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DE2713794A1 - Tri:cyclic carboxamido-substd. benzyl alcohol and benzaldehyde derivs. - with hypoglycaemic and/or hypolipaemic activity - Google Patents

Tri:cyclic carboxamido-substd. benzyl alcohol and benzaldehyde derivs. - with hypoglycaemic and/or hypolipaemic activity

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Publication number
DE2713794A1
DE2713794A1 DE19772713794 DE2713794A DE2713794A1 DE 2713794 A1 DE2713794 A1 DE 2713794A1 DE 19772713794 DE19772713794 DE 19772713794 DE 2713794 A DE2713794 A DE 2713794A DE 2713794 A1 DE2713794 A1 DE 2713794A1
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Prior art keywords
aethyl
acetamido
fluorenyl
phenyl
deep
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DE19772713794
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German (de)
Inventor
Elmar Dr Rer Nat Bosies
Ruth Dr Rer Nat Heerdt
Manfred Dr Rer Nat Huebner
Hans Dr Rer Nat Kuehnle
Felix Helmut Prof Dr R Schmidt
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Roche Diagnostics GmbH
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Boehringer Mannheim GmbH
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Priority claimed from DE19762629752 external-priority patent/DE2629752A1/en
Application filed by Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Priority to DE19772713794 priority Critical patent/DE2713794A1/en
Publication of DE2713794A1 publication Critical patent/DE2713794A1/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
    • C07D335/12—Thioxanthenes
    • C07D335/20—Thioxanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Tricyclic carboxamide derivs. of formula (I) are new. (where A = direct bond, -CH2-, -CH2CH2-, -CH=CH-, -O-, -CH2-O-, -S- or -CH2-S-; V = opt. branched, opt. unsaturated trivalent 1-4 C hydrocarbon residue; R1, R2 = H, OH, alkyl, alkoxy, or halogen; R3 = H, OH or alkoxy; Y = opt. branched 1-3 C alkylene; X = direct bond, or opt. branched and opt. unsaturated 1-6 C alkylene; and D = hydroxymethyl or formyl). Specific cpds. (I) include 4- 2-(fluoren-9-ylacetamido)ethyl -benzyl alcohol. In an example, this is prepd. by reacting 4-(2-aminoethyl)-benzyl alcohol HCl with fluoren-9-ylacetyl chloride in the presence of NaOH.

Description

Gegenstand der Hauptanmeldung Aktenzeichen P 26 29 752.9 sind Carbonsäurederivate der allgemeinen Formel I The main application file number P 26 29 752.9 relates to carboxylic acid derivatives of the general formula I.

(I),(I),

in derin the

A einen Valenzstrich oder eine der Gruppen -CH[tief]2-, -CH[tief]2-CH[tief]2-, -CH-CH-, -O-, -CH[tief]2-O-, -S-, -CH[tief]2-S-,A is a valence line or one of the groups -CH [deep] 2-, -CH [deep] 2-CH [deep] 2-, -CH-CH-, -O-, -CH [deep] 2-O-, - S-, -CH [deep] 2-S-,

V einen geradkettigen oder verzweigten, gesättigten oder ungesättigten dreiwertigen Kohlenwasserstoff-Rest mit 1-4 Kohlenstoffatomen,V is a straight-chain or branched, saturated or unsaturated trivalent hydrocarbon radical with 1-4 carbon atoms,

R[tief]1 und R[tief[2 gleich oder verschieden sein können und Wasserstoff, Hydroxy, Alkyl-, Alkoxy-Reste oder Halogen,R [deep] 1 and R [deep [2 can be identical or different and are hydrogen, hydroxy, alkyl, alkoxy radicals or halogen,

R[tief]3 Wasserstoff, Hydroxy- oder eine Alkoxygruppe,R [deep] 3 hydrogen, hydroxyl or an alkoxy group,

Y eine gegebenenfalls verzweigte niedere Alkylengruppe mit 1-3 Kohlenstoffatomen,Y is an optionally branched lower alkylene group with 1-3 carbon atoms,

X einen Valenzstrich, eine geradkettige oder verzweigte, gesättigte oder ungesättigte Alkylenkette mit 1-6 Kohlenstoffatomen bedeuten, deren physiologisch unbedenkliche Salze, Ester und Amide, Verfahren zur Herstellung derselben, sowie ihre Verwendung zur Herstellung von Arzneimitteln mit hypoglykaemischer und/oder hypolipidaemischer Wirkung.X denotes a valence line, a straight-chain or branched, saturated or unsaturated alkylene chain with 1-6 carbon atoms, their physiologically harmless salts, esters and amides, processes for producing the same, and their use for producing medicaments with hypoglycemic and / or hypolipidaemic effects.

Diese Verbindungen der allgemeinen Formel I und ihre physiologisch unbedenklichen Salze, Ester und Amide besitzen eine überraschend ausgeprägte hypoglykaemische und/oder hypolipidaemische Wirksamkeit.These compounds of the general formula I and their physiologically acceptable salts, esters and amides have a surprisingly pronounced hypoglycemic and / or hypolipidaemic activity.

In Ausgestaltung des Erfindungsgedankens der Hauptanmeldung wurde nun gefunden, dass auch Verbindungen der allgemeinen Formel I, in denen die endständige Carboxylgruppe durch ihre Reduktionsstufen, die Carbaldehyd- und Hydroxymethyl-Gruppe, ersetzt ist, eine ausgeprägte hypoglykaemische und/oder hypolipidaemische Wirksamkeit aufweisen.In an embodiment of the inventive concept of the main application, it has now been found that compounds of the general formula I in which the terminal carboxyl group is replaced by its reduction stages, the carbaldehyde and hydroxymethyl group, have a pronounced hypoglycemic and / or hypolipidaemic activity.

Gegenstand der vorliegenden Zusatzanmeldung sind daher neue Derivate der tricyclischen N-substituierten Carbonsäureamide der allgemeinen Formel I' The present additional application therefore relates to new derivatives of the tricyclic N-substituted carboxamides of the general formula I '

(I')(I ')

in derin the

A einen Valenzstrich oder eine der Gruppen -CH[tief]2-, -CH[tief]2-CH[tief]2-, -CH-CH-, -O-, -CH[tief]2-O-, -S-, -CH[tief]2-S-,A is a valence line or one of the groups -CH [deep] 2-, -CH [deep] 2-CH [deep] 2-, -CH-CH-, -O-, -CH [deep] 2-O-, - S-, -CH [deep] 2-S-,

V einen geradkettigen oder verzweigten, gesättigten oder ungesättigten dreiwertigen Kohlenwasserstoff-Rest mit 1-4 Kohlenstoffatomen,V is a straight-chain or branched, saturated or unsaturated trivalent hydrocarbon radical with 1-4 carbon atoms,

R[tief]1 und R[tief[2 gleich oder verschieden sein können und Wasserstoff, Hydroxy, Alkyl-, Alkoxy-Reste oder Halogen,R [deep] 1 and R [deep [2 can be identical or different and are hydrogen, hydroxy, alkyl, alkoxy radicals or halogen,

R[tief]3 Wasserstoff, Hydroxy- oder eine Alkoxygruppe,R [deep] 3 hydrogen, hydroxyl or an alkoxy group,

Y eine gegebenenfalls verzweigte niedere Alkylengruppe mit 1-3 Kohlenstoffatomen,Y is an optionally branched lower alkylene group with 1-3 carbon atoms,

X einen Valenzstrich, eine geradkettige oder verzweigte, gesättigte oder ungesättigte Alkylenkette mit 1-6 Kohlenstoffatomen bedeuten undX denotes a valence line, a straight-chain or branched, saturated or unsaturated alkylene chain with 1-6 carbon atoms and

D eine Hydroxymethyl- oder eine Formylgruppe bedeuten.D represent a hydroxymethyl or a formyl group.

Unter "Alkyl-" und "Alkoxy-" sind in allen Fällen geradkettige oder verzweigte Reste mit 1-5 Kohlenstoffatomen zu verstehen. Vorzugsweise finden bei dem Alkylrest die Methylgruppe, bei dem Alkoxyrest die Methoxy- bis Butoxygruppe Verwendung."Alkyl" and "alkoxy" are to be understood in all cases as straight-chain or branched radicals with 1-5 carbon atoms. The methyl group is preferably used for the alkyl group and the methoxy to butoxy group for the alkoxy group.

Unter dreiwertigen Kohlenwasserstoff-Resten sind vorzugsweise die Gruppen zu verstehen.The groups are preferred among trivalent hydrocarbon radicals to understand.

Unter Halogen versteht man Fluor, Chlor und Brom.Halogen is understood to mean fluorine, chlorine and bromine.

Die Verbindungen der allgemeinen Formel I' können nach an sich bekannten Verfahren hergestellt werden, vorzugsweise indem man eine Carbonsäure der allgemeinen Formel I oder deren Säurederivate wie z.B. Ester, Säurehalogenide und Nitrile mit üblichen Reduktionsmitteln zu den entsprechenden Aldehyden bzw. Alkoholen der allgemeinen Formel I' reduziert. Desweiteren können die neuen Verbindungen der Formel I' analog Verfahren a) der Hauptanmeldung hergestellt werden, indem man statt der Amino-carbonsäure den entsprechenden Amino-aldehyd bzw. Aminoalkohol einsetzt.The compounds of general formula I 'can be prepared by processes known per se, preferably by adding a carboxylic acid of general formula I or its acid derivatives such as esters, acid halides and nitriles with customary reducing agents to give the corresponding aldehydes or alcohols of general formula I' reduced. Furthermore, the new compounds of the formula I 'can be prepared analogously to process a) of the main application by using the corresponding amino aldehyde or amino alcohol instead of the amino carboxylic acid.

Nachträgliche Umwandlungen bzw. Überführungen der Substituenten R[tief]1, R[tief]2 und R[tief]3 ineinander können, wie in der Hauptanmeldung beschrieben, durchgeführt werden.Subsequent conversions or conversions of the substituents R [deep] 1, R [deep] 2 and R [deep] 3 into one another can be carried out as described in the main application.

Zur Herstellung pharmazeutischer Zubereitungsformen wird ebenfalls auf die Hauptanmeldung verwiesen.For the production of pharmaceutical preparation forms, reference is also made to the main application.

Die erfindungsgemäßen neuen Verbindungen werden wie folgt hergestellt:The new compounds according to the invention are prepared as follows:

Beispiel 1example 1

4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-benzylalkohol4- [2- (fluorenyl- (9) -acetamido) -aethyl] -benzyl alcohol

Zu 1.9 g 4-(2-Aminoaethyl)-benzylalkohol-hydrochlorid (Fp. 151-155°C (Zers.)) in 10 ml 2 N Natronlauge tropft man bei 0°C eine Lösung von Fluorenyl-(9)-acetylchlorid (hergestellt aus 2.2 g Fluorenyl-(9)-essigsäure und 3 ml Thionylchlorid unter Rückfluss) in 12 ml Methylenchlorid, dann rührt man 2 Stunden bei Zimmertemperatur nach. Das Produkt ist in Wasser und Methylenchlorid schwer löslich und fällt aus. Durch Erwärmen wird das Methylenchlorid verdampft, die Festsubstanz abgesaugt, in Essigester aufgenommen, die Lösung nacheinander mit 1 N Salzsäure und 1 N Natronlauge gewaschen, getrocknet, mit Aktivkohle behandelt und eingeengt. Die rohe Substanz (Ausbeute 2.4 g = 69.5 % d. Th.; Fp. 168-171°C) wird zur Reinigung zweimal aus Aethylenchlorid und einmal aus wenig Essigester umkristallisiert.A solution of fluorenyl (9) acetyl chloride ( prepared from 2.2 g of fluorenyl (9) acetic acid and 3 ml of thionyl chloride under reflux) in 12 ml of methylene chloride, then stirred for 2 hours at room temperature. The product is sparingly soluble in water and methylene chloride and precipitates. The methylene chloride is evaporated by heating, the solid substance is filtered off with suction, taken up in ethyl acetate, the solution is washed successively with 1N hydrochloric acid and 1N sodium hydroxide solution, dried, treated with activated charcoal and concentrated. The crude substance (yield 2.4 g = 69.5% of theory; melting point 168-171 ° C.) is recrystallized twice from ethylene chloride and once from a little ethyl acetate for purification.

Ausbeute: 1.1 g (= 32 % d. Th.); Fp. 176-178°C.Yield: 1.1 g (= 32% of theory); Mp 176-178 ° C.

In analoger Weise erhält man:In an analogous way one obtains:

3-(4-[2-(Xanthen-9-carboxamido)-aethyl]-phenyl)-propanol-3- (4- [2- (xanthene-9-carboxamido) -aethyl] -phenyl) -propanol-

3-(4-[2-(5H-Dibenzo[a,d]cycloheptenyl-(5)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (5H-dibenzo [a, d] cycloheptenyl- (5) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(6,11-Dihydro-dibenz[b,e]oxepinyl-(11)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (6,11-dihydro-dibenz [b, e] oxepinyl- (11) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(3-Methyl-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (3-Methyl-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(Fluorenyliden-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (Fluorenylidene- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- [4- [2 (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(2-Methyl-6,11-dihydro-dibenz[b,e]oxepinyl-(11)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (2-methyl-6,11-dihydro-dibenz [b, e] oxepinyl- (11) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(9,10-Dihydroanthryl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (9,10-dihydroanthryl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(2-[Fluorenyl-(9)]-propionamido)-aethyl]-phenyl)-propanol,3- (4- [2- (2- [Fluorenyl- (9)] -propionamido) -aethyl] -phenyl) -propanol,

4-[2-(Xanthenyl-(9)-acetamido)-aethyl]-benzylalkohol,4- [2- (Xanthenyl- (9) -acetamido) -aethyl] -benzyl alcohol,

4-[2-(Fluoren-9-carboxamido)-aethyl]-benzylalkohol,4- [2- (fluoren-9-carboxamido) -aethyl] -benzyl alcohol,

4-[2-(6,11-Dihydro-dibenz[b,e]oxepinyl-(11)-acetamido)-aethyl]-benzylalkohol,4- [2- (6,11-dihydro-dibenz [b, e] oxepinyl- (11) -acetamido) -aethyl] -benzyl alcohol,

4-[2-(10,11-Dihydro-5H-dibenzo[a,d]cycloheptenyl-(5)-acetamido)-aethyl]-benzylalkohol,4- [2- (10,11-dihydro-5H-dibenzo [a, d] cycloheptenyl- (5) -acetamido) -aethyl] -benzyl alcohol,

4-[2-(2,6-Dimethyl-fluorenyl-(9)-acetamido)-aethyl]-benzylalkohol,4- [2- (2,6-dimethyl-fluorenyl- (9) -acetamido) -aethyl] -benzyl alcohol,

4-[2-(9,10-Dihydroanthryl-(9)-acetamido)-aethyl]-benzylalkohol,4- [2- (9,10-dihydroanthryl- (9) -acetamido) -aethyl] -benzyl alcohol,

2-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-aethanol,2- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -aethanol,

2-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-butanol,2- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -butanol,

3-[4-(Fluorenyl-(9)-acetamido-methyl)-phenyl]-propanol,3- [4- (Fluorenyl- (9) -acetamido-methyl) -phenyl] -propanol,

3-(4-[2-(Fluorenyl-(9)-acetamido)-propyl]-phenyl)-propanol,3- (4- [2- (Fluorenyl- (9) -acetamido) -propyl] -phenyl) -propanol,

3-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-allylalkohol,3- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -allyl alcohol,

3-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-2-methyl-allylalkohol,3- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -2-methyl-allyl alcohol,

2-Methoxy-4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-benzylalkohol,2-methoxy-4- [2- (fluorenyl- (9) -acetamido) -aethyl] -benzyl alcohol,

2-Methoxy-4-[2-(3-methoxy-fluorenyl-(9)-acetamido)-aethyl]-benzylalkohol,2-methoxy-4- [2- (3-methoxy-fluorenyl- (9) -acetamido) -aethyl] -benzyl alcohol,

5-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-pentanol,5- [4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -pentanol,

2-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,2- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

7-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-heptanol,7- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -heptanol,

4-(2-[3-(Fluorenyl-(9))-propionamido]-aethyl)-benzylalkohol,4- (2- [3- (Fluorenyl- (9)) -propionamido] -aethyl) -benzyl alcohol,

3-(4-[2-(Thioxanthenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- [4- [2- (Thioxanthenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

4-[2-(6,11-Dihydro-dibenzo[b,e]thiepinyliden-(11)-acetamido)-aethyl]-benzylalkohol,4- [2- (6,11-dihydro-dibenzo [b, e] thiepinylidene- (11) -acetamido) -aethyl] -benzyl alcohol,

4-(2-[3-(6,11-Dihydro-dibenz[b,e]oxepinyl-(11))-propionamido]-aethyl)-benzylalkohol,4- (2- [3- (6,11-dihydro-dibenz [b, e] oxepinyl- (11)) -propionamido] -aethyl) -benzyl alcohol,

3-(4-[2-(9,10-Dihydroanthracen-9-carboxamido)-aethyl]-phenyl-propanol,3- (4- [2- (9,10-dihydroanthracene-9-carboxamido) -aethyl] -phenyl-propanol,

3-(4-[2(Fluorenyl-(9)-carboxamido)-aethyl]-phenyl)-propanol,3- [4- [2 (Fluorenyl- (9) -carboxamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(3-Methoxy-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (3-methoxy-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-(2-[3-Fluorenyliden-(9))-propionamido]-aethyl)-phenyl)-propanol,3- (4- (2- [3-fluorenylidene- (9)) -propionamido] -aethyl) -phenyl) -propanol,

3-(4-[2-(6,11-Dihydro-dibenz[b,e]thienpinyl-(11)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (6,11-dihydro-dibenz [b, e] thienpinyl- (11) -acetamido) -aethyl] -phenyl) -propanol,

2-Methoxy-4-[2(1-methoxy-fluorenyl-(9)-acetamido)-aethyl]-benzyl-alkohol,2-methoxy-4- [2 (1-methoxy-fluorenyl- (9) -acetamido) -aethyl] -benzyl alcohol,

4-[2-(2-Methoxy-6,11-dihydro-dibenz[b,e]oxepinyliden-(11)-acetamido)-aethyl]-benzylalkohol,4- [2- (2-methoxy-6,11-dihydro-dibenz [b, e] oxepinylidene- (11) -acetamido) -aethyl] -benzyl alcohol,

4-[2-(6,11-Dihydro-dibenz[b,e]oxepinyliden-(11)-acetamido)-aethyl]-benzylalkohol,4- [2- (6,11-dihydro-dibenz [b, e] oxepinylidene- (11) -acetamido) -aethyl] -benzyl alcohol,

3-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-2-methyl-propanol,3- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -2-methyl-propanol,

3-(4-[2-(2-Chlor-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (2-chloro-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(2-[Fluorenyl-(9)]-butyramido)-aethyl]-phenyl)-propanol,3- (4- [2- (2- [Fluorenyl- (9)] - butyramido) -aethyl] -phenyl) -propanol,

3-(4-[2-(9-Methyl-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (9-Methyl-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(3-Chlor-6-methyl-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (4- [2- (3-chloro-6-methyl-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(2-[6,11-Dihydro-dibenz[b,e]oxepinyl-(11)]-propionamido)-aethyl]-phenyl)-propanol,3- (4- [2- (2- [6,11-dihydro-dibenz [b, e] oxepinyl- (11)] -propionamido) -aethyl] -phenyl) -propanol,

4-(2-(2-[Fluorenyl-(9)]-Propionamido)-aethyl)-benzylalkohol,4- (2- (2- [fluorenyl- (9)] -propionamido) -aethyl) -benzyl alcohol,

4-(2-(2-[Fluorenyl-(9)]-propionamido)-aethyl)-2-methoxy-benzlalkohol,4- (2- (2- [Fluorenyl- (9)] - propionamido) -aethyl) -2-methoxy-benzl alcohol,

3-(2-Butoxy-4-[2-(fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol,3- (2-butoxy-4- [2- (fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol,

3-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-butanol,3- [4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -butanol,

3-(4-[2-(3-Hydroxy-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propanol.3- [4- [2- (3-Hydroxy-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propanol.

Beispiel 2Example 2

4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-benzaldehyd4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -benzaldehyde

Aus 3.6 g Fluorenyl-(9)-essigsäure und 4 ml Thionylchlorid stellt man durch zweistündiges Erhitzen unter Rückfluss Fluorenyl-(9)-acetyl-chlorid dar, löst es in 20 ml Methylenchlorid und tropft diese Lösung bei 0°C zu 3,0 g 4-(2-Aminoaethyl)-benzaldehyd-hydrochlorid (Fp. ) 300°C) und 32 ml 1 N Natronlauge. Man lässt zunächst 1/2 Stunde unter Eiskühlung, dann 2 Stunden bei Zimmertemperatur nachrühren, trennt die beiden Schichten und schüttelt die wässrige Schicht nochmals mit Methylenchlorid aus. Die vereinigten organischen Schichten wäscht man nacheinander mit verdünnter Natronlauge und verdünnter Salzsäure, trocknet sie, verdampft das Methylenchlorid und reinigt das Produkt durch Chromatographie über eine Kieselgel-Säule mit Xylol:Aethylmethylketon = 1:1.Fluorenyl (9) acetyl chloride is prepared from 3.6 g of fluorenyl (9) acetic acid and 4 ml of thionyl chloride by heating under reflux for two hours, it is dissolved in 20 ml of methylene chloride and this solution is added dropwise at 0 ° C. to 3.0 g of 4- (2-aminoethyl) benzaldehyde hydrochloride (melting point 300 ° C.) and 32 ml of 1 N sodium hydroxide solution. The mixture is initially stirred for 1/2 hour with ice cooling, then for 2 hours at room temperature, the two layers are separated and the aqueous layer is extracted again with methylene chloride. The combined organic layers are washed successively with dilute sodium hydroxide solution and dilute hydrochloric acid, they are dried, the methylene chloride is evaporated and the product is purified by chromatography on a silica gel column with xylene: ethyl methyl ketone = 1: 1.

Ausbeute: 2.7 g (= 48 % d. Th.); Fp. 140-143°C.Yield: 2.7 g (= 48% of theory); Mp 140-143 ° C.

In analoger Weise erhält man:In an analogous way one obtains:

3-(4-[2-(Xanthen-9-carboxamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (xanthene-9-carboxamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(Dibenzo[a,d]cycloheptenyl-(5)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (Dibenzo [a, d] cycloheptenyl- (5) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(6,11-Dihydro-dibenz[b,e]oxepinyl-(11)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (6,11-dihydro-dibenz [b, e] oxepinyl- (11) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(3-Methyl-fluroenyl-(9)-acetamido-aethyl]-phenyl-propionaldehyd,3- (4- [2- (3-Methyl-fluroenyl- (9) -acetamido-ethyl] -phenyl-propionaldehyde,

3-(4-[2-(Fluorenyliden-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (fluorenylidene- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(2-Methyl-6,11-dihydro-dibenz[b,e]oxepinyl-(11)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (2-methyl-6,11-dihydro-dibenz [b, e] oxepinyl- (11) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(9,10-Dihydroanthryl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (9,10-dihydroanthryl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(2-[Fluorenyl-(9)]-propionamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (2- [Fluorenyl- (9)] -propionamido) -aethyl] -phenyl) -propionaldehyde,

4-[2-(Xanthenyl-(9)-acetamido)-aethyl]-benzaldehyd,4- [2- (Xanthenyl- (9) -acetamido) -aethyl] -benzaldehyde,

4-[2-(Fluoren-9-carboxamido)-aethyl]-benzaldehyd,4- [2- (fluoren-9-carboxamido) -aethyl] -benzaldehyde,

4-[2-(6,11-Dihydro-dibenz[b,e]oxepinyl-(11)-acetamido)-aethyl]-benzaldehyd,4- [2- (6,11-dihydro-dibenz [b, e] oxepinyl- (11) -acetamido) -aethyl] -benzaldehyde,

4-[2-(10,11-Dihydro-5H-dibenzo[a,d]cycloheptenyl-(5)-acetamido)-aethyl]-benzaldehyd,4- [2- (10,11-dihydro-5H-dibenzo [a, d] cycloheptenyl- (5) -acetamido) -aethyl] -benzaldehyde,

4-[2-(2,6-Dimethyl-fluorenyl-(9)-acetamido)-aethyl]-benzaldehyd,4- [2- (2,6-dimethyl-fluorenyl- (9) -acetamido) -aethyl] -benzaldehyde,

4-[2-(9,10-Dihydroanthryl-(9)-acetamido)-aethyl]-benzaldehyd,4- [2- (9,10-dihydroanthryl- (9) -acetamido) -aethyl] -benzaldehyde,

4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenylacetaldehyd,4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenylacetaldehyde,

2-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-butyraldehyd,2- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -butyraldehyde,

3-[4-(Fluorenyl-(9)-acetamido-methyl)-phenyl]-propionaldehyd,3- [4- (Fluorenyl- (9) -acetamido-methyl) -phenyl] -propionaldehyde,

3-(4-[2-(Fluorenyl-(9)-acetamido)-propyl]-phenyl)-propionaldehyd,3- (4- [2- (Fluorenyl- (9) -acetamido) -propyl] -phenyl) -propionaldehyde,

4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-zimtaldehyd,4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -cinnamaldehyde,

kleines Alpha-Methyl-4-[2-(fluorenyl-(9)-acetamido)-aethyl]-zimtaldehyd,small alpha-methyl-4- [2- (fluorenyl- (9) -acetamido) -aethyl] -cinnamaldehyde,

2-Methoxy-4-[2-(fluorenyl-(9)-acetamido)-aethyl]-benzaldehyd,2-methoxy-4- [2- (fluorenyl- (9) -acetamido) -aethyl] -benzaldehyde,

2-Methoxy-4-[2-(3-methoxy-fluorenyl-(9)-acetamido)-aethyl]-benzaldehyd,2-methoxy-4- [2- (3-methoxy-fluorenyl- (9) -acetamido) -aethyl] -benzaldehyde,

5-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-valeraldehyd,5- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -valeraldehyde,

2-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,2- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

7-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-heptanal,7- [4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -heptanal,

4-(2-[3-(Fluorenyl-(9)-propionamido]-aethyl)-benzaldehyd,4- (2- [3- (Fluorenyl- (9) -propionamido] -aethyl) -benzaldehyde,

3-(4-[2-(Thioxanthenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (Thioxanthenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

4-[2-(6,11-Dihydro-dibenzo[b,e]thiepinyliden-(11)acetamido)-aethyl]-benzaldehyd,4- [2- (6,11-dihydro-dibenzo [b, e] thiepinylidene- (11) acetamido) -aethyl] -benzaldehyde,

4-(2-[3-(6,11-dihydro-dibenz[b,e]oxepinyl-(11))-propionamido]-aethyl)-benzaldehyd,4- (2- [3- (6,11-dihydro-dibenz [b, e] oxepinyl- (11)) -propionamido] -aethyl) -benzaldehyde,

3-(4-[2-(9,10-Dihydroanthracen-9-carboxamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (9,10-dihydroanthracene-9-carboxamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(Fluorenyl-(9)-carboxamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (Fluorenyl- (9) -carboxamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(3-Methoxy-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (3-methoxy-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-(2-[3-(Fluorenyliden-(9))-propionamido]-aethyl)-phenyl)-propionaldehyd,3- (4- (2- [3- (fluorenylidene- (9)) -propionamido] -aethyl) -phenyl) -propionaldehyde,

3-(4-[2-(6,11-Dihydro-dibenz[b,e]-thiepinyl-(11)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (6,11-dihydro-dibenz [b, e] -thiepinyl- (11) -acetamido) -aethyl] -phenyl) -propionaldehyde,

2-Methoxy-4-[2-(1-methoxy-fluorenyl-(9)-acetamido)-aethyl]-benzaldehyd,2-methoxy-4- [2- (1-methoxy-fluorenyl- (9) -acetamido) -aethyl] -benzaldehyde,

4-[2-(2-Methoxy-6,11-dihydro-dibenz[b,e]oxepinyliden-(11)-acetamido)-aethyl]-benzaldehyd,4- [2- (2-methoxy-6,11-dihydro-dibenz [b, e] oxepinylidene- (11) -acetamido) -aethyl] -benzaldehyde,

4-[2-(6,11-Dihydro-dibenz[b,e]oxepinyliden-(11)-acetamido)-aethyl]-benzaldehyd,4- [2- (6,11-dihydro-dibenz [b, e] oxepinylidene- (11) -acetamido) -aethyl] -benzaldehyde,

3-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-2-methyl-propionaldehyd,3- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -2-methyl-propionaldehyde,

3-(4-[2-(2-Chlor-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (2-chloro-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(2-[Fluorenyl-(9)]-butyramido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (2- [Fluorenyl- (9)] - butyramido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(9-Methyl-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (9-Methyl-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(3-Chlor-6-methyl-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (3-chloro-6-methyl-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(2-[6,11-Dihydro-dibenz[b,e] oxepinyl-(11)]-propionamido)-aethyl]-phenyl)-propionaldehyd,3- (4- [2- (2- [6,11-dihydro-dibenz [b, e] oxepinyl- (11)] -propionamido) -aethyl] -phenyl) -propionaldehyde,

4-(2-(2-[Fluorenyl-(9)]-propionamido)-aethyl)-benzaldehyd,4- (2- (2- [fluorenyl- (9)] -propionamido) -aethyl) -benzaldehyde,

4-(2-(2-[Fluorenyl-(9)]-propionamido)-aethyl)-2-methoxy-benzaldehyd,4- (2- (2- [Fluorenyl- (9)] -propionamido) -aethyl) -2-methoxy-benzaldehyde,

3-(2-Butoxy-4-[2-(fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd,3- (2-Butoxy-4- [2- (fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde,

3-(4-[2-(Fluorenyl-(9)-acetamido)-aethyl]-phenyl)-butyraldehyd,3- (4- [2- (Fluorenyl- (9) -acetamido) -aethyl] -phenyl) -butyraldehyde,

3-(4-[2-(3-Hydroxy-fluorenyl-(9)-acetamido)-aethyl]-phenyl)-propionaldehyd3- [4- [2- (3-Hydroxy-fluorenyl- (9) -acetamido) -aethyl] -phenyl) -propionaldehyde

Claims (2)

1. Tricyclische N-substituierte Carbonsäureamide der allgemeinen Formel I 1. Tricyclic N-substituted carboxamides of the general formula I (I'),(I '), in derin the A einen Valenzstrich oder eine der Gruppen -CH[tief]2-, -CH[tief]2-CH[tief]2-, -CH-CH-, -O-, -CH[tief]2-O-, -S-, -CH[tief]2-S-,A is a valence line or one of the groups -CH [deep] 2-, -CH [deep] 2-CH [deep] 2-, -CH-CH-, -O-, -CH [deep] 2-O-, - S-, -CH [deep] 2-S-, V einen geradkettigen oder verzweigten, gesättigten oder ungesättigten dreiwertigen Kohlenwasserstoff-Rest mit 1-4 Kohlenstoffatomen,V is a straight-chain or branched, saturated or unsaturated trivalent hydrocarbon radical with 1-4 carbon atoms, R[tief]1 und R[tief[2 gleich oder verschieden sein können und Wasserstoff, Hydroxy, Alkyl-, Alkoxy-Reste oder Halogen,R [deep] 1 and R [deep [2 can be identical or different and are hydrogen, hydroxy, alkyl, alkoxy radicals or halogen, R[tief]3 Wasserstoff, Hydroxy- oder eine Alkoxygruppe,R [deep] 3 hydrogen, hydroxyl or an alkoxy group, Y eine gegebenenfalls verzweigte niedere Alkylengruppe mit 1-3 Kohlenstoffatomen,Y is an optionally branched lower alkylene group with 1-3 carbon atoms, X einen Valenzstrich, eine geradkettige oder verzweigte, gesättigte oder ungesättigte Alkylenkette mit 1-6 Kohlenstoffatomen bedeuten,X denotes a valence line, a straight-chain or branched, saturated or unsaturated alkylene chain with 1-6 carbon atoms, D eine Hydroxymethyl- oder eine Formylgruppe bedeuten.D represent a hydroxymethyl or a formyl group. 2. Arzneimittel, gekennzeichnet durch einen Gehalt an Verbindungen gemäß Anspruch 1 und übliche Trägerstoffe.2. Medicaments, characterized by a content of compounds according to claim 1 and customary carriers.
DE19772713794 1976-07-02 1977-03-29 Tri:cyclic carboxamido-substd. benzyl alcohol and benzaldehyde derivs. - with hypoglycaemic and/or hypolipaemic activity Ceased DE2713794A1 (en)

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