WO2005062723A3 - An improved process for the preparation of 7-chloro-4-(5-n-ehtyl-n-2-hydroxyethylamine)-2-pentyl] aminoquinoline and its intermediates - Google Patents

An improved process for the preparation of 7-chloro-4-(5-n-ehtyl-n-2-hydroxyethylamine)-2-pentyl] aminoquinoline and its intermediates Download PDF

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Publication number
WO2005062723A3
WO2005062723A3 PCT/IN2004/000364 IN2004000364W WO2005062723A3 WO 2005062723 A3 WO2005062723 A3 WO 2005062723A3 IN 2004000364 W IN2004000364 W IN 2004000364W WO 2005062723 A3 WO2005062723 A3 WO 2005062723A3
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WO
WIPO (PCT)
Prior art keywords
chloro
aminoquinoline
intermediates
pentyl
preparation
Prior art date
Application number
PCT/IN2004/000364
Other languages
French (fr)
Other versions
WO2005062723A2 (en
Inventor
Ashok Kumar
Ketan Dhansukhlal Vyas
Dharmendra Singh
Sanjay Nandavadekar
Sanjay Bhise
Atul Jadhav
Original Assignee
Ipca Lab Ltd
Ashok Kumar
Ketan Dhansukhlal Vyas
Dharmendra Singh
Sanjay Nandavadekar
Sanjay Bhise
Atul Jadhav
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 Ipca Lab Ltd, Ashok Kumar, Ketan Dhansukhlal Vyas, Dharmendra Singh, Sanjay Nandavadekar, Sanjay Bhise, Atul Jadhav filed Critical Ipca Lab Ltd
Publication of WO2005062723A2 publication Critical patent/WO2005062723A2/en
Publication of WO2005062723A3 publication Critical patent/WO2005062723A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Abstract

Disclosed herein is an improved process for the preparation of 7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline comprising of condensation reaction of 4,7 - dichloro quinoline with 5-(n-ethyl-N-2-hydroxyethyl amino)-2-pentylamine and its intermediates which comprises the reaction of protected 1-chloro-4-pentanone with substituted amine followed by deprotection of ketogroup and reductive amination yielding 5-(N-ethyl-N-2-hydroxyethyl amino)-2-pentylamine or 5 - (N,N-diethylamino) - 2 - pentylamine.
PCT/IN2004/000364 2003-11-24 2004-11-23 An improved process for the preparation of 7-chloro-4-(5-n-ehtyl-n-2-hydroxyethylamine)-2-pentyl] aminoquinoline and its intermediates WO2005062723A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1215/MUM/2003 2003-11-24
IN1213/MUM/2003 2003-11-24
IN1213MU2003 2003-11-24
IN1215MU2003 2003-11-24

Publications (2)

Publication Number Publication Date
WO2005062723A2 WO2005062723A2 (en) 2005-07-14
WO2005062723A3 true WO2005062723A3 (en) 2006-01-05

Family

ID=34740782

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2004/000364 WO2005062723A2 (en) 2003-11-24 2004-11-23 An improved process for the preparation of 7-chloro-4-(5-n-ehtyl-n-2-hydroxyethylamine)-2-pentyl] aminoquinoline and its intermediates

Country Status (1)

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WO (1) WO2005062723A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101115412B1 (en) * 2008-09-08 2012-06-12 주식회사 대희화학 New preparation of hydroxychloroquine
CN104230803B (en) * 2014-08-28 2017-02-01 重庆康乐制药有限公司 Preparation method of hydroxychloroquine sulfate
WO2019165337A1 (en) * 2018-02-26 2019-08-29 Virginia Commonwealth University High-yielding continuous flow synthesis of antimalarial drug hydroxychloroquine
CN109456266A (en) * 2018-11-12 2019-03-12 南京天际联盟医药科技有限公司 The novel preparation method of hydroxychloroquine sulfate
CN110283121A (en) * 2019-08-06 2019-09-27 华东理工大学 The synthetic method of hydroxychloroquine
CN111482178A (en) * 2020-04-15 2020-08-04 中国科学院兰州化学物理研究所 Supported nano nickel-based catalyst and preparation method and application thereof
CN111635358B (en) * 2020-06-29 2022-06-03 北京成宇化工有限公司 Preparation method of hydroxychloroquine
CN111995574A (en) * 2020-08-28 2020-11-27 西安明喆药品生产有限公司 Deuterated hydroxychloroquine derivative and pharmaceutical composition containing same
IT202000020872A1 (en) 2020-09-02 2022-03-02 Dipharma Francis Srl PROCEDURE FOR THE PREPARATION OF AN AGENT FOR THE TREATMENT OF MALARIA
CN112300071B (en) * 2020-11-25 2023-01-31 威胜生物医药(苏州)股份有限公司 Synthetic method of high-purity chloroquine phosphate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3362954A (en) * 1965-08-12 1968-01-09 Sterling Drug Inc 4-tertiary amino-lower alkylamino-quinoline carboxamides and carboxylates
US5314894A (en) * 1992-09-15 1994-05-24 Sterling Winthrop Inc. (S)-(+)-hydroxychloroquine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3362954A (en) * 1965-08-12 1968-01-09 Sterling Drug Inc 4-tertiary amino-lower alkylamino-quinoline carboxamides and carboxylates
US5314894A (en) * 1992-09-15 1994-05-24 Sterling Winthrop Inc. (S)-(+)-hydroxychloroquine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BAILEY D. ET AL.: "Quinoline Antimalarials. Folded Chloroquine", JOURNAL OF MEDICINAL CHEMISTRY, vol. 12, no. 1, January 1969 (1969-01-01), pages 184 - 185, XP002337636 *
LANGER S. ET AL.: "Inhibitors of Topoisomerase II", CLINICAL CANCER RESEARCH, vol. 5, October 1999 (1999-10-01), pages 2899 - 2907, XP002991582 *

Also Published As

Publication number Publication date
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