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US 12,156,864 B2Granted
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 amitriptyline analogs, including deuterated forms useful for treatment or prevention of symptoms associated with post-traumatic stress disorder.
Claims14
An amitriptyline 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;
- or R4 and R5 taken together can form a 4-membered saturated ring optionally substituted with methyl, methoxy, CF3, or CHF2.
5 more elements
A amitriptyline analog compound of Formula B,
- 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;
- or R4 and R5 taken together can form a 4-membered saturated ring optionally substituted with methyl or methoxy;
- or R4 and R5 taken together form a 4-membered saturated ring optionally substituted with CD3, CD3O, CF3, or CDF2, and with all other positions substituted with D;
- wherein the 3 carbons connecting nitrogen to the tricyclic ring system of Formula B are deuterated at all 5 positions (CDCD2CD2).
6 more elements
Dependencies are inferred from the claim text.