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US 9,284,297 B2Granted
Halofuginone analogs for inhibition of tRNA synthetases and uses thereof
AssigneesPresident and Fellows of Harvard College, Children's Medical Center Corporation
InventorsTracy Keller, Ralph Mazitschek, Malcolm Whitman, Jinbo Lee, Mark S. Sundrud, Anjana Rao
Life of this patent
Estimating the term…
Abstract
The present invention provides novel analogs and derivatives of halofuginone. The invention also provides pharmaceutical and cosmetic compositions thereof and methods for using halofuginone analogs in treating chronic inflammatory diseases, autoimmune diseases, dry eye syndrome, fibrosis, scar formation, angiogenesis, viral infections, ischemic damage, transplant and implant rejection, neurodegenerative diseases, and cosmetic applications.
Claims29
A compound of formula (I):
- wherein
- j is an integer between 0 and 10, inclusive;
- p is an integer between 0 and 6, inclusive;
- q is an integer between 0 and 6, inclusive;
- m is 1 or 2;
- v is an integer between 1 and 3, inclusive;
- X is N or CRX, wherein RX is hydrogen;
- halogen;
- substituted or unsubstituted aliphatic;
- substituted or unsubstituted heteroaliphatic;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORF;
- —SRF;
- —N(RF)2;
- and —C(RF)3;
- wherein each occurrence of RF is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- each occurrence of Y is independently S, O, N, NRY, C or CRY, wherein each occurrence of RY is independently hydrogen;
- halogen;
- substituted or unsubstituted heteroaryl;
- —ORG;
- —C(═O)RG;
- —CO2RG;
- —C(═O)N(RG)2;
- —CN;
- —SCN;
- —SRG;
- —SORG;
- —SO2RG;
- —NO2;
- —N(RG)2;
- or —NHC(O)RG;
- wherein each occurrence of RG is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety, wherein one, two, or three occurrences of Y are CH;
- each occurrence of T and G is independently —S—, —O—, —NRE—, or —C(RE)2—, wherein each occurrence of RE is independently hydrogen;
- halogen;
- substituted or unsubstituted aliphatic;
- substituted or unsubstituted heteroaliphatic;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORG;
- —SRG;
- —N(RG)2;
- and —C(RG)3;
- wherein each occurrence of RG is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- R1 is hydrogen;
- a protecting group;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —C(═O)RA;
- —C(═O)ORA;
- —C(═O)N(RA)2;
- or —C(RA)3;
- wherein each occurrence of RA is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- each occurrence of R2 is independently hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORB;
- —C(═O)RB;
- —CO2RB;
- —C(═O)N(RB)2;
- —CN;
- —SCN;
- —SRB;
- —SORB;
- —SO2RB;
- —NO2;
- —N(RB)2;
- —NHC(O)RB;
- or —C(RB)3;
- wherein each occurrence of RB is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- R3 is halogen;
- —OH;
- or —CO2RC;
- wherein each occurrence of RC is independently a hydrogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- or a heteroaryl moiety;
- R4 and R5 are independently hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORD;
- —C(═O)RD;
- —CO2RD;
- —C(═O)N(RD)2;
- —CN;
- —SCN;
- —SRD;
- —SORD;
- —SO2RD;
- —NO2;
- —N(RD)2;
- —NHC(O)RD;
- or —C(RD)3;
- wherein each occurrence of RD is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- and
- R6 is hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORK;
- —C(═O)RK;
- —CO2RK;
- —C(═O)N(RK)2;
- —CN;
- —SCN;
- —SRK;
- —SORK;
- —SO2RK;
- —NO2;
- —N(RK)2;
- —NHC(O)RK;
- or —C(RK)3;
- wherein each occurrence of RK is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- and pharmaceutically acceptable salts thereof.
239 more elements
A compound of formula (VI):
- wherein
- j is an integer between 1 and 8, inclusive;
- each occurrence of Y is S, O, N, or CRY, wherein each occurrence of RY is independently halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORG;
- —C(═O)RG;
- —CO2RG;
- —C(═O)N(RG)2;
- —CN;
- —SCN;
- —SRG;
- —SORG;
- —SO2RG;
- —NO2;
- —N(RG)2;
- —NHC(O)RG;
- or —C(RG)3;
- wherein each occurrence of RG is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- Z is ═O or ═N—NHRD, wherein RD is a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- R1 is hydrogen;
- a protecting group;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —C(═O)RA;
- —C(═O)ORA;
- —C(═O)N(RA)2;
- or —C(RA)3;
- wherein each occurrence of RA is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- each occurrence of R2 is independently hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORB;
- —C(═O)RB;
- —CO2RB;
- —C(═O)N(RB)2;
- —CN;
- —SCN;
- —SRB;
- —SORB;
- —SO2RB;
- —NO2;
- —N(RB)2;
- —NHC(O)RB;
- or —C(RB)3;
- wherein each occurrence of RB is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- R3 is hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORC;
- —C(═O)RC;
- —CO2RC;
- —C(═O)N(RC)2;
- —CN;
- —SCN;
- —SRC;
- —SORC;
- —SO2RC;
- —NO2;
- —N(RC)2;
- —NHC(O)RC;
- or —C(RC)3;
- wherein each occurrence of RC is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- and
- R6 is hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORK;
- —C(═O)RK;
- —CO2RK;
- —C(═O)N(RK)2;
- —CN;
- —SCN;
- —SRK;
- —SORK;
- —SO2RK;
- —NO2;
- —N(RK)2;
- —NHC(O)RK;
- or —C(RK)3;
- wherein each occurrence of RK is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- and pharmaceutically acceptable salts thereof;
- provided that at least one instance of Y is not CRY.
194 more elements
A compound of formula (XI):
- wherein
- represents a double or triple bond;
- n is an integer between 0 and 3, inclusive;
- j is an integer between 0 and 8, inclusive;
- R1 is hydrogen;
- a protecting group;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —C(═O)RA;
- —C(═O)ORA;
- —C(═O)N(RA)2;
- or —C(RA)3;
- wherein each occurrence of RA is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- each occurrence of RY is independently hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORG;
- —C(═O)RG;
- —CO2RG;
- —C(═O)N(RG)2;
- —CN;
- —SCN;
- —SRG;
- —SORG;
- —SO2RG;
- —NO2;
- —N(RG)2;
- —NHC(O)RG;
- or —C(RG)3;
- wherein each occurrence of RG is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- each occurrence of R2 is independently hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORB;
- —C(═O)RB;
- —CO2RB;
- —C(═O)N(RB)2;
- —CN;
- —SCN;
- —SRB;
- —SORB;
- —SO2RB;
- —NO2;
- —N(RB)2;
- —NHC(O)RB;
- or —C(RB)3;
- wherein each occurrence of RB is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- R3 is hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORC;
- —C(═O)RC;
- —CO2RC;
- —C(═O)N(RC)2;
- —CN;
- —SCN;
- —SRC;
- —SORC;
- —SO2RC;
- —NO2;
- —N(RC)2;
- —NHC(O)RC;
- or —C(RC)3;
- wherein each occurrence of RC is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- R6 is hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORK;
- —C(═O)RK;
- —CO2RK;
- —C(═O)N(RK)2;
- —CN;
- —SCN;
- —SRK;
- —SORK;
- —SO2RK;
- —NO2;
- —N(RK)2;
- —NHC(O)RK;
- or —C(RK)3;
- wherein each occurrence of RK is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- and
- R7 is hydrogen;
- halogen;
- cyclic or acyclic, unsubstituted, branched or unbranched alkyl;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched alkenyl;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched alkynyl;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched carbocyclyl;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORC;
- —C(═O)RC;
- —CO2RC;
- —C(═O)N(RC)2;
- —CN;
- —SCN;
- —SRC;
- —SORC;
- —SO2RC;
- —NO2;
- —N(RC)2;
- —NHC(O)RC;
- —Si(RC)3;
- or —C(RC)3;
- wherein each occurrence of RC is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- and pharmaceutically acceptable salts thereof.
220 more elements
A compound of Formula (XIII):
- wherein
- j is an integer between 0 and 6, inclusive;
- each occurrence of Y is independently S, O, N, C or CRY, wherein each occurrence of RY is independently hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORG;
- —C(═O)RG;
- —CO2RG;
- —C(═O)N(RG)2;
- —CN;
- —SCN;
- —SRG;
- —SORG;
- —SO2RG;
- —NO2;
- —N(RG)2;
- —NHC(O)RG;
- or —C(RG)3;
- wherein each occurrence of RG is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety, wherein one, two, or three occurrences of Y are CH;
- R1 is hydrogen;
- a protecting group;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —C(═O)RA;
- —C(═O)ORA;
- —C(═O)N(RA)2;
- or —C(RA)3;
- wherein each occurrence of RA is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- provided that R1 is not a tert-butoxycarbonyl group;
- each occurrence of R2 is independently hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORB;
- —C(═O)RB;
- —CO2RB;
- —C(═O)N(RB)2;
- —CN;
- —SCN;
- —SRB;
- —SORB;
- —SO2RB;
- —NO2;
- —N(RB)2;
- —NHC(O)RB;
- or —C(RB)3;
- wherein each occurrence of RB is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- R3 is hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORC;
- —C(═O)RC;
- —CO2RC;
- —C(═O)N(RC)2;
- —CN;
- —SCN;
- —SRC;
- —SORC;
- —SO2RC;
- —NO2;
- —N(RC)2;
- —NHC(O)RC;
- or —C(RC)3;
- wherein each occurrence of RC is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino, alkylamino, dialkylamino, heteroaryloxy;
- or heteroarylthioxy moiety;
- provided that R3 is not —OCH2Ph;
- R4 and R5 are independently hydrogen or —OH;
- and
- R6 is hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, branched or unbranched acyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —ORK;
- —C(═O)RK;
- —CO2RK;
- —C(═O)N(RK)2;
- —CN;
- —SCN;
- —SRK;
- —SORK;
- —SO2RK;
- —NO2;
- —N(RK)2;
- —NHC(O)RK;
- or —C(RK)3;
- wherein each occurrence of RK is independently a hydrogen;
- a halogen;
- a protecting group;
- an aliphatic moiety;
- a heteroaliphatic moiety;
- an acyl moiety;
- an aryl moiety;
- a heteroaryl moiety;
- alkoxy;
- aryloxy;
- alkylthioxy;
- arylthioxy;
- amino;
- alkylamino;
- dialkylamino;
- heteroaryloxy;
- or heteroarylthioxy moiety;
- and pharmaceutically acceptable salts thereof.
176 more elements
A compound selected from the group consisting of:
Dependencies are inferred from the claim text.