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US 6,660,764 B2Granted
Carboxylic acid amides, pharmaceutical compositions containing these compounds, their use and the preparation thereof
AssigneeBoehringer Ingelheim Pharma GmbH & Co. KG
InventorsNorbert Hauel, Henning Priepke, Klaus Damm, Andreas Schnapp
Life of this patent
Estimating the term…
Abstract
The present application relates to new carboxylic acid amides of general formula wherein A, B and R1 to R3 are defined as in claim 1, processes for preparing them, pharmaceutical compositions containing these compounds and the use thereof and their preparation.
Claims10
A carboxylic acid amide of formula I
- wherein
- R1 is a hydrogen atom or a C1-3-alkyl group,
- R2 is a hydrogen, fluorine, chlorine or bromine atom or a C1-3-alkyl group,
- R3 is a hydrogen atom or a C1-5-alkyl group,
- A is a bicyclic heteroaryl group consisting of
- a 5-membered heteroaryl group optionally substituted in the carbon skeleton by a fluorine, chlorine or bromine atom or by a C1-3-alkyl or C1-3-alkoxy group, wherein the 5-membered heteroaryl group contains an oxygen or sulphur atom, and
- a phenyl ring fused to the abovementioned monocyclic heteroaryl groups via two adjacent carbon atoms, by means of which the bicyclic heteroaryl group is linked to the R1-substituted alkene-carbon atom and which may also be substituted in the carbon skeleton by a fluorine, chlorine or bromine atom or by a C1-3-alkyl or C1-3-alkoxy group,
- and B is a phenyl or naphthyl group which is substituted in each case by a carboxy group, by a group which may be converted into a carboxy group in viva or by a group which is negatively charged under physiological conditions, while the abovementioned phenyl group may additionally be substituted
- by a fluorine, chlorine, bromine or iodine atom,
- by a C1-3-alkyl, trifluoromethyl, phenyl, hydroxy, C1-3-alkyl-sulphonyloxy, phenylsulphonyloxy, carboxy, C1-3-alkoxycarbonyl, formyl, C1-3-alkylcarbonyl, C1-3-alkylsulphonyl, phenylsulphonyl nitro, pyrrolidino, piperidino, morpholino, N—(C1-3-alkyl)-piperazino, aminosulphonyl, C1-3-alkylaminosulphonyl- or di-(C1-3-aminosulphonyl group,
- by an n-C2-3-alkoxy group substituted in the 2 or 3 position by a di-(C1-3-alkyl)-amino group,
- by an amino group, by an N—(C1-3-alkyl)-amino or N, N-di-(C1-3-alkyl)-amino group wherein the alkyl moiety in the 2 or 3 position relative to the nitrogen atom may be substituted in each case by a C1-3-alkoxy group, by an N-phenylamino, N-(phenyl-C1-3-alkyl)-amino or N-(pyridyl-C1-3-alkyl)-amino group,
- by an aminocarbonyl group which may be mono- or disubstituted at the amino-nitrogen atom be a C1-3-alkyl group,
- by a pyrrolidinocarbonyl piperidinocarbonyl morpholinocarbonyl or N—(C1-3-alkyl)-piperazinocarbonyl group,
- by a sulphonyl group substituted by an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, pyrrolidino, piperidino, morpholino or N—(C1-3-alkyl)-piperazino group,
- by an amino or N—(C1-3-alkyl)-amino group which is substituted in each case at the amino-nitrogen atom by an aminocarbonyl, C1-3-alkylaminocarbonyl, phenyl-C1-3-alkylaminocarbonyl, phenylaminocarbonyl, pyridylaminocarbonyl, pyrrolidinocarbonyl, piperidinocarbonyl, morpholinocarbonyl or N—(C1-3-alkyl)-piperazinocarbonyl group, whilst in the abovementioned aminocarbonyl groups any hydrogen atom present may additionally be replaced by a C1-3-alkyl group,
- or by a 5- or 6-membered heteroaryl group,
- whilst the abovementioned phenyl groups may additionally be substituted by another fluorine, chlorine or bromine atom or by another C1-3-alkyl or C1-3-alkoxy group and two C1-3-alkoxy groups in the o position may be replaced by a methylenedioxy group,
- and the abovementioned 6-membered heteroaryl groups contain one, two or three nitrogen atoms and, unless stated otherwise, the abovementioned 5-membered heteroaryl groups contain an imino group optionally substituted by a C1-3-alkyl group, an oxygen or sulphur atom, or an imino group optionally substituted by a C1-3-alkyl group and an oxygen or sulphur atom or one or two nitrogen atoms,
- an isomer thereof or a salt thereof.
17 more elements
Dependencies are inferred from the claim text.