90055-55-3

Basic information

• Product Name: Thieno[3,2-c]pyridine-5(4H)-acetic acid, a-(2-chlorophenyl)-6,7-dihydro-
• CAS NO: 90055-55-3
• Molecular Formula: C15H14ClNO2S
• Molecular Weight: 307.801
• Mol File: 90055-55-3.mol

Chemical Properties

• CAS DataBase Reference: Thieno[3,2-c]pyridine-5(4H)-acetic acid, a-(2-chlorophenyl)-6,7-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: Thieno[3,2-c]pyridine-5(4H)-acetic acid, a-(2-chlorophenyl)-6,7-dihydro-(90055-55-3)
• EPA Substance Registry System: Thieno[3,2-c]pyridine-5(4H)-acetic acid, a-(2-chlorophenyl)-6,7-dihydro-(90055-55-3)

Safety Data

• Hazardous Substances Data: 90055-55-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Thieno[3,2-c]pyridine-5(4H)-acetic acid, a-(2-chlorophenyl)-6,7-dihydrois used as a potential drug candidate for various applications in the pharmaceutical industry. Its unique chemical structure suggests that it may possess biological properties that could be harnessed for the development of new medications. Further research and exploration are required to determine its specific applications and therapeutic potential.

Upstream product

• 444728-11-4 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetonitrile 
• 1130832-62-0 2-(2-chlorophenyl)-N-cyclohex-2-enyl-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetamide 
• 90055-68-8 (+/-)-methyl-(2-chlorophenyl)-(4,5,6,7-4H-thieno[3,2,-c]pyrid-5-yl) acetamide 
• 444891-19-4 2-bromo-2-(2-chlorophenyl)acetonitrile 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 28783-41-7 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride 
• 298-12-4 Glyoxilic acid 
• 324757-50-8 clopidogrel carboxylate 
• 29270-30-2 α-bromo-2-chlorophenyl acetic acid 
• 90055-81-5 ethyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate 
• 90055-48-4 clopidogrel 
• 54903-50-3 4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 50-00-0 formaldehyd 

Downstream Products

• 1015247-88-7 (+/-)-((2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetic acid hydrochloride 
• 1015247-89-8 (+/-)-((2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetic acid acetate 
• 1015247-90-1 (+)-((2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetic acid (1R)-(-)-camphor-10-sulfonate 
• 917613-69-5 (S)-(+)-α-(2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-acetic acid, (1R,2R)-(-)-2-amino-1-phenyl-1,3-propanediol salt 
• 917613-68-4 (S)-(+)-α-(2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-acetic acid, (1R,2R)-(-)-2-amino-1-(4-nitrophenyl)-1,3-propanediol salt 
• 90055-48-4 clopidogrel 
• 113665-84-2 (S)-(+)-clopidogrel 
• 1147350-77-3 cis-5-thiol metabolite 
• 120202-66-6 (S)-(+)-clopidogrel bisulfate 
• 144457-28-3 SR 26334 
• 1007128-30-4 C₁₅H₁₄ClNO₂S*C₁₉H₂₂N₂O 
• 324757-50-8 clopidogrel carboxylate 

Relevant articles and documents

Clopidogre and wherein the intermediate α-bromo-ortho-chlorophenyl acetic acid and α-thiophene substituted ethylamino- method for the preparation of acetic acid hydrochloride (by machine translation)

The invention discloses a preparation method of clopidogrel and intermediates thereof. The preparation method of the clopidogrel and intermediates thereof, provided by the invention, has the characteristics of being simple to operate, mild in reaction condition, little in pollution, low in energy consumption and the like and is suitable for industrial production, a high-purity intermediate can be provided for production of the clopidogrel, and the production cost of the clopidogrel is reduced.

Prodrugs of anti-platelet agents

The invention relates to the compounds of formula I, formula II, formula Ia, formula IIb or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II, formula Ia, formula IIb and methods for treating or preventing atherothrombosis may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment or management of ischemia, stroke, cerebral thrombosis, arterial thrombosis, thrombotic cerebrovascular, cardiovascular diseases and blood clots.

Designing analogs of ticlopidine, a wall teichoic acid inhibitor, to avoid formation of its oxidative metabolites

The thienopyridine antiplatelet agent, ticlopidine and its analog, clopidogrel, have been shown to potentiate the action of β-lactam antibiotics, reversing the methicillin-resistance phenotype of methicillin-resistant Staphylococcus aureus (MRSA), in vitro. Interestingly, these thienopyridines inhibit the action of TarO, the first enzyme in the synthesis of wall teichoic acid, an important cell wall polymer in Gram-positive bacteria. In the human body, both ticlopidine and clopidogrel undergo a rapid P450-dependent oxidation into their respective antiplatelet-active metabolites, resulting in very low plasma concentrations of intact drug. Herein, a series of analogs of ticlopidine and clopidogrel that would avoid oxidative metabolism were designed, prepared and evaluated as inhibitors of TarO. Specifically, we replaced the P450-labile thiophene ring of ticlopidine and clopidogrel to a more stable phenyl group to generate 2-(2-chlorobenzyl)-1,2,3,4-tetrahydro- isoquinoline) (6) and (2-chloro-phenyl)-(3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid methyl ester (22), respectively. The latter molecules displayed inhibitory activity against TarO and formed the basis of a library of analogs. Most synthesized compounds exhibited comparable efficacy to ticlopidine and clopidogrel. So far, it was introduction of a trifluoromethyl group to compound 6, to generate 2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline (13) that exhibited enhanced activity against TarO. Compound 13 represents a novel stable inhibitor of TarO with synergistic impact on β-lactam antibiotics against MRSA and low potential for P-450 metabolism.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF ATHEROTHROMBOSIS

The disclosures herein provide compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These salts may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for peroral administration- transdermal administration, transmucosal, syrups, topical, extended release, sustained release, or injection. Such compositions may foe used to treatment of vascular disorders or conditions such as thrombotic cerebrovascular or cardiovascular disease or its associated complications.

PRODRUGS OF ANTI-PLATELET AGENTS

Disclosed is the compounds of formula (I), formula (II), formula (la), formula (IIb) or its pharmaceutical acceptable salts, polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising and effective amount of formula (I), formula (II), formula (la), formula (lIb) and may be used to treatment or management of ischemia, stroke, cerebral thrombosis, arterial thrombosis, thrombotic cerebrovascular, cardiovasculard diseases and blood colts.

COMPOSITIONS AND METHODS FOR TREATING ATHEROTHROMBOSIS

Provided are compounds of formula (I), pharmaceutical acceptable salts, polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising the compounds may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup or injection, and may be used for the treatment or management of ischemia, cerebral thrombosis, arterial thrombosis, thrombotic cerebrovascular, cardiovascular diseases and blood clots.

PROCESS FOR THE PREPARATION OF CLOPIDOGREL AND SALTS THEREOF

The present invention relates to an improved process for the preparation of Clopidogrel, and pharmaceutical acceptable salts thereof, and in particular to a cost-effective process for large scale production of highly pure Clopidogrel besylate.

Multicomponent reactions as a powerful tool for generic drug synthesis

Multicomponent reactions (MCRs) are not only a powerful tool for drug discovery, they also represent an excellent methodology for synthesis rationalization. Here we wish to illustrate the potential of MCRs in the production of generic drugs by synthesizing, in racemic form, the antiplatelet agent clopidogrel and the nonsteroidal antiandrogen bicalutamide, using Ugi, Petasis and Passerini reactions. Georg Thieme Verlag Stuttgart.

Method of Preparing Clopidogrel and Intermediates Used Therein

Optically pure clopidogrel can be prepared in a high yield by optically resolving a racemic form of the compound of formula (II) using an optically active amine to form the optically active form of the compound of formula (III) or its acid-addition salt; and methylating the compound of formula (III) or its acid-addition salt.

PREPARATION OF CLOPIDOGREL AND ITS ANALOGUES METHYL TETRAHYDROTHIENOPYRIDINE ACETATE COMPOUNDS

The present invention disclosed a preparation method of Clopidogrel (X=2-Cl) and its analogues of methyl tetrahydrothienopyridine acetate (I) by using halogen phenyl acetonitrile (VIII) as starting material and tetrahydrothienopyridine acetonitrile (IV), tetrahydrothienopyridine acetate (V) as key intermediates, and further using kinetic resolution to prepare the optical active Clopidogrel and compounds of methyl tetrahydrothenopridine acetate of formula (XII). The Clopidogrel of present invention is a novel high effective and safety drug for inhibition of platelet aggregation. This invention applied systematic technique of racemization of unwanted optical active enantiomer, recover recycle and reuse of resolution agent etc., with greater economic advantages and suitable for commercial scale industrial production. Wherein: X represents atoms of hydrogen, fluorine, chlorine, bromine or iodine, M represents an alkali metal ion.