Substituted imidazoquinolines
Assignee4Sc AG
InventorsVolker Gekeler, Thomas Maier, Astrid Zimmermann, Hans-Peter Hofmann, Sanjeev A. Kulkarni, Anil P. Jagtap, Ganesh S. Chaure
Life of this patent
Estimating the term…
Abstract
Imidazoquinolines of formula I that contain substituted amine or amide functionality at 1-position and that are effective as Toll like Receptor 7 activators are disclosed. These compounds are useful as anticancer agents.
Claims20
A method for treating a disease sensitive to TLR7 activation, or a method for treating a cancer sensitive to the activation of TLR7, or a method for treating a viral or neoplastic disease, or a method for activating TLR7,
- comprising administering to a subject in need thereof an effective amount of a compound of formula I
- wherein
- R1 is selected from the group consisting of:
- alkyl, alkynyl, aryl, alkoxy, heterocyclyl and heteroaryl,
- which alkyl, alkynyl, aryl, alkoxy, heterocyclyl or heteroaryl is unsubstituted or substituted by one or more substituents;
- A is C1-C6 alkyl;
- B is —N(R2)(R3);
- R2 is H or —(CO)—R5;
- R5 is selected from the group consisting of:
- alkyl, cycloalkyl, alkynyl, and heterocyclyl,
- each of which is unsubstituted or substituted by one or more substituents;
- R3 is heterocyclyl,
- which heterocyclyl is unsubstituted or substituted by one or more substituents;
- or a pharmaceutically acceptable solvate, salt, N-oxide or stereoisomer thereof,
- wherein at least one of the following conditions i to iv is satisfied:
- i) R2 is —(CO)—R5;
- ii) A is not propyl;
- iii) R1 is not butyl;
- iv) R3 does not encompass substituted piperidyl.
A method for treating a disease sensitive to TLR7 activation, or a method for treating a cancer sensitive to the activation of TLR7, or a method for treating a viral or neoplastic disease, or a method for activating TLR7,
- comprising administering to a subject in need thereof an effective amount of one of the following compounds
- N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-(1,1-dioxidotetrahydro-3-thienyl)acetamide,
- N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-(1-methyl-1-oxidopiperidin-4-yl)acetamide,
- 3-{acetyl[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]amino}-2,5-anhydro-1,3,4-trideoxypentitol,
- N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-(1-benzyl-2-methyl-1-oxidopyrrolidin-3-yl)acetamide,
- 2-ethyl-1-[4-(tetrahydro-2H-pyran-4-ylamino)butyl]-1H-imidazo[4,5-c]quinolin-4-amine,
- 1-[4-(1-azabicyclo[2.2.2]oct-3-ylamino)butyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine or
- 1-{4-[(1,1-dioxido-3,4-dihydro-2H-thiochromen-4-yl)amino]butyl}-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine,
- or a pharmaceutically acceptable solvate, salt, N-oxide or stereoisomer thereof.
A method for treating a disease sensitive to TLR7 activation, or a method for treating a cancer sensitive to the activation of TLR7, or a method for treating a viral or neoplastic disease, or a method for activating TLR7,
- comprising administering to a subject in need thereof an effective amount a compound of formula I
- wherein
- R1 is selected from the group consisting of:
- H, alkyl, alkynyl, aryl, alkoxy, heterocyclyl and heteroaryl,
- which alkyl, alkynyl, aryl, alkoxy, heterocyclyl or heteroaryl is unsubstituted or substituted by one or more substituents;
- A is C1-C6 alkyl;
- B is —N(R2)(R3);
- R2 is H or —(CO)—R5;
- R5 is selected from the group consisting of:
- alkyl, cycloalkyl, alkynyl, aryl, heterocyclyl and heteroaryl,
- each of which is unsubstituted or substituted by one or more substituents;
- R3 is selected from the group consisting of:
- —H, alkyl, alkenyl, aryl, heteroaryl, cycloalkyl, and heterocyclyl,
- which alkyl, alkenyl, aryl, heteroaryls, cycloalkyl or heterocyclyl is unsubstituted or substituted by one or more substituents;
- or a pharmaceutically acceptable solvate, salt, N-oxide or stereoisomer thereof.
Dependencies are inferred from the claim text.