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.
Claims10
A compound of the formula I:
- ##STR68## wherein:
- R.sub.1 is selected from the group consisting of oxygen, sulfur and selenium;
- R.sub.2 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(R.sub.5).sub.2 ;
- -alkyl-N.sub.3 ;
- -alkyl-O--C(O)--N(R.sub.5).sub.2 ;
- -aryl;
- -alkyl-X-aryl;
- and
- -alkenyl-X-aryl;
- n is 1 to 4;
- each R is independently selected from the group consisting of
- -alkyl,
- -alkoxy,
- -alkylthio,
- -hydroxy,
- -halogen,
- -haloalkyl,
- -polyhaloalkyl,
- -perhaloalkyl,
- -trifluoroalkoxy,
- -nitro,
- -amino,
- -alkylamino,
- -dialkylamino,
- -alkylcarbonyl,
- -alkenylcarbonyl,
- -arylcarbonyl,
- -aryl,
- -arylalkyl,
- -nitrile and
- -alkoxycarbonyl;
- X is selected from the group consisting of --O--, --S--, --NR.sub.5 --, --C(O)--, --C(O)O--, --OC(O)--, and a bond;
- and
- each R.sub.5 is independently H or C.sub.1-8 alkyl;
- or a pharmaceutically acceptable salt thereof.
2-n-propylthiazolo[4,5-c]quinolin-4-amine, or a pharmaceutically acceptable salt thereof.
A compound selected from the group consisting of:
- 2-methylthiazolo[4,5-c]quinolin-4-amine;
- thiazolo[4,5-c]quinolin-4-amine;
- 2-ethylthiazolo[4,5-c]quinolin-4-amine;
- 2-propylthiazolo[4,5-c]quinolin-4-amine;
- 2-pentylthiazolo[4,5-c]quinolin-4-amine;
- 2-butylthiazolo[4,5-c]quinolin-4-amine;
- 2-(1-methylethyl)thiazolo[4,5-c]quinolin-4-amine;
- 2-(2-phenyl-1-ethenyl)thiazolo 4,5-c]quinolin-4-amine;
- 2-(2-phenyl-1-ethyl)thiazolo[4,5-c]quinolin-4-amine;
- 2-(4-aminothiazolo[4,5-c]quinolin-2-yl)-1,1-dimethylethyl carbamate;
- 2-(ethoxymethyl)thiazolo[4,5-c]quinolin-4-amine;
- 2-(methoxymethyl)thiazolo[4,5-c]quinolin-4-amine;
- 2-(2-methylpropyl)thiazolo[4,5-c]quinolin-4-amine;
- 2-benzylthiazolo[4,5-c]quinolin-4-amine;
- 8-methyl-2-propylthiazolo[4,5-c]quinolin-4-amine;
- (4-aminothiazolo[4,5-c]quinolin-2-yl)methanol;
- 2-methyloxazolo[4,5-c]quinolin-4-amine;
- 2-ethyloxazolo[4,5-c]quinolin-4-amine,
- 2-butyloxazolo[4,5-c]quinolin-4-amine;
- 2-propylthiazolo[4,5-c]quinolin-4,8-diamine;
- 2-propyloxazolo [4,5-c]quinolin-4-amine;
- 8-bromo-2-propylthiazolo[4,5-c]quinolin-4-amine;
- 7-methyl-2-propylthiazolo[4,5-c]quinolin-4-amine;
- 2-butyl-7-methyloxazolo[4,5-c]quinolin-4-amine;
- 7-methyl -2-propyloxazolo[4,5-c]quinolin-4-amine;
- 7-fluoro-2-propyloxazolo[4,5-c]quinolin-4-amine;
- 7-fluoro-2-propylthiazolo[4,5-c]quinolin-4-amine;
- 2-propyl -7-(trifluoromethyl)thiazolo[4,5-c]quinolin-4-amine;
- 7-chloro-2-propylthiazolo[4,5-c]quinolin-4-amine;
- 7-methoxy-2-propylthiazolo[4,5-c]quinolin-4-amine;
- and pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.