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Last Updated: December 16, 2025

Claims for Patent: 12,128,033

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Summary for Patent: 12,128,033

Title:	Synthetic methods for preparation of 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine
Abstract:	The present disclosure relates to the fields of chemistry and medicine, more particularly to processes for making 4-(2-chloro-4-methoxy-5-methylphenyl)-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-N-prop-2-ynyl-1,3-thi-azol-2-amine (Compound 1), pharmaceutically acceptable salts, and crystalline forms thereof, for the treatment of congenital adrenal hyperplasia (CAH).
Inventor(s):	Andrew Becker, Joel Radisson
Assignee:	Sanofi SA , Neurocrine Biosciences Inc
Application Number:	US18/604,836
Patent Claims:	1. A compound that is 4-(2-chloro-4-methoxy-5-methylphenyl)-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-N-prop-2-ynyl-1,3-thiazol-2-amine (Compound 1): wherein the enantiomeric excess (e.e.%) of the compound is at least 99.7%. 2. The compound according to claim 1, wherein the enantiomeric excess (e.e.%) of Compound 1 is at least 99.8%. 3. The compound according to claim 1, wherein the enantiomeric excess (e.e.%) of Compound 1 is at least 99.9%. 4. A method of treating congenital adrenal hyperplasia (CAH), in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound according to claim 1. 5. The method according to claim 4, wherein the enantiomeric excess (e.e.%) of Compound 1 is at least 99.8%. 6. The method according to claim 4, wherein the enantiomeric excess (e.e.%) of Compound 1 is at least 99.9%. 7. The method according to claim 4, wherein the congenital adrenal hyperplasia is classic congenital adrenal hyperplasia. 8. The method according to claim 4, wherein the method further comprises administering to the subject a glucocorticoid. 9. The method according to claim 7, wherein the method further comprises administering to the subject a glucocorticoid. 10. A pharmaceutically acceptable salt of 4-(2-chloro-4-methoxy-5-methylphenyl)-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl) ethyl]-5-methyl-N-prop-2-ynyl-1,3-thiazol-2-amine (Compound 1): wherein the enantiomeric excess (e.e. %) of Compound 1 is at least 99.7%. 11. The salt according to claim 10, wherein the enantiomeric excess (e.e. %) of Compound 1 is at least 99.8%. 12. The salt according to claim 10, wherein the enantiomeric excess (e.e. %) of Compound 1 is at least 99.9%. 13. A method of treating congenital adrenal hyperplasia (CAH), in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a pharmaceutically acceptable salt of Compound 1 according to claim 10. 14. The method according to claim 13, wherein the enantiomeric excess (e.e. %) of Compound 1 is at least 99.8%. 15. The method according to claim 13, wherein the enantiomeric excess (e.e. %) of Compound 1 is at least 99.9%. 16. The method according to claim 13, wherein the congenital adrenal hyperplasia is classic congenital adrenal hyperplasia. 17. The method according to claim 13, wherein the method further comprises administering to the subject a glucocorticoid. 18. The method according to claim 16, wherein the method further comprises administering to the subject a glucocorticoid.

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