18637-00-8

Basic information

• Product Name: 2-Ethoxybenzamidine hydrochloride
• Synonyms: 2-ETHOXY-BENZAMIDINE HCL;2-ETHOXYBENZAMIDINE HYDROCHLORIDE;2-Ethoxybenzenecarboximidamide.HCl;Ethoxyamidin;Ethoxy Benzamidine Hydrochloride;2-EthoxybenziMidaMide hydrochloride;Vardenafil IMpurity (2-Ethoxy BenzaMidine Hydrochloride);Vardenafil impurity E
• CAS NO: 18637-00-8
• Molecular Formula: C₉H₁₂N₂O*ClH
• Molecular Weight: 200.67
• EINECS: 242-575-2
• Product Categories: Miscellaneous;pharmacetical;Erectile Dysfunction
• Mol File: 18637-00-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 192oC at 760 mmHg
• Flash Point: 66.7oC
• Appearance: /
• Density: 2.209g/cm3
• Vapor Pressure: 0.5mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-Ethoxybenzamidine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxybenzamidine hydrochloride(18637-00-8)
• EPA Substance Registry System: 2-Ethoxybenzamidine hydrochloride(18637-00-8)

Safety Data

• Hazardous Substances Data: 18637-00-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Ethoxybenzamidine hydrochloride is used as an impurity in the production of Vardenafil (diHCl salt: V098001) for the treatment of erectile dysfunction in men. Its presence is significant for ensuring the safety, efficacy, and quality of the final pharmaceutical product. The compound is subject to regulatory guidelines and must be controlled within specified limits to maintain the therapeutic integrity of Vardenafil.

InChI:InChI=1/C3H3Br2ClO/c4-1-2(5)3(6)7/h2H,1H2

Upstream product

• 421-20-5 Methyl fluorosulfonate 
• 64633-71-2 ethyl 2-ethoxybenzimidate fluorosulfonate 
• 938-73-8 2-ethoxybenzamide 
• 6609-57-0 2-ethoxybenzonitrile 
• 75-24-1 trimethylaluminum 

Downstream Products

• 346605-61-6 N-[6-Amino-2-(2-ethoxyphenyl)-4-oxo-5-propyl-4,5-dihydro-pyrimidin-5-yl]-acetamide 
• 927690-90-2 N-{1-[3-(2-ethoxyphenyl)-5-oxo-4,5-dihydro-[1,2,4]triazin-6-yl]ethyl}butyroamide 
• 224789-21-3 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one 
• 346605-64-9 N-[6-amino-5-cyclopentyl-2-(2-ethoxyphenyl)-4-oxo-4,5-dihydropyrimidin-5-yl]acetamide 
• 889943-46-8 2-ethoxybenzimidohydrazide 
• 63874-50-0 2-(2-ethoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 1613637-87-8 2-(3-methoxyphenyl)-4-phenyl-1,3,5-triazine 

Relevant articles and documents

Alternative method for the synthesis of imidazo[5,1-f][1,2,4]triazin-4(3H)- one - A substrate for the preparation of phosphodiesterase (5) inhibitors

Imidazo[5,1-f][1,2,4]triazin-4(3H)-ones, as isosteres of purine, are of interest for pharmaceutical research as potential substrates for the synthesis of cGMP-PDE5 inhibitors. We present a novel, alternative method for the synthesis of imidazotriazinones, that differs from the previously reported ones with respect to the method of construction of the triazinone ring in the molecule. The key step in our approach is condensation of an appropriate α-keto-ester with amidrazones, leading to the triazinone heterocycle. Several different substituted imidazolotriazinones have been synthesized in this manner.

NEW AGENTS FOR THE TREATMENT OF THE LOW URINARY TRACT DYSFUNCTIONS

The present invention relates to novel compounds that are derivatives of 5 -phosphodiesterase inhibitors that comprise in their formula a polysulfurated group and that are useful for treating dysfunctions of low urinary tract such as incontinence, benign prostatic hyperplasia and erectile dysfunction.

Novel imidazotriazinones and the use thereof

Novel imidazotrizinones of general formula (I), a method for the production and the pharmaceutical use thereof are disclosed.

Novel imidazo[1,3,5]triazinones and the use thereof

The invention relates to novel imidazo[1,3,5]triazinones of the general formula (I), to a method for their production and to their use as medicaments, in particular as inhibitors of cyclic GMP metabolising phosphodiesterases.

Process for the preparation of sulphonamide-substituted imidazotriazinones

The present invention relates to a process for the preparation of sulphonamide-substituted imidazotriazinones of the general formula (I) characterized in that compounds of the formula (II) are reacted with sulphuric acid and the products obtained are then reacted with thionyl chloride and converted in situ in an inert solvent using an amine into the compounds according to the invention and, if appropriate, reacted to give the corresponding salts, hydrates or N-oxides.

2-Phenyl-substituited Imidazotriazinones as Phoshodiesterase Inhibitors

2-(Sulfamoyl-substituted phenyl)-3H-imidazo (5,1-f) (1,2,4) triazin-4-ones (I) are new. Imidazotriazinones of formula (I) and their salts, N-oxides and isomeric forms are new: R1 = H or 1-4C alkyl; R2 = 1-4C straight chain alkyl; R3, R4 = H, 2-8C alkenyl, 1-8C alkoxy or 1-10C alkyl (optionally interrupted by O and/or substituted by a very wide range of specific groups); or R3 or R4 = NR20R21, adamantyl, 2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl, sulfolanyl, hydroxy-sulfolanyl, 2-oxo-tetrahydrofuran-3-yl; or 3-8C cycloalkyl, 6-10C aryl or 5-7 membered heterocycle, all optionally substituted by specific groups; or NR3R4 = (a) optionally benzo-fused, saturated, partially unsaturated or unsaturated 5-7 membered heterocycle, optionally containing 1-3 of S, N, O and NR37 and optionally substituted by a very wide range of specific groups; or (b) a group of formula (i)-(iv); R20,R21 = H or 1-6C alkyl; R37 = H, OH, CHO, CF3, up to 4C acyl, up to 4C alkoxycarbonyl, 1-4C alkoxy, 1-6C alkyl (optionally substituted by specific groups) or -(CO)iE; i = 0 or 1; E = 3-7C cycloalkyl or benzyl; 6-10C aryl or 5- or 6-membered heteroaryl, both optionally substituted by specific groups ; or 5-methyl-1-oxo-2,1,3-oxadiazol-4-yl, N-methylpiperazino or morpholino; R5,R6 = H, 1-6C alkyl, OH or 1-6C alkoxy. The full definitions are given in the DEFINITIONS (Full Definitions) field. An Independent claim is included for the preparation of (I).

Imidazo[5,1-f][1,2,4]triazin-4(3H)-ones, a new class of potent PDE 5 inhibitors

2-Aryl-substituted imidazo[5,1-f][1,2,4]triazin-4(3H)-ones represent a new class of potent cGMP-PDE 5 inhibitors that prove to be superior to other purine-isosteric inhibitors. Subnanomolar inhibitors of PDE 5 with activity in in vivo models for erectile dysfunction have been identified. BAY 38-9456 (Vardenafil-hydrochloride) has been selected for clinical studies in the indication of erectile dysfunction.

2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors

The 2-phenyl-substituted imidazotriazinones having short, unbranched alkyl radicals in the 9-position are prepared from the corresponding 2-phenyl-imidazotriazinones by chlorosulphonation and subsequent reaction with the amines. The compounds inhibit cGMP-metabolizing phosphodiesterases and are suitable for use as active compounds in pharmaceuticals, for the treatment of cardiovascular and cerebrovascular disorders and/or disorders of the urogenital system, in particular for the treatment of erectile dysfunction.

7-alkyl- and cycloalkyl-substituted imidazotriazinones

The present invention relates to 7-alkyl- and cycloalkyl-substituted imidazotriazinones, to processes for their preparation and to their use as medicaments, in particular as inhibitors of cGMP-metabolizing phosphodiesterases.

1,6-Dihydro-6-oxo-2-(ortho-substituted phenyl)pyrimidine-5-carboxylic acid derivatives

A series of 1,6-dihydro-6-oxo-2-(ortho-substituted phenyl)pyrimidine-5-carboxylic acid derivatives is provided for use as inhibitors of allergic reactions. The compounds show antiallergy activity by both oral and parenteral routes of administration.