US2023364092A1PendingUtilityA1

Solid forms of a toll-like receptor modulator

Assignee: GILEAD SCIENCES INCPriority: Apr 17, 2019Filed: Dec 13, 2022Published: Nov 16, 2023
Est. expiryApr 17, 2039(~12.7 yrs left)· nominal 20-yr term from priority
C07B 2200/13C07C 309/04C07C 59/255C07C 57/145C07C 57/15A61K 31/519A61K 31/7072A61K 31/522C07D 471/04A61K 45/06A61K 31/675A61P 31/20
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Claims

Abstract

The present disclosure provides crystalline forms, solvates and hydrates of (R)-2-((2-amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-1-ol, and methods of making.

Claims

exact text as granted — not AI-modified
1 .- 13 . (canceled) 
     
     
         14 . A crystalline form of (R)-2-((2-amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-1-ol hydrochloride: 
       
         
           
           
               
               
           
         
         characterized by an XRPD pattern comprising four more peaks at 6.1°, 12.2°, 15.0°, 17.3°, 17.8°, 18.9°, 20.3°, 23.2°, or 24.1° 2θ (±0.2° 2θ), hydrochloride salt Form I. 
       
     
     
         15 . (canceled) 
     
     
         16 . The crystalline form of  claim 14 , characterized by an XRPD pattern comprising peaks at 6.1°, 15.0°, and 17.8° 2θ (±0.2° 2θ). 
     
     
         17 . The crystalline form of  claim 16 , wherein the XRPD pattern further comprises one or more additional peaks at 12.2°, 17.3°, 18.9°, 20.3°, 23.2°, or 24.1° 2θ (±0.2° 2θ). 
     
     
         18 . The crystalline form of  claim 16 , wherein the XRPD pattern further comprises two or more additional peaks at 12.2°, 17.3°, 18.9°, 20.3°, 23.2°, or 24.1° 2θ (±0.2° 2θ). 
     
     
         19 . The crystalline form of  claim 14 , characterized by an XRPD pattern comprising peaks at 12.2°, 18.9°, and 24.1° 2θ (±0.2° 2θ). 
     
     
         20 . The crystalline form of  claim 19 , wherein the XRPD pattern further comprises one or more additional peaks at 6.1°, 15.0°, 17.3°, 17.8°, 20.3° and 23.2° 2θ (±0.2° 2θ). 
     
     
         21 . The crystalline form of  claim 19 , wherein the XRPD pattern further comprises two or more additional peaks at 6.1°, 15.0°, 17.3°, 17.8°, 20.3° and 23.2° 2θ (±0.2° 2θ). 
     
     
         22 . The crystalline form of  claim 14 , characterized by an XRPD pattern comprising peaks at 6.1°, 12.2°, 15.0°, 17.3°, 17.8°, 18.9°, 20.3°, 23.2°, and 24.1° 2θ (±0.2° 2θ). 
     
     
         23 . The crystalline form of  claim 14 , characterized by an XRPD pattern substantially as shown in  FIG.  5   . 
     
     
         24 . The crystalline form of  claim 14 , characterized by a differential scanning calorimetry (DSC) thermogram having an endotherm with an onset of about 135° C. 
     
     
         25 . The crystalline form of  claim 14 , characterized by a DSC thermogram substantially as shown in  FIG.  6   . 
     
     
         26 . A crystalline form of (R)-2-((2-amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-1-ol hydrochloride: 
       
         
           
           
               
               
           
         
         characterized by an XRPD pattern comprising four or more peaks at 7.1°, 9.7°, 14.3°, 15.3°, 16.1°, 19.1°, 22.5°, 24.0°, or 26.0° 2θ (±0.2° 2θ), hydrochloride salt Form II. 
       
     
     
         27 . (canceled) 
     
     
         28 . The crystalline form of  claim 26 , characterized by an XRPD pattern comprising peaks at 7.1°, 15.3°, and 24.0° 2θ (±0.2° 2θ). 
     
     
         29 . The crystalline form of  claim 28 , wherein the XRPD pattern further comprises one or more additional peaks at 9.7°, 14.3°, 16.1°, 19.1°, 22.5°, or 26.0° 2θ (±0.2° 2θ). 
     
     
         30 . The crystalline form of  claim 28 , wherein the XRPD pattern further comprises two or more additional peaks at 9.7°, 14.3°, 16.1°, 19.1°, 22.5°, or 26.0° 2θ (±0.2° 2θ). 
     
     
         31 . The crystalline form of  claim 26 , characterized by an XRPD pattern comprising peaks at 14.3°, 16.1°, and 26.0° 2θ (±0.2° 2θ). 
     
     
         32 . The crystalline form of  claim 31 , wherein the XRPD pattern further comprises one or more additional peaks at 7.1°, 9.7°, 15.3°, 19.1°, 22.5°, or 24.0° 2θ (±0.2° 2θ). 
     
     
         33 . The crystalline form of  claim 31 , wherein the XRPD pattern further comprises two or more additional peaks at 7.1°, 9.7°, 15.3°, 19.1°, 22.5°, or 24.0° 2θ (±0.2° 2θ). 
     
     
         34 . The crystalline form of  claim 31 , characterized by an XRPD pattern comprising peaks at 7.1°, 9.7°, 14.3°, 15.3°, 16.1°, 19.1°, 22.5°, 24.0°, and 26.0° 2θ (±0.2° 2θ). 
     
     
         35 . The crystalline form of  claim 26 , characterized by an XRPD pattern substantially as shown in  FIG.  9   . 
     
     
         36 . The crystalline form of  claim 26 , characterized by a differential scanning calorimetry (DSC) thermogram having an endotherm with an onset of about 58° C. 
     
     
         37 . The crystalline form of  claim 26 , characterized by a DSC thermogram substantially as shown in  FIG.  10   . 
     
     
         38 .- 121 . (canceled)

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