81845-98-9

Usage

Uses

Used in Pharmaceutical Industry:
2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester is used as a pharmaceutical agent for the treatment of pulmonary arterial hypertension (PAH). It functions as an impurity of Treprostinil (T719500), a synthetic analog of Prostacyclin (P839060), which is a medication marketed under the trade name Remodulin. 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester exhibits antihypertensive properties and helps in managing the symptoms of PAH.
Used in Drug Delivery Systems:
2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester can also be employed in drug delivery systems to improve the bioavailability and therapeutic outcomes of various drugs. Its unique molecular structure allows for the development of novel drug delivery systems, such as organic and metallic nanoparticles, which can enhance the delivery and efficacy of the compound in treating specific medical conditions.

Upstream product

• 67-56-1 methanol 
• 81846-19-7 treprostinil 
• 1355990-19-0 {(1R,6S)-1-[-2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-ynyloxy}-tert-butyl-dimethyl-silane 
• 1355990-17-8 (1R,6S)-1-[-2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-yn-1-ol 
• 1355990-15-6 (S)-1-[2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-yn-1-one 
• 1355990-13-4 (S)-1-[2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-yn-1-ol 
• 79950-42-8 2-allyl-3-hydroxy-benzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 96-32-2 bromoacetic acid methyl ester 
• 101692-02-8 (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol 
• 40359-32-8 3-allyloxy-benzaldehyde 
• 1355990-09-8 2-allyl-3-(4-methoxybenzyloxy)benzaldehyde 
• 1355990-25-8 (1R,2R,3aS,9aS)-1-((S)-3-benzyloxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol 
• 1355990-23-6 (3aS,9aS)-1-((S)-3-benzyloxyoctyl)-5-hydroxy-1,3,3a,4,9,9a-hexahydrobenz[f]inden-2-one 

Downstream Products

• 81846-19-7 treprostinil 

Relevant academic research and scientific papers

Process for Preparing Treprostinil and Intermediate Therefor

The present invention relates to a synthesis method of high-purity treprostinil, and an intermediate for the same. According to the synthesis method of the present invention, high-purity treprostinil can be synthesized in an economical and efficient manner by using intramolecular Friedel-Crafts allylic alkylation. Accordingly, the synthesis method of the present invention may be effectively used for commercial mass-production of treprostinil.COPYRIGHT KIPO 2017

Process for Preparing Treprostinil

The present invention relates to a synthesis method of treprostinil, and more specifically, to a method of synthesizing high-purity treprostinil in an economical and efficient manner; and to high-purity treprostinil crystals synthesized by the method. According to the synthesis method of the present invention, treprostinil having a purity of 99.9% or more can be produced in an economical and efficient manner.COPYRIGHT KIPO 2017

COMPOUNDS AND METHODS FOR DELIVERY OF PROSTACYCLIN ANALOGS

This invention pertains generally to prostacyclin formulations and methods for their use in promoting vasodilation, inhibiting platelet aggregation and thrombus formation, stimulating thrombolysis, inhibiting cell proliferation (including vascular remodeling), providing cytoprotection, preventing atherogenesis and inducing angiogenesis.

Synthesis Of Treprostinil And Intermediates Useful Therein

Treprostinil is prepared by a process which involves Pauson-Khan cyclization of an an alkene-substituted, alkyne-substituted benzene corresponding to formula: (I) where PMB represents para-methoxy benzyl protecting group and R1 and R2 are alcohol protecting groups. Following cyclization, the resulting compound can be subjected to several chemical trans-formations followed by alkylation, hydrolysis and salt formation to yield treprostinil sodium. The use of para-methoxybenzyl group as the phenolic protecting group confers several process advantages that result in simplified purification of the final product and improved yields.

SYNTHESIS OF TREPROSTINIL AND INTERMEDIATES USEFUL THEREIN

Treprostinil is prepared by a process which involves Pauson - Khan cyclization of an an alkene-substituted, alkyne-substituted benzene corresponding to formula : (I) where PMB represents para-methoxy benzyl protecting group and R1 and R2 are alcohol protecting groups. Following cyclization, the resulting compound can be subjected to several chemical transformations followed by alkylation, hydrolysis and salt formation to yield treprostinil sodium. The use of para-methoxybenzyl group as the phenolic protecting group confers several process advantages that result in simplified purification of the final product and improved yields.

PROCESS FOR TREPROSTINIL SALT PREPARATION

Disclosed is a process for preparing a treprostinil salt. The process involves the step of dissolving treprostinil in a water-miscible organic solvent to form a treprostinil solution. The treprostinil solution is reacted with an aqueous basic solution containing an alkali metal cation to form treprostinil salt. Allowing crystallization of the treprostinil salt to take place, and then collecting the treprostinil salt formed.