134135-41-4

Usage

Uses

Used in Pharmaceutical Industry:
5-(Bromomethyl)thiophene-2-carbonitrile is used as an intermediate chemical for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medical treatments.
Used in Dye Production:
In the chemical industry, 5-(Bromomethyl)thiophene-2-carbonitrile is used as a precursor in the production of dyes. Its properties enable the creation of a wide range of colors, making it a valuable asset in the formulation of dyes for various applications, such as textiles, plastics, and printing inks.
Used in Research and Development:
5-(Bromomethyl)thiophene-2-carbonitrile is also utilized in research and development settings, where it serves as a starting material for the exploration of new chemical reactions and the synthesis of novel compounds. Its versatility in chemical reactions makes it an important tool for scientists and researchers in the field of organic chemistry.

Upstream product

• 765-58-2 2-bromo-5-methyl thiophene 
• 72835-25-7 2-cyano-5-methylthiophene 
• 34241-39-9 azobisisobutyronitrile 
• 94-36-0 dibenzoyl peroxide 
• 558-13-4 carbon tetrabromide 
• 172349-09-6 5-(hydroxymethyl)thiophene-2-carbonitrile 
• 554-14-3 2-Methylthiophene 
• 79387-71-6 (5-bromothien-2-yl)methanol 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 

Downstream Products

• 172349-10-9 5-(aminomethyl)thiophene-2-carbonitrile hydrochloride 
• 280781-55-7 N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl[(5-hydroxyamidino-2-thienyl)methyl]amide 

Relevant academic research and scientific papers

Potent and efficacious thienylamidine-incorporated thrombin inhibitors

Novel thrombin inhibitors incorporating thienylamidine at the P1 position were designed and synthesized. These compounds are potent, trypsin- selective and efficacious in the rat model of venous thrombosis. The proposed P1 binding mode in the thrombin active site was confirmed by X-ray crystallographic analysis.

THROMBIN INHIBITORS

The present invention relates to a compound having formula I:and pharmaceutically acceptable salts thereof. The compounds of formula I and pharmaceutical compositions containing them are of the class of thrombin inhibitors which are useful as anticoagulants.

Thrombin inhibitors having a lactam at P3

The present invention provides compounds having a lactam ring at P3 and at P1 have a six-membered heterocyclic ring having two ring nitrogen ring atoms and the remainder of the ring atoms carbon atoms. These compounds have biological activity as active and potent inhibitors of thrombin. Their pharmaceutically acceptable salts, pharmaceutical compositions thereof and methods of using these compounds and pharmaceutical compositions comprising these compounds as therapeutic agents for treatment of disease states in mammals which are characterized by abnormal thrombosis are also described.

Non-covalent inhibitors of urokinase and blood vessel formation

Novel compounds having activity as non-covalent inhibitors of urokinase and having activity in reducing or inhibiting blood vessel formation are provided. These compounds have P1 a group having an amidino or guanidino moiety or derivative thereof. These compounds are useful in vitro for monitoring plasminogen activator levels and in vivo in treatment of conditions which are ameliorated by inhibition of or decreased activity of urokinase and in treating pathologic conditions wherein blood vessel formation is related to a pathologic condition.

Efficacious and orally bioavailable thrombin inhibitors based on a 2,5-thienylamidine at the P1 position: Discovery of N-carboxymethyl-D-diphenylalanyl-L-prolyl[(5-amidino-2- thienyl)methyllamide

Thrombin, a crucial enzyme in the blood coagulation, has been a target for antithrombotic therapy. Orally active thrombin inhibitors would provide effective and safe prophylaxis for venous and arterial thrombosis. We conducted optimization of a highly efficacious benzamidine-based thrombin inhibitor LB30812 (3, Ki = 3 pM) to improve oral bioavailability. Of a variety of arylamidines investigated at the P1 position, 2,5-thienylamidine effectively replaced the benzamidine without compromising the thrombin inhibitory potency and oral absorption. The sulfamide and sulfonamide derivatization at the N-terminal position in general afforded highly potent thrombin inhibitors but with moderate oral absorption, while the well-absorbable N-carbamate derivatives exhibited limited metabolic stability in S9 fractions. The present work culminated in the discovery of the N-carboxymethyl- and 2,5-thienylamidine-containing compound 22 that exhibits the most favorable profiles of anticoagulant and antithrombotic activities as well as oral bioavilability (Ki = 15 pM; F = 43%, 42%, and 15% in rats, dogs, and monkeys, respectively). This compound on a gravimetric basis was shown to be more effective than a low molecular weight heparin, enoxaparin, in the venous thrombosis models of rat and rabbit. Compound 22 (LB30870) was therefore selected for further preclinical and clinical development.

Thrombin inhibitors

The present invention relates to a compound having formula I: and pharmaceutically acceptable salts thereof. The compounds of formula I and pharmaceutical compositions containing them are of the class of thrombin inhibitors which are useful as anticoagula

Non-covalent inhibitors of urokinase and blood vessel formation

Novel compounds having activity as non-covalent inhibitors of urokinase and having activity in reducing or inhibiting blood vessel formation are provided. These compounds have Pi a group having an amidino or guanidino moiety or derivative thereof. These compounds are useful in vitro for monitoring plasminogen activator levels and in vivo in treatment of conditions which are ameliorated by inhibition of or decreased activity of urokinase and in treating pathologic conditions wherein blood vessel formation is related to a pathologic condition.

Noncovalent tripeptidic thrombin inhibitors incorporating amidrazone, amine and amidine functions at P1

A series of noncovalent tripeptidic thrombin inhibitors incorporating amidrazone, amine and amidine functions at P1 was investigated. While the amidrazone and the amine series displayed limited oral absorption, the amidine series demonstrated generally good oral absorption and strong antithrombotic activity; the single-digit picomolar Ki achieved from this series is among the best yet reported. The present work highlights the benzamidine compound 11f (LB30812) that exhibits excellent overall profiles of potency, oral absorption and antithrombotic efficacy.

Novel, potent non-covalent thrombin inhibitors incorporating P3-lactam scaffolds

Evolution of P1-argininal inhibitor prototypes led to a series of non-covalent P3-7-membered lactam inhibitors 1a-w, featuring novel peptidomimetic units that probe each of the S1, S2, and S3 specificity pockets of thrombin. Rigid P1-arginine surrogates possessing a wide range of basicity (calcd pKa's～neutral-14) were surveyed. The design, synthesis, and biological activity of these targets are presented.

ANTITHROMBOTIC AGENTS

This invention relates to thrombin inhibiting compounds having the Formula IX--Y--NH--(CH 2) r--G I where X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.