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WO2008056378A3 - Novel process for the preparation of naratriptan hydrochloride - Google Patents

Novel process for the preparation of naratriptan hydrochloride Download PDF

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Publication number
WO2008056378A3
WO2008056378A3 PCT/IN2007/000534 IN2007000534W WO2008056378A3 WO 2008056378 A3 WO2008056378 A3 WO 2008056378A3 IN 2007000534 W IN2007000534 W IN 2007000534W WO 2008056378 A3 WO2008056378 A3 WO 2008056378A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
preparation
naratriptan hydrochloride
novel process
indole
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IN2007/000534
Other languages
French (fr)
Other versions
WO2008056378A2 (en
Inventor
Reddy Muddasani Pulla
Reddy Peddi Rajasekhara
Chowdary Nannapaneni Venkaiah
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Natco Pharma Ltd
Original Assignee
Natco Pharma Ltd
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 Natco Pharma Ltd filed Critical Natco Pharma Ltd
Publication of WO2008056378A2 publication Critical patent/WO2008056378A2/en
Publication of WO2008056378A3 publication Critical patent/WO2008056378A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Present invention provides a novel and improved process for the preparation of N- methyl-1H-indole-5-ethanesulfonamide of formula (I). Compound of formula (I) is a key intermediate used in the synthesis of naratriptan hydrochloride of formula (II). Hydrazone derivative of formula (XL) derived from the corresponding hydrazine and pyruvate ester is reacted with an acid catalyst to get the indole-2-carboxylate derivative of formula (XLI). Hydrolysis of this ester and decarboxylation gave the compound of formula (I). Naratriptan hydrochloride (Amerge) is widely used as anti-migraine drug in the market.
PCT/IN2007/000534 2006-11-09 2007-11-09 Novel process for the preparation of naratriptan hydrochloride Ceased WO2008056378A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2066CH2006 2006-11-09
IN2066/CHE/2006 2006-11-09

Publications (2)

Publication Number Publication Date
WO2008056378A2 WO2008056378A2 (en) 2008-05-15
WO2008056378A3 true WO2008056378A3 (en) 2008-09-25

Family

ID=39323819

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000534 Ceased WO2008056378A2 (en) 2006-11-09 2007-11-09 Novel process for the preparation of naratriptan hydrochloride

Country Status (1)

Country Link
WO (1) WO2008056378A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009118753A2 (en) * 2008-03-07 2009-10-01 Usv Limited Process for preparation of naratriptan hydrochloride
WO2010004580A2 (en) * 2008-07-11 2010-01-14 Ind-Swift Laboratories Limited Process for preparing indole derivatives
CN115611854B (en) * 2021-07-15 2024-03-26 天津师范大学 A new method for preparing naratriptan and its derivatives

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0303507A2 (en) * 1987-08-13 1989-02-15 Glaxo Group Limited Indole derivatives
US4994483A (en) * 1983-12-06 1991-02-19 Glaxo Group Limited 5-substituted-3-aminoalkyl indole derivatives for migraine
CN1789262A (en) * 2004-12-16 2006-06-21 上海美通生物科技有限公司 Improved method for preparing Naratriptan

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4994483A (en) * 1983-12-06 1991-02-19 Glaxo Group Limited 5-substituted-3-aminoalkyl indole derivatives for migraine
EP0303507A2 (en) * 1987-08-13 1989-02-15 Glaxo Group Limited Indole derivatives
CN1789262A (en) * 2004-12-16 2006-06-21 上海美通生物科技有限公司 Improved method for preparing Naratriptan

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
AKHVLEDIANI R N ET AL: "Synthesis of 5-(2-Pyridyl) Indole", CHEM. HETEROCYCL. COMPD, vol. 24, no. 11, 1988, pages 1221 - 1225, XP002479088 *
MIRZIASHVILI N T ET AL: "Synthesis of 5-(p-Chlorophenylsulfonyl)indole and some of its Derivatives", CHEM. HETEROCYCL. COMPD, vol. 27, no. 1, 1991, pages 45 - 47, XP002479087 *

Also Published As

Publication number Publication date
WO2008056378A2 (en) 2008-05-15

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