DE637429C - Process for the production of pellets in the 2-position phenylated 4-aminoquinolines - Google Patents

Process for the production of pellets in the 2-position phenylated 4-aminoquinolines

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Publication number
DE637429C
DE637429C DEJ49155D DEJ0049155D DE637429C DE 637429 C DE637429 C DE 637429C DE J49155 D DEJ49155 D DE J49155D DE J0049155 D DEJ0049155 D DE J0049155D DE 637429 C DE637429 C DE 637429C
Authority
DE
Germany
Prior art keywords
phenyl
phenylated
aminoquinolines
pyrazolone
dimethyl
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
DEJ49155D
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German (de)
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.)
HANNS JOHN DR
Original Assignee
HANNS JOHN DR
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 HANNS JOHN DR filed Critical HANNS JOHN DR
Priority to DEJ49155D priority Critical patent/DE637429C/en
Application granted granted Critical
Publication of DE637429C publication Critical patent/DE637429C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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

Description

Es wurde gefunden, daß man zu neuen in der Medizin, insbesondere als analgetische Mittel, anwendbaren, in 2-Stellung phenylierten Aminochinolinen gelangen kann, wenn man in 4-Stellung substituierte 2-Phenylchinoline oder deren Substitutionsprodukte mit in 4-Stellung substituiertem i-Phenyl-2, 3-dimethyl-5-pyrazolon unter Austritt von Halogenwasserstoff zu einem sekundären Amin kondensiert.It has been found that new ones in medicine, especially as analgesic agents, applicable aminoquinolines phenylated in the 2-position can be achieved if 2-phenylquinolines substituted in the 4-position or their Substitution products with i-phenyl-2,3-dimethyl-5-pyrazolone substituted in the 4-position condensed with the escape of hydrogen halide to form a secondary amine.

to Der Erfindung gemäß kann man beispielsweise 2-phenylierte 4-Halogenchinoline oder deren Substitutionsprodukte mit 1-Phenyl 2,3-dimethyl-4-amino-5-pyrazolon kondensieren. Gegebenenfalls kann man der Erfindung gemäß auch derart vorgehen, daß aus 2-phenylierten 4-Aminochinolinen oder deren Substitutionsprodukten und i-Phenyl-2, 3-dimethyl-4-halogen-5-pyrazolon Halogenwasserstoff abgespalten wird.According to the invention, for example, 2-phenylated 4-haloquinolines or their substitution products with 1-phenyl 2,3-dimethyl-4-amino-5-pyrazolone condense. Optionally, you can proceed according to the invention in such a way that from 2-phenylated 4-aminoquinolines or their substitution products and i-phenyl-2,3-dimethyl-4-halogen-5-pyrazolone Hydrogen halide is split off.

Die Kondensation kann unter Heranziehung an sich bekannter Methoden mit oder ohne Anwendung von Druck, Wärme oder Lösungsmitteln, bei Gegenwart oder Abwesenheit von die Abspaltung des Halogenwasserstoffes fördernden bzw. diesen bindenden Mitteln erfolgen. Die der Erfindung gemäß gewonnenen Produkte erlangen dadurch besondere Bedeutung, weil man sie durch weitere Umsetzung in eine leicht lösliche Form überführen kann.The condensation can be carried out using methods known per se, with or without application of pressure, heat or solvents, in the presence or absence of promoting the elimination of the hydrogen halide or these binding means. The products obtained according to the invention gain special importance because they can be converted into a can convert easily soluble form.

Beispiel 1example 1

40 Teile 2-Phenyl-4-chlorchinolin und 28 Teile i-Phenyl-2,3-dimethyl-4-amino-5-pyrazolon werden im Einschmelzrohr mehrere Stunden auf 100 bis 120° erhitzt. Der Inhalt der Bombe wird dann mit Natriumcarbonat verrieben, halogenfrei gewaschen, getrocknet und aus Methylalkohol umkristallisiert. Das so erhaltene i-Phenyl-2, 3-dimethyl-4- [2'-phenylchinolyl-4'] amino-5-pyrazolon schmilzt bei 247 ° und löst sich schwer in Benzol, Toluol und Xylol, fast nicht in Äther. Das Pikrat kommt aus Alkohol in kleinen Kristallen, die bei 180 ° schmelzen.40 parts of 2-phenyl-4-chloroquinoline and 28 parts of i-phenyl-2,3-dimethyl-4-amino-5-pyrazolone are used heated in the melting tube for several hours at 100 to 120 °. The contents of the bomb is then triturated with sodium carbonate, washed halogen-free, dried and extracted from methyl alcohol recrystallized. The i-phenyl-2,3-dimethyl-4- [2'-phenylquinolyl-4 '] amino-5-pyrazolone thus obtained melts at 247 ° and is difficult to dissolve in benzene, toluene and xylene, almost not in ether. The picrate comes from alcohol in small crystals that melt at 180 °.

Beispiel 2Example 2

Wie Beispiel i, mit dem Unterschiede, daß das 2-Phenyl-4-chlorchinolin durch 2-Phenyl-6-methyl-4-bromchinoHn ersetzt wird.Like example i, with the difference that the 2-phenyl-4-chloroquinoline by 2-phenyl-6-methyl-4-bromquinoline is replaced.

Beispiel 3Example 3

Ausgangsstoffe wie in Beispiel 1 oder 2, mit dem Unterschiede, daß nicht im Einschmelzrohr gearbeitet, sondern im offenen Gefäß in amylalkoholischer Lösung auf Wasserbadtemperatur erhitzt wird.Starting materials as in Example 1 or 2, with the difference that not in the melting tube worked, but in an open vessel in amyl alcoholic solution at water bath temperature is heated.

Beispiel 4Example 4

Molekulare Mengen 2-Phenyl-6-methyl-4-aminochinolin und i-Phenyl-2,3-dimethyl-4-brom-5-pyrazolon, gelöst in Amylalkohol, werden nach Hinzufügen von wasserfreiem Natriumacetat etwa 15 Stunden im Einschmelzrohr auf 150 ° erhitzt; dann wird der Inhalt der Bombe wie in Beispiel 1 aufgearbeitet.Molecular amounts of 2-phenyl-6-methyl-4-aminoquinoline and i-phenyl-2,3-dimethyl-4-bromo-5-pyrazolone, dissolved in amyl alcohol, after adding anhydrous sodium acetate heated to 150 ° in a melt-down tube for about 15 hours; then the contents of the bomb worked up as in Example 1.

Es ist wohl bereits vorgeschlagen worden, halogensubstituierte Phenylchinoline mit aliphatischen oder heterocyclischen Aminbasen umzusetzen. Bei diesen Verfahren wurden je-It has probably already been proposed to halogen-substituted phenylquinolines with aliphatic or to implement heterocyclic amine bases. In these proceedings, each

doch nicht Abkömmlinge des i-Phenyl-2, 3-dimethyl-5-pyrazolons»-verwendet, und die nach diesen bekannten Verfahren "hergestellten Produkte zeigten keine'medizinische Wirksamkeit:! but not derivatives of i-phenyl-2, 3-dimethyl-5-pyrazolons »-used, and the products manufactured according to these known processes showed no medical effectiveness :!

Claims (1)

Patentansprüche: '■ "*■-"·Claims: '■ "* ■ -" · i. Verfahren zur Herstellung von Abkömmlingen in 2-Stellung phenylierter 4-Aininochinoline, dadurch gekennzeichnet, daß man in 4-Stellung substituierte 2-Phenylchinoline oder deren Substitutionsprodukte mit in 4-Stellung substituiertem i-Phenyl-2,3-dimethyl-5-pyrazolon unter Austritt von Halogenwasserstoff zu einem sekundären J Amin kondensiert.i. Process for the preparation of derivatives of 4-aminoquinolines phenylated in the 2-position, characterized in that 2-phenylquinolines substituted in the 4-position or their substitution products with i-phenyl-2,3-dimethyl-5-pyrazolone substituted in the 4-position are included leakage of hydrogen halide to a secondary amine J condensed. "%& 2. Verfahren nach Anspruch 1, dadurch , !^gekennzeichnet, daß man in 2-Stellung phe-Ä-P'nyjierte 4-Halogenchinoline oder deren Sub-■* sfftutionsprodukte mit i-Phenyl-2, 3-dime- *' thyl-4-amino-5-pyrazolon kondensiert. "% & 2. Process according to claim 1, characterized in that in the 2-position phe-Ä-P'nyjierte 4-haloquinolines or their substitution products with i-phenyl-2, 3-dimen- * ' thyl-4-amino-5-pyrazolone condensed. 3. Verfahren nach Anspruch 1 und 2, dadurch gekennzeichnet, daß man in 2-Stellung phenylierte 4-Aminochinoline oder deren Substitutionsprodukte mit i-Phenyl-2, 3-dimethyl-4-halogen-5-pyrazolon kondensiert.3. The method according to claim 1 and 2, characterized in that one is in the 2-position phenylated 4-aminoquinolines or their substitution products with i-phenyl-2,3-dimethyl-4-halogen-5-pyrazolone condensed.
DEJ49155D 1934-03-04 1934-03-04 Process for the production of pellets in the 2-position phenylated 4-aminoquinolines Expired DE637429C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEJ49155D DE637429C (en) 1934-03-04 1934-03-04 Process for the production of pellets in the 2-position phenylated 4-aminoquinolines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEJ49155D DE637429C (en) 1934-03-04 1934-03-04 Process for the production of pellets in the 2-position phenylated 4-aminoquinolines

Publications (1)

Publication Number Publication Date
DE637429C true DE637429C (en) 1936-10-28

Family

ID=7206619

Family Applications (1)

Application Number Title Priority Date Filing Date
DEJ49155D Expired DE637429C (en) 1934-03-04 1934-03-04 Process for the production of pellets in the 2-position phenylated 4-aminoquinolines

Country Status (1)

Country Link
DE (1) DE637429C (en)

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