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US 2014/0194505 A1Published application
Neuraminidase Inhibitors
AssigneeSineVir Therapeutics LLC
InventorsJohn Hilfinger, Wei Shen
Life of this patent
Estimating the term…
Abstract
Disclosed are neuraminidase inhibitor compounds and pharmaceutical compositions with improved bioavailability and/or improved efficacy and methods of treating influenza using the compounds and pharmaceuticals compositions.
Claims20
A compound of formula (I):
- wherein:
- L1 is —(CRoRo)mC(R4)2(CRoRo)nO(CRoRo)o—;
- R1 is —C(O)(CRoRo)rC(RoR′)(CRoRo)sNH2, —C(O)(CRoRo)rC(RoR′)(CRoRo)sN(H)C(O)(CRoRo)wC(RoR″)(CRoRo)x—NH2, or —C(O)(CRoRo)C(RoR′)(CRoRo)sN(H)C(O)(CRoRo)wC(RoR″)(CRoRo)xN(H)C(O)(CRoRo)yC(RoR″′)(CRoRo)zNH2;
- each occurrence of m, n, o, r, s, w, x, y, or z is independently zero, one, or two;
- each occurrence of Ro is independently H, optionally substituted alkyl, optionally, substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
- R2 is NH2 or —NHC(NH2)NH;
- R3 is H, —OR*, or —CHR*R**;
- R′, R″ and R′″ are each independently an amino acid side chain;
- each occurrence of R4 is independently hydrogen or an optionally substituted group selected from a C1-C6 alkyl group, a 3-7 membered saturated, partially saturated or fully unsaturated monocyclic ring having 0-3 heteroatoms independently selected from nitrogen or oxygen or two occurrences of R4 are taken together with the atom(s) to which they are bound to form an optionally substituted 3-7 membered ring, wherein if one occurrence of R4 is H, then the other occurrence of R4 is not H or —CH3;
- R* and R** are independently, H, OH, —OR5, or optionally substituted C1-C12 alkyl;
- R5 is optionally substituted C1-C6 alkyl, or —C(O)NRoRo;
- X1 is O or CH wherein if X1 is O, then there is a single bond between X1 and X2 and a double bond between X2 and X3;
- and wherein X1 is CH then there is a double bond between X1 and X2 and a single bond between X2 and X3;
- X2 is C;
- and
- X3 is CH or CH2;
- or a pharmaceutically acceptable salt thereof.
14 more elements
A compound which is:
A compound of formula (IV):
- wherein:
- L1 is —(CRoRo)mC(R4)2(CRoRo)nO(CRoRo)o—;
- R1 is —C(O)(CRoRo)rC(RoR′)(CRoRo)sNH2, —C(O)(CRoRo)rC(RoR′)(CRoRo)sN(H)C(O)(CRoRo)wC(RoR″)(CRoRo)xNH2, or —C(O)(CRoRo)rC(RoR′)(CRoRo)sN(H)C(O)(CRoRo)wC(RoR″)(CRoRo)xN(H)C(O)(CRoRo)yC(RoR″′)(CRoRo)zNH2;
- each occurrence of m, n, o, r, s, w, x, y, or z is independently zero, one, or two;
- each occurrence of Ro is independently alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl;
- each occurrence of R4 is independently hydrogen or an optionally substituted group selected from a C1-C6 alkyl group, a 3-7 membered saturated, partially saturated or fully unsaturated monocyclic ring having 0-3 heteroatoms independently selected from nitrogen or oxygen or two occurrences of R4 are taken together with the atom(s) to which they are bound to form an optionally substituted 3-7 membered ring, wherein if one occurrence of R4 is H, then the other occurrence of R4 is not H or CH3;
- R5 is optionally substituted C1-C4 alkyl, —C(O)NRoRo;
- R6 is C1-C10 alkyl;
- and
- R7 is —OH, —OR5, C1-C6 alkyl or —NRoRo;
- or a pharmaceutically acceptable salt thereof.
8 more elements
Dependencies are inferred from the claim text.