Sulphonylpyrroles
Inventors
Maier, Thomas • Beckers, Thomas • Baer, Thomas • Gimmnich, Petra • Dullweber, Frank • Vennemann, Matthias
Assignees
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Publication Number
US-8067615-B2
Publication Date
2011-11-29
Expiration Date
Abstract
Compounds of a certain formula (I), in which R1, R2, R3, R4, R5, R6 and R7 have the meanings indicated in the description, are novel effective HDAC inhibitors.
Core Innovation
The invention provides N-sulphonylpyrrole derivatives as compounds of formula I, optionally as salts thereof, with variable substituents R1-R7 and defined linker and aryl/heteroaryl radical portions specified by R6 = -T1-Q1 and R7 being hydroxyl or Cyc1. The compounds are described as novel effective HDAC inhibitors.
The formula I framework specifies that T1 is a bond or 1-4C-alkylene and that Q1 is Aa1, Hh1, or Ah1. Aa1 is a bisaryl radical made up of two aryl groups independently selected from phenyl and naphthyl and linked via a single bond, Hh1 is a bisheteroaryl radical made up of two heteroaryl groups independently selected from monocyclic 5- or 6-membered heteroaryl radicals comprising one or two heteroatoms, and Ah1 is an aryl-heteroaryl radical bonded via the heteroaryl moiety.
The described substitution scope further includes biphenyl, bipyridyl, pyrazolyl-pyridinyl, imidazolyl-pyridinyl, and pyridinyl-thiophenyl examples, and specific Cyc1 ring system Ia embodiments where A and B are carbon and R71 and R72 are hydrogen, halogen, 1-4C-alkyl, or 1-4C-alkoxy. The document also provides representative (E)-N-hydroxy-acrylamide and (E)-acrylamide structures bearing sulfonyl-substituted pyrrole motifs.
Claims Coverage
The partial claim set includes two independent claim families covering a broad compound-of-formula definition and a selected set of named (E)-acrylamide N-sulphonylpyrrole exemplars, with salts also covered. Across these, the inventive features center on the defined HDAC-inhibitor scaffold and the explicitly named sulfonyl-substituted pyrrole structures.
Formula I compound with defined R1-R7, Q1, and Cyc1 or hydroxyl R7
A compound of formula I, or a salt thereof, in which R1-R5 are independently hydrogen, 1-4C-alkyl, halogen, or 1-4C-alkoxy as defined; R6 is -T1-Q1 where T1 is a bond or 1-4C-alkylene and Q1 is Aa1, Hh1, or Ah1; and R7 is hydroxyl or Cyc1 where Cyc1 is a ring system of formula Ia with the specified A/B carbon ring and R71/R72 options.
Selected (E)-acrylamide N-sulphonylpyrrole compounds and salts
A compound selected from the specified (E)-3-[1-(sulfonyl substituted 1H-pyrrol-3-yl)]-N-hydroxy-acrylamide and (E)-N-(2-Amino-phenyl)-3-[1-(sulfonyl substituted 1H-pyrrol-3-yl)]-acrylamide structures, including biphenyl-4-sulfonyl, biphenyl-3-sulfonyl, and 5-pyridin-2-yl-thiophene-2-sulfonyl variants, and the salts thereof.
Claim coverage is centered on the formula I HDAC-inhibitor scaffold with variable Q1, T1, and R7 features, together with a narrower group of explicitly named (E)-acrylamide N-hydroxy and N-(2-Amino-phenyl) sulfonylpyrrole variants, including salts.
Stated Advantages
The N-sulphonylpyrrole derivatives are described as novel effective HDAC inhibitors.
Documented Applications
No documented applications found
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