946150-57-8

Basic information

• Product Name: SHP-141
• Synonyms: SHP-141
• CAS NO: 946150-57-8
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.34104
• EINECS: -0
• Mol File: 946150-57-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: SHP-141(CAS DataBase Reference)
• NIST Chemistry Reference: SHP-141(946150-57-8)
• EPA Substance Registry System: SHP-141(946150-57-8)

Safety Data

• Hazardous Substances Data: 946150-57-8(Hazardous Substances Data)

Usage

General Description

SHP-141, also known as S-1152, is a selective and potent antagonist of the adenosine A2A receptor. It is a chemical compound with the potential to be used in the treatment of various central nervous system disorders, including Parkinson's disease. Research has shown that SHP-141 has the ability to reduce motor deficits and provide neuroprotection in animal models of Parkinson's disease. Additionally, SHP-141 has been found to be well-tolerated and to have a good safety profile in preclinical studies, making it a promising candidate for further development as a potential therapeutic agent for neurological disorders.

Upstream product

• 99-76-3 methyl 4-hydroxylbenzoate 
• 10521-06-9 oxonane-2,9-dione 

Downstream Products

• 99-76-3 methyl 4-hydroxylbenzoate 

Relevant articles and documents

Process Development of the Soft Histone Deacetylate Enzyme Inhibitor SHP-141: Acylation of Methyl Paraben and Suberyl Hydroxamic Acid Formation

SHP-141 (1) is a hydroxamic acid-based inhibitor of histone deacetylase enzymes which is under development for the treatment of cutaneous T-cell lymphoma. The original synthesis of 1 involved five synthetic steps beginning with suberic acid monomethyl ester. Final deprotection of the O-benzyl hydroxamate moiety using hydrogen and palladium catalyst mandated the use of metal scavengers to reduce palladium levels to within International Council for Harmonisation (ICH) guidance. Owing to the sensitivity of 1 toward self-condensation and the potential for N-O bond cleavage under hydrogenolytic conditions, we developed an alternative route to 1 which avoids Pd-mediated hydrogenation and prolonged metal scavenger treatment. This two-step process employs readily available suberic acid and methyl paraben and has successfully delivered multiple kilograms of 1 for clinical use. Importantly, crude 1 was stabilized for recrystallization in acetonitrile (ACN) solution by the addition of 0.1% citric acid and 4% water. Additionally, the filtration and drying of suitably sized aggregates of 1 with high purity (100 area%) was accomplished via temperature cycling of the 1/ACN solution.