WO2006062406A3 - Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of q quaternary ammonium salt - Google Patents

Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of q quaternary ammonium salt Download PDF

Info

Publication number
WO2006062406A3
WO2006062406A3 PCT/NL2005/050055 NL2005050055W WO2006062406A3 WO 2006062406 A3 WO2006062406 A3 WO 2006062406A3 NL 2005050055 W NL2005050055 W NL 2005050055W WO 2006062406 A3 WO2006062406 A3 WO 2006062406A3
Authority
WO
WIPO (PCT)
Prior art keywords
quaternary ammonium
preparation
salt
hydroxide
denatonium
Prior art date
Application number
PCT/NL2005/050055
Other languages
French (fr)
Other versions
WO2006062406A2 (en
Inventor
Rajnikant Vyas Janmejay
Jayshree H Shah
Ravindra Niranjanbhai Raval
Original Assignee
Dishman Pharmaceuticals And Ch
Pluim Henk
Rajnikant Vyas Janmejay
Jayshree H Shah
Ravindra Niranjanbhai Raval
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dishman Pharmaceuticals And Ch, Pluim Henk, Rajnikant Vyas Janmejay, Jayshree H Shah, Ravindra Niranjanbhai Raval filed Critical Dishman Pharmaceuticals And Ch
Priority to US11/720,931 priority Critical patent/US20090306429A1/en
Priority to BRPI0518466-5A priority patent/BRPI0518466A2/en
Priority to CA002591272A priority patent/CA2591272A1/en
Priority to EP05809075A priority patent/EP1824814A2/en
Publication of WO2006062406A2 publication Critical patent/WO2006062406A2/en
Publication of WO2006062406A3 publication Critical patent/WO2006062406A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a process for the preparation of a quaternary ammonium hydroxide, in particular denatonium hydroxide, and the use thereof for the preparation of a quaternary ammo nium salt, in particular of denatonium benzoate or a denatonium fatty acid derivative. Due to its extremely bitter taste, this latter compound is applied in the art as an aversive agent, biocide, antifoulant and flavorant. It is usually prepared from a quaternary ammonium halide in an organic environment, which after isolation and purification is converted to a hygroscopic and unstable hydroxide intermediate, which in turn is immediately converted to the salt of interest in the solvent in which it is prepared. It is now found that these isolation steps can be avoided by performing the reaction at aqueous conditions. This is more straightforwardly and does not require costly precaut ions to avoid contact while handling. Moreover, the process of the invention allows to produce the quaternary ammonium salt from a lignocaine compound in a one-pot synthesis involving mostly water.
PCT/NL2005/050055 2004-12-06 2005-11-30 Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of q quaternary ammonium salt WO2006062406A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US11/720,931 US20090306429A1 (en) 2004-12-06 2005-11-30 Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of a quaternary ammonium salt
BRPI0518466-5A BRPI0518466A2 (en) 2004-12-06 2005-11-30 processes for the preparation of a hydroxide and a quaternary ammonium salt and,
CA002591272A CA2591272A1 (en) 2004-12-06 2005-11-30 Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of a quaternary ammonium salt
EP05809075A EP1824814A2 (en) 2004-12-06 2005-11-30 Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of q quaternary ammonium salt

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US63297604P 2004-12-06 2004-12-06
EP04078299 2004-12-06
EP04078299.7 2004-12-06
US60/632,976 2004-12-06

Publications (2)

Publication Number Publication Date
WO2006062406A2 WO2006062406A2 (en) 2006-06-15
WO2006062406A3 true WO2006062406A3 (en) 2006-09-28

Family

ID=34928707

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2005/050055 WO2006062406A2 (en) 2004-12-06 2005-11-30 Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of q quaternary ammonium salt

Country Status (5)

Country Link
EP (1) EP1824814A2 (en)
CN (1) CN101111473A (en)
BR (1) BRPI0518466A2 (en)
CA (1) CA2591272A1 (en)
WO (1) WO2006062406A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102016009766A1 (en) 2016-08-11 2018-02-15 Julius-Maximilians-Universität Würzburg Production of bitter substance derivatives
CN110354754A (en) * 2019-07-10 2019-10-22 齐齐哈尔大学 Amide bond quaternary cationics with different the morphology of the aggregate
CN112593078B (en) * 2020-12-03 2022-08-05 江西理工大学 Synthetic method of organic quaternary ammonium salt

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB955309A (en) * 1959-11-20 1964-04-15 Edinburgh Pharmaceutical Ind L New quaternary salts and compositions containing them
EP0318262A1 (en) * 1987-11-24 1989-05-31 Glaxo Group Limited Compositions
WO1999015495A1 (en) * 1997-09-19 1999-04-01 Burlington Bio-Medical & Scientific Corp. Denatonium capsaicinate and methods of producing the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB955309A (en) * 1959-11-20 1964-04-15 Edinburgh Pharmaceutical Ind L New quaternary salts and compositions containing them
EP0318262A1 (en) * 1987-11-24 1989-05-31 Glaxo Group Limited Compositions
WO1999015495A1 (en) * 1997-09-19 1999-04-01 Burlington Bio-Medical & Scientific Corp. Denatonium capsaicinate and methods of producing the same

Also Published As

Publication number Publication date
CN101111473A (en) 2008-01-23
WO2006062406A2 (en) 2006-06-15
EP1824814A2 (en) 2007-08-29
CA2591272A1 (en) 2006-06-15
BRPI0518466A2 (en) 2008-11-18

Similar Documents

Publication Publication Date Title
EP1712549A4 (en) Optically active quaternary ammonium salt having axial asymmetry and process for producing alpha-amino acid and derivative thereof with the same
WO2006108792A8 (en) New heterocyclylethylbenzamide derivatives
WO2008114506A1 (en) Method for producing 4-aminomethylbenzoic acid
ATE441627T1 (en) METHOD FOR PRODUCING VALSARTAN
EP1870403A8 (en) Optically active quaternary ammonium salt having axial asymmetry and process for producing alpha-amino acid and derivative thereof with the same
WO2006062406A3 (en) Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of q quaternary ammonium salt
RU2009111276A (en) METHOD FOR PRODUCING 1- (3, 4-Dichlorobenzyl) -5-octylbiguanide or its salt
WO2007038277A3 (en) Resolution of alpha-(phenoxy) phenylacetic acid derivatives with naphthyl-alkylamines
RU2372340C2 (en) Method of producing thiazole through aminomethylation
WO2010008729A3 (en) Process for making substituted 2-amino-thiazolones
IL272559B2 (en) Method for the preparation of 4-(heptafluoro-2-propyl) anilines
JP6462703B2 (en) Process for preparing 1-alkyl-3-difluoromethyl-5-fluoro-1H-pyrazole-4-carbaldehydes and 1-alkyl-3-difluoromethyl-5-fluoro-1H-pyrazole-4-carboxylates
RS20060225A (en) Process for the preparation of n-amino substituted heterocyclic compounds
WO2006069113A3 (en) Method to produce a carboxylic acid ester from a carboxylic acid ammonium salt by alcoholysis
EP1824823A4 (en) Process for the manufacture of 3-hydroxy-n-alkyl-1-cycloalkyl-6-alkyl-4-oxo-1,4-dihydropyridine-2-carboxamide and its related analogues
JP5816268B2 (en) Process for the preparation of dithiine-tetracarboxy-diimide
WO2009017241A3 (en) Process for producing toluidine compound
WO2004085391B1 (en) Process for the synthesis of amorphous atorvastatin calcium
AU2007213270A1 (en) Improved process for producing nitroisourea derivatives
WO2007017244A3 (en) A PROCESS FOR THE PURIFICATION OF SUBSTITUTED 2-(2-PYRIDYLMETHYL)SULFINYL-lH-BENZIMIDAZOLE COMPOUNDS BY PRECIPITATION IN THE PRESENCE OF A QUATERNARY AMMONIUM SALT
WO2009039241A3 (en) Improved process for preparing cinacalcet hydrochloride
RU2005141200A (en) WATER-SOLUBLE AMINOFULERENES AND METHODS FOR PRODUCING THEM
WO2008003744A3 (en) N-methyl benzamide derivatives useful as fungicides
WO2007095980A8 (en) Modified amino acids
DE602006005488D1 (en) PROCESS FOR THE PREPARATION OF LOSARY ALTERNATIVES BY CHLORING AND REDUCING THE CORRESPONDING 1H-IMIDAZOLE-5-CARBALDEHYDE

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KN KP KR KZ LC LK LR LS LT LU LV LY MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2591272

Country of ref document: CA

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2005809075

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 4561/DELNP/2007

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 200580047541.9

Country of ref document: CN

WWP Wipo information: published in national office

Ref document number: 2005809075

Country of ref document: EP

ENP Entry into the national phase

Ref document number: PI0518466

Country of ref document: BR

WWE Wipo information: entry into national phase

Ref document number: 11720931

Country of ref document: US