Chiral cyclic β-amino acids and their derivatives, pharmaceutical compositions containing them and the use of such compounds

US8183292B2 · kind B2 · utility

Assignee

• BioBlocks Magyarorszag Gyogyszerkemiai es Fejleszto Kft. · HU

Inventors

• Ferenc Fulop · Szeged, HU
• Zsolt Szakonyi · Szeged, HU

Key dates

• Filing date: Nov 14, 2007
• Grant date: May 22, 2012
• Expiry date: Jul 13, 2028

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/18
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to chiral cyclic β-amino acids of Formula (I) and their salts formed with pharmaceutically acceptable acids or bases, wherein the main meanings of the substituents are as follows: R stands for C1-4 Alk; X stands for —COOH, —CONH2, —CONH(C1-4 Alk), —CON(C1-4 Alk)2, —COO(C1-4 Alk), —COPhe-O—(C1-4 Alk) or —CH2OH; Y stands for —NH2, —NHBoc, —NHFmoc, —NH(C1-4 Alk), —N(C1-4 Alk)2, —NHCH2Ph, or Ar—NH—C(═X0)—N(R0)— wherein Ar stands for a phenyl group substituted by C1-4 alkoxy or halogen, X0 stands for O or S, and R0 stands for hydrogen or benzyl; and X+Y stands for —CONH— vagy —CON(Boc)-; with the proviso that when X stands for —COOH, then Y may be only different from —NH2. The invention also relates to pharmaceutical compositions having multidrug-resistance reversing effect that contain one or more compound(s) of Formula (I) or a salt thereof and inert pharmaceutical carriers and/or auxiliary agents. The invention also relates to carboxylic acids of Formula (XX) and their salts.