104617-49-4

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs targeting specific receptors or enzymes in the body.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole serves as a building block for the creation of more complex molecules with diverse applications. Its reactivity and functional groups make it a valuable precursor in organic chemistry.
Used in Material Science:
The compound may also find applications in material science, where its unique structure could be utilized to develop new materials with specific properties, such as improved conductivity, stability, or reactivity.
Used in Research and Development:
2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole is used as a research compound for studying its chemical properties, reactivity, and potential applications in various fields. It can be a valuable tool for scientists to understand the behavior of similar compounds and develop new strategies for their synthesis and application.

InChI:InChI=1/C7H11N3S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h4H,1-3,8H2,(H2,9,10)

Upstream product

• 104618-33-9 2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)isoindoline-1,3-dione 
• 17356-08-0 thiourea 
• 27489-62-9 trans-4-aminocyclohexan-1-ol 
• 766508-72-9 2-bromo-4-aminocyclohexanone 
• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 106006-80-8 N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)acetamide 
• 23363-88-4 trans-N-acetyl-4-hydroxycyclohexylamine 
• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 
• 1315483-31-8 2,6-diamino-4,5,6,7-tetrahydro benzothiazole, (S)-tartarate salt 
• 104617-50-7 N-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)acetamide hydrobromide 
• 687639-03-8 2-bromo-4-acetamidocyclohexanone 
• 404892-23-5 2-Acetylamino-6-oxo-4,5,6,7-tetrahydrobenzothiazole 
• 159015-33-5 2-amino-6-(ethylenedioxy)-4,5,6,7-tetrahydrobenzothiazole 
• 144810-01-5 1,4-cyclohexanedione-1-ethylene acetal 4-trimethylsilyl enol ether 

Downstream Products

• 106092-11-9 (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine 
• 104632-28-2 (R)-(+)-pramipexole 

Relevant academic research and scientific papers

Dopamine autoreceptor agonists: Resolution and pharmacological activity of 2,6-diaminotetrahydrobenzothiazole and an aminothiazole analogue of apomorphine

The enantiomers of the aminothiazole analogues of the known dopaminergic agonists apomorphine (1) and 2-aminohydroxytetralin (2) have been prepared. The absolute configurations of the enantiomers of 2,6-diaminotetrahydrobenzothiazole have been established by X-ray crystallographic analysis. Dopamine (DA) autoreceptor agonist activities of the compounds were evaluated. Testing revealed (-)-5, the S enantiomer, to be the most active compound tested (inhibition of GBL accelerated dopamine synthesis and inhibition of α-methyltyrosine-induced decline of DA). In addition (-)-5 does not exhibit stereotyped behavior, suggesting a pronounced selectivity for DA autoreceptors.

Discovery of 4,5,6,7-Tetrahydrobenzo[1,2- d ]thiazoles as Novel DNA Gyrase Inhibitors Targeting the ATP-Binding Site

Bacterial DNA gyrase and topoisomerase IV are essential enzymes that control the topological state of DNA during replication and validated antibacterial drug targets. Starting from a library of marine alkaloid oroidin analogues, we identified low micromolar inhibitors of Escherichia coli DNA gyrase based on the 5,6,7,8-tetrahydroquinazoline and 4,5,6,7-tetrahydrobenzo[1,2-d]thiazole scaffolds. Structure-based optimization of the initial hits resulted in low nanomolar E. coli DNA gyrase inhibitors, some of which exhibited micromolar inhibition of E. coli topoisomerase IV and of Staphylococcus aureus homologues. Some of the compounds possessed modest antibacterial activity against Gram positive bacterial strains, while their evaluation against wild-type, impA and ΔtolC E. coli strains suggests that they are efflux pump substrates and/or do not possess the physicochemical properties necessary for cell wall penetration. Our study provides a rationale for optimization of this class of compounds toward balanced dual DNA gyrase and topoisomerase IV inhibitors with antibacterial activity.

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%.

Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R

Even today, the role of the histamine H2 receptor (H2R) in the central nervous system (CNS) is widely unknown. In previous research, many dimeric, high-affinity and subtype-selective carbamoylguanidine-type ligands such as UR-NK22 (5, pKi = 8.07) were reported as H2R agonists. However, their applicability to the study of the H2R in the CNS is compromised by their molecular and pharmacokinetic properties, such as high molecular weight and, consequently, a limited bioavailability. To address the need for more drug-like H2R agonists with high affinity, we synthesized a series of monomeric (thio)carbamoylguanidine-type ligands containing various spacers and side-chain moieties. This structural simplification resulted in potent (partial) agonists (guinea pig right atrium, [35S]GTPγS and β-arrestin2 recruitment assays) with human (h) H2R affinities in the one-digit nanomolar range (pKi (139, UR-KAT523): 8.35; pKi (157, UR-MB-69): 8.69). Most of the compounds presented here exhibited an excellent selectivity profile towards the hH2R, e.g. 157 being at least 3800-fold selective within the histamine receptor family. The structural similarities of our monomeric ligands to pramipexole (6), a dopamine receptor agonist, suggested an investigation of the binding behavior at those receptors. The target compounds were (partial) agonists with moderate affinity at the hD2longR and agonists with high affinity at the hD3R (e.g. pKi (139, UR-KAT523): 7.80; pKi (157, UR-MB-69): 8.06). In summary, we developed a series of novel, more drug-like H2R and D3R agonists for the application in recombinant systems in which either the H2R or the D3R is solely expressed. Furthermore, our ligands are promising lead compounds in the development of selective H2R agonists for future in vivo studies or experiments utilizing primary tissue to unravel the role and function of the H2R in the CNS.

Crystallization process of diamino -4, 5, 6, 7- tetrahydrobenzothiazole

Reaction and formation, of the product, with acetone as a reaction solvent, takes place in acetone as a reaction solvent to give the product, as a raw material, with acetone as a reaction solvent to obtain the mixed rotation product, and then recrystallize the reaction solvent with water: to obtain the reaction . Example, shows that the reaction time, is greatly shortened by taking the product, as a reaction solvent by taking acetone as a reaction solvent as a raw material A; dropwise to obtain the reaction and the reaction of the reaction, solvent with water and dissolving: dropwise with acetone as a reaction solvent in step A as a reaction solvent in an existing production process by, acetone, L - taking acetone as a, reaction solvent to prepare a reaction solvent for, the whole process, to prepare a crystal, by taking acetone as, a reaction solvent to prepare a reaction solvent by taking acetone as a reaction solvent to prepare a. reaction solvent by taking acetone as a reaction solvent.

Alkali separation method of (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole * L-tartrate

The invention relates to an alkali precipitation method of (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole * L-tartrate, water is used as a solvent, and a mixed aqueous solution of sodium hydroxide and potassium hydroxide is dropped into an aqueous solution of (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole * L-tartrate to precipitate (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole. The method hasthe advantages that (1) the blazing slag residue of the obtained product can be reduced, and the quality level of the product is improved; (2) the amount of the reaction solvent water is reduced, thereby reducing the discharge amount of waste water and being beneficial to environmental protection; (3) Because the (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole is soluble in water, the loss of theproduct is reduced and the yield of the product is also improved after the amount of water is reduced.

Industrial preparation method of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole

The invention discloses a preparation method of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole suitable for industrial production, wherein 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole is prepared by using p-acetamido cyclohexanone as a raw material through a one-pot method. According to the method, liquid bromine and acetic acid are not used in the production and preparation process, the 6-acetamido-2-amino-4,5,6,7-tetrahydro-benzothiazole can be prepared through a one-pot method, post-treatment operation is easy and convenient, the labor cost is saved, and the production cost is greatly reduced. The 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole prepared by the method is high in yield, good in purity and suitable for industrial production.

Preparation method of pramipexole intermediate 2, 6-diamino-4, 5, 6, 7-tetrahydrobenzothiazole

The invention discloses a preparation method of pramipexole intermediate 2, 6-diamino-4, 5, 6, 7-tetrahydrobenzothiazole. According to the method, 4-acetamido cyclohexanol is taken as a starting material, hydrobromic acid is taken as an oxidizing agent an

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).

A preparation method of pramipexole hydrochloride (by machine translation)

The invention discloses a method for preparation of pramipexole hydrochloride, comprises the following steps: 1) in the organic solvent, in order to 2, 6 - diamino - 4, 5, 6, 7 - tetrahydrobenzo and thiazole as the raw material, to join the resolving agent, heating to reflux, cooling, filtering, basified, make the (-) - (6 s) - 2, 6 - diamino 4, 5, 6, 7 - tetrahydrobenzo and thiazole; 2) in ethanol solution, the (-) - (6 s) - 2, 6 - diamino 4, 5, 6, 7 - tetrahydrobenzo and thiazole, and c anhydride reaction, by heating to reflux, to obtain (-) - (6 s) - 2 - amino - 6 - propionyl amino - 4, 5, 6, 7 - tetrahydrobenzo and thiazole; 3) (-) - (6 s) - 2 - amino - 6 - propionyl amino - 4, 5, 6, 7 - tetrahydrobenzo and thiazole in toluene solution in red aluminum reduction reaction, by heating to reflux, stirring, after devitrifying, make the use of pramipexole; the pramipexole into the isopropyl alcohol solution, by stirring, after devitrifying, react with hydrochloric acid, by decompression, drying, hydrochloride pramipexole. The preparation method is reaction low requirements on the equipment, the pramipexole prepared hydrochloric acid content is high, high purity, high solubility, the output is high, there is little impurity. (by machine translation)