104618-33-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole is used as an intermediate in the improved synthesis of pramipexole, an anti-Parkinson drug. Its unique structure allows for the efficient production of pramipexole, which is crucial in the treatment of Parkinson's disease and other movement disorders.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole serves as a valuable building block for the development of new compounds with potential applications in various industries. Its versatile structure enables the creation of a wide range of derivatives, making it a promising candidate for further research and development.

InChI:InChI=1/C15H13N3O2S/c16-15-17-11-6-5-8(7-12(11)21-15)18-13(19)9-3-1-2-4-10(9)14(18)20/h1-4,8H,5-7H2,(H2,16,17)

Upstream product

• 17356-08-0 thiourea 
• 104618-32-8 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 202058-46-6 2-(3-bromo-4-oxocyclohexyl)isoindoline-1,3-dione 
• 99337-98-1 2-((1R,4R)-4-hydroxycyclohexyl) isoindoline-1,3-dione 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 27489-62-9 trans-4-hydroxycyclohexylamine 

Downstream Products

• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 

Relevant academic research and scientific papers

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.

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.

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.

Tetrahydro-benzthiazoles, the preparation thereof and their use as intermediate products or as pharmaceuticals

This invention relates to new tetrahydrobenzthiazoles of general formula STR1 wherein R1 represents a hydrogen atom, an alkyl group, an alkenyl or alkynylk group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the above mentioned phenyl nuclei may each be substituted by 1 or 2 halogen atoms, R2 represents a hydrogen atom or an alkyl group, R3 represents a hydrogen atom, an alkyl group a cycloalkyl group, an alkenyl or alkynyl group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the phenyl nucleus may be substituted by flurorine, chlorine or bromine atoms, R4 represents a hydrogen atom, an alkyl group, an alkyl or alkenyl group, or R3 and R4 together with the nitrogen atom between them represent a pyrrolidino, piperidino, hexamethyleneimino or morpholino group, the enantiomers and the acid addition salts thereof. The compounds of general formula I above in which one of the groups R1 or R3 or both groups R1 and R3 represent an acyl group are valuable intermediate products for preparing the other compounds of general formula I which have valuable pharmacological properties. The new compounds may be prepared using methods known per se.