DE2622999A1 - Process for the preparation of N-(1-ETHYL-2-PYRROLIDINYLMETHYL)-2-METHOXY-5-SULFAMOYLBENZAMIDE - Google Patents
Process for the preparation of N-(1-ETHYL-2-PYRROLIDINYLMETHYL)-2-METHOXY-5-SULFAMOYLBENZAMIDEInfo
- Publication number
- DE2622999A1 DE2622999A1 DE19762622999 DE2622999A DE2622999A1 DE 2622999 A1 DE2622999 A1 DE 2622999A1 DE 19762622999 DE19762622999 DE 19762622999 DE 2622999 A DE2622999 A DE 2622999A DE 2622999 A1 DE2622999 A1 DE 2622999A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- ethyl
- pyrrolidinylmethyl
- sulfamoylbenzamide
- preparation
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
GLAWE1 DELFS, MOLL & PARTNER PATENTANWÄLTEGLAWE 1 DELFS, MOLL & PARTNER PATENTANWÄLTE
DR ING. RICHARD GLAWE, MÖNCHEN DIPL.-ING. KLAUS DELFS. HAMBURG DIPL.-PHYS. DR. WALTER MOLL, MÖNCHEN DIPL.-CHEM. DR. ULRICH MENGDEHL, HAMBURGDR ING. RICHARD GLAWE, MÖNCHEN DIPL.-ING. KLAUS DELFS. HAMBURG DIPL.-PHYS. DR. WALTER MOLL, MÖNCHEN DIPL.-CHEM. DR. ULRICH MENGDEHL, HAMBURG
' ' 8 MÖNCHEN 26 2 HAMBURG 13'' 8 MÖNCHEN 26 2 HAMBURG 13
POSTFACH 37 POSTFACH 2570PO Box 37 PO Box 2570
ROTHENBAUM-ROTHENBAUM-
LIEBHERRSTR. 20 CHAUSSEE 58LIEBHERRSTR. 20 CHAUSSEE 58
TEL. (089) 22 65 48 TEL. (040) 4 10 20TEL. (089) 22 65 48 TEL . (040) 4 10 20
TtLEX 52 25 05 TELEX 21 29 21TtLEX 52 25 05 TELEX 21 29 21
HAMBURGHAMBURG
ρ 8016/75 M/esρ 8016/75 M / es
Societe d'Etudes Scientifiques et Industrielles de l'Ile-de-France, 46, bd. de Latour-Maubourg, F-75 34o Paris CEDEX 07Societe d'Etudes Scientifiques et Industrielles de l'Ile-de-France, 46, vol. de Latour-Maubourg, F-75 34o Paris CEDEX 07
Verfahren zur Herstellung von N-(l-Ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamoylbenz aidProcess for the preparation of N- (1-ethyl-2-pyrrolidinylmethyl) -2-methoxy-5-sulfamoylbenz aid
Die Erfindung betrifft ein Verfahren zur Herstellung von N-(1-Ethy1-2-pyrrolidiny!methyl)-2-methoxy-5-sulfamoylbenzamid, seiner Additionssalze mit pharmazeutisch verträglichen anorganischen oder organischen Säuren und seiner quaternären Ammoniumsalze, welche durch Umsetzung des Benzamids mit einem Reagenz zur Einführung eines einwertigen aliphatischen oder aromatischen Kohlenwasserstoffrestes erhältlich sind.The invention relates to a process for the preparation of N- (1-Ethy1-2-pyrrolidiny! Methyl) -2-methoxy-5-sulfamoylbenzamide, its addition salts with pharmaceutically acceptable inorganic or organic acids and its quaternary Ammonium salts, which by reacting the benzamide with a reagent for the introduction of a monovalent aliphatic or aromatic hydrocarbon radicals are available.
Gemäß dem Verfahren der Erfindung können Enamine der allgemeinen Formel (i) oder Salze derselben mit 2-Methoxy-5-sulfamoylbenzoesäure oder einem reaktiven Derivat derselben, z.B. ihrem Säurechlorid, wie folgt umgesetzt werden:According to the process of the invention, enamines of the general formula (i) or salts thereof with 2-methoxy-5-sulfamoylbenzoic acid or a reactive derivative thereof, e.g. its acid chloride, can be reacted as follows:
Rn -C=CH-R0 1 ι L R n -C = CH-R 0 1 ι L
NHNH
N-N-
C2H5 C 2 H 5
, HCl +, HCl +
COOHCOOH
OCH.OCH.
bzw. ein reaktives Derivator a reactive derivative
CONH-CH,. —CONH-CH ,. -
ι—OCHι — OCH
H2NO2S H 2 NO 2 S
In den obigen Formeln bedeuten R, eine organische Gruppe und R„ eine Acy!gruppe.In the above formulas, R 1 denotes an organic group and R 1 denotes an acyl group.
Geeignete organische Reste für die Gruppe R, sind beispielsweise Alky!gruppen wie Methyl-, Ethyl-, Propyl- oder Buty!gruppen, oder dergleichen.Suitable organic radicals for the group R are, for example, alkyl groups such as methyl, ethyl, propyl or buty groups, or similar.
Geeignete Acylreste für die Gruppe R„ sind beispielsweise
Alkanoylgruppen wie Acetyl- oder Propionylgruppen, Alkoxycarbonylgruppen wie Methoxycarbonyl-, Ethoxycarbonyl-, Propoxycarbonyl-
oder Butoxycarbonylgruppen, oder dergleichen.Suitable acyl radicals for the group R "are, for example
Alkanoyl groups such as acetyl or propionyl groups, alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl or butoxycarbonyl groups, or the like.
Das erfindungsgemäß hergestellte Benzamid weist wichtige
pharmakologxsche Eigenschaften auf, die von uer Anmelderin
in den französischen Patenten 4879 M und 5916 M vom 1. April 1965 und 21. Januar 19o6 beschrieben wurden.The benzamide produced according to the invention has important
pharmacological properties that have been reported by the applicant
in French patents 4879 M and 5916 M of April 1, 1965 and January 21, 19o6.
609853/ 1058609853/1058
Das Verfahren der Erfindung wird im folgenden anhand eines Ausführungsbeispiels näher erläutert.The method of the invention is explained in more detail below using an exemplary embodiment.
N-(1-Ethyl -2-pyrrolidinylmethyl)-2-methoxy-5-sulfamoylbenzamidN- (1-Ethyl -2- pyrrolidinylmethyl) -2-methoxy-5-sulfamoylbenzamide
5,26 g (0,02MoI) N-(l-Ethyl-2-pyrrolidinylmethyl)-methyl-3-aminocrotonat-Hydrochlorid und 200 ml Dichlorethan werden in einen 1 1-Kolben gegeben, der mit einem Rührer, einem Thermometer und einem Rückflußkühler versehen ist.5.26 g (0.02 mol) of N- (1-ethyl-2-pyrrolidinylmethyl) -methyl-3-aminocrotonate hydrochloride and 200 ml of dichloroethane are placed in a 1 1 flask with a stirrer, a Thermometer and a reflux condenser is provided.
Das Gemisch wird erhitzt, bis sich der Feststoff gelöst hat. Anschließend wird eine heiße Lösung von 2 y (0,02 Mol) 2-Methoxy-5-sul£amoylbenzoylchlorid in 200 ml Dichlorethan in einem dünnen Strahl in das Gefäß gegossen. Das Reaktionsgemisch wird anschließend sechs Stunden am Rückfluß erhitzt, etwa 10 Minuten bilden sich Kristalle aus. Man läßt das Gemisch abkühlen und über Nacht stehen. Der gebildete Niederschlag wird abfiltriert, heiß in einer wässrigen Salzsäurelösung gelöst und über Aktivkohle filtriert. Die Lösung wird mit Ammoniak alkalisch gemacht. Die gebildeten Kristalle werden filtriert, mit Wasser gewaschen und in einem Trockenofen bei 50°C getrocknet.The mixture is heated until the solid has dissolved. Then a hot solution of 2 y (0.02 mol) Poured 2-methoxy-5-sulphoylbenzoyl chloride in 200 ml of dichloroethane in a thin stream into the vessel. The reaction mixture is then refluxed for six hours, crystals form for about 10 minutes. The mixture is allowed to cool and stand overnight. The precipitate formed is filtered off, hot in an aqueous hydrochloric acid solution dissolved and filtered through activated charcoal. The solution is made alkaline with ammonia. The crystals formed will be filtered, washed with water and dried in a drying oven at 50 ° C.
Man erhält 3, 7 g N-(l-gthyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamoylbenzamid in einer Ausbeute von 54, 2 % und mit einem Schmelzpunkt von 178°C.3.7 g of N- (l-ethyl-2-pyrrolidinylmethyl) -2-methoxy-5-sulfamoylbenzamide are obtained in a yield of 54.2 % and with a melting point of 178.degree.
+ Nach+ After
6 0.9 853/10586 0.9 853/1058
Claims (1)
1 ι ΖR 1 -C = CH-R_
1 ι Ζ
CH,NH
CH,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518824A FR2314918A1 (en) | 1975-06-17 | 1975-06-17 | NEW PROCESS FOR THE PREPARATION OF N- (1-ETHYL-2-PYRROLIDYLMETHYL) 2-METHOXY 5-SULFAMOYL BENZAMIDE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2622999A1 true DE2622999A1 (en) | 1976-12-30 |
Family
ID=9156603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762622999 Withdrawn DE2622999A1 (en) | 1975-06-17 | 1976-05-22 | Process for the preparation of N-(1-ETHYL-2-PYRROLIDINYLMETHYL)-2-METHOXY-5-SULFAMOYLBENZAMIDE |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS6016415B2 (en) |
| AT (1) | AT349457B (en) |
| CA (1) | CA1078397A (en) |
| DE (1) | DE2622999A1 (en) |
| FI (1) | FI761746A7 (en) |
| FR (1) | FR2314918A1 (en) |
| GB (1) | GB1501771A (en) |
| IE (1) | IE43003B1 (en) |
| MX (1) | MX3581E (en) |
| PT (1) | PT65167B (en) |
-
1975
- 1975-06-17 FR FR7518824A patent/FR2314918A1/en active Granted
-
1976
- 1976-05-22 DE DE19762622999 patent/DE2622999A1/en not_active Withdrawn
- 1976-06-01 IE IE1169/76A patent/IE43003B1/en unknown
- 1976-06-01 AT AT399976A patent/AT349457B/en not_active IP Right Cessation
- 1976-06-01 PT PT65167A patent/PT65167B/en unknown
- 1976-06-09 MX MX76294U patent/MX3581E/en unknown
- 1976-06-09 CA CA254,482A patent/CA1078397A/en not_active Expired
- 1976-06-10 GB GB24112/76A patent/GB1501771A/en not_active Expired
- 1976-06-14 JP JP51070315A patent/JPS6016415B2/en not_active Expired
- 1976-06-16 FI FI761746A patent/FI761746A7/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1501771A (en) | 1978-02-22 |
| FI761746A7 (en) | 1976-12-18 |
| ATA399976A (en) | 1978-09-15 |
| PT65167B (en) | 1977-11-17 |
| PT65167A (en) | 1976-07-01 |
| IE43003B1 (en) | 1980-12-03 |
| JPS6016415B2 (en) | 1985-04-25 |
| IE43003L (en) | 1976-12-17 |
| CA1078397A (en) | 1980-05-27 |
| FR2314918B1 (en) | 1977-12-09 |
| MX3581E (en) | 1981-03-19 |
| AT349457B (en) | 1979-04-10 |
| JPS52262A (en) | 1977-01-05 |
| FR2314918A1 (en) | 1977-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |