DE698007C - Process for the preparation of readily water-soluble compounds of 8-oxyquinoline - Google Patents

Process for the preparation of readily water-soluble compounds of 8-oxyquinoline

Info

Publication number
DE698007C
DE698007C DE1938B0183346 DEB0183346D DE698007C DE 698007 C DE698007 C DE 698007C DE 1938B0183346 DE1938B0183346 DE 1938B0183346 DE B0183346 D DEB0183346 D DE B0183346D DE 698007 C DE698007 C DE 698007C
Authority
DE
Germany
Prior art keywords
oxyquinoline
preparation
soluble compounds
readily water
water
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
DE1938B0183346
Other languages
German (de)
Inventor
Dr Phil Ferdinand Hoffmann
Dr Med Peter Marquardt
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.)
Takeda GmbH
Original Assignee
Byk Gulden Lomberg Chemische Fabrik 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 Byk Gulden Lomberg Chemische Fabrik GmbH filed Critical Byk Gulden Lomberg Chemische Fabrik GmbH
Priority to DE1938B0183346 priority Critical patent/DE698007C/en
Application granted granted Critical
Publication of DE698007C publication Critical patent/DE698007C/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
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof

Landscapes

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

Description

Verfahren zur Herstellung leicht wasserlöslicher Verbindungen von 8-Oxychinolin Es ist bekannt, daß 8-Oxychinolin sehr schwer wasserlöslich ist. In der Human- und Veterinärmedizin werden daher nur seine Verbindungen, z. B. mit Sulfosalicylsäure und Phenolsulfosäuren, oder ein Schwefelsäureester verwendet, die leicht wasserlöslich 'sind. Diese Verbindungen sind verhältnismäßig umständlich herzustellen. Es wurde nun gefunden, daß man - in einfacher Weise zu neuen, wertvollen Verbindungen des 8-Oxychinolins gelangt, wenn man dieses mit Camphosulfonsäuren in etwa molaren Mengen umsetzt.Process for the preparation of readily water-soluble compounds of 8-Oxyquinoline It is known that 8-Oxyquinoline is very sparingly soluble in water. In human and veterinary medicine are therefore only its connections, z. B. with sulfosalicylic acid and phenolsulfonic acids, or a sulfuric acid ester, are used, which are easily soluble in water 'are. These connections are relatively cumbersome to make. It was now found that - in a simple way to new, valuable connections of the 8-Oxyquinoline is obtained when this is mixed with camphosulfonic acids in approximately molar amounts implements.

Die patentbegründenden Vorteile des neuen Verfahrens gegenüber dem Stand der Technik werden darin gesehen, daß die Umsetzung unter einfachsten Bedingungen, z. B. schon beim Verreiben bei gewöhnlicher Temperatur, möglich ist, daß auch der die Wasserlöslichkeit bewirkende Umsetzungsteilnehmer eine spezifische therapeutische Wirkung hat und-- schließlich. darin, daß die neuen Verbindungen neben einer guten Wasserlöslichkeit eine gewisse Lipoidlöslichkeit aufweisen. Diese Lipoidlöslichkeit einer an sich leicht wasserlöslichen Verbindung ist in therapeutischer Hinsicht besonders vorteilhaft: Die neuen Verbindungen stellen vermutlich Salze dar. Das campho-io-sulfonsaure 8-Oxychinolin erweist sich z. B. durch seine physikalischen Eigenschäften als einheitliche Verbindung (Schmelzpunkt 205 ", Mischschmelzpunkt mit Campho-io-Sulfonsäure iog°). Es handelt sich also trotz der Einfachheit des Verfahrens um definierte Umsetzungsprodukte und nicht etwa nur um ,mechanische Gemische der Ausgangsstoffe.The patent-establishing advantages of the new process over the prior art are seen in the fact that the implementation under the simplest conditions, e.g. B. when rubbing at ordinary temperature, it is possible that the reactant causing the water solubility also has a specific therapeutic effect and - finally. in that the new compounds have a certain lipoid solubility in addition to good water solubility. This lipoid solubility of a compound which is readily soluble in water is particularly advantageous from a therapeutic point of view. The new compounds are presumably salts. B. by its physical properties as a uniform compound (melting point 205 ", mixed melting point with campho-io-sulfonic acid iog °). Despite the simplicity of the process, it is a matter of defined reaction products and not just mechanical mixtures of the starting materials.

Beispiele i. 8-Oxychinolin und Campho-io-sulfonsäure werden in molarem Verhältnis gemischt, mit Wässer befeuchtet und das Umsetzungsprodukt zur Trockne eingedampft.Examples i. 8-oxyquinoline and campho-io-sulfonic acid are in molar Ratio mixed, with Water moisturizes and the reaction product evaporated to dryness.

Z. Gepulvertes 8-Oxychinolin und Campho-nsulfonsäure werden in molarem Verhältnis durch Verreiben in einer Reibschale oder Kugelmühle umgesetzt.Z. Powdered 8-oxyquinoline and campho-nsulfonic acid are in molar Ratio implemented by rubbing in a mortar or ball mill.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung leicht wasserlöslicher Verbindungen von 8-Oxychinolin, dadurch gekennzeichnet, daB 8-Oxychinolinbase mit Camphosulfonsäuren in etwa molarem Verhältnis umgesetzt wird.PATENT CLAIM: Process for the production of readily water-soluble compounds of 8-oxyquinoline, characterized in that 8-oxyquinoline base with camphosulfonic acids is implemented in an approximately molar ratio.
DE1938B0183346 1938-05-31 1938-05-31 Process for the preparation of readily water-soluble compounds of 8-oxyquinoline Expired DE698007C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1938B0183346 DE698007C (en) 1938-05-31 1938-05-31 Process for the preparation of readily water-soluble compounds of 8-oxyquinoline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1938B0183346 DE698007C (en) 1938-05-31 1938-05-31 Process for the preparation of readily water-soluble compounds of 8-oxyquinoline

Publications (1)

Publication Number Publication Date
DE698007C true DE698007C (en) 1940-10-30

Family

ID=7009537

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1938B0183346 Expired DE698007C (en) 1938-05-31 1938-05-31 Process for the preparation of readily water-soluble compounds of 8-oxyquinoline

Country Status (1)

Country Link
DE (1) DE698007C (en)

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