DE1017175B - Process for the production of new anesthetically acting aminocarboxamides - Google Patents

Process for the production of new anesthetically acting aminocarboxamides

Info

Publication number
DE1017175B
DE1017175B DEC12897A DEC0012897A DE1017175B DE 1017175 B DE1017175 B DE 1017175B DE C12897 A DEC12897 A DE C12897A DE C0012897 A DEC0012897 A DE C0012897A DE 1017175 B DE1017175 B DE 1017175B
Authority
DE
Germany
Prior art keywords
compound
parts
denotes
aminocarboxamides
propionylamino
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.)
Pending
Application number
DEC12897A
Other languages
German (de)
Inventor
Dr Werner Zerweck
Dr Otto Troesken
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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
Application filed by Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC12897A priority Critical patent/DE1017175B/en
Publication of DE1017175B publication Critical patent/DE1017175B/en
Pending 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

kl. 12 q 6/01 kl. 12 q 6/01

INTERNATIONALE Kt.INTERNATIONAL Kt.

C07c;dC07c; d

AUSLEGESCHRIFT 1017175EDITORIAL NOTES 1017175

C 12897IV b/12 q ANMELDETAG: 19. APRIL 1956C 12897IV b / 12 q REGISTRATION DATE: APRIL 19, 1956

BEKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
AUSLEGESCHRIFT: 10. OKTOBER 1957NOTICE
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL: OCTOBER 10, 1957

Das Patent 963 427 betrifft ein Verfahren zur Herstellung neuer anästhetisch wirkender Aminocarbonsäureamide, das dadurch gekennzeichnet ist, daß man mit einem basischen Acylrest substituierte polycyclische Verbindungen der allgemeinen FormelThe patent 963 427 relates to a process for the production of new anesthetic aminocarboxamides, which is characterized in that there are polycyclic compounds substituted with a basic acyl radical the general formula

R'-NH-CO-CH,-NR'-NH-CO-CH, -N

.R.R

worin R Alkylreste bedeuten, welche auch direkt oder mittels eines Heteroatoms miteinander verbunden sein können, und R' einen polycyclischen aromatischen Rest bedeuten, in dem eine o-Steilung zur Aminogruppe gleichzeitig Bestandteil eines anderen Ringes ist und die andere o-Stellung durch eine Alkylgruppe besetzt ist, nach folgendem Reaktionsschemawhere R denotes alkyl radicals which are also linked to one another directly or by means of a hetero atom can, and R 'denote a polycyclic aromatic radical in which an o-position to the amino group at the same time Is part of another ring and the other o-position is occupied by an alkyl group, according to following reaction scheme

R'-NH2+ Cl-CO-CH2-ClR'-NH 2 + Cl-CO-CH 2 -Cl

R'-NH-CO-CH2-Cl-I-HN:R'-NH-CO-CH 2 -Cl-I-HN:

Verfahren zur HerstellungMethod of manufacture

neuer anästhetisch wirkendernew anesthetic effect

AminocarbonsäureamideAminocarboxamides

Zusatz zum Patent 963 427Addendum to patent 963 427

Anmelder:Applicant:

Cassella FarbwerkeCassella inking units

Mainkur Aktiengesellschaft,Mainkur Aktiengesellschaft,

Frankfurt/M.-FechenheimFrankfurt / M.-Fechenheim

Dr. Werner Zerweck, Frankfurt/M.,Dr. Werner Zerweck, Frankfurt / M.,

und Dr. Otto Trösken, Frankfurt/M.-Fechenheim,and Dr. Otto Trösken, Frankfurt / M.-Fechenheim,

sind als Erfinder genannt wordenhave been named as inventors

R'-NH2+ Cl-CO-CH2-N;R'-NH 2 + Cl-CO-CH 2 -N;

worin die Reste R und R' die obige Bedeutung haben, herstellt.wherein the radicals R and R 'have the above meaning.

In Erweiterung dieses Erfindungsgedankens wurde nun gefunden, daß man anästhetisch wirkende Aminocarbonsäureamide von ebenfalls hervorragenden Eigenschaften erhält, wenn man mit einem basischen Acylrest substituierte polycyclische Verbindungen der allgemeinen FormelAs an extension of this inventive concept, it has now been found that anesthetically acting aminocarboxamides can be used also obtained excellent properties when substituted with a basic acyl radical polycyclic compounds of the general formula

R1-NH-CO-R2-NR 1 -NH-CO-R 2 -N

R1-NH2 +Cl-CO-R2-ClR 1 -NH 2 + Cl-CO-R 2 -Cl

.R.R

R1-NH-CO-Ra-Q+ HN.R 1 -NH-CO-Ra-Q + HN.

. R1-NH2+ Cl-CO-R2-N:. R 1 -NH 2 + Cl-CO-R 2 -N:

35 worin die Reste R1, R2 und R die obige Bedeutung haben, aufbaut.35 in which the radicals R 1 , R 2 and R have the above meaning, builds up.

Die Verbindungen kommen in Form ihrer mineralsauren Salze bzw. der quaternären Ammoniumsalze zur Anwendung. The compounds are used in the form of their mineral acid salts or the quaternary ammonium salts.

Beispiel 1 1 - (jS-Diäthylamino-propionylamino) -2-methyl-naphthalinExample 1 1 - (jS-Diethylamino-propionylamino) -2-methyl-naphthalene

worin R1 einen polycyclischen aromatischen Rest bedeutet, in dem eine o-Stellung zur Aminogruppe gleichzeitig Bestandteil eines anderen Ringes ist und die andere o-Stellung durch eine Alkylgruppe besetzt ist, R2 Alkylen mit einer Kette von mindestens 2 Kohlenstoffatomen und beide' R Alkyl bedeuten, wobei diese Alkylreste auch direkt oder mittels eines Heteroatoms miteinander verbunden sein und R2 und R weitere Substituenten enthalten können, nach folgendem Reaktionsschemawherein R 1 denotes a polycyclic aromatic radical in which one o-position to the amino group is also part of another ring and the other o-position is occupied by an alkyl group, R 2 alkylene with a chain of at least 2 carbon atoms and both 'R alkyl mean, where these alkyl radicals can also be connected to one another directly or by means of a hetero atom and R 2 and R can contain further substituents, according to the following reaction scheme

45 HN-CO-CH2-CH2-N45 HN-CO-CH 2 -CH 2 -N

-CH,-CH,

C2HC 2 H

2H5 2 H 5

124 Teile l-ß-Chlorpropionylamino-2-methyl-naphthalin, hergestellt aus l-Amino-2-methyl-naphthalin und124 parts of l-ß-chloropropionylamino-2-methyl-naphthalene, made from l-amino-2-methyl-naphthalene and

709 700/437709 700/437

/J-Chlorpropionylchlorid 'in Eisessig in Gegenwart von Natriumacetat (F. 161 bis 162° aus 80°/0igem Alkohol), werden mit 110 Teilen Diäthylamin in 500 Teilen Benzol 10 Stunden unter Rückfluß gekocht. Nach dem Erkalten saugt man vom ausgeschiedenen salzsauren Diäthylamin ab und dampft das Benzolfiltrat im Vakuum ein. Dabei wird das l-(jS-Diäthylamino-propionylamino)-2-methylnaphthalin in Form eines bräunlichen Öls erhalten, das auch nach längerem Stehen nicht erstarrt. Zur Herstellung des Hydrochlorids leitet man in eine benzolische Lösung der Base bis zur Sättigung Chlorwasserstoff ein. Das dadurch ausgeschiedene Produkt wird aus Dioxan umkristallisiert; F. 162 bis 163°./ J-chloropropionyl chloride 'in glacial acetic acid in the presence of sodium acetate (F. 161-162 ° 80 ° / 0 sodium alcohol) are boiled with 110 parts of diethylamine in 500 parts of benzene for 10 hours under reflux. After cooling, the precipitated hydrochloric acid diethylamine is filtered off with suction and the benzene filtrate is evaporated in vacuo. The l- (jS-diethylamino-propionylamino) -2-methylnaphthalene is obtained in the form of a brownish oil that does not solidify even after standing for a long time. To prepare the hydrochloride, hydrogen chloride is introduced into a benzene solution of the base until it is saturated. The product separated out is recrystallized from dioxane; 162 to 163 °.

Beispiel 2Example 2

l-(^-Piperidino-propionylamino)-2-methyl-naphthalinl - (^ - Piperidino-propionylamino) -2-methyl-naphthalene

, C H2 — CH2, , CH 2 - CH 2 ,

HN-CO-CH9-CH0-N:HN-CO-CH 9 -CH 0 -N:

CH,CH,

- GH«- GH «

C H9 —CH 9 -

HN-CO-CH2-CH2-N:HN-CO-CH 2 -CH 2 -N:

-CH,-CH,

,CHo, CHo

CHo— CH9 CHo - CH 9

262 Teile l-(,/3-Chlorpropion3'lamino)-2, 6-dimethylnaphthalin, hergestellt aus l-Amino-2, 6-dimethyl-naphthalin und /J-Chlorpropionylchlorid in Eisessig bei Gegenwart von Natriumacetat (F. 187 bis 188° aus Alkohol), werden mit 250 Teilen Piperidin in 1000 Teilen Benzol Stunden rückfließend gekocht. Dann wird, wie in vorstehendem Beispiel angegeben ist, aufgearbeitet. Das 1- (/3-Piperidino-propionylamino) -2, 6-dimethyl-naphtha-Kn bildet nach dem Umkristallisieren aus Benzin farblose Kristalle vom F. 104 bis 1053. Das salzsaure Salz, das man durch Umkristallisieren aus wäßrigem Dioxan in Form farbloser Kristalle erhält, zeigt den F. 194 bis 195°.262 parts of l - (, / 3-chloropropion3'lamino) -2, 6-dimethylnaphthalene, prepared from l-amino-2,6-dimethylnaphthalene and / J-chloropropionyl chloride in glacial acetic acid in the presence of sodium acetate (F. 187 to 188 ° from alcohol) are refluxed for hours with 250 parts of piperidine in 1000 parts of benzene. Then, as indicated in the previous example, worked up. The 1- (/ 3-piperidino-propionylamino) -2, 6-dimethyl-naphtha-Kn forms colorless crystals with a melting point of 104 to 105 3 after recrystallization from gasoline. The hydrochloric acid salt, which is obtained in the form of colorless crystals by recrystallization from aqueous dioxane, has a melting point of 194 ° to 195 °.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Abänderung des Verfahrens nach Patent 963 427 zur Herstellung neuer anästhetisch wirkender Aminocarbonsäureamide der allgemeinen FormelModification of the process according to patent 963 427 for the production of new anesthetic aminocarboxamides the general formula 248 Teile !-/S-Chlorpropionylamino^-methyl-naphtha-Hn und 250 Teile Piperidin werden in 1000 Teilen Benzol 10 Stunden unter Rückfluß gekocht. Nach dem Erkalten wird das ausgeschiedene salzsaure Piperidin durch Filtration entfernt und das Filtrat eingedampft. Das dabei als Rückstand erhaltene l-(/3-Piperidino-propionylamino)-2-methyl-naphthalin wird nach dem Umkristallisieren aus Benzin in Form farbloser Kristalle vom F. 109 bis 110° erhalten. Das in üblicher Weise dargestellte Hydrochlorid bildet nach dem Umkristallisieren aus wäßrigem Dioxan farblose Kristalle vom F. 226 bis 227°.248 parts! - / S-Chlorpropionylamino ^ -methyl-naphtha-Hn and 250 parts of piperidine are refluxed in 1000 parts of benzene for 10 hours. After cooling down the precipitated hydrochloric acid piperidine is removed by filtration and the filtrate is evaporated. That l - (/ 3-piperidino-propionylamino) -2-methyl-naphthalene obtained as a residue after recrystallization from gasoline in the form of colorless crystals of F. 109 up to 110 °. The hydrochloride, which is prepared in the usual way, forms after recrystallization aqueous dioxane colorless crystals with a melting point of 226 ° to 227 °. Beispiel 3Example 3 l-(jS-Piperidino-propionylamino)-2, 6-dimethylnaphthalin 1- (jS-piperidino-propionylamino) -2,6-dimethylnaphthalene XHo-CH,XHo-CH, 45 R1-NH-CO-R2-N: 45 R 1 -NH-CO-R 2 -N: worin R1 einen polycyclischen aromatischen Rest bedeutet, in dem eine o-Stellung zur Aminogruppe gleichzeitig Bestandteil eines anderen Ringes ist und die andere o-Stellung durch eine Alkylgruppe besetzt ist, R2 Alkylen mit einer Kette von mindestens 2 Kohlenstoffatomen und beide R Alkyl bedeuten, wobei diese Alkylreste auch direkt oder mittels eines Heteroatoms miteinander verbunden sein und R2 und R weitere Substituenten enthalten können, dadurch gekennzeichnet, daß man zunächst eine Verbindung R1 · N H2 mit einer Verbindung Cl · C O · R2 · Cl und dann mit einer Verbindungwhere R 1 denotes a polycyclic aromatic radical in which one o-position to the amino group is also part of another ring and the other o-position is occupied by an alkyl group, R 2 denotes alkylene with a chain of at least 2 carbon atoms and both R denotes alkyl , wherein these alkyl radicals can also be connected to one another directly or by means of a hetero atom and R 2 and R can contain further substituents, characterized in that first a compound R 1 · NH 2 with a compound Cl · CO · R 2 · Cl and then with a connection hn:hn: oder eine Verbindung R1 · N H2 mit einer Verbindungor a compound R 1 · NH 2 with a compound Cl-CO-R2-N;Cl-CO-R 2 -N; umsetzt, worin die Reste R1, R2 und R die obige Bedeutung haben.converts, in which the radicals R 1 , R 2 and R have the above meaning. Bei der Bekanntmachung der Anmeldung sind 2 Seiten Versuchsprotokoll ausgelegt worden.When the registration was announced, two pages of the test protocol were laid out. © 709 700/437 10.57© 709 700/437 10.57
DEC12897A 1956-04-19 1956-04-19 Process for the production of new anesthetically acting aminocarboxamides Pending DE1017175B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC12897A DE1017175B (en) 1956-04-19 1956-04-19 Process for the production of new anesthetically acting aminocarboxamides

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Application Number Priority Date Filing Date Title
DEC12897A DE1017175B (en) 1956-04-19 1956-04-19 Process for the production of new anesthetically acting aminocarboxamides

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7471695B2 (en) 2002-05-02 2008-12-30 Eads Astrium Gmbh Data interleaving method and user terminal

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7471695B2 (en) 2002-05-02 2008-12-30 Eads Astrium Gmbh Data interleaving method and user terminal

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