JPS595588B2 - シンキナブチロフエノンユウドウタイ オヨビ ソノエン ノ セイホウ - Google Patents

シンキナブチロフエノンユウドウタイ オヨビ ソノエン ノ セイホウ

Info

Publication number
JPS595588B2
JPS595588B2 JP47058789A JP5878972A JPS595588B2 JP S595588 B2 JPS595588 B2 JP S595588B2 JP 47058789 A JP47058789 A JP 47058789A JP 5878972 A JP5878972 A JP 5878972A JP S595588 B2 JPS595588 B2 JP S595588B2
Authority
JP
Japan
Prior art keywords
acid
formula
yudoutai
synkinabutylofenon
sonoen
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
JP47058789A
Other languages
English (en)
Other versions
JPS4914477A (ja
Inventor
紀久雄 笹島
勝 中尾
勇 丸山
圭一 小野
重成 片山
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
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP47058789A priority Critical patent/JPS595588B2/ja
Priority to SE7307963A priority patent/SE397089B/xx
Priority to CH826373A priority patent/CH592624A5/xx
Priority to FR7320929A priority patent/FR2187346B1/fr
Priority to NL7308000A priority patent/NL7308000A/xx
Priority to GB2762773A priority patent/GB1414020A/en
Priority to CA173,679A priority patent/CA1023362A/en
Priority to HUSU819A priority patent/HU167380B/hu
Priority to DE2329813A priority patent/DE2329813A1/de
Priority to BE132163A priority patent/BE800791A/xx
Publication of JPS4914477A publication Critical patent/JPS4914477A/ja
Priority to US05/617,730 priority patent/US4009173A/en
Publication of JPS595588B2 publication Critical patent/JPS595588B2/ja
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

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

Description

【発明の詳細な説明】 本発明は新規なブチロフエノン誘導体およびその塩の製
法に関する。
さらに詳細に説明するならば、一般式〔Ｉ〕〔式中、Ｒ
，はＲ３ＣＯであられされるアシル基（ただし、Ｒ３は
低級アルキル基をあられす。
）を、Ｒ５はハロゲン原子を、ｚはＨ２または酸素原子
をあられす。〕であられされる新規なブチロフエノン誘
導体の製法に関する。
本発明によつて得られるこれらの新規な誘導体は、中枢
神経抑制作用、鎮痛作用を示しいわゆるメージヤ一 ・
トランキライザ一として有用であると共に、鎮静剤、消
炎剤などの中間体としてもきわめて有用なものである。
本発明はこのような有用な薬物を工業的に有利に製造す
る方法を提供することを目的としたものである。すなわ
ち、本発明は一般式几 〔式中、Ｒ３、Ｒ，およびｚは前述のとおりである。
〕であられされるインドール誘導体を酸化剤で酸化 ｊ
し、さらに必要に応じて酸で処理することによつて、前
記一般式〔Ｉ〕であられされる新規なブチロフエノン誘
導体およびその塩を製造する方法である。． 本発明に
おける酸化剤としては、たとえば、オゾン、過酸化水素
、過酸（たとえば過蟻酸、過酢 ４酸、過安息香酸）、
クロム酸、過マンガン酸カリウムなどが適当であるが、
もちろんこれらのみに限定されない。上記の方法で得ら
れるブチロフエノン誘導体は、酸、たとえば塩酸、硫酸
、リン酸、臭化水素酸、チオシアン酸、酢酸、プロピオ
ン酸、蓚酸、クエン酸、リンゴ酸、酒石酸、フマル酸、
マレイン酸、コ・・ク酸、グリコール酸、安息香酸、桂
皮酸、ｐ−アミノサルチル酸、サルチル酸、メタスルホ
ン酸、アスコルビン酸などと処理して酸付加塩とするこ
ともできる。
本発明において用いる出発物質、すなわち前記一般式で
あられされる化合物は、たとえば以下の方法によつて合
成される。
〔ただし式中、Ｒ３およびＲ５は前記のとおりで、Ｘは
ハロゲン原子をあられす。
〕本発明を更に詳しく述べるために以下に実施例をあげ
るが、これらはその一例にすぎず本発明は何らこれらに
限定されるものではない。
実施例 １ ２−メチル−３−〔γ−（４′−ピペリジノ一４′カル
バモイルーピペリジノ）プロピル〕−６フルオルインド
ールの塩酸塩５ｔを氷酢酸１４０ｍ１に溶かし、氷冷下
１００〜２０℃にてオゾンガスを導入すると、反応液は
徐々に着色し、赤色を帯びるが再びこの色は時間と共に
退色し、５０分後薄い黄色溶液となる。
これを１０％水酸化ナトリウム溶液でアルカリ性とし、
酢酸エチルにて抽出し、酢酸エチルを減圧乾固するとア
メ様物が得られる。これを塩酸のエタノール溶液で処理
すると２−アセトアミノ−４−フルオロ−ｒ−（４′ピ
ペリジノ一４′−カルバモイルーピペリジノ）−ブチロ
フエノンの塩酸塩を得る。融点２３３ノ〜２３８℃（分
解）実施例 ２ 実施例１とほぼ同様の方法により２−メチル３−〔γ−
（４１−ピペリジノ一４′−アミノメチルピペリジノ）
プロピル〕−６−フルオルインドールを酸化することに
より２−アセチルアミノ−４フルオル−ｒ−（４′−ピ
ペリジノ一４′−アミノメチルピペリジノ）−ブチロフ
エノン塩酸塩が得られた。

Claims (1)

  1. 【特許請求の範囲】 １ 一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿３は低級アルキル基を、Ｒ＿５はハロゲン
    原子を、ＺはＨ＿２または酸素原子をあらわす。 〕であらわされるインドール誘導体を酸化剤と処理し、
    さらに必要に応じて酸で処理する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、Ｒ＿５およびＺは前述のとおりである。 Ｒ＿１はＲ＿３ＣＯなるアシル基（ただしＲ＿３は前述
    のとおり）をあらわす。〕であらわされる新規なブチロ
    フェノン誘導体およびその塩の製法。
JP47058789A 1972-06-12 1972-06-12 シンキナブチロフエノンユウドウタイ オヨビ ソノエン ノ セイホウ Expired JPS595588B2 (ja)

Priority Applications (11)

Application Number Priority Date Filing Date Title
JP47058789A JPS595588B2 (ja) 1972-06-12 1972-06-12 シンキナブチロフエノンユウドウタイ オヨビ ソノエン ノ セイホウ
SE7307963A SE397089B (sv) 1972-06-12 1973-06-06 Forfarande for framstellning av butyrofenonderivat
CH826373A CH592624A5 (ja) 1972-06-12 1973-06-07
FR7320929A FR2187346B1 (ja) 1972-06-12 1973-06-08
NL7308000A NL7308000A (ja) 1972-06-12 1973-06-08
GB2762773A GB1414020A (en) 1972-06-12 1973-06-11 Butyrophenone derivatives and production thereof
CA173,679A CA1023362A (en) 1972-06-12 1973-06-11 Butyrophenone derivatives and production thereof
HUSU819A HU167380B (ja) 1972-06-12 1973-06-12
DE2329813A DE2329813A1 (de) 1972-06-12 1973-06-12 Butyrophenonderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
BE132163A BE800791A (fr) 1972-06-12 1973-06-12 Derives de butyrophenone et leur production
US05/617,730 US4009173A (en) 1972-06-12 1975-09-29 Butyrophenone derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP47058789A JPS595588B2 (ja) 1972-06-12 1972-06-12 シンキナブチロフエノンユウドウタイ オヨビ ソノエン ノ セイホウ

Publications (2)

Publication Number Publication Date
JPS4914477A JPS4914477A (ja) 1974-02-07
JPS595588B2 true JPS595588B2 (ja) 1984-02-06

Family

ID=13094324

Family Applications (1)

Application Number Title Priority Date Filing Date
JP47058789A Expired JPS595588B2 (ja) 1972-06-12 1972-06-12 シンキナブチロフエノンユウドウタイ オヨビ ソノエン ノ セイホウ

Country Status (10)

Country Link
JP (1) JPS595588B2 (ja)
BE (1) BE800791A (ja)
CA (1) CA1023362A (ja)
CH (1) CH592624A5 (ja)
DE (1) DE2329813A1 (ja)
FR (1) FR2187346B1 (ja)
GB (1) GB1414020A (ja)
HU (1) HU167380B (ja)
NL (1) NL7308000A (ja)
SE (1) SE397089B (ja)

Also Published As

Publication number Publication date
JPS4914477A (ja) 1974-02-07
HU167380B (ja) 1975-09-27
BE800791A (fr) 1973-12-12
CH592624A5 (ja) 1977-10-31
NL7308000A (ja) 1973-12-14
CA1023362A (en) 1977-12-27
FR2187346A1 (ja) 1974-01-18
FR2187346B1 (ja) 1976-12-31
SE397089B (sv) 1977-10-17
GB1414020A (en) 1975-11-12
DE2329813A1 (de) 1974-01-03

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