N-(indol-3-ylalkyl)-(hetero)arylamid Derivatives As Modulators Of Ep2 Receptors

  • Published: Feb 3, 2010
  • Earliest Priority: Jul 30 2008
  • Family: 3
  • Cited Works: 43
  • Cited by: 7
  • Cites: 45
  • Additional Info: Cited Works Published
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Abstract

N-(Indol-3-ylalkyl)-(hetero)arylamide derivatives (I) and their isomers, diasteromers, enantiomers, salts and/or cyclodextrin clathrates, are new, where (I) excludes e.g. 4-chloro-1,3-dimethyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-1H-pyrazol-5-carboxylic acid amide, N-[2-(2-methyl-1H-indol-3-yl)ethyl]-6-quinoxaline-carboxylic acid amide, 3,5-dimethyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-4-isoxazolcarboxylic acid amide, 5,7-dimethyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-pyrazolo[1,5-a]pyrimidin-2-carboxylic acid amide, and N-[2-(2-methyl-1H-indol-3-yl)ethyl]-2-methylbenzamide. N-(Indol-3-ylalkyl)-(hetero)arylamide derivatives of formula (I) and their isomers, diasteromers, enantiomers, salts and/or cyclodextrin clathrates, are new, where (I) excludes 53 amides compounds e.g. 4-chloro-1,3-dimethyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-1H-pyrazol-5-carboxylic acid amide, N-[2-(2-methyl-1H-indol-3-yl)ethyl]-6-quinoxaline-carboxylic acid amide, 3,5-dimethyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-4-isoxazolcarboxylic acid amide, 5,7-dimethyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-pyrazolo[1,5-a]pyrimidin-2-carboxylic acid amide, N-[2-(2-methyl-1H-indol-3-yl)ethyl]-2-methylbenzamide, N-[2-(2-methyl-1H-indol-3-yl)ethyl]-2-(difluoromethyl)benzamide, 3-iodo-1-methyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-1H-pyrol-2-carboxylic acid amide, 1-methyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-4-(trifluoromethyl)-1H-pyrol-3-carboxylic acid amide, 2-iodo-N-[2-(2-methyl-1H-indol-3-yl) ethyl]-3-thiophene carboxylic acid amide, and 3-(difluoromethyl)-1-methyl-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-1H-pyrazol-4-carboxylic acid amide. A : 6-12C-aryl or 5-12C-heteroaryl (optionally substituted); R 1>optionally substituted 1-6C-alkyl; R 2>1-4C-alkoxy or 1-6C-alkyl (optionally substituted), H, halo, CN or -S(O) q-CH 3; R 3>H, 1-6C-alkyl, CN, Cl or Br; q : 0-2; Y 1>-(CH 2) n; and n : 1-3. Full Definitions are given in the DEFINITIONS (Full Definitions) Field. Independent claims are included for: (1) a medicament comprising (I) in combination with a cyclooxygenase inhibitor, preferably aspirin, naproxen, indomethacin, meloxicam, celecoxib, ibuprofen, parecoxib, rofecoxib, valdecoxib, NS-398, lumiracoxib, ceracoxib or etoricoxib; and (2) the preparation of (I). [Image] ACTIVITY : Antiinfertility; Gynecological; Analgesic; Osteopathic; Cytostatic; Neuroprotective; Nootropic; Antiparkinsonian; Antiinflammatory; Gastrointestinal-Gen.; Antiulcer; Nephrotropic; Antiarteriosclerotic; Respiratory-Gen.; Antimicrobial; Contraceptive; Antiparasitic; Virucide; Hepatotropic; Anti-HIV; Immunomodulator; Cardiovascular-Gen.; Vasotropic; Ophthalmological; Angiogenesis Modulator. MECHANISM OF ACTION : Prostaglandin E2 receptor modulator. The prostaglandin E2 receptor antagonistic activity of (I) was tested in human prostaglandin E2 receptor signals. The results showed that 5-fluoro-1H-indol-2-carboxylic acid-[2-(7-chloro-2-methyl-1H-indol-3-yl)-ethyl]-amide exhibited an IC 50value of 0.047 mu M.


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