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US 7,030,130 B2Granted
Benzofuran derivatives and their use as antibacterial agents
AssigneeArpida AG
InventorsKaspar Burri, Dieter Gillessen, Sorana Greiveldinger-Poenaru, Khalid Islam
Life of this patent
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Abstract
The invention relates to novel benzofuran derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as anti-infectives.
Claims16
A compound of formula
- wherein R1 represents cycloalkylmethyl with 3 to 6 carbon atoms;
- aryl;
- arylmethyl or heteroarymethyl, the aryl and heteroaryl group may be mono-, di- or tri-substituted with halogen, amino, hydroxy, nitro, trifluoromethyl, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different;
- straight or branched chain lower alkylcarbonyl with up to 6 carbon atoms;
- cycloalkylcarbonyl with 3 to 6 carbon atoms;
- cycloalkylhydroxymethyl with 3 to 6 carbon atoms;
- arylcarbonyl, the aryl group may be mono-, di or tri-substituted with halogen, amino, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different;
- arylhydroxymethyl, the aryl group may be mono-, di- or tri-substituted with halogen, amino, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different;
- straight or branched chain lower alkenyl with 2 to 6 carbon atoms;
- hydroxy-lower alkyl with 1 to 6 carbon atoms;
- fluoro-lower alkyl with 1 to 6 carbon atoms;
- aryloxy-lower alkyl whereby the aryl group may be mono-, di- or tri-substituted with halogen, amino, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different;
- arylthio-lower alkyl whereby the aryl group may be mono-, di- or tri-substituted with halogen, amino, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different;
- arylamino-lower alkyl whereby the aryl group may be mono-, di- or tri-substituted with halogen, amino, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different;
- lower alkenyloxy lower alkyl whereby the lower alkenyl group may contain 2 to 4 carbon atoms and the lower alkyl group may contain 1 or 2 carbon atoms;
- benzyloxy lower alkyl whereby the benzyl group may be mono-, di- or tri-substituted with halogen, amino, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different;
- lower alkylamino lower alkyl whereby the lower alkyl groups may contain 1 to 3 carbon atoms;
- heterocyclylmethyl containing one to three hetero atoms which can be the same or different and which may be substituted with lower alkyl, halogen, amino, lower alkyloxy, hydroxy, lower alkylcarbonylamino, arylcarbonylamino and benzofused derivatives thereof, and wherein R2 and R3 independently represent hydrogen;
- lower alkyl with 1 to 3 carbon atoms;
- or together a lower alkylene group with 1 to 3 carbon atoms bridging the oxygen atoms and forming a five, six or seven membered ring;
- R4 represents hydrogen;
- straight or branched chain lower alkyl with 1 to 4 carbon atoms;
- a pharmaceutically acceptable salt thereof;
- or N-oxide thereof.
21 more elements
The compound of formula
- wherein R1 is cycloalkylmethyl with 3 to 6 carbon atoms;
- aryl;
- arylmethyl or heteroarymethyl, the aryl and heteroaryl group may be mono- or di substituted with halogen, amino, hydroxy, nitro, trifluoromethyl, lower alkyloxy, lower alkylcarbonylamino, arylcarbonylamino, whereby these substituents may be the same or different, and R2 and R3 are methyl or together are a methylene group bridging the oxygen atoms to which they are attached and R4 is hydrogen or methyl.
The compound of formula
- wherein R1 is 4-methoxy-benzyl, phenyl, benzyl, cyclopropylmethyl, 4-fluoro-benzyl, 3,4-dihydro-1 H-isoquinolin-2-ylmethyl, 4-methoxy-benzyloxymethyl, 4-acetylaminophenyl-sulfanyl-methyl, 4-trifluoromethyl-phenoxymethyl, 4-amino-phenoxymethyl, allyloxymethyl, phenyl-[1,3]dioxolan-2-yl, pyrrol-1-ylmethyl, 3,4-dimethoxy-benzyl, 4-hydroxyphenyloxylnethyl, phenylcarbonylmethyl, 4-fluoro-phenoxymethyl, 2,2-dimethyl-propyl, 4-fluoro-phenylsulfanylmethyl, hydroxymethyl, formyl, 4-fluoro-phenylamino-methyl, imidazol-1 -ylmethyl, dimethylaminomethyl, morpholin-4-ylmethyl, biphenyl-4-ylmethyl, ethoxycarbonyl, carboxy, 4-hydroxybenzyl, furan-2-ylmethyl, thiophen-2-ylmethyl, thiophen-3 -ylmethyl, 1-methyl-pyrrol-2-ylmethyl, pyridin-2-ylmethyl, pyridin-3-ylmethyl, pyridin-4-ylmethyl, 4-acetylaminobenzyl, 4-amino-benzyl, 4-nitro-benzyl, 4-acetylamino-3-methoxy-benzyl, 4-amino-3-methoxy-benzyl, 3-acetylamino-4-methoxy-benzyl, 3-amino-4-methoxy-benzyl, allyl, isopropenyl or halogenmethyl, and R2 and R3 are methyl or together are a methylen group bridging the oxygen atoms to which they are attached and R4 is hydrogen or methyl.
The compound of formula
- wherein R1 is 4-methoxy-benzyl, phenyl, benzyl, cyclopropylmethyl, 4-fluoro-benzyl, 3,4-dihydro-1 H-isoquinolin-2-ylmethyl, 4-methoxy-benzyloxymethyl, 4-acetylaminophenyl-sulfanyl-methyl, 4-trifluoromethyl-phenoxymethyl, 4-amino-phenoxymethyl, allyloxymethyl, 3,4-dimethoxy-benzyl, 4-hydroxybenzyl, pyridin-2-ylmethyl, pyridin-3 -ylmethyl, pyridin-4-ylmethyl, 4-acetylaminobenzyl, 4-amino-benzyl, 4-acetylamino-3 -methoxy-benzyl, 4-amino-3-methoxy-benzyl, 3-acetylamino-4-methoxy-benzyl, 3-amino-4-methoxy-benzyl or aryl methyl and R2and R3 are both methyl and R4 is hydrogen.
The compound of formula
- wherein R1 is 4-methoxy-benzyl, benzyl, cyclopropylmethyl, 4-fluoro-benzyl, 3,4-dihydro-1 H-isoquinolin-2-ylmethyl, 4-amino-phenoxymethyl, 4-hydroxybenzyl, pyridin-2-ylmethyl, pyridin-3-ylmethyl, pyridin-4-ylmethyl, 4-acetylaminobenzyl, 4-amino-benzyl, 4-acetylamino-3-methoxy-benzyl, 4-amino-3-methoxy-benzyl, 3-acetylamino-4-methoxy-benzyl, 3-amino-4-methoxy-benzyl and R2 and R3 are both methyl and R4 is hydrogen.
Dependencies are inferred from the claim text.