US2003109484A1PendingUtilityA1
Novel 2'-halomethylidene, 2'-ethenylidene and 2'ethynyl cytidine, uridine and guanosine derivatives
Priority: Nov 15, 1988Filed: Jun 6, 2002Published: Jun 12, 2003
Est. expiryNov 15, 2008(expired)· nominal 20-yr term from priority
C07H 19/06C07H 19/16
54
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Claims
Abstract
This invention relates to certain novel 2′-halomethylidene, 2′-ethenylidene and 2′-ethynyl cytidine, uridine and guanosine derivatives, and compositions thereof, which are useful in the treatment of patients afflicted with neoplastic or viral disease states.
Claims
exact text as granted — not AI-modified1 . A compound of the formula
wherein
V is oxy, methylene, or thio,
X 1 and X 2 are each independently hydrogen or halogen, with the proviso that at least one of X 1 and X 2 is halogen,
B is a radical of the formula
wherein Y 1 is nitrogen, a CH group, a CCl group, a CBr group or a CNH 2 group; Y 2 and Y 3 are each independently nitrogen or a CH group; Y 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; Y 5 is amino or C 1 -C 4 alkoxy; and Z is hydrogen, halogen, or NH 2 ;
or a pharmaceutically acceptable salt thereof.
2 . A compound of the formula
wherein
V is oxy, methylene, or thio,
R is hydrogen or C 1 -C 4 alkyl,
B is a radical of the formula
wherein Y 1 is nitrogen, a CH group, a CCl group, a CBr group or a CNH 2 group; Y 2 and Y 3 are each independently nitrogen or a CH group; Y 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; Y 5 is amino or C 1 -C 4 alkoxy; and Z is hydrogen, halogen, or NH 2 ;
or a pharmaceutically acceptable salt thereof.
3 . A compound of the formula
wherein
V is oxy, methylene, or thio,
A 1 and A 2 are each independently hydrogen or a —C CR group, wherein R is hydrogen or C 1 -C 4 alkyl, with the proviso that where A 1 is hydrogen A 2 is a —C CR group, and where A 1 is a —C CR group A 2 is hydrogen,
B is a radical of the formula
wherein Y 1 is nitrogen, a CH group, a CCl group, a CBr group or a CNH 2 group; Y 2 and Y 3 are each independently nitrogen or a CH group; Y 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; Y 5 is amino or C 1 -C 4 alkoxy; and Z is hydrogen, halogen, or NH 2 ;
or a pharmaceutically acceptable salt thereof.
4 . A compound of claim 1 wherein X 1 is fluoro and X 2 is hydrogen.
5 . A compound of claim 1 wherein X 1 is hydrogen and X 2 is fluoro.
6 . A compound of claim 2 or 3 wherein R is hydrogen.
7 . A compound of claim 1 , 2 or 3 wherein V is oxy.
8 . A compound of claim 1 , 2 or 3 wherein Z is hydrogen.
9 . A compound of claim 1 , 2 or 3 wherein Y 1 is a CH group.
10 . A compound of claim 1 , 2 or 3 wherein Y 2 is nitrogen.
11 . A compound of claim 1 , 2 or 3 wherein Y 3 is nitrogen.
12 . A compound of claim 1 , 2 or 3 wherein Z is hydrogen.
13 . A compound of claim 1 , 2 or 3 wherein Y 2 is a CH group.
14 . A method of treating a patient afflicted with a neoplastic disease state comprising the administration thereto of a therapeutically effective antineoplastic amount of a compound of claim 1 , 2 or 3 .
15 . A method of treating a patient afflicted with a viral infection comprising the administration thereto of a therapeutically effective antiviral amount of a compound of claim 1 , 2 or 3 .
16 . A method of controlling the growth of a neoplasm in a patient afflicted with a neoplastic disease state comprising administration thereto of a therapeutically effective antineoplastic amount of a compound of claim 1 , 2 or 3 .
17 . A method of controlling a viral infection in a patient afflicted therewith comprising administration thereto of a therapeutically effective antiviral amount of a compound of claim 1 , 2 or 3 .
18 . A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 , 2 or 3 in admixture or otherwise in association with one or more pharmaceutically acceptable carriers or excipients.
19 . A compound of claim 1 wherein the compound is 2′-deoxy-2′-difluoromethylidene-cytidine.
20 . The compound of claim 1 wherein the compound is 2′-deoxy-2′-difluoromethylidene-uridine.
21 . The compound of claim 1 wherein the compound is 2′-deoxy-2′-difluoromethylidene-guanosine.
22 . A compound of claim 1 wherein the compound is (E)-2′-deoxy-2′-fluoromethylidene-cytidine.
23 . A compound of claim 1 wherein the compound is (Z)-2′-deoxy-2′-fluoromethylidene-cytidine.
24 . A compound of claim 1 wherein the compound is (Z) or (E)-2′-deoxy-2′-fluoromethylidene-uridine.
25 . A compound of claim 1 wherein the compound is (z) or (E) 2′-deoxy-2′-fluoromethylidene-guanosine.
26 . The compound of claim 2 wherein the compound is 2′-deoxy-2′-ethenylidene-cytidine.
27 . The compound of claim 2 wherein the compound is 2′-deoxy-2′-ethenylidene-uridine.
28 . A compound of claim 2 wherein the compound is 2′-deoxy-2′-ethenylidene-guanosine.
29 . A compound of claim 3 wherein the compound is 2′-deoxy-2′ (R or S)-ethynyl-cytidine.
30 . A compound of claim 3 wherein the compound is 2′-deoxy-2′ (R or S)-ethynyl-uridine.
31 . A compound of claim 3 wherein the compound is 2′-deoxy-2′ (R or S)-ethynyl-guanosine.
32 . A compound of the formula
wherein
V is oxy, methylene, or thio,
X HAL is halogen,
Ar is a C 6 -C 12 aryl group,
B is a radical of the formula
wherein Y 1 is nitrogen, a CH group, a CCl group, a CBr group or a CNH 2 group; Y 2 and Y 3 are each independently nitrogen or a CH group; Y 4 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; Y 5 is amino or C 1 -C 4 alkoxy; and Z is hydrogen, halogen, or NH 2 .
33 . A compound of claim 32 wherein Ar is phenyl.
34 . A compound of claim 33 wherein X HAL is fluorine.
35 . A composition comprising a compound of claim 1 , 2 , 3 , or 32 in admixture or otherwise in association with an inert carrier.Join the waitlist — get patent alerts
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