DE1199783B - Process for the preparation of basic thiophene derivatives - Google Patents

Process for the preparation of basic thiophene derivatives

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Publication number
DE1199783B
DE1199783B DED40401A DED0040401A DE1199783B DE 1199783 B DE1199783 B DE 1199783B DE D40401 A DED40401 A DE D40401A DE D0040401 A DED0040401 A DE D0040401A DE 1199783 B DE1199783 B DE 1199783B
Authority
DE
Germany
Prior art keywords
preparation
phenyl
thienyl
amino
thiophene derivatives
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
DED40401A
Other languages
German (de)
Inventor
Dr Kurt Thiele
Dr Klaus Posselt
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.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
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
Priority to DED37431A priority Critical patent/DE1194424B/en
Priority to CH1147162A priority patent/CH429760A/en
Priority to FI621835A priority patent/FI42572C/en
Priority to BR143797/62A priority patent/BR6243797D0/en
Priority to GB39127/62A priority patent/GB970445A/en
Priority to SE11930/62A priority patent/SE311168B/xx
Priority to DK483762AA priority patent/DK105813C/en
Priority to DK246264AA priority patent/DK105595C/en
Application filed by Degussa GmbH filed Critical Degussa GmbH
Priority to DED40401A priority patent/DE1199783B/en
Priority to DED40465A priority patent/DE1213851B/en
Priority to BE628104A priority patent/BE628104A/en
Priority to CH1267363A priority patent/CH471142A/en
Priority to SE13233/63A priority patent/SE309601B/xx
Priority to GB4730763A priority patent/GB1078118A/en
Publication of DE1199783B publication Critical patent/DE1199783B/en
Priority to FI691216A priority patent/FI42577C/en
Pending legal-status Critical Current

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Classifications

    • 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

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

Description

Verfahren zur Herstellung von basischen Thiophenderivaten Die Erfindung betrifft ein Verfahren zur Herstellung von basischen Thiophenderivaten der allgemeinen Formel in der R ein Wasserstoff- oder Chloratom oder eine Alkoxygruppe bedeutet, und deren Salzen.Process for the preparation of basic thiophene derivatives The invention relates to a process for the preparation of basic thiophene derivatives of the general formula in which R denotes a hydrogen or chlorine atom or an alkoxy group, and their salts.

Die Herstellung erfolgt dadurch, daß man in an sich bekannter Weise aus einer Verbindung der allgemeinen Formel in der R die angegebene Bedeutung hat, Wasser abspaltet. Die Wasserabspaltung erfolgt zweckmäßig in einem sauren Medium. vorzugsweise mit Mineralsäuren, Säurechloriden. Oxalsäure, Zinkchlorid Kaliumhydrogensulfat. Phosphorpentoxyd, rotem Phosphor und Jod oder Eisessig und bei erhöhter Temperatur. Die so erhaltenen Basen können in an sich bekannter Weise in ihre Salze übergeführt werden.The preparation is carried out by converting a compound of the general formula in a manner known per se in which R has the meaning given, splits off water. The elimination of water is expediently carried out in an acidic medium. preferably with mineral acids, acid chlorides. Oxalic acid, zinc chloride potassium hydrogen sulfate. Phosphorus pentoxide, red phosphorus and iodine or glacial acetic acid and at elevated temperature. The bases obtained in this way can be converted into their salts in a manner known per se.

Die hierfür verwendeten Ausgangsstoffe können gemäß dem in der deutschen Auslegeschrift beschriebenen Verfahren hergestellt werden. The starting materials used for this can be used in accordance with the German Auslegeschrift described method are produced.

Beispiel 1 2-{[3-Phenyl-3-thienyl-(2)-propen-(2)-yl-(1)]-amino}-3-phenylpropan-hydrocylorid 1. a) In eine Lösung von 40 g 2-{N-[3-Phenyl-3-thienyl-3-hydroxypropyl-(1)]}-amino-3-phenylpropan in 400 ml Eisessig wird 20 Minuten trockenes HCl-Gas eingeleitet. Anschließend wird 1 Stunde unter Rückfluß gekocht, der Eisessig abdestilliert. der Rückstand in Wasser gelöst und mit Ammoniak alkalisch gestellt. Das 2N-[3-Phenyl-3-thienyl-prnpen-(2)-yl-(1)D-amino-3-phenylpropan wird als Ul isoliert. Die Base wird mit isopropanolischer HCI neutralisiert und das HCI-Salz aus Isopropanol umkristallisiert; F. 174°C.Example 1 2 - {[3-Phenyl-3-thienyl- (2) -propen- (2) -yl- (1)] -amino} -3-phenylpropane hydrochloride 1. a) In a solution of 40 g of 2- {N- [3-phenyl-3-thienyl-3-hydroxypropyl- (1)]} - amino-3-phenylpropane in 400 ml of glacial acetic acid, dry HCl gas is added for 20 minutes initiated. The mixture is then refluxed for 1 hour and the glacial acetic acid is distilled off. the residue dissolved in water and made alkaline with ammonia. The 2N- [3-phenyl-3-thienyl-prnpen- (2) -yl- (1) D-amino-3-phenylpropane is isolated as Ul. The base is neutralized with isopropanolic HCl and the HCl salt is recrystallized from isopropanol; Mp 174 ° C.

1. b) 38,7 g (0,1 Mol) 2-(N-[3 -Phenyl-3-thienyl-3 - hydroxy - propyl - (1) 1}-amino-3-phenylpropan werden mit einem Gemisch aus 62 ml Eisessig. 0.4 g rotem Phosphor, 1,2 g Jod und 1,2 mol Wasser 2½ Stunden unter Rückfluß gekocht. nach beendeter Reaktionu wird in bekannter Weise aufgearbeitet, die ätherische Lösung eingeengt und die Base bei 0,5 mm und 280 bis 300"C C destilliert. 1. b) 38.7 g (0.1 mol) of 2- (N- [3-phenyl-3-thienyl-3-hydroxypropyl) - (1) 1} -amino-3-phenylpropane are mixed with a mixture of 62 ml of glacial acetic acid. 0.4 g red phosphorus, 1.2 g of iodine and 1.2 mol of water refluxed for 2½ hours. After the reaction has ended, the ethereal solution is worked up in a known manner concentrated and the base is distilled at 0.5 mm and 280 to 300 "C.

Beispiel 2 2-{[3-Phenyl-3-thienyl-(2)-propen-(2)-yl-(1)]-amino}-3-(p-chlorphenyl)-propan-hydrocylorid In eine Suspension von 9 g 2[3-Phenyl-3-thienyl-(2)-3-hydroxypropyl-(1)]-amino}-3-(p-chlorphenyl)-propna-hydrocylorid in 100 ml Eisessig wird so lange Chlorwasserstoff eingeleitet. bis alles gelöst ist.Example 2 2 - {[3-Phenyl-3-thienyl- (2) -propen- (2) -yl- (1)] -amino} -3- (p-chlorophenyl) -propane hydrochloride In a suspension of 9 g of 2 [3-phenyl-3-thienyl- (2) -3-hydroxypropyl- (1)] -amino} -3- (p-chlorophenyl) -propna-hydrocylorid in 100 ml of glacial acetic acid is so long Introduced hydrogen chloride. until everything is resolved.

Nach dem Abdestillieren des Eisessigs wird der Rückstand mit konzentriertem Ammoniak alkalisch gemacht und mit insgesamt 500 ml Ather extrahiert.After the glacial acetic acid has been distilled off, the residue is concentrated with Made ammonia alkaline and extracted with a total of 500 ml of ether.

Aus der getrockneten Ätherlösung wird mit isopropanolischer HCl - Lösung das 2-{[3-Phenyl-3 -thienyl-(2)-propen-(2)-yl -(l)j-amino}-3-(p-chlorphenyl)-propan-hydrochlorid erhalten (7 g, 810/0 Ausbeute). Aus Isopropanol umkristallisiert liegt der Schmelzpunkt bei 193 bis 194°C.From the dried ether solution isopropanolic HCl - Solution the 2 - {[3-phenyl-3-thienyl- (2) -propen- (2) -yl - (l) j-amino} -3- (p-chlorophenyl) propane hydrochloride obtained (7 g, 810/0 yield). The melting point is recrystallized from isopropanol at 193 to 194 ° C.

Beispiel 3 2-{ { [3-Phenyl-3-thienyl-(2)-propen-(2)-yl-(1)]-amino}-3-(p-methoxyphenyl)-propan-hydrochlorid 21 g 2-{N-[3-Phenyl-3-thienyl-(2)-3-hydroxypropyl-(l)l-amino)- 3-(p-methoxyphenyl) -propanhydrochlorid werden in 150 ml Eisessig mit HCl-Gas behandelt. bis alles gelöst ist. Dann wird das Lösungsmittel abdestilliert. der Rückstand mit wäßrigem Ammoniak alkalisch gemacht und die Base in Äther aufgenommen. Aus der ätherischen Lösung werden 14 g HCI-Salz gefällt und aus Äthanol umkristallisiert. F. 183 bis 184°C.Example 3 2- {{[3-Phenyl-3-thienyl- (2) -propen- (2) -yl- (1)] -amino} -3- (p-methoxyphenyl) -propane, hydrochloride 21 g of 2- {N- [3-phenyl-3-thienyl- (2) -3-hydroxypropyl- (l) l-amino) -3- (p-methoxyphenyl) propane hydrochloride are dissolved in 150 ml of glacial acetic acid with HCl gas treated. until everything is resolved. Then the solvent is distilled off. the residue was made alkaline with aqueous ammonia and the base was taken up in ether. 14 g of HCl salt are precipitated from the ethereal solution and recrystallized from ethanol. M.p. 183 to 184 ° C.

Es wurde gefunden. daß diese Verbindungen eine zentralstimulierende und coronargefäßerweiternde Wirkung besitzen. It was found. that these compounds have a central stimulatory effect and have coronary vasodilator effects.

In der folgenden Tabelle wird die Wirkung der Verfahrensprodukte gegenüber 1 -(3.4-Methylendioxybenzyl)-3-methyl-6. 6,7- methylendioxy- isochinolin (Papaverin) und dem bekannten 2-Äthyl-3-(3,5-dijod-4 - hydroxybenzoyl) - benzofuran (Benziodarone) verglichen. The following table shows the effect of the products of the process to 1 - (3,4-methylenedioxybenzyl) -3-methyl-6. 6,7-methylenedioxyisoquinoline (Papaverine) and the well-known 2-ethyl-3- (3,5-diiodo-4 - hydroxybenzoyl) - benzofuran (Benziodarone) compared.

Tabelle 1 Wirkung von 10 y je Injektion auf das Meerschweinchenherz Akute Toxizität Ver- in % der Ausgangswerte Maus per os bindung Coronar- Kontrak- Herz- L90 mgkg durch- tions- fr fluß amplitude frequenz A +145 +16 +8 391 B + 129 +23 +7 >3 000 C +135 -1 +7 >25 600 D +74 +21 +8 383 E +104 +14 +8 461 A = 24 [3-Phenyl-3-thienyl-(2)-propen-(2)-yl-( 1)]-amino}-3-phenyl-propan-hydrochlorid, B = 24 [3-Phenyl-3-thienyl-(2)-propen-(2)-yl-(1)]-amino}-3-(p-chlorphenyl)-propanhydrochlorid, C=2-{[3-Phenyl-3-thienyl-(2)-propen-(2)-yl-(1)]-amino}-3-(p-methoxyphenyl)-propanhydrochlorid, D 1 -(3,4-Methylendioxy-benzyl)-3-methyl-6.7-methylendioxy-isochinolin (= Papaverin), E = 2-Äthyl-3-(3,5-dijod-4-hydroxy-benzoyl)-benzofuran (= Benziodarone).Table 1 Effect of 10 y per injection Acute toxicity on the guinea pig heart Ver in% of the initial values mouse per os binding coronary contra heart L90 mgkg through- fr flow amplitude frequency A +145 +16 +8 391 B + 129 +23 +7> 3 000 C +135 -1 +7> 25 600 D +74 +21 +8 383 E +104 +14 +8 461 A = 24 [3-phenyl-3-thienyl- (2) -propen- (2) -yl- (1)] -amino} -3-phenyl-propane hydrochloride, B = 24 [3-phenyl-3- thienyl- (2) -propen- (2) -yl- (1)] - amino} -3- (p-chlorophenyl) propane hydrochloride, C = 2 - {[3-phenyl-3-thienyl- (2) - propen- (2) -yl- (1)] - amino} -3- (p-methoxyphenyl) propane hydrochloride, D 1 - (3,4-methylenedioxy-benzyl) -3-methyl-6,7-methylenedioxy-isoquinoline (= Papaverine), E = 2-ethyl-3- (3,5-diiodo-4-hydroxy-benzoyl) -benzofuran (= benziodarone).

Wie Tabelle I zeigt, haben alle untersuchten Verbindungen die gleiche geringe Wirkung auf die Herzfrequenz des Meerschweinchenherzens. Auch der Einfluß auf die Kontraktionsamplitude ist praktisch bei allen Verbindungen im Bereich der biologischen Streuung äußerst gering. As Table I shows, all compounds tested have the same little effect on the heart rate of the guinea pig heart. Also the influence on the contraction amplitude is practically in all connections in the range of biological dispersion is extremely low.

Die Wirkung auf den Coronardurchfluß ist bei den Verfahrensprodukten etwa doppelt so stark wie die des Papaverins. Auch gegenüber Benziodarone sind sie in der coronarerweiternden Wirkung deutlich überlegen; die Steigerung des Coronardurchflusses ist etwa 1,3mal so stark wie die des Benziodarone. The effect on coronary flow is on the products of the process about twice as strong as that of papaverine. They are also opposite to benziodarone clearly superior in the coronary-expanding effect; the increase in coronary flow is about 1.3 times as strong as that of Benziodarone.

Zieht man auch die Toxizität in die Betrachtung ein, so sind die Verfahrensprodukte besser verträglich als Papaverin und mit Ausnahme von Verbindung A auch weniger toxisch als Benziodarone. If you also take toxicity into consideration, they are Process products better tolerated than papaverine and with the exception of compound A also less toxic than Benziodarone.

Das praktisch verwertbare Maß der Verträglichkeit ist aber nicht die akute Toxizität der Verbindungen selbst, sondern die therapeutische Breite, d. h. die Sicherungsspanne in der Dosierung von der therapeutischen zur toxischen Dosis. Die für die Bestinimung der therapeutischen Breite maßgeblichen Daten - etwa äquieffektive Dosen - sind in Tabelle 2 zusammengestellt. The practically usable degree of tolerance is not the acute toxicity of the compounds themselves, but the therapeutic breadth, d. H. the safety margin in the dosage from the therapeutic to the toxic Dose. The relevant data for determining the therapeutic range - for example Equieffective doses - are summarized in Table 2.

Tabelle 2 Quotient Wirkung am den Ver- Dosis γ je LD50 mg/kg Coronardurchfluß bindung Injektion % therapeutische Dosis A 5 118 78 200 B 10 129 >300 000 C 10 135 >2 560 000 D 40 122 9575 E 10 104 46100 Die Tabelle 2 beweist, daß die therapeutische Breite bei sämtlichen Verfahrensprodukten gegenüber den Vergleichssubstanzen wesentlich größer und damit besser ist.Table 2 quotient Effect on the Ver dose γ per LD50 mg / kg Coronary flow bond injection% therapeutic dose A 5 118 78 200 B 10 129> 300 000 C 10 135> 2 560 000 D 40 122 9575 E 10 104 46 100 Table 2 shows that the therapeutic range for all process products is significantly greater and therefore better than the comparison substances.

Mit diesen Daten ist der Nachweis erbracht, daß die Verfahrensprodukte einen stärkeren positiven Effekt auf den Coronardurchfluß haben als die Vergleichssubstanzen. In der Anwendung und Handhabung in der Praxis übertreffen sie auf Grund der größeren therapeutischen Breite bei weitem die Präparate Papaverin und Benziodarone. These data provide evidence that the process products have a stronger positive effect on the coronary flow than the comparison substances. In the application and handling in practice they surpass due to the larger ones therapeutic range by far the preparations papaverine and benziodarone.

Methodik Die Herzwirkung der Verbindungen wurde in Anlehnung an die Methode von Langendorff (Pflügers Archiv, 61, S. 219, 1895) in der heute international gültigen Form durchgeführt. Dabei wurden der Coronardurchfluß, die Kontraktionsamplitude und die Herzfrequenz nach Injektion der Testsubstanzen gemessen. Methodology The cardiac action of the compounds was based on the Method of Langendorff (Pflügers archive, 61, S. 219, 1895) in the today international valid form carried out. The coronary flow, the contraction amplitude and the heart rate measured after injection of the test substances.

Die akute Toxizität wurde nach der Methode von M i 11 e r und T a i n t e r (Proc. Soc. Exper. Biol. and Med., 57, S.261. 1944) ermittelt. Die Beobachtungszeit betrug 24 Stunden. The acute toxicity was determined using the method of M i 11 e r and T a i n t e r (Proc. Soc. Exper. Biol. and Med., 57, p.261. 1944). The observation time was 24 hours.

Claims (1)

Patentanspruch: Verfahren zur Herstellung von basischen Thiophenderivaten der allgemeinen Formel in der R ein Wasserstoff- oder Chloratom oder eine Alkoxygruppe bedeutet. und deren Salzen, dadurch gekennzeichnet, daß man in an sich bekannter Weise aus einer Verbindung der allgemeinen Formel Wasser abspaltet.Claim: Process for the preparation of basic thiophene derivatives of the general formula in which R denotes a hydrogen or chlorine atom or an alkoxy group. and their salts, characterized in that in a manner known per se from a compound of the general formula Splits off water. In Betracht gezogene Druckschriften: Britische Patentschriften Nr. 657 301. 702 269 ; französische Patentschrift Nr. 1 218 631. Documents considered: British Patent Specification No. 657 301,702,269; French patent specification No. 1 218 631.
DED40401A 1961-11-10 1962-11-30 Process for the preparation of basic thiophene derivatives Pending DE1199783B (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
DED37431A DE1194424B (en) 1961-11-10 1961-11-10 Process for the preparation of basic thiophene derivatives
CH1147162A CH429760A (en) 1961-11-10 1962-09-28 Process for the preparation of new pharmaceutically valuable compounds
FI621835A FI42572C (en) 1961-11-10 1962-10-11 Process for the preparation of therapeutically valuable basic thiophene derivatives
BR143797/62A BR6243797D0 (en) 1961-11-10 1962-10-15 PROCESS TO PRODUCE NEW VALUABLE PHARMACEUTICAL COMPOUNDS
GB39127/62A GB970445A (en) 1961-11-10 1962-10-16 Thiophene derivatives
SE11930/62A SE311168B (en) 1961-11-10 1962-11-07
DK246264AA DK105595C (en) 1961-11-10 1962-11-09 Process for the preparation of basic thiophene derivatives or salts or quaternary ammonium compounds thereof.
DK483762AA DK105813C (en) 1961-11-10 1962-11-09 Process for the preparation of basic thiophene derivatives or salts or quaternary ammonium compounds thereof.
DED40401A DE1199783B (en) 1962-11-30 1962-11-30 Process for the preparation of basic thiophene derivatives
DED40465A DE1213851B (en) 1961-11-10 1962-12-07 Process for the preparation of new pharmaceutically valuable thiophene compounds
BE628104A BE628104A (en) 1961-11-10 1963-02-06 Process for the preparation of novel phenyl-thienyl-alkanos derivatives
CH1267363A CH471142A (en) 1962-11-30 1963-10-16 Process for the preparation of new pharmaceutically valuable thiophene compounds
SE13233/63A SE309601B (en) 1961-11-10 1963-11-29
GB4730763A GB1078118A (en) 1962-11-30 1963-11-29 Pharmaceutically valuable thiophene compounds
FI691216A FI42577C (en) 1961-11-10 1969-04-24 Method for the preparation of basic thiophene derivatives affecting the cardiac circulation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED40401A DE1199783B (en) 1962-11-30 1962-11-30 Process for the preparation of basic thiophene derivatives

Publications (1)

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DE1199783B true DE1199783B (en) 1965-09-02

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DED40401A Pending DE1199783B (en) 1961-11-10 1962-11-30 Process for the preparation of basic thiophene derivatives

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GB (1) GB1078118A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1921453C3 (en) * 1969-04-26 1973-04-19 Degussa Basic dithienyl derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB657301A (en) * 1948-02-25 1951-09-19 Wellcome Found Improvements in and relating to the preparation of substituted amino-alcohols and derivatives thereof
GB702269A (en) * 1950-01-06 1954-01-13 Wellcome Found Tertiary allylamines of therapeutic value and the production thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB657301A (en) * 1948-02-25 1951-09-19 Wellcome Found Improvements in and relating to the preparation of substituted amino-alcohols and derivatives thereof
GB702269A (en) * 1950-01-06 1954-01-13 Wellcome Found Tertiary allylamines of therapeutic value and the production thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1921453C3 (en) * 1969-04-26 1973-04-19 Degussa Basic dithienyl derivatives

Also Published As

Publication number Publication date
GB1078118A (en) 1967-08-02

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