Prodrugs of treprostinil
Inventors
Batra, Hitesh • Guo, Liang • Poisson, Patrick • Tummala, Sri Harsha • HARRIS, Elizabeth Ann
Assignees
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Publication Number
US-12357599-B2
Publication Date
2025-07-15
Expiration Date
Abstract
Provided are novel treprostinil based compounds, methods of treatment using the same, and their methods of making.
Core Innovation
The invention relates to FDKP-treprostinil prodrugs as compounds of formula 5a or 5b, also referred to as FDKP-treprostinil compounds. The compounds include an FDKP moiety and a treprostinil moiety, and the treprostinil portion is functionalized with a polymeric carrier as part of the prodrug design. Pharmaceutically acceptable salts are included.
The document states that treprostinil prodrugs of formula 5a/5b are prepared by double-protecting treprostinil hydroxyl and carboxyl groups, coupling with an FDKP moiety, and deprotecting to yield the FDKP-treprostinil compounds. Protecting-group types described include silyl and benzyl carboxylic acid protecting groups, with silyl-cleaving and benzyl-carboxyl protecting-group cleavage agents mentioned as classes.
Treatment methods in the document are directed to treprostinil-treatable conditions, with pulmonary hypertension and pulmonary arterial hypertension explicitly identified. Pharmaceutical compositions and general formulation routes are also included as part of the disclosed treprostinil prodrug use.
Claims Coverage
The claim set contains 1 independent claim, with dependent claims refining the scope by specifying the carboxylic acid protecting group at R1 while leaving R2, R3, and R5 defined by the independent claim.
Compound structure with protecting groups and polymeric carrier
A compound of (4a) or (4b) wherein R1 is a carboxylic acid protecting group, R2 is H or a hydroxyl protecting group, R3 is H or a hydroxyl protecting group, and R5 is a polymeric carrier.
R1 as silyl or benzyl carboxylic acid protecting group
R1 is a silyl carboxylic acid protecting group or a substituted or unsubstituted benzyl carboxylic acid protecting group.
R1 as a specified list of silyl carboxylic acid protecting groups
R1 is a silyl carboxylic acid protecting group chosen from trimethylsilyl, triethylsilyl, tri-iso-propylsilyloxymethyl, triisopropyl silyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, and phenyldimethylsilyl.
R1 as trimethylsilyl
R1 is trimethylsilyl.
R1 as substituted or unsubstituted benzyl carboxylic acid protecting group
R1 is a substituted or unsubstituted benzyl carboxylic acid protecting group.
R1 as benzyl group
R1 is a benzyl group.
Claim coverage centers on FDKP-treprostinil compounds of (4a)/(4b) defined by protecting groups on treprostinil and a polymeric carrier at R5, with dependent claims narrowing R1 to silyl or benzyl options, including specific silyl examples and benzyl.
Stated Advantages
Documented Applications
Use of deprotection strategies to obtain unprotected FDKP-treprostinil and to generate protected intermediates and ester derivatives for the disclosed FDKP-treprostinil prodrug embodiments.
Provision of polymeric carrier-containing FDKP-treprostinil prodrug compounds by defining R5 as a polymeric carrier in the claimed compound structures.
Treatment methods directed to treprostinil-treatable conditions, including pulmonary hypertension and pulmonary arterial hypertension.
Pharmaceutical compositions and general formulation routes.
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