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WO2002036540A3 - PROCESS FOR PREPARATION OF β-PHENETHYLAMINE DERIVATIVE - Google Patents

PROCESS FOR PREPARATION OF β-PHENETHYLAMINE DERIVATIVE Download PDF

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Publication number
WO2002036540A3
WO2002036540A3 PCT/IB2001/001996 IB0101996W WO0236540A3 WO 2002036540 A3 WO2002036540 A3 WO 2002036540A3 IB 0101996 W IB0101996 W IB 0101996W WO 0236540 A3 WO0236540 A3 WO 0236540A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
sibutramine
imine
cyclobutyl
chlorophenyl
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/IB2001/001996
Other languages
French (fr)
Other versions
WO2002036540A2 (en
Inventor
Sharad Kumar Vyas
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to AU2002210816A priority Critical patent/AU2002210816A1/en
Publication of WO2002036540A2 publication Critical patent/WO2002036540A2/en
Publication of WO2002036540A3 publication Critical patent/WO2002036540A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/28—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with other reducing agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

A process for the production of Sibutramine i.e. N-1-[1-(4-chlorophenyl) cyclobutyl]-3-methylbutyl-N, N-dimethylamine of formula (I) comprising the steps of: (a) reacting a nitrile, 1-(4-chlorophenyl) cyclobutyl carbonitrile of formula (III) with a Grignard reagent, namely isobutyl magnesium bromide to produce the magnesium complex of formula (IV); (b) cleaving the magnesium complex of formula (IV) under basic conditions to form an imine of formula (VIII); (c) reducing the imine of formula (VIII) by a metal hydride to obtain an amine of the formula (VII), and (d) converting the amine (VII) first to its hydrochloride and then to Sibutramine of formula (I) by Eschweiler Clarke methylation.
PCT/IB2001/001996 2000-11-02 2001-10-25 PROCESS FOR PREPARATION OF β-PHENETHYLAMINE DERIVATIVE Ceased WO2002036540A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002210816A AU2002210816A1 (en) 2000-11-02 2001-10-25 Process for preparation of beta-phenethylamine derivative

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN612CA2000 2000-11-02
IN612/CAL/2000 2000-11-02

Publications (2)

Publication Number Publication Date
WO2002036540A2 WO2002036540A2 (en) 2002-05-10
WO2002036540A3 true WO2002036540A3 (en) 2002-07-18

Family

ID=11096985

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2001/001996 Ceased WO2002036540A2 (en) 2000-11-02 2001-10-25 PROCESS FOR PREPARATION OF β-PHENETHYLAMINE DERIVATIVE

Country Status (2)

Country Link
AU (1) AU2002210816A1 (en)
WO (1) WO2002036540A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2501321C (en) * 2002-10-05 2008-07-08 Hanmi Pharm. Co., Ltd. Pharmaceutical composition comprising crystalline sibutramine methanesulfonate hemihydrate
KR100536750B1 (en) * 2002-10-05 2005-12-16 한미약품 주식회사 Pharmaceutical composition comprising crystalline hemihydrate of sibutramine methanesulfonate
EP2066329B1 (en) 2006-09-15 2017-09-06 Reviva Pharmaceuticals, Inc. Synthesis, methods of using, and compositions of cyclobutylmethylamines
WO2012003501A2 (en) 2010-07-02 2012-01-05 Reviva Pharmaceuticals, Inc. Compositions, synthesis, and methods of using cycloalkylmethylamine derivatives
WO2013102195A1 (en) 2011-12-30 2013-07-04 Reviva Pharmaceuticals, Inc. Compositions, synthesis, and methods of using phenylcycloalkylmethylamine derivatives
CN106565007B (en) * 2016-11-09 2019-10-11 烟台索山机械有限公司 A kind of degreaser of ternary composite flooding water extraction and preparation method thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2098602A (en) * 1981-04-06 1982-11-24 Boots Co Plc Therapeutic agents
EP0191542A1 (en) * 1985-01-17 1986-08-20 The Boots Company PLC Arylcyclobutylalkyl amines and their use as antidepressive medicines
WO2000010551A2 (en) * 1998-08-24 2000-03-02 Sepracor Inc. Methods of using and compositions comprising dopamine reuptake inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2098602A (en) * 1981-04-06 1982-11-24 Boots Co Plc Therapeutic agents
EP0191542A1 (en) * 1985-01-17 1986-08-20 The Boots Company PLC Arylcyclobutylalkyl amines and their use as antidepressive medicines
WO2000010551A2 (en) * 1998-08-24 2000-03-02 Sepracor Inc. Methods of using and compositions comprising dopamine reuptake inhibitors

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
G. OM REDDY ET AL.: "A study and identification of potential by-products of sibutramine", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 3, 1999, pages 488 - 492, XP001040382 *
JEFFERY J E ET AL: "SYNTHESIS OF SIBUTRAMINE, A NOVEL CYCLOBUTYLALKYLAMINE USEFUL IN THE TREATMENT OF OBESITY, AND ITS MAJOR HUMAN METABOLITES", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 21, 1996, pages 2583 - 2589, XP000891897, ISSN: 1472-7781 *
SHEN JING ET AL.: "Improvement on synthesis of sibutramine", CHINESE JOURNAL OF MEDICINAL CHEMISTRY, vol. 10, no. 2, June 2000 (2000-06-01), pages 129 - 130,140, XP001040380 *

Also Published As

Publication number Publication date
AU2002210816A1 (en) 2002-05-15
WO2002036540A2 (en) 2002-05-10

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