JPS595588B2 - Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou - Google Patents

Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou

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
Japanese (ja)
Other versions
JPS4914477A (en
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/en
Priority to SE7307963A priority patent/SE397089B/en
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 DE2329813A priority patent/DE2329813A1/en
Priority to HUSU819A priority patent/HU167380B/hu
Priority to BE132163A priority patent/BE800791A/en
Publication of JPS4914477A publication Critical patent/JPS4914477A/ja
Priority to US05/617,730 priority patent/US4009173A/en
Publication of JPS595588B2 publication Critical patent/JPS595588B2/en
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)
  • Pain & Pain Management (AREA)
  • Anesthesiology (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。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing novel butylophenone derivatives and salts thereof.

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。To explain in more detail, general formula [I] [wherein R
, is an acyl group represented by R3CO (wherein, R3 represents a lower alkyl group).

）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。), R5 is a halogen atom, and z is H2 or an oxygen atom. ] This invention relates to a method for producing a novel butyrophenone derivative.

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。These novel derivatives obtained by the present invention exhibit central nervous system depressant action and analgesic action, and have the so-called medial effect.
It is useful not only as a tranquilizer but also as an intermediate for sedatives, anti-inflammatory agents, and the like.

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。The object of the present invention is to provide an industrially advantageous method for producing such useful drugs. That is, the present invention is based on the general formula (where R3, R, and z are as described above).

〕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。] Oxidize the indole derivative with an oxidizing agent.
This is a method for producing a novel butylophenone derivative represented by the general formula [I] and a salt thereof by further treating with an acid if necessary. ．． Examples of the oxidizing agent in the present invention include ozone, hydrogen peroxide, peracids (for example, performic acid, peracetic acid, perbenzoic acid),
Chromic acid, potassium permanganate, etc. are suitable, but
Of course, it is not limited to these. Butyrophenone derivatives obtained by the above method can be prepared by using acids such as hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid, thiocyanic acid, acetic acid, propionic acid, oxalic acid, citric acid, malic acid, tartaric acid, fumaric acid,
It can also be treated with maleic acid, citric acid, glycolic acid, benzoic acid, cinnamic acid, p-aminosalicylic acid, salicylic acid, metasulfonic acid, ascorbic acid, etc. to form an acid addition salt.

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。The starting material used in the present invention, that is, the compound represented by the above general formula, is synthesized, for example, by the following method.

〔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。[In the formula, R3 and R5 are as described above, and X represents a halogen atom.

〕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。[Examples] In order to describe the present invention in more detail, Examples are given below, but these are merely examples and the present invention is not limited to these in any way.

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。Example 1 5 tons of 2-methyl-3-[γ-(4'-piperidino-4'carbamoyl-piperidino)propyl]-6 fluorindole hydrochloride was dissolved in 140 ml of glacial acetic acid, and the mixture was heated under ice-cooling for 100-200 min. When ozone gas is introduced at a temperature of .degree. C., the reaction solution gradually becomes colored and becomes reddish, but this color fades again with time and becomes a pale yellow solution after 50 minutes.

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。This was made alkaline with 10% sodium hydroxide solution,
Extract with ethyl acetate, and dry the ethyl acetate under reduced pressure to obtain a candy-like substance. When this is treated with an ethanolic solution of hydrochloric acid, the hydrochloride of 2-acetamino-4-fluoro-r-(4'piperidino-4'-carbamoylpiperidino)-butyrophenone is obtained. Melting point 233-238°C (decomposition) Example 2 2-Methyl 3-[γ-
(41-piperidino-4'-aminomethylpiperidino)
2-acetylamino-4fluoro-r-(4'-piperidino-4'-aminomethylpiperidino)-butylphenone hydrochloride was obtained by oxidizing propyl]-6-fluorindole.

Claims (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。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_3 represents a lower alkyl group, R_5 represents a halogen atom, and Z represents H_2 or an oxygen atom. ] The indole derivative represented by is treated with an oxidizing agent,
Furthermore, there are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼ that are characterized by treatment with acid if necessary. [In the formula, R_5 and Z are as described above. R_1 represents an acyl group R_3CO (R_3 is as described above). ] A method for producing a novel butyrophenone derivative and its salt.
JP47058789A 1972-06-12 1972-06-12 Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou Expired JPS595588B2 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
JP47058789A JPS595588B2 (en) 1972-06-12 1972-06-12 Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou
SE7307963A SE397089B (en) 1972-06-12 1973-06-06 PROCEDURE FOR THE PREPARATION OF BUTYROFENONE DERIVATIVES
CH826373A CH592624A5 (en) 1972-06-12 1973-06-07
FR7320929A FR2187346B1 (en) 1972-06-12 1973-06-08
NL7308000A NL7308000A (en) 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
DE2329813A DE2329813A1 (en) 1972-06-12 1973-06-12 BUTYROPHENONE DERIVATIVES, THEIR SALTS, PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
HUSU819A HU167380B (en) 1972-06-12 1973-06-12
BE132163A BE800791A (en) 1972-06-12 1973-06-12 BUTYROPHENONE DERIVATIVES AND THEIR 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 (en) 1972-06-12 1972-06-12 Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou

Publications (2)

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

Family

ID=13094324

Family Applications (1)

Application Number Title Priority Date Filing Date
JP47058789A Expired JPS595588B2 (en) 1972-06-12 1972-06-12 Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou

Country Status (10)

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

Also Published As

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

Similar Documents

Publication Publication Date Title
US3218324A (en) 1-methyl ergotamines and ergocornines
US2872453A (en) Indole derivatives
JPS5839826B2 (en) Shinkinalolefinic acid aminoketone information
JPH02111776A (en) Tetracyclic antidepressant
US5084456A (en) Oxazolopyridine compounds
US3915988A (en) Benzopyranopyrazolecarboxylic acids
JPS595588B2 (en) Synkinabutylofenon Yudoutai Oyobi Sonoen no Seihou
US3491097A (en) 3-(piperazinoalkyl)-pyrazoles
DE3410168A1 (en) Novel isochinoline diones, process for their preparation, medicaments containing these compounds and intermediates
JPS6112912B2 (en)
JPH04230382A (en) Citric acd nobelastine and preparation thereof
Rao et al. Streponigrin and related compounds. II. Synthesis of the c‐ring precursors
JPS58177993A (en) Novel quinoline and related compounds useful as antiallergic
US2726244A (en) Water-soluble mono-betaine hydrazones of the aminochromes and process of preparing same
JPH02268162A (en) Diphenylpyridine derivative
JPS60222482A (en) Quinolizinone compound, its preparation, and drug composition containing it
JPH0517448A (en) 14-o-p-chlorobenzoylaconine and analgesic and antiinflammatory agent
US3144457A (en) Nu-(2-phthalimidoethyl) quaternary ammonium salts of triethylenediamine
JPS605599B2 (en) Method for producing aminobenzophenone derivatives
US3048586A (en) Novel derivatives of phenoxazine and processes for their preparation
US3520885A (en) Phenothiazine salts
US3499890A (en) Certain octahydro-1,12-trimethyleneindolo(2,3-a)quinolizines
JPS584768A (en) Novel 1-benzyl-3,4-dihydroisoquinoline derivative, manufacture and pharmaceutical composition
US3013026A (en) Process for the preparation of 3-keto-deta-20-alkylamino steroids
US2489351A (en) Preparation of benzotriazine compounds