Preparation of N-substituted 2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoyl amides

US7132569B2 · kind B2 · utility

Assignee

• Speedel Pharma AG · CH

Inventors

• Peter Herold · Allschwil, CH
• Stefan Stutz · Basel, CH
• Adriano Indolese · Möhlin, CH

Key dates

• Filing date: Oct 21, 2005
• Grant date: Nov 7, 2006
• Expiry date: Oct 21, 2025

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D263/22
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

From compounds of formula IIwherein R1 and R2 are independently of one another H, C1–C6alkyl, C1–C6halogenalkyl, C1–C6alkoxy, C1–C6alkoxy-C1–C6alkyl, or C1–C6alkoxy-C1–C6alkyloxy, R3 is C1–C6alkyl, R4 is C1–C6alkyl, and R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6-alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6-alkyl, C1–C6-dialkylamino-C1–C6-alkyl, C1–C6-alkanoylamido-C1–C6-alkyl, HO(O)C—C1–C6-alkyl, C1–C6alkyl-O—(O)C—C1–C6alkyl, H2N—C(O)—C1–C6alkyl, C1–C6alkyl-HN—C(O)—C1–C6alkyl or (C1–C6alkyl)2N—C(O)—C1–C6-alkyl, R6 is C1–C6alkyl, R7 is C1–C6alkyl or C1–C6alkoxy, or R6 and R7 together are tetramethylene, pentamethylene, 3-oxa-1,5-pentylene or —CH2CH2O— substituted, if necessary, with C1–C4-Alkyl, phenyl or benzyl, it is possible—through halolactonization, azidation of the halogen group, ring opening with an amine R5—NH2, and reduction of the azide group to form the amino group—to prepare compounds of formula Iwherein R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6alkyl, C1–C6dialkylamino-C1–C6-alkyl, C1–C6alkanoylamido-C1–C6alkyl, HO(O)C—C1–C6alkyl, C1–C6alkyl-O—…