US2015203527A1PendingUtilityA1
Cationic steroidal antimicrobials
Individually held — no corporate assignee on recordPriority: Jan 23, 2014Filed: Jan 21, 2015Published: Jul 23, 2015
Est. expiryJan 23, 2034(~7.5 yrs left)· nominal 20-yr term from priority
Inventors:Paul B. Savage
C07J 41/0055C07J 41/0088
54
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
Disclosed herein are cationic steroidal antimicrobials (“CSA compounds” or “ceragenins”) and methods of making the same. Particularly advantageous methods are identified for the synthesis of CSA compounds. CSA compounds may be formulated for treating subjects with ailments responsive to CSA compounds, including but not limited to treating bacterial infections. Accordingly, some embodiments include formulations and methods of administering CSA compounds.
Claims
exact text as granted — not AI-modified1 . A compound of Formula (I), or a pharmaceutically acceptable salt thereof:
wherein
R 1 is selected from the group consisting of an optionally substituted C 11-22 -alkylamino-C x -alkyl; an optionally substituted C 8-22 -alkylester-C x -alkyl; and an optionally substituted Z 1 ,Z 2 -amino-C x -alkyl;
R 2 , R 3 , and R 4 , are independently selected from the group consisting of optionally substituted amino-C a -alkyl and optionally substituted amino-C a -alkylcarbonyl;
x is 1-5;
Z 1 and Z 2 are independently C 6-22 -alkyl; and
a is 2-5,
with the proviso that when R 2 , R 3 , and R 4 are each unsubstituted amino-C 3 -alkyl, R 1 is not unsubstituted C 16 -alkylamino-C 3 -alkyl,
with the proviso that when R 2 , R 3 , and R 4 are each the same unsubstituted amino-C 2-4 -alkylcarbonyl, R 1 is not unsubstituted C 9 -alkylcarboxylic ester-C 2 -alkyl, and
with the proviso that when R 2 , R 3 , and R 4 are each unsubstituted amino-C 3 -alkyl, Z 1 and Z 2 are not both C 8 -alkyl.
2 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein R 1 is an optionally substituted C 11-22 -alkylamino-C x -alkyl.
3 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 2 , wherein R 1 is an optionally substituted C 11-15 -alkylamino-C x -alkyl.
4 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 2 , wherein R 1 is an optionally substituted C 16 -alkylamino-C x -alkyl, with the proviso that R 2 , R 3 , and R 4 are not all unsubstituted amino-C 3 -alkyl.
5 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 2 , wherein R 1 is an optionally substituted C 17 -C 22 -alkylamino-C x -alkyl.
6 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein R 1 is an optionally substituted C 8-22 -alkylester-C x -alkyl.
7 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 6 , wherein R 1 is an optionally substituted C 8 -alkylester-C x -alkyl.
8 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 6 , wherein R 1 is an optionally substituted C 9 -alkylester-C x -alkyl, with the proviso that when R 1 is an unsubstituted C 9 -alkylcarboxylic ester-C 2 -alkyl, R 2 , R 3 , and R 4 are not all the same unsubstituted amino-C 2-4 -alkylcarbonyl.
9 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 6 , wherein R 1 is an optionally substituted C 10 -alkylester-C x -alkyl.
10 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 6 , wherein R 1 is an optionally substituted C 11 -alkylester-C x -alkyl.
11 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 6 , wherein R 1 is an optionally substituted C 12-22 -alkylester-C x -alkyl.
12 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 6 , wherein the ester is a carboxylic ester selected from oxycarbonyl or carbonyloxy.
13 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein R 1 is an optionally substituted Z 1 ,Z 2 -amino-C x -alkyl.
14 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 13 , wherein Z 1 and Z 2 are the same.
15 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 13 , wherein Z 1 and Z 2 are different.
16 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 13 , wherein at least one or Z 1 or Z 2 is C 6-7 -alkyl.
17 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 13 , wherein at least one of Z 1 or Z 2 is C 8 -alkyl, with the proviso that when R 2 , R 3 , and R 4 are amino-C 3 -alkyl Z 1 and Z 2 are not both C 8 -alkyl.
18 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 13 , wherein at least one or Z 1 or Z 2 is C 9-22 -alkyl.
19 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein x is 1.
20 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein x is 2.
21 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein x is 3.
22 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein x is 4.
23 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein x is 5.
24 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein two or three of R 2 , R 3 , and R 4 are the same.
25 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein R 2 , R 3 , and R 4 are all different.
26 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein a is 2.
27 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein a is 3.
28 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein a is 4.
29 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein a is 5.
30 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein R 2 , R 3 , and R 4 are optionally substituted amino-C a -alkyl.
31 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein R 2 , R 3 , and R 4 are optionally substituted amino-C a -alkylcarbonyl.
32 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein one or more of R 1 , R 2 , R 3 , and R 4 is unsubstituted.
33 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein two or more of R 1 , R 2 , R 3 , and R 4 are unsubstituted.
34 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein three or more of R 1 , R 2 , R 3 , and R 4 are unsubstituted.
35 . The compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are unsubstituted.
36 . A pharmaceutical composition comprising at one compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 and a pharmaceutically acceptable excipient.
37 . A pharmaceutical composition as in claim 36 , wherein the pharmaceutically acceptable excipient comprises a liquid.
38 . A pharmaceutical composition as in claim 36 , wherein the pharmaceutically acceptable excipient comprises a solid.
39 . A composition of matter comprising at one compound of Formula (I), or a pharmaceutically acceptable salt thereof, as in claim 1 and at least one carrier.
40 . A composition of matter as in claim 39 , wherein the carrier is a liquid.
41 . A composition of matter as in claim 39 , wherein the carrier is a solid.
42 . A cationic steroidal antimicrobial (CSA) compound selected from the group consisting of:
and
pharmaceutically acceptable salts thereof.
43 . A cationic steroidal antimicrobial CSA compound as in claim 42 , wherein the CSA compound is selected from the group consisting of:
and
pharmaceutically acceptable salts thereof.
44 . A cationic steroidal antimicrobial CSA compound as in claim 42 , wherein the CSA compound is selected from the group consisting of:
and
pharmaceutically acceptable salts thereof.
45 . A cationic steroidal antimicrobial CSA compound as in claim 42 , wherein the CSA compound is selected from the group consisting of:
pharmaceutically acceptable salts thereof.Join the waitlist — get patent alerts
Track US2015203527A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.