144412-49-7

Usage

Uses

Antithrombotic.

InChI:InChI=1/C24H28N4O6/c25-22(26)16-3-5-17(6-4-16)23(32)27-20(13-15-1-7-18(29)8-2-15)24(33)28-11-9-19(10-12-28)34-14-21(30)31/h1-8,19-20,29H,9-14H2,(H3,25,26)(H,27,32)(H,30,31)/t20-/m0/s1

Upstream product

• 351184-45-7 {1-[2-[4-(N-hydroxycarbamimidoyl)-benzoylamino]-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid 
• 15535-95-2 4-(aminoiminomethyl)benzoic acid 
• 146118-32-3 {1-[(S)-2-Benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid tert-butyl ester 
• 144412-13-5 t-butyl [[1-[3-(p-t-butoxyphenyl)-L-alanyl]-4-piperidinyl]oxy]acetate 
• 144412-43-1 t-Butyl 2-(1-benzyloxycarbonyl-4-piperidyl)oxyacetate 
• 144412-03-3 (Piperidin-4-yloxy)-acetic acid tert-butyl ester 
• 95798-23-5 1-(benzyloxycarbonyl)-4-hydroxypiperidine 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 442845-58-1 {1-[3-(4-tert-butoxy-phenyl)-2-(4-cyano-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic acid tert-butyl ester 
• 351184-44-6 4-cyano-N-[1-(4-hydroxy-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-benzamide 
• 178601-17-7 (S)-<<1-<2-<4-<(aminoiminomethyl)benzoyl>amino>-3-(4-hydroxyphenyl)propionyl>piperidin-4-yl>oxy>acetic acid tert-butyl ester 
• 5545-54-0 N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine 

Downstream Products

• 170094-36-7 {1-[(S)-2-(4-{Amino-[(Z)-ethoxycarbonylimino]-methyl}-benzoylamino)-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid isopropyl ester 

Relevant academic research and scientific papers

Concise synthesis of sibrafiban and lamifiban, two non-peptide fibrinogen receptor (GP IIb/IIIa) antagonists

The total synthesis of the non-peptide fibrinogen receptor antagonists, sibrafiban (1) (Ro 48-3657) and lamifiban (2) (Ro 44-9883), is described. Both contain 4-hydroxypiperidine unit and the same solid-phase synthesis method was used as a key step. Conne

Low molecular weight, non-peptide fibrinogen receptor antagonists

The tetrapeptide H-Arg-Gly-Asp-Ser-OH (1) (RGDS), representing a recognition sequence of fibrinogen for its platelet receptor GP IIb-IIIa (integrin α(IIb)β3), served as lead compound for the development of highly potent and selective fibrinogen receptor antagonists. Replacement of the N- terminal arginine by p-amidinophenylalanine or the Gly moiety by m- aminobenzoic acid led to compounds which are superior to the lead peptide with regard to activity and selectivity for GP IIb-IIIa vs the closely related vitronectin receptor α(v)β3. By random screening [(p- amidinobenzenesulfonamido)ethyl]-p-phenoxyacetic acid derivatives have been identified as fibrinogen receptor antagonists. Further structure-activity relationship studies culminated in the preparation of N-[N-[N-(p- amidinobenzoyl)-β-alanyl]-L-α-aspartyl]-3-phenyl-L-alanine (29h, Ro 43- 5054) and [[1-[N-(p-amidinobenzoyl)-L-tyrosyl]-4-piperidinyl]oxy]acetic acid (37f, Ro 44-9883), which exhibit very high activity as platelet aggregation inhibitors (IC50s 0.06 and 0.03 μM, respectively, human PRP/ADP) as well as marked selectivity for GP IIb-IIIa vs α(v)β3. Since the activity of 37f in dogs declines according to a two-compartment model with an initial phase having a t( 1/2 ) of 8 min and a second phase with a t( 1/2 ) of 110 min, this compound is a suitable candidate for the development as iv platelet inhibitor.