Heterocyclic quinolone derivatives that inhbit prolyl hydroxylase activity

A composition of matter, comprising at least one compound of Formula I:

• a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer;
• or a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, or a mixture of any of the foregoing, wherein:
• J is selected from CR7 or N;
• n is 1 to 6;
• R1 and R2 are independently selected in each instance from H, lower alkyl, substituted lower alkyl, lower haloalkyl, or substituted lower haloalkyl, or R1 and R2 can join together to form a 3 to 6 membered ring or a substituted 3 to 6 membered ring;
• X is selected from —NRa—, —O—, —S—, or —(CRbRc)—, wherein Ra is selected from H or lower alkyl, and Rb and Rc are independently selected from H, lower alkyl, substituted lower alkyl, lower haloalkyl, or substituted lower haloalkyl, or Rb and Rc can join together to form a 3 to 6 membered ring or a substituted 3 to 6 membered ring;
• R3 is selected from OH, SH, NH2, lower alkyl, substituted lower alkyl, lower alkoxy, substituted lower alkoxy, or sulfanyl;
• R4 is selected from H, OH, lower alkoxy, SH, NH2, NHSO2R8, or sulfonyl;
• R5 is selected from H, lower alkyl, or substituted lower alkyl;
• R6 and R7 are independently selected from H, F, Cl, Br, I, alkyl, substituted alkyl, haloalkyl, perhaloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, NRdRe, C(O)R8, C(O)OR9, OR9, SR9, SO2R9, CN, NO2, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, heterocyclyl, substituted heterocyclyl, heterocyclylalkyl, substituted heterocyclylalkyl, or —Y—R10;
• or, R6 and R7 may join to form an optionally substituted 5 or 6 membered ring when J is CR7 wherein:
• Y is selected from —N(R11)-Z- or -Z-N(R11)—;
• Z is selected from C(O), SO2, alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene, or substituted alkynylene;
• R8 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;
• R9 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, or substituted alkynyl;
• R10 is selected from H, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;
• R11 is selected from H, lower alkyl, or substituted lower alkyl;
• and
• Rd and Re are independently selected from H, lower alkyl, substituted lower alkyl, lower haloalkyl, or substituted lower haloalkyl, or Rd and Re can join together to form a 3 to 6 membered ring or a substituted 3 to 6 membered ring,
• wherein R1 and R2 are not both H if X is —NRa—;
• Ra is H;
• and n is 1.

A composition of matter, comprising at least one compound of Formula I:

• a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer;
• or a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, or a mixture of any of the foregoing, wherein:
• J is selected from CR7 or N;
• n is 1;
• R1 and R2 are both H;
• X is —NRa—, wherein Ra is selected from H or lower alkyl;
• R3 is selected from OH, SH, NH2, lower alkyl, substituted lower alkyl, lower alkoxy, substituted lower alkoxy, or sulfanyl;
• R4 is selected from H, OH, lower alkoxy, SH, NH2, NHSO2R8, or sulfonyl;
• R5 is selected from H, lower alkyl, or substituted lower alkyl;
• R6 and R7 are independently selected from H, F, Cl, Br, I, alkyl, substituted alkyl, haloalkyl, perhaloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, NRdRe, C(O)R8, C(O)OR9, OR9, SR9, SO2R9, CN, NO2, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, substituted heteroarylalkyl, heterocyclyl, substituted heterocyclyl, heterocyclylalkyl, substituted heterocyclylalkyl, or —Y—R10—;
• or, R6 and R7 may join to form an optionally substituted 5 or 6 membered ring when J is CR7, wherein:
• Y is selected from —N(R11)-Z- or -Z-N(R11)—;
• Z is selected from C(O), SO2, alkylene, substituted alkylene, alkenylene, substituted alkenylene, alkynylene, or substituted alkynylene;
• R8 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;
• R9 is selected from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, or substituted alkynyl;
• R10 is selected from H, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl;
• R11 is selected from H, lower alkyl, or substituted lower alkyl;
• and
• Rd and Re are independently selected from H, lower alkyl, substituted lower alkyl, lower haloalkyl, or substituted lower haloalkyl, or Rd and Re can join together to form a 3 to 6 membered ring or a substituted 3 to 6 membered ring.