US2005203077A1PendingUtilityA1
Selenophene anti-tumor agents
Priority: Jun 3, 1996Filed: Apr 12, 2005Published: Sep 15, 2005
Est. expiryJun 3, 2016(expired)· nominal 20-yr term from priority
C07D 307/46C07D 421/14C07F 7/0838A61K 31/4025A61P 35/00C07D 333/22A61K 31/381A61K 31/34C07D 345/00
56
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Claims
Abstract
Novel selenophene compounds useful as anti-tumor agents are described. Preferred compounds include compounds of formula I: wherein R 1 and R 2 are independently selected from the group consisting of H, CHO, CH 2 OH and CH 2 NH 2 ; and X and Y are independently selected from the group consisting of Se, S, O, NCH 3 , and NH. Pharmaceutical compositions and a method for treating patients having tumors utilizing the disclosed selenophene compounds are also described.
Claims
exact text as granted — not AI-modified1 . A method for treating a patient having a tumor, said method comprising the step of administering to the patient an effective amount of a compound of the formula
wherein
R 1 and R 2 are independently selected from the group consisting of
H, CHO, CH 2 OH, and CH 2 NH 2 ; and
X and Y are independently selected from the group consisting of Se, S, O, NR, and NH, where R is H or C 1 -C 7 alkyl;
R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of H, CHO, CH 2 OH, and CH 2 NH 2 ; and when any one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is CH 2 NH 2 , the pharmaceutically acceptable salts thereof,
with the proviso that R 1 and R 2 are not both
2 . The method of claim 1 wherein the administering step includes the compound where R 1 and R 2 are each H.
3 . The method of claim 1 wherein the administering step includes the compound where R 3 and R 6 are each independently selected from the group consisting of CHO, CH 2 OH, and CH 2 NH 2 .
4 . The method of claim 3 wherein the administering step includes the compound where R 1 and R 2 are each H.
5 . The method of claim 1 wherein the administering step includes the compound where at least one of R 1 and R 2 is selected from the group consisting of CHO, CH 2 OH, and CH 2 NH 2 .
6 . The method of claim 1 wherein the administering step includes the compound where at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is selected from the group consisting of CHO, CH 2 OH, and CH 2 NH 2 .
7 . The method of claim 1 wherein the administering step includes the compound where one of R 1 and R 2 is selected from the group consisting of
8 . The method of claim 7 wherein the administering step includes the compound where at least one of R 3 , R 4 , R 5 , and R 6 is selected from the group consisting of CHO, CH 2 OH, and CH 2 NH 2 .
9 . The method of claim 7 wherein the administering step includes the compound where each of R 3 , R 4 , and R 6 is H.
10 . The method of claim 7 wherein the administering step includes the compound where the other of R 1 and R 2 is selected from the group consisting of CHO, CH 2 OH, and CH 2 NH 2 .
11 . The method of claim 7 wherein the administering step includes the compound where X is Se.
12 . The method of claim 1 wherein the administering step includes the compound where one of R 1 and R 2 is
13 . The method of claim 12 wherein the administering step includes the compound where the other of R 1 and R 2 is selected from the group consisting of CHO, CH 2 OH, and CH 2 NH 2 .
14 . The method of claim 12 wherein the administering step includes the compound where the R 5 is selected from the group consisting of CHO, CH 2 OH, and CH 2 NH 2 .
15 . The method of claim 12 wherein the administering step includes the compound where X is Se.
16 . The method of claim 1 wherein the administering step further comprises a pharmaceutically acceptable carrier therefor.
17 . The method of claim 1 wherein the administering step includes the compound as a complex with a cyclodextrin.
18 . A process for preparing an intermediate compound of the formula
the process comprising the step of reacting a compound of the formula
with a compound of the formula
in the presence of sodium cyanide and dimethylformamide;
wherein
X and Y are independently selected from the group consisting of Se, S, O, NR, and NH, where R is H or Cl-C 7 alkyl; and
R 1 , R 2 , R 3 , R 4 , and R 6 are each independently selected from the group consisting of H, CHO, CH 2 OH, and CH 2 NH 2 .
19 . A process for preparing a compound of the formula
the process comprising the step of reacting a compound of the formula
with a compound of the formula
in the presence of sodium cyanide and dimethylformamide to form an intermediate of the formula
wherein
X, Y, and Z are each independently selected from the group consisting of Se, S, O, NR, and NH, where R is H or C 1 -C 7 alkyl; and
R 1 , R 2 , R 3 , R 4 , and R 6 are each independently selected from the group consisting of H, CHO, CH 2 OH, and CH 2 NH 2 .
20 . The process of claim 19 further comprising the step of reacting the intermediate of the formula
with RNH 2 Cl in the presence of NaOAc, when Z is NR; with (CH 3 CO) 2 O in the presence of HCl, when Z is O; with [(C 6 H 11 ) 3 Sn] 2 S in the presence of BCl 3 , when Z is S; or with [(C 6 H 11 ) 3 Sn] 2 Se in the presence of BCl 3 , when Z is Se.
21 . The process of claim 20 wherein R 1 , R 2 , R 3 , R 4 , and R 6 are each H.
22 . The process of claim 21 further comprising the step of reacting the compound of the formula
with (a) base, and (b) dimethylformamide, to form a compound of the formula
wherein R 1 is selected from the group consisting of H and CHO.Join the waitlist — get patent alerts
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