GB1142981A - Phenylisopropylamine derivatives - Google Patents

Phenylisopropylamine derivatives

Info

Publication number
GB1142981A
GB1142981A GB593066A GB593066A GB1142981A GB 1142981 A GB1142981 A GB 1142981A GB 593066 A GB593066 A GB 593066A GB 593066 A GB593066 A GB 593066A GB 1142981 A GB1142981 A GB 1142981A
Authority
GB
United Kingdom
Prior art keywords
formula
hydrogen
group
compound
proviso
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
GB593066A
Inventor
Zoltan Ecsery
Jozsef Knoll
Ildiko Kosa
Ildiko Sandor
Eva Somfai
Sandor Torok
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of GB1142981A publication Critical patent/GB1142981A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1,142,981. Phenyl-isopropylamine derivatives. CHINOIN GYOGYSZER-ES VEGYESZETI TERMEKEK GYARA RT. 10 Feb., 1966, No. 5930/66. Addition to 1,031,425. Heading C2C. [Also in Division A5] The invention comprises (a) compounds of the Formula I, in which R<SP>2</SP> is hydrogen, or a propyl, propenyl or propynyl group which may be substituted by a halogen atom or a hydroxy group, R<SP>3</SP> is hydrogen, halogen, nitro, amino or diazonium, R<SP>4</SP> is fluorine, bromine, iodine, nitro, amino or diazonium and, if R<SP>3</SP> is not hydrogen, R<SP>4</SP> may also be hydrogen, R<SP>1</SP> is C 1-7 alkyl with the proviso that if R<SP>3</SP> and/or R<SP>4</SP> is fluorine, then R<SP>1</SP> is alkyl having at least 3 carbon atoms, and with the further proviso that if R<SP>3</SP> is nitro, amino, diazonium or halogen and R<SP>3</SP> is hydrogen, then R<SP>1</SP> is alkyl having at least 2 carbon atoms, and with the further proviso that if R<SP>2</SP> is hydrogen, then R<SP>3</SP> cannot be chlorine, bromine or fluorine, and their acid addition salts, (b) the preparation of compounds of Formula I in which R<SP>1</SP> to R<SP>4</SP> have the same meanings as given in (a) with the exception that the last proviso does not apply, by (A) reacting a phenylacetone of Formula II with an amine of formula R<SP>1</SP>R<SP>2</SP>NH with simultaneous or subsequent reduction, R<SP>1</SP> to R<SP>4</SP> having the same meanings as stated above with the proviso that if R<SP>2</SP> is hydrogen, then R<SP>3</SP> is not chlorine, bromine or fluorine, or (B) reacting a compound of Formula III with a compound of formula Y-R<SP>2</SP>, where one of X and Y is -NHR<SP>1</SP> and the other is halogen or a sulphonic ester group, and R<SP>1</SP> to R<SP>4</SP> have the same meanings as stated above with the proviso that R<SP>2</SP> is not hydrogen if X is -NHR<SP>1</SP>, or (C) reacting a compound of Formula IV with a compound of formula R<SP>5</SP>-CO-R<SP>2</SP>, where R<SP>5</SP> is hydrogen or alkyl, R<SP>2</SP> is ethyl, vinyl or ethynyl, and R<SP>1</SP>, R<SP>3</SP> and R<SP>4</SP> have the same meanings as stated above, or (D) reacting a compound of Formula IV with formaldehyde and acetylene to produce a compound of Formula I in which R<SP>2</SP> is propynyl and, if desired, transforming the propynyl group by reduction and/or halogenation to a propyl, halopropyl, propenyl, halopropenyl or halopropyl group, or (E) performing reaction (A), (B), (C) or (D) and modifying or forming one of the substituents R<SP>3</SP>, R<SP>4</SP> on the aromatic nucleus by nitration, reduction of a nitro group to an amino group, halogenation, diazotization of an amino group, or Sandmeyer conversion of a diazo group to a halogen atom, and (c) pharmaceutical compositions comprising a compound of Formula I, in which R<SP>1</SP> to R<SP>4</SP> have the same meanings as in (a) with the exception that none of the provisos apply, together with a carrier.
GB593066A 1962-03-30 1966-02-10 Phenylisopropylamine derivatives Expired GB1142981A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HUCI000941 1962-03-30

Publications (1)

Publication Number Publication Date
GB1142981A true GB1142981A (en) 1969-02-12

Family

ID=10994370

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1197663A Expired GB1031425A (en) 1962-03-30 1963-03-26 New aralkylamines and their preparation
GB593066A Expired GB1142981A (en) 1962-03-30 1966-02-10 Phenylisopropylamine derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1197663A Expired GB1031425A (en) 1962-03-30 1963-03-26 New aralkylamines and their preparation

Country Status (1)

Country Link
GB (2) GB1031425A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985005617A1 (en) * 1984-05-31 1985-12-19 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. Phenylisopropylamine derivative and its preparation
WO1988002254A1 (en) * 1986-09-25 1988-04-07 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. New psychostimulant agent
US5220068A (en) * 1986-09-25 1993-06-15 Chinoin Gyogyszer - Es Vegyeszeti Termekek Gyara Rt. Psychostimulant agent
GB2233558B (en) * 1989-06-02 1993-12-15 Wyeth John & Brother Ltd Psychotropic use of aromatic amines

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU174692B (en) * 1975-12-29 1980-03-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing secondary and tertiary derivatives of 2-/2-furyl/-ethylamine
HU197510B (en) * 1986-12-19 1989-04-28 Chinoin Gyogyszer Es Vegyeszet Process for producing pharmaceutical composition containing phenyl-alkyl-amine derivatives, against motion-sick
GB2280604B (en) * 1993-07-02 1997-04-30 Resource Medical Limited Processing of active agents
IES61604B2 (en) * 1993-12-16 1994-11-16 Russinsky Ltd A process for producing pharmaceutical compounds
IT201700008702A1 (en) 2017-01-26 2018-07-26 Dipharma Francis Srl METHOD OF SYNTHESIS OF SELEGILINA BASE

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985005617A1 (en) * 1984-05-31 1985-12-19 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. Phenylisopropylamine derivative and its preparation
DE3590241C2 (en) * 1984-05-31 1991-08-01 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt., Budapest, Hu
AT394552B (en) * 1984-05-31 1992-05-11 Chinoin Gyogyszer Es Vegyeszet METHOD FOR PRODUCING THE NEW N- (2- (4-FLUOR-PHENYL) -1-METHYL) -AETHYL-N-METHYL-PROPINYLAMINE AND ISOMERS AND SALTS THEREOF
WO1988002254A1 (en) * 1986-09-25 1988-04-07 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. New psychostimulant agent
US5220068A (en) * 1986-09-25 1993-06-15 Chinoin Gyogyszer - Es Vegyeszeti Termekek Gyara Rt. Psychostimulant agent
GB2233558B (en) * 1989-06-02 1993-12-15 Wyeth John & Brother Ltd Psychotropic use of aromatic amines

Also Published As

Publication number Publication date
GB1031425A (en) 1966-06-02

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