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US 2025/0073204 A1Published application
Analogs of cyclobenzaprine and amitryptilene
AssigneeTonix Pharmaceuticals Holding Corp
InventorsSeth Lederman, Darryl Rideout, Greg Sullivan
Life of this patent
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Abstract
The present invention relates to cyclobenzaprine analogs and amitryptilene analogs, including deuterated forms useful for treatment or prevention of symptoms associated with post-traumatic stress disorder.
Claims52
A cyclobenzaprine analog compound of Formula A:
- and pharmaceutically acceptable salts thereof, wherein:
- R1 is selected from H, C1-4-alkyl, and C1-4-alkoxy;
- R2 is selected from H, Br, (CH2)nCO2R where n=0 to 3 and R═C1-4-alkyl, C1-4-alkoxy, and halogen;
- R3 is selected from H, C1-4-alkoxy, OH, and OCOR where R═C1-4-alkyl;
- R4 is C1-4-alkyl wherein if R4 is ethyl the terminus carbon can be optionally substituted by fluorine one to three times;
- and
- R4 and R5 taken together form a 4-membered saturated ring substituted with 1 or more fluorines and optionally further substituted with methyl, methoxy, CF3, or CHF2.
4 more elements
A cyclobenzaprine analog compound of Formula A
- and pharmaceutically acceptable salts thereof, wherein:
- R1 is selected from C1-4-alkyl, and C1-4-alkoxy;
- R2 is selected from H, Br, (CH2)nCO2R where n=0 to 3 and R═C1-4-alkyl, C1-4-alkoxy, and halogen;
- R3 is selected from H, C1-4-alkoxy, OH, and OCOR where R═C1-4-alkyl;
- R4 is C1-4-alkyl wherein if R4 is ethyl the terminus carbon can be optionally substituted by fluorine one to three times;
- and
- R5 is C1-4-alkyl;
- R4 and R5 taken together can form a fused 4-membered saturated ring optionally substituted with methyl, methoxy, CF3, or CHF2.
5 more elements
A cyclobenzaprine analog compound of Formula A
- and pharmaceutically acceptable salts thereof, wherein:
- R1 is H
- R2 is selected from H, Br, (CH2)nCO2R where n=0 to 3 and R═C1-4-alkyl, C1-4-alkoxy, and halogen;
- R3 is selected from H, C1-4-alkoxy, OH, and OCOR where R═C1-4-alkyl;
- R4 is methyl or 2,2-difluoroethyl
- R5 is C1-4-alkyl;
- R4 and R5 taken together can form a fused 4-membered saturated ring optionally substituted with methyl or methoxy.
4 more elements
A amitryptilene analog compound of Formula B
- and pharmaceutically acceptable salts thereof wherein:
- R1 is selected from H, C1-4-alkyl, and C1-4-alkoxy;
- R2 is selected from H, Br, (CH2)nCO2R where n=0 to 3 and R═C1-4-alkyl, C1-4-alkoxy, and halogen;
- R3 is selected from H, C1-4-alkoxy, OH, and OCOR where R═C1-4-alkyl;
- R4 is C1-4-alkyl wherein if R4 is ethyl the terminus carbon can be optionally substituted by fluorine one to three times;
- and
- R4 and R5 taken together form a 4-membered saturated ring substituted with 1 or more fluorines and optionally further substituted with methyl, methoxy, CF3, or CHF2.
4 more elements
A amitryptilene analog compound of Formula B
- and pharmaceutically acceptable salts thereof, wherein:
- R1 is selected from C1-4-alkyl, and C1-4-alkoxy;
- R2 is selected from H, Br, (CH2)nCO2R where n=0 to 3 and R═C1-4-alkyl, C1-4-alkoxy, and halogen;
- R3 is selected from H, C1-4-alkoxy, OH, and OCOR where R═C1-4-alkyl;
- R4 is C1-4-alkyl wherein if R4 is ethyl the terminus carbon can be optionally substituted by fluorine one to three times;
- and
- R5 is C1-4-alkyl;
- R4 and R5 taken together can form a fused 4-membered saturated ring optionally substituted with methyl, methoxy, CF3, or CHF2.
5 more elements
A amitryptilene analog compound of Formula B,
- pharmaceutically acceptable salts thereof, wherein:
- R1 is H
- R2 is selected from H, Br, (CH2)nCO2R where n=0 to 3 and R═C1-4-alkyl, C1-4-alkoxy, and halogen;
- R3 is selected from H, C1-4-alkoxy, OH, and OCOR where R═C1-4-alkyl;
- R4 is methyl or 2,2-difluoroethyl
- R5 is C1-4-alkyl;
- R4 and R5 taken together can form a fused 4-membered saturated ring optionally substituted with methyl or methoxy.
4 more elements
Dependencies are inferred from the claim text.