172349-10-9

Basic information

• Product Name: 5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE
• Synonyms: 5-AMINOMETHYL-THIOPHENE-2-CARBONITRILE;5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE;5-(Aminomethyl)-2-thiophenecarbonitrile hydrochloride;2-Thiophenecarbonitrile, 5-(aminomethyl)-, hydrochloride (1:1);2-Thiophenecarbonitrile, 5-(aMinoMethyl)-, Monohydrochloride
• CAS NO: 172349-10-9
• Molecular Formula: C6H7ClN2S
• Molecular Weight: 174.65
• Mol File: 172349-10-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 301 °C at 760 mmHg
• Flash Point: 135.8 °C
• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE(172349-10-9)
• EPA Substance Registry System: 5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE(172349-10-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 172349-10-9(Hazardous Substances Data)

Usage

Description

5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE is an organic compound that serves as a crucial intermediate in the development of pharmaceuticals, particularly in the synthesis of oral thrombin inhibitors. It is characterized by its unique chemical structure, which includes a thiophene ring with an aminomethyl group and a carbonitrile functional group, along with a hydrochloride counterion.

Uses

Used in Pharmaceutical Industry:
5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE is used as a key intermediate in the synthesis of oral thrombin inhibitors for the treatment of various medical conditions. Its application is primarily due to its ability to contribute to the development of effective and safe antithrombotic drugs that can help prevent blood clot formation and related complications.
As an intermediate in the synthesis of oral thrombin inhibitors, 5-(AMINOMETHYL)THIOPHENE-2-CARBONITRILE HYDROCHLORIDE plays a vital role in the pharmaceutical industry. Thrombin inhibitors are essential for managing conditions such as deep vein thrombosis, pulmonary embolism, and acute coronary syndrome. The compound's unique structure allows for the development of potent and selective thrombin inhibitors, which can be used to treat these conditions more effectively and with fewer side effects compared to existing treatments.

InChI:InChI=1S/C6H6N2S.ClH/c7-3-5-1-2-6(4-8)9-5;/h1-2H,3,7H2;1H

Upstream product

• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 134135-41-4 5-(bromomethyl)thiophene-2-carbonitrile 
• 201799-21-5 5-(N,N-Boc₂-aminomethyl)thiophene-2-carbonitrile 
• 72835-25-7 2-cyano-5-methylthiophene 
• 765-58-2 2-bromo-5-methyl thiophene 

Downstream Products

• 1374963-14-0 N-benzylsulfonyl-D-leucyl-L-proline-[(5-cyano-2-thienyl)methyl]amide 

Relevant articles and documents

PEPTIDIC THROMBIN INHIBITOR COMPOUND

The present invention relates to a novel thrombin inhibitor compound which has a good inhibitory effect against thrombosis and can be orally administered, a process for preparing the same, and to a composition for the therapeutic and/or prophylactic treatment of various diseases associated with thrombin inhibition mechanism, which comprises the same as an active ingredient.

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.

ANTITHROMBOTIC AGENTS

This invention relates to thrombin inhibiting compounds having the FormulaIX--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.