2. Academic Validation
  3. Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity

Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity

  • J Med Chem. 2003 Jan 30;46(3):399-408. doi: 10.1021/jm020067s.
David L Musso 1,  Felicia R Cochran,  James L Kelley,  Ed W McLean,  Jeffrey L Selph,  Greg C Rigdon,  G Faye Orr,  Ronda G Davis,  Barrett R Cooper,  Virgil L Styles,  James B Thompson,  William R Hall
Affiliations

Affiliation

  • 1 GlaxoSmithKline Research and Development, Five Moore Drive, Research Triangle Park, North Carolina 27709, USA. [email protected]
PMID: 12540239 DOI: 10.1021/jm020067s
Abstract

The design of rigid cyclic analogues derived from cinnamamide 1, (E)-N-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide, and beta-methylcinnamamide 2, (E)-N-cyclopropyl-3-(3-fluorophenyl)but-2-enamide, has led to the discovery of the potent, centrally acting muscle relaxant (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 17. Compound 17 also possesses potent antiinflammatory and analgesic activity. This paper describes the synthesis and the muscle relaxant, antiinflammatory, and analgesic structure-activity relationships of 17 and 67 of its analogues. Compound 17 has been taken into phase I clinical trials.

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