42042-71-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(Isopropylamino)butanol is used as a pharmaceutical intermediate for the synthesis of various drugs, including antihypertensive agents and local anesthetics. Its unique chemical structure allows it to serve as a key component in the development of medications that address cardiovascular and anesthetic needs.
Used in Industrial Applications:
4-(Isopropylamino)butanol is used as a corrosion inhibitor, helping to protect materials from the damaging effects of corrosion, thereby extending their service life and improving their performance in various industrial settings.
Additionally, it is used as a reagent in the production of coatings and adhesives, contributing to the formulation of high-quality products that offer enhanced bonding and protective properties. Its role in these applications underscores its utility in the development of materials with improved performance characteristics.

InChI:InChI=1/C7H17NO/c1-7(2)8-5-3-4-6-9/h7-9H,3-6H2,1-2H3

Upstream product

• 6622-04-4 4-(isopropylamino)-4-oxobutanoic acid 
• 42042-66-0 N-isopropyl-4-hydroxybutyramide 
• 928-51-8 4-Chloro-1-butanol 
• 75-31-0 isopropylamine 
• 13325-10-5 4-Aminobutanol 
• 67-64-1 acetone 

Downstream Products

• 95433-84-4 Diphenylessigsaeure-<2-(isopropyl-<4-chlor-butyl>-amino)-aethylester> 
• 1848-04-0 Benzilsaeure-<<2--aethylester>> 
• 475086-75-0 4-[N-(5,6-diphenylpyrazine-2-yl)-N-isopropylamino]-1-butanol 
• 475086-01-2 Selexipag 
• 96267-69-5 Benzilsaeure-({2-[isopropyl-(4-chlor-butyl)-amino]-aethylester}) 

Relevant academic research and scientific papers

Method for synthesizing 4-isopropylamino-1-butanol

The invention relates to a method for synthesizing 4-isopropylamino-1-butanol. The method includes following steps: feeding isopropylamine, 4-chloro-1-butanol, a reaction solvent and an acid-binding agent in a sealed reactor according to a molar ratio of 10-1:1:0-20:0-5; controlling the temperature to be 30-90 DEG C, carrying out a reaction for 5-48 hours, adding water to obtain a reaction solution, carrying out a series of reaction post-treatment such as rotary evaporation, acid adjustment, washing the reaction product, carrying out alkali adjustment, extraction, drying and suction filtrationon the reaction solution, and performing pressure reduced distillation on the product to obtain 4-isopropylamino-1-butanol. The method has the advantages of readily available raw materials, few reaction steps, mild reaction conditions, few byproducts, simplicity and convenience in operation, recycling of the used organic solvent, less influence on the environment, simple post-treatment, high product purity and yield, and suitableness for industrial production.

INHIBITORS OF PLATELET FUNCTION AND METHODS FOR USE OF THE SAME

Disclosed herein are small molecule inhibitors of platelet function, and methods of using the small molecules to treat diseases, such as platelet hemostasis and thrombosis. In particular, disclosed herein are compounds of Formula (I) and pharmaceutically acceptable salts thereof: wherein the substituents are as described.

METHOD FOR PREPARING 4-ISOPROPYLAMINO-1-BUTANOL

The present invention relates to a preparation method of 4-isopropylamino-1-butanol, in which using cheap and readily available tetrahydrofuran and acetic acid solution of hydrogen bromide as starting materials to prepare a novel intermediate of 4-isopropylamino-1-acetoxyl butane and further obtain the target product. The present invention has advantages of convenient process operations, mild reaction conditions, economical and environment-friendly benefits, and suitability for industrial production to obtain the product with high purity and high yield.

AN IMRPOVED PROCESS FOR THE PREPARATION OF SELEXIPAG OR ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention provides an improved process for Selexipag of formula (I) or its pharmaceutically acceptable salts.

PROCESS FOR THE PREPARATION OF SELEXIPAG AND INTERMEDIATES THEREOF

The present invention provides processes for the preparation of Selexipag compound of formula (1). The present invention also provides processes for the preparation of 4-[(5,6-diphenyl-pyrazin-2-yl)-isopropyl -amino]-butan-1-ol (2), and 4-isopropylamino-butan-1-ol of formula (3), which are intermediates for the synthesis of Selexipag (1 ).

Selexipag: An Oral and Selective IP Prostacyclin Receptor Agonist for the Treatment of Pulmonary Arterial Hypertension

Prostacyclin controls cardiovascular function via activation of the prostacyclin receptor. Decreased prostacyclin production occurs in several cardiovascular diseases. However, the clinical use of prostacyclin and its analogues is complicated by their chemical and metabolic instability. A medicinal chemistry program searched for novel nonprostanoid prostacyclin receptor agonists not subject to these limitations. A compound with a diphenylpyrazine structural core was synthesized. Metabolic stability and agonist potency were optimized through modification of the linear side chain. Compound 12b (MRE-269, ACT-333679) was identified as a potent and highly selective prostacyclin receptor agonist. Replacement of the terminal carboxyl group with an N-acylsulfonamide group yielded parent compound 26a (selexipag, NS-304, ACT-293987), which is orally active and provides sustained plasma exposure of 12b. Compound 26a was developed for the treatment of pulmonary arterial hypertension and shown to reduce the risk of the composite morbidity/mortality end point in a phase 3 event-driven clinical trial.

Reductive hydroxyalkylation/alkylation of amines with lactones/esters

We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides with an excess of DIBAL-H. Different from the reduction of Weinreb amides with DIBAL-H where aldehydes are formed, the reduction of the in situ formed Weinreb amides yielded amines. Moreover, this method is not limited to Weinreb amides, instead, it also works for other amides in general. A plausible mechanism is suggested to account for the outcome of the reactions.

Structure-activity studies on diphenylpyrazine derivatives: A novel class of prostacyclin receptor agonists

To develop nonprostanoid prostacyclin receptor agonists with a high degree of metabolic resistance and an extended duration of action, a novel series of diphenylpyrazine derivatives was synthesized and evaluated for their inhibition of ADP-induced human platelet aggregation. Structure-activity relationship studies on the side chain containing the carboxylic acid moiety of the lead compound 5c showed that the length of the linker and the presence of the concatenating nitrogen atom adjacent to the pyrazine ring are critical for the antiaggregatory activity. This study led to the discovery of 2-amino-5,6-diphenylpyrazine derivatives 8c, 15a, and 15b, which showed potent inhibition of platelet aggregation with IC50 values of 0.2 μM. Among these compounds, 15b is an orally available and long-lasting prostacyclin receptor agonist which is promising for the treatment of various vascular diseases.

HETEROCYCLIC COMPOUND DERIVATIVES AND MEDICINES

The present invention provides a compound which is useful as a PGI2 receptor agonist, and a pharmaceutical composition. The present invention is directed to a pharmaceutical composition comprising a compound represented by the following formula [1]: (R1 and R2 are the same or different and each represents optionally substituted aryl, Y represents N or CH, Z represents N or CH, A represents NH, NR5, O, S, or ethylene, R5 represents alkyl, D represents alkylene or alkenylene, E represents phenylene or single bond, G represents O, S, or CH2, R3 and R4 are the same or different and each represents hydrogen or alkyl, Q represents carboxy, alkoxycarbonyl, tetrazolyl, carbamoyl, or N-(alkylsulfonyl)carbamoyl), or a pharmaceutically acceptable salt thereof as an active ingredient.