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GB1077974A - Quinoline compounds and a process for their production - Google Patents

Quinoline compounds and a process for their production

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Publication number
GB1077974A
GB1077974AGB2897564AGB2897564AGB1077974AGB 1077974 AGB1077974 AGB 1077974AGB 2897564 AGB2897564 AGB 2897564AGB 2897564 AGB2897564 AGB 2897564AGB 1077974 AGB1077974 AGB 1077974A
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GB
United Kingdom
Prior art keywords
compounds
formula
alkyl
phenyl
amino
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
GB2897564A
Inventor
Otto Hromatka
Otto Nieschulz
Gerhard Hackmack
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.)
CHEM FAB PROMCNTA GmbH
Original Assignee
CHEM FAB PROMCNTA GmbH
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 CHEM FAB PROMCNTA GmbHfiledCriticalCHEM FAB PROMCNTA GmbH
Priority to GB2897564ApriorityCriticalpatent/GB1077974A/en
Publication of GB1077974ApublicationCriticalpatent/GB1077974A/en
Expiredlegal-statusCriticalCurrent

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Abstract

The invention comprises compounds of the formula <FORM:1077974/C2/1> wherein each of R1 and R2 represents a hydrogen atom or a C1- 4 alkyl, phenyl-C1- 4 alkyl, C1- 4 hydroxyalkyl, C1- 4 alkoxy-C1- 4 alkyl, di-(C1- 4 alkyl)-amino-C1- 4 alkyl or C2- 5 alkoxy-carbonyl-C1- 4 alkyl group, and each of R3 and R4 represents a hydrogen or halogen atom or a C1- 4 alkyl or C1- 4 alkoxy group, non-toxic acid addition salts thereof, and their preparation by (a) reacting 1-phenyl-4-oxo-1,2,3,4-tetrahydro quinolines of the formula <FORM:1077974/C2/2> with hydroxylamine to form the corresponding 1 - phenyl - 4 hydroximino - 1,2,3,4 - tetrahydroquinolines, reducing these hydroximino compounds to the corresponding 4-amino compounds (Formula I, R1=R2=H), and, if desired, substituting one or both of the hydrogen atoms in the 4-amino group by the radicals listed above for R1 and R2, or (b) by reacting compounds of the Formula II with compounds of the formula NH2-R1 in which R1 has the meaning given above except for hydrogen, to form the corresponding 4-imino compounds, reducing these imino compounds to form the corresponding 4-mono-substituted-amino compounds (Formula I, R2=H), and, if desired, replacing the hydrogen atom of the mono-substituted-amino group by a radical listed above for R2. The free bases can be converted into the corresponding salts with non-toxic mineral or organic acids. 1 - Phenyl - 4 - oxo - 1,2,3,4 - tetrahydroquinolines of the Formula II are prepared by cyclization of the corresponding b -diphenylamino-propionic acids which are themselves prepared by reaction of the corresponding diphenylamines with b -propiolactone. b - (4,41 - Diethyl - diphenylamino) - propionic acid is characterized by its S-benzyl-isothiouronium salt. 1 - Phenyl - 4 - (31 - hydroxy-propionamido) - 1,2,3,4 - tetrahydro - quinoline is characterized by its phenyl isocyanate derivative.
GB2897564A1964-07-141964-07-14Quinoline compounds and a process for their productionExpiredGB1077974A (en)

Priority Applications (1)

Application NumberPriority DateFiling DateTitle
GB2897564AGB1077974A (en)1964-07-141964-07-14Quinoline compounds and a process for their production

Applications Claiming Priority (1)

Application NumberPriority DateFiling DateTitle
GB2897564AGB1077974A (en)1964-07-141964-07-14Quinoline compounds and a process for their production

Publications (1)

Publication NumberPublication Date
GB1077974Atrue GB1077974A (en)1967-08-02

Family

ID=10284233

Family Applications (1)

Application NumberTitlePriority DateFiling Date
GB2897564AExpiredGB1077974A (en)1964-07-141964-07-14Quinoline compounds and a process for their production

Country Status (1)

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GB (1)GB1077974A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
FR2498184A1 (en)*1981-01-161982-07-23Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF QUINOLINONES-4
WO2011067273A1 (en)*2009-12-042011-06-09F. Hoffmann-La Roche AgTetrahydroquinoline indole derivatives as monoamine reuptake inhibitors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
FR2498184A1 (en)*1981-01-161982-07-23Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF QUINOLINONES-4
EP0056763A3 (en)*1981-01-161982-08-04Rhone-Poulenc SanteProcess for the preparation of 4-quinolones
WO2011067273A1 (en)*2009-12-042011-06-09F. Hoffmann-La Roche AgTetrahydroquinoline indole derivatives as monoamine reuptake inhibitors

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