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US 2009/0264418 A1Published application
5-amido-indole-2-carboxamide derivatives
AssigneeHoffman-La Roche Inc.
InventorsMatthias Nettekoven, Jean-Marc Plancher, Hans Richter, Olivier Roche, Sven Taylor
Life of this patent
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Abstract
The present invention relates to compounds of formula I wherein G and R1 to R5 and R12 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.
Claims17
A compound of formula I:
- wherein:
- R1 is selected from the group consisting of
- lower alkyl, lower alkenyl, lower alkinyl,
- cycloalkyl, lower cycloalkylalkyl,
- lower hydroxyalkyl,
- lower alkoxyalkyl,
- lower alkylsulfanylalkyl,
- lower dialkylaminoalkyl,
- lower dialkylcarbamoylalkyl,
- phenyl unsubstituted or substituted with one to three groups independently selected from lower alkyl, halogen, lower halogenalkoxy and lower hydroxyalkyl,
- lower phenylalkyl wherein the phenyl ring may be unsubstituted or substituted with one to three groups independently selected from lower alkyl, halogen, lower alkoxy and lower hydroxyalkyl,
- lower heteroarylalkyl wherein the heteroaryl ring may be unsubstituted or substituted with one or two groups independently selected from lower alkyl, halogen, lower alkoxy and lower hydroxyalkyl,
- lower heterocyclylalkyl wherein the heterocyclyl ring may be unsubstituted or substituted with one or two groups selected from lower alkyl and halogen, and
- 7-oxa-bicyclo[2.2.1]heptyl;
- R2 is selected from the group consisting of hydrogen,
- lower alkyl, lower alkenyl, lower alkinyl,
- cycloalkyl, lower cycloalkylalkyl,
- lower hydroxyalkyl, lower alkoxyalkyl,
- lower alkylsulfanylalkyl,
- lower dialkylaminoalkyl,
- lower dialkylcarbamoylalkyl,
- phenyl unsubstituted or substituted with one to three groups independently selected from lower alkyl, halogen, lower halogenalkoxy and lower hydroxyalkyl,
- lower phenylalkyl wherein the phenyl ring may be unsubstituted or substituted with one to three groups independently selected from lower alkyl, halogen, lower alkoxy and lower hydroxyalkyl,
- lower heteroarylalkyl wherein the heteroaryl ring may be unsubstituted or substituted with one or two groups independently selected from lower alkyl, halogen, lower alkoxy and lower hydroxyalkyl, and
- lower heterocyclylalkyl wherein the heterocycly ring may be unsubstituted or substituted with one or two lower alkyl groups;
- or
- R1 and R2 together with the nitrogen atom to which they are attached form a 4-, 5-, 6- or 7-membered saturated or partly unsaturated heterocyclic ring optionally containing a further heteroatom selected from oxygen or sulfur, a sulfinyl group or a sulfonyl group, said heterocyclic ring
- being unsubstituted or substituted by one, two or three groups independently selected from lower alkyl, halogen, lower halogenalkyl, cyano, hydroxy, lower hydroxyalkyl, lower alkoxy, oxo, phenyl, benzyl, pyridyl and carbamoyl, or
- being condensed with a phenyl ring, said phenyl ring being unsubstituted or substituted by one, two or three groups independently selected from lower alkyl, lower alkoxy and halogen, or
- R1 and R2 together with the nitrogen atom to which they are attached form a group selected from 1-oxa-8-aza-spiro[4.5]decyl, 1,4-dioxa-8-aza-spiro[4.5]decyl and [1,4]oxazepan-7-one;
- R3 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl,
- lower hydroxyalkyl, lower alkoxyalkyl, lower halogenalkyl, lower cycloalkylalkyl,
- lower alkanoyl, lower cyanoalkyl, lower alkylsulfonyl,
- phenylsulfonyl wherein the phenyl ring may be unsubstituted or substituted with one to three groups independently selected from lower alkyl, halogen, lower alkoxy, lower halogenalkoxy and lower hydroxyalkyl,
- phenyl unsubstituted or substituted with one to three groups independently selected from lower alkyl, halogen, cyano, morpholinyl, lower alkoxy, lower alkoxycarbonyl, lower halogenalkyl, lower halogenalkoxy, lower hydroxyalkyl, lower alkylsulfonyl and lower alkylsulfonylamino, benzodioxolyl,
- lower phenylalkyl, wherein the phenyl ring may be unsubstituted or substituted with one to three groups independently selected from lower alkyl, halogen, cyano, morpholinyl, lower alkoxy, lower alkoxycarbonyl, lower halogenalkyl, lower halogenalkoxy, lower hydroxyalkyl, lower alkylsulfonyl and lower alkylsulfonylamino, and
- heteroaryl unsubstituted or substituted with one or two groups independently selected from lower alkyl, lower alkoxy, cyano, morpholinyl and halogen;
- R4, R12 and R5 are hydrogen, or
- one of R4, R12 and R5 is halogen and the other ones are hydrogen;
- G is
- wherein
- m is 1 or 2;
- R8 is hydrogen or lower heterocyclylalkyl;
- R9 is hydrogen or —NR10R11;
- R10 and R11 independently from each other are lower alkyl or together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring optionally containing a further heteroatom selected from nitrogen, oxygen or sulfur;
- R13 is hydrogen or —NR10R11;
- or a pharmaceutically acceptable salt thereof.
44 more elements
Dependencies are inferred from the claim text.