612548-45-5

Basic information

• Product Name: Perindopril L-Arginine
• Synonyms: Perindopril L-Arginine;L-Arginine mono[(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylate];perindopril arginine
• CAS NO: 612548-45-5
• Molecular Formula: C₆H₁₄N₄O₂*C₁₉H₃₂N₂O₅
• Molecular Weight: 542.66874
• Product Categories: Amines, Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 612548-45-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: Perindopril L-Arginine(CAS DataBase Reference)
• NIST Chemistry Reference: Perindopril L-Arginine(612548-45-5)
• EPA Substance Registry System: Perindopril L-Arginine(612548-45-5)

Safety Data

• Hazardous Substances Data: 612548-45-5(Hazardous Substances Data)

Usage

Uses

Perindopril L-Arginine, is a complex compound of Perindopril (P287500), having the antihypertensive, cardiovascular protective and antithrombotic properties, and has been shown to exists as a neutral complex.

Definition

ChEBI: An organoammonium salt obtained by combining perindopril with one molar equivalent of L-arginine.

Synthetic route

N-(1-(S)-Ethoxycarbonylbutyl)-L-alanine + L-arginine (74-79-3) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → perindopril L-arginine (612548-45-5)

Conditions	Yield
Stage #1: N-(1-(S)-Ethoxycarbonylbutyl)-L-alanine; (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With triethylamine In acetonitrile at 10℃; for 5h; Stage #2: L-arginine In dimethyl sulfoxide at 50℃; for 5h; Reagent/catalyst; Temperature; Time; Concentration; Solvent;	89%

L-arginine (74-79-3) + perindopril tert-butylamine (107133-36-8) → perindopril L-arginine (612548-45-5)

Conditions	Yield
With methanesulfonic acid In dimethyl sulfoxide at 70℃; for 1h;	88%

L-arginine (74-79-3) + Perindopril (82834-16-0) → perindopril L-arginine (612548-45-5)

Conditions	Yield
In dimethyl sulfoxide; acetonitrile at 50℃;	79%
In water at 20℃;
In ethanol; dichloromethane at 70 - 75℃;
In ethanol; dichloromethane at 45 - 75℃;
In methanol at 20℃; Product distribution / selectivity; Reflux;

perindopril L-arginine (612548-45-5) → C17H26N2O4 + perindoprilat (95153-31-4)

Conditions	Yield
With water; 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide at 59.84℃; for 250h; Kinetics;

Upstream product

• 74-79-3 L-arginine 
• 80875-98-5 (2S,3aS,7aS)-perhydroindole-2-carboxylic acid 
• 107133-36-8 perindopril tert-butylamine 
• 82834-16-0 Perindopril 

Downstream Products

• 95153-31-4 perindoprilat 

Relevant articles and documents

DELTA CRYSTALLINE FORM OF THE ARGININE SALT OF PERINDOPRIL, A PROCESS FOR ITS PREPARATION, AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT

Delta crystalline form of the compound of formula (I): characterised by its X-ray powder diffraction diagram. Medicinal products containing the same which are useful in the treatment of cardiovascular diseases.

AMORPHOUS FORM OF AN L-ARGININE SALT OF PERINDOPRIL AND PROCESSES FOR PREPARATION THEREOF

In illustrative embodiments, there is provided an amorphous form of L-arginine salt of perindopril which may be particularly suitable for pharmaceutical applications, and processes for preparing said form.

Alpha Crystalline form of the Arginine salt of Perindopril, a Process for its Preparation and Pharmceutical Compositions Containing it.

α-crystalline form of the compound of formula (I): characterised by its powder X-ray diffraction diagram. Medicinal products containing the same which are useful as inhibitors of angiotensin I converting enzyme.