Analgesic compounds
AssigneeRecurium IP Holdings, LLC
InventorsChad Daniel Hopkins, Joseph Robert Pinchman, Kevin Duane Bunker, Deborah Helen Slee, Brant Clayton Boren, Mehmet Kahraman
Life of this patent
Estimating the term…
Abstract
Disclosed herein are compounds of Formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ik), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is) and (It), methods of synthesizing compounds of Formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ik), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is) and (It), and methods of using compounds of Formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), (Ik), (Im), (In), (Io), (Ip), (Iq), (Ir), (Is) and (It) as an analgesic.
Claims26
A compound selected from:
- wherein:
- each X1, each X2, each X3, each X4, each X5, each X6, each X7, each X11, each X12, each X13 and each X14 are independently hydrogen, deuterium, an unsubstituted C1-4 alkyl, fluoro or chloro, provided that at least two of X1 is fluoro or chloro, provided that at least two of X2 is fluoro or chloro, provided that at least two of X3 is fluoro or chloro, provided that at least two of X4 is fluoro or chloro, provided that at least two of X5 is fluoro or chloro, provided that at least two of X6 is fluoro or chloro, provided that at least two of X7 is fluoro or chloro, provided that at least two of X11 is fluoro or chloro, provided that at least two of X12 is fluoro or chloro, provided that at least two of X13 is fluoro or chloro, and provided that at least two of X14 is fluoro or chloro;
- each X8, each X9 and X10 are independently deuterium, fluoro or chloro;
- R1 is an unsubstituted H2N—CH(R″)—C(═O)—NH—, wherein R″ is a side chain of an α-amino acid, or an unsubstituted
- R2 and R3 are independently an unsubstituted C1-4 alkyl;
- R9a and R9b are independently an unsubstituted C1-4 alkyl;
- R5A, R5B, R5D, R5E, R5F, R5G, R5H, R6J, R5K and R5L are independently hydrogen, deuterium or an unsubstituted C1-4 alkyl;
- R5C is selected from the group consisting of hydrogen, deuterium, an unsubstituted C1-4 alkyl and C(═O)R12;
- R4a and R4b are independently hydrogen, deuterium, an unsubstituted C1-4 alkyl, a hydroxy substituted C1-4 alkyl or —C(X16)3, provided that at least one of R4a and R4b is —C(X16)3;
- R6, R7 and R8 are independently —(CH2)m—;
- R10 is selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, an unsubstituted C1-8 alkyl, an unsubstituted C3-20 cycloalkyl and an unsubstituted C1-8 haloalkyl;
- R11 is selected from the group consisting of hydrogen, deuterium, halogen, an unsubstituted C1-30 alkyl, an unsubstituted C2-30 alkenyl and an unsubstituted C1-8 haloalkyl;
- R12 is selected from the group consisting of hydrogen, deuterium, an unsubstituted C1-30 alkyl and an unsubstituted C2-30 alkenyl;
- each X16 is independently hydrogen, deuterium, an unsubstituted C1-4 alkyl, fluoro or chloro, provided that at least two of X16 is fluoro or chloro;
- Z1, Z2 and Z3 are independently nitrogen, oxygen or sulfur;
- m is 1, 2, 3 or 4;
- each XA, each XB, each XC, each XD, each XE, each XL, each XG, each XH, each XJ, each XK, each XL, each XM, each XN, each XP, each XQ, each XR and each XS are independently deuterium, chloro or fluoro;
- p1, p2, p3, p4, p5, p6, p7, p8, p9, p10, p11, p12, p13, p14, p15 and p16 are independently 0, 1, 2, 3, 4, 5 or 6;
- p17 is 1, 2, 3, 4, 5 or 6;
- or a pharmaceutically acceptable salt thereof;
- and
- wherein the compound is not selected from the group consisting of:
- or a pharmaceutically acceptable salt of any of the foregoing.
-13. (canceled)
The compound of claim 4, or a pharmaceutically acceptable salt thereof, wherein R4a is —C(X16)3;
- and R4b is hydrogen.
-52. (canceled)
(canceled)
-64. (canceled)
-77. (canceled)
Dependencies are inferred from the claim text.