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US 7,078,399 B2Granted
Sulfhydryl rifamycins and uses thereof
AssigneeActivBiotics, Inc.
InventorsArthur F. Michaelis, Hawkins V. Maulding, Chalom Sayada, Barry Eisenstein, William B. Geiss, Joseph Raker
Life of this patent
Estimating the term…
Abstract
The invention features sulfhydryl rifamycin compositions, methods of making these compositions, and methods for treating disease using these compositions.
Claims15
A compound of formula I:
- wherein
- X1 represents an oxygen atom or a sulfur atom;
- R1 represents a hydrogen or an acetyl group;
- R2 represents a hydrogen or hydroxyl group;
- and
- R3 represents a hydrogen atom or a group expressed by the formula:
- wherein each of R4 and R5 is, independently, an alkyl group having 1 to 7 carbon atoms, or R4 and R5 combine to form a 3–8 membered cyclic system,
- or R3 represents a group expressed by the formula:
- in which g represents an integer between 1 and 3;
- or R3 represents a group expressed by the formula:
- wherein each of R6 and R7 is, independently, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, X2 represents an oxygen atom, a sulfur atom, a carbonyl group,
- or X2 represents a group expressed by the formula:
- in which each of R8 and R9 is, independently, a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms, or R8 and R9, in combination with each other, represent —(CH2)k— in which k represents an integer between 1 and 4;
- or X2 represents a group expressed by the formula:
- in which m represents 0 or 1, R10 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or —(CH2)nX3 in which n represents an integer between 1 and 4, and X3 represents an alkoxy group having 1 to 3 carbon atoms, a vinyl group, an ethynyl group,
- or X2 represents a group expressed by the formula:
13 more elements
A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and one or more compounds of formula I:
- wherein
- X1 represents an oxygen atom or a sulfur atom;
- R1 represents a hydrogen or an acetyl group;
- R2 represents a hydrogen or hydroxyl group;
- and
- R3 represents a hydrogen atom or a group expressed by the formula:
- wherein each of R4 and R5 is, independently, an alkyl group having 1 to 7 carbon atoms, or R4 and R5 combine to form a 3–8 membered cyclic system,
- or R3 represents a group expressed by the formula:
- in which g represents an integer between 1 and 3;
- or R3 represents a group expressed by the formula:
- wherein each of R6 and R7 is, independently, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, X2 represents an oxygen atom, a sulfur atom, a carbonyl group,
- or X2 represents a group expressed by the formula:
- in which each of R8 and R9 is, independently, a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms, or R8 and R9, in combination with each other, represent —(CH2)k— in which k represents an integer between 1 and 4;
- or X2 represents a group expressed by the formula:
- in which m represents 0 or 1, R10 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or —(CH2)nX3 in which n represents an integer between 1 and 4, and X3 represents an alkoxy group having 1 to 3 carbon atoms, a vinyl group, an ethynyl group,
- or X2 represents a group expressed by the formula:
- or formula II:
- wherein
- R1 is hydrogen or an acetyl group;
- R2 is hydrogen or a hydroxyl group;
- and
- R10 is selected from the group consisting of methyl, ethyl, iso-propyl, n-propyl, iso-butyl, (S)-sec-butyl, and (R)-sec-butyl.
19 more elements
A method of synthesizing a sulfhydryl rifamycin compound of formula VII,
- wherein
- X1 represents an oxygen atom or a sulfur atom;
- R1 represents a hydrogen or an acetyl group;
- R2 represents a hydrogen or hydroxyl group;
- and
- P1 represents a sulfhydryl protecting group,
- said method comprising reacting rifamycin S with a compound of formula VIII
- wherein
- Z1 represents a hydroxyl or sulfhydryl group;
- and
- P1 represents a sulfhydryl protecting group.
8 more elements
Dependencies are inferred from the claim text.