Macrolides
AssigneeNovartis AG
InventorsTheodor Fehr, Lukas Oberer, Valerie Quesniaux Ryffel, Jean-Jacques Sanglier, Walter Schuler
Life of this patent
Estimating the term…
Abstract
A novel class of macrolides in which i) positions 2 to 6 inclusive of the macrocyclic ring are provided by a piperidazinyl carboxylic acid residue; and/or ii) positions 7 to 9 inclusive of the macrocyclic ring are provided by an aromatic .alpha.-amino acid residue; and/or iii) positions 10 to 12 inclusive of the macrocyclic ring are provided by an aliphatic .alpha.-amino acid residue, preferably comprising two, or especially all three of the characteristic structural features i), ii) and iii), more especially a compound of formula IX ##STR1## is provided having immunosuppressant and antinflammatory properties and protected and ring-open forms thereof.
Claims9
A macrolide of formula VIII
- S--L--M VIII
- wherein
- S represents a 1-oxo-7-aza-spiro-{5,5}-undecan-8-one-2-yl residue;
- L represents a linker comprising a linear sequence of from 6 to 11 carbon atoms;
- and
- M represents a macrocyclic ring wherein
- positions 2 to 6 of said macrocyclic ring are provided by a substituted or unsubstituted piperidazinyl carboxylic acid residue of formula I ##STR64## wherein the assigned numbers represent the position of the atoms of the residue in the macrocyclic ring,
- positions 7 to 9 of said macrocyclic ring are provided by an aromatic .alpha.-amino acid residue wherein the carboxy moiety of the aromatic .alpha.-amino acid residue occupies the 7-position of said macrocyclic ring, and the .alpha.-amino moiety of the aromatic .alpha.-amino acid residue occupies the 9-position of said macrocyclic ring,
- positions 10 to 12 of said macrocyclic ring are provided by an aliphatic .alpha.-amino acid residue wherein the carboxy moiety of the aliphatic .alpha.-amino acid residue occupies the 10-position of said macrocyclic ring and the .alpha.-amino moiety of the aliphatic a-amino acid residue occupies the 12-position of said macrocyclic ring,
- the remainder of the macrocyclic ring comprising a hydroxy carboxylic acid residue having a chain length of 6 to 20 carbon atoms, the oxy moiety of which completes a macrocyclic lactone linkage and the carbonyl moiety of which forms an amide linkage with the .alpha.-amino group at the 12-position of the macrocyclic ring, in free or protected form, or a salt thereof.
A Sanglifehrin selected from the group consisting of Sanglifehrin A, B, C and D.
Dependencies are inferred from the claim text.