WO2005065046A3 - An efficient industrial process for 3-hydroxy-3-(3’-sulfamyl-4’-chlorophenyl)phtalimidine - Google Patents

An efficient industrial process for 3-hydroxy-3-(3’-sulfamyl-4’-chlorophenyl)phtalimidine Download PDF

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Publication number
WO2005065046A3
WO2005065046A3 PCT/IN2004/000370 IN2004000370W WO2005065046A3 WO 2005065046 A3 WO2005065046 A3 WO 2005065046A3 IN 2004000370 W IN2004000370 W IN 2004000370W WO 2005065046 A3 WO2005065046 A3 WO 2005065046A3
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WO
WIPO (PCT)
Prior art keywords
formula
phtalimidine
chlorophenyl
sulfamyl
hydroxy
Prior art date
Application number
PCT/IN2004/000370
Other languages
French (fr)
Other versions
WO2005065046A2 (en
Inventor
Ashok Kumar
Dharmendra Singh
Atul Jadhav
Darpan Navinchandra Pandya
Original Assignee
Ipca Lab Ltd
Ashok Kumar
Dharmendra Singh
Atul Jadhav
Darpan Navinchandra Pandya
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
Priority claimed from IN7MU2004 external-priority patent/IN205622B/en
Application filed by Ipca Lab Ltd, Ashok Kumar, Dharmendra Singh, Atul Jadhav, Darpan Navinchandra Pandya filed Critical Ipca Lab Ltd
Publication of WO2005065046A2 publication Critical patent/WO2005065046A2/en
Publication of WO2005065046A3 publication Critical patent/WO2005065046A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide

Abstract

The oximination/cyclization of 2-(4-chlorobenzoyl)benzoic acid with hydroxylamine hydrochloride in presence of molar quantities of inorganic base in water or in alcoholic solvents to form 4-(4’-chlorophenyl)-5,6-bent-oxazine-l-one Formula (8) in high yield and purity; reduction of latter with zinc metal and acetic acid to the corresponding phtalimidine of Formula (9); followed by conversion into 2-(3’-chlorosulphonyl-4’-chlorophenyl)phtalimidine Formula (10) by reaction with chlorosulphonic acid and thionyl chloride in the absence of solvent. Amidation of compound of formula (10) was carried out with ammonia gas/solution in non.-aqueous solvent like ketones and polar aprotic solvents like dimethylformamide, to yield compound of formula (11). Oxidation of Formula (11) with hydrogen peroxide in presence of alkali results in high yield of chlorihalidone.
PCT/IN2004/000370 2004-01-02 2004-11-30 An efficient industrial process for 3-hydroxy-3-(3’-sulfamyl-4’-chlorophenyl)phtalimidine WO2005065046A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN7MU2004 IN205622B (en) 2001-08-13 2004-01-02
IN7/MUM/2004 2004-01-02
IN374/MUM/2004 2004-03-26
IN374MU2004 2004-03-26

Publications (2)

Publication Number Publication Date
WO2005065046A2 WO2005065046A2 (en) 2005-07-21
WO2005065046A3 true WO2005065046A3 (en) 2006-08-17

Family

ID=34751867

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2004/000370 WO2005065046A2 (en) 2004-01-02 2004-11-30 An efficient industrial process for 3-hydroxy-3-(3’-sulfamyl-4’-chlorophenyl)phtalimidine

Country Status (1)

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WO (1) WO2005065046A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018158777A1 (en) 2017-03-01 2018-09-07 Mylan Laboratories Limited Improved process for the preparation of chlorthalidone

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4322356A (en) * 1978-10-10 1982-03-30 The Dow Chemical Co. Method of preparing substituted phthalides
US4331600A (en) * 1980-10-31 1982-05-25 Usv Pharmaceutical Corporation Intermediates for the synthesis of phthalimidines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4322356A (en) * 1978-10-10 1982-03-30 The Dow Chemical Co. Method of preparing substituted phthalides
US4331600A (en) * 1980-10-31 1982-05-25 Usv Pharmaceutical Corporation Intermediates for the synthesis of phthalimidines

Also Published As

Publication number Publication date
WO2005065046A2 (en) 2005-07-21

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