Treprostinil derivative compounds and methods of using same

A compound represented by Formula (I):

• wherein:
• R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35 and R36 are independently H or deuterium;
• Z is —OH, —N(R11)R12, —SR11 or P1;
• R11 is alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, haloalkyl, heteroalkyl, substituted heteroalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, alkylcycloalkyl, substituted alkylcycloalkyl, alkylcycloheteroalkyl, substituted alkylcycloheteroalkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heteroaryl, substituted heteroaryl, alkylheteroaryl, or substituted alkylheteroaryl;
• R12 is H, haloalkyl, heteroalkyl, cycloheteroalkyl, alkylcycloalkyl, alkylcycloheteroalkyl, aryl, or heteroaryl;
• P1 is selected from the group consisting of:
• wherein:
• m is 1, 2, 3 or 4;
• R14 and R15 are independently in each occurrence selected from the group consisting of H, alkyl, cycloalkyl, alkylcycloalkyl, haloalkyl, heteroalkyl, substituted alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, substituted aryl, substituted heteroaryl, substituted arylalkyl, and substituted heteroarylalkyl;
• or
• R14 and R15 taken together with the atoms to which they attach optionally form a 5- to 7-membered ring optionally incorporating one or two ring heteroatoms chosen from N, O and S, which is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from the group consisting of halo, methyl and methoxy;
• R18 and R19 are independently in each occurrence hydrogen or alkyl, wherein the alkyl is unsubstituted or substituted with 1 substituent selected from the group consisting of halo, hydroxy, alkoxy, amino, thio, methylthio, —C(O)OH, —C(O)O-(alkyl), —CONH2, aryl and heteroaryl, wherein the aryl or heteroaryl are unsubstituted or substituted with a substituent selected from the group consisting of alkyl, halo, haloalkyl, hydroxy, alkoxy, and haloalkoxy;
• R14 and R13 taken together with the atoms to which they attach optionally form a 5- to 7-membered ring;
• R14 and R19 taken together with the atoms to which they attach optionally form a 5- to 7-membered ring;
• R15 and R18 taken together with the atoms to which they attach optionally form a 5- to 7-membered ring;
• and
• R15 and R19 taken together with the atoms to which they attach optionally form a 5- to 7-membered ring;
• and
• R1 and R2 are independently H or P2, wherein at least one of R1 and R2 is P2, wherein P2 is selected from the group consisting of:
• wherein:
• m is 1, 2, 3 or 4;
• and
• R14 is selected from the group consisting of H, cycloalkyl, alkylcycloalkyl, haloalkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, substituted aryl, substituted heteroaryl, substituted arylalkyl, and substituted heteroarylalkyl;
• or an enantiomer or a pharmaceutically acceptable salt thereof.