78664-73-0

Basic information

• Product Name: Posatirelin
• Synonyms: Posatirelin;N-[(S)-6-Oxo-2-piperidinylcarbonyl]-L-Leu-L-Pro-NH2;RGH-2202
• CAS NO: 78664-73-0
• Molecular Formula: C17H28N4O4
• Molecular Weight: 352.432
• Mol File: 78664-73-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 214-216°
• Boiling Point: 739.6°C at 760 mmHg
• Flash Point: 401.1°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 9.66E-22mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: Posatirelin(CAS DataBase Reference)
• NIST Chemistry Reference: Posatirelin(78664-73-0)
• EPA Substance Registry System: Posatirelin(78664-73-0)

Safety Data

• Hazardous Substances Data: 78664-73-0(Hazardous Substances Data)

Usage

Pharmacological Study

Posatirelin is a TRH analogue. In a rat experimental model of brain cholinergic deficit by lesion of the nucleus basalis magnocellularis (nbM), posatirelin treatment rescued cholinergic neurones of the nbM and their cholinergic projections to the cerebral cortex (Sabbatini et al., 1998). Posatirelin has been used in AD and VaD patients (Parnetti et al., 1995, 1996). VaD patients treated with posatirelin showed a significant improvement in intellectual performance, orientation, motivation and memory as compared to controls. The drug was well tolerated.

Description

Posatirelin is a TRH analogue. In a rat experimental model of brain cholinergic decit by lesion of the nucleus basalis magnocellularis (nbM), posatirelin treatment rescued cholinergic neurones of the nbM and their cholinergic projections to the cerebral cortex (Sabbatini et al., 1998). Posatirelin has been used in AD and VaD patients (Parnetti et al., 1995, 1996). VaD patients treated with posatirelin showed a signicant improvement in intellectual performance, orientation, motivation and memory as compared to controls. e drug was well tolerated.

Uses

Posatirelin is a thyrotropin-releasing hormone analogue, used in the treatment of seizures and some neurodegenerative disease such as vascular dementia and Parkinson''s disease.

InChI:InChI=1/C17H28N4O4/c1-10(2)9-12(17(25)21-8-4-6-13(21)15(18)23)20-16(24)11-5-3-7-14(22)19-11/h10-13H,3-9H2,1-2H3,(H2,18,23)(H,19,22)(H,20,24)/t11-,12-,13-/m0/s1

Upstream product

• 83793-27-5 L-2-amino-5-<(benzyloxycarbonyl)carbamoyl>pentanoic acid 
• 102922-72-5 (S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoic acid 
• 34622-39-4 (2S)-6-oxopipecolic acid 
• 24325-14-2 (2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 1118-90-7 L-homoglutamic acid 
• 6033-32-5 (S)-2-amino-6-hydroxyhexanoic acid 
• 78664-34-3 H-Leu-Pro-NH₂*HCl 
• 78664-72-9 L-pyro-2-aminoadipic acid pentafluorophenyl ester 

Relevant articles and documents

Synthesis of Thyrotropin-Releasing Hormone Analogues. 2. Tripeptides Structurally Greatly Differing from TRH with High Central Nervous System Activity

A new series of thyrotropin-releasing hormone (TRH) analogues, obtained by further modifications of our most potent central nervous system (CNS) stimulating neutral tripeptides at both termini, were synthesized by the pentafluorophenyl ester method and tested for CNS and thyrotropin (TSH) releasing activity.Replacement of pyroglutamic acid by pyro-2-aminoadipic acid, 2-oxoimidazolidine-4-carboxylic acid or γ-butyrolactone-γ-carboxylic acid and that of proline by pipecolic acid, thiazolidine-4-carboxylic acid, or homoproline in 2>- and 2>TRH led to tripeptides structurally widely different from TRH.In spite of this fact, 7 of the 17 analogues (1, 2, 8-10, 16, and 17) have stronger anticataleptic effect than TRH, with negligible or no hormonal potency.The highest CNS activity was achieved when pyroglutamic acid was replaced by pyro-2-aminoadipic acid at the N-terminus .A novel synthesis of L-2-aminoadipic acid suitable for large-scale preparation is also described.