1-ALKYL-, 1-ALKENYL- AND 1-ALKYNYLARYL-2-AMINO-1,3-PROPANEDIOLS AND RELATED COMPOUNDS, A PROCESS AND INTERMEDIATES FOR THEIR PREPARATIONAND THEEIR USE AS MEDICAMENTS

• Main Authors: HAMER, RUSSELL RICHARD LEE, FREED, BRIAN SCOTT, RAUCKMAN, BARBARA SEAVEY, TEGELER, JOHN JOSEPH
• Format: Patent
• Language: English; French
• Published: 05.11.2002
• Edition: 5
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

The present invention relates to novel 1-alkyl-, 1-alkenyl- and 1-alkynylary l- 2-amino-1,3- propanediols, intermediates and processes for the preparation thereof. The compounds of the invention are of the formula I RCH(OR1)CH(NR2R3)R4 (I) wherein R is wherein R5 is CH3(CH2)mC=C. CH3(CH2)m,CH=CH, CH3(CH2)m,CH2CH2, wherein m is 3 to 15, n is 0 to 12, W and X are independently hydrogen, (C1- C8) alkyl, (C1-C8) alkoxy, halogen or trifluoromethyl, and Z is S. O, or C=O: and A is S or O: R1 is hydrogen or wherein R6 is hydrogen, (C1-C8) alkyl. (C1-C8) alkoxy. or :R2 is hy drogen (C1-C3) alkyl. R3 is hydrogen (C1-C3) alKyl or wherein R6 is as above: R4 is wherein R7 is hydrogen (C1-C8) alkyl. or CH2 OR8 wherein R8 is hydrogen or wherein R6 is as above: R1 and R8 taken together with the oxygen to which th ey are attached form a group of the formula wherein R9 and R10 are independently hydrogen or alkyl, where alkyl is a straight or branched chain hydrocarbon having no unsaturation and 1 to 10 carbon atoms, the optical isomers thereof, or the pharmaceutically acceptable salts thereof. The compounds of the invention exhibit antiinflammatory, memory dysfuncti on relieving, cell poliferation reducing, antibacterial and antifungal activity and can, therefore, be used as medicaments.