GB1413070A - Process for the production of - norfenfluramine and - fenfluramine and salts thereof - Google Patents

Process for the production of - norfenfluramine and - fenfluramine and salts thereof

Info

Publication number
GB1413070A
GB1413070A GB3592373A GB3592373A GB1413070A GB 1413070 A GB1413070 A GB 1413070A GB 3592373 A GB3592373 A GB 3592373A GB 3592373 A GB3592373 A GB 3592373A GB 1413070 A GB1413070 A GB 1413070A
Authority
GB
United Kingdom
Prior art keywords
norfenfluramine
prepared
group
salt
formula
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.)
Expired
Application number
GB3592373A
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB3592373A priority Critical patent/GB1413070A/en
Publication of GB1413070A publication Critical patent/GB1413070A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
    • 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
    • C07C211/27—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 having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • 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

Landscapes

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

Abstract

1413070 (-)-Norfenfluramine BEECHAM GROUP Ltd 18 July 1974 [27 July 1973] 35923/73 Heading C2C (-)-Norfenfluramine or a salt thereof may be prepared by hydrogenating the novel compound of Formula (I) or a salt thereof: where R is a phenyl group, optionally substituted in the meta- or para-positions by a non- reactive group that does not interfere with the hydrogenation, the carbon atom marked with one asterisk has the same configuration as (-)-norfenfluramine and the carbon atom marked with two asterisks has the configuration found in (+ )-a-methylbenzylamine. The compound of Formula (I) may be prepared by reducing a compound of Formula II or a salt thereof: which may itself be prepared by reacting l-(mtrifluoromethylphenyl)propan-2-one with (+ )- α-methylbenzylamine. (-)-Fenfluramine may be prepared by the acetylation of (-)-norfenfluramine in conventional manner followed by reduction of the acetyl group to an ethyl group.
GB3592373A 1973-07-27 1973-07-27 Process for the production of - norfenfluramine and - fenfluramine and salts thereof Expired GB1413070A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3592373A GB1413070A (en) 1973-07-27 1973-07-27 Process for the production of - norfenfluramine and - fenfluramine and salts thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3592373A GB1413070A (en) 1973-07-27 1973-07-27 Process for the production of - norfenfluramine and - fenfluramine and salts thereof

Publications (1)

Publication Number Publication Date
GB1413070A true GB1413070A (en) 1975-11-05

Family

ID=10383048

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3592373A Expired GB1413070A (en) 1973-07-27 1973-07-27 Process for the production of - norfenfluramine and - fenfluramine and salts thereof

Country Status (1)

Country Link
GB (1) GB1413070A (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0875498A2 (en) * 1997-04-28 1998-11-04 Alfa Chemicals Italiana S.r.l. Process for the production of the isomers (R) and (S)-Alpha-methyl-3-(trifluoromethyl)benzeneethanamine
WO2014177676A1 (en) 2013-05-03 2014-11-06 Katholieke Universiteit Leuven Fenfluramine for use in the treatment of dravet syndrome
WO2018206924A1 (en) 2017-05-09 2018-11-15 Zogenix International Limited Methods of treating doose syndrome using fenfluramine
WO2019067413A1 (en) 2017-09-26 2019-04-04 Zogenix International Limited Use of fenfluramine formulation in reducing number and frequencies of convulsive seizures in patient populations
WO2019067405A2 (en) 2017-09-26 2019-04-04 Zogenix International Limited Ketogenic diet compatible fenfluramine formulation
WO2019067419A1 (en) 2017-09-26 2019-04-04 Zogenix International Limited Improvement in cognitive function with fenfluramine
WO2020014075A1 (en) 2018-07-10 2020-01-16 Zogenix International Limited Fenfluramine for use for treating epilepsy or epileptic encephalopathy in patients without pulmonary hypertension
WO2020105005A1 (en) 2018-11-19 2020-05-28 Zogenix International Limited Methods of treating rett syndrome using fenfluramine
WO2021053389A1 (en) 2019-09-17 2021-03-25 Zogenix International Limited Methods of treating epileptic patients with fenfluramine
WO2021156437A1 (en) 2020-02-05 2021-08-12 Zogenix International Limited Fenfluramine for use in treating patients with lennox-gastaut syndrome
WO2022013425A1 (en) 2020-07-17 2022-01-20 Zogenix International Limited Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (sars-cov-2)
US11634377B2 (en) 2015-12-22 2023-04-25 Zogenix International Limited Fenfluramine compositions and methods of preparing the same
US11673852B2 (en) 2015-12-22 2023-06-13 Zogenix International Limited Metabolism resistant fenfluramine analogs and methods of using the same
US11759440B2 (en) 2016-08-24 2023-09-19 Zogenix International Limited Formulation for inhibiting formation of 5-HT2B agonists and methods of using same

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0875498A3 (en) * 1997-04-28 2000-07-26 Alfa Chemicals Italiana S.r.l. Process for the production of the isomers (R) and (S)-Alpha-methyl-3-(trifluoromethyl)benzeneethanamine
EP0875498A2 (en) * 1997-04-28 1998-11-04 Alfa Chemicals Italiana S.r.l. Process for the production of the isomers (R) and (S)-Alpha-methyl-3-(trifluoromethyl)benzeneethanamine
WO2014177676A1 (en) 2013-05-03 2014-11-06 Katholieke Universiteit Leuven Fenfluramine for use in the treatment of dravet syndrome
EP3329909A1 (en) 2013-05-03 2018-06-06 Katholieke Universiteit Leuven KU Leuven Research & Development Fenfluramine for use in the treatment of dravet syndrome
US11634377B2 (en) 2015-12-22 2023-04-25 Zogenix International Limited Fenfluramine compositions and methods of preparing the same
US11673852B2 (en) 2015-12-22 2023-06-13 Zogenix International Limited Metabolism resistant fenfluramine analogs and methods of using the same
US11786487B2 (en) 2016-08-24 2023-10-17 Zogenix International Limited Formulation for inhibiting formation of 5-HT2B agonists and methods of using same
US11759440B2 (en) 2016-08-24 2023-09-19 Zogenix International Limited Formulation for inhibiting formation of 5-HT2B agonists and methods of using same
WO2018206924A1 (en) 2017-05-09 2018-11-15 Zogenix International Limited Methods of treating doose syndrome using fenfluramine
WO2019067413A1 (en) 2017-09-26 2019-04-04 Zogenix International Limited Use of fenfluramine formulation in reducing number and frequencies of convulsive seizures in patient populations
WO2019067405A2 (en) 2017-09-26 2019-04-04 Zogenix International Limited Ketogenic diet compatible fenfluramine formulation
WO2019067419A1 (en) 2017-09-26 2019-04-04 Zogenix International Limited Improvement in cognitive function with fenfluramine
WO2020014075A1 (en) 2018-07-10 2020-01-16 Zogenix International Limited Fenfluramine for use for treating epilepsy or epileptic encephalopathy in patients without pulmonary hypertension
WO2020105005A1 (en) 2018-11-19 2020-05-28 Zogenix International Limited Methods of treating rett syndrome using fenfluramine
WO2021053389A1 (en) 2019-09-17 2021-03-25 Zogenix International Limited Methods of treating epileptic patients with fenfluramine
WO2021156437A1 (en) 2020-02-05 2021-08-12 Zogenix International Limited Fenfluramine for use in treating patients with lennox-gastaut syndrome
US11612574B2 (en) 2020-07-17 2023-03-28 Zogenix International Limited Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2)
WO2022013425A1 (en) 2020-07-17 2022-01-20 Zogenix International Limited Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (sars-cov-2)

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Legal Events

Date Code Title Description
414F Notice of opposition given (sect. 14/1949)
414C Case decided by the comptroller ** grants refused (sect. 14/1949)
CSNS Application of which complete specification have been accepted and published, but patent is not sealed