CS239449B1 - The solution is in the field of synthetic drugs. The subject of the invention is heterocyclic syringic amides and their O-substitution derivatives of the formula I wherein R is benzyl, hydrogen or 2-dimethylaminoethyl and X is a direct bond, the methylene CH, as well as their salts with pharmaceutically acceptable inorganic or organic acids with respect to basic substances. The compounds of formula (I) and their salts are characterized by practically useful arterial, hypotensive and adrenolytic activity. They are useful as drugs for epilepsy and high blood pressure. - Google Patents
The solution is in the field of synthetic drugs. The subject of the invention is heterocyclic syringic amides and their O-substitution derivatives of the formula I wherein R is benzyl, hydrogen or 2-dimethylaminoethyl and X is a direct bond, the methylene CH, as well as their salts with pharmaceutically acceptable inorganic or organic acids with respect to basic substances. The compounds of formula (I) and their salts are characterized by practically useful arterial, hypotensive and adrenolytic activity. They are useful as drugs for epilepsy and high blood pressure. Download PDFInfo
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Abstract
Vynález spadá do oboru syntetických lieSiv. Jeho predmetom je spĎsob pripravy diesterov 4-aryl-2,6-dimetyl-1,4-dihydropyridín-3,5-dikarboxylovej kyseliny vzorca I v ktorom R představuje priamy algbo rozvětvený alkylový zvyšok s počtom atomov uhlíka 1 až 5, pričom alkylový zvyšok m6že byť přerušený v reťazci atomom kyslíka a X představuje nitroskupinu v o-, m- alebo g-polohe. Tieto zlúčeniny majú antianginozny a antihypertenzný účinok. Příprava sa uskutočňuje reakciou esterov acetoctovej kyseliny, nitrobenzaldehyddiacetátu a amonných solí alifatických monokarboxylových kyselin.The invention belongs to the field of synthetic drugs. Its subject is a method of preparing diesters of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid of formula I in which R represents a straight or branched alkyl radical with a number of carbon atoms from 1 to 5, the alkyl radical may be interrupted in the chain by an oxygen atom and X represents a nitro group in the o-, m- or g-position. These compounds have antianginal and antihypertensive effects. The preparation is carried out by the reaction of acetoacetic acid esters, nitrobenzaldehyde diacetate and ammonium salts of aliphatic monocarboxylic acids.
Description
Vynález sa týká spflsobu přípravy diesterov 4-aryl-2,6-dimetyl-1,4-dihydropyridín-3,5-dikarboxylovej kyseliny všeobecného vzorca IThe present invention relates to a process for the preparation of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diesters of the general formula I
(I) v ktorom R představuje prlamy alebo rozvětvený alkylový zvyšok s počtom atómov uhlíka 1 až 5, pričom alkylový zvyšok mflže byť přerušený v reťazci atómom kyslíka a X představuje nltroskupinu v o-, m- alebo p-polohe. Tieto zlúčeniny sa používajú ako antianginózne látky a antihypertenzíva.(I) wherein R represents a straight or branched alkyl radical having a carbon number of 1 to 5, wherein the alkyl radical may be interrupted in the chain by an oxygen atom and X represents an n-trio at the o-, m- or β-position. These compounds are used as antianginal agents and antihypertensives.
Doposial* sa tieto zlúčeniny připravovali reakciou nitrobenzaldehydov s estermi acetoctovej kyseliny a amoniakem v inertnom rozpúšťadle (F. Bossert, W. Vater: US. pat.To date, these compounds have been prepared by reacting nitrobenzaldehydes with acetic acid esters and ammonia in an inert solvent (F. Bossert, W. Vater: US Pat.
3644627 (1972), Qer. pat. 1670827 (1967), S. Afričan pat. 6801482 (1982), Brit. pat. 1173104 (1968)).3644627 (1972), Qer. pat. 1670827 (1967), S. African Pat. 6801482 (1982), Brit. pat. 1173104 (1968)).
Ďalšou metodou přípravy zlúčenín všeobecného vzorce I je reakcia nitrobenzaldehyddiacetátu s metylesterom acetoctovej kyseliny a amoniakom za přítomnosti organických zásad, napr. pyridinu v inertnom rozpúšťadle (Lek. Ljubljana: Holand, zvěr. prihl,Another method for preparing compounds of formula I is by reacting nitrobenzaldehyde diacetate with acetic acid methyl ester and ammonia in the presence of organic bases, e.g. pyridine in an inert solvent (Lek. Ljubljana: Netherland, Animal,
6203260 (196-1).6203260 (196-1).
Ďalšou známou metodou přípravy zlúčenín všeobecného vzorca I je reakcia nitrobenzaldehydu s estermi aminokrotonovej kyseliny (Murakami M. a spol.: Japan Kokai Tokkyo Koho 8002652 (1980)).Another known method for preparing compounds of formula I is by reacting nitrobenzaldehyde with aminocrotonic acid esters (Murakami M. et al., Japan Kokai Tokkyo Koho 8002652 (1980)).
Ďalšou popísanou metodou prlpravy zlúčenín všeobecného vzorca I je reakcia nitrobenzaldehydu s esterom acetoctovej kyseliny a esterom aminokrotonovej kyseliny (Murakami M. a spol.: Japan Kokai Tokkyo Koho 8004318 (1980)).Another method described for the preparation of compounds of formula I is the reaction of nitrobenzaldehyde with acetic acid ester and aminocrotonic acid ester (Murakami M. et al., Japan Kokai Tokkyo Koho 8004318 (1980)).
Podstatou vynálezu je spflsob přípravy zlúčenín všeobecného vzorca I z 2 až 3 molových dielov esteru acetoctovej kyseliny všeobecného vzorca II ch3-co-ch2-coor (II) v ktorom má R ten istý význam ako vo vzorci I, z 1 molového dielu benzaldehyddiacetátu všeobecného vzorca IIISUMMARY OF THE INVENTION The present invention provides a process for the preparation of compounds of formula I from 2 to 3 molar parts of acetic acid ester of formula II ch 3 -co-ch 2 -coor (II) in which R has the same meaning as in formula I of formula III
OCOCH3 ococh3 (III) v ktorom mé X ten istý význam ako vo vzorci I a z 1 až 1,5 molového dielu amonnej soli alifatickej monokarboxylovej kyseliny s počtom atómov uhlíka 2 až 5 v prostředí inertného organického rozpúšťadla, napr. chloroformu, dioxanu, dimetylformamidu, dimetylsulfoxidu, kyseliny octovej, alifatických alkoholov s počtom átómov uhlíka 1 až 3 alebo v zmesi uvedených rozpúšťadel pri teplote 20 až 150 °C.OCOCH 3 ococh 3 (III) wherein X has the same meaning as in formula I and from 1 to 1.5 molar parts of an ammonium salt of an aliphatic monocarboxylic acid having a carbon number of 2 to 5 in an inert organic solvent, e.g. chloroform, dioxane, dimethylformamide, dimethylsulfoxide, acetic acid, aliphatic alcohols having a carbon number of 1 to 3, or in a mixture of the said solvents at a temperature of 20 to 150 ° C.
Ako estery acetoctovej kyseliny všeobecného vzorca IX možno použiť metylester, etylester izopropylester, metoxyetylester, etoxyetylester, propoxyetylester a ood. Ako substituované benzaldehyddiacetáty možno použiť ο-nitro-, m-nitro-, resp. p-nitro-benzaldehyddiacetát. Ako amonné soli karboxylových kyselin možno použiť propionan amonný, máselňan amonný, valeran amonný, s výhodou octan amonný.As acetic acid esters of formula (IX), methyl ester, ethyl isopropyl ester, methoxyethyl ester, ethoxyethyl ester, propoxyethyl ester and ood may be used. As substituted benzaldehyde diacetates, ο-nitro-, m-nitro-, resp. p-nitro-benzaldehyddiacetát. Ammonium salts of carboxylic acids which can be used are ammonium propionate, ammonium butyrate, ammonium valerate, preferably ammonium acetate.
Postup podl’a vynálezu sa uskutočňuje tak, že sa ester acetoctovej kyseliny všeobecného vzorca II zahrieva so substituovaným aldehyddiacetátom všeobecného vzorca III s niektorou z uvedených amonných soli v prostředí vyššie uvedených inertných organických rozpúšťadiel na vtyššie uvedená teplotu za tlaku 0,1 až 2,5 MPa.The process according to the invention is carried out by heating an acetic acid ester of the formula II with a substituted aldehyde diacetate of the formula III with one of the ammonium salts mentioned above in an environment of the above-mentioned inert organic solvents to the above temperature at a pressure of 0.1 to 2.5. bar.
Reakcia sa uskutočňuje výhodné pri teplote spatného toku použitého rozpúšťadla alebo zmesi rozpúšťadiel za normálneho tlaku. Z ddvodov malej rozpustnosti produktov reakcie všeobecného vzorca I v metanole je výhodné reakciu prevádzať při teplote spatného toku v tomto rozpúšťadle. Amonnú sol’ potřebná do reakcie možno připravit aj in šitu z príslušnej alifatickej kyseliny.The reaction is preferably carried out at the reflux temperature of the solvent or solvent mixture used under normal pressure. Because of the low solubility of the reaction products of formula (I) in methanol, it is preferable to carry out the reaction at reflux temperature in this solvent. The ammonium salt required for the reaction may also be prepared in situ from the appropriate aliphatic acid.
Reakčná doba je závislá na reakčnej teplote a na použitom estere acetoctovej kyseliny všeobecného vzorca II. Pri teplote spatného toku použitého rozpúšťadla alebo zmesi rozpúšťadiel je reakčná doba 4 až 10 hod. Izolácia zlúčenln všeobecného vzorca I sa uskutoční odfiltrováním alebo odstředěním vykrystalizovaného produktu po vychladnutí reakčnej zmesi. Surově produkty sa čistia prekryštálizováním z vhodného rozpúšťadla.The reaction time is dependent on the reaction temperature and the acetic acid ester II used. At the reflux temperature of the solvent or solvent mixture used, the reaction time is 4 to 10 hours. The isolation of the compounds of formula I is effected by filtering or centrifuging the crystallized product after cooling the reaction mixture. The crude products are purified by recrystallization from a suitable solvent.
Výhodou postupu podl’a vynálezu oproti váčšine doposial’ popísaných postupov je použitie podstatné lacnejšieho o-, resp. p-nitrobenzaldehyddiacetátu namiesto o-, resp. p-nitrobenzaldehydu a mierne zvýšené výťažky oproti postupu založenom na reakcii metylesteru acetoctovej kyseliny, nitrobenzaldehyddiacetétu a amoniaku, resp. za přítomnosti pyridinu.The advantage of the process according to the invention over most of the processes described so far is the use of a substantially cheaper o- and resp. of p-nitrobenzaldehyde diacetate instead of o- and resp. p-nitrobenzaldehyde and slightly increased yields compared to the procedure based on the reaction of methyl acetate, nitrobenzaldehyde diacetate and ammonia, respectively. in the presence of pyridine.
V ňalšom je predmet vynálezu objasněný na príkladoch bez toho, že by sa na tieto výlučné obmedzoval.In the following, the invention is illustrated by way of example without being limited thereto.
Příklad 1Example 1
Dimetylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej2,6-Dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
7,54 g 2-nitrobenzaldehyddiacetátu sa spolu s 8 ml metylesteru kyseliny acetoctovej a 3,45 g octanu amonného zahrieva v 10 ml metanolu 7 hodin pri teplote varu. Po ochladení a odfiltrovaní sa surový produkt prekryštalizuje z kyseliny octovej. Získajú sa jasnožlté kryštály (6,7 g) s teplotou topenia ,72 až 174 °C v 65 °h výtažku.7.54 g of 2-nitrobenzaldehyde diacetate, together with 8 ml of methyl acetic acid ester and 3.45 g of ammonium acetate, are heated in 10 ml of methanol for 7 hours at the boiling point. After cooling and filtering, the crude product is recrystallized from acetic acid. Bright yellow crystals (6.7 g) with a melting point of 72-174 ° C in a 65 ° h yield are obtained.
Rovnakým spdsobom za použitia příslušných východzích látok ga získajú tieto zlúčeniny:In the same manner, using the appropriate starting materials g, the following compounds are obtained:
a) dimetylester kyseliny 2,6-dimetyl-4-(3-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 206 až 208 °Ca) 2,6-dimethyl-4- (3-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, m.p. 206-208 ° C
b) dimetylester kyseliny 2,5-dimetyl-4-(4'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 196 až ,97 °Cb) 2,5-dimethyl-4- (4'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, m.p. 196-97 ° C
c) dietylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 122 až 124 °Cc) 2,6-dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester, m.p. 122-124 ° C
d) dietylester kyseliny 2,6-dimetyl-4-(3'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 160 až 161 °Cd) 2,6-dimethyl-4- (3'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester, m.p. 160-161 ° C
e) dietylester kyseliny 2,6-dimetyl-4-(4’-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 132 až 134 °C(e) 2,6-dimethyl-4- (4´-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester, m.p. 132-134 ° C
f) diizopropylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 140 až 142 °Cf) 2,6-dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid diisopropyl ester, m.p. 140-142 ° C
g) diizopropylester kyseliny 3,6-dimetyl-4-(3'-nitrofenyl)-,,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 123 °Cg) 3,6-dimethyl-4- (3'-nitrophenyl) -4,4-dihydropyridine-3,5-dicarboxylic acid diisopropyl ester, m.p. 123 ° C
h) diizopropylester kyseliny 2,6-dimetyl-4-(4’-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 151 až 152 °C(h) 2,6-dimethyl-4- (4'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid diisopropyl ester, m.p. 151-152 ° C
i) bis-metoxyetylester kyseliny 2,6-dimetyl-4-(4*-nitrofenyI)-1,4-dihydropyridín-3,5-dikarboxýlovej s teplotou topenia 108 až 112 °C(i) 2,6-dimethyl-4- (4'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid bis-methoxyethyl ester, m.p. 108-112 ° C
j) bis-etoxyetylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridin-3,5-dikarboxylovéj s teplotou topenia 93 až 96 °Cj) 2,6-dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid bis-ethoxyethyl ester, m.p. 93-96 ° C
k) bis-etoxyetylester kyseliny 2,6-dimetyl-4-(3*-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 101 až 104 °Ck) 2,6-dimethyl-4- (3'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid bis-ethoxyethyl ester, m.p. 101-104 ° C
l) bis-propoxyetylester kyseliny 2,6-dimetyl-4-(3*-nítrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej s teplotou topenia 83 až 86 °C.l) 2,6-dimethyl-4- (3'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid bis-propoxyethyl ester, m.p. 83-86 ° C.
Příklad 2Example 2
Dimetylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovéj2,6-Dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
7,54 g 2-nitrobenzaldehyddiacetátu sa spolu s 8 ml metylesteru kyseliny aeetoctovej a 1,45 g uhličitanu amónneho zahrieva v zmesi s 10 ml metanolu a kys. octovej (99 %-nej) hodin pri teplote varu. Po ochladení a odfiltrovaní sa surový produkt prekryštálizuje z 1’adovej kys. octovej. Získajú sa jasnožlté kryštály (6,8 g t.j. 66 %) s teplotou topenia 171 až 173 °C. Rovnakým spfisobom za použitia příslušných výehodzích látok sa získajú zlúčeniny uvedené v příklade 1a až 1.7.54 g of 2-nitrobenzaldehyde diacetate, together with 8 ml of methyl acetate and 1.45 g of ammonium carbonate, are heated in a mixture with 10 ml of methanol and acid. acetic (99%) hours at boiling point. After cooling and filtering, the crude product is recrystallized from 1'adic acid. acid. Clear yellow crystals (6.8 g, i.e. 66%), m.p. 171-173 ° C, are obtained. In the same manner, using the appropriate preferences, the compounds of Examples 1a to 1 are obtained.
Příklad 3Example 3
Dimetylester kyseliny 2,6-dimetyl-4-(2'-nitrofenylí-1,4-dihydropyridín-3,5-dikarboxylovej g 2-nitrobenzaldehyddiacetátu sa spolu s 3,2 ml acetoctanu metylového a 1,5 g octanu amónneho zahrieva v 4 ml dioxanu 3 hodiny pri teplote varu. Po ochladení a od- , filtrovaní sa surový produkt prekryštalizuje z l’adovej kyseliny octovej. Získajú ga'žité kryštály s teplotou 171 až 173 °C v 36 % výtažku. Rovnakým spfisobom sa získajú zlúčeniny uvedené v příklade 1a až 1.2,6-Dimethyl-4- (2'-nitrophenyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester) is heated together with 3.2 ml of methyl acetate and 1.5 g of ammonium acetate in 4 ml of 2-nitrobenzaldehyde diacetate. After cooling and filtering, the crude product is recrystallized from glacial acetic acid to give pale crystals at a temperature of 171-173 ° C in a 36% yield. Examples 1a to 1.
Přikládáattaches
Dimetylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej '2,6-Dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
7,54 g 2-nitrobenzaldehyddiacetátu sa spolu s 8 ml metylesteru kyseliny aeetoctovej a 3,55 g valeranu amónneho zahrieva v 8 ml 2-propanón 4 hodiny pri teplote varu. Reakčná zmes sa spraouje analogicky ako v příklade 1. Získajú sa žité kryštály s teplotou topenia 172 až 174 °C v 64 % výtažku.7.54 g of 2-nitrobenzaldehyde diacetate, together with 8 ml of methyl acetic acid ester and 3.55 g of ammonium valerate, are heated in 8 ml of 2-propanone at reflux for 4 hours. The reaction mixture is sprayed in analogy to Example 1. Obtained rye crystals with a melting point of 172-174 ° C in 64% yield.
Príkla.d5Príkla.d5
Dimetylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej2,6-Dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5 - dicarboxylic acid dimethyl ester
3,45 g octanu amónneho zahrieva v 6 ml chloroformu 3 hodiny pri teplote varu. Reakčná zmes sa spraouje analogicky ako v příklade 1. Získajú sa svetložlté kryštály s teplotou topenia 171 až 174 °C v 48 % výtažku.3.45 g of ammonium acetate are heated at reflux temperature in 6 ml of chloroform for 3 hours. The reaction mixture was sprayed analogously to Example 1. Obtained light yellow crystals, m.p. 171-174 ° C in 48% yield.
Příklad 6Example 6
Dimetylester kyseliny 2,6-dimetyl-4-(2'-nitrofenyl)-1,4-dihydropyridín-3,5-dikarboxylovej2,6-Dimethyl-4- (2'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
3,45 g octanu amonného zahrieva v 8 ml N,N-dimetylformamidu 2 hodiny pri teplote varu. Po ochladení a 3-dňovom stát! vypadnú kryštály, ktoré sa spracujú analogicky ako v příklade3.45 g of ammonium acetate are heated at boiling point in 8 ml of N, N-dimethylformamide for 2 hours. After cooling and stand for 3 days! crystals are precipitated which are treated analogously to the example
1. Získajú sa žité kryštály s teplotou topenia 172 až 174 °C v 45 % výtažku.1. Obtained crystals having a melting point of 172-174 ° C in 45% yield.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846635A CS239449B1 (en) | 1984-09-04 | 1984-09-04 | The solution is in the field of synthetic drugs. The subject of the invention is heterocyclic syringic amides and their O-substitution derivatives of the formula I wherein R is benzyl, hydrogen or 2-dimethylaminoethyl and X is a direct bond, the methylene CH, as well as their salts with pharmaceutically acceptable inorganic or organic acids with respect to basic substances. The compounds of formula (I) and their salts are characterized by practically useful arterial, hypotensive and adrenolytic activity. They are useful as drugs for epilepsy and high blood pressure. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846635A CS239449B1 (en) | 1984-09-04 | 1984-09-04 | The solution is in the field of synthetic drugs. The subject of the invention is heterocyclic syringic amides and their O-substitution derivatives of the formula I wherein R is benzyl, hydrogen or 2-dimethylaminoethyl and X is a direct bond, the methylene CH, as well as their salts with pharmaceutically acceptable inorganic or organic acids with respect to basic substances. The compounds of formula (I) and their salts are characterized by practically useful arterial, hypotensive and adrenolytic activity. They are useful as drugs for epilepsy and high blood pressure. |
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| Publication Number | Publication Date |
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| CS663584A1 CS663584A1 (en) | 1985-06-13 |
| CS239449B1 true CS239449B1 (en) | 1986-01-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS846635A CS239449B1 (en) | 1984-09-04 | 1984-09-04 | The solution is in the field of synthetic drugs. The subject of the invention is heterocyclic syringic amides and their O-substitution derivatives of the formula I wherein R is benzyl, hydrogen or 2-dimethylaminoethyl and X is a direct bond, the methylene CH, as well as their salts with pharmaceutically acceptable inorganic or organic acids with respect to basic substances. The compounds of formula (I) and their salts are characterized by practically useful arterial, hypotensive and adrenolytic activity. They are useful as drugs for epilepsy and high blood pressure. |
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