DE1955386C3 - 2- (5'-Nitro-2'-furfurylidene) indanones and processes for their preparation, and pharmaceuticals containing these compounds - Google Patents
2- (5'-Nitro-2'-furfurylidene) indanones and processes for their preparation, and pharmaceuticals containing these compoundsInfo
- Publication number
- DE1955386C3 DE1955386C3 DE19691955386 DE1955386A DE1955386C3 DE 1955386 C3 DE1955386 C3 DE 1955386C3 DE 19691955386 DE19691955386 DE 19691955386 DE 1955386 A DE1955386 A DE 1955386A DE 1955386 C3 DE1955386 C3 DE 1955386C3
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- furfurylidene
- indanone
- compounds
- preparation
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims description 17
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000003814 drug Substances 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000011780 sodium chloride Substances 0.000 claims description 11
- -1 pyrrolidino, piperidino Chemical group 0.000 claims description 10
- NDSTUUPEXNCUNW-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanol Chemical compound OCC1=CC=C([N+]([O-])=O)O1 NDSTUUPEXNCUNW-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 229960000583 Acetic Acid Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 3
- 244000052616 bacterial pathogens Species 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 241000224527 Trichomonas vaginalis Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000845 anti-microbial Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical compound [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical class [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
- 206010060945 Bacterial infection Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WXEPAQXYMRRCSL-UHFFFAOYSA-N Cl.N1(CCCCC1)CCOC=1C=C2CCC(C2=CC1)=O Chemical compound Cl.N1(CCCCC1)CCOC=1C=C2CCC(C2=CC1)=O WXEPAQXYMRRCSL-UHFFFAOYSA-N 0.000 description 1
- VYNSLCZZQAUSQM-UHFFFAOYSA-N Cl.O1CCN(CC1)CCOC=1C=C2CCC(C2=CC1)=O Chemical compound Cl.O1CCN(CC1)CCOC=1C=C2CCC(C2=CC1)=O VYNSLCZZQAUSQM-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000108056 Monas Species 0.000 description 1
- CUBOQLNNPSGSHP-UHFFFAOYSA-N N1(CCCC1)CCOC=1C=C2CCC(C2=CC1)=O Chemical compound N1(CCCC1)CCOC=1C=C2CCC(C2=CC1)=O CUBOQLNNPSGSHP-UHFFFAOYSA-N 0.000 description 1
- 244000110797 Polygonum persicaria Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 229940055033 Proteus mirabilis Drugs 0.000 description 1
- 229940055023 Pseudomonas aeruginosa Drugs 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 240000005481 Salvia hispanica Species 0.000 description 1
- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- 241001635318 Trichococcus Species 0.000 description 1
- 208000005448 Trichomonas Infections Diseases 0.000 description 1
- HSXKWKJCZNRMJO-UHFFFAOYSA-N [acetyloxy-(5-nitrofuran-2-yl)methyl] acetate Chemical compound CC(=O)OC(OC(C)=O)C1=CC=C([N+]([O-])=O)O1 HSXKWKJCZNRMJO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000012377 chia Nutrition 0.000 description 1
- 235000014167 chia Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002485 urinary Effects 0.000 description 1
Description
H2CH 2 C
in der R die im Anspruch 1 angegebene Bedeutung besitzt oder einem entsprechenden Säureadditionssalz desselben umsetzt und anschließend, gegebenenfalls die erhaltene Verbindung in ein pharmakologisch verträgliches Säureadditionssalz überführt.in which R has the meaning given in claim 1 or a corresponding acid addition salt converts the same and then, optionally, the compound obtained in a pharmacological Compatible acid addition salt transferred.
4. Arzneimittel, gekennzeichnet durch einen Gehalt an einer Verbindung gemäß Anspruch 1 neben üblichen, inerten Trägerstoffen oder Verdünnungsmitteln. 4. Medicament, characterized by a content of a compound according to claim 1 in addition to customary, inert carriers or diluents.
Die Erfindung betrifft 2-(5'-Nitro-2'-furfuryliden)-indanone der allgemeinen FormelThe invention relates to 2- (5'-nitro-2'-furfurylidene) indanones of the general formula
O2N-CjL-CHO 2 N-CjL-CH
3535
4040
45 dadurch hergestellt, daß man in an sich bekannter Weise 5-Nitrofurfurol oder ein funktionelles Derivat desselben mit einer Verbindung der.allgemeinen Formel 45 prepared by reacting in a manner known per se 5-nitrofurfurol or a functional derivative thereof with a compound of the general formula
in der R eine N-Alkyl- oder Ν,Ν-Dialkylaminoäthoxygruppe
mit 1 bis 5 Kohlenstoffatomen im Alkylteil oder eine Pyrrolidino-, Piperidino- oder Morpholinoäthoxygruppe
bedeutet und deren pharmakologisch verträgliche Säureadditionssalze, ein Verfahren zu deren
Herstellung sowie diese Verbindungen enthaltende Arzneimittel.
Die Verbindungen der obigen Formel werdenin which R denotes an N-alkyl or Ν, Ν-dialkylaminoethoxy group with 1 to 5 carbon atoms in the alkyl part or a pyrrolidino, piperidino or morpholinoethoxy group and their pharmacologically acceptable acid addition salts, a process for their preparation and drugs containing these compounds.
The compounds of the above formula are
5555
60 H3C 60 H 3 C
in der R die oben angegebene Bedeutung besitzt oder einem entsprechenden Säureadditionssalz desselben umsetzt und anschließend gegebenenfalls die erhaltene Verbindung in ein pharmakologisch verträgliches Säureadditionssalz überführt.in which R has the meaning given above or a corresponding acid addition salt thereof converts and then optionally the compound obtained into a pharmacologically acceptable Acid addition salt transferred.
Das Verfahren wird bei Raumtemperatur oder erhöhter Temperatur in saurem Milieu, vorzugsweise in Eisessig in Gegenwart von konzentrierter Schwefelsäure oder in Orthophosphorsäure durchgeführt. Als funktionelles Derivat des 5-Nitrofurfurols wird vorzugsweise das Diacetat verwendet.The process is carried out at room temperature or at an elevated temperature in an acidic medium, preferably in Glacial acetic acid carried out in the presence of concentrated sulfuric acid or in orthophosphoric acid. When Functional derivative of 5-nitrofurfural, the diacetate is preferably used.
Die erfindungsgemäßen Verbindungen, insbesondere deren Säureadditionssalze, sind kristalline Verbindungen. Die freien Basen 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 vermindertem Druck isoliert Zur Reinigung werden insbesondere die Säureadditionssalze aus Alkoholen oder Alkohol/Wasser-Gemischen umkristallisiertThe compounds according to the invention, in particular their acid addition salts, are crystalline compounds. The free bases can be removed from the reaction mixtures by pouring them into ice water and optionally Isolate neutralize with a base. By treating with acids, the corresponding acid addition salts are obtained. The acid addition salts are made from the reaction mixtures isolated by evaporation under reduced pressure Acid addition salts recrystallized from alcohols or alcohol / water mixtures
Zur Salzbildung eignen sich physiologisch verträgliche Säuren, zum Beispiel Chlorwasserstoffsäure, Schwefelsäure, Phosphorsäure, Essigsäure, Propionsäure, Bernsteinsäure, Zitronensäure, Benzoesäure, Salicylsäure. Physiologically compatible acids are suitable for salt formation, for example hydrochloric acid, sulfuric acid, Phosphoric acid, acetic acid, propionic acid, succinic acid, citric acid, benzoic acid, salicylic acid.
Die erfindungsgemäßen Verbindungen besitzen eine breite antimikrobielle Wirkung, wie z. B. gegen grampositive und gramnegative Keime und Protozoen, wie Trichomonas vaginalis. Zum Nachweis ihrer Wirkung wurden sie in Vergleichsversuchen gegen bekannte Verbindungen aus der südafrikanischen Patentschrift 68 05 902 geprüft. Dabei wurden die Mindest-Hemmkonzentrationen (MIC) nach der bekannten Reihenverdünnungstechnik in flüssigen Medien bestimmt, die ausführlich in dem folgenden Buch beschrieben ist: »Analytical Microbiology, F. Kavanagh, Edit, Academic Press, New York& London 1963«. Aus der nachstehenden Tabelle geht hervor, daß die erfindungs;-gemäßen VerbindungenThe compounds of the invention have a broad antimicrobial effect, such as. B. against gram positive and gram-negative germs and protozoa such as Trichomonas vaginalis. To prove their effectiveness they were in comparison tests against known compounds from the South African patent 68 05 902 checked. The minimum inhibitory concentrations (MIC) were determined using the known serial dilution technique determined in liquid media, which is described in detail in the following book: "Analytical Microbiology, F. Kavanagh, Edit, Academic Press, New York & London 1963". From the The table below shows that the compounds according to the invention
2-(5'-Nitro-2'-furfuryliden)-5-(2-dimethylaminoäthoxy)-1 -indanon-hydrochlc'rid und 2-(5'-Nitro-2'-furfuryliden)-5-(2-pyrrolidinoäthoxy)-1 -indanon-sulfat2- (5'-nitro-2'-furfurylidene) -5- (2-dimethylaminoethoxy) -1 indanone hydrochloride and 2- (5'-nitro-2'-furfurylidene) -5- (2-pyrrolidinoethoxy) -1 indanone sulfate
im Hinblick auf ihre antimikrobielle Wirkung dem Stand der Technik überlegen sind.are superior to the prior art with regard to their antimicrobial effect.
Neben einer deutlich besseren Aktivität gegen Trichomonas vaginalis zeichnen sich die erfindungsgemäßen Verbindungen vor allem durch ihre Wirksamkeit gegen Problemkeime wie Proteus mirabilis bzw. Pseudomonas aeruginosa aus. die durch die Vergleichssubstanzen entweder gar nicht oder nur mäßig gehemmt werden. Die erfindungsgemäßen Verbindungen eignen sich durch ihre, zum Teil auch gegen andere Keime (S. aureus, E. coli, P. vulgaris und Kl. pneumoniae)In addition to a significantly better activity against Trichomonas vaginalis, those according to the invention are notable Compounds mainly due to their effectiveness against problem germs such as Proteus mirabilis or Pseudomonas aeruginosa. those caused by the comparison substances either not at all or only moderately be inhibited. The compounds according to the invention are suitable because of their properties, and in some cases also against others Germs (S. aureus, E. coli, P. vulgaris and Kl. Pneumoniae)
überlegene Wirkung besonders als Arzneistoffe zur Behandlung von solchen Trichomonadeninfektionen, die durch bakterielle Infektionen aus den Harngängen begleitet sind.superior effect especially as medicinal substances for the treatment of such trichomonas infections, which are accompanied by bacterial infections from the urinary ducts.
MIC (r/ml)MIC (r / ml)
2-{.5'-Nitro-2'-furfuryliden)-5-(2-di- 0,12 - {. 5'-nitro-2'-furfurylidene) -5- (2-di-0.1
methylaminoäthoxy)-l-indanon,
Hydrochlorid (Beispiel 1)methylaminoethoxy) -l-indanone,
Hydrochloride (example 1)
2-(5'-Nitro-2'-furfuryliden)-5-(2-pyrro- 0,1
lidinoäthoxy)-l-indanon, Sulfat
(Beispiel 3)"2- (5'-nitro-2'-furfurylidene) -5- (2-pyrro-0.1
lidinoethoxy) -l-indanone, sulfate
(Example 3) "
Vergleichssubstanzen entsprechend
ZA-PS 68 05902Comparison substances accordingly
ZA-PS 68 05902
2-(5-Nitro-2-furfuryl!den)-5-methoxy- 0,2
1-indanon2- (5-nitro-2-furfuryldene) -5-methoxy-0.2
1-indanon
2-(5-Nitro-2-furfuryliden)-4-methyl- 0,1
l-indanon2- (5-nitro-2-furfurylidene) -4-methyl-0.1
l-indanon
2-(5-Nitro-2-furfuryliden)-5-hydroxy- 0,01
1-indanon2- (5-nitro-2-furfurylidene) -5-hydroxy-0.01
1-indanon
0,02 0,40.02 0.4
0,2 3,10.2 3.1
1,6
1,61.6
1.6
3,1 6,2 0,000753.1 6.2 0.00075
6,2 12,56.2 12.5
0,0490.049
Die erfindungsgemäßen Verbindungen können in den pharmazeutisch üblichen Applikationsformen, wie Pillen, Dragoes, Kapseln, Tabletten, Säften, Lösungen usw., verabfolgt werden.The compounds according to the invention can be used in the pharmaceutically customary application forms, such as pills, Dragoes, capsules, tablets, juices, solutions, etc., can be administered.
2-(5'-Nitro-2'-furfuryIiden}5-(2-dimethylaminoäthoxy)-1 -indanonhydrochlorid2- (5'-nitro-2'-furfurylidene} 5- (2-dimethylaminoethoxy) -1 indanone hydrochloride
300 mg (31% der Theorie) 2-(5'-Nitro-2'-furfuryliden)-5-(2-diäthylaminoäthoxy)-l-indanon-sulfat vom F. 248° C erhalten.300 mg (31% of theory) 2- (5'-nitro-2'-furfurylidene) -5- (2-diethylaminoethoxy) -1-indanone sulfate obtained from the m.p. 248 ° C.
Gewichtsanalyse in 0/OfUrC20H22N2O5 · H2SO4
(MG 468,5):Weight analysis in 0 / OfUrC 20 H 22 N 2 O 5 · H 2 SO 4
(MG 468.5):
Berechnet: N 5,98, S 6,84;Calculated: N 5.98, S 6.84;
gefunden: N 5,87, S 6,73.found: N 5.87, S 6.73.
3535
1,5 g 5-)2-Dimethylaminoäthoxy)-l-indanon-hydrochlorid
und 1,92 g 5-Nitro-furfuroldiacetat werden in 20 ml Orthophosphorsäure 20 Stunden bei 50°C
gerührt. Die Mischung wird dann in Eiswasser gegossen,
mit NaOH neutralisiert, mit Essigester ausgeschüttelt und die Eisessigesterlösung mit Wasser gewaschen,
hierauf mit Na2SO4 getrocknet und eingedampft. Das als
Rückstand anfallende 2-(5'-Nitro-2'-furfuryliden)-5-(2-dhnethylaminoäthoxy)-1-indanon
wird in Methanol aufgenommen, mit alkoholischer HCl versetzt und eingedampft. Der Rückstand wird aus Methanol
umkristallisiert Man erhält 1,1 g (50% der Theorie) 2-(5'-Nitro-2'-furfuryliden)-5-(2-dimethylaminoäthoxy)-1
-indanon-hydrochlorid vom F. 238° C (Zersetzung).
Gewichtsanalyse in % für Ci8Hi9ClN2O5
(MG 378,8):1.5 g of 5-) 2-dimethylaminoethoxy) -l-indanone hydrochloride and 1.92 g of 5-nitro-furfural diacetate are stirred in 20 ml of orthophosphoric acid at 50 ° C. for 20 hours. The mixture is then poured into ice water, neutralized with NaOH, extracted with ethyl acetate and the glacial acetic ester solution washed with water, then dried with Na 2 SO 4 and evaporated. The 2- (5'-nitro-2'-furfurylidene) -5- (2-dimethylaminoethoxy) -1-indanone obtained as a residue is taken up in methanol, mixed with alcoholic HCl and evaporated. The residue is recrystallized from methanol. 1.1 g (50% of theory) of 2- (5'-nitro-2'-furfurylidene) -5- (2-dimethylaminoethoxy) -1-indanone hydrochloride with a melting point of 238 ° are obtained C (decomposition).
Weight analysis in% for Ci 8 Hi 9 ClN 2 O 5
(MG 378.8):
Berechnet: Cl 936, N 7,39; gefunden: Cl 9,41, N 7,42.Calculated: Cl 936, N 7.39; found: Cl 9.41, N 7.42.
2-(5'-Nitro-2'-furfuryliden)-5-(2-diäthylaiminoäthoxy)-1 -indanonsulfat2- (5'-nitro-2'-furfurylidene) -5- (2-diethylaiminoethoxy) -1 -indanone sulfate
600 mg 5-(2-Diäthylaminoäthoxy)-l-indanom-hydrochicrid und 300 mg 5-Nitrofuro! werden in 10 m! Essigsäure in Gegenwart von 0,112 ml konzentrierter H2SO4 6 Stunden bei 100° C gerührt. Dann wird die Mischung im Vakuum eingedampft und der Rückstand aus Äthanol/Wasser (3:1) umkristallisiert. Es werden B e i s ρ i e.1 3600 mg 5- (2-diethylaminoethoxy) -l-indanom-hydrochicrid and 300 mg 5-nitrofuro! will be in 10 m! Acetic acid in the presence of 0.112 ml of concentrated H 2 SO 4 was stirred at 100 ° C. for 6 hours. The mixture is then evaporated in vacuo and the residue is recrystallized from ethanol / water (3: 1). There are B is ρ i e.1 3
2-(5'-Nitro-2'-furfuryliden)-5-(2-pyrrolidinoäthoxy)-1 -indanonsulfat2- (5'-nitro-2'-furfurylidene) -5- (2-pyrrolidinoethoxy) -1 -indanone sulfate
Die Herstellung erfolgt analog Beispiel 2 aus 245 mg 5-(2-Pyrrolidinoäthoxy)-1-indanon und 141 mg 5-Nitrofmrfurol. Durch Umkristallisation der nach dem Eindampfen anfallenden Rückstände aus Methanol werden 200 mg (43% Theorie) 2-(5'-Nitro-2'-fuifuryliden)-5-(2-pyrrolidinoäthoxy)-l-indanon-sulfat vom F. 234° C erhalten. The preparation takes place analogously to Example 2 from 245 mg of 5- (2-pyrrolidinoethoxy) -1-indanone and 141 mg of 5-nitrofuran. The residues obtained after evaporation are recrystallized from methanol 200 mg (43% theory) 2- (5'-nitro-2'-fuifurylidene) -5- (2-pyrrolidinoethoxy) -1-indanone sulfate obtained from the mp 234 ° C.
Gewichtsanalyse in % für C2OH2ON2Os · H2SO4
(MG 466,5):Weight analysis in% for C 2 OH 2 ON 2 Os · H 2 SO 4
(MG 466.5):
Berechnet: N 6,01, S 6,87;Calculated: N 6.01, S 6.87;
gefunden: N 5,79, S 6,76.found: N 5.79, S 6.76.
2-(5'-Nitro-2'-furfuryliden)-5-(2-piperidinoäthoxy)-1 -indanonsulfat2- (5'-nitro-2'-furfurylidene) -5- (2-piperidinoethoxy) -1 -indanone sulfate
Die Herstellung erfolgt analog Beispiel 2 aus 450 mg 5-(2- Piperidinoäthoxy)-1 -indanon-hydrochlorid und
250 mg 5-Nitrofurfurol. Nach der Umkristallisation des Rückstandes aus Äthanol erhält man 200 mg (27% der
Theorie) des 2-(5'-Nitro-2'-furfuryliden)-5-(2-piperidinoäthoxy)-!-indanon-su!fats
vom F. 165° C.
Gewichtsanalyse in % WrC2IH22N2O5 · H2SO4
(MG 480,5):Production takes place analogously to Example 2 from 450 mg of 5- (2-piperidinoethoxy) -1-indanone hydrochloride and 250 mg of 5-nitrofurfurol. After recrystallization of the residue from ethanol, 200 mg (27% of theory) of 2- (5'-nitro-2'-furfurylidene) -5- (2-piperidinoethoxy) -! - indanon-su! Fats from F. 165 ° C.
Weight analysis in% WrC 2 IH 22 N 2 O 5 · H 2 SO 4
(MG 480.5):
Berechnet: N 5,83, S 6,67;Calculated: N 5.83, S 6.67;
gefunden: N 5,63, S 6,30found: N 5.63, S 6.30
2-(5'-Nit!O-2'-furfuryliden)-5-(2-morpholinoäthoxy)-l-indanon sulfat2- (5'-Nit! O-2'-furfurylidene) -5- (2-morpholinoethoxy) -1-indanone sulfate
Die Herstellung erfolgt an.Uog Beispiel 2 aus 600 mg 5-(2-Morpholinoäthoxy)-l -indanon-hydrochlorid und 280 mg 5-Nitrofurfurol. Durch Umkristallisation des Rückstandes aus Methanol/Wasser (1 :\) erhält man 400 mg (41% der Theorie) 2-(5'-Nitro-2'-furfuryliden)-5-(2-morpholinoäthoxy)-l-indanon-sulfat vom F. 262 C (Zersetzung).The preparation takes place according to Example 2 from 600 mg of 5- (2-morpholinoethoxy) -1-indanone hydrochloride and 280 mg of 5-nitrofurfurol. Recrystallization of the residue from methanol / water (1 : \) gives 400 mg (41% of theory) of 2- (5'-nitro-2'-furfurylidene) -5- (2-morpholinoethoxy) -l-indanone sulfate from F. 262 C (decomposition).
Gewichtsanalyse in % für C20H20N2O6 · H2SO4
(MG 482.4):Weight analysis in% for C 20 H 20 N 2 O 6 · H 2 SO 4
(MG 482.4):
1515th
Berechnet: N 5,81, S 6,64;
gefunden: N 5,58, S 6,43.Calculated: N 5.81, S 6.64;
found: N 5.58, S 6.43.
Beispie! 6Example! 6th
2-(5'-Nitro-2'-furfuryliden)-5-(2-n-butylaminoäthoxy)-1 -indanonsulf at2- (5'-nitro-2'-furfurylidene) -5- (2-n-butylaminoethoxy) -1 -indanonsulf at
0,7 g 5-(2-n-Butylamino-äthoxy-l-indanon-hydrochlorid und 0,35 g 5-Nitrofurfurol werden in 10 ml Essigsäure in Gegenwart von 0,13 ml kenzentrierter H2SO4 6 Stunden bei 1000C gerührt. Danach wird die Mischung vollständig eingeengt. Das erhaltene öl wird mehrfach mit Äther behandelt und im Vakuum von allen flüchtigen Substanzen befreit. Man erhält 550 mg 2-(5'-Nitro-2'-furfuryliden)-5-(2-n-butylamino-äthoxy)-1-indanon-sulfat. 0.7 g of 5- (2-n-butylamino-ethoxy-l-indanone hydrochloride and 0.35 g of 5-Nitrofurfurol are stirred for 6 hours at 100 0 C in 10 ml of acetic acid in the presence of 0.13 ml kenzentrierter H2SO4. The mixture is then completely concentrated, the oil obtained is treated several times with ether and freed from all volatile substances in vacuo, giving 550 mg of 2- (5'-nitro-2'-furfurylidene) -5- (2-n-butylamino) ethoxy) -1-indanone sulfate.
Gewichtsanalyse in °/o für C20H24N2O9S
(MC- 468,5):Weight analysis in ° / o for C20H24N2O9S
(MC- 468.5):
Berechnet: N 5,98, S 6,85;Calculated: N 5.98, S 6.85;
gefunden: N 5,73, S 6,54.found: N 5.73, S 6.54.
Claims (3)
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 |
| FR707011175A FR2035988B1 (en) | 1969-03-29 | 1970-03-27 | |
| BE748110D BE748110A (en) | 1969-03-29 | 1970-03-27 | COMPOUNDS WITH ANTIMICROBIAL ACTION, THEIR PREPARATION AND USE |
| US23487A US3671520A (en) | 1969-03-29 | 1970-03-27 | Antimicrobial indanones |
| JP45026440A JPS4812740B1 (en) | 1969-03-29 | 1970-03-28 |
Applications Claiming Priority (1)
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1955386A1 DE1955386A1 (en) | 1971-05-13 |
| DE1955386B2 DE1955386B2 (en) | 1977-01-20 |
| DE1955386C3 true DE1955386C3 (en) | 1977-09-08 |
Family
ID=
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