DE1955386A1 - Indanone and benzofuranone derivs, - antimicrobials - Google Patents

Indanone and benzofuranone derivs, - antimicrobials

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Publication number
DE1955386A1
DE1955386A1 DE19691955386 DE1955386A DE1955386A1 DE 1955386 A1 DE1955386 A1 DE 1955386A1 DE 19691955386 DE19691955386 DE 19691955386 DE 1955386 A DE1955386 A DE 1955386A DE 1955386 A1 DE1955386 A1 DE 1955386A1
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Germany
Prior art keywords
indanone
nitro
furfurylidene
acid addition
group
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Granted
Application number
DE19691955386
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German (de)
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DE1955386C3 (en
DE1955386B2 (en
Inventor
Rudolf Dr Albrecht
Hans-Joachim Dr Kessler
Eberhard Dr Schroeder
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Bayer Pharma AG
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Schering AG
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Priority claimed from DE19691955386 external-priority patent/DE1955386C3/en
Priority to DE19691955386 priority Critical patent/DE1955386C3/en
Priority to CH138570A priority patent/CH535225A/en
Priority to CS145470A priority patent/CS158268B2/cs
Priority to BR217447/70A priority patent/BR7017447D0/en
Priority to AT263570A priority patent/AT294813B/en
Priority to ES377795A priority patent/ES377795A1/en
Priority to NL7004483A priority patent/NL7004483A/xx
Priority to GB1470070A priority patent/GB1310951A/en
Priority to BE748110D priority patent/BE748110A/en
Priority to FR707011175A priority patent/FR2035988B1/fr
Priority to US23487A priority patent/US3671520A/en
Priority to JP45026440A priority patent/JPS4812740B1/ja
Publication of DE1955386A1 publication Critical patent/DE1955386A1/en
Publication of DE1955386B2 publication Critical patent/DE1955386B2/en
Publication of DE1955386C3 publication Critical patent/DE1955386C3/en
Application granted granted Critical
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/42—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2

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

Abstract

Indanone and benzofuranone derivs., antimicrobials Cmpds. of formula (I): (where X = O, S, NH; Y = O or CH2; R = benzoyloxy, NO2, alkoxycarbonyloxy, N-monoalkylaminocarbonyloxy, N, N-dialkylaminocarbonyloxy or N-substd. aminoalkoxy) and acid addition salts of aminoalkoxy/aminocarbonyloxy cmpds. are prepd. by reacting the corresp. NO2-aldehyde and corresp. indanone or benzofuranone, or by nitrating the 5-unsubstd. cmpd. (I) are useful as antimicrobials, esp. against Trichomonas vaginalis.

Description

NEUE ANTIMIKROBIELL WIRKSAME VERBINDUNGEN (Zusatz zur Patentameldung P 19 16 825.3) Im Hauptpatent .................... (Patentanmeldung P 19 werden Verbindungen der folgenden allgemeinen Formel beschrieben: worin X ein Sauerstoff- oder Schwefelatom oder eine NH-Gruppe, Y ein Sauerstoffatom oder eine CH2-Gruppe und R unter anderem eine Alkoxylalkoxygruppe bedeuten.NEW ANTIMICROBIALLY EFFECTIVE COMPOUNDS (addition to patent application P 19 16 825.3) In the main patent .................... (patent application P 19 compounds of the following general formula are described: where X is an oxygen or sulfur atom or an NH group, Y is an oxygen atom or a CH2 group and R is, inter alia, an alkoxylalkoxy group.

Diese Verbindungen zeigen sehr gute antimikrobielle Wirkungen, insbesondere gegen Trichomonas vaginalis. These compounds show very good antimicrobial effects, in particular against Trichomonas vaginalis.

In Weiterentwicklung der oben genannten Erfindung wurde nun gefunden, dass Verbindungen der allgemeinen Formel I mit R in der Bedeutung einer N-sul; stituierten Aminoalkoxygruppe ebenfalls sehr gute antmikrobielle Wirkungen, insbesondere gegen Trichomonas vaginalis, besitzen. In a further development of the above-mentioned invention, it has now been found that compounds of the general formula I where R has the meaning of an N-sul; established Aminoalkoxy group also has very good antmicrobial effects, especially against Trichomonas vaginalis.

Die Erfindung betrifft also Verbindungen der allgemeinen Formel des Hauptpatentes .......... (Patentanmeldung P 19 16 825.3), worin X und Y die in dem Hauptpatent genannte Bedeutung besitzen und R eine N-substituierte Äminoalkozygruppe bedeutet, und deren Säureadditionssalze organischer oder anorganischer Säuren. Als N-substituierte Aminoalkoxygruppen kommen vorzugsweise Mono- und Dialkylamino-, Pyrrolidino-, Pi peridino-, Piperazino-, N-Alkylpiperazino-, N-Acylpiperazino- und Morpholinoalkoxygruppen in Frage. Unter den Alkyl- und Acylresten sollen Gruppen mit 1-5 C-Atomen verstanden werden.The invention thus relates to compounds of the general formula of the main patent .......... (patent application P 19 16 825.3), wherein X and Y have the meaning given in the main patent and R is an N-substituted aminoalkozy group, and their acid addition salts of organic or inorganic acids. Preferred N-substituted aminoalkoxy groups are mono- and dialkylamino, pyrrolidino, piperidino, piperazino, N-alkylpiperazino, N-acylpiperazino and morpholinoalkoxy groups. The alkyl and acyl radicals are to be understood as meaning groups with 1-5 carbon atoms.

Die substituierten Aminoalkozyverbindungen kUnnen-auch als Säureadditionssalse vorliegen. Zur Salzbildung sind die physiologisch verträglichen Säuren geeignet. Geeignete Säuren sind zum Beispiel Chlorwasserstoffsäure, Schwefelsäure, Phosphorsäure, Essigsäure, Propionsäure, Bernsteinsäure, Zitronensäure, Benzoesäure, Salicylsäure und andere.The substituted aminoalkoxy compounds can also be used as acid addition salts are present. The physiologically compatible acids are suitable for salt formation. Suitable acids are, for example, hydrochloric acid, sulfuric acid, phosphoric acid, Acetic acid, propionic acid, succinic acid, citric acid, benzoic acid, salicylic acid and other.

Die neuen Verbindungen können in Analogie zu den im Hauptpatent angegebenen Verfahren hergestellt werden. So kann man a) einen Aldehyd der allgemeinen Formel worin X die oben genannte Bedeutung hat, oder ein funktionelles Derivat des Aldehydes mit einer Verbindung der allgemeinen Formel worin Y und R die oben angegebene Bedeutung besitzen, oder dessen Säureadditionssalz, umsetzen oder b) eine Verbindung der allgemeinen Formel worin x, Y und R die oben angegebene Bedeutung besitzen, oder dessen Säureadditionssalz, nitrieren, und gegebenenfalls die nach a) oder b) erhaltenen Verbindungen durch Behandeln mit Säure in die Säureadditionssalze überführen.The new compounds can be prepared in analogy to the processes specified in the main patent. So you can a) an aldehyde of the general formula wherein X has the abovementioned meaning, or a functional derivative of the aldehyde with a compound of the general formula in which Y and R have the meaning given above, or their acid addition salt, react or b) a compound of the general formula in which x, Y and R have the meaning given above, or the acid addition salt thereof, nitrating, and optionally converting the compounds obtained according to a) or b) into the acid addition salts by treatment with acid.

Das Verfahren gemäss a) wird bei Raumtemperatur oder erhöhter Temperatur in saurem Milieu vorzugsweise in Eisessig in Gegenwart von konzentierter Schwefelsäure oder in Orthophosphorsäure, durchgeführt. Als funktionelle Derivate der Aldehyde sind vorzugsweise die Diacetate zu nennen.The process according to a) is carried out at room temperature or elevated temperature in an acidic medium, preferably in glacial acetic acid in the presence of concentrated sulfuric acid or in orthophosphoric acid. As functional derivatives of aldehydes preferably the diacetates should be mentioned.

Die Nitrierung gemäss b) kann nach den bekannten Methoden, zum Beispiel mit Salpetersäure in Eersigsäure/Essigeäureaabydrid, erfolgen.The nitration according to b) can be carried out by known methods, for example with nitric acid in acetic acid / acetic acid aabydride.

Die neuen Verbindungen, insbesondere deren Säureadditionssalze, sind kristalline Verbindungen. er freien nasen lassen sich aus den Reaktionsgemischen durch Eingiessen in Eiswasser und gegebenenfalls Neutralisieren mit einer Base isolieren. Durch Behandeln mit Säuren können aus den freien Basen die entsprechenden Säureadditionssalze erhalten werden. Die Säureadditionssalze werden aus den Reaktionsgemischen durch Eindampfen unter rermin dertem Druck isoliert. Zur Reinigung werden insbesondere die Säureadditionssalze aus Alkoholen oder Alkohol/Wasser-Gemischen umkristallisiert.The new compounds, especially their acid addition salts, are crystalline compounds. he free noses from the reaction mixtures isolate by pouring into ice water and, if necessary, neutralizing with a base. By treating with acids, the corresponding acid addition salts can be obtained from the free bases can be obtained. The acid addition salts are made from the reaction mixtures Evaporation under reduced pressure isolated. For cleaning are in particular the acid addition salts are recrystallized from alcohols or alcohol / water mixtures.

Die neuen Verbindungen können in den pharmazeutisch üblichen Applikationsformen, wie Pillen, Dragees, Kapseln, Tabletten, Säften, Lösungen usw., verabfolgt werden.The new compounds can be administered in the usual pharmaceutical forms, such as pills, coated tablets, capsules, tablets, juices, solutions, etc., are administered.

Beispiel 1 2-(5-Nitro-2-furfryliden)-5-(2-dimethylaminoäthoxy)-1-indanonhydrochlorid 1,5 g 5-(2-Dimethylamonoäthoxy)-1-indanon-hydrochlorid und 1,92 g 5-Nitro-furfuraldiacetat werden in 20 ml Orthophosphorsäure 20 Stunden bei 500 C gerührt. Es s wird in Eiswasser gegossen, mit NaOH neutralisiert, mit Essigester ausgeschüttelt und die Essigesterlösung mit Wasser gewaschen, mit Na2SO4 getrocknet und eingedampft. Das es erhaltene 2-(5-Nitro-2-furfuryliden)-5-(2-dimethylaminoäthoxy)-1-indanon wird in Methanol aufgenommen, mit alkoholischer HVl versetzt und eingedampft. Der Rückstand wird aus Methanol umkristallisiert. Ausbeute 1,1 g (50% der Theorie). Schmelzpunkt 238°C (Zersetzung).Example 1 2- (5-Nitro-2-furfrylidene) -5- (2-dimethylaminoethoxy) -1-indanone hydrochloride 1.5 g of 5- (2-dimethylamonoethoxy) -1-indanone hydrochloride and 1.92 g of 5-nitro-furfural diacetate are stirred in 20 ml of orthophosphoric acid at 500 ° C. for 20 hours. It's going to be in ice water poured, neutralized with NaOH, extracted with ethyl acetate and the ethyl acetate solution washed with water, dried with Na2SO4 and evaporated. The 2- (5-nitro-2-furfurylidene) -5- (2-dimethylaminoethoxy) -1-indanone obtained is taken up in methanol, mixed with alcoholic HVl and evaporated. Of the The residue is recrystallized from methanol. Yield 1.1 g (50% of theory). Melting point 238 ° C (decomposition).

C18H19ClN2O5 Ber. Cl 9,36 N 7,39 (378,8) Gef. Cl 9,41 N 7,42 Beispiel 2 2-(5-Nitro-2-furfuryliden)-5-(2-diäthylaminoäthoxy)-1-indanonsulfat 600 mg 5-(2-Diäthylaminoäthoxy)-1-indanon-hydrochlorid und 300 mg 5-Nitrofurfural werden in lo ml Essigsäure in Gegenwart von 0,112 ml konzentrierter H2SO4 16 Stunden bei 100°C gerührt.C18H19ClN2O5 calc. Cl 9.36 N 7.39 (378.8) Found Cl 9.41 N 7.42 Example 2 2- (5-Nitro-2-furfurylidene) -5- (2-diethylaminoethoxy) -1-indanone sulfate 600 mg 5- (2-diethylaminoethoxy) -1-indanone hydrochloride and 300 mg of 5-nitrofurfural are dissolved in lo ml of acetic acid in the presence of 0.112 ml concentrated H2SO4 for 16 hours at 100 ° C.

Es wird im Vakuum eingedampft und der Rückstand aus Äthanol/ Wasser 3:1 umkristallisiert. Ausbeute 300 mg (31 % der Theorie).It is evaporated in vacuo and the residue from ethanol / water 3: 1 recrystallized. Yield 300 mg (31% of theory).

Schmelzpunkt 248°C.Melting point 248 ° C.

C29H22N2O5.H2So4 Ber. N 5,98 S 6,84 (468,5) Gef. N 5,87 s 6,73 Beispiel 3 2-(5-Nitro-2-furfuryliden)-5-(2-pyrrolidinoäthoxy)-1-indanonsulfat.C29H22N2O5.H2So4 Ber. N 5.98 S 6.84 (468.5) Found N 5.87 s 6.73 example 3 2- (5-nitro-2-furfurylidene) -5- (2-pyrrolidinoethoxy) -1-indanone sulfate.

Die Herstellung erfolgt analog Beispiel 2 aus 245 mg 5-(2-Pyrrolidonoäthoxy)-1-indanon und 141 mg 5-Nitrofurfural.Production takes place analogously to Example 2 from 245 mg of 5- (2-pyrrolidonoethoxy) -1-indanone and 141 mg of 5-nitrofurfural.

Umkristallisation aus Methanol. Ausbeute 2oo mg (+3 Vb der Theorie). Schmelzpunkt 2340 C.Recrystallization from methanol. Yield 2oo mg (+3 Vb of theory). Melting point 2340 C.

C20H20N2O5#H2SO4 Ber. N 6,01 S 6,87 Gef. N 5,79 S 6,76 (466,5) Beispiel 4 2-(5-Nitro-2-furfuryliden)-5-(2-piperidino-äthoxy)-1-indanonsulfat Die Herstellung erfolgt analog Beispiel 2 aus 450 mg 5-(2-Piperidinoäthoxy)-1-indanon-hydrochlorid und 250 mg 5-Nitrofurfural. Umkristallisation aus Äthanol. Ausbeute 200 mg (27 % der Theorie). Schmelzpunkt 1650 C C21H22N2O5#H2SO4 Ber. N 5,83 S 6,67 (480,5) Gef. N 5,63 5 6,3o Beispiel 5 2-(5-Nitro-2-furfuryliden)-5-(2-morpholinoäthoxy)-1-indanon sulfat Die Herstellung erfolgt analog Beispiel 2 aus 600 mg 5-(2-Morpholinoäthoxy)-1-indanon-hydrochlorid und 280 mg 5-Nitrofurfural. Umkristallisation aus Methanol/Wasser 1:1, Ausbeute 400 mg (41 % der Theorie). Schmelzpunkt 262° C (Zersetzung).C20H20N2O5 # H2SO4 calc. N 6.01 S 6.87 Found N 5.79 S 6.76 (466.5) Example 4 2- (5-Nitro-2-furfurylidene) -5- (2-piperidino-ethoxy) -1-indanone sulfate The preparation takes place analogously to Example 2 from 450 mg of 5- (2-piperidinoethoxy) -1-indanone hydrochloride and 250 mg of 5-nitrofurfural. Recrystallization from ethanol. Yield 200 mg (27% the theory). Melting point 1650 C C21H22N2O5 # H2SO4 calc. N 5.83 S 6.67 (480.5) found. N 5.63-5 6.3o Example 5 2- (5-Nitro-2-furfurylidene) -5- (2-morpholinoethoxy) -1-indanone sulfate The preparation takes place analogously to Example 2 from 600 mg of 5- (2-morpholinoethoxy) -1-indanone hydrochloride and 280 mg of 5-nitrofurfural. Recrystallization from methanol / water 1: 1, yield 400 mg (41% of theory). Melting point 262 ° C (decomposition).

C20H20N2O6#H2SO4 Ber. N 5,81 S 6,64 (482,4) Gef. N 5,58 S 6,43 Beispiel 6 2-(5-Nitro-2-furfuryliden)-5-(2-n-butylamino-äthoxy)-l-indanon-sulfat 0,7 g 5-(2-n-Butylamino-äthoxy)-1-indanon-hydrochlorid und o,35 g 5-Nitrofurfural werden in 10 ml;.Essigsäure in Gegenwart von o,13 ml konzentrierter H2SO4 6 Stunden bei 100° C gerührt, danach vollständig eingeengt. Das erhaltene Cl wird mehrfach mit Äther behandelt und im Vakuum von allen flüchtigen Substanzen befreit. C20H20N2O6 # H2SO4 calc. N 5.81 S 6.64 (482.4) Found N 5.58 S 6.43 Example 6 2- (5-nitro-2-furfurylidene) -5- (2-n-butylamino-ethoxy) -l-indanone sulfate 0.7 g 5- (2-n-butylamino-ethoxy) -1-indanone- hydrochloride and o, 35 g of 5-nitrofurfural are in 10 ml;. acetic acid in the presence of o, 13 ml concentrated H2SO4 for 6 hours at 100 ° C, then concentrated completely. The Cl obtained is treated several times with ether and all volatile in vacuo Free substances.

C20H24N2O9S Ber. N 5,98 S 6,85 (468,5) Gef. N 5,73 S 6,56 Beispiel 7 2-(5-Nitro-2-pyrrolylmethylen)-6-(2-dimethylamino-äthoxy)-3-benzofuranon-hydrochlorid Die Herstellung erfolgt analog Beispiel 1 aus 2,57 g 6-(2-Dimethylaminoäthoxy)-3-benzofuranon-hydrochlorid und 2,43 g 5-Nitrofurfuraldiacetat. Umkristallisation aus Methanol. Ausbeute 1,85 g (48 % der Theorie). Schmelzpunkt über 300°C.C20H24N2O9S calc. N 5.98 S 6.85 (468.5) Found. N 5.73 S 6.56 Example 7 2- (5-Nitro-2-pyrrolylmethylene) -6- (2-dimethylamino-ethoxy) -3-benzofuranone hydrochloride Production takes place analogously to Example 1 from 2.57 g of 6- (2-dimethylaminoethoxy) -3-benzofuranone hydrochloride and 2.43 g of 5-nitrofurfural diacetate. Recrystallization from methanol. Yield 1.85 g (48% of theory). Melting point over 300 ° C.

C17H18ClN3O5 Ber. Cl 9,35 N 11,08 (379,8) Gef. Cl 9,54 N 10,84C17H18ClN3O5 calc. Cl 9.35 N 11.08 (379.8) found Cl 9.54 N 10.84

Claims (11)

P a t e n t a n 1. Verbindungen der allgemeinen Formel gemäss Hauptpatent ........ (Patentanmeldung P 19 16 825.3), worin X ein Sauerstoff- oder Schwefelatom oder eine NH-Gruppe, Y ein Sauerstoffatom oder eine CH2-Gruppe und R eine N-substituierte Aminoalkoxygruppe bedeuten, und deren Säureadditionssalze organischer oder anorganischer Säuren.P atentane 1. Compounds of the general formula according to the main patent ........ (patent application P 19 16 825.3), in which X is an oxygen or sulfur atom or an NH group, Y is an oxygen atom or a CH2 group and R is an N-substituted aminoalkoxy group, and their Acid addition salts of organic or inorganic acids. 2. 2-(5-Nitro-2-furfuryliden)-5-(2-dimethylaminoäthoxy)-1-indanon.2. 2- (5-Nitro-2-furfurylidene) -5- (2-dimethylaminoethoxy) -1-indanone. 3. 2-(5-Nitro-2-furfuryliden)-5-(2-dimethylaminoäthoxy)-1-indanon-hydro chlorid.3. 2- (5-Nitro-2-furfurylidene) -5- (2-dimethylaminoethoxy) -1-indanone-hydro chloride. 4. 2-(5-Nitro-2-furfuryliden)-5-(2-dimäthylaminoäthoxy)-1-indanon-sulfat.4. 2- (5-Nitro-2-furfurylidene) -5- (2-dimethylaminoethoxy) -1-indanone sulfate. 5. 2-(5-Nitro-2-furfuryliden)-5-(2-pyrrolidinoäthoxy)-1 indanon-sulfat.5. 2- (5-Nitro-2-furfurylidene) -5- (2-pyrrolidinoethoxy) -1 indanone sulfate. 6. 2-(5-Nitro-2-furfuryliden)-5-(2-piperidino-äthoxy)-1 indanon-sulfat.6. 2- (5-Nitro-2-furfurylidene) -5- (2-piperidino-ethoxy) -1 indanone sulfate. 7. 2-(5-Nitro-2-furfuryliden)-5-(2-morpholinoäthoxy)-1-indanon-sulfat.7. 2- (5-Nitro-2-furfurylidene) -5- (2-morpholinoethoxy) -1-indanone sulfate. 8. 2-( 5-Nitro-2-forfuryliden) -5-( 2-n-butylamino-äthoxy) -1-indanon-sulfat.8. 2- (5-Nitro-2-forfurylidene) -5- (2-n-butylamino-ethoxy) -1-indanone sulfate. 9. 2-(5-Nitro-2-pyrrolylmethylen)-6-(2-dimethylamino-äthoxy)-3-benzofuranon-hydrochlorid. 9. 2- (5-Nitro-2-pyrrolylmethylene) -6- (2-dimethylamino-ethoxy) -3-benzofuranone hydrochloride. 10. Arzneimittel, gekennzeichnet durch einen Gehalt an einer oder mehreren Verbindungen gemäss Anspruch 1.10. Medicines, characterized by a content of one or several compounds according to claim 1. 11. Verfahren zur Herstellung von Verbindungen der allgemeinen Formel gemäss Hauptpatent ..........(Patentanmeldung P P 19 16 825.3), worin X ein Sauerstoff- oder Schwefelatom oder eine WH-Gruppe, Y ein Sauerstoffatom oder eine CH2-Gruppe und R eine N-substituierte Aminoalkoxygruppe bedeuten, und deren Säureadditionssalze organischer oder anorganischer Säuren, dadurch gekennzeichnet, dass man a) einen Aldehyd der allgemeinen Formel worin X die oben genannte Bedeutung hat, oder ein funktionelles Derivat des Aldehydes mit einer Verbindung der allgemeinen Formel worin Y und R die oben angegebene Bedeutung besitzen, oder dessen Säureadditionssalz, umsetzt oder b) eine Verbindung der allgemeinen Formel worin X, Y und R die oben angegebene Bedeutung besitzen, oder dessen Säureadditionssalz, nitriert und gegebenenfalls die nach a) oder b) erhaltenen Verbindungen durch Behandeln mit Säure in die Säureadditionssale üb erführt.11. Process for the preparation of compounds of the general formula according to the main patent .......... (patent application PP 19 16 825.3), in which X is an oxygen or sulfur atom or a WH group, Y is an oxygen atom or a CH2 group and R is an N-substituted aminoalkoxy group, and their acid addition salts of organic or inorganic acids, characterized in that a) an aldehyde of the general formula wherein X has the abovementioned meaning, or a functional derivative of the aldehyde with a compound of the general formula in which Y and R are as defined above, or their acid addition salt is reacted, or b) a compound of the general formula in which X, Y and R have the meaning given above, or its acid addition salt, nitrated and, if appropriate, the compounds obtained according to a) or b) are converted into the acid addition salts by treatment with acid.
DE19691955386 1969-03-29 1969-10-29 2- (5'-Nitro-2'-furfurylidene) indanones and processes for their preparation, and pharmaceuticals containing these compounds Expired DE1955386C3 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DE19691955386 DE1955386C3 (en) 1969-10-29 2- (5'-Nitro-2'-furfurylidene) indanones and processes for their preparation, and pharmaceuticals containing these compounds
CH138570A CH535225A (en) 1969-03-29 1970-01-30 Process for the preparation of heterocyclic nitro compounds
CS145470A CS158268B2 (en) 1969-03-29 1970-03-04
BR217447/70A BR7017447D0 (en) 1969-03-29 1970-03-13 PROCESS FOR THE PREPARATION OF NEW ANTIMICROBIAL COMPOUNDS
AT263570A AT294813B (en) 1969-03-29 1970-03-20 Process for the preparation of new heterocyclic compounds and their salts
ES377795A ES377795A1 (en) 1969-03-29 1970-03-21 Antimicrobial indanones
NL7004483A NL7004483A (en) 1969-03-29 1970-03-26
GB1470070A GB1310951A (en) 1969-03-29 1970-03-26 Antimicrobially active nitro-furan-thiophene and -pyrrole deri vatives
BE748110D BE748110A (en) 1969-03-29 1970-03-27 COMPOUNDS WITH ANTIMICROBIAL ACTION, THEIR PREPARATION AND USE
FR707011175A FR2035988B1 (en) 1969-03-29 1970-03-27
US23487A US3671520A (en) 1969-03-29 1970-03-27 Antimicrobial indanones
JP45026440A JPS4812740B1 (en) 1969-03-29 1970-03-28

Applications Claiming Priority (1)

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DE19691955386 DE1955386C3 (en) 1969-10-29 2- (5'-Nitro-2'-furfurylidene) indanones and processes for their preparation, and pharmaceuticals containing these compounds

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DE1955386A1 true DE1955386A1 (en) 1971-05-13
DE1955386B2 DE1955386B2 (en) 1977-01-20
DE1955386C3 DE1955386C3 (en) 1977-09-08

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Legal Events

Date Code Title Description
C3 Grant after two publication steps (3rd publication)
E77 Valid patent as to the heymanns-index 1977
8339 Ceased/non-payment of the annual fee