IP Library › Granted Patent US 10,160,758
Granted Patent B2
US 10,160,758 · App. 15/528,282 · Granted Dec 25, 2018

Method for the production of praziquantel

Inventors: Andreas Waechtler (Darmstadt, DE); Hadia Saleh-Kassim (Forbach, FR); Christian Jasper (Seligenstadt, DE); Joern Kolb (Arheiligen, DE); David Maillard (Darmstadt, DE)
Assignee: MERCK PATENT GMBH
C07D471/04C07B55/00C07B57/00C07C31/30C07B2200/07
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Quick Facts
Patent No.
US 10,160,758
App. No.
15/528,282
Granted
Dec 25, 2018
Kind
B2
Abstract

The present invention relates to a method for the racemization of enantiomerically pure or enantiomerically enriched Praziquantel under basic conditions and a method for the production of (R)-Praziquantel in enantiopure or enantiomerically enriched form, which comprises the racemization method.

Claims (15)

1. A method which comprises racemization of enantiomerically pure or enantiomerically enriched Praziquantel:

wherein a base is used and the base is a tertiary alkyl alkoxide.

2. A method according to claim 1 , wherein the tertiary alkali alkoxide used for the racemization is potassium tert.-butoxide.

3. A method according to claim 1 , wherein the racemization is a performed in a dipolar aprotic reaction medium.

4. A method according to claim 3 , wherein the dipolar aprotic reaction medium is selected from the group consisting of N-Methyl-2-pyrrolidone, dimethylformamide, dimethylsulfoxide, tetrahydrofuran, methyltetrahydrofuran, dioxane and mixtures thereof in all ratios.

5. A method according to claim 1 , wherein the racemization is performed at a temperature in a range between −50° C. and +40° C.

6. A method according claim 1 , wherein the amount of base used for the racemization is in the range of 0.05 eq to 1.5 eq.

7. A method according to claim 1 , wherein:

the racemization is performed in a dipolar aprotic reaction medium selected from a group consisting of N-Methyl-2-pyrrolidone, dimethylformamide, dimethylsulfoxide, tetrahydrofuran, methyltetrahydrofuran, dioxane and mixtures thereof in all ratios;

the amount of base used for the racemization is in the range between 0.05 eq to 1.5 eq;

the racemization is performed at a temperature in the range between −50° C. and +40° C.

8. A method for the production of (R)-Praziquantel in enantiopure or enantiomerically enriched form, comprising following steps:

a. Racemization of enantiomerically pure or enantiomerically enriched (S)-Praziquantel according to claim 1 ; and

b. Chiral resolution of the mixture of the enantiomers (S)-(I) and (R)-Praziquantel obtained in a).

9. A method according to claim 8 , wherein the chiral resolution according to step b) is performed using chromatography.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2017
From: WAECHTLER, ANDREAS; SELEH-KASSIM, HADIA; JASPER, CHRISTIAN; KOLB, JOERN; MAILLARD, DAVID
To: MERCK PATENT GMBH
Reel/Frame 042634/0322 →
Priority Claims (1)
EP 14003934 · Nov 21, 2014 · regional
Continuity (1)
Related Publication 20180155339A1 · Jun 7, 2018
Cited By (1)
US 12,544,336