US2011097269A1PendingUtilityA1
Phenyloxyaniline derivatives
Est. expirySep 4, 2026(~0.1 yrs left)· nominal 20-yr term from priority
C07F 7/1804A61K 51/04C07C 2601/14C07C 233/88C07C 309/66C07D 309/12A61K 49/04C07F 7/18C07C 309/69
38
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Claims
Abstract
The present invention relates to phenyloxyaniline derivatives, to methods of their production and to uses thereof.
Claims
exact text as granted — not AI-modified1 - 6 . (canceled)
7 . A compound of formula II:
wherein
A is
a) hydrogen
b) SiR 1 3
c) CH 2 -G
d) C(O)-Q
e) C(O)O-E
f) —(R 2 -phenyl)
g) —((R 2 )-2-phenyl)
h) tetrahydropyranyl
i) (1-alkoxy)-alkyl
j) (1-alkoxy)-cycloalkyl
k) allyl or
l) tert-butyl,
wherein G is
a) phenyl
b) alkoxy
c) dimethoxyphenyl
d) nitrophenyl
e) halophenyl
f) di-halophenyl
g) cyanophenyl
h) p-biphenyl
i) acylaminophenyl
j) triphenyl
k) (methoxyphenyl)phenyl
l) di(methoxyphenyl)phenyl
m) -naphtyldiphenyl, or
n) hydrogen
and Q is
a) hydrogen
b) C 1 -C 5 branched and unbranched alkyl
c) halomethyl
d) dihalomethyl
e) trihalomethyl
f) phenyl
g) biphenyl
h) triphenylmethoxymethyl and or
i) phenoxymethyl,
and E is
a) lower branched and unbranched alkyl
b) methoxymethyl
c) vinyl
d) allyl
e) benzyl
f) methoxyphenyl
g) dimethoxyphenyl or
h) nitrophenyl,
and wherein R 1 is
a) lower branched and unbranched alkyl,
b) phenyl, or
c) benzyl,
and wherein R 2 is
a) methoxy,
b) nitro,
c) halo, or
d) cyano.
8 . The compound according to claim 7 , wherein A is
a) hydrogen b) SiR 1 3 c) CH 2 -G d) tetrahydropyranyl e) allyl or f) tert-butyl.
9 . The compound according to claim 8 , wherein A is
a) hydrogen b) SiR 1 3 c) CH 2 -G d) tetrahydropyranyl, or e) tert-butyl.
10 . The compound according to claim 7 , wherein G is
a) phenyl b) methoxy c) p-methoxyphenyl d) p-nitrophenyl e) p-chlorophenyl, or f) triphenyl.
11 . The compound according to claim 9 , wherein G is
a) phenyl, b) methoxy, or c) p-methoxyphenyl.
12 . The compound according to claim 7 , wherein Q is
a) hydrogen b) methyl c) phenyl, or d) phenoxymethyl.
13 . The compound according to claim 12 , wherein Q is
a) methyl, or b) phenyl.
14 . The compound according to claim 7 , wherein E is
a) methyl b) tert-butyl c) methoxymethyl, or d) phenyl
15 . The compound according to claim 14 , wherein E is
a) methyl c) tert-butyl, or b) phenyl
16 . The compound according to claim 7 , wherein R 1 is
a) methyl b) ethyl c) isopropyl d) tert-butyl e) phenyl, or f) benzyl.
17 . The compound according to claim 16 , wherein R 1 is
a) methyl b) ethyl c) isopropyl d) tert-butyl, or e) phenyl.
18 . The compound according to claim 7 , wherein R 2 is
a) methoxy b) nitro, or c) chloro.
19 . The compound according to claim 18 , wherein R 2 a) methoxy, or b) nitro.
20 . The compound according to claim 7 , that is
21 . A process for preparing a compound of formula I:
wherein
R is
—OS(O) 2 -L
and wherein L is
a) methyl
b) trifluormethyl
c) nonafluorobutyl
d) C 1 -C 6 alkyl-phenyl
e) (2,4,6-C 1 -C 6 tri-alkyl)-phenyl
f) nitro-phenyl or
g) halo-phenyl
or a compound of formula I wherein L is (para-methyl)-phenyl, comprising:
a) reductively N-alkylating a compound of formula III:
with an aldehyde of formula IV
and subsequent N-acetylation, or
b) N-alkylating an aniline of formula V:
with an electrophile of formula VI
and subsequent N-acetylation, or
c) alkylation of phenol 4 with an
electrophile of formula VII
d) N-alkylating of the compound of formula VIII
with an electrophile of formula VI
wherein
X is a) nitro or
b) amino,
and
Z is, independently,
a) R,
b) tosyloxy, or
c) O-A, and
wherein R 3 is independently
a) R, or
b) tosyloxy.
22 . The process according to claim 21 , wherein Z is
a) methanesulphonyloxy b) trifluoromethansulphonyloxy c) nonafluorobutanesulfonyloxy d) tosyloxy e) bromo, or f) O-A.
23 . The process according to claim 22 , wherein Z is
a) methanesulphonyloxy b) trifluoromethansulphonyloxy c) nonafluorobutanesulfonyloxy d) tosyloxy e) bromo f) hydroxyl g) (tert-butyl dimethyl)silyloxy h) (triisopropyl)silyloxy ii) phenyl-methyl)oxy jj) (2-tetrahydropyranyl)oxy I, or kk) tert-butyloxy.
24 . The process according to claim 21 , wherein
R 3 is
a) R.
25 .- 29 . (canceled)
30 . A kit comprising a sealed vial containing a compound according to claim 7 wherein, said sealed vial contains a predetermined quantity of said compound.
31 . (canceled)
32 . A method diagnostic imaging comprising administering a diagnostically effective amount of a diagnostic imaging agent comprising a compound according to claim 7 .
33 . A method according to claim 32 , wherein said diagnostic imaging agent is far administered to image diseases of the central nervous system.
34 . A process of preparing compound 3
comprising
a) reacting compound 7
with 18 F anions,
at temperatures in the range of from 121° C. to 160° C., and, optionally, upon obtainment of compound 3, adding acid.
35 . The process of preparing compound 3
comprising
reacting a compound of formula I,
wherein
R is —OS(O) 2 -L
and wherein L is
a) methyl
b) trifluormethyl
c) nonafluorobutyl
d) C 1 -C 6 alkyl-phenyl
e) (2,4,6-C 1 -C 6 tri-alkyl)-phenyl
f) nitro-phenyl or
g) halo-phenyl
with the proviso that L is not (para-methyl)-phenyl.
with 18 F anions at temperatures in the range of from 75° C. to 150° C.
36 . The process according to claim 35 , wherein said temperatures are in the range of from 85° C. to 140° C.
37 . The process according to claim 34 ,
comprising reacting compound 7 with 18 F anions at temperatures in the range of from 121° C. to 150° C., and, optionally, upon obtainment of compound 3, adding at least one mineral acid having a concentration in the range of from 0.5N-6N.
38 . The process according to claim 34 ,
comprising reacting compound 7 with 18 F anions, at temperatures in the range of from 121° C. to 140° C., and, optionally upon obtainment of compound 3, adding at least one mineral acid having a concentration in the range of from 2N-6N.Cited by (0)
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