Immunosuppressive macrocyclic compounds

Details Immunosuppressive macrocyclic compounds Immunosuppressive macrocyclic compounds

1992-09-11

1994-03-22

Bond, Robert T.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514411, 540456, C07D49818, A61K 31395

Patent

active

052964892

DESCRIPTION:

BRIEF SUMMARY
This invention relates to immunosuppressive macrocyclic compounds, processes for their preparation, their use as medicaments, and compositions containing them.
European Patent Application 184162 (to Fujisawa Pharmaceuticals Co Ltd) discloses a number of macrocyclic compounds isolated from microorganisms belonging to the genus Streptomyces. The macrolides are numbered FR-900506, FR-900520, FR-900523 and FR-900525, and the preparation of some of their derivatives is also described.
International Patent Applications Nos WO 89/05304 and PCT/GB90/01262 and European Patent Application No 413532 (to Fisons plc), European Patent Application 353678 (to Fujisawa Pharmaceuticals CO Ltd), European Patent Applications 349049, 349061, 358508 and 388153 (to Merck & CO Inc) and European Patent Application 356399 and International Patent Application WO 90/15805 (to Sandoz AG) also disclose a number of immunosuppressive macrocyclic compounds.
We have now found a new group of immunosuppressive macrocyclic compounds which possess advantageous properties over those disclosed previously.
According to the present invention, there is provided a compound of formula I, ##STR1## wherein R.sup.1 represents H, OH or alkoxy; between the carbon atoms to which they are attached; NHCO-alkyl; ##STR2## in which R.sup.5 represents (H,H), (H,OH), (H,methoxy) or O; R.sup.6 represents H, (R)--OH, (S)--OH, alkoxy, amino, alkylazino, alkanoylamino, formyloxy or halogen; R.sup.7 represents H; and in addition R.sup.5 and R.sup.6 may together represent a second bond between the carbon atoms to which they are attached; or R.sup.6 and R.sup.7 may together represent a second bond between the carbon atoms to which they are attached; ##STR3## in which R.sup.8 represents alkyl substituted by one or more groups selected from OH, alkoxy, .dbd.O, and CO.sub.2 H; or alkenyl optionally substituted by one or more groups selected from OH, .dbd.O, or CO.sub.2 H; provided that R.sup.4 represents OH; R.sup.5 represents (H,mothoxy); and R.sup.6 represents (R)--OH; then X does not represent O; propyl; R.sup.4 represents OH; R.sup.5 represents (H,methoxy); and R.sup.6 represents (R)--OH; then X does not represent O; carbon atoms to which they are attached or each represent H; R.sup.3 represents allyl or propyl; R.sup.4 represents OH; R.sup.5 represents (H,methoxy); and R.sup.6 represents (R)--OH; then X does not represent O; represents a second bond between the carbon atoms to which they are attached; R.sup.3 represents allyl; R.sup.4 represents OH; R.sup.5 represents (H,methoxy); and R.sup.6 represents methoxy; then X does not represent O; represents OH; R.sup.5 represents (H,methoxy); and R.sup.6 represents (R)--OH; then X does not represent (H,OH); OH; R.sup.5 represents (H,OH); and R.sup.6 represents (R)--OH; then X does not represent O; represents OH; R.sup.5 represents (H,methoxy); and R.sup.6 represents (R)--OH; then X does not represent (H,OH); carbon atoms to which they are attached or each represent H; R.sup.3 represents ethyl; R.sup.4 represents OH; R.sup.5 represents (H,methoxy); and R.sup.6 represents (R)--OH; then X does not represent O; represents OH; R.sup.5 represents (H,OH) or (H,methoxy); and R.sup.6 represents (R)--OH; then X does not represent (H,H); represents OH; R.sup.5 represents (H,methoxy); and R.sup.6 represents (R)--OH; then X does not represent (H,H); R.sup.4 represents OH; R.sup.5 represents (H,OH); and R.sup.6 represents (R)--OH; then X does not represent O; and represents OH; R.sup.5 represents O; and R.sup.6 represents (R)--OH; then X does not represent O;
Pharmaceutically acceptable derivatives which may be mentioned include esters, amides and salts of any carboxylic acid groups which may be present. The esters and amides preferably contain up to 6 carbon atoms. Salts include alkali metal and alkaline earth metal salts, for example sodium or calcium.
When any one of R.sup.1, R.sup.4, R.sup.5, R.sup.6, and R.sup.8 represent carbon-containing groups, we prefer those groups to contain up to 10 carbon atoms, more preferably up to 6 carbo

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