CA1078397A - Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamide - Google Patents
Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamideInfo
- Publication number
- CA1078397A CA1078397A CA254,482A CA254482A CA1078397A CA 1078397 A CA1078397 A CA 1078397A CA 254482 A CA254482 A CA 254482A CA 1078397 A CA1078397 A CA 1078397A
- Authority
- CA
- Canada
- Prior art keywords
- methoxy
- ethyl
- pyrrolidylmethyl
- sulphamoyl
- salts
- 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.)
- Expired
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)
Abstract
ABSTRACT OF THE DISCLOSURE
There is provided a novel method for preparing N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl benzamide, its acid addition salts with pharmaceutically acceptable inor-ganic or organic acids and its quaternary ammonium salts, characterized in that an enamine of the general formula:
wherein R1 represents an organic group, and R2 represents an acyl group, or salts thereof, is reacted with a 2-methoxy-5-sulphamoyl benzoic acid or one of its reactive derivative.
The product prepared is an antiemetic.
There is provided a novel method for preparing N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl benzamide, its acid addition salts with pharmaceutically acceptable inor-ganic or organic acids and its quaternary ammonium salts, characterized in that an enamine of the general formula:
wherein R1 represents an organic group, and R2 represents an acyl group, or salts thereof, is reacted with a 2-methoxy-5-sulphamoyl benzoic acid or one of its reactive derivative.
The product prepared is an antiemetic.
Description
`- 1078397 The invention relates to a new method of preparing N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl benz-amide, its salts of addition with pharmaceutically acceptable inorganic or organic acids, and quaternary ammonium salts.
The benzamide thus prepared has antiemetic properties. `
The method of preparation according to the invention comprises making enamines of general formula (I) or their salts react on a 2-methoxy-5-sulphamoyl benzoic acid or one of its reactive derivatives, e.g. its acid chloride, as follows:
Rl-C=CH-R2 COOH
CH2 ~ , ~C1 + 2 2 ~ reactive derivative ;
CO~H-C~ ~
-> H2N02S--~I ,.
In the above formulae:
Rl represents an organic group and R2 represents an acyl group.
Suitable organic group for the term Rl may include, for example, an alkyl (e.g., methyl, ethyl, propyl, butyl, etc.) group and the like.
Suitable acyl group for the term R2 may include, for example, an alkanoyl (e.g., acetyl, propionyl, etc.) group, an alkoxycarbonyl (e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, etc.) group and the like.
1~78397 The starting compound may be prepared in accordance with the procedure disclosed in copending Application Ser. No.
254,483 filed June 9, 1976.
The following example is given to illustrate the invention without imposing any restrictions on it.
EXAMPLE
N~ ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl -- benzamide .
5.26 g (0.02 mol) of hydrochloride of N-(l-ethyl-2-10 pyrrolidylmethyl)methyl-3-aminocrotonate and 200 ml of dichloroethane were placed in a one litre flask equipped with an agitator, a thermometer and a condenser.
The mixture was heated until the solids dissolved, then a hot solution of 5 g (0.02 mol) of chloride of 2- `
methoxy-5-sulphamoyl benzoic acid in 200 ml of dichloroethane was poured into it in a fine stream. The reaction mixture was ~;
brought to the boil over 6 hours. After about ten minutes ., crystals appeared. The mixture was allowed to cool and left' to stand overnight. The precipitate formed was filtered, 20 dissolved hot in an aqueous solution of hydrochloric acid, filtered on charcoal and the solution was made alkaline with ammonia. The crystals formed were filtered, washed with water and dried in a stove at 50C.
3.7 g of N-(l-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl benzamide was obtained (yield 54.2%, M.P. 178C).
.
~:
.,,.,~ .
~ ,,
The benzamide thus prepared has antiemetic properties. `
The method of preparation according to the invention comprises making enamines of general formula (I) or their salts react on a 2-methoxy-5-sulphamoyl benzoic acid or one of its reactive derivatives, e.g. its acid chloride, as follows:
Rl-C=CH-R2 COOH
CH2 ~ , ~C1 + 2 2 ~ reactive derivative ;
CO~H-C~ ~
-> H2N02S--~I ,.
In the above formulae:
Rl represents an organic group and R2 represents an acyl group.
Suitable organic group for the term Rl may include, for example, an alkyl (e.g., methyl, ethyl, propyl, butyl, etc.) group and the like.
Suitable acyl group for the term R2 may include, for example, an alkanoyl (e.g., acetyl, propionyl, etc.) group, an alkoxycarbonyl (e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, etc.) group and the like.
1~78397 The starting compound may be prepared in accordance with the procedure disclosed in copending Application Ser. No.
254,483 filed June 9, 1976.
The following example is given to illustrate the invention without imposing any restrictions on it.
EXAMPLE
N~ ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl -- benzamide .
5.26 g (0.02 mol) of hydrochloride of N-(l-ethyl-2-10 pyrrolidylmethyl)methyl-3-aminocrotonate and 200 ml of dichloroethane were placed in a one litre flask equipped with an agitator, a thermometer and a condenser.
The mixture was heated until the solids dissolved, then a hot solution of 5 g (0.02 mol) of chloride of 2- `
methoxy-5-sulphamoyl benzoic acid in 200 ml of dichloroethane was poured into it in a fine stream. The reaction mixture was ~;
brought to the boil over 6 hours. After about ten minutes ., crystals appeared. The mixture was allowed to cool and left' to stand overnight. The precipitate formed was filtered, 20 dissolved hot in an aqueous solution of hydrochloric acid, filtered on charcoal and the solution was made alkaline with ammonia. The crystals formed were filtered, washed with water and dried in a stove at 50C.
3.7 g of N-(l-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl benzamide was obtained (yield 54.2%, M.P. 178C).
.
~:
.,,.,~ .
~ ,,
Claims (2)
1. A method for preparing N-(1-ethyl-2-pyrrolidyl-methyl)-2-methoxy-5-sulphamoyl benzamide, its acid addition salts with pharmaceutically acceptable inorganic or organic acids and its quaternary ammonium salts, characterized in that an enamine of the general formula:
wherein:
R1 represents an organic group, and R2 represents an acyl group, or salts thereof, is reacted with a 2-methoxy-5-sulphamoyl benzoic acid or one of its reactive derivatives.
wherein:
R1 represents an organic group, and R2 represents an acyl group, or salts thereof, is reacted with a 2-methoxy-5-sulphamoyl benzoic acid or one of its reactive derivatives.
2. The process of Claim 1, wherein N-(1-ethyl-2-pyrrolidylmethyl)methyl-3-aminocrotonate is reacted with 2-methoxy-5-sulphamoyl benzoic acid chloride to form the N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl benzamide.
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 |
|---|---|
| CA1078397A true CA1078397A (en) | 1980-05-27 |
Family
ID=9156603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,482A Expired CA1078397A (en) | 1975-06-17 | 1976-06-09 | Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamide |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS6016415B2 (en) |
| AT (1) | AT349457B (en) |
| CA (1) | CA1078397A (en) |
| DE (1) | DE2622999A1 (en) |
| FI (1) | FI761746A (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 IE116976A patent/IE43003B1/en unknown
- 1976-06-01 PT PT6516776A patent/PT65167B/en unknown
- 1976-06-01 AT AT399976A patent/AT349457B/en not_active IP Right Cessation
- 1976-06-09 CA CA254,482A patent/CA1078397A/en not_active Expired
- 1976-06-09 MX MX29476U patent/MX3581E/en unknown
- 1976-06-10 GB GB2411276A patent/GB1501771A/en not_active Expired
- 1976-06-14 JP JP7031576A patent/JPS6016415B2/en not_active Expired
- 1976-06-16 FI FI761746A patent/FI761746A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6016415B2 (en) | 1985-04-25 |
| PT65167B (en) | 1977-11-17 |
| JPS52262A (en) | 1977-01-05 |
| MX3581E (en) | 1981-03-19 |
| ATA399976A (en) | 1978-09-15 |
| DE2622999A1 (en) | 1976-12-30 |
| IE43003B1 (en) | 1980-12-03 |
| AT349457B (en) | 1979-04-10 |
| PT65167A (en) | 1976-07-01 |
| FR2314918B1 (en) | 1977-12-09 |
| FI761746A (en) | 1976-12-18 |
| GB1501771A (en) | 1978-02-22 |
| FR2314918A1 (en) | 1977-01-14 |
| IE43003L (en) | 1976-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |