SK278217B6 - 3£4-(2-methoxyphenyl)-1-piperazinyl|-2-hydroxy-1-propylesters of alkoxyphenyl-carbame acids and method of preparation thereof - Google Patents
3£4-(2-methoxyphenyl)-1-piperazinyl|-2-hydroxy-1-propylesters of alkoxyphenyl-carbame acids and method of preparation thereof Download PDFInfo
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Abstract
Description
Oblasť technikyTechnical field
Vynález sa týka 3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hy droxy-1 -propy lesterov alkoxyfenylkarbámových kyselín a spôsobu ich prípravy.The invention relates to 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl esters of alkoxyphenylcarbamic acids and a process for their preparation.
Doterajší stav technikyBACKGROUND OF THE INVENTION
Doteraz boli známe 3-alkylamino-2-hydroxy-l-propylestery kyseliny alkoxyfenylkarbámovej, kde alkoxyl znamená substituent v polohe 2-, 3- a 4- aromatického jadra s počtom atómov uhlíka 3 až 7, a alkyl v bázickej časti je jednoduchý nerozvctvený, resp. rozvetvený alkyl s 2 až 4 atómami uhlíka. Uvedené zlúčeniny prejavili lokálne anestetickú a antidisrytmickú aktivitu (Csollei J., Beneš L., Búčiová Ľ., Račanská E., Švec P., Tumová I.: CS 276 205, Račanská E., Csollei J., Búčiová Ľ.: Čcskoslov Farm - v tlači).To date, 3-alkylamino-2-hydroxy-1-propyl esters of alkoxyphenylcarbamic acid have been known in which alkoxyl represents a substituent in the 2-, 3- and 4-position of the aromatic nucleus having carbon numbers of 3 to 7, and respectively. branched alkyl of 2 to 4 carbon atoms. The compounds exhibited local anesthetic and antidisrhythmic activity (Csollei J., Benes L., Bucciova L., Racanska E., Svec P., Tumova I .: CS 276 205, Racanska E., Csollei J., Bucciova L.: Cskoslov Farm - in print).
Podstata vynálezuSUMMARY OF THE INVENTION
Podstatou vynález sú nové doteraz neznáme zlúčeniny všeobecného vzorca ISUMMARY OF THE INVENTION The present invention provides novel compounds of the formula I which are not yet known
kde R znamená alkoxyl s 1 až 3 atómami uhlíka v polohe 2-, 3- a 4- aromatického jadra, ako aj ich soli s organickými alebo anorganickými kyselinami.wherein R is C 1 -C 3 alkoxy in the 2-, 3- and 4-position of the aromatic ring, and salts thereof with organic or inorganic acids.
Uvedené zlúčeniny všeobecného vzorca I je možné podľa vynálezu pripraviť rôznymi spôsobmi, napr. tak, že sa nechá reagovať v polárnom rozpúšťadle: a) 3-bróm-2-hydroxy-l-propylester kyseliny alkoxyfenylkarbámovej všeobecného vzorca IIThe compounds of formula I can be prepared according to the invention in various ways, e.g. by reacting in a polar solvent: (a) the alkoxyphenylcarbamic acid 3-bromo-2-hydroxy-1-propyl ester of formula II
v ktorom R znamená to isté ako vo vzorci I, s l-(2-metoxyfenyljpiperazínom výhodne v prostredí vody pri teplote miestnosti počas 24 hodín.wherein R is the same as in formula I, with 1- (2-methoxyphenyl) piperazine preferably in a water environment at room temperature for 24 hours.
b) 2,3-epoxy-l-propylester kyseliny alkoxyfenylkarbámovej všeobecného vzorca IIIb) 2,3-epoxy-1-propyl ester of alkoxyphenylcarbamic acid of general formula III
NH-CO-O-CHg-CH-ýH^ (III), v ktorom R znamená to isté ako vo vzorci I s l-(2-metoxyfenyljpiperazínom výhodne v prostredí alkanolu s 1 až 4 atómami uhlíka, výhodne etanolu pri teplote varu reakčnej zmesi počas 8 hodín.NH-CO-O-CH 2 -CH 2 -CH 2 (III), wherein R is the same as in formula I with 1- (2-methoxyphenyl) piperazine, preferably in a C 1 -C 4 alkanol, preferably ethanol at the boiling point of the reaction mixture for 8 hours.
Po skončení reakcie sa z reakčného produktu najčastejšie oddestiluje rozpúšťadlo a surový produkt sa rozpustí v zriedenej kyseline chlorovodíkovej, pretrepe éterom. Báza uvoľnená alkalizáciou z vodnej fázy sa vytrepe do éteru. Z éterického roztoku je možné bázický ester previesť priamo na žiadanú soľ a tú ďalej kryštalizovať z organického rozpúšťadla alebo zo zmesi organických rozpúšťadiel. Zo solí s anorganickými kyselinami, vhodnými pre aplikačné formy, prichádzajú do úvahy napr. hydrobromid, hydrochlorid, prípadne zo solí s organickými kyselinami napr. šťavelan, fumarát, citrát a pod.After completion of the reaction, the solvent is most often distilled off from the reaction product and the crude product is dissolved in dilute hydrochloric acid, shaken with ether. The base released by alkalization from the aqueous phase is shaken into ether. From the ether solution, the basic ester can be converted directly to the desired salt and further crystallized from an organic solvent or a mixture of organic solvents. Suitable salts of the inorganic acids suitable for the use forms are e.g. hydrobromide, hydrochloride, optionally from salts with organic acids e.g. oxalate, fumarate, citrate and the like.
Východiskovými surovinami sú bežné chemikálie, ako napr. 2-, 3- a 4- aminofenoly, 2,3-epoxy-l-propanol alebo látky opísané v literatúre. Sú to napr. alkoxyfenylizokyanáty a anilíny opísané v literatúre (Čižmárik J., Borovanský A., Švec P.: Acta Facult Pharm Univ Comeniane 29, 53 (1976)). Nasledujúce príklady bližšie osvetľujú, ale nijako neobmedzujú prípravu a vlastnosti zlúčenín podľa vynálezu.The starting materials are common chemicals such as e.g. 2-, 3- and 4-aminophenols, 2,3-epoxy-1-propanol, or substances described in the literature. They are eg. alkoxyphenylisocyanates and anilines described in the literature (Čižmárik J., Borovanský A., Svec P .: Acta Facult Pharm Univ Comeniane 29, 53 (1976)). The following examples illustrate but do not limit the preparation and properties of the compounds of the invention.
Príklady uskutočnenia vynálezuDETAILED DESCRIPTION OF THE INVENTION
Príklad 1Example 1
Príprava 3-[4-(2-metoxyfeny 1)-1 -piperazinyl]-2-hydroxy- 1 -propy lesteru kyseliny 3-etoxyfenylkarbámovej.Preparation of 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 3-ethoxyphenylcarbamic acid ester.
K 11,5 g (0,06 mol) l-(2-metoxyfenyl)piperazínu v 15 cm3 vody sa za stáleho miešania postupne pridá 9,5 g (0,03 mol) 3-bróm-2-hydroxy-l-propylesteru kyseliny 3-etoxyfenylkarbámovej a mieša sa pri teplote miestnosti počas 24 hodín. Získaný surový produkt sa trikrát extrahuje do 30 cm3 éteru a vysuší bezvodým uhličitanom draselným. Pridaním éterického roztoku suchého chlorovodíka k filtrátu sa vylúči biela kryštalická látka, ktorá sa prečisti kryštalizáciou z 2-propanolu. Získa sa tuhý produkt vo výťažku 75 % teórie. Bezfarebné kryštáliky, 1.1. 110 až 115°C.To 11.5 g (0.06 mol) of 1- (2-methoxyphenyl) piperazine in 15 cm @ 3 of water was gradually added, with stirring, 9.5 g (0.03 mol) of 3-bromo-2-hydroxy-1- of 3-ethoxyphenylcarbamic acid propyl ester and stirred at room temperature for 24 hours. The crude product obtained is extracted three times with 30 cm @ 3 of ether and dried over anhydrous potassium carbonate. Addition of ethereal dry hydrogen chloride to the filtrate gave a white crystalline solid which was purified by crystallization from 2-propanol. A solid product is obtained in a yield of 75% of theory. Colorless crystals, 1.1. Mp 110-115 ° C.
Príklad 2Example 2
Príprava 3-[4-(2-metoxyfenyl)-1 -piperazinyl]-2-hydroxy- 1-propylesteru kyseliny 4-metoxyfenylkarbámovej.Preparation of 4-methoxyphenylcarbamic acid 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl ester.
K reakčnej zmesi 2,2 g (0,01 mol) 2,3-epoxy-l-propylesteru kyseliny 4-metoxyfenylkarbámovej v 30 cm3 etanolu sa pridá 1,9 g (0,01 mol) l-(2-metoxyfenyl)piperazínu a zahrieva sa pri teplote varu reakčnej zmesi počas 8 hodín. Etanol sa oddestiluje za mierneho vákua, surový produkt sa rozpustí v zriedenej kyseline chlorovodíkovej a trikrát pretrepe 30 cm3 éteru. Po alkalizácii vodnej fázy sa uvoľnená báza vytrepe do éteru, vysuší bezvodým uhličitanom sodným. Po pridaní éterického roztoku suchého chlorovodíka sa vylúči biela kryštalická látka, ktorá sa prečisti kryštalizáciou z metanolu. Získa sa tuhý produkt vo výťažku 88 % teórie. Bezfarebné kryštáliky, 1.1. 135 až 140°C.To the reaction mixture of 2.2 g (0.01 mol) of 4-methoxyphenylcarbamic acid 2,3-epoxy-1-propyl ester in 30 cm 3 of ethanol is added 1.9 g (0.01 mol) of 1- (2-methoxyphenyl) piperazine and heated at the boiling point of the reaction mixture for 8 hours. Ethanol is distilled off under slight vacuum, the crude product is dissolved in dilute hydrochloric acid and shaken three times with 30 cm 3 of ether. After alkalization of the aqueous phase, the liberated base is shaken into ether, dried over anhydrous sodium carbonate. Upon addition of an ethereal solution of dry hydrogen chloride, a white crystalline solid precipitated which was purified by crystallization from methanol. A solid product is obtained in a yield of 88% of theory. Colorless crystals, 1.1. Mp 135-140 ° C.
S použitím uvedených postupov boli pripravené nasledujúce, v literatúre doteraz neopísané zlúčeniny: 1/ 3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hydroxy-lpropylester kyseliny 2-metoxyfenvlkarbámovej (ARK-721) hydrochlorid, 1.1. 117 až 121 °C (metanol)The following compounds have not been described in the literature yet: 1-3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-propyl 2-methoxyphenylcarbamic acid (ARK-721) hydrochloride, 1.1. 117-121 ° C (methanol)
IČ (cm ’, KBr) v(n_h) = 3 260, V(c=o) — 1 720, v(c=c) = = 1 525IR (cm -1, KBr) v ( n_h) = 3,260, V (c = o) - 1,720, v ( c = c) = = 1,525
UV (nm, metanol) 286, 238, 210UV (nm, methanol) 286, 238, 210
NMR (viď tabuľka)NMR (see table)
2/ 3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hydroxy-1 -propylester kyseliny 2-etoxyfenylkarbámovej (ARK-722) hydrochlorid, 1.1. 107 až 111°C (2-propanol)2 / 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 2-ethoxyphenylcarbamic acid ester (ARK-722) hydrochloride, 1.1. 107-111 ° C (2-propanol)
IČ (cm’1, KBr) = 3 300, v(C=0) = 1 740, v(c=C) = = 1 525IR (cm -1 , KBr) = 3,300, v (C = 0 ) = 1,740, v (c = C) = = 1,525
SK 278217 Β6SK 278217 Β6
UV (nm, metanol) 280, 238, 210UV (nm, methanol) 280, 238, 210
NMR (viď tabuľka) / 3-[4-(2-metoxyfeny 1)-1 -piperazinyl]-2-hydroxy-1 -propylester kyseliny 2-propoxyfenylkarbámovej (ARK-723) hydrochlorid, 1.1. 109 až 112°C (metanol)NMR (See Table) 2-Propoxyphenylcarbamic acid 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl ester (ARK-723) hydrochloride, 1.1. 109-112 ° C (methanol)
IČ (cm KBr) v(N=H) = 3 280, v(C=Oj = 1 725, V(c=c> = = 1 540IR (cm KBr) v (N = H) = 3280, v (C = O = 1725, V (c = c & gt ; = 1,540)
UV (nm, metanol) 280, 238, 208UV (nm, methanol) 280, 238, 208
NMR (viď tabuľka)NMR (see table)
4/ 3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hydroxy-l-propylester kyseliny 3-metoxyfenylkarbámovej (ARK-731) hydrochlorid, 1.1. 181 až 198°C (metanol: éter)4 / 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 3-methoxyphenylcarbamic acid (ARK-731) hydrochloride, m.p. 181-198 ° C (methanol: ether)
IC (cm , KBr) v^n-h) = 3 220, V(c=0) = 1 730, V(c=cj = = 1 490IC (cm, KBr) ν (nh) = 3,220, V (c = 0) = 1,730, V (c = cj = = 1,490)
U V (nm, metanol) 279, 238, 214Ν V (nm, methanol) 279, 238, 214
NMR (viď tabuľka)NMR (see table)
5/ 3-[4-(2-metoxyfenyl)-1 -piperazinyl]-2-hydroxy-l-propylester kyseliny 3-etoxyfenylkarbámovej (ARK-732) hydrochlorid, 1.1. 110 až 115°C (2-propanol)5 / 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 3-ethoxyphenylcarbamic acid (ARK-732) hydrochloride, 1.1. 110-115 ° C (2-propanol)
IČ (cm KBr) = 3 240, vfc=Oi = 1 725, V(c^c) = = 1525IR (cm KBr) = 3240, k = O to i = 1725, W (c ^ c) = = 1525
UV (nm, metanol) 280, 239, 212UV (nm, methanol) 280,239,212
NMR (viď tabuľka)NMR (see table)
6/ 3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hydroxy-l-propylester kyseliny 3-propoxyfenylkarbámovej (ARK-733) hydrochlorid, 1.1. 112 až 115°C (etanol)6 / 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 3-propoxyphenylcarbamic acid (ARK-733) hydrochloride, 1.1. 112-115 ° C (ethanol)
IČ (cm , KBr) ν^.^ = 3 235, V(C=0) = 1 725, V(q=q = = 1 525IR (cm, KBr) .delta. = 3,235, V ( C = O ) = 1,725, V (q = q = 1,525)
UV (nm, metanol) 280,239,212UV (nm, methanol) 280,239,212
NMR (viď tabuľka)NMR (see table)
7/ 3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hydroxy-l-propylester kyseliny 4-metoxyfenylkarbámovej (ARK-741) hydrochlorid, 1.1.135 až 140°C (metanol)7 / 3- [4- (2-Methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 4-methoxyphenylcarbamic acid (ARK-741) hydrochloride, mp.1.135 to 140 ° C (methanol)
IC (cm , KBr) V(n-h; = 3 200, ν^ε=θ^ ~ 1 710, = = 1 510IC (cm, KBr) V (nh; = 3200, ν ^ ε = θ ^ ~ 1710, = = 1 510
UV (nm, metanol) 282, 240, 210UV (nm, methanol) 282, 240, 210
NMR (viď tabuľka)NMR (see table)
8/ 3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hydroxy-l-propylester kyseliny 4-etoxyfenylkarbámovej (ARK5 -742) hydrochlorid, 1.1. 167 až 170°C (etanol)8 / 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 4-ethoxyphenylcarbamic acid (ARK5-742) hydrochloride, 1.1. 167-170 ° C (ethanol)
IČ (cm ’, KBr) v^.hj = 3 230, vy^oj = 1 710, V(c=c; = = 1 500IR (cm ', KBr) v ^ .hj = 3 230, ^ = 1710, V (c = c; = = 1 500
UV (nm, metanol) 281, 241, 208UV (nm, methanol) 281, 241, 208
10 NMR (viď tabuľka)1 0 NMR (see table)
9/ 3-[4-(2-metoxyfenyl)-1 -piperaziny l]-2-hydroxy-1 -propylester kyseliny 4-propoxyfenylkarbámovej (ARK-743) hydrochlorid, 1.1. 169 až 170°C (etanol) 15 IC (cm’1, KBr) V(n.h) = 3 235, ν(ε=0) = 1 710, v(C=C) = = 1 5104 / Propoxyphenylcarbamic acid 9 / 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl ester (ARK-743) hydrochloride, 1.1. 169-170 ° C (ethanol) 15 IC (cm -1 , KBr) V (n .h) = 3,235, ν (ε = 0) = 1,710, v (C = C ) = 1,510
UV (nm, metanol) 282, 242, 208UV (nm, methanol) 282, 242, 208
NMR (viď tabuľka)NMR (see table)
Výsledky skúšok biologickej aktivityResults of biological activity tests
Pri štúdiu antidisrytmickej aktivity 3-[4-(2-metoxyfenyl)-1 -piperazinyl]-2-hydroxy-1 -propylesteru kyseliny 2-etoxyfenylkarbámovej (ARK-722) bola použitá 25 modifikovaná metóda podľa Pávka a Seleckého (PávckIn the study of the anti-arrhythmic activity of 3- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl 2-ethoxyphenylcarbamic acid ester (ARK-722), 25 modified method according to Páv and Selecký (Pávck) was used.
K., Selecký F.: Brat lek. Listy 8: 481, (1961)). Hodnotil sa protektívny efekt látky voči disrytmiám indukovaným i. v. aplikáciu dvoch rovnakých, v odstupe 30 sekúnd za sebou nasledujúcich dávok adrenalínu 5Q v celkovej dávke 40 pg.kg’1. Antidisrytmický efekt látky bol vyjadrený počtom extrasystol, indukovaných párovou dávkou adrenalínu:K., Selecký F .: Brother Lect. Letters 8: 481, (1961)). The protective effect of the compound against iv-induced disrhythmias was evaluated with two equal 30 seconds of consecutive doses of adrenaline 50 in a total dose of 40 pg.kg -1 . The antidisrhythmic effect of the substance was expressed by the number of extrasystoles induced by a paired dose of adrenaline:
kontrola 12,4+1,9 ARK-722 0,3 ±0,2control 12.4 + 1.9 ARK-722 0.3 ± 0.2
Rozdiel voči kontrole je štatisticky významný.The difference to control is statistically significant.
13C - NMR spektrá látok série ARK. 13 C-NMR spectra of compounds of the ARK series.
.2 Cl.2 Cl
SK 278217 Β6 'H - NMR spektrá série látok ARK.6 H-NMR spectra of the ARK series.
.2.2
ClCl
Priemyselná využiteľnosťIndustrial usability
3-[4-(2-metoxyfenyl)-l-piperazinyl]-2-hydroxy-l-propylestery kyselín alkoxyfenylkarbámových je možné použiť vo farmaceutickom priemysle a v medicíne. 53- [4- (2-methoxyphenyl) -1-piperazinyl] -2-hydroxy-1-propyl esters of alkoxyphenylcarbamic acids can be used in the pharmaceutical industry and in medicine. 5
3. Spôsob prípravy substituovaných esterov alkoxyfenylkarbámovej kyseliny všebecného vzorca I podľa nároku 1, vyznačujúci sa tým, že sa nechá reagovať 2,3-epoxy-l-propylester kyseliny alkoxyfenylkarbámovej všeobecného vzorca IIIA process for the preparation of substituted alkoxyphenylcarbamic esters of general formula I according to claim 1, characterized in that the 2,3-epoxy-1-propyl ester of alkoxyphenylcarbamic acid of the general formula III is reacted.
Claims (2)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2821356A1 (en) * | 2001-02-23 | 2002-08-30 | Cerep | NOVEL ARYLCARBAMATE AND ARYLUREES DERIVATIVES, PREPARATIONS AND USES |
FR2843750A1 (en) * | 2002-08-23 | 2004-02-27 | Cerep | New (homo)piperazinyl-alkyl (hetero)aryl-carbamate compounds are 5-hydroxytryptamine 4 receptor ligands useful for treating gastrointestinal, CNS, cardiac or urogenital disorders, pain or migraine |
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1993
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2821356A1 (en) * | 2001-02-23 | 2002-08-30 | Cerep | NOVEL ARYLCARBAMATE AND ARYLUREES DERIVATIVES, PREPARATIONS AND USES |
WO2002068399A1 (en) * | 2001-02-23 | 2002-09-06 | Cerep | Aryl carbamate derivatives, preparation and use thereof |
FR2843750A1 (en) * | 2002-08-23 | 2004-02-27 | Cerep | New (homo)piperazinyl-alkyl (hetero)aryl-carbamate compounds are 5-hydroxytryptamine 4 receptor ligands useful for treating gastrointestinal, CNS, cardiac or urogenital disorders, pain or migraine |
WO2004018436A3 (en) * | 2002-08-23 | 2004-04-15 | Cerep | Compounds derived from aryl carbamates, preparation thereof and uses of same |
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