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US 7,112,580 B2Granted
3-nitrogen-6, 7-dioxygen steroids and uses related thereto
AssigneeInflazyme Pharmaceuticals Ltd.
InventorsJeffery R Raymond, Claudia E Kasserra, Yaping Shen
Life of this patent
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Abstract
A compound of the formula: and pharmaceutically acceptable salts, solvates, stereoisomers and prodrugs thereof, in isolation or in mixture, wherein R groups are as defined by the present specification. The compounds may be formulated into pharmaceutical compositions, and used in the treatment and/or prevention of various conditions, including inflammation, asthma, an allergic disease, chronic obstructive pulmonary disease, atopic dermatitis, solid tumors, AIDS, ischemia, and cardiac arrhythmias.
Claims40
A compound of the formula
- and pharmaceutically acceptable salts, solvates, and stereoisomers thereof, in isolation or in mixture, where independently at each occurrence:
- R1 and R2 are selected from hydrogen, oxygen so as to form nitro or oxime, amino, sulfur so as to form —SO3—R or —SO2—R wherein R is selected from H and organic groups having 1–30 carbons optionally containing 1–6 heteroatoms selected from nitrogen, oxygen, phosphorous, silicon and sulfur, and organic groups having 1–30 carbons optionally containing 1–6 heteroatoms selected from nitrogen, oxygen, phosphorous, silicon, and sulfur;
- R3 and R4 are selected from direct bonds to the carbon at numeral 6 and the carbon at numeral 7 respectively so as to form carbonyl groups, hydrogen, or a protecting group such that R3 and/or R4 is part of hydroxyl or carbonyl protecting group;
- numerals 1 through 17 each represent a carbon;
- the carbons at numerals 1, 2, 4, 11, 12, 15, and 16 are each independently substituted with
- (a) one of:
- ═O, ═C(R5)(R5), ═C═C(R5)(R5), —C(R5)(R5)(C(R5)(R5))n— and —(O(C(R5)(R5))nO)— wherein n ranges from 1 to about 6;
- or
- (b) two of the following, which are independently selected:
- —X, —N(R1)(R2), —R5 and —OR6;
- the carbons at numerals 5, 8, 9, 10, 13 and 14 are each independently substituted with one of —X, —R5, —N(R1)(R2) or —OR6;
- the carbon at numeral 17 is substituted with —C(R5)(R5)(C(R5)(R5))n— or —(O(C(R5)(R5))nO)— wherein n ranges from 1 to about 6;
- in addition to the —OR3 and —OR4 groups as shown, each of the carbons at numerals 6 and 7 are independently substituted with one of —X, —N(R1)(R2), —R5 or —OR6;
- each of rings A, B, C and D is independently fully saturated, partially saturated or fully unsaturated;
- R5 at each occurrence is independently selected from H, X, and C1-30 organic moiety optionally containing at least one heteroatom selected from the group consisting of boron, halogen, nitrogen, oxygen, silicon and sulfur;
- where two geminal R5 groups may together form a ring with the carbon atom to which they are both bonded;
- R6 is H or a protecting group such that —OR6 is a protected hydroxyl group, where vicinal —OR6 groups may together form a cyclic structure that protects vicinal hydroxyl groups, and where geminal —OR6 groups may together form a cyclic structure that protects a carbonyl group;
- and
- X represents fluoride, chloride, bromide and iodide.
16 more elements
Dependencies are inferred from the claim text.