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

Quinoline compounds and a process for their production

Info

Publication number
GB1077974A
GB1077974A GB2897564A GB2897564A GB1077974A GB 1077974 A GB1077974 A GB 1077974A GB 2897564 A GB2897564 A GB 2897564A GB 2897564 A GB2897564 A GB 2897564A GB 1077974 A GB1077974 A GB 1077974A
Authority
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 GmbH filed Critical CHEM FAB PROMCNTA GmbH
Priority to GB2897564A priority Critical patent/GB1077974A/en
Publication of GB1077974A publication Critical patent/GB1077974A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Landscapes

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

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.
GB2897564A 1964-07-14 1964-07-14 Quinoline compounds and a process for their production Expired GB1077974A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2897564A GB1077974A (en) 1964-07-14 1964-07-14 Quinoline compounds and a process for their production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2897564A GB1077974A (en) 1964-07-14 1964-07-14 Quinoline compounds and a process for their production

Publications (1)

Publication Number Publication Date
GB1077974A true GB1077974A (en) 1967-08-02

Family

ID=10284233

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2897564A Expired GB1077974A (en) 1964-07-14 1964-07-14 Quinoline compounds and a process for their production

Country Status (1)

Country Link
GB (1) GB1077974A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2498184A1 (en) * 1981-01-16 1982-07-23 Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF QUINOLINONES-4
WO2011067273A1 (en) * 2009-12-04 2011-06-09 F. Hoffmann-La Roche Ag Tetrahydroquinoline indole derivatives as monoamine reuptake inhibitors

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2498184A1 (en) * 1981-01-16 1982-07-23 Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF QUINOLINONES-4
EP0056763A2 (en) * 1981-01-16 1982-07-28 Rhone-Poulenc Sante Process for the preparation of 4-quinolinones
EP0056763A3 (en) * 1981-01-16 1982-08-04 Rhone-Poulenc Sante Process for the preparation of 4-quinolones
WO2011067273A1 (en) * 2009-12-04 2011-06-09 F. Hoffmann-La Roche Ag Tetrahydroquinoline indole derivatives as monoamine reuptake inhibitors

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