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US 9,434,705 B2Granted
L-setastine hydrochloride and preparation method thereof
AssigneeAnhui Qingyun Pharmaceutical & Chemical Co., Ltd.
InventorsQingyun Huang, Qingguo Huang, Meixian Lou
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Abstract
The present invention relates to the field of medicine, and disclosed are an L-setastine hydrochloride and a preparation method therefor. The compound of the present invention has the advantages of stronger histamine Hi receptor antagonism and small side effect; the yield of the preparation method is more than 80%, and the product purity is high. The present invention also provides an application of the compound as an H1 histamine receptor antagonist.
Claims10
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said solvent is toluene solution.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said solvent is acetonitrile.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said solvent is tetrahydrofuran.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said solvent is dichloromethaneane.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said alkali-based compound is sodium tert-butoxide.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said alkali-based compound is sodium hydride.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said alkali-based compound is 1, 8-Diazabicyclo[5.4.0]undec-7-ene (DBU).
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein a catalyst is provided to support the reaction between said formula II and formula III, wherein said catalyst is polyethylene glycol.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein a catalyst is provided to support the reaction between said formula II and formula III, wherein said catalyst is crown ether.
3 more elements
A method for preparing a compound of L-setastine hydrochloride, comprising the steps of,
- (a) providing a compound of formula II having a formula of:
- wherein the X is selected from a group consisting of Chlorine (Cl), Bromine (Br), Iodium (I), acyloxy, and sulfonyloxy;
- (b) providing a compound of formula III having a formula of:
- and
- (c) reacting said compound of formula II with said compound of formula III in absence of air or in presence of air and an environment of alkali-based compound, and in a solvent under a solvent reflux temperature for 4 to 6 hours to obtain said compound of L-setastine hydrochloride;
- wherein said L-setastine hydrochloride is analyzed by a NMR instrument.
3 more elements
Dependencies are inferred from the claim text.