JPS5839826B2 - Shinkinalolefinic acid aminoketone information - Google Patents

Shinkinalolefinic acid aminoketone information

Info

Publication number
JPS5839826B2
JPS5839826B2 JP47070266A JP7026672A JPS5839826B2 JP S5839826 B2 JPS5839826 B2 JP S5839826B2 JP 47070266 A JP47070266 A JP 47070266A JP 7026672 A JP7026672 A JP 7026672A JP S5839826 B2 JPS5839826 B2 JP S5839826B2
Authority
JP
Japan
Prior art keywords
aminoketone
formula
acid
group
novel
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
Application number
JP47070266A
Other languages
Japanese (ja)
Other versions
JPS4930336A (en
Inventor
純基 勝部
勝 中尾
紀久夫 笹島
勇 丸山
雅治 高山
圭一 小野
重成 片山
好博 田中
茂穂 稲葉
久夫 山本
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE792906D priority Critical patent/BE792906A/en
Priority claimed from JP46102854A external-priority patent/JPS5820956B2/en
Priority claimed from JP46102855A external-priority patent/JPS5812273B2/en
Priority to JP1616972A priority patent/JPS5544749B2/ja
Priority to JP1675272A priority patent/JPS5535390B2/ja
Priority to JP47043125A priority patent/JPS491530A/ja
Priority to JP47065208A priority patent/JPS4924932A/ja
Priority to JP47070266A priority patent/JPS5839826B2/en
Priority to JP47070265A priority patent/JPS5820957B2/en
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP47095720A priority patent/JPS4961130A/ja
Priority to DE19722265094 priority patent/DE2265094A1/en
Priority to DE19722265095 priority patent/DE2265095C2/en
Priority to DE19722261269 priority patent/DE2261269C3/en
Priority to GB5810472A priority patent/GB1407706A/en
Priority to FR7244857A priority patent/FR2163717B1/fr
Priority to SE7216411A priority patent/SE399707B/en
Priority to FI3573/72A priority patent/FI57933C/en
Priority to AU50231/72A priority patent/AU470861B2/en
Priority to CH578076A priority patent/CH593296A5/xx
Priority to AT1076272A priority patent/AT328444B/en
Priority to CH1839372A priority patent/CH589661A5/xx
Priority to NL7217236A priority patent/NL7217236A/xx
Priority to US316026A priority patent/US3922266A/en
Priority to HUSU000829 priority patent/HU168117B/hu
Publication of JPS4930336A publication Critical patent/JPS4930336A/ja
Priority to AT5875*#A priority patent/AT330176B/en
Priority to US05/600,119 priority patent/US4012515A/en
Priority to US05/600,118 priority patent/US4012514A/en
Publication of JPS5839826B2 publication Critical patent/JPS5839826B2/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Anesthesiology (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Description

【発明の詳細な説明】 本発明は一般式〔１〕 〔式中、Ｒ１はハロゲン原子を表わし。[Detailed description of the invention] The present invention is based on the general formula [1] [In the formula, R1 represents a halogen atom.

ルホリノ基もしくは式 で示される３−アザ−ビシクロ［３２２）ノ２ テン−３−イル基または以下に示す二級アミノ基のいず
れかを表わす。It represents a ruphorino group, a 3-aza-bicyclo[322)no2then-3-yl group shown by the formula, or a secondary amino group shown below.

（式中、Ｒ２はハロゲン原子またはトリフルオルメチル
基を意味する。(In the formula, R2 means a halogen atom or a trifluoromethyl group.

）（式中、Ｒ３はアリール基を意味する。) (wherein, R3 means an aryl group.

）〕で表わされる新規なるオレフィニックアミノケトン
誘導体の新規製造法に関する。)] This invention relates to a new method for producing a novel olefinic aminoketone derivative represented by

さら（こ詳しくは一般式ｒｎ） （式中、Ｒ１およびＡは先と同じ意味を有する。Sara (general formula rn for details) (wherein R1 and A have the same meanings as above.

）で表わされるブチノールアミン誘導体を酸化すること
を特徴とするゴ般式［１）で表わされる新規なるオレフ
ィニツクアミノケトン誘導体の新規製造法である。This is a novel method for producing a novel olefinic aminoketone derivative represented by general formula [1], which is characterized by oxidizing a butynolamine derivative represented by formula [1].

本発明方法の目的化合物である一般式１１）で表わされ
る化合物は新規なる骨格を有し、それ自体中枢神経抑制
作用、自律神経作用等の有用な薬理作用を有するととも
に、其の他の各種の中枢神経関与側合成における有用な
る中間体（こもなり得るものである。The compound represented by the general formula 11), which is the target compound of the method of the present invention, has a new skeleton and has useful pharmacological effects such as central nervous system depressant action and autonomic nervous action, as well as various other effects. It is a useful intermediate in central nervous system synthesis.

したがって、本発明の趣旨とするものは新規なる骨格に
して医薬的価値の高い一連の化合物群の新規製造法を提
供せんとするものである。Therefore, the purpose of the present invention is to provide a new method for producing a series of compounds having a novel skeleton and having high pharmaceutical value.

本発明方法は一般式〔■〕で表わされるブチノールアミ
ン誘導体のヒドロキシ基を酸化することにより達成され
るが、その酸化剤としては種々のものを用いることがで
き、その例としては二酸化マンガン、クロム酸、クロム
酸塩、マンガン酸塩、酸素、オゾン、ジメチルスルホキ
シド、過酸等が挙げられる。The method of the present invention is achieved by oxidizing the hydroxyl group of the butynolamine derivative represented by the general formula [■], and various oxidizing agents can be used, such as manganese dioxide, manganese dioxide, Examples include chromic acid, chromate, manganate, oxygen, ozone, dimethyl sulfoxide, peracid, and the like.

ざら（こアルミニウムイソプロポキサイドを用いるオツ
ペナウア酸化も可能である。Otzpenauer oxidation using aluminum isopropoxide is also possible.

反応は水または有機溶媒中、室温付近で行なうのが一般
的であるが適宜冷却または加温して反応を抑制または促
進させることができる。The reaction is generally carried out in water or an organic solvent at around room temperature, but the reaction can be suppressed or accelerated by cooling or heating as appropriate.

反応終了後は通常の有機化学実験の手法にしたがって目
的物を単離、精製することができる。After the reaction is completed, the target product can be isolated and purified according to conventional organic chemistry experimental techniques.

なお、本発明の原料化合物〔■〕および目的化合物〔１
〕は強い塩基性を有する化合物であるので、酸と反応し
その付加塩を形成することが可能である。In addition, the raw material compound [■] of the present invention and the target compound [1]
] is a compound with strong basicity, so it can react with acids to form addition salts thereof.

したがって、反応乃至後処理過程における液性条件に応
じて遊離塩基またはその酸付加塩のいずれかの型で存在
する。Therefore, it exists in either the form of a free base or its acid addition salt depending on the liquid conditions during the reaction or post-treatment process.

なお、遊離塩基として単離されたるものを所望に応じそ
の酸付加塩とすることも可能である。Note that it is also possible to convert what is isolated as a free base into its acid addition salt, if desired.

酸付加塩形成用の酸としては通常の無機酸、有機酸が用
いられる。As the acid for forming acid addition salts, ordinary inorganic acids and organic acids are used.

なお１本発明の原料化合物であるブチノールアミン誘導
体は本発明者等により初めて合成された新規化合物であ
るがその代表的合成経路としては以下のものが挙げられ
る。Note that the butynolamine derivative, which is the raw material compound of the present invention, is a new compound synthesized for the first time by the present inventors, and representative synthetic routes thereof include the following.

（式中、Ｒ１およびＡは先と同じ意味を有し、Ｘはハロ
ゲン原子を表わす。(In the formula, R1 and A have the same meanings as above, and X represents a halogen atom.

）以下に本発明方法を具体的に説明する為に代表的な実
施例を記載するが、本発明方法はもとよりこれに限定さ
れない。) Below, typical examples will be described to specifically explain the method of the present invention, but the method of the present invention is not limited thereto.

実施例 １ Ｎ−Ｃ４’−（パラ−フルオルフェニル）−４′−ヒド
ロキシ−２′−トランス−ブテニル）−３−アザ−ビシ
クロＣ３２２）ノナン１．１５ｇを９ クロロホルム７０ｍ１中、活性二酸化マンガン１０ｇと
室温にて５時間攪拌し反応させた。Example 1 1.15 g of N-C4'-(para-fluorophenyl)-4'-hydroxy-2'-trans-butenyl)-3-aza-bicycloC322) nonane 10 g of activated manganese dioxide in 9 70 ml of chloroform The mixture was stirred and reacted at room temperature for 5 hours.

不溶物を戸別し、酒液を濃縮すると目的のＮ−Ｃ４′−
Ｃパラ−フルオルフェニル） 、ｉ／−オキソ−２’
−ブテニルツー３−アザ−ビシクロ〔３，２，２）ノナ
ンの淡黄色の針状結晶を０．８θ得た。After removing the insoluble matter and concentrating the liquor, the desired N-C4'-
C para-fluorophenyl), i/-oxo-2'
Pale yellow needle-shaped crystals of -butenyl-3-aza-bicyclo[3,2,2)nonane at 0.8θ were obtained.

融点；５０〜５１，５°Ｃ 赤外吸収スペクトル（ペースト法）；２８００〜２７５
０ １６７０゜ １６２０ １６００ １５１０゜ フ ツ １４１０ １２７０ １２４０゜ ９ １１６０ｃｒｆＬ−１ 核磁気共鳴スペクトル（ＣＤＣＡｓ ） ； ８．０（
２Ｈ，ｒｎ）。Melting point: 50-51,5°C Infrared absorption spectrum (paste method): 2800-275
0 1670゜1620 1600 1510゜futsu1410 1270 1240゜9 1160crfL-1 Nuclear magnetic resonance spectra (CDCAs); 8.0 (
2H, rn).

７．０〜７．３ （４Ｈ，ｍ） 、 ３．３（２Ｈ，ｍ
）、２．６５（４Ｈ，ｍ） なお、Ｈは水素数を表わし１ｍは多重線シグナルを表わ
しまた化学シフトはδ値（ＴＭＳよりのｐｐｍ値）で表
わされる。7.0-7.3 (4H, m), 3.3 (2H, m
), 2.65 (4H, m) Note that H represents the number of hydrogens, 1m represents a multiplet signal, and the chemical shift is represented by a δ value (ppm value from TMS).

紫外部吸収（λ極大ＣＨ３０Ｈ） ；２５６ ｒｎ μ
実施例 ２ Ｎ−Ｃ４’（パラ−クロールフェニル）４７−ヒドロキ
シ−２′−トランス−ブテニルヨーモルホリン０，９ｇ
をクロロホルム２５ｍ１中、活性二酸化マンガン８ｇと
１０時間、室温（こて攪拌し反応させた。Ultraviolet absorption (λ maximum CH30H); 256 rn μ
Example 2 N-C4' (para-chlorphenyl) 47-hydroxy-2'-trans-butenylyomorpholine 0.9 g
was reacted with 8 g of activated manganese dioxide in 25 ml of chloroform at room temperature (with stirring using a trowel) for 10 hours.

常法どおり後処理すると目的のＮ−Ｃ４’−（パラ−ク
ロールフェニル）−４′−オキソ−２′−ブテニルヨー
モルホリンを油状物質として０．８ｇ得た。After post-treatment in a conventional manner, 0.8 g of the target N-C4'-(para-chlorophenyl)-4'-oxo-2'-butenylyomorpholine was obtained as an oily substance.

赤外吸収スペクトル（フィルム法）；２９５０゜２９０
０ ２８００ ２７５０゜ ９ １６７０ １６２０ １５９０゜ ツ ツ １２８５ １２６５ １１１０゜ ９ １０９０ １００５ ｃｒｎ ’ ツ 実施例 ３ １−〔４’−（パラ−フルオルフェニル）−４′−ヒド
ロキシ−２′−トランス−ブテニル〕−４（パラ−クロ
ールフェニル）−４−ヒドロキシピペリジン１．０ｇを
クロロホルム中、活性二酸化マンガン８ｇと４．５時間
室温にて攪拌し反応させた。Infrared absorption spectrum (film method); 2950°290
0 2800 2750゜9 1670 1620 1590゜Tsu 1285 1265 1110゜9 1090 1005 crn' Example 3 1-[4'-(para-fluorophenyl)-4'-hydroxy-2'-trans-butenyl] 1.0 g of -4(para-chlorphenyl)-4-hydroxypiperidine was stirred and reacted with 8 g of activated manganese dioxide in chloroform at room temperature for 4.5 hours.

常法通り後処理することにより、目的の１−Ｃ４’−（
パラ−フルオルフェニル）−４’−オキ’／ −２’−
ｊテニル）−４−（パラ−クロールフェニル）−４−ヒ
ドロキシ−ピペリジンを結晶性物質として０．９ｇを得
た。The desired 1-C4'-(
para-fluorophenyl)-4'-oki'/-2'-
0.9 g of j-tenyl)-4-(para-chlorphenyl)-4-hydroxy-piperidine was obtained as a crystalline substance.

融点：１１１．５〜１１３°Ｃ 赤外吸収スペクトル（ペースト法）：３１５０゜１６６
０ １６１０ １５９５゜ ９ ν １３４０ １２７５ １２４０゜ クツ １１５０ １１２５゜ ツ １０４０ｃＩＩＬ−１ 核磁気共鳴スペクト／Ｌ／（ＣＤＣＡ３）：８．０（２
Ｈ，ｍ）。Melting point: 111.5-113°C Infrared absorption spectrum (paste method): 3150°166
0 1610 1595° 9 ν 1340 1275 1240° 1150 1125° 1040cIIL-1 Nuclear magnetic resonance spectrum/L/(CDCA3): 8.0(2
H, m).

７．５〜７．０ （６Ｈ，ｍ） ｊ ３．３５（４Ｈ，ｍ） 紫外吸収スペクトル（λ極大ＥｔｏＨ）：２５３ｍμ実
施例 ４ １−〔４′−（パラ−フルオルフェニル）−４′ヒドロ
キシ−２′−トランス−ブテニル）−４−（オルソ−メ
トキシフェニル）−ピペラジン０．１０．９をクロロホ
ルム中、活性二酸化マンガンｏ、 ｓ ｙと水冷下２時
間攪拌し反応させた。7.5-7.0 (6H, m) j 3.35 (4H, m) Ultraviolet absorption spectrum (λ maximum EtoH): 253 mμ Example 4 1-[4'-(para-fluorophenyl)-4' 0.10.9 of hydroxy-2'-trans-butenyl)-4-(ortho-methoxyphenyl)-piperazine was stirred and reacted with activated manganese dioxide o, sy in chloroform for 2 hours under water cooling.

常法通り後処理して目的の１−１４′−（パラ−フルオ
ルフェニル） 、ｉ／−オキソ−２’−−ｊテニル）
−４−（オルソ−メトキシフェニル）−ピペラジンを白
色針状結晶として得た。After treatment in a conventional manner, the desired 1-14'-(para-fluorophenyl), i/-oxo-2'--jtenyl)
-4-(ortho-methoxyphenyl)-piperazine was obtained as white needles.

融点８９．５〜９１．５℃ 赤外吸収スペクトル（ペース）法）：２８００゜２７５
０１６８０ １６３０゜ ツ ツ １５９５ １５００１２７０゜ ９ １２５０ １２３０゜ ツ 一０２５ｃｍ−１ 紫外吸収（λ極大ＥｔｏＨ） ： ２５１ ｍμ実施例
５ 実施例１と同様な方法により、次の化合物を得た。Melting point: 89.5-91.5°C Infrared absorption spectrum (Pace method): 2800°275
01680 1630° 1595 1500 1270° 9 1250 1230° 025 cm −1 Ultraviolet absorption (λ maximum EtoH): 251 mμ Example 5 The following compound was obtained in the same manner as in Example 1.

１−Ｃ４−（フルオルフェニル）−４−オキソ２−ブテ
ニルツー４−ヒドロキシ−４−（ｍトリフルオルメチル
フェニル）ピペリジン融点：９７〜９７．５℃1-C4-(fluorophenyl)-4-oxo2-butenyl-4-hydroxy-4-(mtrifluoromethylphenyl)piperidine Melting point: 97-97.5°C

Claims (1)

【特許請求の範囲】 １一般式 〔式中、Ｒ１はハロゲン原子を表わし。 ルホリノ基もしくは式 で示される３−アザ−ビシクロ〔３，２，２）ノナン−
３−イル基または以下（こ示す二級アミノ基のいずれか
を表わす。 （式中、Ｒ２はハロゲン原子またはトリフルオルメチル
基を意味する。 ）、（式中、Ｒ３はアリール基を意味する。 ）〕で表わされる新規ブチノールアミン誘導体を酸化す
ることを特徴とする一般式 （式中、Ｒ１およびＡは先と同じ意味を有する。 ）で表わされる新規なるオレフイニツクアミノケトン誘
導体の新規製造法。[Claims] General formula 1 [wherein R1 represents a halogen atom]. Ruphorino group or 3-aza-bicyclo[3,2,2)nonane-
3-yl group or the following (represents any of the secondary amino groups shown above. (In the formula, R2 means a halogen atom or a trifluoromethyl group.), (In the formula, R3 means an aryl group. )] A novel production of a novel olefinic aminoketone derivative represented by the general formula (wherein R1 and A have the same meanings as above), characterized by oxidizing a novel butynolamine derivative represented by Law.
JP47070266A 1971-12-18 1972-07-12 Shinkinalolefinic acid aminoketone information Expired JPS5839826B2 (en)

Priority Applications (25)

Application Number Priority Date Filing Date Title
BE792906D BE792906A (en) 1971-12-18 ARYL-KETONES AND THEIR PREPARATION
JP1616972A JPS5544749B2 (en) 1971-12-18 1972-02-15
JP1675272A JPS5535390B2 (en) 1971-12-18 1972-02-17
JP47043125A JPS491530A (en) 1971-12-18 1972-04-28
JP47065208A JPS4924932A (en) 1971-12-18 1972-06-28
JP47070266A JPS5839826B2 (en) 1971-12-18 1972-07-12 Shinkinalolefinic acid aminoketone information
JP47070265A JPS5820957B2 (en) 1971-12-18 1972-07-12 Synthetic butenolamine
JP47095720A JPS4961130A (en) 1971-12-18 1972-09-22
DE19722265094 DE2265094A1 (en) 1971-12-18 1972-12-14 1- (4-PHENYL-4-OXO-2-BUTENYL) PIPERIDINE DERIVATIVES
DE19722265095 DE2265095C2 (en) 1971-12-18 1972-12-14 "1- [4- (p-Fluorophenyl) -4-oxo-2-butenyl] -4- (o-methoxyphenyl) -piperazine and its salts with acids and medicinal products containing these compounds"
DE19722261269 DE2261269C3 (en) 1971-12-18 1972-12-14 1- [4- (p-Fluorophenyl) -4-oxo-2-butenyl] -4-phenyl-4-hydroxypiperidine derivatives
SE7216411A SE399707B (en) 1971-12-18 1972-12-15 ANALOGICAL PROCEDURE FOR THE PRODUCTION OF OLEFINARYLYKETONE
FI3573/72A FI57933C (en) 1971-12-18 1972-12-15 FRAMEWORK FOR ACTIVATION OF THERAPEUTIC ACTIVITIES OLEFINA ARYLKETONER
GB5810472A GB1407706A (en) 1971-12-18 1972-12-15 Production of aryl ketones and pharmaceutically active intermediates
FR7244857A FR2163717B1 (en) 1971-12-18 1972-12-15
AU50231/72A AU470861B2 (en) 1971-12-18 1972-12-18 Aryl ketones and production thereof
CH578076A CH593296A5 (en) 1971-12-18 1972-12-18
AT1076272A AT328444B (en) 1972-07-12 1972-12-18 Process for the production of new aryl ketones and their acidic addition salts
CH1839372A CH589661A5 (en) 1971-12-18 1972-12-18
NL7217236A NL7217236A (en) 1971-12-18 1972-12-18
US316026A US3922266A (en) 1972-06-28 1972-12-18 Aryl ketones and production thereof
HUSU000829 HU168117B (en) 1972-07-12 1972-12-18
AT5875*#A AT330176B (en) 1971-12-18 1975-01-07 METHOD FOR MANUFACTURING ARYL KETONES
US05/600,118 US4012514A (en) 1972-06-28 1975-07-29 Aryl ketones and production thereof
US05/600,119 US4012515A (en) 1972-06-28 1975-07-29 Aryl ketones and production thereof

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
JP46102855A JPS5812273B2 (en) 1971-12-18 1971-12-18 Shinki Acetylene Alcohol Usage No Shinki Seizouhou
JP46102854A JPS5820956B2 (en) 1971-12-18 1971-12-18 Shinkinal Acetylene Ketone Synthesis
JP1616972A JPS5544749B2 (en) 1971-12-18 1972-02-15
JP1675272A JPS5535390B2 (en) 1971-12-18 1972-02-17
JP47043125A JPS491530A (en) 1971-12-18 1972-04-28
JP47065208A JPS4924932A (en) 1971-12-18 1972-06-28
JP47070265A JPS5820957B2 (en) 1971-12-18 1972-07-12 Synthetic butenolamine
JP47070266A JPS5839826B2 (en) 1971-12-18 1972-07-12 Shinkinalolefinic acid aminoketone information
JP47095720A JPS4961130A (en) 1971-12-18 1972-09-22

Publications (2)

Publication Number Publication Date
JPS4930336A JPS4930336A (en) 1974-03-18
JPS5839826B2 true JPS5839826B2 (en) 1983-09-01

Family

ID=27576674

Family Applications (7)

Application Number Title Priority Date Filing Date
JP1616972A Expired JPS5544749B2 (en) 1971-12-18 1972-02-15
JP1675272A Expired JPS5535390B2 (en) 1971-12-18 1972-02-17
JP47043125A Pending JPS491530A (en) 1971-12-18 1972-04-28
JP47065208A Pending JPS4924932A (en) 1971-12-18 1972-06-28
JP47070265A Expired JPS5820957B2 (en) 1971-12-18 1972-07-12 Synthetic butenolamine
JP47070266A Expired JPS5839826B2 (en) 1971-12-18 1972-07-12 Shinkinalolefinic acid aminoketone information
JP47095720A Pending JPS4961130A (en) 1971-12-18 1972-09-22

Family Applications Before (5)

Application Number Title Priority Date Filing Date
JP1616972A Expired JPS5544749B2 (en) 1971-12-18 1972-02-15
JP1675272A Expired JPS5535390B2 (en) 1971-12-18 1972-02-17
JP47043125A Pending JPS491530A (en) 1971-12-18 1972-04-28
JP47065208A Pending JPS4924932A (en) 1971-12-18 1972-06-28
JP47070265A Expired JPS5820957B2 (en) 1971-12-18 1972-07-12 Synthetic butenolamine

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP47095720A Pending JPS4961130A (en) 1971-12-18 1972-09-22

Country Status (9)

Country Link
JP (7) JPS5544749B2 (en)
AU (1) AU470861B2 (en)
BE (1) BE792906A (en)
CH (2) CH593296A5 (en)
FI (1) FI57933C (en)
FR (1) FR2163717B1 (en)
GB (1) GB1407706A (en)
NL (1) NL7217236A (en)
SE (1) SE399707B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50140451A (en) * 1974-04-16 1975-11-11
JPS5116677A (en) * 1974-07-29 1976-02-10 Sumitomo Chemical Co SHINKINABUCHIROFUENONJUDOTAI OYOBI SONOSANFUKAENNOSEIHO
JPS5283863U (en) * 1975-12-13 1977-06-22
JPS5324020A (en) * 1976-08-14 1978-03-06 Kumiai Chem Ind Co Ltd Composition for herbicide
JPS5498755A (en) * 1978-01-13 1979-08-03 Sumitomo Chem Co Ltd Novel butenophenone derivative
CA1151164A (en) * 1978-01-13 1983-08-02 Atsuyuki Kojima Conjugated ketone compounds and their production and use
JPS55116000U (en) * 1979-02-10 1980-08-15
US4728659A (en) * 1984-06-27 1988-03-01 Ss Pharmaceutical Co., Ltd. Aminomethyl derivatives and preparation process thereof as well as platelet aggregation inhibitors containing same
US5244902A (en) * 1989-08-21 1993-09-14 Beth Israel Hospital Association Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses
US5703088A (en) * 1989-08-21 1997-12-30 Beth Israel Deaconess Medical Center, Inc. Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses
WO1991013622A1 (en) * 1990-03-16 1991-09-19 Beth Israel Hospital Association Use of spiperone as an immunosuppressant and anti-inflammatory agent
US5693645A (en) * 1992-12-23 1997-12-02 Beth Israel Deaconess Medical Center, Inc. Use of spiperone or spiperone derivatives as immunosuppressant agents
US11707027B2 (en) 2019-12-02 2023-07-25 Fork Farms Holdings, Llc Hydroponic grow assembly

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK131147B (en) * 1969-10-27 1975-06-02 Sumitomo Chemical Co Process for the preparation of butyrophenone derivatives or acid addition salts thereof.
BE758380A (en) * 1969-11-04 1971-04-16 Sumitomo Chemical Co PROCESS FOR PREPARATION OF ARYL-KETON DERIVATIVES

Also Published As

Publication number Publication date
SE399707B (en) 1978-02-27
FR2163717B1 (en) 1977-07-15
JPS4924932A (en) 1974-03-05
NL7217236A (en) 1973-06-20
JPS4930336A (en) 1974-03-18
JPS4885569A (en) 1973-11-13
CH593296A5 (en) 1977-11-30
FI57933B (en) 1980-07-31
FI57933C (en) 1980-11-10
BE792906A (en) 1973-06-18
CH589661A5 (en) 1977-07-15
AU5023172A (en) 1974-06-20
JPS4930335A (en) 1974-03-18
GB1407706A (en) 1975-09-24
JPS4881854A (en) 1973-11-01
JPS5544749B2 (en) 1980-11-13
JPS491530A (en) 1974-01-08
FR2163717A1 (en) 1973-07-27
JPS5535390B2 (en) 1980-09-12
JPS5820957B2 (en) 1983-04-26
JPS4961130A (en) 1974-06-13
AU470861B2 (en) 1974-06-20

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