cas 106092-09-5, (S)-4,5,6,7-Tetrahydro-2,6-benzothiazolediamine

Articles about 106092-09-5Total 15 be found

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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%.
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Paragraph 0059-0061; 0068-0070

(2021/04/07)

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.
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Paragraph 0023; 0028-0029; 0034-0035; 0040-0041; 0050

(2020/03/25)

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.
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Paragraph 0023-0042

(2020/01/25)

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).
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Paragraph 0086; 0089

(2018/08/04)

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)
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Paragraph 0057; 0059-0062

(2017/12/27)

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.
Toma?i?, Tihomir,Katsamakas, Sotirios,Hodnik, ?iga,Ila?, Janez,Brvar, Matja?,Solmajer, Tom,Montalv?o, Sofia,Tammela, P?ivi,Banjanac, Mihailo,Ergovi?, Gabrijela,Anderluh, Marko,Ma?i?, Lucija Peterlin,Kikelj, Danijel
supporting information
p. 5501 - 5521
(2015/08/03)

Baker's yeast catalyzed preparation of a new enantiomerically pure synthon of (S)-pramipexole and its enantiomer (dexpramipexole) This work is dedicated to Professor Enzo Santaniello in the year of his 70th birthday
A biocatalyzed reduction of a prochiral bicyclic ketone afforded enantiomerically pure (R)-2-acetylamino-6-hydroxy-4,5,6,7-tetrahydrobenzothiazole, a synthon of the anti-Parkinson (S)-pramipexole and its (R)-isomer, which is currently under investigation for the treatment of amyotrophic lateral sclerosis (ALS).
Ferraboschi, Patrizia,Ciceri, Samuele,Ciuffreda, Pierangela,De Mieri, Maria,Romano, Diego,Grisenti, Paride
p. 1239 - 1245
(2015/02/19)

IMPROVED PROCESS FOR THE PREPARATION OF (S)-2-AMINO-4,5,6,7-TETRAHYDRO-6 - (PROPYLAMINO) BENZOTHIAZOLE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
The present invention relates to an improved process for the preparation of of (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole and its pharmaceutically acceptable salts. Specifically relates to the compound represented by the following structural formula- Ia.
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(2011/04/13)

Synthesis and identification of a new class of (S)-2,6-diamino-4,5,6,7- tetrahydrobenzo[d]thiazole derivatives as potent antileukemic agents
Benzothiazoles are multitarget agents with broad spectrum of biological activity. Among the antitumor agents discovered in recent years, the identification of various 2-(4-aminophenyl) benzothiazoles as potent and selective antitumor drugs against different cancer cell lines has stimulated remarkable interest. Some of the benzothiazoles are known to induce cell cycle arrest, activation of caspases and interaction with DNA molecule. Based on these interesting properties of benzothiazoles and to obtain new biologically active agents, a series of novel 4,5,6,7-tetrahydrobenzo[d]thiazole derivatives 5(a-i) were synthesized and evaluated for their efficacy as antileukemic agents in human leukemia cells (K562 and Reh). The chemical structures of the synthesized compounds were confirmed by 1H NMR, LCMS and IR analysis. The cytotoxicity of these compounds were determined using trypan blue exclusion, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assays. Results showed that, these compounds mediate a significant cytotoxic response to cancer cell lines tested. We found that the compounds having electron withdrawing groups at different positions of the phenyl ring of the thiourea moiety displayed significant cytotoxic effect with IC50 value less than 60 μM. To rationalize the role of electron withdrawing group in the induction of cytotoxicity, we have chosen molecule 5g (IC 50 ～15 μM) which is having chloro substitution at ortho and para positions. Flow cytometric analysis of annexin V-FITC/propidium iodide (PI) double staining and DNA fragmentation suggest that 5g can induce apoptosis. Springer Science + Business Media, LLC 2009.
Prasanna,Kavitha,Raghava,Vinaya,Ranganatha,Raghavan, Sathees C.,Rangappa
scheme or table
p. 454 - 465
(2011/12/04)

RHO KINASE INHIBITORS
Substituted amide and urea derivatives useful as inhibitors of Rho kinase are described, which inhibitors can be useful in the treatment of various disorders such as cardiovascular diseases, cancer, neurological diseases, renal diseases, bronchial asthma, erectile dysfunction and glaucoma.
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Page/Page column 142-144

(2008/12/07)

PROCESS FOR PREPARING (S)-PRAMIPEXOLE AND ITS INTERMEDIATES
The present invention relates to an improved process for the preparation of (S)- 2,6-diamino-4,5,6,7-tetrahydrobenzothiazole of formula (II) useful in the preparation of pramipexole or (S)-2,6-amino-6-(n-propylamino)-4,5,6,7-tetrahydrobenzothiazole of formula (I) and its pharmaceutically acceptable salts or solvates thereof. The present invention further provides a process for the preparation of Pramipexole and its pharmaceutically acceptable salts, hydrates, solvates thereof.
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Page/Page column 18

(2008/06/13)

IMPROVED PROCESS FOR THE PREPARATION OF BIOLOGICALLY ACTIVE TETRAHYDROBENZTHIAZOLE DERIVATIVE
Improved process for the preparation of the intermediate compound of formula II for formation pramipezole of formula (I) as well as the biological active tetrahydrobenzothiazole compound of formula (I) and/or its pharmaceutically acceptable salts or solvates.
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Page/Page column 10; 18

(2008/06/13)

PROCESS FOR PREPARING CHIRALLY PURE 2-AMINO-6-(ALKYL)AMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOLES BY LIQUID CHROMATOGRAPHIC RESOLUTION
Processes for obtaining single enantiomers of 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazoles by liquid chromatography are disclosed.
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Page/Page column 16-17

(2008/06/13)

Novel thrombin inhibitors incorporating weakly basic heterobicyclic P1-arginine mimetics: optimization via modification of P1 and P3 moieties.
Optimization of lead compounds 1 and 2 resulted in novel, selective, and potent thrombin inhibitors incorporating weakly basic heterobicyclic P(1)-arginine mimetics. The design, synthesis, and biological activity of racemic thrombin inhibitors 17-29 and enantiomerically pure thrombin inhibitors 30-33 are described. The arginine side-chain mimetics used in this study are 4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine, 4,5,6,7-tetrahydro-2H-indazole, and 2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-ylamine.
Krajnc, Andreja,Peterlin-Masic, Lucija,Ilas, Janez,Prezelj, Andrej,Stegnar, Mojca,Kikelj, Danijel
p. 3251 - 3256
(2007/10/03)

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.
Schneider, Claus S.,Mierau, Joachim
p. 494 - 498
(2007/10/02)