Methods for producing Beraprost and its derivatives
Inventors
Batra, Hitesh • TULADHAR, Sudersan M. • Tummala, Sri Harsha • Penmasta, Raju • Walsh, David A.
Assignees
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Publication Number
US-10640481-B2
Publication Date
2020-05-05
Expiration Date
Abstract
The present invention is directed to methods for preparing Beraprost and novel synthetic intermediates for Beraprost.
Core Innovation
The invention relates to a method for preparing a compound represented by structural Formula (II) by transforming an α-tetralone of structural Formula (XXV) into related intermediates and then into Formula (II). The sequence comprises oxidizing the α-tetralone to form a benzolactone represented by structural Formula (XXVI), hydrolyzing the benzolactone Formula (XXVI) to provide the compound represented by structural Formula (XXVII), and halogenating the compound Formula (XXVII) to provide the compound of Formula (II).
The method specifies substituent and halogen constraints, wherein X is F, Cl, Br or I, and R1 is an alkyl, cycloalkyl or TBDMS. The claim defines the overall transformation sequence connecting α-tetralone, benzolactone, and halogenated products through oxidation, hydrolysis, and halogenation steps.
Claims Coverage
The provided material includes one independent claim. The claim covers a three-step synthetic preparation of a Formula (II) compound, with halogen and substituent constraints defining the scope.
Three-step conversion from α-tetralone to formula (II) via benzolactone and hydrolysis
A method for preparing a compound represented by structural Formula (II) by oxidizing an α-tetralone of Formula (XXV) to form a benzolactone of structural Formula (XXVI), hydrolyzing the benzolactone Formula (XXVI) to provide a compound of structural Formula (XXVII), and halogenating the compound Formula (XXVII) to provide compound of Formula (II).
Halogen and substituent constraints for the prepared structure
The method wherein X is F, Cl, Br or I, and R1 is an alkyl, cycloalkyl or TBDMS.
The claim coverage is centered on a defined three-stage sequence (oxidation to benzolactone, hydrolysis, then halogenation) to reach structural Formula (II), with explicit structural constraints for X and R1.
Stated Advantages
Economical synthesis.
Efficient synthesis.
Stereoselective synthesis.
Scalable synthesis.
Preparation of stereoisomerically pure intermediates.
Therapeutic suitability of the resulting compounds, including for pulmonary hypertension.
Documented Applications
Therapeutic use, including treatment contexts such as pulmonary hypertension.
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