US2009036482A1PendingUtilityA1
Imidazopyridine-derivatives as inductible no-synthase inhibitors
Est. expiryOct 1, 2023(expired)· nominal 20-yr term from priority
Inventors:Wolf-Ruediger Ulrich
A61P 9/10A61P 9/00A61P 43/00A61P 25/16A61P 31/00A61P 27/02A61P 25/02A61P 29/00A61P 25/00A61P 3/10A61P 25/28A61P 25/06A61P 11/08C07D 471/04A61P 11/06A61P 17/06A61P 19/02A61P 1/04A61K 31/437A61P 17/00
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Claims
Abstract
The compounds of Formula (I) in which R1, R2, R3, R4, R5 and A have the meanings as given in the description are novel effective iNOS inhibitors.
Claims
exact text as granted — not AI-modified1 .- 14 . (canceled)
15 . A method for treating an acute inflammatory disease in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula I
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen or 1-4C-alkyl,
R3 is hydrogen or halogen,
R4 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
R5 is 1-4C-alkyl,
A is 1-4C-alkylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
16 . The method of claim 15 , wherein said compound has one of the formulae Ia, Ib or Ic:
or a salt, N-oxide or a salt of an N-oxide thereof.
17 . The method of claim 15 , wherein said compound has one of the formulae I, Ia, Ib or Ic
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen or 1-4C-alkyl,
R3 is hydrogen or halogen,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
18 . The method of claim 15 , wherein said compound has one of the formulae I, Ia, Ib or Ic
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl,
R3 is hydrogen or fluorine,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
19 . The method of claim 15 , wherein said compound has one of the formulae I, Ia, Ib or Ic
in which
either
R1 is methyl,
R2 is methyl, and
R3 is fluorine,
or
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl, and
R3 is hydrogen,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
20 . The method of claim 15 , wherein said compound has one of the formulae Ib or Ic
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl,
R3 is hydrogen or fluorine,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
21 . The method of claim 15 , wherein said compound has the formula Ic
in which
either
R1 is methyl,
R2 is methyl, and
R3 is fluorine,
or
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl, and
R3 is hydrogen,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
22 . The method of claim 15 , wherein said compound has the formula Id
(Id)
in which R1, R2 and R3 have any one of the following meanings 1 to 12:
R1
R2
R3
1.
H
H
H
2.
H
CH 3
H
3.
H
CH 2 CH 3
H
4.
H
H
F
5.
H
CH 3
F
6.
H
CH 2 CH 3
F
7.
CH 2 CH 3
CH 2 CH 3
H
8.
CH 3
CH 3
H
9.
CH 3
CH 2 CH 3
H
10.
CH 2 CH 3
CH 2 CH 3
F
11.
CH 3
CH 3
F
12.
CH 3
CH 2 CH 3
F
or a salt, N-oxide or a salt of an N-oxide thereof.
23 . A method for treating a chronic inflammatory disease of peripheral organs and the central nervous system (CNS) in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula I
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen or 1-4C-alkyl,
R3 is hydrogen or halogen,
R4 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
R5 is 1-4C-alkyl,
A is 1-4C-alkylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
24 . The method of claim 23 , wherein said compound has one of the formulae Ia, Ib or Ic:
or a salt, N-oxide or a salt of an N-oxide thereof.
25 . The method of claim 23 , wherein said compound has one of the formulae I, Ia, Ib or Ic
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen or 1-4C-alkyl,
R3 is hydrogen or halogen,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
26 . The method of claim 23 , wherein said compound has one of the formulae I, Ia, Ib or Ic
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen; methyl or ethyl,
R3 is hydrogen or fluorine,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
27 . The method of claim 23 , wherein said compound has one of the formulae I, Ia, Ib or Ic
in which
either
R1 is methyl,
R2 is methyl, and
R3 is fluorine,
or
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl, and
R3 is hydrogen,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
28 . The method of claim 23 , wherein said compound has one of the formulae Ib or Ic
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl,
R3 is hydrogen or fluorine,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
29 . The method of claim 23 , wherein said compound has the formula Ic
in which
either
R1 is methyl,
R2 is methyl, and
R3 is fluorine,
or
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl, and
R3 is hydrogen,
R4 is hydrogen,
R5 is methyl,
A is ethylene,
or a salt, N-oxide or a salt of an N-oxide thereof.
30 . The method of claim 23 , wherein said compound has the formula Id
(Id)
in which R1, R2 and R3 have any one of the following meanings 1 to 12:
R1
R2
R3
1.
H
H
H
2.
H
CH 3
H
3.
H
CH 2 CH 3
H
4.
H
H
F
5.
H
CH 3
F
6.
H
CH 2 CH 3
F
7.
CH 2 CH 3
CH 2 CH 3
H
8.
CH 3
CH 3
H
9.
CH 3
CH 2 CH 3
H
10.
CH 2 CH 3
CH 2 CH 3
F
11.
CH 3
CH 3
F
12.
CH 3
CH 2 CH 3
F
or a salt, N-oxide or a salt of an N-oxide thereof.Join the waitlist — get patent alerts
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