FI56677C - NYTT FOERFARANDE FOER FRAMSTAELLNING AV N- (DIETYLAMINOETYL) -2-METHOXY-4-AMINO-5-CHLORBENAMIDE OCH DESS PHARMACEUTICAL SODIUM SYRAAD DITIONSSALTER - Google Patents

NYTT FOERFARANDE FOER FRAMSTAELLNING AV N- (DIETYLAMINOETYL) -2-METHOXY-4-AMINO-5-CHLORBENAMIDE OCH DESS PHARMACEUTICAL SODIUM SYRAAD DITIONSSALTER Download PDF

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FI56677C
FI56677C FI1953/73A FI195373A FI56677C FI 56677 C FI56677 C FI 56677C FI 1953/73 A FI1953/73 A FI 1953/73A FI 195373 A FI195373 A FI 195373A FI 56677 C FI56677 C FI 56677C
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methoxy
amino
chlorobenzamide
syraad
ditionssalter
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FI56677B (en
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Gerard Bulteau
Jacques Acher
Jean-Claude Monier
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Ile De France
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

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Description

\0*Τ·1 rB1 rt1v KUULUTUSJULKAISU c „ „ 11 UTLÄGGNINGSSKRIFT Sbb / 7 C Patentti myönnetty 10 03 1930\ 0 * Τ · 1 rB1 rt1v ADVERTISEMENT c „„ 11 UTLÄGGNINGSSKRIFT Sbb / 7 C Patent granted 10 03 1930

Patent aeddelat (51) Kr.lk.*/lnt.a.* C 07 0 103/82 SUOMI—FINLAND (21) Puenttlhakemu*—P«tenttns6knlng 1953/73 (22) Hakemispilvi—AnsSkningtdtg l8.06.73 (23) Alkupllvi—Glltlghetsdag l8.06.73 (41) Tullut Julkiseksi—Blivlt offentllg 21.12.73Patent aeddelat (51) Kr.lk. * / Lnt.a. * C 07 0 103/82 FINLAND — FINLAND (21) Puenttlhakemu * —P «tenttns6knlng 1953/73 (22) Hakemispilvi — AnsSkningtdtg l8.06.73 (23) Alkupllvi —Glltlghetsdag l8.06.73 (41) Become Public — Blivlt offentllg 21.12.73

Patentti· ja rekisterihallitus >«.«. «h regifterityrelMn <«> 30.11.79 (32) (33) (31) Pyydetty etuoikeus—Begird prloritet 2 0.06.7 2National Board of Patents and Registration> «.«. «H regifterityrelMn <«> 30.11.79 (32) (33) (31) Privilege claimed — Begird prloritet 2 0.06.7 2

Ranska-Frankrike(FR) 72/22288 (71) Societe d'Etudes Scientifiques et Industrielles de 1'Ile-de-France, U6, boulevard de Latour-Maubourg, 75 Paris 7°, Ranska-Frankrike(FR) (72) Gerard Bulteau, Paris, Jacques Acher, Itteville, Jean-Claude Monier,France-Frankrike (FR) 72/22288 (71) Societe d'Etudes Scientifiques et Industrielles de 1'Ile-de-France, U6, Boulevard de Latour-Maubourg, 75 Paris 7 °, France-Frankrike (FR) (72) Gerard Bulteau, Paris, Jacques Acher, Itteville, Jean-Claude Monier,

Lardy, Ranska-Frankrike(FR) (7*0 Oy Kolster Ab (5^) Uusi menetelmä N-(dietyyliaminoetyyli)-2-metoksi-U-amino-5-klooribents-amidin ja sen farmaseuttisesti hyväksyttävien happoadditiosuolojen ja kvaternääristen ammoniumsuolojen valmistamiseksi — Nytt förfarande för framställning av N-(dietylaminoetyl)-2-metoxi-U-amino-5-klorbensamid och dess farmaceutiskt godtagbara syraadditionssalter samt kvaternära ammoniumsalterLardy, France-France (FR) (7 * 0 Oy Kolster Ab (5 ^) New process for the preparation of N- (diethylaminoethyl) -2-methoxy-U-amino-5-chlorobenzamide and its pharmaceutically acceptable acid addition salts and quaternary ammonium salts - It is now possible to obtain N- (diethylaminoethyl) -2-methoxy-U-amino-5-chlorobenzamide and a pharmaceutical solution of the addition of a quaternary ammonium salt.

Keksinnön kohteena on uusi menetelmä N-(dietyyliaminoetyyli )-2-metoksi-U-ainino-5-klooribentsamidin valmistamiseksi, jonka kaava on /C2H5 conhch2ch2n ,;,H' -φΓ ’ nh2 ja sen farmaseuttisesti hyväksyttävien epäorgaanisten tai orgaanisten happojen kanssa muodostettavien happoadditosuojen sekä sen kvaternääristen ammoniumsuolojen valmistamiseksi.The present invention relates to a new process for the preparation of N- (diethylaminoethyl) -2-methoxy-U-amino-5-chlorobenzamide of the formula / C2H5 conhch2ch2n, H, -φΓ'nh2 and its pharmaceutically acceptable inorganic or organic acid addition moieties. and for the preparation of its quaternary ammonium salts.

Keksinnön mukaisesti valmistetulla bentsamidilla on erinomaiset ominaisuudet antiemeettisenä Ja ruoansulatusta modifioivana aineena.The benzamide prepared according to the invention has excellent properties as an antiemetic and a digestive modifier.

2 566772 56677

Tunnetut menetelmät N-(dietyyliaminoetyyli)-2-metoksi-U-arnino-5-kloori-bentsamidin valmistamiseksi on esitetty FR-patentissa 1 313 758 ja GB-patentissa 1 019 7Ö1. Keksinnölle saadaan aikaan erityistä sikäli, että uusi menetelmä toteutetaan uusien välituotteiden N-(2-hydrcetyyli)-2-metoksi-^-asetamino-5~kloori-bentsamidin ja H-(2-kloorietyyli)-2-metaksi-U-amino-5-klooribentsamidin kautta, jolloin voidaan käyttää lähtöaineina etanoliamiinia ja dietyyliamiinia, jotka ovat helpommin valmistettavissa ja näin ollen taloudellisesti edullisempia kuin tunnettujen menetelmien lähtöaine N,N-dietyylietyleenidiamiini.Known processes for the preparation of N- (diethylaminoethyl) -2-methoxy-U-amino-5-chlorobenzamide are disclosed in FR Patent 1,313,758 and GB Patent 1,019,701. The invention is particularly provided in that the new process is carried out on the novel intermediates N- (2-hydroxyethyl) -2-methoxy-N-acetamino-5-chlorobenzamide and H- (2-chloroethyl) -2-methoxy-U-amino- Via 5-chlorobenzamide, which can be used as starting materials ethanolamine and diethylamine, which are easier to prepare and thus more economically advantageous than the starting material N, N-diethylethylenediamine by known methods.

Keksinnölle on tunnusomaista, että 2-metoksi-k-asetamino-5~klooribentsoe-hapon esteri, jonka kaava on:The invention is characterized in that the ester of 2-methoxy-k-acetamino-5-chlorobenzoic acid has the formula:

C00RC00R

... - NHC0CH3 jossa R on alempi alkyyliryhmä, joka sisältää 1-3 hiiliatomia, saatetaan reagoimaan etanoli amiini n kanssa ja saatua N-( etan-2-oli )-2-metoksi-U-asetamino-5.-klooribentsamidia käsitellään tionyylikloridillä N-( 2-kloorietyyli)-2-metoksi-U-amino-5-klooribentsamidin saamiseksi,' joka saatetaan reagoimaan dietyyliamiinin kanssa N-(dietyyliaminoetyyli)-2-metoksi-U-amino-5-klooribentsamidin saamiseksi.... - NHCOCH 3 in which R is a lower alkyl group containing 1 to 3 carbon atoms is reacted with ethanol amine and the resulting N- (ethan-2-ol) -2-methoxy-U-acetamino-5-chlorobenzamide is treated with thionyl chloride To obtain N- (2-chloroethyl) -2-methoxy-U-amino-5-chlorobenzamide, which is reacted with diethylamine to give N- (diethylaminoethyl) -2-methoxy-U-amino-5-chlorobenzamide.

Keksinnön mukaisen menetelmän ensimmäisessä vaiheessa bentsoehapon esteriä käsitellään etanoli amiinilla liuottimen kuten bentseenin tai ksyleenin ja mahdollisesti katalysaattorin läsnäollessa palautusjäähdytysiämpötilassa^ toisessa vaiheessa N-(2-hydroksietyyli)bentsamidia käsitellään tionyyllä huoneen lämpötilassa; kolmannessa vaiheessa N-( 2-kloorietyyli)bentsamidia käsitellään di-etyyli ami i ni11a palautus j äähdytyslämpötilas s a,In the first step of the process according to the invention, the benzoic acid ester is treated with ethanolamine in the presence of a solvent such as benzene or xylene and optionally a catalyst at reflux temperature; in the second step, N- (2-hydroxyethyl) benzamide is treated with thionyl at room temperature; in the third step, N- (2-chloroethyl) benzamide is treated with diethyl amine at reflux temperature,

Reaktiokaavio on seuraava: 3 66677 COOH ΟΟϋΗΟΗ,-ΟΗ,ΟΒ -ί^\_οοΗ5 r^ir~ ocb5The reaction scheme is as follows: 3 66677 COOH ΟΟϋΗΟΗ, -ΟΗ, ΟΒ -ί ^ \ _ οοΗ5 r ^ ir ~ ocb5

H2HCH20H20BH2HCH20H20B

°1——-> Cl— NHCOCSL NHCOCH, (I) (II) COUHCHg-CHgOH COBHCHgCHgCl * KH0 KHCOCHj 2 (II) (in) COKHCHgCHgCl 001^0112^2^1^° 2K5 — 0023 f^S—OCHj Λ "° 1 ——-> Cl- NHCOCSL NHCOCH, (I) (II) COUHCHg-CHgOH COBHCHgCHgCl * KHO KHCOCHj 2 (II) (in) COKHCHgCHgCl 001 ^ 0112 ^ 2 ^ 1 ^ ° 2K5 - 0023 f ^ S — OCHj Λ "

dletyylia.iini ^ Cli^Jdlethyl.iin ^ Cli ^ J

HH2 m2 (III) (IV)HH2 m2 (III) (IV)

Seuraava esimerkki kuvaa keksintöä: N(dietyyliaminoetyyli)-2-metoksi-4-amino-5-klooribentsamidi Vaihe I: N(etan-2-oli)-2-metoksi-4-aeetamino-5-klooribentsarai<ii 200 g (0,78 moolia) metyyli-2-metoksi-4-asetamino-3-klooribontKoa&itia, 57 g (0,93 moolia) etanoliamiinia, 460 ml ksyleeniä ja 20 g alu'jiniamisoiLxopy--laattia pannaan kahden litran keittopulloon, joka on varustatte, sekoitt-tm'Via, " jäähdyttimellä, lämpömittarilla ja tislauslaitteella.The following example illustrates the invention: N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide Step I: N- (Ethan-2-ol) -2-methoxy-4-acetamino-5-chlorobenzarate 200 g (0 , 78 moles) of methyl 2-methoxy-4-acetamino-3-chlorobondocool, 57 g (0.93 moles) of ethanolamine, 460 ml of xylene and 20 g of alumineamolxopylate are placed in a two-liter beaker equipped with stirring. -tm'Via, "with condenser, thermometer and distillation apparatus.

Seosta kuumennetaan palautusjäähdyttäen 3 tunti?, jäähdytetään ja d0~ kantoidaan ylempi faasi, öljy liuotetaan 300 mlJaan dioksaania, suodatetaan liukenematon aine pois ja haihdutetaan liuotin.The mixture is heated under reflux for 3 hours, cooled and carried over to the upper phase, the oil is dissolved in 300 ml of dioxane, the insoluble matter is filtered off and the solvent is evaporated off.

Jäännös liuotetaan osittain asetonitriiliin. Liuoksen annetaan seitVä yli yön jäähdyttimessä, suodatetaan ja haihdutetaan liuotin.The residue is partially dissolved in acetonitrile. The solution is allowed to stand overnight in a condenser, filtered and the solvent is evaporated.

Saadaan 89 g tf(etan-2-oli)-2-metoksi-4-asetamino-5-klcorihentcami.uA? (sulamispiste 170°C).89 g of tf (ethan-2-ol) -2-methoxy-4-acetamino-5-chlorohentcami.uA are obtained. (melting point 170 ° C).

Vaihe II: N(2-kloorietyyli)-2-metoksi-4-amino-5-klooribentsamidi 3 g (0,01 moolia) N(etan-2-oli)-2-metokoi-4“a<5etamino-5-kIooriberiti:;ar'..:· dia ja 15 ml tioryylikloridia pannaan 100 ml:n keittopulloon, joka on varustettu sekoittimella, lämpömittarilla ja jäähdyttimellä, ja sekoitetaan seor.ia 4 S667 7 7 tuntia ympäristön lämpötilassa.Step II: N- (2-chloroethyl) -2-methoxy-4-amino-5-chlorobenzamide 3 g (0.01 mol) of N- (ethan-2-ol) -2-methochol-4-α-5-amino-5- The chloride and 15 ml of thioryl chloride are placed in a 100 ml beaker equipped with a stirrer, thermometer and condenser and stirred for 4 hours at ambient temperature.

Tionyylikloridi haihdutetaan tyhjössä , jäännös pestään vedellä ja suodatetaan» pestään natriumhydroksidilla, suodatetaan uudelleen» pestään vedellä ja kuivataan sitten eksikkaattorissa tyhjiössä kaiiumhydroksidin läsnäollessa.The thionyl chloride is evaporated off under vacuum, the residue is washed with water and filtered, washed with sodium hydroxide, filtered again, washed with water and then dried in a desiccator under vacuum in the presence of potassium hydroxide.

Saadaan 2»Θ0 g N(2-kloorietyyli)-2-metoksi-4-amino-5-klooribent8amidia (sulamispiste 140°C).2 x 10 g of N- (2-chloroethyl) -2-methoxy-4-amino-5-chlorobenzamide (melting point 140 ° C) are obtained.

Vaihe III: N(dietyyliaminoetyyli)-2-metoksi-4-amino-5“klooribentsamidi 2,5 g (0,0095 moolia) N(2-kloorietyyli)-2-metoksi-4-amino-5-klooribents-amidia ja 55 ml dietyyliamiinia pannaan 50 ml:n keittopulloon, joka on varustettu jäähdyttimellä ja sekoittimella, ja seosta kuumennetaan palautusjääh-dyttäen 5 päivää.Step III: N- (diethylaminoethyl) -2-methoxy-4-amino-5 'chlorobenzamide 2.5 g (0.0095 mol) of N- (2-chloroethyl) -2-methoxy-4-amino-5-chlorobenzamide and 55 ml of diethylamine are placed in a 50 ml beaker equipped with a condenser and a stirrer, and the mixture is heated under reflux for 5 days.

Seos jäähdytetään ja suodatetaan ja suodos haihdutetaan. Jäännös liuotetaan 18 ml:aan N kloorivetyhappoa, suodatetaan sitten ja pestään vedellä sekä tehdään liuos alkaliseksi 20 ml:11a 40 Joista natriumhydroksidia.The mixture is cooled and filtered and the filtrate is evaporated. The residue is dissolved in 18 ml of N hydrochloric acid, then filtered and washed with water and the solution is made alkaline with 20 ml of sodium hydroxide.

Lisätään 20 ml vettä ja kuumennetaan liuosta palautusjäähdyttäen 1,5 tuntia.Add 20 ml of water and heat the solution to reflux for 1.5 hours.

Tämän jälkeen jäähdytetään, suodatetaan ja kiteytetään uudelleen bent-seenistä.It is then cooled, filtered and recrystallized from Bentene.

Saadaan 0,7 e N(dietyyliaminoetyyli)-2-metoksi-4-amino-5-klooribents-amidia (sulamispiste 143°0).0.7 e of N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide (melting point 143 DEG C.) is obtained.

Claims (2)

1. Uusi menetelmä N-(dietyyliaminoetyyli)-2-metoksi-k-amino-5-kloori-bentsamidin valmistamiseksi, jonka kaava on yC2K5 conhch2ch2n (IV) Ar- A'2"5 C1'V nh2 ja sen farmaseuttisesti hyväksyttävien epäorgaanisten tai orgaanisten happo-jen kanssa muodostettavien happoadditiosuolojen sekä sen kvaternääristen ammoniumsuolojen valmistamiseksi, tunnettu siitä, että 2-metoksi- 4-aset£imino-5-klooribentsoehapon est*ti, jonka kaava on: COOR A" MHCOCH3 jossa R on alempi alkyyliryhmä, joka sisältää 1-3 hiiliatomia, saatetaan reagoimaan etanoliamiinin kanssa ja saatua N-( etan-2-oli )-2-metoksi-k-asetamino-5-klooribentsamidia käsitellään tionyylikloridilla N-(2-kloorietyyli)-2-metoksi-k-amino-5-klooribentsamidin saamiseksi, joka saatetaan reagoimaan dietyyliamiinin kanssa N-(dietyyliaminoetyyli)-2-metoksi-k-amino-5-klooribentsamidin saamiseksi , joka haluttaessa muutetaan happoadditiosuolakseen tai kvaternääriseksi ammoniumsuolakeeen.A new process for the preparation of N- (diethylaminoethyl) -2-methoxy-k-amino-5-chlorobenzamide of the formula yC2K5 conhch2ch2n (IV) Ar-A'2 "5 C1'V nh2 and its pharmaceutically acceptable inorganic or for the preparation of acid addition salts with organic acids and its quaternary ammonium salts, characterized in that the 2-methoxy-4-acetylimino-5-chlorobenzoic acid ester has the formula: COOR A "MHCOCH3 in which R is a lower alkyl group containing 1-3 carbon atoms, is reacted with ethanolamine and the resulting N- (ethan-2-ol) -2-methoxy-k-acetamino-5-chlorobenzamide is treated with thionyl chloride N- (2-chloroethyl) -2-methoxy-k-amino- To obtain 5-chlorobenzamide which is reacted with diethylamine to give N- (diethylaminoethyl) -2-methoxy-k-amino-5-chlorobenzamide, which is optionally converted to its acid addition salt or quaternary ammonium salt. 2. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu siitä, että käytetty esteri on metyyli-2-metoksi-4-asetamino-5-klooribentsoaatti.Process according to Claim 1, characterized in that the ester used is methyl 2-methoxy-4-acetamino-5-chlorobenzoate.
FI1953/73A 1972-06-20 1973-06-18 NYTT FOERFARANDE FOER FRAMSTAELLNING AV N- (DIETYLAMINOETYL) -2-METHOXY-4-AMINO-5-CHLORBENAMIDE OCH DESS PHARMACEUTICAL SODIUM SYRAAD DITIONSSALTER FI56677C (en)

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Application Number Priority Date Filing Date Title
FR7222288 1972-06-20
FR7222288A FR2277815A1 (en) 1972-06-20 1972-06-20 NEW PROCESS FOR THE PREPARATION OF N (DIETHYLAMINOETHYL) 2-METHOXY 4-AMINO 5-CHLOROBENZAMIDE

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FI56677B FI56677B (en) 1979-11-30
FI56677C true FI56677C (en) 1980-03-10

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JPS5881689U (en) * 1981-11-25 1983-06-02 富士電機冷機株式会社 Cup type vending machine
JPS59155682U (en) * 1983-04-05 1984-10-19 東芝機器株式会社 beverage vending machine
US4808624A (en) * 1984-06-28 1989-02-28 Bristol-Myers Company Pharmacologically active substituted benzamides
JPH02148390A (en) * 1988-11-30 1990-06-07 Fuji Electric Co Ltd Automatic vending machine for hot commodity
US10539725B2 (en) 2016-11-30 2020-01-21 Samsung Electronics Co., Ltd. Optical filter and camera module and electronic device
CN113698321B (en) * 2021-09-30 2023-04-18 内蒙古康普药业有限公司 New metoclopramide diamine impurity and application

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DK131030C (en) 1975-10-20
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ES415952A1 (en) 1976-02-01
FI56677B (en) 1979-11-30
IE37800B1 (en) 1977-10-12
CA1001170A (en) 1976-12-07
MC1007A1 (en) 1974-10-18
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BE801038A (en) 1973-12-18
SE421070B (en) 1981-11-23
IE37800L (en) 1973-12-20
KR780000231B1 (en) 1978-07-01
RO64465A (en) 1979-05-15
LU67805A1 (en) 1974-07-10
FR2277815B1 (en) 1978-10-20
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JPS5070334A (en) 1975-06-11
BG22073A3 (en) 1976-11-25
HU166936B (en) 1975-06-28
AU5699473A (en) 1974-12-19
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BG22074A3 (en) 1976-11-25
FR2277815A1 (en) 1976-02-06
YU160773A (en) 1982-06-18
CH568277A5 (en) 1975-10-31
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