GB1142981A - Phenylisopropylamine derivatives - Google Patents
Phenylisopropylamine derivativesInfo
- 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
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.
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)
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)
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 |
-
1963
- 1963-03-26 GB GB1197663A patent/GB1031425A/en not_active Expired
-
1966
- 1966-02-10 GB GB593066A patent/GB1142981A/en not_active Expired
Cited By (6)
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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