US2015072997A1PendingUtilityA1
Anti-malarial compounds
Est. expiryJul 28, 2028(~2 yrs left)· nominal 20-yr term from priority
Inventors:Richard W. ScottDoron GreenbaumDahui LiuXiaodong FanYongjiang XuHaizhong TangEhab M. Khalil
C07D 333/76C07C 217/90C07C 323/42A61P 31/00C07D 295/096C07D 239/28A61P 33/06C07D 207/12C07C 323/44C07D 335/12C07C 317/22C07D 295/135C07D 307/91A61K 31/381Y02A50/30
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Claims
Abstract
The present invention provides tricyclic compounds, arylamide compounds, and other compounds, and compositions comprising the same, for treating malaria, and methods of treating malaria comprising administering such compounds to an animal.
Claims
exact text as granted — not AI-modified1 - 224 . (canceled)
225 . A compound of Formula V:
wherein:
each X is, independently, O, S, or S(═O) 2 ;
each R 1 is, independently, —(CH 2 ) n —NH 2 , —(CH 2 ) n —NH—C(═NH)NH 2 , or —(CH 2 ) n —NH—C(═O)—R 4 , where each n is, independently, 1 to 4, and each R 4 is, independently, H, C 1 -C 3 alkyl, or —(CH 2 ) p —NH 2 , where each p is, independently, 1 or 2;
each R 2 is, independently, H, halo, CF 3 , or C(CH 3 ) 3 ; and
each V 2 is H, and each V 1 is, independently, —N—C(═O)—R 3 , where each R 3 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4; or each V 1 is H and each V 2 is, independently, —S—R 5 , where each R 5 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4;
or a pharmaceutically acceptable salt thereof;
provided that the compound is not:
226 . The compound or salt of claim 225 wherein each X is S.
227 . The compound or salt of claim 225 wherein each R 1 is, independently, —(CH 2 ) n —NH 2 , —(CH 2 ) n —NH—C(═NH)NH 2 , or —(CH 2 ) n —NH—C(═O)—R 4 , where each n is, independently, 1 or 2, and each R 4 is, independently, H or methyl.
228 - 230 . (canceled)
231 . The compound or salt of claim 225 wherein each R 2 is, independently, H, Br, F, Cl, CF 3 , or C(CH 3 ) 3 .
232 . (canceled)
233 . The compound or salt of claim 225 wherein each V 2 is H and each V 1 is, independently, —N—C(═O)—R 3 , where each R 3 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4.
234 - 236 . (canceled)
237 . The compound or salt of claim 225 wherein each V 1 is H and each V 2 is, independently, —S—R 5 , where each R 5 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4.
238 . (canceled)
239 . The compound or salt of claim 225 wherein each V 1 is H and each V 2 is, independently, —S—R 5 , where each R 5 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is 2.
240 . (canceled)
241 . The compound or salt of claim 225 wherein:
each X is S;
each R 1 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4;
each R 2 is, independently, halo, CF 3 , or C(CH 3 ) 3 ; and
each V 1 is H and each V 2 is, independently, —S—R 5 , where each R 5 is, independently, —(CH 2 ) n —NH 2 , where each n is, independently, 1 to 4.
242 - 246 . (canceled)
247 . The compound or salt of claim 225 wherein:
each X is O or S;
each R 1 is —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is 1 or 2;
each R 2 is halo, CF 3 , or C(CH 3 ) 3 ; and
each V 2 is H, and each V 1 is —N—C(═O)—R 3 , where each R 3 is —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is 3 or 4.
248 . (canceled)
249 . A compound chosen from:
or a pharmaceutically acceptable salt thereof.
250 . A composition comprising the compound or salt of claim 225 and a pharmaceutically acceptable carrier.
251 . A method of treating malaria in an animal or killing or inhibiting the growth of a Plasmodium species comprising administering to the animal a therapeutically effective amount of a compound of Formula V or contacting the species with an effective amount of a compound of Formula V:
wherein:
each X is, independently, O, S, or S(═O) 2 ;
each R 1 is, independently, —(CH 2 ) n —NH 2 , —(CH 2 ) n —NH—C(═NH)NH 2 , or —(CH 2 ) n —NH—C(═O)—R 4 , where each n is, independently, 1 to 4, and each R 4 is, independently, H, C 1 -C 3 alkyl, or —(CH 2 ) p —NH 2 , where each p is, independently, 1 or 2;
each R 2 is, independently, H, halo, CF 3 , or C(CH 3 ) 3 ; and
each V 2 is H, and each V 1 is, independently, —N—C(═O)—R 3 , where each R 3 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4; or each V 1 is H and each V 2 is, independently, —S—R 5 , where each R 5 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4;
or a pharmaceutically acceptable salt thereof.
252 . The method of claim 251 wherein each X is S.
253 . The method of claim 251 wherein each R 1 is, independently, —(CH 2 ) n —NH 2 , —(CH 2 ) n —NH—C(═NH)NH 2 , or —(CH 2 ) n —NH—C(═O)—R 4 , where each n is, independently, 1 or 2, and each R 4 is, independently, H or methyl.
254 - 256 . (canceled)
257 . The method of claim 251 wherein each R 2 is, independently, H, Br, F, Cl, CF 3 , or C(CH 3 ) 3 .
258 . (canceled)
259 . The method of claim 251 wherein each V 2 is H and each V 1 is, independently, —N—C(═O)—R 3 , where each R 3 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4.
260 - 262 . (canceled)
263 . The method of claim 251 wherein each V 1 is H and each V 2 is, independently, —S—R 5 , where each R 5 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4.
264 - 266 . (canceled)
267 . The method of claim 251 wherein:
each X is S;
each R 1 is, independently, —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is, independently, 1 to 4;
each R 2 is, independently, halo, CF 3 , or C(CH 3 ) 3 ; and
each V 1 is H and each V 2 is, independently, —S—R 5 , where each R 5 is, independently, —(CH 2 ) n —NH 2 , where each n is, independently, 1 to 4.
268 - 272 . (canceled)
273 . The method of claim 251 wherein:
each X is O or S;
each R 1 is —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is 1 or 2;
each R 2 is halo, CF 3 , or C(CH 3 ) 3 ; and
each V 2 is H, and each V 1 is —N—C(═O)—R 3 , where each R 3 is —(CH 2 ) n —NH 2 or —(CH 2 ) n —NH—C(═NH)NH 2 , where each n is 3 or 4.
274 . (canceled)
275 . The method of claim 251 wherein the compound is chosen from:
or a pharmaceutically acceptable salt thereof.
276 . The method of claim 251 wherein the malaria is chloroquine-sensitive or chloroquine-resistant.
277 - 375 . (canceled)Cited by (0)
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