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US 2007/0184979 A1Published application
Novel sulfonylpyrroles
AssigneeAltana Pharma AG
InventorsThomas Maier, Thomas Beckers, Thomas Baer, Petra Gimmnich, Frank Dullweber, Matthias Vennemann
Life of this patent
Estimating the term…
Abstract
Compounds of the formula I in which the substitutents have the definitions provided in the specification, are novel, effective HDAC inhibitors.
Claims23
A compound of formula I
- in which
- R1 is hydrogen, 1-4C-alkyl, halogen, or 1-4C-alkoxy,
- R2 is hydrogen or 1-4C-alkyl,
- R3 is hydrogen or 1-4C-alkyl,
- R4 is hydrogen, 1-4C-alkyl, halogen, or 1-4C-alkoxy,
- R5 is hydrogen, 1-4C-alkyl, halogen, or 1-4C-alkoxy,
- R6 is -T1-Q1, in which
- T1 is a bond, or 1-4C-alkylene,
- Q1 is Ar1, Aa1, Hh1, or Ah1, in which
- Ar1 is phenyl, or R61- and/or R62-substituted phenyl, in which
- R61 is 1-4C-alkyl, or -T2-N(R611)R612, in which
- either
- T2 is a bond, and
- R611 is hydrogen, 1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl-1-4C-alkyl, or Har1-1-4C-alkyl, in which
- Har1 is optionally substituted by R6111 and/or R6112, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated heteroaromatic ring comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur, in which
- R6111 is halogen, or 1-4C-alkyl,
- R6112 is 1-4C-alkyl, and
- R612 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or hydroxy-2-4C-alkyl,
- or R611 and R612 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which
- Het1 is morpholino, thiomorpholino, S-oxo-thiomorpholino, S,S-dioxo-thiomorpholino, piperidino, pyrrolidino, piperazino, or 4N-(1-4C-alkyl)-piperazino,
- or
- T2 is 1-4C-alkylene, or 2-4C-alkylene interrupted by oxygen, and
- R611 is hydrogen, 1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl-1-4C-alkyl, or Har1-1-4C-alkyl, in which
- Har1 is optionally substituted by R6111 and/or R6112, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated heteroaromatic ring comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur, in which
- R6111 is halogen, or 1-4C-alkyl,
- R6112 is 1-4C-alkyl, and
- R612 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or hydroxy-2-4C-alkyl,
- or R611 and R612 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which
- Het1 is morpholino, thiomorpholino, S-oxo-thiomorpholino, S,S-dioxo-thiomorpholino, piperidino, pyrrolidino, piperazino, 4N-(1-4C-alkyl)-piperazino, imidazolo, pyrrolo or pyrazolo,
- R62 is 1-4C-alkyl, 1-4C-alkoxy, halogen, cyano, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkylcarbonylamino, or 1-4C-alkylsulphonylamino,
- Aa1 is a bisaryl radical made up of two aryl groups, which are independently selected from the group consisting of phenyl and naphthyl, and which are linked together via a single bond,
- Hh1 is a bisheteroaryl radical made up of two heteroaryl groups, which are independently selected from the group consisting of monocyclic 5- or 6-membered heteroaryl radicals comprising one or two heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur, and which are linked together via a single bond,
- Ah1 is a heteroaryl-aryl radical or an aryl-heteroaryl radical made up of a heteroaryl group selected from the group consisting of monocyclic 5- or 6-membered heteroaryl radicals comprising one or two heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur, and an aryl group selected from the group consisting of phenyl and naphthyl, whereby said heteroaryl and aryl groups are linked together via a single bond,
- R7 is hydroxyl, or Cyc1, in which
- Cyc1 is a ring system of formula Ia
- in which
- A is C (carbon),
- B is C (carbon),
- R71 is hydrogen, halogen, 1-4C-alkyl, or 1-4C-alkoxy,
- R72 is hydrogen, halogen, 1-4C-alkyl, or 1-4C-alkoxy,
- M with inclusion of A and B is either a ring Ar2 or a ring Har2, in which
- Ar2 is a benzene ring,
- Har2 is a monocyclic 5- or 6-membered unsaturated heteroaromatic ring comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur,
- or a salt thereof.
41 more elements
(canceled)
15-17. (canceled)
Dependencies are inferred from the claim text.