JPS6124387B2 - - Google Patents

Info

Publication number
JPS6124387B2
JPS6124387B2 JP50117347A JP11734775A JPS6124387B2 JP S6124387 B2 JPS6124387 B2 JP S6124387B2 JP 50117347 A JP50117347 A JP 50117347A JP 11734775 A JP11734775 A JP 11734775A JP S6124387 B2 JPS6124387 B2 JP S6124387B2
Authority
JP
Japan
Prior art keywords
formula
alk
general formula
diaryl ester
following general
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
JP50117347A
Other languages
English (en)
Other versions
JPS51125228A (en
Inventor
Rafuon Bikutoru
Rafuon Rui
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.)
Cephalon France SAS
Original Assignee
Laboratoire L Lafon SA
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 claimed from GB4238774A external-priority patent/GB1519147A/en
Application filed by Laboratoire L Lafon SA filed Critical Laboratoire L Lafon SA
Publication of JPS51125228A publication Critical patent/JPS51125228A/ja
Publication of JPS6124387B2 publication Critical patent/JPS6124387B2/ja
Granted legal-status Critical Current

Links

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
    • C07D295/08—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
    • C07D295/088—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 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
    • A61P25/04—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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22—Radicals substituted by oxygen atoms
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid

Description

【発明の詳細な説明】 本発明はイオウ及び酸素を含有するジアリール
エステルの製造方法に関するものである。
本発明は次の一般式 （式中のAlkは直鎖又は分枝鎖状のC1〜C4炭化
水素基を示し、ｎは５〜10の数を示す）で表わさ
れるイオウ及び酸素を含有するジアリールエステ
ルを提供する。
Alk基は例えばCH2，CH（CH3），Ｃ
（CH3）2，CH2CH2，CH（CH3）CH2，Ｃ
（CH3）2CH2，CH2CH（CH3）又はCH2C（CH3）2
である。AlkはCH2，CH（CH3）又はＣ（CH3）2
であることが好ましい。
本発明のエステルは （式中のAlkは前述と同じものを示す）で表わ
される酸ジフエニル誘導体と、英国特許第
1307227号明細書に記載されている次式ビス−
〔（Ｓ−ヒドロキシアルキル）チオ〕−アルカン系
アルコールとのエステル化反応から生成する。
HOCH2CH2−Ｓ−Ｋ−Ｓ−CH2CH2OH ｂ 但し、式中のＫは前述したと同じものを示す。
ａ式の酸ジフエニル誘導体は、下記の２方法
及び適当なその変形方法により製造することがで
きる。
方法 Ａ 次の一般式 で表されるジフエニル誘導体を次の一般式 Hal−Alk−COOC2H5 （式中のHalは臭素原子又は塩素原子又は塩素
原子を示し、Alkは上述したと同じものを示す）
で表されるハロゲン誘導体とを反応させて、次の
一般式 （式中のAlkは前述と同じものを示す）で表わ
される化合物を製造する。
＋の反応を行う為には、式でHalがBrで
ある臭素誘導体を用いると特に好適である。
式のカルボキシレートを加水分解により相応
するａ式の酸ジフエニル誘導体に転化する。
方法Ａの変形としては例えば、式の化合物の
エステル交換反応による他のエステルの製造の場
合がある。
方法 Ｂ 方法Ａより僅かに一般的でない方法Ｂは、次の
一般式 で表わされる第一銅塩を、次の一般式 （式中のAlkは前述したと同じものを示す）で
表わされる臭素誘導体と反応させて、式のエス
テルを得、このエステルを加水分解してａ式の
酸ジフエニル誘導体を製造する。
方法Ｂの変形としては例えば式のエステルの
エステル交換反応がある。
製造例 ３，14−ジチア−１，16−ヘキサデシルジ−
〔４−（４−クロルフエニルチオ）−フエノキシ−
イソブチレート〕（コード番号CRL40253） ａ ｐ−（クロルフエニルチオ）−フエノキシ−イ
ゾブチロイルクロリド 15ｇ（0.0465モル）のｐ−（クロルフエニル
チオ）−フエノキシ−イソ酪酸（コード番号
CRL40201）と16.75ml（0.232モル）の塩化チ
オニルとの混合物を、還流温度で10分間加熱し
た。反応混合物をベンゼン中に取出した後、溶
液をカーボンブラツクの存在下で濾過し、溶媒
を蒸発させて、16ｇの橙色の油状物を得た。
収率＝約100％ ｂ CRL40253のもの 13ｇ（0.038モル）の前述の酸クロリドを25
mlのベンゼンに溶解した溶液を、５ｇ（0.017
モル）のビス−１，10−（２−ヒドロキシ−エ
チルチオ）−デカンを20mlのベンゼンと３ｇ
（0.038モル）のピリジンに懸濁した20〜55℃の
懸濁液に15分間で注入した。反応体を常温で一
液接触したまま放置した後、反応混合物を希薄
塩酸を用いて洗浄した。乾燥した硫黄ナトリウ
ム上で乾燥し、溶媒を蒸発させた後、17.5ｇの
橙色の油状物を得た。この油状物をジエチルエ
ーテルに溶解し、炭酸ナトリウム溶液で２回洗
浄し次いて希薄苛性ソーダ溶液で洗浄した後、
水に不溶性の橙色油状物15.55ｇを得た。この
ものの赤外線スペクトルは第１図に示す通じで
あり、コード番号CRL40253の物質であること
を認識した。
収率＝94％ 分子量911 本発明により製造されるジアリールエステル
は、循環系病気特に心臓血管の疾病の治療に有用
である。これ等の化合物の或るものは脂質低下
（hypo―lipidaemic）剤及びコレステロール低下
（hypo―cholesterolaemic）剤である。これ等の
エステルが有する性質は循環系病気特に心臓血管
の疾病に対する有益な治療的作用である。
薬理試験例 ウイスタールラツトを次のＡ〜Ｅの５バツチに
分けた。
Ａ………通常食餌のもの（抑制率＝０％） Ｂ………高脂質食餌のもの（抑制率＝０％） Ｃ………脂質正常化作用を有する参照化合物リパ
ブロン（２−（Ｐ−クロロフエノキシ）−
２−メチル−エチルプロピオネート）を
毎日0.1ｇ／Kgの割合で配合した高脂質
食餌のもの Ｄ………脂質正常化作用を有する他の化合物 L21558（１，10−ビス−（２−オキシエ
チル−チオ）−デカン）を毎日0.1ｇ／Kg
の割合で配合した高脂質食餌のもの Ｅ………CRL40253のものを毎日10mg／Kgの割合
で配合した高脂質食餌のもの ４日間給餌後、バツチＢのラツトに比べてバツ
チＥのラツトは、全脂質とコレステロールが夫々
40％減少していた。これに対してバツチＣ及びＤ
のラツトは全脂質とコレステロールの減少率が遥
かに劣つていた。
本発明は式の化合物の少なくとも１種以上を
そのまま、又は薬理学的に許容される賦形剤と組
合せた非毒性付加塩として含有する治療剤をもそ
の目的に含む。
【図面の簡単な説明】
第１図は本発明方法により製造したジアリール
エステルの赤外線スペクトル図である。

Claims (1)

  1. 【特許請求の範囲】 １ 次の一般式 （式中のAlkは直鎖又は分枝鎖状のC1〜C4炭化
    水素基、Ｋは（CH2）oを示し、ｎは５〜10の数を
    示す）で表される酸素及び硫黄を含有するジアリ
    ールエステルを製造するにあたり、次の一般式 （式中のAlkは前述したと同じものを示す） で表される酸ジフエニル誘導体を、次の一般式 HOCH2CH2−Ｓ−Ｋ−Ｓ−CH2CH2OH ｂ （式中のＫは前述したと同じものを示す）で表
    わされるビス〔（Ｓ−ヒドロキシアルキル）チ
    オ〕−アルカン系アルコールと反応させることを
    特徴とするジアリールエステルの製造方法。
JP50117347A 1974-09-30 1975-09-30 Preparation of diaryl compounds Granted JPS51125228A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4238774A GB1519147A (en) 1974-09-30 1974-09-30 Sulphur and oxygen-containing diaryl compounds

Publications (2)

Publication Number Publication Date
JPS51125228A JPS51125228A (en) 1976-11-01
JPS6124387B2 true JPS6124387B2 (ja) 1986-06-10

Family

ID=10424196

Family Applications (10)

Application Number Title Priority Date Filing Date
JP50117345A Expired JPS5820954B2 (ja) 1974-09-30 1975-09-30 フエニルスルフイニルユウドウタイ ノ セイゾウホウホウ
JP50117346A Expired JPS591258B2 (ja) 1974-09-30 1975-09-30 ジフエニルスルホキシド誘導体の製造方法
JP50117347A Granted JPS51125228A (en) 1974-09-30 1975-09-30 Preparation of diaryl compounds
JP50117344A Pending JPS51125237A (en) 1974-09-30 1975-09-30 Preparation of sulfurrcontaining arylamine derivative
JP59115621A Pending JPS6034939A (ja) 1974-09-30 1984-06-07 ジアリ−ル化合物の製造方法
JP59115619A Granted JPS6110524A (ja) 1974-09-30 1984-06-07 ジアリ−ル化合物の製造方法
JP59115620A Granted JPS6034935A (ja) 1974-09-30 1984-06-07 ジアリ−ル化合物の製造方法
JP59139795A Pending JPS60231628A (ja) 1974-09-30 1984-07-07 ジアリ−ル化合物の製造方法
JP59139796A Pending JPS60248656A (ja) 1974-09-30 1984-07-07 ジアリ−ル化合物の製造方法
JP59139794A Granted JPS60231648A (ja) 1974-09-30 1984-07-07 ジアリ−ル化合物の製造方法

Family Applications Before (2)

Application Number Title Priority Date Filing Date
JP50117345A Expired JPS5820954B2 (ja) 1974-09-30 1975-09-30 フエニルスルフイニルユウドウタイ ノ セイゾウホウホウ
JP50117346A Expired JPS591258B2 (ja) 1974-09-30 1975-09-30 ジフエニルスルホキシド誘導体の製造方法

Family Applications After (7)

Application Number Title Priority Date Filing Date
JP50117344A Pending JPS51125237A (en) 1974-09-30 1975-09-30 Preparation of sulfurrcontaining arylamine derivative
JP59115621A Pending JPS6034939A (ja) 1974-09-30 1984-06-07 ジアリ−ル化合物の製造方法
JP59115619A Granted JPS6110524A (ja) 1974-09-30 1984-06-07 ジアリ−ル化合物の製造方法
JP59115620A Granted JPS6034935A (ja) 1974-09-30 1984-06-07 ジアリ−ル化合物の製造方法
JP59139795A Pending JPS60231628A (ja) 1974-09-30 1984-07-07 ジアリ−ル化合物の製造方法
JP59139796A Pending JPS60248656A (ja) 1974-09-30 1984-07-07 ジアリ−ル化合物の製造方法
JP59139794A Granted JPS60231648A (ja) 1974-09-30 1984-07-07 ジアリ−ル化合物の製造方法

Country Status (8)

Country Link
US (2) US4013776A (ja)
JP (10) JPS5820954B2 (ja)
BE (4) BE833580A (ja)
CA (2) CA1073925A (ja)
CH (3) CH602618A5 (ja)
DE (3) DE2543252C2 (ja)
FR (3) FR2285867A1 (ja)
IE (3) IE42447B1 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH047997U (ja) * 1990-05-11 1992-01-24

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4098824A (en) * 1975-10-02 1978-07-04 Laboratoire L. Lafon Benzhydrylsulphinyl derivatives
DE2611695A1 (de) * 1976-03-19 1977-09-29 Hoechst Ag Herbizide mittel
GB1574822A (en) * 1976-03-23 1980-09-10 Lafon Labor Acetohydroxamic acid derivatives and pharmaceutical compositions thereof
DE2613697A1 (de) * 1976-03-31 1977-10-13 Hoechst Ag Herbizide mittel
GB1517603A (en) * 1976-04-02 1978-07-12 Lafon Labor Esters of 2-(4-(4-chlorobenzoyl)-phenoxy)-2-methyl-propionic acid with bis-(hydroxyalkylthio)-alkanes
GB1571829A (en) 1976-04-06 1980-07-23 Lafon Labor Sulphur-containing diaryl compounds and oxygen-containing diaryl compounds
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US4013776A (en) 1977-03-22
IE41849L (en) 1976-03-30
CA1073925A (en) 1980-03-18
BE833928A (fr) 1976-01-16
CA1040206A (en) 1978-10-10
JPS6034939A (ja) 1985-02-22
JPS60248656A (ja) 1985-12-09
CH603570A5 (ja) 1978-08-31
DE2543252A1 (de) 1976-04-08
JPS5163146A (ja) 1976-06-01
CH602618A5 (ja) 1978-07-31
JPS6260381B2 (ja) 1987-12-16
JPS60231628A (ja) 1985-11-18
FR2285860B1 (ja) 1980-05-30
JPS5820954B2 (ja) 1983-04-26
BE833927A (fr) 1976-01-16
IE42447B1 (en) 1980-08-13
JPS51125228A (en) 1976-11-01
IE41724L (en) 1976-03-30
IE41849B1 (en) 1980-04-09
DE2543252C2 (de) 1986-09-18
JPS51131848A (en) 1976-11-16
JPS51125237A (en) 1976-11-01
BE833843A (fr) 1976-01-16
JPS6216938B2 (ja) 1987-04-15
US4065584A (en) 1977-12-27
JPS6034935A (ja) 1985-02-22
FR2285867B1 (ja) 1980-05-30
CH611600A5 (ja) 1979-06-15
DE2543184A1 (de) 1976-04-01
FR2285867A1 (fr) 1976-04-23
BE833580A (fr) 1976-01-16
FR2285860A1 (fr) 1976-04-23
IE41724B1 (en) 1980-03-12
JPS591258B2 (ja) 1984-01-11
FR2285859A1 (fr) 1976-04-23
JPS60231648A (ja) 1985-11-18
JPS6310148B2 (ja) 1988-03-04
FR2285859B1 (ja) 1980-05-30
DE2543249A1 (de) 1976-04-08
JPS6110524A (ja) 1986-01-18
IE42447L (en) 1975-09-30
DE2543184C2 (ja) 1989-01-19

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