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JPS5855126B2 - α，αジハロ置換フエニルエタン化合物の製造方法 - Google Patents

α，αジハロ置換フエニルエタン化合物の製造方法

Info

Publication number
JPS5855126B2
JPS5855126B2 JP52147696A JP14769677A JPS5855126B2 JP S5855126 B2 JPS5855126 B2 JP S5855126B2 JP 52147696 A JP52147696 A JP 52147696A JP 14769677 A JP14769677 A JP 14769677A JP S5855126 B2 JPS5855126 B2 JP S5855126B2
Authority
JP
Japan
Prior art keywords
compound
producing
formula
dihalo
dichloro
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
JP52147696A
Other languages
English (en)
Other versions
JPS53101315A (en
Inventor
ジユリアス・ダイアモンド
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.)
William H Rorer Inc
Original Assignee
William H Rorer Inc
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 William H Rorer Inc filed Critical William H Rorer Inc
Publication of JPS53101315A publication Critical patent/JPS53101315A/ja
Publication of JPS5855126B2 publication Critical patent/JPS5855126B2/ja
Expired legal-status Critical Current

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    • C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
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Description

【発明の詳細な説明】 本発明は、α・α−ジクロロ置換フェニルエタン化合物
の製造方法に関し、詳細には、式：（式中Ｒはシクロア
ルキル基であり、Ｙは水素原子またはハロゲン原子であ
る。
）で示される新規エチニルベンゼン化合物の中間体であ
る式： （式中Ｒ，Ｙは前記定義通りである） で示されるα・α−ジクロロ置換フェニルエタン化合物
の製造方法に関する。
上記式■で表わされるエチニルベンゼン化合物は抗炎症
剤、鎮痛剤および解熱剤として特に有用である。
本明細書において、「シクロアルキル」とは約７個まで
の炭素原子を有する炭化水素環を意味する。
本発明の目的化合物である式： （式中のＲ，Ｙは前記定義どおりである）で示されるα
・α−ジクロロ置換フェニルエタン化合物は、式： ご（式中Ｒ，Ｙは前記定義通りである） で表わされる置換アセトフェノンを五塩化リンのような
・・ロケ／化剤と反応させて製造される。
本発明方法により得られたジクロロ化合物を液体アンモ
ニア中のナトリウムアミドを用いて脱塩素化すれば前記
式■で表わされるエチニルベンゼン化合物が得られる。
この過程は３−・・ロー４置換アセトフエノンから３〜
ハロー４ 一置換フェニルアセチレンを形成する場合に
特に有用である。
前記式Ｉで表わされるエチニルベンゼン化合物は補乳類
において有益な抗炎症作用を有し、付随する疼痛および
発熱の処置および消炎症剤の反作用である同様の症状の
処置に効果的である。
一般的に、該化合物は炎症およびそれに伴う発熱と疼痛
の徴候が現れる広範囲な補乳類の症状に望ましい。
このような症状の例は；リューマチ性関節炎、骨関節炎
およびその他の変性関節炎のごときリューマチ性疾病：
のごとき軟組織リューマチ症；座骨神経痛のごとき筋肉
リューマチ症；口腔外科に伴う疼痛および炎症および抗
炎症剤、鎮痛剤および／または解熱剤の使用を必要とす
る上記の徴候を示す同様の人体および家畜の疾病である
。
該化合物は顕著な鎮痛作用を示し、疼痛および発熱の軽
減に効果的である。
これらの化合物は本質的に胃内出血の副作用がない。
以下の記載は本発明の目的化合物の製造を示す例である
。
これらの例は化合物を例示するものであっては本発明を
限定する意図ではない。
実施例 １ ３−クロロ−４−シクロへキシルアセトフェノン（０，
２５モル）および五塩化リン（０，３１モル）を機械的
攪拌器、窒素供給口に接続されたコンテンサーおよび温
度計を具えた二頭フラスコに入れた。
この混合物を３３−３５℃で３日間攪拌した。
、冷却した反応混合物を氷ｇｏｏｒに注加し、エーテル
３Ｘ５０Ｑｍｌで抽出した。
このエーテルフラクションを２×１００ｍ１水、４×１
００ｍ７の５％水酸化ナトリウム、３×５０ｒｒＬｌ水
、２Ｘ５Ｑｍｌの飽和食塩水で洗浄し、硫酸ナトリウム
で乾燥した。
エーテルを除去して３−クロル−４−シクロヘキシルフ
ェニルα・α−ジクロル−エタンカ得うれた。
参考例 １ 実施例１の生成物を無水ＴＨＦ （２００ｍ１ｌ）に溶
解し、新らたに製造した液体アンモニウム中ナトリウム
アミドの溶液にドライアイスコンデンサーを用いて滴下
した。
この反応混合物を室温で一夜攪拌し、次いで水の５０ｍ
１およびエーテルの５００ｍ１に注加した。
エーテルフラクションを３×５０ｍ１水および飽和食塩
水の５０ＴｒＬｌで洗浄し、硫酸ナトリウムで乾燥した
。
溶媒を除去すれば残渣が得られ、これを蒸留すれば３−
クロロ−４−シクロへキシルエチニルベンゼンが得うれ
た。
ｂｐ９１〜９３℃ 参考例 ２ 参考例１の方法に準拠して下記の化合物を製造した。
ｐ−シクロペンチルエチニルベンゼン ｐ−シクロヘキシルエチニルベンゼン ｐ−シクロヘプチルエチニルベンゼン ３−ブロモ−４−シクロへキシルエチニルベンゼン ３−フルオロ−４−シクロヘキシルエチニルベンゼン ３−ヨード−４−シクロヘキシルエチニルベンゼン ３・５−ジクロロ−４−シクロへキシルエチニルベンゼ
ン ３−Ｊ’ロロー５−フロモー４−シ）口へキシルエチニ
ルベンゼン ３−クロロ−５−フルオロ−４−シクロヘキシプ☆ルエ
チニルベンゼン ３−クロロ−４−シクロペンチルエチニルベンゼン ３−ブロモ−４−シクロペンチルエチニルベンゼン ３−フルオロ−４−シクロペンチルエチニルベンゼン ３・５−ジクロロ−４−シクロペンチルエチニルベンゼ
ン ３−クロロ−４−シクロへブチルエチニルベンゼン ３−フロモー４−シクロヘプチルエチニルベンゼン ３・５−ジクロロ−４−シクロへブチルエチニルベンゼ
ン 以下に、本発明方法により得られるα・α−ジクロロ置
換フェニルエタン化合物から製造された化合物の薬理効
果を示す。
参考例 ３ ３−クロロ−４−シクロヘキシルエチニルベンゼンの薬
理効果を次の如くして測定した。
カラゲーニン踵浮腫分析 １群が６匹からなる雄のＳ ｐｒａｇｕｅ −Ｄａｗ
ｌｅｙラットに、その右の後踵に０．１ ｒｎｌの１％
力ラう−ニンを注入する１時間前に３ｍｌの３−ニトロ
−４シクロヘキシルエチニルベンゼンを経口投与したつ
投与直後とその３時間後に踵の体積を水銀置換により測
定し、記録した。
初期体積と最終体積との差が浮腫の測定値となる。
阻止率ので表現されるテスト化合物の効果を式： により計算した。
次のデータに示される如く、 対応するプロピオ ン酸（３−クロロ−４−シクロヘキシルフェニルプロピ
オン酸）は実質上無効であった。

Claims (1)

  1. 【特許請求の範囲】 １ 式： （式中Ｒはシクロアルキル基であり、Ｙは水素原子また
    はハロゲン原子である。 ）で表わされるジクロロ化合物の製造方法において、 式： （式中Ｒ，Ｙは前記定義通りである） で表わされる置換アセトフェノンを五塩化燐と反応させ
    ることからなる製造方法。
JP52147696A 1972-07-03 1977-12-08 α，αジハロ置換フエニルエタン化合物の製造方法 Expired JPS5855126B2 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US00268419A US3852364A (en) 1972-07-03 1972-07-03 Ethynylbenzene compounds derivatives therefor
US000000268419 1972-07-03

Publications (2)

Publication Number Publication Date
JPS53101315A JPS53101315A (en) 1978-09-04
JPS5855126B2 true JPS5855126B2 (ja) 1983-12-08

Family

ID=23022917

Family Applications (4)

Application Number Title Priority Date Filing Date
JP48074487A Expired JPS5915889B2 (ja) 1972-07-03 1973-07-03 エチニルベンゼン化合物の製造方法
JP52147695A Expired JPS59485B2 (ja) 1972-07-03 1977-12-08 エチニルベンゼン化合物の製造方法
JP14769777A Pending JPS53105448A (en) 1972-07-03 1977-12-08 Method for production of compound of phenylpropiolic acid
JP52147696A Expired JPS5855126B2 (ja) 1972-07-03 1977-12-08 α，αジハロ置換フエニルエタン化合物の製造方法

Family Applications Before (3)

Application Number Title Priority Date Filing Date
JP48074487A Expired JPS5915889B2 (ja) 1972-07-03 1973-07-03 エチニルベンゼン化合物の製造方法
JP52147695A Expired JPS59485B2 (ja) 1972-07-03 1977-12-08 エチニルベンゼン化合物の製造方法
JP14769777A Pending JPS53105448A (en) 1972-07-03 1977-12-08 Method for production of compound of phenylpropiolic acid

Country Status (10)

Country Link
US (3) US3852364A (ja)
JP (4) JPS5915889B2 (ja)
AU (1) AU468424B2 (ja)
BE (1) BE809147A (ja)
CA (1) CA1084521A (ja)
CH (1) CH599080A5 (ja)
DE (1) DE2334425A1 (ja)
FR (1) FR2190462B1 (ja)
GB (1) GB1442178A (ja)
NL (1) NL7316075A (ja)

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* Cited by examiner, † Cited by third party
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US3907897A (en) * 1971-07-21 1975-09-23 Rorer Inc William H Cycloalkylbenzaldehydes
US4093737A (en) * 1972-07-03 1978-06-06 William H. Rorer, Inc. Ethynylbenzene compounds and derivatives thereof in the treatment of pain, fever or inflammation
US3852364A (en) * 1972-07-03 1974-12-03 Rorer Inc William H Ethynylbenzene compounds derivatives therefor
US3987116A (en) * 1972-11-13 1976-10-19 William H. Rorer, Inc. Ethynylaryl compounds and derivatives thereof
US3928450A (en) * 1973-11-16 1975-12-23 Hughes Aircraft Co Acetylene substituted aromatic primary amines and the process of making them
US3991212A (en) * 1973-12-26 1976-11-09 Eli Lilly And Company Anti-inflammatory agents
US4301313A (en) * 1973-12-26 1981-11-17 Eli-Lilly And Company Halogenated ethynyl biphenyls
US4166133A (en) * 1974-01-07 1979-08-28 William H. Rorer, Inc. Ethynylbenzene compounds and derivatives thereof to treat pain, fever and inflammation
GB1499655A (en) * 1974-01-31 1978-02-01 Allen & Hanburys Ltd Biphenyl derivatives
US3944614A (en) * 1974-04-17 1976-03-16 The United States Of America As Represented By The Secretary Of The Air Force 2,2'-Bis(phenylethynyl-5,5'-diaminobenzidine
US3968251A (en) * 1974-07-05 1976-07-06 Eli Lilly And Company Arylacetylene compounds as antithrombotic agents
US3928604A (en) * 1974-07-05 1975-12-23 Lilly Co Eli Arylacetylene compounds as antithrombotic agents
US4042584A (en) * 1974-08-19 1977-08-16 Merck & Co., Inc. Ethynylaryl phenyl cyclopropyl thiazines and morpholines
US3952067A (en) * 1974-11-12 1976-04-20 William H. Rorer, Inc. Ethynylbenzenes
US4120885A (en) * 1975-05-14 1978-10-17 William H. Rorer, Inc. Ethynylbenzene compounds and derivatives thereof
US4226887A (en) * 1979-04-16 1980-10-07 Eli Lilly And Company Anti-inflammatory agents
US4284832A (en) * 1980-04-28 1981-08-18 The United States Of America As Represented By The Secretary Of The Army Conversion of CS (tear gas) to o-chlorostyrene and ammonium sulfate
US4465833A (en) * 1980-10-15 1984-08-14 Hughes Aircraft Company Process for preparing ethynylated benzoic acid derivatives
US4528114A (en) * 1981-12-18 1985-07-09 Hoffmann-La Roche Inc. Acetylenes
US4665246A (en) * 1984-03-09 1987-05-12 Chem Biochem Research, Inc. Method of producing ethynyl aromatic compounds
FR2649975B1 (fr) * 1989-07-19 1991-11-22 Inst Nat Rech Chimique Nouveaux derives acetyleniques, leur procede de preparation, nouveaux polymeres acetyleniques et leurs applications
US6297405B1 (en) * 2000-09-01 2001-10-02 Milliken & Company Fluorinated and chlorinated benzaldehydes

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542888A (en) * 1968-10-07 1970-11-24 Labofnia Sa Production of ethynyl benzenes
US3852364A (en) * 1972-07-03 1974-12-03 Rorer Inc William H Ethynylbenzene compounds derivatives therefor

Also Published As

Publication number Publication date
FR2190462B1 (ja) 1977-11-25
JPS53101315A (en) 1978-09-04
FR2190462A1 (ja) 1974-02-01
BE809147A (fr) 1974-04-16
JPS53108931A (en) 1978-09-22
AU468424B2 (en) 1976-01-15
US3923910A (en) 1975-12-02
JPS53105448A (en) 1978-09-13
JPS59485B2 (ja) 1984-01-07
US3852364A (en) 1974-12-03
AU6363973A (en) 1975-06-19
DE2334425A1 (de) 1974-01-24
GB1442178A (en) 1976-07-07
CH599080A5 (ja) 1978-05-12
CA1084521A (en) 1980-08-26
NL7316075A (nl) 1975-05-27
JPS5915889B2 (ja) 1984-04-12
US3898292A (en) 1975-08-05
JPS4951229A (ja) 1974-05-18

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