182133-35-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxybenzo[b]thiophene-2-boronic acid is used as a key reactant in the synthetic preparation of diaminobenzo[b]thiophenes, which are important active site directed thrombin inhibitors and anticoagulants. These compounds play a crucial role in the development of novel antithrombotic drugs, offering potential therapeutic benefits for the treatment and prevention of blood clot-related disorders.
In the synthesis of diaminobenzo[b]thiophenes, 6-Methoxybenzo[b]thiophene-2-boronic acid serves as a versatile building block, allowing for the introduction of various functional groups and structural modifications. This enables the fine-tuning of the physicochemical properties and biological activities of the resulting thrombin inhibitors, leading to the discovery of more potent and selective antithrombotic agents.
Furthermore, the boronic acid moiety in 6-Methoxybenzo[b]thiophene-2-boronic acid can participate in various coupling reactions, such as Suzuki-Miyaura cross-coupling, providing a convenient and efficient method for the synthesis of diverse diaminobenzo[b]thiophene derivatives with tailored pharmacological profiles.
Overall, 6-Methoxybenzo[b]thiophene-2-boronic acid is a valuable intermediate in the pharmaceutical industry, contributing to the advancement of thrombin inhibitors and anticoagulant drug development. Its unique structural features and synthetic utility make it an attractive candidate for further research and application in the field of medicinal chemistry.

Upstream product

• 90560-10-4 6-methoxy-benzo[b]thiophene 
• 5419-55-6 Triisopropyl borate 
• 15570-12-4 3-methoxybenzenethiol 

Downstream Products

• 193964-15-7 6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene 
• 92014-01-2 2-phenyl-6-methoxybenzothiophene 
• 414861-54-4 6-methoxy-2-(4-methoxy-2-methyl-phenyl)-benzo[b]thiophene 
• 414861-53-3 1-[2-methoxy-5-(6-methoxy-benzo[b]thiophen-2-yl)-phenyl]-ethanone 
• 414861-51-1 2-(3,4-dimethoxy-phenyl)-6-methoxy-benzo[b]thiophene 
• 414861-48-6 6-methoxy-2-(4-methoxy-3-methylphenyl)-benzo[b]thiophene 
• 215378-95-3 6-Methoxy-2-(4-nitrophenyl)benzo [b]thiophene 
• 193966-25-5 N-[4-(6-Methoxybenzo[b]thiophen-2-yl)phenyl]-α-(1-pyrrolidinyl)acetamide 
• 63675-74-1 2-(4'-methoxyphenyl)-6-methoxybenzothiophene 
• 1097776-64-1 ethyl 4-[6-(methyloxy)-1-benzothien-2-yl]benzoate 
• 1610886-26-4 (6-methoxy-2-(5'-methoxypyridin-2'-yl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone 
• 1610886-00-4 (4-fluorophenyl)(6-methoxy-2-(5-methoxypyridin-2-yl)benzo[b]thiophen-3-yl)methanone 
• 182133-36-4 [6-methoxy-2-(4-methanesulfonyloxy-phenyl)]benzo[b]thiophene 
• 193966-62-0 3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone 

Relevant academic research and scientific papers

2-ARYLBENZOTHIOPHENE DERIVATIVES OR PHARCEUTICALLY ACCEPTABLE SALTS THEREOF, PREPARATION METHOD THEREOF, AND PHARCEUTICAL COMPOSITION FOR THE DIAGNOSIS OR TREATMENT OF DEGENERATIVE BRAIN DISEASE CONTAINING THE SAME AS ACTIVE INGREDIENT

2-arylbenzothiophene derivatives or pharmaceutically acceptable salts thereof, a preparation method thereof, and a pharmaceutical composition for the diagnosis or treatment of degenerative brain disease containing the same as an active ingredient. Since the 2-arylbenzothiophene derivatives of Formula 1 have a relatively high binding affinity for β-amyloid, they can be used as diagnostic reagents for diagnosing Alzheimer's disease at an early stage by non-invasive techniques when they are labeled with radioisotopes: wherein R1-R4, V, W, X, Y and Z are as defined in the Detailed Descript of the specification. Further, when the pharmaceutical composition containing the 2-arylbenzothiophene derivative binds with a low-molecular weight β-amyloid peptide binding compound, generation of malignant high-molecular weight β-amyloid deposits is minimized. Accordingly, the pharmaceutical composition can be used as a therapeutic agent of degenerative brain disease such as Alzheimer's disease.

FARNESOID X RECEPTOR AGONISTS

The present invention relates to famesoid X receptors (FXR, NR1H4) FXR is a member of the nuclear receptor class of ligand-activate transcription factors More particularly, the present invention relates to compounds useful as agonists for FXR, pharmaceutical formulations comprising such compounds, and therapeutic use of the same Novel isoxazole compounds are disclosed as part of pharmaceutical compositions for the treatment of a condition mediated by decreased FXR activity, such as obesity, diabetes, cholestatic liver disease, liver fibrosis, and metabolic syndrome

Antithrombotic agents

This application relates to novel compounds of formula (I) (and their pharmaceutically acceptable salts), as defined herein, processes and intermediates for their preparation, pharmaceutical formulations comprising the novel compounds of formula (I), and the use of the compounds of formula (I) as thrombin inhibitors.

Toward selective ERβ agonists for central nervous system disorders: Synthesis and characterization of aryl benzthiophenes

In an effort to identify selective for the estrogen receptor subtype ERβ, a series of aryl benzthiophenes was synthesized. In a radioligand binding assay and reporter gene assat in HeLa and SH-SY5Y cells, compound were characterized as ERβ-selective agonists. By targeting ERβ in the brain, these compounds could lead to drugs able to separate the beneficial effects of estrogens on mood, learning, and memory from side effects such as the stimulation of edometrial and breast cancer.

Thrombin inhibitors

This application relates to novel compounds of formula I (and their pharmaceutically acceptable salts), as defined herein, processes and intermediates for their preparation, pharmaceutical formulations comprising the novel compounds of formula I, and the use of defined compounds of formula I as thrombin inhibitors.

Diamino benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 5. Potency, efficacy, and pharmacokinetic properties of modified C-3 side chain derivatives

A systematic investigation of the structure-activity relationships of the C-3 side chain of the screening hit la led to the identification of the potent thrombin inhibitors 23c, 28c, and 31c. Their activities (1240, 903, and 1271 x 106 L/mol, respectively) represent 2200- and 2900-fold increases in potency over the starting lead la. This activity enhancement was accomplished with an increase of thrombin selectivity. The in vitro anticoagulant profiles of derivatives 28c and 31c were determined, and they compare favorably with the clinical agent H-R-1-[4aS,- 8aS]perhydroisoquinolyl-prolyl-arginyl aldehyde (D-Piq-Pro-Arg-H; 32). The more potent members of this series have been studied in an arterial/venous shunt (AV shunt) model of thrombosis and were found to be efficacious in reducing clot formation. However, their efficacy is currently limited by their rapid and extensive distribution following administration.

Antithrombotic diamines

This application relates to the use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents of diamines of formula I as defined herein. It also provides novel compounds of formula I, processes and intermediates for their preparation, and pharmaceutical formulations comprising the novel compounds of formula I.

Treatment of central nervous system disorders with selective estrogen receptor modulators

The present invention provides a method of treating depression, mood swings, or Alzheimer's disease in a patient in need of such treatment by administering a selective estrogen receptor modulating compound of the formula in which R1 and R2 are independently hydroxy and alkoxy of one to four carbon atoms; and R3 and R4 are independently methyl or ethyl, or R3 and R4, taken together with the nitrogen atom to which they are attached, form a pyrrolidino, methyl-pyrrolidino, dimethylpyrrolidino, piperidino, morpholino, or hexamethyleneimino ring.

Benzothiophene compounds, intermediates, compositions, and methods

The present invention provides intermediate compounds and processes for the preparation of compounds of formula I STR1 wherein R1a is --H or --OR7a in which R7a is --H or a hydroxy protecting group; R2a is --H, halo, or --OR8a in which R8a is --H or a hydroxy protecting group; R3 is 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; n is 2 or 3; and Z is --O-- or --S--; or a pharmaceutically acceptable salt thereof.

Method of treating estrogen dependent cancers

A method for alleviating the symptoms of post-menopausal syndrome comprising administering to a woman in need thereof an effective amount of a compound of formula I STR1 wherein R1a is --H or --OR7a in which R7a is --H or a hydroxy protecting group; R2a is --H, halo, or --OR8a in which R8a is --H or a hydroxy protecting group; R3 is 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; n is 2 or 3; and Z is --O-- or --S--; or a pharmaceutically acceptable salt thereof.