DE3242204A1 - Process for the preparation of aminoalkylfurans or -thiophenes - Google Patents

Process for the preparation of aminoalkylfurans or -thiophenes

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Publication number
DE3242204A1
DE3242204A1 DE19823242204 DE3242204A DE3242204A1 DE 3242204 A1 DE3242204 A1 DE 3242204A1 DE 19823242204 DE19823242204 DE 19823242204 DE 3242204 A DE3242204 A DE 3242204A DE 3242204 A1 DE3242204 A1 DE 3242204A1
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Prior art keywords
formula
compound
preparation
aminoalkylfurans
thiophenes
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DE19823242204
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German (de)
Inventor
Des Erfinders Auf Nennung Verzicht
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Laboratories Pharmedical SA
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Laboratories Pharmedical SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Abstract

In the preparation of aminoalkylfurans or -thiophenes of the formula (I) <IMAGE> in which R1, R2 and R3 denote H, CH3, C2H5, C3H5 or C3H7 and X is O or S, 1-nitro-2,2-bis(methylthio)ethylene is reacted with a compound of the formula (II) <IMAGE> in which R1 and R2 have the abovementioned meaning, and the reaction product is reacted with an aliphatic amine of the formula R3-NH2 in which R3 has the abovementioned meaning, as a result of which the compounds of the formula (I) are obtained.

Description

Verfahren zur Herstellung von Aminoalkylfuranen oderProcess for the preparation of aminoalkylfurans or

-thiophenen Die Erfindung betrifft die Herstellung von Aminoalkylfuranen oder -thiophenen, die antisekretorische Magenmittel sind. -thiophenes The invention relates to the preparation of aminoalkylfurans or thiophenes, which are gastric antisecretory agents.

Diese Verbindungen haben die allgemeine Formel (I): worin R1, R2 und 3 H, CH3, C2H5 oder C3H7 sein können und X 0 oder S ist. Diese Verbindungen sind wertvolle Mittel, die die Wirkung der H2-Histaminrezeptoren hemmen, wobei letztere für die Magensekretion verantwortlich sind.These compounds have the general formula (I): wherein R1, R2 and 3 can be H, CH3, C2H5 or C3H7 and X is 0 or S. These compounds are valuable agents that inhibit the action of the H2-histamine receptors, the latter being responsible for gastric secretion.

Somit verursachen die erfindungsgemäßen Verbindungen entweder alleine oder in Kombination mit anderen aktiven Substanzen eine Verminderung der Hypersekretion und können daher als Mittel bei der Therapie von Magen- oder VerdauungsgeschwLiren verwendet werden.Thus, the compounds of the invention cause either alone or in combination with other active substances a reduction in hypersecretion and can therefore be used as an agent in the therapy of gastric or digestive ulcers be used.

In einigen Literaturstellen sind die pharmakologischen Eigenschaften dieser Substanzen beschrieben, etwa in Scand. J. Gastroenterol. Band 15, 249, 1980; Agents Actions Band 10, 190, 1980; Lancet Band 2, 1071, 1979; Lancet Band 1, 690, 1979.In some references the pharmacological properties are of these substances, for example in Scand. J. Gastroenterol. Vol. 15, 249, 1980; Agents Actions Vol. 10, 190, 1980; Lancet Vol. 2, 1071, 1979; Lancet Volume 1, 690, 1979.

Aufgabe der vorliegenden Erfindung ist die Bereitstellung eines verbesserten Verfahrens für die Herstellung der Verbindungen mit der Formel (I).The object of the present invention is to provide an improved one Process for the preparation of the compounds of formula (I).

Das erfindungsgemäße Verfahren kann schematisch wie folgt dargestellt werden: 1) 1. Stufe In der ersten Stufe werden die Verbindungen mit den Formeln (II) und (III) bei einer Temperatur zwischen -200C und +10 0C in Gegenwart von LösungsmittelnJwie niedermolekulare Alkohole, Acetonitril oder Aceton umgesetzt, wobei die Verbindung (IV) erhalten wird: worin R1, R2 und X die vorstehend angegebene Bedeutung besitzen.The process according to the invention can be shown schematically as follows: 1) 1st stage In the first stage, the compounds with the formulas (II) and (III) are at a temperature between -200C and +10 0C in the presence of solvents such as low molecular weight alcohols, acetonitrile or acetone reacted, whereby the compound (IV) is obtained: in which R1, R2 and X are as defined above.

2) 2.Stufe Die vorstehend erhaltene Verbindung (IV) wird mit einem niedermolekularen aliphatiscten (V) der Formel R3NH2 unter Verwendung von niedermolekularen Alkoholen, Acetonitril oder Aceton als Lösungsmittel bei einer Temperatur im Bereich-von 100C bis zum Siedepunkt des Lösungsmittels umgesetzt, wobei Verbindungen der Formel (I) erhalten werden.2) 2nd stage The compound (IV) obtained above is treated with a low molecular weight aliphatic (V) of the formula R3NH2 using low molecular weight Alcohols, acetonitrile or acetone as solvents at a temperature in the range-from 100C implemented up to the boiling point of the solvent, with compounds of the formula (I) can be obtained.

Die Verbindungen der Formel (1) liegen in Form der physiologisch verträglichen Salze, etwa Hydrochloride, Sulfate usw. vor.The compounds of the formula (1) are in the form of the physiologically tolerated ones Salts such as hydrochloride, sulfate, etc.

Die pharmakologischen Effekte der meisten aktiven Verbindungen sind solche, wie sie nachstehend angegeben sind und mit Hilfe der Magenperfusionstechnik in Ratten aufgefunden wurden, und wie es in der Literatursteile G.The pharmacological effects of most of the active compounds are those as given below and using the gastric perfusion technique were found in rats, and as it is in the literature parts G.

Schild, Brit. J. Pharmacol. 1958, 13, 54; Arzn. Forsch 1978, 7, 1124 beschrieben worden ist, indem die H+-Produktionsrate alle 10 min während einer konstanten Infusion von Histamin gemessen wurde.Shield, Brit. J. Pharmacol. 1958, 13, 54; Medic. Forsch 1978, 7, 1124 has been described by increasing the H + production rate every 10 min during a constant Infusion of histamine was measured.

Die folgenden Ergebnisse wurden im Vergleich mit der akuten Toxizität erzielt. oral Arzneimittel ED50 LD50 verab- reicht Kontrolle Histamin 100µg/kg/min) zwischen 40 und 50 Minuten lang laute 633 µ Äqu.II %o S.E. + 63 u.H+ CIMETIDIN 52µg/Kg.i.v. 1900 mg/kg Beispiel 1 12 µg/Kg.i.v. 1495 mg/kg Beispiel 2 28µg/Kg. i.v. Beispiel 3 4aj'gtKg. i.v. The following results were obtained in comparison with the acute toxicity. orally Drug ED50 LD50 administered enough control Histamine 100µg / kg / min) between 40 and 50 minutes long loud 633 µ equiv. II% o SE + 63 and H + CIMETIDINE 52µg / Kg.iv 1900 mg / kg Example 1 12 µg / kg iv 1495 mg / kg Example 2 28µg / kg. iv Example 3 4aj'gtKg. iv

Beispiel 1 (X = O;R1=R2=R3CH3) Synthese von N-Methyl, N'- {2- [5-(N,N-dimethylaminoethyl) -2-furoylmethyl-thio3 -ethyl -2-nitro-1,1-ethendiamin.Example 1 (X = O; R1 = R2 = R3CH3) Synthesis of N-methyl, N'- {2- [5- (N, N-dimethylaminoethyl) -2-furoylmethyl-thio3-ethyl -2-nitro-1,1-ethenediamine.

In einem geeigneten Kolben werden 216 g 2-[5-(N,N-Dimethyl aminoethyl)-2-furoylmethylthio] -ethanamin, 190 g l-Nitro-2,2-bis(methylthio)ethylen und 2500 ml Aceton eingebracht.In a suitable flask, 216 g of 2- [5- (N, N-dimethyl aminoethyl) -2-furoylmethylthio] -ethanamine, 190 g of l-nitro-2,2-bis (methylthio) ethylene and 2500 ml of acetone were introduced.

Die Mischung wird 10 Stunden lang gerührt, wobei die Temperatur zwischen -15°C und -10°C gehalten wird. Das Lösungsmittel wird dann unter Vakuum bei einer Temperatur von nicht mehr als 200C verdampft. Das resultierende gelbe 01 wird in der nächsten Stufe verwendet. Der Rückstand wird mit 200 ml einer 20 %igen Lösung von Methylamin in Methanol versetzt und die Mischung 8 Stunden lang auf 400C erhitzt. Danach wird das Lösungsmittel unter Vakuum abgedampftJund es wird ein Öl erhalten, das in 750 ml Aceton aufgenommen, bei 400C aufgelöst, mit Aktivkohle versetzt und filtriert wird. Die Acetonlösung-wird auf 0-5°C gekühlt, und eine 40 %ige Lösung von Chlorwasserstoff in Isopropanol wird tropfenweise unter RUhren hinzugegeben. Die Mischung wird 2 Stunden lang stehengelassen, bis das Produkt auskristallisiert ist, dann filtriert und mit kleinen Mengen wasserfreiem Aceton gewaschen. Ausbeute: 125 g (als HCl) Schmelzpunkt: 133-135°C.The mixture is stirred for 10 hours, the temperature between -15 ° C and -10 ° C is maintained. The solvent is then under vacuum at a Vaporizes at a temperature not exceeding 200C. The resulting yellow 01 will be in used in the next stage. The residue is mixed with 200 ml of a 20% solution methylamine in methanol is added and the mixture is heated to 40.degree. C. for 8 hours. The solvent is then evaporated off in vacuo and an oil is obtained, that was taken up in 750 ml of acetone, dissolved at 400C, mixed with activated charcoal and is filtered. The acetone solution is cooled to 0-5 ° C, and a 40% solution of hydrogen chloride in isopropanol is added dropwise with stirring. The mixture is left to stand for 2 hours until the product crystallizes out is then filtered and washed with small amounts of anhydrous acetone. Yield: 125 g (as HCl) melting point: 133-135 ° C.

Beispiel 2 (X = O; R1=R2=CH3; R3=02H5) Synthese von N-Ethyl-N' - {2-[5-(N,N-dimethylaminoethyl) - 2-5-(N,N-dimethylaminoethyl) -2-furoylmethylthioethyl -2-nitro-1,1-ethendiamin.Example 2 (X = O; R1 = R2 = CH3; R3 = 02H5) Synthesis of N-Ethyl-N '- {2- [5- (N, N-dimethylaminoethyl) - 2-5- (N, N-dimethylaminoethyl) -2-furoylmethylthioethyl -2-nitro-1,1-ethenediamine.

In einem Kolben werden 8,1 g 2- 5-(N,N-dimethylaminoethyl) -2-furoylmethylthio b-ethanamin und 7 g 1-Nitro-2,2-bis-(methylthio)-ethylen in 150 g Acetonitril bei OOC 8 Stunden lang gerührt. Anschließend werden 15 ml einer 35 %igen Lösung von Ethylamin in Acetonitril vorsichtig hinzugege- ben. Das RUhren wird 6 Stunden lang unter Rückflußbedingungen fortgesetzt.In a flask, 8.1 g of 2- 5- (N, N-dimethylaminoethyl) -2-furoylmethylthio b-ethanamine and 7 g of 1-nitro-2,2-bis- (methylthio) -ethylene in 150 g of acetonitrile Stirred OOC for 8 hours. Then 15 ml of a 35% solution of Carefully added ethylamine in acetonitrile ben. The stirring will Continued for 6 hours under reflux conditions.

Die Mischung wird gekUhlt und unter Vakuum konzentriert und der resultierende RUckstand wird in einer Silicalgelchromatographiesäule eingebracht und mit Ethylacetat/Methanol (2:1) eluiert.The mixture is cooled and concentrated under vacuum and the resulting The residue is placed in a silica gel chromatography column and washed with ethyl acetate / methanol (2: 1) eluted.

Bei de-r Lösungsmittelverdampfung wird ein öliger Rückstand erhalten, der in 30 ml einer Lösung von Chlorwasserstoff in Methanol suspendiert wird. Danach wird die Mischung 2 Stunden lang gerührt, wonach ein weißer Niederschlag erhalten wird, der filtriert und getrocknet wird. Ausbeute: 6,2 g, Schmelzpunkt: 132-134°C (als HCl) Beispiel 3 (X = R1 R1=R2=C2H5; R3=CH3) Synthese von N-Methyl-N'-{2-[5-(N,N-diethylaminoethyl) -2-thienylmethylthioj -ethylj -2-nitro-l, 1-ethendiamin.On evaporation of the solvent, an oily residue is obtained, which is suspended in 30 ml of a solution of hydrogen chloride in methanol. Thereafter the mixture is stirred for 2 hours after which time a white precipitate is obtained which is filtered and dried. Yield: 6.2 g, melting point: 132-134 ° C (as HCl) Example 3 (X = R1 R1 = R2 = C2H5; R3 = CH3) Synthesis of N-methyl-N '- {2- [5- (N, N-diethylaminoethyl) -2-thienylmethylthioj -ethylj -2-nitro-1,1-ethenediamine.

Ein Kolben wird mit 250 g 2- r5-(N, N-Diethylaminomethyl ) 2-tienylmethylthioJ -ethanamin und 170 g 1-Nitro-2,2-bis (methylthio)-ethylen in 1500 ml Methanol beschickt, wobei die Mischung 8 Stunden lang bei -150C gerUhrt wird.A flask is filled with 250 g of 2- r5- (N, N-diethylaminomethyl) 2-tienylmethylthioJ -ethanamine and 170 g of 1-nitro-2,2-bis (methylthio) -ethylene charged in 1500 ml of methanol, the mixture is stirred for 8 hours at -150C.

Das Lösungsmittel wird danach unter Vakuum abgedampft und das rückständige, schwach gelbe Öl wird auf einer Silicalgelsäule chromatographiert und mit Ethylacetat/Methanol (2:1) eluiert.The solvent is then evaporated off under vacuum and the remaining, pale yellow oil is chromatographed on a silica gel column and washed with ethyl acetate / methanol (2: 1) eluted.

Nachdem das Lösungsmittel verdampft worden ist, wird das resultierende Öl in Acetonitril suspendiert und mit 200 ml einer 30 %igen Lösung von Methylamin in Acetonitril versetzt. Die Mischung wird 2 Stunden lang unter Rückfluß gekocht, konzentriert und der Rückstand wird mit 1200 ml Isopropanol aufgenommen, wobei eine Lösung von Chlorwasserstoff in Isopropancl unter kühlen Bedingungen tropfenweise hinzugesetzt wird.After the solvent is evaporated, the resulting Oil suspended in acetonitrile and with 200 ml of a 30% solution of methylamine added in acetonitrile. The mixture is refluxed for 2 hours, concentrated and the residue with 1200 ml Isopropanol added, taking a solution of hydrogen chloride in isopropane under cool conditions dropwise is added.

Nach der Kristallisation wird das Produkt filtriert und getrocknet. Ausbeute: 120 g. Schmelzpunkt: 105-108°C.After crystallization, the product is filtered and dried. Yield: 120 g. Melting point: 105-108 ° C.

Claims (1)

Patentanspruch Verfahren zur Herstellung von Aminoalkylfuranen oder -thiophenen mit der Formel (1): worin R1, R2 und R3 H, CH3, C2H5 und C3H7 sein können und X S oder 0 ist, dadurch gekennzeichnet, daß man in einer ersten Stufe eine Verbindung der Formel (11) worin R1 und R2 die vorstehend angegebene Bedeutung besitzt, mit i-Nitro-2,2-bis-(methylthio)-ethylen bei einer Temperatur im Bereich von -20 0C bis +10 0C und in Gegenwart eines Lösungsmittels aus der Gruppe niedermolekulare Alkohole, Acetonitril und Aceton umsetzt, wobei die Verbindung der Formel (IV) erhalten wird: und in einer zweiten Stufe die Verbindung mit der Formel (IV) mit einem aliphatischen Amin der Formel R3-NH2, worin R3 die.vorstehend angegebene Bedeutung besitzt, bei einer Temperatur zwischen 10 0C und der Siedetemperatur eines Lösungsmittels aus der Gruppe niedermolekulare Alkohol, Acetonitril und Aceton umsetzt, wobei die Verbindung der Formel (I) erhalten wird.Claim process for the preparation of aminoalkylfurans or thiophenes with the formula (1): wherein R1, R2 and R3 can be H, CH3, C2H5 and C3H7 and XS or 0, characterized in that in a first stage a compound of the formula (11) wherein R1 and R2 have the meaning given above, with i-nitro-2,2-bis- (methylthio) -ethylene at a temperature in the range from -20 0C to +10 0C and in the presence of a solvent from the group of low molecular weight alcohols, Acetonitrile and acetone reacts, the compound of the formula (IV) being obtained: and in a second stage the compound of the formula (IV) with an aliphatic amine of the formula R3-NH2, in which R3 has the meaning given above, at a temperature between 10 ° C. and the boiling point of a solvent from the group of low molecular weight alcohol, acetonitrile and acetone to give the compound of formula (I).
DE19823242204 1981-11-16 1982-11-15 Process for the preparation of aminoalkylfurans or -thiophenes Ceased DE3242204A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES507180A ES507180A0 (en) 1981-11-16 1981-11-16 PROCEDURE FOR THE PREPARATION OF AMINO ALCOSI FURANOS OR TIOPHENES.

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DE3242204A1 true DE3242204A1 (en) 1983-05-26

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JP (1) JPS5890574A (en)
CH (1) CH650505A5 (en)
DE (1) DE3242204A1 (en)
ES (1) ES507180A0 (en)
IT (1) IT1156325B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3343884A1 (en) * 1982-12-08 1984-06-14 Degussa Ag, 6000 Frankfurt Novel ethenediamine and guanidine derivatives
AT391470B (en) * 1985-01-11 1990-10-10 Richter Gedeon Vegyeszet METHOD FOR PRODUCING 1- (2- (5HU850111104 / 85
AT392944B (en) * 1984-12-04 1991-07-10 Fendt & Co Xaver BRAKE DEVICE FOR TRAILER TRAILERS
US6062226A (en) * 1996-06-13 2000-05-16 Japan Tobacco Inc. Cigarette manufacturing apparatus

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3784698D1 (en) * 1987-04-06 1993-04-15 Heumann Pharma Gmbh & Co METHOD FOR PRODUCING NITROETHENE DERIVATIVES.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2734070A1 (en) * 1976-08-04 1978-02-09 Allen & Hanburys Ltd AMINOALKYLFURA DERIVATIVES, PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2734070A1 (en) * 1976-08-04 1978-02-09 Allen & Hanburys Ltd AMINOALKYLFURA DERIVATIVES, PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chem. Abstr. 98, 1983, 179196 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3343884A1 (en) * 1982-12-08 1984-06-14 Degussa Ag, 6000 Frankfurt Novel ethenediamine and guanidine derivatives
AT392944B (en) * 1984-12-04 1991-07-10 Fendt & Co Xaver BRAKE DEVICE FOR TRAILER TRAILERS
AT391470B (en) * 1985-01-11 1990-10-10 Richter Gedeon Vegyeszet METHOD FOR PRODUCING 1- (2- (5HU850111104 / 85
US6062226A (en) * 1996-06-13 2000-05-16 Japan Tobacco Inc. Cigarette manufacturing apparatus

Also Published As

Publication number Publication date
IT1156325B (en) 1987-02-04
ES8206506A1 (en) 1982-08-16
JPS5890574A (en) 1983-05-30
ES507180A0 (en) 1982-08-16
CH650505A5 (en) 1985-07-31
IT8224214A0 (en) 1982-11-12

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