WO2005062724A3 - Novel process for the preparation of aminoadamantane derivatives - Google Patents

Novel process for the preparation of aminoadamantane derivatives Download PDF

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Publication number
WO2005062724A3
WO2005062724A3 PCT/IN2004/000440 IN2004000440W WO2005062724A3 WO 2005062724 A3 WO2005062724 A3 WO 2005062724A3 IN 2004000440 W IN2004000440 W IN 2004000440W WO 2005062724 A3 WO2005062724 A3 WO 2005062724A3
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WO
WIPO (PCT)
Prior art keywords
formula
compound
preparation
novel process
aminoadamantane derivatives
Prior art date
Application number
PCT/IN2004/000440
Other languages
French (fr)
Other versions
WO2005062724A2 (en
Inventor
Nagarajan Periyandi
Srinivasu Kilaru
Rajamannar Thennati
Original Assignee
Sun Pharmaceutical Ind Ltd
Nagarajan Periyandi
Srinivasu Kilaru
Rajamannar Thennati
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 Sun Pharmaceutical Ind Ltd, Nagarajan Periyandi, Srinivasu Kilaru, Rajamannar Thennati filed Critical Sun Pharmaceutical Ind Ltd
Publication of WO2005062724A2 publication Critical patent/WO2005062724A2/en
Publication of WO2005062724A3 publication Critical patent/WO2005062724A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
    • C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Abstract

A novel process for the preparation of aminoadamantane derivatives, compound of formula (I) (wherein R1, R2 are selected from C1-4 linear and branched alkyl & R3 is selected from hydrogen, C1-4 linear and branched alkyl) said process comprising a)brominating compound of formula (IIa), hydrolysing and isolating compound of formula (II d). b) converting compound of formula (II d) to compound of formula (II c), and c) deacetylating compound of formula (II c) to yield compound of formula (I).
PCT/IN2004/000440 2003-12-31 2004-12-30 Novel process for the preparation of aminoadamantane derivatives WO2005062724A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1336MU2003 2003-12-31
IN1336/MUM/2003 2003-12-31

Publications (2)

Publication Number Publication Date
WO2005062724A2 WO2005062724A2 (en) 2005-07-14
WO2005062724A3 true WO2005062724A3 (en) 2006-04-06

Family

ID=34717599

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2004/000440 WO2005062724A2 (en) 2003-12-31 2004-12-30 Novel process for the preparation of aminoadamantane derivatives

Country Status (1)

Country Link
WO (1) WO2005062724A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1836157E (en) 2005-01-11 2009-11-24 Teva Pharm Fine Chemicals Srl Process for the preparation of 1-amino-3,5-dimethyladamantane hydrochloride
ITMI20050833A1 (en) * 2005-05-10 2006-11-11 A M S A S P A Anonima Materie Sintetiche Affini NEW PROCEDURE FOR THE SYNTHESIS OF AMINOADAMANTANI
ATE541827T1 (en) * 2006-02-21 2012-02-15 Hexal Ag METHOD FOR PRODUCING ADAMANTANAMINES
WO2007132476A2 (en) * 2006-05-15 2007-11-22 Matrix Laboratories Limited A process for the preparation of memantine hydrochloride
WO2010083996A1 (en) * 2009-01-21 2010-07-29 Merz Pharma Gmbh & Co. Kgaa A process for preparing memantine
JP2013505902A (en) * 2009-09-28 2013-02-21 メルツ ファーマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディト ゲゼルシャフト アウフ アクティーン Method for preparing neramexane or a salt thereof
RU2510962C2 (en) * 2012-06-19 2014-04-10 Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук Method of obtaining 1,3-dimethyladamantan-5-ol
US9452971B2 (en) 2013-01-23 2016-09-27 Mitsubishi Gas Chemical Company, Inc. Manufacturing process for memantine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3450761A (en) * 1967-03-30 1969-06-17 Sun Oil Co 1-aminoethyldimethyladamantane
SU1221866A1 (en) * 1984-03-27 1990-06-23 Институт Органической Химии Ан Усср Method of obtaining 1-oxyderivatives of adamantane, its methyl-substituted or bicyclo/3,3-1/ nonane

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3450761A (en) * 1967-03-30 1969-06-17 Sun Oil Co 1-aminoethyldimethyladamantane
SU1221866A1 (en) * 1984-03-27 1990-06-23 Институт Органической Химии Ан Усср Method of obtaining 1-oxyderivatives of adamantane, its methyl-substituted or bicyclo/3,3-1/ nonane

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [online] GERZON K ET AL: "Adamantyl group in medical agents. I. Hypoglycemic N-arylsulfonyl-N-adamantylureas.", Database accession no. (1964:23043) *
DATABASE CAPLUS [online] ZOU Y ET AL: "Synthesis of memantine hydrochloride.", Database accession no. (2003:1011883) *
DATABASE CASREACT [online] Database accession no. (141:53977) *
JOURNAL OF MEDICINAL CHEMISTRY., vol. 6, no. 6, 1963, pages 760 - 763 *
ZHONGGUO YIYAO GONGYE ZAZHI., vol. 34, no. 5, 2003, pages 213 - 214 *

Also Published As

Publication number Publication date
WO2005062724A2 (en) 2005-07-14

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