22353-82-8

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-THIOPHENECARBOXAMIDE is used as an intermediate compound for the development of antithrombotic drugs, specifically for the synthesis of Rivaroxaban. Its role in the drug's mechanism of action is crucial, as it contributes to the highly potent and selective inhibition of Factor Xa, which is essential for the prevention and treatment of various thrombotic disorders.
Used in Cardiovascular Applications:
5-CHLORO-2-THIOPHENECARBOXAMIDE is used as a therapeutic agent for the prevention and treatment of thrombotic events, such as deep vein thrombosis, pulmonary embolism, and stroke. Its ability to selectively inhibit Factor Xa makes it a valuable tool in managing these conditions, as it helps to reduce the risk of clot formation without significantly increasing the risk of bleeding.
Used in Research and Development:
5-CHLORO-2-THIOPHENECARBOXAMIDE is used as a research compound for studying the pharmacological properties and mechanisms of action of Rivaroxaban and other direct Factor Xa inhibitors. This knowledge can be applied to the development of new antithrombotic agents with improved efficacy, safety, and selectivity.
Used in Drug Delivery Systems:
5-CHLORO-2-THIOPHENECARBOXAMIDE can be used in the development of novel drug delivery systems to improve the bioavailability, stability, and targeted delivery of Rivaroxaban and other antithrombotic agents. These systems may include nanoparticles, liposomes, or other advanced drug carriers designed to enhance the therapeutic potential of these compounds while minimizing potential side effects.

InChI:InChI=1/C5H4ClNOS/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H2,7,8)

Upstream product

• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 35475-03-7 methyl 5-chloro-2-thiophenecarboxylate 
• 6310-09-4 2-acetyl-5-chlorothiophene 
• 125712-84-7 1-(5-chloro-thiophen-2-yl)-ethanol 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 14345-95-0 (E)-N-[(5-chlorothiophen-2-yl)methylidene]hydroxylamine 
• 96-43-5 2-thienyl chloride 
• 463-72-9 carbamic chloride 

Downstream Products

• 366789-02-8 Rivaroxaban 
• 1313610-85-3 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-hydroxy-2-naphthoate 
• 1313610-84-2 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide phosphate 
• 1313610-83-1 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide thiocyanate 
• 1312422-72-2 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide methanesulfonate 
• 58884-89-2 5-(5-chloro-2-thienyl)-1H-tetrazole 
• 214759-22-5 C-(5-Chloro-thiophen-2-yl)-methylamine 

Relevant academic research and scientific papers

Heterocyclic compound and application thereof

The present disclosure relates to a heterocyclic compound represented by general formula I, a pharmaceutically acceptable salt, a stereoisomer, an enantiomer, a diastereoisomer, an atropisomer, an optical isomer, a raceme, a polymorphic substance, a solvate or an isotope labeled compound thereof, a pharmaceutical composition containing the heterocyclic compound, and a pharmaceutical use thereof. The heterocyclic compound disclosed by the invention is an immunomodulator, and particularly relates to an immunomodulator of a compound for activating STING.

Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus

Influenza A virus is an enveloped negative single-stranded RNA virus that causes febrile respiratory infection and represents a clinically challenging threat to human health and even lives worldwide. Even more alarming is the emergence of highly pathogenic avian influenza (HPAI) strains such as H5N1, which possess much higher mortality rate (60%) than seasonal influenza strains in human infection. In this study, a novel series of heteroaromatic-based benzenesulfonamide derivatives were identified as M2 proton channel inhibitors. A systematic investigation of the structure-activity relationships and a molecular docking study demonstrated that the sulfonamide moiety and 2,5-dimethyl-substituted thiophene as the core structure played significant roles in the anti-influenza activity. Among the derivatives, compound 11k exhibited excellent antiviral activity against H5N1 virus with an EC50 value of 0.47 μM and selectivity index of 119.9, which are comparable to those of the reference drug amantadine.

A [...] intermediate 5 - chloro - N - (2 - oxirane ylmethyl) -2 - thiophene carboxamide preparation method

The invention provides a preparation method for a Rivaroxaban intermediate 5-chloro-N-(2-oxiranylmethyl)-2-thiophene methanamide. First, 5-chlorothiophene-2-formic acid and toluene are added into a reaction container, the temperature is risen to 80-85 DEG C slowly, then thionyl chloride is dripped slowly, and the temperature is risen to 95-105 DEG C; the reaction solution is cooled to 50-60 DEG C, equal-temperature reduced pressure distillation is carried out, the solvent is evaporated, and after toluene is added, a toluene solution of 5-chlorothiophene-2-formyl chloride is obtained; then propane is added in the toluene solution of 5-chlorothiophene-2- formyl chloride, then ammonia water is dripped under an ice-bath condition, and 5-chlorothiophene-2-methanamide is obtained; then 5-chlorothiophene-2-methanamide and potassium carbonate are added in a reaction container, then epoxy chloropropane is added, and after heating and stirring, 5-chloro-N-(2-oxiranylmethyl)-2-thiophene methanamide is obtained. In the technology route, reaction conditions are optimized, the reaction is mild, operation is simple, and the yield is high.

The preparation method of the [...] (by machine translation)

The invention provides a method for preparing [...], using 4 - (4 - aminophenyl) - 3 - morpholone and 5 - chloro - N - (2 - ethylene oxide-based methyl) - 2 - thiophene carboxamide reaction to obtain 5 - [...] - 2 - {(R)- 2 - hydroxy - 3 - [4 - (3 - oxo - 4 - morpholinyl) phenyl amino] - propyl} amide, then adding N, N' - carbonyl di-imidazole, 4 - dimethylamino pyridine, begins to stir, heating reaction to obtain the - 5 - chloro - N - (( (5 S) - 2 - oxo - 3 - (4 - (3 - oxo-morpholine - 4 - yl) phenyl) - 1, 3 - Oxacillin - 5 - yl) methyl) thiophene - 2 - carboxamide. The technique of the invention route after the condition is optimized, mild reaction, high yield. (by machine translation)

Rivaroxaban preparation method

The invention discloses a rivaroxaban preparation method and belongs to the field of medical chemistry. The method comprises the steps: firstly reacting N-(4-aminophenyl)-3-morpholinone with Boc anhydride or benzylcarbonyl chloride or other ester to generate N-(4-alkoxycarbonyl aminophenyl)-3-morpholinone intermediate I; reacting 5-chlorothiophene-2-methanamide with epoxy chloropropane to generate N-(1,2-glycidyl)-5-chlorothiophene-2-methanamide intermediate II. The intermediate I and the intermediate II are open loop-cyclization condensed under alkali condition to be directly prepared into rivaroxaban. The method has short synthesizing path, moderate condition, convenience to operate, high yield, stable product quality and easiness in achieving industrial production. The structural formula is shown in the specification.

Molecular recognition at the active site of factor Xa: Cation-π Interactions, stacking on planar peptide surfaces, and replacement of structural water

Factor Xa, a serine protease from the blood coagulation cascade, is an ideal enzyme for molecular recognition studies, as its active site is highly shape-persistent and features distinct, concave sub-pockets. We developed a family of non-peptidic, small-molecule inhibitors with a central tricyclic core orienting a neutral heterocyclic substituent into the S1 pocket and a quaternary ammonium ion into the aromatic box in the S4 pocket. The substituents were systematically varied to investigate cation-π interactions in the S4 pocket, optimal heterocyclic stacking on the flat peptide walls lining the S1 pocket, and potential water replacements in both the S1 and the S4 pockets. Structure-activity relationships were established to reveal and quantify contributions to the binding free enthalpy, resulting from single-atom replacements or positional changes in the ligands. A series of high-affinity ligands with inhibitory constants down to Ki=2nM were obtained and their proposed binding geometries confirmed by X-ray co-crystal structures of protein-ligand complexes. Factor Xa is an ideal enzyme to undertake molecular recognition studies at atomic level resolution as its active site is completely conserved in complexes with designed ligands. Cation-π interactions, water replacements, and stacking interactions with flat peptide fragments were investigated, revealing large changes in binding affinity resulting from single-atom mutations or positional shifts of heteroatoms in the ligands. Copyright

CRYSTALLINE FORMS OF A FACTOR XA INHIBITOR

The present invention provides crystalline forms of a mesylate salt of the compound 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide and pharmaceutical compositions and methods thereof.

METHODS OF PREPARING FACTOR XA INHIBITORS AND SALTS THEREOF

The present invention provides for methods of preparing compounds of Formula I or a salt of the compound or a hydrate of the compound or salt thereof that are factor Xa inhibitors. Specifically the present invention provides a method of preparing the comp

SALTS AND CRYSTALLINE FORMS OF A FACTOR XA INHIBITOR

The present invention provides salts and crystalline forms of the compound 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide, and pharmaceutical compositions and method of use thereof.

Novel and direct transformation of methyl ketones or carbinols to primary amides by employing aqueous ammonia

Figur Presented A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to corresponding primary amides has been developed. An iodine-NH3·H2O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben-Haller-Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time.