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US 10,344,012 B2Granted
Treprostinil derivative compounds and methods of using same
AssigneeCorsair Pharma, Inc.
InventorsCyrus K. Becker, Meenakshi S. Venkatraman, Xiaoming Zhang, Jürg Pfister
Life of this patent
Estimating the term…
Abstract
Compounds represented by formulae I, II, III, and IV including pro-drugs for treprostinil and prostacyclin analogs. Uses include treatment of pulmonary hypertension (PH) or pulmonary arterial hypertension (PAH). The structures of the compounds can be adapted to the particular application for a suitable treatment dosage. Transdermal applications can be used.
Claims15
A compound represented by Formula II:
- wherein:
- R2 is selected from the group consisting of H and P2;
- R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, and R36 are independently selected from the group consisting of H and deuterium;
- L1 is selected from the group consisting of —O-alkylene-C(O)—, —O-alkylene-OC(O)—, and a bond;
- and
- P2 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 atom(s) to which they are attached optionally form a 5- to 7-membered ring which incorporates one or two ring heteroatoms chosen from N, O, and S, and which is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, methyl, and methoxy;
- R16 and R17 are independently H or alkyl;
- or
- R16 and R17 taken together with the atom to which they are attached optionally form a 3- to 6-membered ring;
- and
- R18 and R19 are independently in each occurrence selected from the group consisting of hydrogen and 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 is unsubstituted or substituted with a substituent selected from the group consisting of alkyl, halo, haloalkyl, hydroxy, alkoxy, and haloalkoxy;
- or
- R14 and R18 taken together with the atoms to which they are attached optionally form a 5- to 7-membered ring;
- or
- R14 and R19 taken together with the atoms to which they are attached optionally form a 5- to 7-membered ring;
- or an enantiomer or a pharmaceutically acceptable salt thereof.
18 more elements
A compound represented by Formula IV:
- wherein:
- R1 is selected from the group consisting of H and P2;
- R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, and R36 are independently selected from the group consisting of H and deuterium;
- L1 is selected from the group consisting of —O-alkylene-C(O)—, —O-alkylene-OC(O)—, and a bond;
- P2 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 atom(s) to which they are attached optionally form a 5- to 7-membered ring which incorporates one or two ring heteroatoms chosen from N, O, and S, and which is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from the group consisting of halo, methyl, and methoxy;
- R16 and R17 are independently H or alkyl;
- or
- R16 and R17 taken together with the atom to which they are attached optionally form a 3- to 6-membered ring;
- and
- R18 and R19 are independently in each occurrence selected from the group consisting of hydrogen and 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 is unsubstituted or substituted with a substituent selected from the group consisting of alkyl, halo, haloalkyl, hydroxy, alkoxy, and haloalkoxy;
- or
- R14 and R18 taken together with the atoms to which they are attached optionally form a 5- to 7-membered ring;
- or
- R14 and R19 taken together with the atoms to which they are attached optionally form a 5- to 7-membered ring;
- or an enantiomer or a pharmaceutically acceptable salt thereof.
17 more elements
Dependencies are inferred from the claim text.