JPS5946214B2 - Production method of aminoketone derivatives - Google Patents
Production method of aminoketone derivativesInfo
- Publication number
- JPS5946214B2 JPS5946214B2 JP50065079A JP6507975A JPS5946214B2 JP S5946214 B2 JPS5946214 B2 JP S5946214B2 JP 50065079 A JP50065079 A JP 50065079A JP 6507975 A JP6507975 A JP 6507975A JP S5946214 B2 JPS5946214 B2 JP S5946214B2
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- formulas
- general formula
- tables
- phenyl
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
【発明の詳細な説明】
本発明は一般式
で表わされる化合物またはその塩の製造法に関するもの
であり、これら新規化合物は降圧、鎮痛、消炎、向精神
作用等を有し、医薬として有用である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a compound represented by the general formula or a salt thereof, and these novel compounds have antihypertensive, analgesic, antiinflammatory, and psychotropic effects, and are useful as medicines. .
上記式中のＡは炭素数２〜５の直鎖または分枝アルキレ
ンを、Ｗは−Ｎ（Ｒ２）（Ｒ３）（Ｒ２は水素、低級ア
ルキルを、Ｒ３は低級アルカノイル、ベンゾイルを示す
。In the above formula, A represents a straight chain or branched alkylene having 2 to 5 carbon atoms, W represents -N(R2)(R3) (R2 represents hydrogen or lower alkyl, and R3 represents lower alkanoyl or benzoyl).
）または−ＯＲ４（Ｒ４は低級アルキル、低級アルカノ
イル、ベンゾイルを示す。）を、Ｒ１は水素、低級アル
キルを、Ｒ５、Ｒ６は一方が水素、低級アルキルで、他
方が低級アルキルを示し、あるいは隣接する窒素原子と
共にピペリジノ、４−カルパモイル一４−ピペリジノピ
ペリジ人 ４−ヒドロキシ−４−（ｐ−トリル）ピペリ
ジ八４一置換−１−ピペラジニル（置換基は低級アル午
ル、ヒドロキシ低級アルキル、フエニル、ハロフエニル
、低級アルキルフエニル、低級アルコ午ジフェニル、ピ
リジル、１−フエニル一２−イミダゾリルメチルの中か
ら任意に選ばれ伐）を形成する基を示す。上記各記号の
定義において、アル牛レンとしてはたとえばエチレン、
トリメチレン、プロピレン、テトラメチレン、ペンタメ
チレンが、低級アルキルとしてはたとえばメチル、エチ
ル、プロピルが、低級アルコキシとしてはたとえばメト
キシ、エトキシが、ハロデンとしてはたとえばフツ素、
塩素、臭素が、低級アルカノイルとしそはたとえばアセ
チルが挙げられる。) or -OR4 (R4 represents lower alkyl, lower alkanoyl, benzoyl), R1 represents hydrogen or lower alkyl, R5 and R6, one of which is hydrogen or lower alkyl and the other is lower alkyl, or adjacent Together with the nitrogen atom, piperidino, 4-carpamoyl, 4-piperidino, 4-hydroxy-4-(p-tolyl)piperidyl, 4-substituted-1-piperazinyl (the substituents are lower alkyl, hydroxy lower alkyl, It represents a group arbitrarily selected from phenyl, halophenyl, lower alkyl phenyl, lower alkyl diphenyl, pyridyl, and 1-phenyl-2-imidazolylmethyl. In the definitions of each symbol above, examples of alkylene include ethylene,
Examples of lower alkyl include trimethylene, propylene, tetramethylene, and pentamethylene; examples of lower alkyl include methyl, ethyl, and propyl; examples of lower alkoxy include methoxy and ethoxy; and examples of halodane include fluorine,
Examples include chlorine, bromine, lower alkanoyl, and acetyl.
本発明によれば一般式〔１〕で表わされる化合物は、一
般式
〔式中のＺは塩素、臭素等のハロデンを示し、その他の
記号は前記と同義である。According to the present invention, the compound represented by the general formula [1] is a compound represented by the general formula [In the formula, Z represents halodene such as chlorine or bromine, and the other symbols have the same meanings as above.
〕で表わされる化合物と一般式
〔式中のＲ５，Ｒ６は前記のものと同義であるＪで表わ
される化合物を反応させることにより製造される。It is produced by reacting a compound represented by the following formula with a compound represented by the general formula J, in which R5 and R6 have the same meanings as above.
反応溶媒として（Ｊ／タノール、エタノール、ベンゼン
、トルエン、テトラヒドロフラン、ジメチルホルムアミ
ド等が用いられ、反応温度は室温〜１５０℃が適当であ
る。As the reaction solvent, (J/tanol, ethanol, benzene, toluene, tetrahydrofuran, dimethylformamide, etc.) are used, and the reaction temperature is suitably from room temperature to 150°C.
また脱酸剤としてピリジン、トリエチルアミン、重ソウ
、炭酸カリウム等を用いると反応は収Ｔよく殻時間で完
了する。かくして得られる一般式（１）で表わされる化
合物は塩形成の常法により塩酸、硫酸等と無機酸塩を、
マロン酸、フマール酸等と有機酸塩を形成することがで
きる。一般式（１）で表わされる化合物は可能なすべて
の立体異性体およびその混合物を含むものである。Further, when pyridine, triethylamine, sodium sulfur, potassium carbonate, etc. are used as a deoxidizing agent, the reaction is completed with good T yield and within a shell time. The compound represented by the general formula (1) obtained in this way is prepared by combining an inorganic acid salt with hydrochloric acid, sulfuric acid, etc. by a conventional salt formation method.
It can form organic acid salts with malonic acid, fumaric acid, etc. The compound represented by general formula (1) includes all possible stereoisomers and mixtures thereof.
また分子内に不斉炭素を有する化合物は通常よく知られ
た方法により光学的に活性なエナンチオマ一に分割する
ことができる。以下に実施例を挙げて本発明を更に具体
的に説明する。Compounds having asymmetric carbon atoms in their molecules can usually be separated into optically active enantiomers by well-known methods. The present invention will be explained in more detail with reference to Examples below.
実施例 １
４′−（２′−アセタミドエチル）−２−クロロアセト
フエノン２３ｇ１エタノール６０ｍ１，、トリエチルア
ミン１２．１ｇ、ピペリジン９．４ｇの混合物を一晩室
温で放置する。Example 1 A mixture of 23 g of 4'-(2'-acetamidoethyl)-2-chloroacetophenone, 60 ml of ethanol, 12.1 g of triethylamine, and 9.4 g of piperidine is left overnight at room temperature.
エタノールを減圧にて留去し、残査に水を加え、析出す
る結晶を戸取する。水洗後ベンゼンから再結晶すれば、
融点８７〜９０℃の４′−（２−アセタミドエチル）−
２−ピペリジノアセトフエノン１２．４ｇが無色結晶と
して得られる。実施例 ２
４′−（３−アセトキシプロピル）−２−クロロアセト
フエノン２０ｇ１エタノール７０ＷＬｅ１トリエチルア
ミン９．７ｇ、４−（０−トリル）ピペラジン１５．５
ｇの混合物を室温で一晩放置する。Ethanol is distilled off under reduced pressure, water is added to the residue, and the precipitated crystals are collected. If you recrystallize from benzene after washing with water,
4'-(2-acetamidoethyl)- with a melting point of 87-90°C
12.4 g of 2-piperidinoacetophenone are obtained as colorless crystals. Example 2 4'-(3-acetoxypropyl)-2-chloroacetophenone 20g1 ethanol70WLe1 triethylamine 9.7g, 4-(0-tolyl)piperazine 15.5g
Let the mixture of g stand at room temperature overnight.
Claims (1)
を、Ｗは−Ｎ（Ｒ＾２）（Ｒ＾３）（Ｒ＾２は水素、低
級アルキルを、Ｒ＾３は低級アルカノイル、ベンゾイル
を示す。 ）または−ＯＲ＾４（Ｒ＾４は低級アルキル、低級アル
カノイル、ベンゾイルを示す。）を、Ｒ＾１は水素、低
級アルキルを、Ｚはハロゲンを示す。〕で表わされる化
合物と一般式 ▲数式、化学式、表等があります▼ 〔式中のＲ＾５，Ｒ＾６は一方が水素、低級アルキルで
、他方が低級アルキルを示し、あるいは隣接する窒素原
子と共にピベリジノ、４−カルバモイル−４−ピペリジ
ノピペリジノ、４−ヒドロキシ−４−（ｐ−トリル）ピ
ペリジノ、４−置換−１−ピペラジニル（置換基は低級
アルキル、ヒドロキシ低級アルキル、フェニル、ハロフ
エニル、低級アルキルフェニル、低級アルコキシフェニ
ル、ピリジル、１−フエニル−２−イミダゾリルメチル
の中から任意に選ばれる。 ）を形成する基を示す。〕で表わされる化合物を反応さ
せるこことを特徴とする一般式▲数式、化学式、表等が
あります▼ 〔式中の各記号は前記のものと同義である。 〕で表わされる化合物またはその塩の製造法。[Claims] 1. General formula ▲ Numerical formulas, chemical formulas, tables, etc. ^3) (R^2 represents hydrogen, lower alkyl, R^3 represents lower alkanoyl, benzoyl) or -OR^4 (R^4 represents lower alkyl, lower alkanoyl, benzoyl), R ^1 represents hydrogen or lower alkyl, and Z represents halogen. ] There are compounds represented by the general formula ▲ mathematical formulas, chemical formulas, tables, etc. and piperidino, 4-carbamoyl-4-piperidinopiperidino, 4-hydroxy-4-(p-tolyl)piperidino, 4-substituted-1-piperazinyl (substituents are lower alkyl, hydroxy lower alkyl, phenyl, halophenyl) , lower alkylphenyl, lower alkoxyphenyl, pyridyl, and 1-phenyl-2-imidazolylmethyl. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting compounds represented by ▼ [Each symbol in the formula has the same meaning as above. ] or a method for producing a salt thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50065079A JPS5946214B2 (en) | 1975-05-29 | 1975-05-29 | Production method of aminoketone derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50065079A JPS5946214B2 (en) | 1975-05-29 | 1975-05-29 | Production method of aminoketone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51141831A JPS51141831A (en) | 1976-12-07 |
| JPS5946214B2 true JPS5946214B2 (en) | 1984-11-10 |
Family
ID=13276576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50065079A Expired JPS5946214B2 (en) | 1975-05-29 | 1975-05-29 | Production method of aminoketone derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5946214B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6490708A (en) * | 1987-10-02 | 1989-04-07 | Yasuo Kakiuchi | Melting and solidifying device for plastic waste material |
| JPH0390912U (en) * | 1989-12-28 | 1991-09-17 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2569193B2 (en) * | 1984-08-20 | 1987-01-16 | Lafon Labor | 1- (ACETYLAMINOPHENYL) -2-AMINO-PROPANONE DERIVATIVES, THEIR USE IN THERAPEUTICS AND THEIR PREPARATION PROCESS |
| JP2002540072A (en) * | 1999-03-03 | 2002-11-26 | メルク エンド カムパニー インコーポレーテッド | Inhibitors of prenyl protein transferase |
| US7601868B2 (en) | 2003-02-12 | 2009-10-13 | Takeda Pharmaceutical Company Limited | Amine derivative |
-
1975
- 1975-05-29 JP JP50065079A patent/JPS5946214B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6490708A (en) * | 1987-10-02 | 1989-04-07 | Yasuo Kakiuchi | Melting and solidifying device for plastic waste material |
| JPH0390912U (en) * | 1989-12-28 | 1991-09-17 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51141831A (en) | 1976-12-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6339868A (en) | Di (lower alkyl) phenol derivative | |
| JP2556722B2 (en) | Novel sulfonamide compound | |
| EP0255710A2 (en) | 1,4-Dihydropyridine derivatives with calcium agonist and alpha-1-antagonist activity | |
| JP3973941B2 (en) | Method for producing δ-aminopentadienoic acid ester derivative | |
| US6545037B2 (en) | Benzenesulfonamide compounds | |
| CS198297B2 (en) | Method of producing derivatives of urea | |
| JPS5946214B2 (en) | Production method of aminoketone derivatives | |
| BRPI0619019A2 (en) | process for making a compound, and, compound | |
| HU223476B1 (en) | New intermediates for the preparation of thiols | |
| NO130329B (en) | ||
| JPH0545587B2 (en) | ||
| SU718011A3 (en) | Method of producing phenylthieno-(2,3-c) piperidine derivatives or salts thereof | |
| HU220971B1 (en) | Process for producing 0-(3-amino-2-hidroxy-propyl)-hidroxim acid halogenids | |
| JPS5830312B2 (en) | Cinquinapyrazole sulfonamide middle ino | |
| JP2678758B2 (en) | Novel propane derivative | |
| JPS5939417B2 (en) | Method for producing amino alcohol derivatives | |
| JPH0350748B2 (en) | ||
| JPS5940149B2 (en) | Oxindole derivative | |
| JPS5925785B2 (en) | Novel carboxylic acid amide derivative | |
| JPS6053022B2 (en) | Pyridazinone derivative | |
| JPS6047264B2 (en) | Thiazolidine derivatives | |
| JPS625978A (en) | Production of 1,4-dihydropyridine derivative or salt thereof | |
| JPS61161263A (en) | Production of 1,4-dihydropyridine monoester monocarboxylic acid | |
| JPS5940148B2 (en) | Indolinthione derivative | |
| JPH037266A (en) | 2-(4-phenyl-1-piperazinylalkyl)amino-5-ethynylpyrimidine derivative, its intermediate and production thereof |