DE512406C - Process for the presentation of pharmaceutically valuable products - Google Patents

Process for the presentation of pharmaceutically valuable products

Info

Publication number
DE512406C
DE512406C DEI37248D DEI0037248D DE512406C DE 512406 C DE512406 C DE 512406C DE I37248 D DEI37248 D DE I37248D DE I0037248 D DEI0037248 D DE I0037248D DE 512406 C DE512406 C DE 512406C
Authority
DE
Germany
Prior art keywords
presentation
valuable products
pharmaceutically valuable
boiling point
pressure
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
DEI37248D
Other languages
German (de)
Inventor
Dr Fritz Schoenhoefer
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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
Priority to DEI28507D priority Critical patent/DE499826C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI37248D priority patent/DE512406C/en
Application granted granted Critical
Publication of DE512406C publication Critical patent/DE512406C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Description

Verfahren zur Darstellung pharmazeutisch wertvoller Produkte Durch das Hauptpatent 499 826 ist ein Verfahren zur Herstellung N-substituierter aromatischer Aminooxv- und Diaminoverbindungen geschützt. EsJ besteht darin, daß man Aminooxyverbindungen oder Diamine der aromatischen Reihe, ihre Abkömmlinge oder Kernsubstitutionsprodukte nach den hierfür üblichen Methoden in solche stärker basische Polyaminoderivate überführt, welche die neueingeführten Stickstoffatome mit Hilfe aliphatischer Reste an den aromatischen Aminogruppen gebunden enthalten.Process for the preparation of pharmaceutically valuable products The main patent 499 826 protects a process for the preparation of N-substituted aromatic aminooxv and diamino compounds. It consists in converting aminooxy compounds or diamines of the aromatic series, their derivatives or core substitution products, by the methods customary for this purpose, into more basic polyamino derivatives which contain the newly introduced nitrogen atoms bound to the aromatic amino groups by means of aliphatic radicals.

Es wurde nun gefunden, daß auch solche Verbindungen dieselben oder ähnliche wertvolle pharmakologische Eigenschaften besitzen, welche hydroaromatische oder heterocyclische Reste an den aromatischen Aminogruppen gebunden enthalten.It has now been found that such compounds are the same or have similar valuable pharmacological properties, which hydroaromatic or contain heterocyclic radicals bonded to the aromatic amino groups.

Die Herstellung geschieht in der im Hauptpatent beschriebenen Weise. Beispiel r Die Verbindung läßt sich durch Umsetzung von i-Isopropyloxy-2-methoxy-4-aminobenzol mit a.-Piperidyl-ß-oxy-y-chlorpropan erhalten. Hellgelbes öl vom Siedepunkt 225 bis 23o° unter 5 mm Druck, das in der Kälte erstarrt (Schmelzpunkt g2 bis 9q.°). Beispiele wird auf analoge Weise :erhalten mit i-Dimethylamino-2-chlorcyclohexän: Die Base ist ein farbloses Öl vom Siedepunkt 173 bis 175° unter z mm Druck.The production takes place in the manner described in the main patent. Example r The compound can be obtained by reacting i-isopropyloxy-2-methoxy-4-aminobenzene with α-piperidyl-β-oxy-y-chloropropane. Light yellow oil with a boiling point of 225 to 230 ° under 5 mm pressure, which solidifies in the cold (melting point g2 to 9q. °). Examples is in an analogous manner: obtained with i-dimethylamino-2-chlorocyclohexane: The base is a colorless oil with a boiling point of 173 ° to 175 ° under z mm pressure.

Beispiel3 Die Verbindung der Formel wird durch Einwirkung von Pyrrolidyläthylchlorid (farblose Flüssigkeit vom KP- .40 bis 41°) auf i-Isopropyloxy-2-methoxy-4-aminobenzol erhalten. Die neue Base destilliert unter a mm Druck als helles f51 vom Siedepunkt 168 bis 17o° und gibt mit Salzsäure ein in Wasser leicht lösliches, weißes Hydrochlorid.Example 3 The compound of the formula is obtained by the action of pyrrolidyl ethyl chloride (colorless liquid from KP- .40 to 41 °) on i-isopropyloxy-2-methoxy-4-aminobenzene. The new base distills under a mm of pressure as a pale f51 with a boiling point of 168 to 170 ° and, with hydrochloric acid, gives a white hydrochloride that is readily soluble in water.

Beispiel4 Die Verbindung der Formel wird in analoger Weise aus 1,2-Diinethoxy-4-aminobenzol und dem Hydrochlorid des N-Methyl-3-chlormethyl- (A- 3 -) -tetrahydroppridins (dargestellt durch Reduktion des N-Methyl- 0 -3-) -tetrahydropyridin-3-aldehyds (vgl.. Wohl, Ber. 40 [19071, Seite 4712) mit Natriumamalgan und Chlorierung des so erhaltenen Alkohols mit Thionylchlorid) erhalten. Das neue Kondensationsprodukt destilliert unter 2 mm Druck als helles Öl mit dem Siedepunkt 167 bis 168°. Die Base bildet ein in Wasser leicht lösliches, weißes Hydrochlorid. Beispiel Das durch Einwirkung von Piperidyläthylchlorid auf m-Nitranilin erhaltene Hydrochlorid des Kondensationsproduktes wird mit Eisen und Essigsäure reduziert. Die neue Verbindung zeigt den Siedepunkt 158 bis 16o° bei z mm. Druck und bildet mit ätherischer Salzsäure ein in Wasser leicht lösliches, weißes Hydrochlorid.Example 4 The compound of the formula is made in an analogous manner from 1,2-diinethoxy-4-aminobenzene and the hydrochloride of N-methyl-3-chloromethyl- (A- 3 -) -tetrahydroppridine (produced by reduction of N-methyl-0-3-) tetrahydropyridine -3-aldehyde (cf. Wohl, Ber. 40 [19071, page 4712) with sodium amalgan and chlorination of the alcohol thus obtained with thionyl chloride). The new condensation product distills under 2 mm pressure as a pale oil with a boiling point of 167 to 168 °. The base forms a white hydrochloride which is easily soluble in water. example The hydrochloride of the condensation product obtained by the action of piperidylethyl chloride on m-nitroaniline is reduced with iron and acetic acid. The new compound has a boiling point of 158 to 16o ° at z mm. Pressure and, with ethereal hydrochloric acid, forms a white hydrochloride that is easily soluble in water.

Claims (1)

PATENTANSPRUCH: Weitere Ausbildung des durch Patent 499 826 geschützten Verfahrens zur Darstellung von N-substituierten Aminooxy-und Diaminoverbindungen der aromatischen Reihe sowie ihrer Abkömmlinge und Kernsubstitutionsprodukte, darin bestehend, daß hier die aromatischenAminogruppen durch basische Reste der hydroaromatischen oder heterocyclischen Reihe substituiert werden.PATENT CLAIM: Further development of the process protected by patent 499 826 for the preparation of N-substituted aminooxy and diamino compounds of the aromatic series and their derivatives and core substitution products, consisting in that the aromatic amino groups are substituted by basic radicals of the hydroaromatic or heterocyclic series.
DEI37248D 1926-07-09 1927-06-18 Process for the presentation of pharmaceutically valuable products Expired DE512406C (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEI28507D DE499826C (en) 1926-07-09 1926-07-09 Process for the preparation of N-dialkylaminoalkyl derivatives of aromatic aminooxy and diamino compounds
DEI37248D DE512406C (en) 1926-07-09 1927-06-18 Process for the presentation of pharmaceutically valuable products

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEI28507D DE499826C (en) 1926-07-09 1926-07-09 Process for the preparation of N-dialkylaminoalkyl derivatives of aromatic aminooxy and diamino compounds
DEI37248D DE512406C (en) 1926-07-09 1927-06-18 Process for the presentation of pharmaceutically valuable products

Publications (1)

Publication Number Publication Date
DE512406C true DE512406C (en) 1930-11-11

Family

ID=33099010

Family Applications (2)

Application Number Title Priority Date Filing Date
DEI28507D Expired DE499826C (en) 1926-07-09 1926-07-09 Process for the preparation of N-dialkylaminoalkyl derivatives of aromatic aminooxy and diamino compounds
DEI37248D Expired DE512406C (en) 1926-07-09 1927-06-18 Process for the presentation of pharmaceutically valuable products

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DEI28507D Expired DE499826C (en) 1926-07-09 1926-07-09 Process for the preparation of N-dialkylaminoalkyl derivatives of aromatic aminooxy and diamino compounds

Country Status (1)

Country Link
DE (2) DE499826C (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3002997A (en) * 1958-01-29 1961-10-03 Polaroid Corp Photographic products, processes and compositions

Also Published As

Publication number Publication date
DE499826C (en) 1930-06-23

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