# US 8,772,489 B2 · Optically active 2-hydroxy tetrahydrothienopyridine derivatives, preparation method and use in manufacture of medicament thereof

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- Number: US 8,772,489 B2
- Document ID: US8772489B2
- Status: Granted
- Kind: B2
- Application number: 13/576,534
- Filed: 2011-01-28
- Published: 2013-06-27
- Granted: 2014-07-08
- Earliest claimed: 2010-02-02
- Assignees: Jiangsu Vcare PharmaTech Co., Ltd.
- Applicants: Hongbin Sun; Jiaqi Shan; Boyu Zhang; Fang Yuan
- Inventors: Hongbin Sun; Jiaqi Shan; Boyu Zhang; Fang Yuan
- Web page: https://patentgrep.com/patent/US8772489B2

## CPC

- C07D 495/04: Ortho-condensed systems
- A61K 31/4365: the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C07B 2200/07: Optical isomers
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Optically active 2-hydroxytetrahydrothienopyridine derivatives represented by Formula I and pharmaceutically acceptable salts, preparation method and use in the manufacture of a medicament thereof are disclosed. The pharmacodynamic experiment results show that the present compounds of Formula I are useful for inhibiting platelet aggregation. The pharmacokinetic experiment results show that the present compound of Formula I can be converted in vivo into pharmacologically active metabolites and are therefore useful for inhibiting platelet aggregation. Therefore, the present compounds are useful for the manufacture of a medicament for preventing or treating thrombosis and embolism related diseases.

## Claims

### Claim 1

An optically active 2-hydroxytetrahydrothienopyridine derivative, wherein said derivative is (S)-methyl 2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)-acetate or a pharmaceutically acceptable salt thereof.

### Claim 2

A pharmaceutical composition comprising (S)-methyl 2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)-acetate or a pharmaceutically acceptable salt thereof as an active ingredient, and a pharmaceutically acceptable carrier.

### Claim 3 (depends on 2)

The pharmaceutical composition according to claim 2, wherein for an adult, the pharmaceutical composition contains (S)-methyl 2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)-acetate or a pharmaceutically acceptable salt thereof 0.1 mg-1000 mg for oral administration, or 0.01 mg-500 mg for intravenous administration.

### Claim 4 (depends on 2)

The pharmaceutical composition according to claim 2, wherein for an adult, the pharmaceutical composition contains (S)-methyl 2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)-acetate or a pharmaceutically acceptable salt thereof 1 mg-500 mg for oral administration, or 0.1 mg-250 mg for intravenous administration.

### Claim 5 (depends on 2)

The pharmaceutical composition according to claim 2, wherein said pharmaceutical composition is in the form of a tablet, capsule, sustained release tablet, granule, powder, syrup, oral solution, or injection.

### Claim 6

An optically active 2-hydroxytetrahydrothienopyridine derivative or a pharmaceutically acceptable salt thereof, wherein said derivative is (S)-methyl 2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)-acetate, wherein said pharmaceutically acceptable salt is a hydrochloric acid salt, a hydrobromic acid salt, a sulfuric acid salt, a citric acid salt, a tartaric acid salt, a phosphoric acid salt, a lactic acid salt, an acetic acid salt, a maleic acid salt, a fumaric acid salt, a malic acid salt, a mandelic acid salt, a methanesulfonic acid salt, a benzenesulfonic acid salt, a p-toluenesulfonic acid salt, a pamoic acid salt, an oxalic acid salt, or a succinic acid salt.