Dimethylaminoethanol salt of a GLP-1 receptor modulator
Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl-[1,1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt, and methods related to synthesis and therapeutic use of the same.
1. A compound having the following structure:
2. The compound of claim 1 having the following structure:
3. The compound of claim 1 having the following structure:
4. The compound of claim 1 having the following structure:
5. A racemic mixture of the compounds of claims 3 and 4 .
6. Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl-[1,1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt.
7. Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl-[1,1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt having an XRPD pattern as shown in FIG. 1A .
8. Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl-[1,1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt having an XRPD pattern as shown in FIG. 2A .
9. Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl-[1,1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt having an XRPD pattern as shown in FIG. 3A .
10. Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl 1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt which exhibits an XRPD pattern having characteristic peaks expressed in distances (d-spacing) in degrees 2θ (+/−0.2° θ) as listed in Table 1A.
11. Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl 1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt which exhibits an XRPD pattern having characteristic peaks expressed in distances (d-spacing) in degrees 2θ (+/−0.2° θ) as listed in Table 1B.
12. Crystalline 2-hydroxy-N,N-dimethylethanaminium 1-(2-(5-(tert-butyl)-thiophene-2-carboxamido)-3-(4-(5-(4′-ethyl 1′-bi(cyclohexan)]-3-en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt which exhibits an XRPD pattern having characteristic peaks expressed in distances (d-spacing) in degrees 2θ (+/−0.2° θ) as listed in Table 1C.
13. The compound of any one of claim 1 , 2 or 6 having a purity in excess of 95% by weight.
14. The compound of any one of claim 1 , 2 or 6 having a purity in excess of 98% by weight.
15. A pharmaceutical composition comprising a compound of any one of claim 1 , 2 or 6 together with at least one pharmaceutically acceptable carrier, diluent or excipient.
16. A method of treating type II diabetes, comprising administering an effective amount of a compound of any one of claim 1 , 2 or 6 to a patient at a frequency and for a duration of time sufficient to provide a beneficial effect to the patient.