- Trans-2-acylaminocyclohexyloxyacyldipeptides in the form of mixtures of diastereoisomers thereof and in the form of pure diasteredisomers, process for the preparation thereof and pharmaceutical compositions containing the same
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There are described novel trans-2-acylaminocyclohexyloxyacyldipeptides of formula I STR1 wherein R1 represents --CO--R6, --SO2 --R7 or STR2 R6 is C1 -C18 alkyl or C1 -C18 alkoxy, R7 is C1 -C18 alkyl or an optionally substituted phenyl group, Y is =O, =S or =NH; R2 =R3 and represent --H or C1 -C12 alkyl, R4 represents --OR8 or --NHR9, R8 is --H, C1 -C8 alkyl or benzyl, R9 is --H, a straight or branched chain C1 -C18 alkyl group or benzyl group; R5 represents --OR9 or --NHR9, and novel (1R,2R)- and (1S,2S)-trans-2-acylaminocyclohexyloxyacetyldipeptides of the formulas Ia and Ib STR3 wherein R1 is --CO--R6, R6 is C1 -C18 alkyl, R2 is --H, R3 is --H or C1 -C12 alkyl, R4 is --OR8 or --NHR9, R8 is --H, C1 -C8 alkyl or benzyl, R9 is --H, C1 -C18 alkyl or benzyl, R5 is --OR9 or --NHR9 Compounds of formula I, Ia and Ib and the pharmaceutically acceptable alkali salts thereof show immunomodulatory and antitumour activities and can be used in the preparation of medicaments.
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- Preparation of diastereomerically pure immunologically active carbocyclic nor-muramyldipeptide analogues
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The preparation of diastereomerically pure immunologically active carbocyclic nor-muramyldipeptide analogues (1'R,2'R)-/(1'S,2'S)-N-[2-(2'-acetylaminocyclohexyloxy)acetyl]-L- alanyl-D-isoglutamine and (1'R,2'R)-/(1'S,2'S)-N-[2-(2'-acetylaminocyclohexyloxy)acetyl]-L- alanyl-D-glutamic acid is described. The title compounds were synthesized using two independent synthetic routes from racemic trans-2-azidocyclohexanol and (1R,2R)-/(1S,2S)-2-aminocyclohexanol, respectively.
- Kikelj,Kidric,Pristovisek,Pecar,Urleb,Krbavcic,Honig
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p. 5915 - 5932
(2007/10/02)
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- Synthesis and Functionalization of trans-2-(2'-Aminocyclohexyloxy)- and trans-2-(2'-Azidocyclohexyloxy)acetic Acid
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Synthesis of the hydrochloride of trans-2-(2'-aminocyclohexyloxy)acetic acid (4) from trans-2-(2'-azidocyclohexyloxy)acetic acid (1) is described. 4 was acylated at the amino group to give compounds 5-8. 1 was converted into acid chloride (9) and amides 1
- Kikelj, Danijel,Krbavcic, Ales,Pecar, Slavko,Tomazic, Alenka
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p. 275 - 281
(2007/10/02)
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