US2004072858A1PendingUtilityA1
Heterocyclic ether substituted imidazoquinolines
Assignee: 3M INNOVATIVE PROPERTIES COPriority: Dec 8, 2000Filed: Sep 30, 2003Published: Apr 15, 2004
Est. expiryDec 8, 2020(expired)· nominal 20-yr term from priority
Inventors:Leslie J. CharlesJoseph F. DellariaGeorge W. GriesgraberPhilip D. HeppnerKarl J. ManskeJohn MickelsonMichael J. Rice
C07D 471/04A61P 37/02A61P 31/12
48
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Claims
Abstract
Imidazoquinoline and tetrahydroimidazoquinoline compounds that contain ether and heterocyclyl or heteroaryl functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of the formula (I):
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CHR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaiyl;
-heterocyclyl;
—R 4 -heteroaryl; and
—R 4 -heterocyclyl;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO-C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more 4-groups;
each R 3 is independently H or C 1-10 alkyl;
each Y is independently —O— or —S(O) 0-2 —;
n is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
2 . A compound or salt of claim 1 wherein R 1 is CH 2 ) 0-3 -heteroaryl.
3 . A compound or salt of claim 2 wherein the heteroaryl is selected from the group consisting of 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 2-pyrimidinyl, 4-pyrimidinyl, 4-triazolyl, 2-benzofuranyl, 2-indolyl, 3-carbazolyl, 2-furanyl, 4-isoquinolinyl, 4-isoxazolyl, and 4-pyrazolyl
4 . A compound or salt of claim 1 wherein X is —CH(alkyl)(alkyl)— wherein the alkyl groups can be the same or different.
5 . A compound or salt of claim 1 wherein X is —CH 2 CH 2 —.
6 . A compound or salt of claim 1 wherein X is CH(C 2 H 5 )(CH 2 ).
7 . A compound or salt of claim 1 wherein R 2 is H.
8 . A compound or salt of claim 1 wherein R 2 is alkyl.
9 . A compound or salt of claim 1 wherein R 2 is -alkyl-O-alkyl.
10 . A compound of the formula (II)
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CHR 3 -alkenyl-;
R 10 is selected from the group consisting of heteroaryl and heterocyclyl;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
-alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO-C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
n is 0 to 4;
each R 3 is independently H or C 1-10 alkyl;
each Y is independently —O— or —S(O) 0-2 —; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
11 . A compound or salt of claim 10 wherein R 10 is selected from the group consisting of heteroaryl and substituted heteroaryl.
12 . A compound of claim 11 wherein the heteroaryl is selected from the group consisting of 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 4-pyrazolyl, 3-furanyl, 2-thienyl, and 2-pyrimidinyl.
13 . A compound or salt of claim 10 wherein X is —CH(alkyl)(alkyl), wherein the alkyl groups can be the same or different.
14 . A compound or salt of claim 10 wherein X is —CH 2 —CH 2 —.
15 . A compound or salt of claim 10 wherein X is —CH(C 2 H 5 )(CH 2 )—.
16 . A compound or salt of claim 10 wherein R 2 is H, alkyl, or alkyl-O-alkyl.
17 . A compound selected from the group consisting of:
1-(2-{[3-(isoquinolin-4-yl)-2-propynyl]oxy} ethyl)-1H-imidazo[4,5-c]quinolin4-amine; 1-(2-{[3-(1,3-thiazol-2-yl)-2-propynyl]oxy} ethyl)-1H-imidazo[4,5-c]quinolin4-amine; 1-{2-[3-(1H-4-pyrazolyl)propoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine, 1-[2-(3-pyrimidin-2-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine; 1-[2-(3-pyridin-4-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin4-amine; 1-[2-(3-pyridin-2-ylpropoxy)ethyl]-H-imidazo[4,5-c]quinolin-4-amine; 1-{2-[3-(1,3-thiazol-2-yl)propoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine; 1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine; 1-[2-(3-pyrimidin-5-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin4-amine; 1-{2-[(1−benzyl-1 H-1,2,3-triazol-4-yl)methoxy]ethyl}-1H-imidazo[4,5-c]quinoline-4-amine; 1-{2-[(1−benzyl-1 H-1,2,3-triazol-5-yl)methoxy]ethyl}-1H-imidazo[4,5-c]quinoline-4-amine; 1-[2-({1-[(henylsulfanyl)methyl]-1H-1,2,3-triazol-4-yl}methoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine; 1-[2-({1-[(phenylsulfanyl)methyl]-1H-1,2,3-triazol-5-yl}methoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine; 1-[2-(benzo[b]furan-2-ylmethoxy)ethyl]-1H-iihidazo[4,5-c]quinolin-4-amine; 1-[2-(pyridin-3-ylmethoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine; 1-[2-(pyridin-2-ylmethoxy)ethyl]-1H-imidazo[4,5-c]quinolin4-amine; 1-[2-(pyridin4-ylmethoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine; 1-{2-[(3,5-dimethylisoxazol-4-yl)methoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine; 1-(2-{[3-(pyrimidin-2-yl)-2-propynyl]oxy} ethyl)-1H-imidazo[4,5-c]quinolin4-amine; 1-(2-{[3-(pyrid-4-yl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine; 1-(2-{[3-(fur-3-yl)-2-propynyl]oxy} ethyl)-1H-imidazo[4 , 5-c]quinolin-4-amine; 4-{3-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]-propyn-1-yl} thiophen-2-ylcarboxaldehyde; 1-(2-{[3-(pyrid-2-yl)-2-propynyl]oxy} ethyl)-1H-imidazo[4,5-c]quinolin-4-amine; 1-{2-methyl-1-[(pyrid-2-yloxy)methyl]propyl}-1H-imidazo[4,5-c]quinoline-4-amine; 1-{1-[(pyrid-2-yloxy)methyl]propyl}-1H-imidazo[4,5-c]quinoline-4-amine; 1-[2-(9H-carbazol-3-yloxy)propyl] j 1 H-imidazo[4,5-c]quinolin-4-amine; 1-{2-[(3-thien-2-ylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine; 1-{2-[(1-methyl-1H-indol-2-yl)methoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine; 1-[2-(3-thien-2-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine; 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine; 2-butyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinoline-4-amine; 1-[2-(tetrahydrofuran-2-ylmethoxy)propyl]-1H-imidazo[4,5-c]quinolin-4-amine; 1-{2-[(5-chloro-1-benzothien-3-yl)methoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine; 1-{2-[(3-nitropyridin-2-yl)oxy]propyl}-1H-imidazo[4,5-c]quinolin4-amine; 1-(2-methyl-1-{[(3-nitropyridin-2-yl)oxy]methyl}propyl)-1H-imidaz6[4,5-c]quinolin-4-amine; 1-(1-{[(5-chloro-1-benzothien-3-yl)methoxy]methyl}-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine; 2-(2-methoxyethyl)-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine; and 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine; or a pharmaceutically acceptable salt thereof.
18 . A compound of the formula (III)
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CHR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaryl;
-heterocyclyl;
—R 4 -heteroaryl; and
—R 4 -heterocyclyl;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO—C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more 4-groups;
each R 3 is independently H or C 1-10 alkyl;
each Y is independently —O— or —S(O) 0-2 —;
n is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
19 . A compound or salt of claim 18 wherein R 2 is H or alkyl.
20 . A compound or salt of claim 18 wherein R 2 is -alkyl-O-alkyl.
21 . A compound of the formula (IV):
wherein: X is —CHR 3 —, —CHR 3 -allcyl-, or —CHR 3 -alkenyl-;
R 10 is selected from the group consisting of heteroaryl and heterocyclyl;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y— alkenyl;
-alkyl-Y-aryl; and
alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO-C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
each R 3 is independently H or C 1-10 alkyl;
each Y is independently 0 or —S(O) 0-2 —;
n is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
22 . A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 1 and a pharmaceutically acceptable carrier.
23 . A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 10 and a pharmaceutically acceptable carrier.
24 . A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 17 and a pharmaceutically acceptable carrier.
25 . A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 1 to the animal.
26 . The method of claim 25 wherein the cytokine is IFN-α.
27 . A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 10 to the animal.
28 . The method of claim 27 wherein the cytokine is IFN-α.
29 . A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 1 to the animal.
30 . A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 1 to the animal.
31 . A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 10 to the animal.
32 . A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 10 to the animal.
33 . A method of inducing cytokine biosynthesis in an animal comprising administering a theraputically effective amount of a compound or salt of claim 17 to the animal.
34 . The method of claim 33 wherein the cytokine is IFN-α.
35 . A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 17 to the animal.
36 . A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 17 to the animal.
37 . A compound of the formula (V):
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CLIR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaryl;
-heterocyclyl;
—R 4 -heteroaryl;
—R 4 -heterocyclyl; and
—(CH 2 ) 1-10 —C≡C—R 10 ;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
-alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO-C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more groups;
each R 3 is independently H or C 1-10 alkyl;
R 10 is heteroaryl or heterocyclyl;
each Y is independently —O— or —S(O) 0-2 —;
D is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
38 . A compound of the formula (VI):
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CHR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaryl;
-heterocyclyl;
—R 4 -heteroaryl;
—R 4 -heterocyclyl; and
-(CH 2 ) 1-10 —C≡C—R 10 ;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO-C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more —O-groups;
each R 3 is independently H or C 1-10 alkyl;
R 10 is heteroaryl or heterocyclyl;
each Y is independently or —S(O) 0-2 —;
n is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
39 . A compound of the formula (VIII):
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CHR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaryl;
-heterocyclyl;
—R 4 -heteroaryl; and
—R 4 -heterocyclyl;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 );
—CO—C 1-10 alkyl;
—CO—O—C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more groups;
each R 3 is independently H or C 1-10 alkyl;
each Y is independently —O— or —S(O)O 2 —;
n is 0 to 4;
each R present is independently selected from the group consisting of C 1-10 to alkyl, C 1-10 alkoxy, hydroxy, halogen and ttifluoromethyl; and
R 7 is ieri-butyl or benzyl;
or a pharmaceutically acceptable salt thereof.
40 . A compound of the formula (IX)
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CHR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaryl;
-heterocyclyl;
—R 4 -heteroaryl; and
—R 4 -heterocyclyl;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
-alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO-C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
each R 3 is independently H or C 1-10 alkyl;
each Y is independently —O— or —S(O) 0-2 —;
n is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
41 . A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 18 and a pharmaceutically acceptable carrier.
42 . A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 18 to the animal.
43 . The method of claim 42 wherein the cytokine is IFN-α.
44 . A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 18 to the animal.
45 . A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 18 to the animal.
46 . A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 21 and a pharmaceutically acceptable carrier.
47 . A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 21 to the animal.
48 . The method of claim 47 wherein the cytokine is IFN-α.
49 . A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 21 to the animal.
50 . A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 21 to the animal.
51 . A compound of the formula (VII):
wherein: Z is NH 2 or NO 2 ;
X is —CHR 3 —, —CHR 3 -alkyl-, or CHR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaryl;
-heterocyclyl;
—R 4 -heteroaryl; and
—R 4 -heterocyclyl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
each R 3 is independently H or C 1-10 alkyl;
n is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alkyl, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.
52 . A compound of the formula (XLIV):
wherein: X is —CHR 3 —, —CHR 3 -alkyl-, or —CHR 3 -alkenyl-;
R 1 is selected from the group consisting of:
-heteroaryl;
-heterocyclyl;
—R 4 -heteroaryl; and
—R 4 -heterocyclyl;
R 2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-heteroaryl;
-heterocyclyl;
-alkyl-Y-alkyl;
-alkyl-Y-alkenyl;
-alkyl-Y-aryl; and
alkyl or alkenyl substituted by one or more substiutients selected from the group consisting of:
—OH;
-halogen;
—N(R 3 ) 2 ;
—CO—N(R 3 ) 2 ;
—CO-C 1-10 alkyl;
—CO—O-C 1-10 alkyl;
—N 3 ;
-aryl;
-heteroaryl;
-heterocyclyl;
—CO-aryl; and
—CO-heteroaryl;
R 4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
each R 3 is independently H or C 1-10 alkyl;
each Y is independently A or —S(O) 0-2 —;
n is 0 to 4; and
each R present is independently selected from the group consisting of C 1-10 alky, C 1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
or a pharmaceutically acceptable salt thereof.Join the waitlist — get patent alerts
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