DE1292652B - Basically substituted esters of trisubstituted acrylic acids, their hydrochlorides and processes for their preparation - Google Patents

Basically substituted esters of trisubstituted acrylic acids, their hydrochlorides and processes for their preparation

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Publication number
DE1292652B
DE1292652B DEG46252A DEG0046252A DE1292652B DE 1292652 B DE1292652 B DE 1292652B DE G46252 A DEG46252 A DE G46252A DE G0046252 A DEG0046252 A DE G0046252A DE 1292652 B DE1292652 B DE 1292652B
Authority
DE
Germany
Prior art keywords
trisubstituted
hydrochlorides
acrylic acids
general formula
substituted esters
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
DEG46252A
Other languages
German (de)
Inventor
Eissler
Dipl-Chem Dr Horst
Heinrich
Dipl-Chem Dr Werner
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.)
BK Giulini Chemie GmbH
Original Assignee
Giulini Gebrueder 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
Application filed by Giulini Gebrueder GmbH filed Critical Giulini Gebrueder GmbH
Priority to DEG46252A priority Critical patent/DE1292652B/en
Priority to AT177867A priority patent/AT271454B/en
Priority to ES337592A priority patent/ES337592A1/en
Priority to NL6703540A priority patent/NL6703540A/xx
Priority to BE695052D priority patent/BE695052A/xx
Priority to CH329167A priority patent/CH478090A/en
Priority to FR69048367A priority patent/FR1536213A/en
Priority to DK116867A priority patent/DK114548B/en
Priority to GB1075667A priority patent/GB1139994A/en
Priority to SE317367A priority patent/SE315881B/xx
Publication of DE1292652B publication Critical patent/DE1292652B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

Aus der USA.-Patentschrift 2 673 853 ist es bekannt, daß quartäre Salze von basischen Estern Irisubstituierter Acrylsäuren der allgemeinen FormelIt is known from US Pat. No. 2,673,853 that quaternary salts of basic esters Iris-substituted acrylic acids of the general formula

ArsArs

Ar'Ar '

: == C — COO —Alk — Ν—R' A X R": == C - COO —Alk - Ν — R 'AX R "

in der R gleich Wasserstoff oder Alkyl bedeutet, wertvolle pharmakologische Eigenschaften haben. Besonders blockieren sie sowohl sympathische wie auch parasympathische Nervenimpulse.in which R is hydrogen or alkyl, have valuable pharmacological properties. In particular, they block both sympathetic and parasympathetic nerve impulses.

überraschenderweise hat sich nun gezeigt, daß ähnliche Verbindungen eine hervorragende entzündungshemmende Wirkung mit nur geringer Giftigkeit haben. Diese Verbindungen haben die allgemeine FormelSurprisingly, it has now been shown that similar compounds are excellent anti-inflammatory Have an effect with only low toxicity. These connections have the general formula

Sehwellungsrückgang
in ".. nachEye curl reduction
in accordance 7575 150150 MinutenMinutes 11,411.4 Menge in mg
je KilogrammAmount in mg
per kilogram Verbindunglink Raue inira-Rough inira- 3030th peritonciil-peritonciil- 4,44.4 8989 gespritzlsplash »Novaminsulfon«"Novaminsulfon" 7878 (Vergleichs(Comparative 6464 verbindung) ..link) .. 7979 100100 200200 Verbindung derConnection of 7979 72,872.8 Beispiele 1Examples 1 6565 7575 und 2 and 2 8989 89,289.2 100100 8989 100100 100100 6464 100100 100100 100100 100100 86,486.4 100100 7575 100100

C=C- COO -(CH2),,—N 1C = C-COO - (CH 2 ) ,, - N 1

in der Ri und R2 gleich Wasserstoff oder eine Methoxygruppe, R eine Alkylgruppe mit 2 bis 4 Kohlenstoffatomen ist. R:s und Ri niedrigmolekulare Alkylgruppen sind, die außerdem mit dem Stickstoffatom, an das sie gebunden sind, einen sechsgliedrigen Ring bilden können, und /; die Zahl 2 oder 3 ist.in which Ri and R2 are hydrogen or a methoxy group, R is an alkyl group of 2 to 4 carbon atoms. R: s and Ri low molecular weight alkyl groups which also form a six-membered ring with the nitrogen atom to which they are attached can form, and /; the number is 2 or 3.

Die Erfindung betrifft daher die basisch substituierten Ester trisubstituierter Acrylsäuren der vorstehenden allgemeinen Formel I, deren Hydrochloride und ein Verfahren zur Herstellung dieser basischen Ester der allgemeinen Formel I, in der die Reste R, Ri bis Ri die vorstehende Bedeutung haben, und deren Hydrochloride, das dadurch gekennzeichnet ist, daß man in an sich bekannter Weise die Natriumsalze trisubstituierter Acrylsäuren der allgemeinen FormelThe invention therefore relates to the basic substituted Esters of trisubstituted acrylic acids of the above general formula I, their hydrochlorides and a process for the preparation of these basic esters of the general formula I in which the radicals R, Ri to Ri have the above meaning, and their hydrochloride, which is characterized is that in a known manner the sodium salts of trisubstituted acrylic acids the general formula

R1 - R 1 -

mit basisch substituierten Alkylchloriden der allgemeinen Formelwith basic substituted alkyl chlorides of the general formula

Cl - (CH2),, - NCl - (CH 2 ) ,, - N

in welchen die Reste R, Ri bis Ri und /; die vorstehend angegebene Bedeutung haben, umsetzt und die basisch substituierten Ester aus dem Umselzungsgemisch besonders als Hydrochloride abtrennt.in which the radicals R, Ri to Ri and /; the above Have given meaning, converts and the basic substituted esters from the conversion mixture separates especially as hydrochloride.

Die entzündungshemmende Wirkung dieser Verbindungen wurde nach dem Ratlen-Hinlerpfotcn-Vcrsuch ermittelt. Es wurde mit »Makrodex« (Polyglykose) an der Rattenpfote ein ödem erzeugt und der Sehwellungsrückgang nach der Verabreichung der /u untersuchenden Verbindungen bestimmt. The anti-inflammatory activity of these compounds was determined according to the Ratlen-Hinlerpfotcn study determined. Edema was produced on the rat paw with "Makrodex" (polyglycosis) and the decrease in visual curl after administration of the test compounds.

Verbindungen des Beispiels 1Compounds of Example 1

2-Äthyl-3,3-diphenylacrylsäure-/)-diäthylamino-2-ethyl-3,3-diphenylacrylic acid - /) - diethylamino-

äthylester-hydrochlorid,
Verbindungen des Beispiels 2ethyl ester hydrochloride,
Compounds of example 2

2-Äthyl-3,3-diphenylacrylsäure-,;-dimethylamino-äthylester-hydrochlorid, 2-ethyl-3,3-diphenylacrylic acid -,; - dimethylamino-ethyl ester hydrochloride,

2-Äthyl-3,3-diphenylacryIsäure-;-dimethyl-2-ethyl-3,3-diphenylacryIic acid -; - dimethyl-

amino-propylester-hydrochlorid,
2-Älhyl-3,3-diphenylacrylsäure-/j-piperi-amino propyl ester hydrochloride,
2-ethyl-3,3-diphenylacrylic acid / j-piperi-

dino-(r)-äthylester-hydrochlorid,
30' 2-n-Butyl-3,3-diphenyIacrylsäure-/j'-dimethyI-dino (r) ethyl ester hydrochloride,
30 '2-n-butyl-3,3-diphenyIacrylic acid / j'-dimethyl

amino-äthylester-hydrochlorid,
2-n-Butyl-3,3-diphenylacrylsäure-;-dimethylamino-propylester-hydrochlorid. amino ethyl ester hydrochloride,
2-n-butyl-3,3-diphenylacrylic acid -; - dimethylamino-propyl ester hydrochloride.

Die Herstellung der trisubstituierten Acrylsäuren erfolgt nach Reformatsky durch Umsetzung der entsprechenden Ketone mit den entsprechenden u-Halogensäureestern, Abspaltung von Wasser aus den entstandenen Hydroxycarbonsäuren und Verseifen der Ester zur freien Säure (vergleiche z. B. Houben—We yl. Methoden der organischen Chemie, Bd. 8, 1952, S. 511).The trisubstituted acrylic acids are prepared by conversion according to Reformatsky of the corresponding ketones with the corresponding u-halogen acid esters, elimination of water the resulting hydroxycarboxylic acids and saponification of the esters to form the free acid (compare e.g. Houben — We yl. Methods of organic Chemie, Vol. 8, 1952, p. 511).

Aus den entsprechenden Natriumsalzen der trisubstituierten Acrylsäuren werden in an sich bekannter Weise die beanspruchten neuen basischen Ester und deren Hydrochloride durch Umsetzung mit den entsprechenden basisch substituierten Alkylchloriden erhalten.The corresponding sodium salts of the trisubstituted acrylic acids are known per se Way the claimed new basic esters and their hydrochlorides by reaction obtained with the corresponding basic substituted alkyl chlorides.

Die Verbindungen der Erfindung sind neu, und es sind auch keine ähnlichen Verbindungen mit gleicher Wirkung bekannt. Es wurde lediglich berichtet (Farmaco (Pavia) Ed. sei., Bd. 14, 1959, S. 714 bis 726 [s. Chemical Abstracts, Bd. 54, I960, Spalte 19 967 f- g]), daß die p-Phenylziintsäure der FormelThe compounds of the invention are new, and there are no similar compounds to either known to have the same effect. It was only reported (Farmaco (Pavia) Ed. Sei., Vol. 14, 1959, Pp. 714 to 726 [see p. Chemical Abstracts, Vol. 54, 1960, Column 19 967 f-g]) that p-phenyltiintic acid the formula

■V■ V

CH = CH-COOHCH = CH-COOH

entzündungshemmend wirkt. Diese Wirkung bleibt jedoch durch Veresterung dieser Säure mit basisch substituierten Alkoholen nur teilweise erhalten, während bei den neuen Verbindungen der Erfindung die entzündungshemmende Wirkung erst durch die Veresterung mit Aminoalkoholen auftritt. Die freien Säuren dagegen wirken choleretisch. Aus diesem Grunde ist es neu und überraschend, daß die Verbindungen der Erfindung stark entzündungshemmend wirken.has anti-inflammatory effects. However, this effect remains basic due to the esterification of this acid substituted alcohols only partially obtained, while with the new compounds of the invention the anti-inflammatory effect only occurs through esterification with amino alcohols. The free Acids, on the other hand, have a choleretic effect. Because of this, it is new and surprising that the connections of the invention have strong anti-inflammatory effects.

Beispiel 1example 1

2-Äthyl-3,3-diphenylacrylsäure-/;-diälhylaminoäthylester-hydrochlorid 2-ethyl-3,3-diphenylacrylic acid - /; - diethylaminoethyl ester hydrochloride

20 g 2-Äthyl-3,3-diphenylacrylsäure werden in 300 ml Dioxan gelöst, mit 80 ml 2normaler wäßriger Natronlauge und anschließend mit 13.6 g //-Diäthylamino-äthylchlorid-hydrochlorid versetzt und unter Rühren 8 Stunden unter Rückfluß gekocht. Nach dem Abdestillieren des Lösungsmittels wird der Rückstand mit überschüssiger 20%iger Natronlauge versetzt und mit Chloroform ausgeschüttelt. Die Chloroformschicht wird über Natriumsulfat getrocknet, das Chloroform unter Normaldruck und das nicht umgesetzte /i-Diäthylaminoäthylchlorid im Vakuum abdestilliert. Der ölige Rückstand wird in wasserfreiem Äther gelöst und das 2-Äthyl-3,3-diphenylacrylsäure-p'-diäthylamino-äthylester-hydrochlorid mit Chlorwasserstoffgas ausgefällt. Nach dem Umkristallisieren aus Benzol erhält man 23,0 g des Hydrochlorids als farblose Kristalle mit dem Schmelzpunkt 156 bis 159 C, das sind 68"'O der Theorie.20 g of 2-ethyl-3,3-diphenylacrylic acid are dissolved in 300 ml of dioxane, with 80 ml of 2 normal aqueous Sodium hydroxide solution and then with 13.6 g // - diethylamino-ethyl chloride hydrochloride added and refluxed with stirring for 8 hours. After the solvent has been distilled off, the Excess 20% sodium hydroxide solution is added to the residue and the mixture is extracted by shaking with chloroform. the The chloroform layer is dried over sodium sulfate, the chloroform under normal pressure and the unreacted / i-diethylaminoethyl chloride distilled off in vacuo. The oily residue is dissolved in anhydrous ether and the 2-ethyl-3,3-diphenylacrylic acid-p'-diethylamino-ethyl ester hydrochloride precipitated with hydrogen chloride gas. After recrystallization from benzene, 23.0 g are obtained of the hydrochloride as colorless crystals with a melting point of 156 to 159 C, that is 68 "O der Theory.

Beispiel 2Example 2

Nach der gleichen Arbeitsweise wie im Beispiel 1 erhält man folgende Verbindungen:Following the same procedure as in Example 1, the following compounds are obtained:

2-Äthyl-3,3-diphenylacrylsäure-/)'-dimethylamino-äthylester-hydrochlorid, 2-ethyl-3,3-diphenylacrylic acid - /) '- dimethylamino-ethyl ester hydrochloride,

F. = 107 bis 113 C,F. = 107 to 113 C,

2-Äthyl-3,3-diphenylacrylsäure-;'-dimethylamino-propylester-hydiOchlorid, 2-ethyl-3,3-diphenylacrylic acid -; '- dimethylamino-propylester-hydrochloride,

F. = 145 bis 148 C,
2-Äthyl-3,3-diphenyIacrylsäiire-/)-piperidino-( 1 'Hithylester-hydrochlorid,F. = 145 to 148 C,
2-ethyl-3,3-diphenyIacrylic acid - /) - piperidino- (1 'ethyl ester hydrochloride,

F. = 147 bis 149 C,
2-n-Butyl-3,3-diphenylacrylsäiire-/i'-dimethylamino-älhylester-hydrochlorid, F. = 147 to 149 C,
2-n-butyl-3,3-diphenylacrylic acid / i'-dimethylamino-ethyl ester hydrochloride,

F. = 92 bis 94 C,
2-n-Bιltyl-3,3-diphenylacl·ylsäure-/^diäthylamino-äthylester-hydrochlorid, F. = 92 to 94 C,
2-n-Bιltyl-3,3-diphenylaclylic acid - / ^ diethylamino-ethyl ester hydrochloride,

F. = 136 bis 137 C,
2-n-Butyl-3,3-diphenylacrylsäure-;-dimethylamino-propylester-hydrochlorid, F. = 136 to 137 C,
2-n-butyl-3,3-diphenylacrylic acid -; - dimethylamino-propyl ester hydrochloride,

F. = 53 bis 60 C,F. = 53 to 60 C,

2-n-Butyl-3,3-diphenylacrylsäure-/v'-piperidino-( 1 ')-äthylester-hydrochlorid,2-n-butyl-3,3-diphenylacrylic acid / v'-piperidino (1 ') ethyl ester hydrochloride,

F. = 122 bis 126 C,
2-Äthyl-3,3-bis-(p,p'-dimethoxyphenyl)-acrylsäure-p'-dimethylamino-äthylester- hydrochlorid,F. = 122 to 126 C,
2-ethyl-3,3-bis- (p, p'-dimethoxyphenyl) -acrylic acid-p'-dimethylamino-ethyl ester hydrochloride,

F. = 164 bis 166 C.F. = 164 to 166 C.

Claims (2)

Patentansprüche:Patent claims: 1. Basisch substituierte Ester von trisubstituierten Acrylsäuren der allgemeinen Formel1. Basically substituted esters of trisubstituted acrylic acids of the general formula C=C- COO—(CH2),,- N
RC = C-COO- (CH 2 ) "- N
R. in der R, und R1. Wasserstoff oder eine Methoxygruppe, R eine Alkylgruppe mit 2 bis 4 Kohlenstoffatomen ist, R:s und Ri niedrigmolekulare Alkylgruppen, die mit dem Stickstoffatom, an das sie gebunden sind, einen sechsgliedrigen Ring bilden können, und /; die Zahl 2 oder 3 ist, und deren Hydrochloride.in the R, and R 1 . Hydrogen or a methoxy group, R is an alkyl group with 2 to 4 carbon atoms, R: s and Ri are low molecular weight alkyl groups which can form a six-membered ring with the nitrogen atom to which they are attached, and /; the number is 2 or 3, and their hydrochlorides. 2. Verfahren zur Herstellung der antiphlogistisch wirkenden, basisch substituierten Ester von trisubstituierten Acrylsäuren der allgemeinen Formel nach Anspruch 1, in der die Reste R, Ri bis Ri und /; die vorstehend angegebene Bedeutung haben, und deren Hydrochloriden, dadurch gekennzeichnet, daß man in an sich bekannter Weise die Natriumsalze trisubstituierter Acrylsäuren der allgemeinen Formel2. Process for the preparation of the anti-inflammatory, basic substituted esters of trisubstituted acrylic acids of the general formula according to Claim 1, in which the radicals R, Ri to Ri and /; the meaning given above have, and their hydrochlorides, characterized in that the sodium salts are trisubstituted in a manner known per se Acrylic acids of the general formula C = C-COONa
RC = C-COONa
R. mit basisch substituierten Alkylchloriden der allgemeinen Formelwith basic substituted alkyl chlorides of the general formula Cl-(CH2),-NCl- (CH 2 ), -N in welchen die Reste R, Ri bis Ri und η die vorstehend angegebene Bedeutung haben, umsetzt und die basisch substituierten Ester aus dem Umsetzungsgemisch, besonders als Hydrochloride, abtrennt.in which the radicals R, Ri to Ri and η have the meaning given above, is reacted and the basic substituted esters are separated from the reaction mixture, especially as hydrochlorides.
DEG46252A 1966-03-08 1966-03-08 Basically substituted esters of trisubstituted acrylic acids, their hydrochlorides and processes for their preparation Pending DE1292652B (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DEG46252A DE1292652B (en) 1966-03-08 1966-03-08 Basically substituted esters of trisubstituted acrylic acids, their hydrochlorides and processes for their preparation
AT177867A AT271454B (en) 1966-03-08 1967-02-23 Process for the preparation of new basic esters of α, β-disubstituted cinnamic acids and their salts
ES337592A ES337592A1 (en) 1966-03-08 1967-03-04 Novel acrylic acid derivatives and process for the preparation thereof
NL6703540A NL6703540A (en) 1966-03-08 1967-03-06
BE695052D BE695052A (en) 1966-03-08 1967-03-06
CH329167A CH478090A (en) 1966-03-08 1967-03-07 Process for the preparation of esters of trisubstituted acrylic acid
FR69048367A FR1536213A (en) 1966-03-08 1967-03-07 Process for the preparation of basic substituted esters of trisubstituted acrylic acids
DK116867A DK114548B (en) 1966-03-08 1967-03-07 Process for the preparation of antiphlogistic salts of basic substituted esters of trisubstituted acrylic acids.
GB1075667A GB1139994A (en) 1966-03-08 1967-03-07 Novel acrylic acid derivatives and process for the preparation thereof
SE317367A SE315881B (en) 1966-03-08 1967-03-08

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEG46252A DE1292652B (en) 1966-03-08 1966-03-08 Basically substituted esters of trisubstituted acrylic acids, their hydrochlorides and processes for their preparation

Publications (1)

Publication Number Publication Date
DE1292652B true DE1292652B (en) 1969-04-17

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ID=7127975

Family Applications (1)

Application Number Title Priority Date Filing Date
DEG46252A Pending DE1292652B (en) 1966-03-08 1966-03-08 Basically substituted esters of trisubstituted acrylic acids, their hydrochlorides and processes for their preparation

Country Status (10)

Country Link
AT (1) AT271454B (en)
BE (1) BE695052A (en)
CH (1) CH478090A (en)
DE (1) DE1292652B (en)
DK (1) DK114548B (en)
ES (1) ES337592A1 (en)
FR (1) FR1536213A (en)
GB (1) GB1139994A (en)
NL (1) NL6703540A (en)
SE (1) SE315881B (en)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
SE315881B (en) 1969-10-13
CH478090A (en) 1969-09-15
GB1139994A (en) 1969-01-15
NL6703540A (en) 1967-09-11
AT271454B (en) 1969-06-10
DK114548B (en) 1969-07-14
BE695052A (en) 1967-08-14
ES337592A1 (en) 1968-03-01
FR1536213A (en) 1968-08-16

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