JPS6016415B2 - Method for producing N-substituted-2-methoxy-5-sulfamoylbenzamide or its salts - Google Patents
Method for producing N-substituted-2-methoxy-5-sulfamoylbenzamide or its saltsInfo
- Publication number
- JPS6016415B2 JPS6016415B2 JP51070315A JP7031576A JPS6016415B2 JP S6016415 B2 JPS6016415 B2 JP S6016415B2 JP 51070315 A JP51070315 A JP 51070315A JP 7031576 A JP7031576 A JP 7031576A JP S6016415 B2 JPS6016415 B2 JP S6016415B2
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- sulfamoylbenzamide
- salts
- group
- substituted
- 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)
Description
【発明の詳細な説明】
この発明はＮ−（１ーェチルー２−ピロリジニルメチル
）一２ーメトキシ−５−スルフアモイルベンズァミド、
またはその薬学的に許容される無機酸もしくは有機酸と
の付加塩、またはその第四アンモニウム塩の製造法に関
する。Detailed Description of the Invention This invention relates to N-(1-ethyl-2-pyrrolidinylmethyl)-12-methoxy-5-sulfamoylbenzamide,
or its addition salt with a pharmaceutically acceptable inorganic or organic acid, or its quaternary ammonium salt.
この発明による製造法は、下記反応式で表わされるよう
に、一般式（１）で示されるェナミンもしくはその塩に
、式（Ｄ）の２ーメトキシー５ースルフアモィル安息香
酸もしくはそのカルボキシ基における反応性誘導体を反
応させることからなるものである。The production method according to the present invention includes adding 2-methoxy-5-sulfamoylbenzoic acid of formula (D) or a reactive derivative thereof at the carboxy group to enamine or its salt represented by general formula (1), as shown in the following reaction formula. It consists of reacting.
［１］
もしくはその塩
［ｎ］
もしくはその力ルボキシ
基にお‘ナる反応性誘導体
Ｒ，はアルキル基、Ｒ２はアルコキシカルボニル基をそ
れぞれ表わす。[1] or a salt thereof [n] or a reactive derivative thereof corresponding to a carboxy group R, represents an alkyl group, and R2 represents an alkoxycarbonyl group, respectively.
Ｒ，として好ましいアルキル基の例としては、たとえば
メチル基、エチル基、プロピル基、ブチル基などが挙げ
られ、またＲ２として好ましいアルコキシカルボニル基
の例としては、メトキシカルボニル基、ェトキシカルボ
ニル基、プロポキシカルボニル基、ブトキシカルボニル
基などが挙げられる。Examples of alkyl groups preferable as R include methyl group, ethyl group, propyl group, butyl group, etc., and examples of alkoxycarbonyl groups preferable as R2 include methoxycarbonyl group, ethoxycarbonyl group, propoxy Examples include carbonyl group and butoxycarbonyl group.
この反応は、例えばジクロロェタンのようなこの反応に
悪影響を与えない溶媒中で行なわれることが多い。This reaction is often carried out in a solvent that does not adversely affect the reaction, such as dichloroethane.
この反応の温度は特に限定されず、反応剤、溶媒の種類
等により適宜選択される。The temperature of this reaction is not particularly limited, and is appropriately selected depending on the type of reactant, solvent, etc.
上記Ｎ−置換−２−メトキシ−５ースルフアモィルベン
ズアミドまたはその塩類の製造法はこの発明の主題とな
っている。The process for producing the above N-substituted-2-methoxy-5-sulfamoylbenzamide or its salts is the subject of this invention.
このペンズアミド譲導体は、それぞれ１９６８王４月１
日と１９６６王１月２１日に出願された仏国特許第４８
７則 Ｍ号ならびに同第５９１８Ｍ号において、本出願
人がすでに述べた通り、重要な薬学的性質を有するもの
である。この発明を具体的に説明するために、以下に実
施例を示すが、これはこの発明を限定するものではない
。実施例
Ｎ一（１ーエチル−２ーピロリジニルメチル）一２ーメ
トキシー５ースルフアモイルベンズアミド雛拝畿と温度
計と冷却器を備えた１タフラスコに、Ｎ一（１ーエチル
−２−ピロリジニルメチル）−３ーアミノクロトン酸メ
チルェステルの塩酸塩５．２能（０．０２モル）とジク
ｏｏェタン２００叫を入れた。This penzamide derivative was produced on April 1, 1968, respectively.
French Patent No. 48 filed on January 21, 1966
Rule 7 As already stated by the applicant in No. M and No. 5918M, it has important pharmaceutical properties. EXAMPLES Examples will be shown below to specifically explain this invention, but they are not intended to limit this invention. Example N1(1-Ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamoylbenzamide In a 1-tough flask equipped with a container, a thermometer, and a condenser, N1(1-ethyl-2-pyrrolidinylmethyl) was added. 5.2 moles (0.02 mol) of hydrochloride of methyl)-3-aminocrotonic acid ester and 200 moles of dichloromethane were added.
この混合物を、固体が溶解するまで加熱し、つづいてこ
れにジクロロエタン２００机上に２−メトキシー５−ス
ルフアモィル安息香酸クロラィド５ｇ（０．０２モル）
を溶かした熱溶液を、細い流れで注いだ。The mixture was heated until the solids dissolved and then 5 g (0.02 mol) of 2-methoxy-5-sulfamoylbenzoic acid chloride was added to 200 ml of dichloroethane.
A hot solution of was poured in a thin stream.
この反応混合物を６時間にわたって沸騰させた。約１び
分後に結晶が析出した。この混合物を放冷して、１夜放
置した。生じた沈殿を炉取し、塩酸水溶液に熱溶解し、
さらに活性炭を通して炉過し、この炉液をアンモニアで
アルカリ性にした。生じた結晶を炉取し、水洗し、乾燥
室中５０００で乾燥した。Ｎ一（１ーエチル−２−ピロ
リジニルメチル）一２−メトキシー５−スルフアモイル
ベンズアミド３．７ｇを得た（収率：５４．２％、融点
：１７８こＣ）。The reaction mixture was boiled for 6 hours. Crystals precipitated after about 1 minute. The mixture was allowed to cool and stand overnight. The resulting precipitate was collected in an oven and dissolved in a hydrochloric acid aqueous solution,
The mixture was further passed through a furnace through activated carbon, and the furnace liquid was made alkaline with ammonia. The resulting crystals were collected in a furnace, washed with water, and dried in a drying room at 5,000 ℃. 3.7 g of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamoylbenzamide was obtained (yield: 54.2%, melting point: 178 °C).
Claims (1)
ルボニル基をそれぞれ表わす。 ）で示されるエナミンもしくはその塩に、２−メトキシ
−５−スルフアモイル安息香酸もしくはそのカルボキシ
基における反応性誘導体を反応させて、Ｎ−（１−エチ
ル−２−ピロリジニルメチル）−２−メトキシ−５−ス
ルフアモイルベンズアミド、またはその薬学的に許容さ
れる無機酸もしくは有機酸との付加塩、またはその第四
アンモニウム塩を得ることを特徴とするＮ−置換−２−
メトキシ−５−スルフアモイルベンズアミドまたはその
塩類の製造法。[Claims] 1 Enamine or its salt represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 represents an alkyl group and R_2 represents an alkoxycarbonyl group, respectively.) 2-methoxy -5-sulfamoylbenzoic acid or its reactive derivative at the carboxy group to form N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulfamoylbenzamide or its pharmaceutically N-substituted-2- characterized by obtaining addition salts with acceptable inorganic or organic acids, or quaternary ammonium salts thereof.
A method for producing methoxy-5-sulfamoylbenzamide or its salts.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518824 | 1975-06-17 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| JPS52262A JPS52262A (en) | 1977-01-05 |
| JPS6016415B2 true JPS6016415B2 (en) | 1985-04-25 |
Family
ID=9156603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51070315A Expired JPS6016415B2 (en) | 1975-06-17 | 1976-06-14 | Method for producing N-substituted-2-methoxy-5-sulfamoylbenzamide or its salts |
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 AT AT399976A patent/AT349457B/en not_active IP Right Cessation
- 1976-06-01 PT PT65167A patent/PT65167B/en unknown
- 1976-06-01 IE IE1169/76A patent/IE43003B1/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 |
|---|---|
| FI761746A7 (en) | 1976-12-18 |
| ATA399976A (en) | 1978-09-15 |
| AT349457B (en) | 1979-04-10 |
| CA1078397A (en) | 1980-05-27 |
| FR2314918B1 (en) | 1977-12-09 |
| GB1501771A (en) | 1978-02-22 |
| DE2622999A1 (en) | 1976-12-30 |
| PT65167B (en) | 1977-11-17 |
| PT65167A (en) | 1976-07-01 |
| FR2314918A1 (en) | 1977-01-14 |
| IE43003L (en) | 1976-12-17 |
| JPS52262A (en) | 1977-01-05 |
| MX3581E (en) | 1981-03-19 |
| IE43003B1 (en) | 1980-12-03 |
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