 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         64 . The pharmaceutical composition of  claim 56 , wherein the pharmaceutical composition is a granular pharmaceutical composition. 
     
     
         65 . The pharmaceutical composition of  claim 64 , further comprising:
 microcrystalline cellulose, in an amount of 10 to 20 percent by weight;   croscarmellose sodium, in an amount of 1 to 3 percent by weight;   sodium lauryl sulfate, in an amount of 0.5 to 2 percent by weight; and   polyvinylpyrrolidone, in an amount of 0 to 5 percent by weight.   
     
     
         66 . The pharmaceutical composition of  claim 65 , having the following formulation: 
       
         
           
                 
                 
                 
               
                     
                     
                 
                     
                   Component 
                   % by wgt. 
                 
                     
                     
                 
                     
                   Compound 1 Form I 
                   30 
                 
                     
                   Solid dispersion comprising 
                   47 
                 
                     
                   substantially amorphous 
                     
                 
                     
                   Compound 2 
                     
                 
                     
                   Microcrystalline cellulose 
                   17 
                 
                     
                   Croscarmellose sodium 
                    2 
                 
                     
                   Polyvinylpyrrolidone 
                    3 
                 
                     
                   Sodium lauryl sulfate 
                     1. 
                 
                     
                     
                 
             
                
                
                
               
               
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         67 . A method of treating, lessening the severity of, or symptomatically treating cystic fibrosis in a patient comprising administering to the patient 800 mg of Compound 1 Form I and 500 mg of substantially amorphous Compound 2 daily. 
     
     
         68 . The method of  claim 57 , wherein the method comprises administering 400 mg of Compound 1 Form I and 250 mg of substantially amorphous Compound 2 every 12 hours. 
     
     
         69 . The method of  claim 68 , wherein the method comprises administering two dosage unit forms, each containing 200 mg of Compound 1 Form I and 125 mg of substantially amorphous Compound 2. 
     
     
         70 . A method of treating, lessening the severity of, or symptomatically treating cystic fibrosis in a patient comprising administering to the patient 400 mg of Compound 1 Form I and 500 mg of substantially amorphous Compound 2 daily. 
     
     
         71 . The method of  claim 70 , wherein the method comprises administering 200 mg of Compound 1 Form I and 250 mg of substantially amorphous Compound 2 every 12 hours. 
     
     
         72 . The method of  claim 71 , wherein the method comprises administering two dosage unit forms, each containing 100 mg of Compound 1 Form I and 125 mg of substantially amorphous Compound 2. 
     
     
         73 . A method of preparing a pharmaceutical composition, comprising wet granulating the following components:
 a. Compound 1 Form I;   b. a solid dispersion comprising substantially amorphous Compound 2;   c. a filler;   d. a disintegrant;   e. a surfactant; and   f. a binder.   
     
     
         74 . A method of preparing a tablet, comprising compressing the following components:
 i) a plurality of granules produced by the method of claim  25 ;   ii) a disintegrant;   iii) a filler; and   iv) a lubricant.   
     
     
         75 . A process for preparing a tablet comprising:
 a) mixing Compound 1 Form I, a solid dispersion comprising substantially amorphous Compound 2, a filler, and a disintegrant in a blender to form a blend;   b) preparing a granulation solution with water, a binder, and a surfactant;   c) feeding the blend from step a) into a continuous twin screw granulator while adding the granulation solution from step b) to produce granules;   d) drying the granules from step c) and milling them;   e) blending the milled granules from step d) with a filler, disintegrant, and lubricant to form a blend; and   f) compressing the blend from step e) into a tablet.

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