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US 4,056,616 AGranted
Rosamicin derivatives and method of using same
AssigneeSchering Corporation
InventorsHans Reimann, Robert S. Jaret, Mohammad Mehdi Nafissi-Varchei
Life of this patent
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Abstract
Rosamicin is an antibiotic elaborated by Micromonospora rosaria. The compounds described herein are antibacterial derivatives of rosamicin. Also described are processes for the preparation of these antibacterial derivatives from rosamicin.
Claims51
A compound of the formulae:
- ##STR7## and the non-toxic pharmaceutically acceptable acid addition salts thereof wherein the dotted lines represent facultative double bonds;
- Q is a member selected from the group consisting of O, and ##STR8## Z is a member selected from the group consisting of O, ##STR9## NOR' and NOR";
- R and R' are members selected from the group consisting of hydrogen and hydrocarbon carbonyl having 2 to 18 carbon atoms;
- R" is hydrogen or alkyl having 1 to 5 carbon atoms;
- B together with the carbon atoms of positions 12 and 13 to which it is attached represents a single bond or a double bond or, when Q or Z is other than O, or when the macrolide ring is saturated between positions 10 and 11 or unsaturated between positions 2 and 3, B may also be an oxirane ring;
- and W is a member selected from the group consisting of OR' and hydrogen, R' being as previously defined with the proviso that when W is hydrogen, positions 2 and 3 are connected by a double bond, and the further proviso that in formula II, when B, together with the carbon atoms to which it is attached represents a double bond, W is OR', Q is O, and positions 10 and 11 are connected by a double bond, Z is other than ##STR10##
3 more elements
A method of eliciting an antibacterial response which comprises administering to a warm-blooded animal having a bacterial infection a therapeutically effective quantity of a compound of the formulae:
- ##STR30## the non-toxic pharmaceutically acceptable acid addition salts thereof wherein the dotted lines represent facultative double bonds;
- Q is a member selected from the group consisting of O, and ##STR31## Z is a member selected from the group consisting of O, ##STR32## NOR' and NOR";
- R and R' are members selected from the group consisting of hydrogen and hydrocarbon carbonyl having 2 to 18 carbon atoms;
- R" is hydrogen or alkyl having 1 to 5 carbon atoms;
- B together wtih the carbon atoms of positions 12 and 13 to which it is attached represents a single bond or a double bond or, when Q or Z is other than O, or when the macrolide ring is saturated between positions 10 and 11 or unsaturated between positions 2 and 3, B may also be an oxirane ring;
- and W is a member selected from the group consisting of OR' and hydrogen, R' being as previously defined with the proviso that when W is hydrogen, positions 2 and 3 are connected by a double bond, and the further proviso that in formula II, when B, together with the carbon atoms which it is attached represents a double bond, W is OR', Q is O, and positions 10 and 11 are connected by a double bond, Z is other than ##STR33##
3 more elements
Dependencies are inferred from the claim text.