104632-26-0

Usage

Uses

Used in Neurology:
Pramipexole is used as an antiparkinsonian agent for the treatment of Parkinson's disease (PD). It acts as a partial/full D2S, D2L, D3, and D4 receptor agonist, helping to alleviate the motor symptoms associated with PD by increasing dopamine levels in the brain.
Used in Restless Legs Syndrome Treatment:
Pramipexole is also utilized for the management of restless legs syndrome (RLS), a neurological disorder characterized by an irresistible urge to move the legs, often accompanied by uncomfortable sensations.
Used in Cluster Headache Treatment:
Although used off-label, Pramipexole has been found to be effective in treating cluster headaches, a severe and debilitating form of headache.
Used in Sexual Dysfunction Management:
Pramipexole is sometimes prescribed to counteract sexual dysfunction issues experienced by some users of selective serotonin reuptake inhibitor (SSRI) antidepressants, helping to improve their quality of life.

Originator

Mirapex, Pharmacia and Upjohn, USA

Biological Activity

pramipexole is a dopamine agonist of the non-ergoline class indicated for treating parkinson's disease (pd) and restless legs syndrome (rls).pramipexole also possesses low/insignificant affinity (500-10,000 nm) for the 5-ht1a, 5-ht1b, 5-ht1d, and α2-adren

InChI:InChI=1/C10H17N3S/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8/h7,12H,2-6H2,1H3,(H2,11,13)/t7-/m1/s1

Upstream product

• 104632-25-9 pramipexole dihydrochloride 
• 123-38-6 propionaldehyde 
• 106092-09-5 (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine 
• 540-54-5 1-Chloropropane 
• 106006-80-8 N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)acetamide 
• 123-62-6 propionic acid anhydride 
• 637-88-7 1,4-Cyclohexanedione 
• 107-10-8 propylamine 
• 599-91-7 propyl tosylate 
• 873431-80-2 (S)-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine tartrate trihydrate 
• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 104617-50-7 N-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)acetamide hydrobromide 
• 1046124-81-5 (6S)-N-(2-amino-4,5,6,7-tetrahydrobenzothiazole-6-yl)-2-nitro-N-propylbenzenesulfonamide 
• 68-11-1 mercaptoacetic acid 

Downstream Products

• 191217-81-9 pramipexole dihydrochloride monohydrate 
• 1026084-27-4 (-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(biphenyl-4-yl)piperazin-1-yl)ethanone 
• 1026084-30-9 (-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2-methoxyphenyl)piperazin-1-yl)ethanone 
• 1026084-29-6 (-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-phenylpiperazin-1-yl)ethanone 
• 1026084-33-2 (-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethanone 
• 1202880-74-7 (S)-N₆-propyl-N₆-(2-(4-(4-(pyridin-4-yl)phenyl)piperazin-1-yl)ethyl)-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine 
• 1244656-98-1 (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine 
• 1612146-58-3 (S)-5'-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)-1'-(4-methoxybenzyl)spiro[[1,3]dioxolane-2,3'-indolin]-2'-one 

Related news

Full paperNeuroprotective effects of Pramipexole (cas 104632-26-0) transdermal patch in the MPTP-induced mouse model of Parkinson's disease08/21/2019

Parkinson's disease (PD) is characterized by the selective death of dopaminergic neurons. To avoid inconvenience of frequent administration caused by short half life and recurrence of symptoms such as tremor and bradykinesia incurred by drug elimination, a novel long-acting pramipexole tran...detailed

The adrenergic α2 antagonist atipamezole alters the behavioural effects of Pramipexole (cas 104632-26-0) and increases Pramipexole (cas 104632-26-0) concentration in blood plasma08/20/2019

Pramipexole is a dopaminergic agonist used in Parkinson's disease treatment. It is thought to exert its therapeutic and side effects through actions on dopamine D3 receptors. In a recent study, we found that at doses occupying D3 but not D2 receptors pramipexole reduced locomotion and opera...detailed

Original articleLong-term safety and effectiveness of Pramipexole (cas 104632-26-0) in tetrahydrobiopterin deficiency08/19/2019

Tetrahydrobiopterin (BH4) deficiencies are inherited neuro-metabolic disorders leading to monoamine neurotransmitters deficiency. An individualized replacement therapy with neurotransmitters precursors is necessary to restore dopaminergic and serotoninergic homeostasis. The correction of dopamin...detailed

Pramipexole (cas 104632-26-0) nanocrystals for transdermal permeation: Characterization and its enhancement micro-mechanism08/18/2019

The purpose of the study was to improve transdermal delivery of pramipexole via nanocrystals and investigate the enhancement micro-mechanism. Pramipexole nanocrystals were prepared using wet media milling method and incorporated into carbomer gel. In vitro permeation studies through rabbit ear s...detailed

Relevant academic research and scientific papers

Preparation method of high-purity pramipexole

The invention relates to the technical field of pharmacy, and provides a preparation method of high-purity pramipexole. According to the invention, raceme 2, 6-diamino 4, 5, 6, 7-tetrahydrobenzothiazole is used as an initial raw material, and pramipexole is obtained through a three-step chemical reaction, so the introduction of uncontrollable factors of drug quality is reduced, and the requirements of drug application are better met; the market price of the initial raw materials is low, so that the preparation cost of pramipexole can be greatly reduced; the solvent used in the method is green, environmentally friendly, cheap, easy to obtain and suitable for industrial production, the HPLC purity of the obtained pramipexole can reach 99.86%, and the isomer purity can reach 99.89%.

Preparation method of pramipexole dihydrochloride

The invention relates to a preparation method of pramipexole dihydrochloride in the technical field of medicine preparation. The method includes adding (S)-2,6-diamino-4, 6-diamino-4,5,6,7-tetrahydrobenzothiazole adopted as an initial raw material I together with n-propyl p-toluenesulfonate into a toluene solvent; carrying out N-alkylation by the n-propyl p-toluenesulfonate under the action of analkali and a phase transfer catalyst to generate (S)-2-amino-6-propionamido-4,5,6,7-tetrahydrobenzothiazole (II); and dropwise adding hydrochloric acid for salifying the compound II in toluene to obtain the pramipexole dihydrochloride. According to the method, the n-propyl p-toluenesulfonate is selected as an alkylation reagent, an alkylation reaction of amino is completed in one step to obtain pramipexole, the hydrochloric acid is directly dropwise added into the pramipexole to form the salt without separation, the reaction steps are shortened, and the economic benefits of the product are improved.

Preparation method of pramipexole

The invention discloses a preparation method of pramipexole. The method comprises the following steps: adding (S)-2-amino-6-propionylamino-4,5,6,7-tetrahydrobenzothiazole into tetrahydrofuran, and carrying out a reduction reaction by using a sodium borohydride/boron trifluoride complex, wherein a molar ratio of (S)-2-amino-6-propionylamino-4,5,6,7-tetrahydrobenzothiazole to sodium borohydride to boron trifluoride complex is 1:1:2-1:3:4; and separating to obtain a target product (S)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole. The method provided by the invention has the advantages that the required raw materials are simple and easily available, the reaction conditions are mild, the use amount of the sodium borohydride/boron trifluoride complex is greatly reduced compared with theprior art, the reaction safety is greatly improved while the cost is saved, and the yield and the purity are higher, so that the method is suitable for industrial production.

Pramipexole related compound and preparation method and usage thereof

The invention discloses a pramipexole related compound and a preparation method and a usage thereof. The pramipexole related compound is a compound as shown in a formula (I) or salt thereof. The compound as shown in the formula (I) or the salt thereof can be used as a standard substance (a reference substance) of related substances in pramipexole, and used for controlling quality of a pramipexolecrude drug or preparation.

Preparation method of pramipexole dihydrochloride and intermediate thereof

The invention discloses a preparation method of pramipexole dihydrochloride and an intermediate thereof. The invention provides a preparation of pramipexole II. The preparation method of the pramipexole II comprises the following steps: performing condensation reaction and reduction reaction on a pramipexole intermediate III, propylamine and hydrogen in an organic solvent and under the existence of a chiral catalyst, and performing one-pot method to obtain the pramipexole II. According to the preparation method provided by the invention, the route step is short, chiral resolution is not neededand the total molar yield is high; furthermore, the prepared product has high purity, can reach to the standard of raw material medicines and is suitable for industrialized production. (The formula is shown in the description).

Industrial preparation method for pramipexole and hydrochloride thereof

The invention relates to a preparation method for S-(-)pramipexole. The method comprises the following steps: (1) dissolving S-(-)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole in a mixed solvent, carrying out stirring, adding a basic catalyst and n-propyl p-toluenesulfonate, carrying out heating after completion of addition, then carrying out a stirring reaction, and carrying out filtering and drying after completion of the reaction so as to obtain white S-(-)pramipexole p-toluenesulfonate solid; and (2) adding S-(-)pramipexole p-toluenesulfonate into an aqueous solution of salt, adding an inorganic base under stirring, carrying out stirring at room temperature after completion of addition, and carrying out filtering and drying so as to obtain a white S-(-)pramipexole solid, wherein no organic solvent is used in the step (2).

Synthesis method of high-purity pramipexole

The invention discloses a synthesis method of high-purity pramipexole, which includes the steps of: 1) an acylation reaction; 2) crystallization; 3) preparation of an intermediate; 4) a reduction reaction; 5) extraction and purification; 6) reflux decolorization; and 7) recrystallization. In the method, through the acylation reaction then the reduction reaction, reaction efficiency of a raw material, S-(-)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole, is increased, thereby increasing the yield of the pramipexole; and through operations of decolorization, extraction, recrystallization and the like, purity and quality of the pramipexole are increased effectively. The method has gentle and controllable reaction conditions, is simple in operations in crystallization, recrystallization and purification steps and has high practicability. The pramipexole is high in yield and purity, is low in impurity content and has great market prospect.

Convenient N-Alkylation of amines using an effective magnetically separable supported ionic liquid containing an anionic polyoxometalate

Abstract: An effective synthesis of anion-exchanged supported ionic liquid using magnetically separable nanoparticles and its catalytic effect on N-alkylation reactions is described. Anionic polyoxometalate derivative was used in the anion-exchange step in catalyst design. The catalytic system can be easily separated from the reaction mixture with external magnetic field and recycled in subsequent reactions. In order to evaluate catalyst repeatability, N-alkylation of some more amines such as Aniline, 4-aminobenzenesulfonamide, 4-methoxyaniline, 2-aminopyrimidin and 4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine in the presence of recoverable catalyst was successfully examined in this article. In addition, pramipexole dihydrochloride as an active pharmaceutical ingredient was successfully synthesized using the catalytic system. The structure of catalyst was determined by infrared spectroscopy, X-ray powder diffraction, and scanning electron microscope techniques. The structure of organic products was determined by 1H NMR, 13C NMR, infrared and Mass spectroscopy. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis method of pramipexole hydrochloride intermediate

The invention discloses a synthesis method of a pramipexole hydrochloride intermediate, wherein the method comprises the following steps: under the protection of inert gas, carrying out a contact reaction of (S)-2-amino-6-aminopropyl-4,5,6,7-tetrahydrobenzothiazole with NaBH4 and a solid super-strong acid in a reaction solvent to generate the pramipexole hydrochloride intermediate. In the synthesis method of the pramipexole hydrochloride intermediate, use of flammable and explosive reducing agents such as borane, lithium aluminum hydride, red aluminum and the like is avoided, and thus the process is safe; moreover, the used solid super-strong acid can be recycled and reused, so the cost is reduced; and the synthesis method has important application value.

AN IMPROVED PROCESS FOR THE PREPARATION OF PRAMIPEXOLE DIHYDROCHLORIDE MONOHYDRATE

The present invention relates to an improved process for the preparation of the dihydrochloride monohydrate salt of (S)-2-amino-4,5,6,7-tetrahydro-6- (propylamino)benzothiazole (the compound of formula I) comprising reacting the compound of formula II with n-propanal and sodium borohydride using a mixture of methanol and dichloromethane (DCM) as the solvent to obtain the compound of formula I; followed by converting the compound of formula I into its monohydrochloride salt; purifying the monohydrochloride salt of the compound of formula I; and finally converting the pure monohydrochloride salt of the compound of formula I into the dihydrochloride monohydrate salt.