Back to results
US 9,434,718 B2Granted
TOFA analogs useful in treating dermatological disorders or conditions
AssigneeDermira (Canada), Inc.
InventorsTimothy Scott Daynard, Geoffrey C. Winters, David W. C. Hunt
Life of this patent
Estimating the term…
Abstract
This invention is directed to analogs of 5-(tetradecyloxy)-2-furancarboxylic acid (TOFA) and their use in the treatment of dermatological disorders or conditions characterized by sebaceous gland hyperactivity, such as acne and oily skin, and other dermatological disorders and conditions. This invention is also directed to pharmaceutical compositions comprising analogs of TOFA and a pharmaceutically acceptable excipient for dermatological or oral administration.
Claims10
A compound of formula (I):
- wherein:
- R1 is —O—R3—OR2, —O—R3—OC(O)—N(R5)R6, —O—R3—N(R4)C(O)OR5, —O—R3—C(O)OR5, —O—R3—C(O)N(R5)R6 or —N(R5)S(O)2—R4;
- each R2 is independently alkyl, haloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl or optionally substituted heteroarylalkyl;
- each R3 is independently an optionally substituted alkylene chain;
- and
- R4 is optionally substituted alkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl or optionally substituted heteroarylalkyl;
- each R5 is independently hydrogen, alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted aralkyl;
- and
- each R6 is alkyl, optionally substituted cycloalkyl, optionally substituted aralkyl or —R3—C(O)OR4;
- or any R5 and R6, together with the nitrogen to which they are both attached, form an optionally substituted N-heterocyclyl or an optionally substituted N-heteroaryl;
- wherein, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted alkylene chain;
- optionally substituted cycloalkyl, optionally substituted N-heterocyclyl or optionally substituted N-heteroaryl may comprise one or more substituents selected from the group consisting of alkyl, akenyl, halo, haloalkyl, haloalkenyl, cyano, nitro, aryl, aralkyl, heteroaryl, heteroarylalkyl,
- —R15—OR14, —R15—OC(O)—R14, —R15—N(R14)2, —R15—C(O)R14, —R15—C(O)OR14, —R15—C(O)N(R14)2, —R15—N(R14)C(O)OR16, —R15—N(R14)C(O)R16, —R15—N(R14)S(O)tR16 (where t is 1 to 2), —R15—N═C(OR14)R14, —R15S(O)tOR16 (where t is 1 to 2), —R15—S(O)pR16 (where p is 0 to 2), and —R15—S(O)tN(R14)2 (where t is 1 to 2) wherein each R14 is independently hydrogen, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, heterocyclylalkyl, heteroaryl or heteroarylalkyl;
- each R15 is independently a direct bond or a straight or branched alkylene or alkenylene chain;
- and each R16 is alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, heterocyclylalkyl, heteroaryl or heteroarylalkyl,
- as a single stereoisomer or as a mixture thereof;
- or a pharmaceutically acceptable salt thereof.
14 more elements
Dependencies are inferred from the claim text.