DE1054091B - Process for the preparation of N-substituted 2-phenyl-7-aminoalkoxy-chromones - Google Patents

Process for the preparation of N-substituted 2-phenyl-7-aminoalkoxy-chromones

Info

Publication number
DE1054091B
DE1054091B DEC16925A DEC0016925A DE1054091B DE 1054091 B DE1054091 B DE 1054091B DE C16925 A DEC16925 A DE C16925A DE C0016925 A DEC0016925 A DE C0016925A DE 1054091 B DE1054091 B DE 1054091B
Authority
DE
Germany
Prior art keywords
phenyl
substituted
chromones
aminoalkoxy
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.)
Pending
Application number
DEC16925A
Other languages
German (de)
Inventor
Dr Erwin Kohlstaedt
Dr Karl-Heinz Klingler
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.)
CHEMIEWERK HOMBURG AG
Original Assignee
CHEMIEWERK HOMBURG 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 CHEMIEWERK HOMBURG AG filed Critical CHEMIEWERK HOMBURG AG
Priority to DEC16925A priority Critical patent/DE1054091B/en
Publication of DE1054091B publication Critical patent/DE1054091B/en
Priority to CH7340459A priority patent/CH378339A/en
Priority to NL239670A priority patent/NL103682C/xx
Priority to BE579151A priority patent/BE579151A/en
Priority to FR795451A priority patent/FR478M/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

Verfahren zur Herstellung von N-substituierten 2-Phenyl-7-aminoalkoxy-chromonen In der deutschen Patentschrift 1018 874 wird die Herstellung von N-substituierten 2-Methyl-7-aminoalkoxychromonen.beschrieben. Man erhält diese Produkte durch Umsetzung der Alkalisalze von 2-Methyl-7-oxychromon mit basisch substituierten Alkylhalogeniden in einem organischen Lösungsmittel. Pharmakologisch zeichnen sich diese Verbindungen durch khellinähnliche Eigenschaften aus, wobei als Vorteile gegenüber Khellin die größere therapeutische Breite und die gute Wasserlöslichkeit anzusehen sind.Process for the preparation of N-substituted 2-phenyl-7-aminoalkoxy-chromones In the German patent specification 1018 874 the preparation of N-substituted 2-methyl-7-aminoalkoxychromones is described. These products are obtained by reacting the alkali metal salts of 2-methyl-7-oxychromone with basic substituted alkyl halides in an organic solvent. Pharmacologically, these compounds are characterized by properties similar to khellin, the advantages over khellin being the greater therapeutic range and good solubility in water.

Es wurde nun gefunden, daß die als Salze ebenfalls gut wasserlöslichen 2-Phenyl-7-aminoalkoxy-chromone auf analogem Wege aus den Alkalisalzen des gegebenenfalls im Phenylkern substituierten 2-Phenyl-7-oxychromons und basisch substituierten Alkylhalogeniden in einem organischen Lösungsmittel herstellbar sind, jedoch in ihren pharmakologischen Eigenschaften den Produkten der obenerwähnten Patentschrift überlegen sind. Dies kommt besonders zum Ausdruck, wenn man die muskulotrop-spasmolytische Wirkung am Meerschweinchendarm prüft. Die Phenylchromone wirken in allen Fällen erheblich stärker und sind noch ungiftiger als die analogen Methylderivate. Zur Erläuterung diene folgende Tabelle: Pharmakologischer Vergleich von Verbindunzen der Formel R. Muskulotrop-spasmolytische Wirkung LDSO in rng/kg i. p. weiße Maus im Vergleich zu PAPAVERIN nach Miller und Tainter CH, @\ jN-CH2-CH2-CHZ- -CH3 0,017 155 CH, @@ - C611, 0,63 312 N -CH2-CH2- -CH, 0,03 135 @! - C,115 0,56 225 CH3 ;N-CH2-CH2- -CH3 0,04 382 CH, jl -C6H5 0,47 403 C, H5 , N - CH, - CH, - - CH, 0,037 207 C2 H5 - @' - C, H5 0,44 259 O N-CH2-CH2- -CH3 0,04 820 - @@ - C,115 0,26 > 1500 Am isolierten Meerschweinchenherzen wirken alle ntersuchten Substanzen ähnlich gut coronarerweiternd de die analog hergestellten Methylchromone, doch zeigen ich in einigen Fällen auch hier Vorteile. So zeigt das -(p-Methoxyphenyl)-7-(N-ß-dimethylaminoä.thoxy)-chroaon-hydrochlorid eine besonders starke Coronarerweiteung, die etwa das Siebenfache der Theophyllinwirkung rreicht, ohne daß dabei ein negativ inotroper Effekt uftritt, der bei den analoghergestellten Methylchromo-.en immer zu beobachten ist.It has now been found that the 2-phenyl-7-aminoalkoxy-chromones, which are likewise readily water-soluble as salts, can be prepared in an organic solvent in an analogous way from the alkali metal salts of the 2-phenyl-7-oxychromone optionally substituted in the phenyl nucleus and basic substituted alkyl halides, however, are superior in their pharmacological properties to the products of the above-mentioned patent specification. This is particularly evident when the musculotropic-spasmolytic effect is tested on the guinea pig intestine. The phenylchromones have a considerably stronger effect in all cases and are even less toxic than the analogous methyl derivatives. The following table serves as an explanation: Pharmacological comparison of compounds of the formula R. Musculotropic-spasmolytic effect of LDSO in rng / kg ip white mouse compared to PAPAVERIN according to Miller and Tainter CH, @ \ jN-CH2-CH2-CHZ- -CH3 0.017 155 CH, @@ - C6 11 , 0.63 312 N -CH2-CH2- -CH, 0.03 135 @! - C, 11 5 0.56 225 CH3 ; N-CH2-CH2- -CH3 0.04 382 CH, jl -C6H5 0.47 403 C, H5, N - CH, - CH, - - CH, 0.037 207 C2 H5 - @ '- C, H5 0.44 259 O N-CH2-CH2- -CH3 0.04 820 - @@ - C, 11 5 0.26> 1500 In the isolated guinea pig heart, all the substances investigated have a similarly good coronary-expanding effect as the analogously prepared methylchromones, but in some cases I show advantages here too. Thus, the - (p-methoxyphenyl) -7- (N-ß-dimethylaminoä.thoxy) -chroaon hydrochloride shows a particularly strong coronary expansion, which reaches about seven times the theophylline effect, without a negative inotropic effect occurring in the Analogously prepared methylchromo-.en can always be observed.

Zur Prüfung der peripheren Gefäßwirkung wurden Tersuche am isolierten, durchströmten Kaninchenohr .urchgeführt. In dieser Versuchsanordnung wirkten 00y7-Piperidinoäthoxy-2-phenyl-chromon-hydrochlorid twa viermal so stark wie 100y7-Piperidinoäthoxy-2-mehyl-chromon-hydrochlorid.To test the peripheral vascular effect, tests were carried out on isolated, perfused rabbit ear. 00y7-piperidinoethoxy-2-phenylchromone hydrochloride worked in this test arrangement about four times as strong as 100y7-piperidinoethoxy-2-methylchromone hydrochloride.

Beispiel 1 1,15 g Natrium werden in 65 ccm absolutem Methyllkohol gelöst und 12 g 7-Oxy-2-phenylchromon zuegeben. Man destilliert das Lösungsmittel auf dem Vasserbad im Vakuum ab und nimmt den Rückstand in '5 ccm absolutem Dioxan auf. Anschließend gibt man ine Lösung von 6,7 g N-r-Dimethylaminopropylchlorid a 20 ccm absolutem Dioxan dazu, rührt 4 Stunden bei '0 bis 100°C Innentemperatur und destilliert das Dioxan m Vakuum ab. Der Rückstand wird mit Wasser verührt, nach kurzem Stehen abgesaugt, mit Wasser geiaschen und im Exsikkator getrocknet. Die so erhaltene aase wird in absolutem Äthylalkohol gelöst und mit lkoholischer Salzsäure schwach angesäuert. Nach dem £bkühlen wird das reine 2-Phenyl-7-(N-y-dimethylminopropoxy)-chromon-hydrochlorid abgesaugt und in Ler Trockenpistole bei 130°C getrocknet. Man erhält ,5 g vom Schmelzpunkt 219 bis 220°C.Example 1 1.15 g of sodium are dissolved in 65 cc of absolute methyl alcohol dissolved and added 12 g of 7-oxy-2-phenylchromone. The solvent is distilled on the water bath in vacuo and the residue is taken up in 5 cc of absolute dioxane on. Then a solution of 6.7 g of N-r-dimethylaminopropyl chloride a is added Add 20 cc of absolute dioxane, stir for 4 hours at 0 to 100 ° C internal temperature and the dioxane is distilled off in a vacuum. The residue is stirred with water, after briefly standing with suction, washed with water and dried in a desiccator. the aase obtained in this way is dissolved in absolute ethyl alcohol and treated with alcoholic hydrochloric acid weakly acidified. After cooling, the pure 2-phenyl-7- (N-γ-dimethylminopropoxy) chromone hydrochloride is obtained Aspirated and dried in a Ler drying gun at 130 ° C. 5 g of melting point are obtained 219 to 220 ° C.

Beispiel 2 Es -wird analog wie im Beispiel 1 gearbeitet, jedoch vird an Stelle von N-r-Dimethylaminopropylchlorid d-ß-Chloräthyl-piperidin verwendet. Ausgehend von 0 g 7-Oxy-2-phenylchromon erhält man 22 g 2-Phenyl-'-(ß-piperidinoäthoxy)-chromon-hydrochlorid, das nach Lem Umkristallisieren aus Äthylalkohol bei 248 bis ;49°C schmilzt.Example 2 The procedure is analogous to that in Example 1, but the procedure is followed instead of N-r-dimethylaminopropyl chloride, d-ß-chloroethyl piperidine is used. Starting from 0 g of 7-oxy-2-phenylchromone, 22 g of 2-phenyl -'- (ß-piperidinoethoxy) -chromone hydrochloride are obtained, which, according to Lem, recrystallizes from ethyl alcohol at 248 to 49 ° C.

Beispiel 3 Es wird analog wie im Beispiel 1 gearbeitet, jedoch ,tird an Stelle von N-y-Dimethylaminopropylchlorid Nß-Di_methylaniinoäthylchloridverwendet. DerSchmelzpunkt des erhaltenen 2-Phenyl-7-(N-p-dimethylaminoäthoxy)-chromon-hydrochlorids beträgt 216 bis 220°C. Beispiel 4 Es wird analog wie im Beispiel 1 gearbeitet, jedoch wird an Stelle von N-y-Dimethylaminopropylchlorid N-ß-Diäthylaminoäthylchlorid verwendet. Der Schmelzpunkt des erhaltenen 2-Phenyl-7-(N-ß-diätbylaminoäthoxy)-chromon-hydrochlorids beträgt 187 bis 188°C. Beispiel 5 Es wird analog wie im Beispiel 1 gearbeitet, jedoch wird an Stelle von N-y-Dimethylaminopropylchlorid N-ß-Chloräthylmorpholin verwendet. Man erhält 2-Phenyl-7-(ß-morphohnoäthoxy)-chromon-hydrochlorid. vom Schmelzpunkt 253 bis 254°C.Example 3 The procedure is analogous to that in Example 1, but this is done instead of N-γ-dimethylaminopropyl chloride Nß-Di_methylaniinoäthylchlorid used. The melting point of the obtained 2-phenyl-7- (N-p-dimethylaminoethoxy) chromone hydrochloride is 216 to 220 ° C. Example 4 The procedure is analogous to that in Example 1, but N-ß-diethylaminoethyl chloride is used instead of N-γ-dimethylaminopropyl chloride. The melting point of the 2-phenyl-7- (N-ß-dietbylaminoethoxy) chromone hydrochloride obtained is 187 to 188 ° C. Example 5 The procedure is analogous to that in Example 1, but N-ß-chloroethylmorpholine is used instead of N-γ-dimethylaminopropyl chloride. 2-Phenyl-7- (ß-morphohnoethoxy) chromone hydrochloride is obtained. from the melting point 253 to 254 ° C.

Beispiel 6 Zu einer Lösung von 0,66 g Natrium in 100 ccm absolutemMethanol werden7,7 g 7-Oxy-2-(p-methoxyphenyl)-chromon zugesetzt. Man rührt, bis alles gelöst ist, und dampft im Vakuum zur Trockne ein. Der Rückstand wird in der Reibschale zerrieben, in 75 ccm reinem Dioxan suspendiert, und. dazu werden 3,4 g N-ß-Dimethylaminoäthylchlorid gegeben. Nun kocht man 3 Stunden unter Rühren am Rückfluß, destilliert das Dioxan im Vakuum ab und extrahiert den Rückstand mit Äther. Die nach dem Abdestillieren des Äthers erhaltene Base vom Schmelzpunkt 118 bis 119°C wird durch Lösen in Äthylalkohol, Ansäuern mit alkoholischer Salzsäure und Fällen mit absolutem Äther in das Hydrochlorid übergeführt. Man erhält so 8 g 2-(p-Methoxyphenyl)-7-(N-ß-dimethylaminoäthoxy)-chromon-hydrochlorid, das durch Umkristallisieren aus Isopropylalkohol gereinigt wird. Der Schmelzpunkt beträgt 220 bis 221°C.Example 6 To a solution of 0.66 g of sodium in 100 cc of absolute methanol 7.7 g of 7-oxy-2- (p-methoxyphenyl) chromone are added. Stir until everything is resolved is, and evaporated to dryness in a vacuum. The residue is in the mortar ground, suspended in 75 cc of pure dioxane, and. to this are 3.4 g of N-ß-dimethylaminoethyl chloride given. The mixture is then refluxed for 3 hours with stirring, and the dioxane is distilled in vacuo and the residue extracted with ether. The one after distilling off the base obtained from the ether with a melting point of 118 to 119 ° C is dissolved in ethyl alcohol, Acidification with alcoholic hydrochloric acid and precipitation with absolute ether into the hydrochloride convicted. This gives 8 g of 2- (p-methoxyphenyl) -7- (N-ß-dimethylaminoethoxy) chromone hydrochloride, which is purified by recrystallization from isopropyl alcohol. The melting point is 220 to 221 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N-substituierten, gegebenenfalls im Phenylkern substituierten 2-Phenyl-7-aminoalkoxy-chromonen, dadurch gekennzeichnet, daß man die Alkalisalze des gegebenenfalls im Phenylkern substituierten 2-Phenyl-7-oxychromons in einem organischen Lösungsmittel mit basisch substituierten Alkylhalogeniden umsetzt.PATENT CLAIM: Process for the production of N-substituted, optionally 2-phenyl-7-aminoalkoxy-chromones substituted in the phenyl nucleus, characterized in that that the alkali salts of the optionally substituted in the phenyl nucleus 2-phenyl-7-oxychromone Reacts in an organic solvent with basic substituted alkyl halides.
DEC16925A 1958-05-30 1958-05-30 Process for the preparation of N-substituted 2-phenyl-7-aminoalkoxy-chromones Pending DE1054091B (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DEC16925A DE1054091B (en) 1958-05-30 1958-05-30 Process for the preparation of N-substituted 2-phenyl-7-aminoalkoxy-chromones
CH7340459A CH378339A (en) 1958-05-30 1959-05-20 Process for the preparation of substituted 2-phenyl-7-aminoalkoxy-chromones
NL239670A NL103682C (en) 1958-05-30 1959-05-29
BE579151A BE579151A (en) 1958-05-30 1959-05-29 Process for the preparation of substituted 2-phenyl-7-aminoalkoxychromones
FR795451A FR478M (en) 1958-05-30 1960-08-30

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC16925A DE1054091B (en) 1958-05-30 1958-05-30 Process for the preparation of N-substituted 2-phenyl-7-aminoalkoxy-chromones

Publications (1)

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DE1054091B true DE1054091B (en) 1959-04-02

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CH (1) CH378339A (en)
DE (1) DE1054091B (en)
FR (1) FR478M (en)
NL (1) NL103682C (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1134384B (en) * 1960-10-18 1962-08-09 Hans Voigt Chem Pharm Fabrik D Process for the preparation of salts from xanthine acetic acid and flavone derivatives
US3079402A (en) * 1961-07-04 1963-02-26 Hans Voigt Chem Pharm Fabrik D Cero-chromonamino compounds
DE1174311B (en) * 1960-10-25 1964-07-23 Woelm Fa M Process for the preparation of N-substituted 4'-aminoalkoxy-2 ', 4-dihydroxy-chalcones and their salts
DE1193511B (en) * 1961-03-16 1965-05-26 Cassella Farbwerke Mainkur Ag Process for the preparation of derivatives of 7-oxychromone
DE1210883B (en) * 1961-11-09 1966-02-17 Cassella Farbwerke Mainkur Ag Process for the preparation of derivatives of 7-oxycoumarin
DE1210882B (en) * 1961-07-14 1966-02-17 Cassella Farbwerke Mainkur Ag Process for the preparation of derivatives of 7-oxychromone
DE1218452B (en) * 1959-10-14 1966-06-08 Recordati S P A Process for the preparation of hydrochlorides of basic esters of 3-methylflavone-8-carboxylic acid
DE1222072B (en) * 1961-03-06 1966-08-04 Voigt Dr Med Hans Process for the preparation of N-substituted 7-aminoalkoxyflavones
DE1223849B (en) * 1960-10-11 1966-09-01 Hans Voigt Chem Pharm Fabrik D Process for the preparation of lactic acid 7- (N-beta-dimethylaminoaethoxy) -flavone
DE1244192B (en) * 1959-10-20 1967-07-13 Recordati S P A Process for the production of hydrochlorides with basic substituted 3-methyl-flavones or -chromones
DE1270567B (en) * 1961-05-19 1968-06-20 Klinge Co Chem Pharm Fab Process for the production of basic substituted flavones
WO1991018597A1 (en) * 1990-06-04 1991-12-12 Erickson Ronald H Sigma binding site agents

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1188311A (en) * 1981-05-01 1985-06-04 Edwin S. Wu Antihypertensive agents
FR2689127B1 (en) * 1992-03-31 1994-05-06 Adir Cie NEWS 3 ', 5' -DITERTBUTYL-4'-HYDROXY FLAVONES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1218452B (en) * 1959-10-14 1966-06-08 Recordati S P A Process for the preparation of hydrochlorides of basic esters of 3-methylflavone-8-carboxylic acid
DE1244192B (en) * 1959-10-20 1967-07-13 Recordati S P A Process for the production of hydrochlorides with basic substituted 3-methyl-flavones or -chromones
DE1223849B (en) * 1960-10-11 1966-09-01 Hans Voigt Chem Pharm Fabrik D Process for the preparation of lactic acid 7- (N-beta-dimethylaminoaethoxy) -flavone
US3098854A (en) * 1960-10-18 1963-07-23 Hans Voigt Chem Pharm Fabrik D Acid addition salts of basically substituted flavones and preparation thereof
DE1134384B (en) * 1960-10-18 1962-08-09 Hans Voigt Chem Pharm Fabrik D Process for the preparation of salts from xanthine acetic acid and flavone derivatives
DE1174311B (en) * 1960-10-25 1964-07-23 Woelm Fa M Process for the preparation of N-substituted 4'-aminoalkoxy-2 ', 4-dihydroxy-chalcones and their salts
DE1222072B (en) * 1961-03-06 1966-08-04 Voigt Dr Med Hans Process for the preparation of N-substituted 7-aminoalkoxyflavones
DE1193511B (en) * 1961-03-16 1965-05-26 Cassella Farbwerke Mainkur Ag Process for the preparation of derivatives of 7-oxychromone
DE1270567B (en) * 1961-05-19 1968-06-20 Klinge Co Chem Pharm Fab Process for the production of basic substituted flavones
US3079402A (en) * 1961-07-04 1963-02-26 Hans Voigt Chem Pharm Fabrik D Cero-chromonamino compounds
DE1210882B (en) * 1961-07-14 1966-02-17 Cassella Farbwerke Mainkur Ag Process for the preparation of derivatives of 7-oxychromone
DE1210883B (en) * 1961-11-09 1966-02-17 Cassella Farbwerke Mainkur Ag Process for the preparation of derivatives of 7-oxycoumarin
WO1991018597A1 (en) * 1990-06-04 1991-12-12 Erickson Ronald H Sigma binding site agents
US5278174A (en) * 1990-06-04 1994-01-11 Scios Nova, Inc. Sigma binding site agents
US5359098A (en) * 1990-06-04 1994-10-25 Guilford Pharmaceuticals Inc. Intermediates for making sigma binding site agents

Also Published As

Publication number Publication date
BE579151A (en) 1959-11-30
FR478M (en) 1961-05-02
CH378339A (en) 1964-06-15
NL103682C (en) 1963-01-15

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