Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
Assignee3M Innovative Properties Company
InventorsJohn F. Gerster, Kyle J. Lindstrom, Gregory J. Marszalek, Bryon A. Merrill, John W. Mickelson, Michael J. Rice
Life of this patent
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Abstract
Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.
Claims11
A method of inducing cytokine biosynthesis in a mammal comprising administering a composition comprising a therapeutically effective amount of a compound of the formula I:
- wherein:
- R1 is selected from the group consisting of oxygen, sulfur and selenium;
- R2 is selected from the group consisting of
- -hydrogen;
- -alkyl;
- -alkyl-OH;
- -haloalkyl;
- -alkenyl;
- -alkyl-X-alkyl;
- -alkyl-X-alkenyl;
- -alkenyl-X-alkyl;
- -alkenyl-X-alkenyl;
- -alkyl-N(R5)2;
- -alkyl-N3;
- -alkyl-O—C(O)—N(R5)2;
- -ayl-aryl;
- -alkyl-X-aryl;
- and
- -alkenyl-X-aryl;
- R3 and R4 are taken together to form a fused aromatic ring;
- X is selected from the group consisting of —O—, —S—, —NR5—, —C(O)—, —C(O)O—, —OC(O)—, and a bond;
- and
- each R5 is independently H or C1-8alkyl;
- or
- a pharmaceutically acceptable salt thereof, with a pharmaceutically acceptable carrier, to the mammal.
A method of treating a viral disease in a mammal comprising administering a composition comprising a therapeutically effective amount of a compound of the formula I:
- wherein:
- R1 is selected from the group consisting of oxygen, sulfur and selenium;
- R2 is selected from the group consisting of
- -hydrogen;
- -alkyl;
- -alkyl-OH;
- -haloalkyl;
- -alkenyl;
- -alkyl-X-alkyl;
- -alkyl-X-alkenyl;
- -alkenyl-X-alkyl;
- -alkenyl-X-alkenyl;
- -alkyl-N(R5)2;
- -alkyl-N3;
- -alkyl-O—C(O)—N(R5)2;
- -aryl;
- -alkyl-X-aryl;
- and
- -alkenyl-X-aryl;
- R3 and R4 are taken together to form a fused aromatic ring;
- X is selected from the group consisting of —O—, —S—, —NR5—, —C(O)—, —C(O)O—, —OC(O)—, and a bond;
- and
- each R5 is independently H or C1-8alkyl;
- or
- a pharmaceutically acceptable salt thereof, with a pharmaceutically acceptable carrier, to the mammal.
A method of treating a neoplastic disease in a mammal comprising administering a composition comprising a therapeutically effective amount of a compound of the formula I:
- wherein:
- R1 is selected from the group consisting of oxygen, sulfur and selenium;
- R2 is selected from the group consisting of
- -hydrogen;
- -alkyl;
- -alkyl-OH;
- -haloalkyl;
- -alkenyl;
- -alkyl-X-alkyl;
- -alkyl-X-alkenyl;
- -alkenyl-X-alkyl;
- -alkenyl-X-alkenyl;
- -alkyl-N(R5)2;
- -alkyl-N3;
- -alkyl-O—C(O)—N(R5)2;
- -aryl;
- -alkyl-X-aryl;
- and
- -alkenyl-X-aryl;
- R3 and R4 are taken together to form a fused aromatic ring;
- X is selected from the group consisting of —O—, —S—, —NR5—, —C(O)—, —C(O)O—, —OC(O)—, and a bond;
- and
- each R5 is independently H or C1-8alkyl;
- or
- a pharmaceutically acceptable salt thereof, with a pharmaceutically acceptable carrier, to the mammal.
Dependencies are inferred from the claim text.