IP Library Granted Patent US 7,652,154
Granted Patent B2
US 7,652,154 · App. 12/194,644 · Granted Jan 26, 2010

Method and intermediates for the preparation of derivatives of N (1-benzhydrylazetidin-3-yl)-N-phenylmethylsulfonamide

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Quick Facts
Patent No.
US 7,652,154
App. No.
12/194,644
Granted
Jan 26, 2010
Kind
B2
Abstract

The invention relates to a novel method for the synthesis of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5-difluorophenyl)methylsulfonamide.

Claims (10)

1. A process for the preparation of a compound of formula (IV):

wherein

R and R′ represent, independently of each other, one or more hydrogen, halogen (Cl, F, Br or I), cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms, linear or branched alkoxy of 1 to 6 carbon atoms, linear or branched alkyl carboxylate of 1 to 6 carbon atoms, trifluoromethyl or trifluoromethoxy;

comprising

reacting a compound of formula (V) or an acid salt thereof:

wherein R and R′ are as defined above;

with epibromohydrin or epichlorohydrin at a temperature in the range of from about 20° C. to about 150° C. in an organic solvent in the presence of a suitable base selected from the group consisting of lithium hydrogen carbonate, lithium carbonate, lithium phosphate, lithium hydroxide, sodium carbonate, sodium phosphate, sodium hydroxide, potassium hydrogen carbonate, potassium carbonate, tripotassium phosphate, potassium hydroxide, cesium hydrogen carbonate, cesium carbonate, cesium phosphate, cesium hydroxide, sodium methoxide, sodium ethoxide, sodium t-amyloxide, sodium t-butoxide, potassium methoxide, potassium ethoxide, potassium t-amyloxide, potassium t-butoxide, diisopropylamine, 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo [4.3.0]non-5-ene (DBN) and tetramethylguanidine, and in the presence of an additive, optionally in an aqueous phase.

2. The process according to claim 1 , wherein the base is a combination of sodium hydrogen carbonate and anhydrous tripotassium phosphate.

3. The process according to claim 1 , wherein said additive is sodium iodide.

4. The process according to claim 1 , wherein the solvent is n-butanol.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 14, 2023
From: OPIANT PHARMACEUTICALS, INC.
To: INDIVIOR UK LIMITED
Reel/Frame 063944/0323 →
RELEASE OF SECURITY INTEREST Recorded Mar 9, 2023
From: PONTIFAX MEDISON FINANCE GP, L.P.
To: OPIANT PHARMACEUTICALS, INC.
Reel/Frame 062937/0311 →
SECURITY INTEREST Recorded Dec 10, 2020
From: OPIANT PHARMACEUTICALS, INC.
To: PONTIFAX MEDISON FINANCE GP, L.P.
Reel/Frame 054602/0192 →
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2008
From: BOFFELLI, PHILIPPE; DELTHIL, MICHEL; GRONDARD, LUC; LAMPILAS, MAXIME; MALPART, JOEL; MUTTI, STEPHANE; NAIT-BOUDA, LAHLOU; RIEKE-ZAPP, JOERG
To: SANOFI-AVENTIS
Reel/Frame 021475/0367 →