330786-34-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Pyrimidinecarboxylic acid, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-(methylthio)is used as a potential drug candidate for the development of new medications due to its unique structure and functional groups that may interact with biological targets, such as receptors or enzymes.
Used in Medicinal Chemistry Research:
5-Pyrimidinecarboxylic acid,
4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-(methylthio)is utilized in medicinal chemistry research to explore its potential interactions with biological targets and to investigate its efficacy and safety in treating various diseases or conditions.
Used in Drug Development:
5-Pyrimidinecarboxylic acid, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-(methylthio)is employed in drug development processes to create new pharmaceuticals that can target specific receptors or enzymes, potentially leading to more effective treatments for various health issues.

Upstream product

• 41965-95-1 (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride 
• 53554-29-3 ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate 
• 115514-77-7 (3-chloro-4-methoxyphenyl)methanamine 
• 5909-24-0 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester 
• 330785-81-4 ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate 

Downstream Products

• 372113-63-8 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyridylmethyl)carbamoyl]pyrimidine 
• 330784-22-0 (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(pyridin-2-ylmethyl)carbamoyl]pyrimidine 
• 330784-47-9 avanafil 
• 330785-86-9 4-(3-Chloro-4-methoxy-benzylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde 
• 330785-87-0 4-(3-Chloro-4-methoxy-benzylamino)-2-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-pyrimidine-5-carbaldehyde 
• 330784-23-1 (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine 
• 372114-66-4 [4-(3-Chloro-4-methoxy-benzyl)-2-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-pyrimidin-5-yl]-pyridin-2-yl-methanone 
• 330785-94-9 1-[4-(3-Chloro-4-methoxy-benzylamino)-2-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-pyrimidin-5-yl]-propenon 
• 372113-70-7 [4-(3-Chloro-4-methoxy-benzylamino)-2-methylsulfanyl-pyrimidin-5-yl]-(1-methyl-1H-imidazol-2-yl)-methanone 

Relevant academic research and scientific papers

Method for synthesizing avanafil impurities

The invention discloses a method for synthesizing avanafil impurities, which belongs to the field of drug synthesis and has the advantages of reasonable process design, strong operability and mild reaction conditions. The preparation method comprises the following steps: A. hydrolyzing 4-(3-chlorine-4-methoxy phenylamino)-5-ethoxy carbonyl-2-methylthio pyrimidine I serving as a raw material in the presence of alkali to obtain a compound II; B, condensing the compound II and 2-aminomethylpyrimidine hydrochloride III under an alkaline condition to obtain a compound IV; C, oxidizing the compound IV in the presence of an oxidant to obtain a compound V; and D, reacting the compound V under an alkaline condition to obtain the avanafil impurity VI. According to the avanafil impurity prepared by the method, the impurity spectrum of avanafil is perfected, an important basis is provided for quality research of avanafil, and the safety of avanafil is further improved through research and control of the impurity.

Preparation method of avanafil

The invention provides a preparation method of avanafil, and specifically relates to the technical field of pharmaceutical chemistry. The preparation method of avanafil comprises the following steps:sequentially carrying out cyclization and chlorination reactions on methyl thiourea sulfuric acid and diethyl ethoxymethylene malonate which serve as initial raw materials to obtain 4-chloro-2-methylthiopyrimidine-5-carboxylic acid ethyl ester; then substituting and hydrolyzing with 3-chloro-4-methoxybenzylamine; condensing with 2-pyrimidinemethanamine to obtain a key intermediate, namely, 4-[(3-chloro-methoxybenzyl)amino]-2-methylthio-N-(2-pyrimidine methyl)-5-pyrimidine formamide; oxidizing the intermediate and reacting with L-prolinol to generate the avanafil. The preparation method has theadvantages of easy availability of raw materials, easiness and convenience in operation, mild reaction conditions and higher product yield.

Atorvastatin that non-synthetic method

The invention provides a synthesis method of avanafil. The synthesis method of avanafil comprises the following steps: carrying out nucleophilic substitution reaction with a compound (13) or a compound (3) by a compound (18), hydrolyzing to prepare a compound (21) or a compound (22), reacting the compound (21) or the compound (22) with sulfonic acid chloride or pivaloyl chloride to obtain mixed anhydride, reacting the mixed anhydride with a compound (23) to prepare a compound (24) or a compound (25), then oxidizing the compound (24), subsequently reacting the compound (24) with a compound (9) to prepare avanafil, or directly reacting the compound (25) with the compound (9) to prepare avanafil. The synthesis method is high in controllability, simple in step, high in yield and low in cost, and is suitable for industrial production. The reaction route is shown in the description.

A process for the preparation of atorvastatin that non-intermediate and its preparation method

The invention provides a novel intermediate IV which is used for preparation of avanafil. The intermediate has a general formula IV as described in the specification; and in the general formula IV, R represents a C1-20 alkylsulfinyl group or a C1-20 alkylsulfonyl group. The intermediate has high purity, is suitable for industrial production and can be subjected to a one-step chemical reaction to prepare avanafil. The invention also provides a preparation method for the intermediate and a method for preparing avanafil from the intermediate.

BICYCLIC SUBSTITUTED PYRIMIDINE COMPOUNDS

The present invention relates to the technical field of medicine and pharmacy, and particularly relates to bicyclic group substituted pyrimidine compounds represented by general formula (I), pharmaceutical acceptable salts thereof or stereoisomers thereof, wherein R1, R2, R3, R4, R5 and R6 are as defined in the specification. The present invention also relates to preparation methods, pharmaceutical formulations, and pharmaceutical compositions of the compounds, and use of the compounds, pharmaceutical formulations, and pharmaceutical compositions for preparing a medicament for treating and/or preventing sexual dysfuntion diseases and diseases with lower urinay tract symptoms.

8-(3-Chloro-4-methoxybenzyl)-8H-pyrido[2,3-d]pyrimidin-7-one derivatives as potent and selective phosphodiesterase 5 inhibitors

A novel series of highly selective phosphodiesterase 5 (PDE5) inhibitors was found. 8H-Pyrido[2,3-d]pyrimidin-7-one derivatives bearing an (S)-2-(hydroxymethyl)pyrrolidin-1-yl group at the 2-position and a 3-chloro-4-methoxybenzyl group at the 8-position

A PROCESS FOR THE PREPARATION OF AVANAFIL AND ITS NOVEL INTERMEDIATES

The present invention relates to a novel compound of Formula (II), and its use in preparation of Avanafil, [Formula should be inserted here] wherein R is -OH, -CI or -OR1 and R1 is C1 to C3 alkyl group.

The discovery of avanafil for the treatment of erectile dysfunction: A novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor

Novel pyrimidine-5-carboxamide derivatives bearing a 3-chloro-4-methoxybenzylamino group at the 4-position were identified as potent and highly selective phosphodiesterase 5 inhibitors. Among them, we successfully found 10j (avanafil) which exhibited a potent relaxant effect on isolated rabbit cavernosum (EC30 = 2.1 nM) and a high isozyme selectivity.

Cyclic compounds

1. A cyclic compound of the formula (I) or a pharmacologically acceptable salt thereof, wherein X is ═CH— or ═N—, Y is —NH—, —NR4—, —S—, —O—, —CH═N—, —N═CH—, —N═N—, —CH═CH—, etc., R1 is a lower alkoxy group, an amino group, a heterocyclic ring containing N atom(s), or a hydroxy group substituted by a heterocyclic ring containing N atom(s) (each of which is optionally substituted), R2 is a lower alkylamino group which is optionally substituted by an aryl group, a lower alkoxy group which is optionally substituted by an aryl group, a lower alkoxy group substituted by an aromatic heterocyclic ring containing N atom(s), R3 is an aryl group, a heterocyclic ring containing N atom(s), a lower alkyl group, a lower alkoxy group, a cyclo lower alkoxy group, a hydroxy group substituted by a heterocyclic ring containing N atom(s), or an amino group (each of which is optionally substituted), and R3 and a substituent in Y may be combined to form a lactone ring. The compound of the present invention has excellent selective PDE V inhibitory activity and therefore, is useful as a therapeutic or prophylactic drug for treating various diseases due to functional disorders on cGMP-signaling.

Aromatic nitrogen-containing 6-membered cyclic compounds

An aromatic nitrogen-containing 6-membered cyclic compound of the formula (I): wherein Ring A is a substituted or unsubstituted nitrogen-containing heterocyclic group; R1 is a substituted or unsubstituted lower alkyl group, —NH—Q—R3 (R3 is a substituted or unsubstituted nitrogen containing heterocyclic group, and Q is a lower alkylene group or a single bond), or —NH—R4 (R4 is a substituted or unsubstituted cycloalkyl group); R2 is a substituted or unsubstituted aryl group; one of Y and Z is ═CH—, and the other is ═N—, or a pharmaceutically acceptable salt thereof, these compounds exhibiting excellent selective PDE V inhibitory activities, and hence, being useful in the prophylaxis or treatment of penile erectile dysfunction, etc.