JPS5921850B2 - 新ナフタレン誘導体の製法 - Google Patents

新ナフタレン誘導体の製法

Info

Publication number
JPS5921850B2
JPS5921850B2 JP57190680A JP19068082A JPS5921850B2 JP S5921850 B2 JPS5921850 B2 JP S5921850B2 JP 57190680 A JP57190680 A JP 57190680A JP 19068082 A JP19068082 A JP 19068082A JP S5921850 B2 JPS5921850 B2 JP S5921850B2
Authority
JP
Japan
Prior art keywords
formula
methoxy
manufacturing
naphthalene derivatives
naphthyl
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
JP57190680A
Other languages
English (en)
Other versions
JPS58113142A (ja
Inventor
アンソニ−・ウイリアム・レイク
カ−ル・ジヨ−ン・ロ−ズ
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 Beecham Group PLC filed Critical Beecham Group PLC
Publication of JPS58113142A publication Critical patent/JPS58113142A/ja
Publication of JPS5921850B2 publication Critical patent/JPS5921850B2/ja
Expired legal-status Critical Current

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    • 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
    • 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]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/26—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydration of carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

【発明の詳細な説明】 本発明は医薬としての効果を有するナフタレン誘導体の
製法に関するものである。
ある種のナフタレン誘導体は有用な抗炎症性をフ 有し
、種々のリウマチ性および関節炎性病状の治療に使用す
るのに適していることが知られている。
臨床的に使用できることが知られている特に効果がある
ナフタレン誘導体のひとつに式（Ｉ）□Ｃｏ２ＨＣＨ３
Ｏ（Ｉ） を有するナプロキセン（ＮａｐｒＯｘｅｎ）がある。
この化合物およびこれに関連するある種の化合物は英国
特許第１２７１１３２号、同第１２７４２７１号、同第
１２７４２７２号、同第１２７４２７３号、同第１２９
１３８６号、同第１２１１１３４号、同第１２９７３０
６号、同第１２７６２６１号、同第１２１６８８２号、
同第１２８９０４１号、同第１３２１３４７号およ．び
同第１２９６４９３号の各明細書に記載されている。
この種の化合物の薬理学的効果も文献〔Ｊ−Ｍｅｄ・Ｃ
ｈｅｍ，．ｌｊ，．２Ｏ３、（１９７０）、Ｊ・Ｐｈａ
ｍ−Ｅｘｐ−Ｔｈｅｒａ，．…、１１４、（１９７１）
〕に記載されている。残念ながら式（１）の化合物は治
療用投与量をあまり大して越えない投与量で、ある被験
者の胃腸に激しい刺激を生じることがある。
本発明によつて、他のナフタレン誘導体が良好な抗炎症
性を有するばかりでなく、胃腸内の刺激に基いて体重に
対する薬効量の比率が改良されていることが分かつた。
この化合物は式（）を有する化合物である。
従つて本発明の化合物は４−（６′−メトキシ２′−ナ
フチル）ブト一３−エン一２−オンである。
本発明の化合物はネズミのカラゲエニン抗炎症性試験で
１００ｍｆ７／Ｋｇ／日の投与量で試験したとき顕著な
抗炎症性を示したが、３倍も高い投与量で胃に刺激を与
えなかつた。本発明の化合物は人間に対する経口投与に
適した抗炎性および（または）鎮痛性組成物に入れるこ
とができる。
この種の組成物は錠剤、カプセル剤、粉末等任意の形に
することができる。単位投与量を含有する形のときには
通常式（）の薬効成分を２０〜１０００Ｗ９、さらに一
般的には１００〜６００ｒＩ１ｇを含有する。
このような単位投与量を含有する形は１日１回以上、好
ましくは１日２〜４回に、７０ｋ９の体重の人間の１日
投与量が通常３００〜３０００Ｗ９、さらに好ましくは
５００〜２０００ｒ！１９たとえば６００〜１６００Ｔ
ｆ１９になるようにすることができる。本発明によれば
下記よりなる前記（）の新しい化合物の製法が得られる
。
（ａ）式（） を有する６−メトキシ−２−ナフトアルデヒドを、式（
）を有するウイテイヒ（Ｗｉｔｔｉｇｒｅａｇｅｎｔ）
の反応剤（式中Ｑは三置換リン原子である）と反応させ
るか、（ｂ）式（Ｖ） を有する４−（６′−メトキシ−２′−ナフチル）ブト
一４−ヒドロキシ−２−オンを脱水することによつて式
（）を有する化合物を製造することができる。
方法（ａ） この反応は通常不活性有機溶媒中で起る。
一般に許容される程度の収率を与える好適なＱのグルー
プにはＰｈ３Ｐ，．Ｍｅ３Ｐ，．Ｅｔ３Ｐ等がある。方
法（ｂ）この化合物の脱水は通常の条件下、たとえば加
熱下または酸のような脱水触媒の存在下で起る。
この種の反応は容易に進行する。実施例 １ ４−（６′−メトキシ−２′−ナフチル）−ブト一３−
エン一２−オン６−メトキシ−２−ナフトアルデヒド１
．５ｒ１トリフエニルアセトニルホスフイン４ｒ１テト
ラヒドロフラン２００ｍ１を１２０時間還流下に保持し
た。
５ＮＨＣ１１００ｍ１をこの混合物に添加し、更に酢酸
エチル７００ｍ１を添加した。
有機層を分離し、水性層を酢酸エチル（２Ｘ２００ｍ０
で抽出し、精製有機層を水洗し、無水Ｎａ２ｓＯ４で乾
燥し、蒸発させたところ褐色の固形分を得た。この固形
分をシリカゲルカラムで溶出剤としてベンゼンを用いて
クロマトグラフにかけたところ、アルデヒド４００ｒ１
７９と４−（６′−メトキシ−２２ナフチル）−ブト一
３−エン一２−オン１，１５７が得られた。石油エーテ
ル（８０〜１００℃）からの融点１２０℃。実施例 ２ ４−（６′−メトキシ−２′−ナフチル）−ブト３−エ
ン一２−オン６−メトキシ−２−ナフトアルデヒド３０
７をアセトン５００７ｆＬｍ中で１０％の水酸化ナトリ
ウム水溶液１０ｍ１と３時間かきまぜて４−（６′−メ
トキシ−２！−ナフチル）−４−ヒドロキシ−２−オン
を生成する。
溶液を酸性にし、エーテルで抽出する。エーテル溶液を
ＭｇＳＯ４で乾燥し、減圧蒸発すると固体３０７を得る
。この不純物をシリカゲルのコラムで溶離液にベンゼン
を使用して精製すると、融点１２０℃の４−（６′−メ
トキシ−２′ナフチル）−ブト一３−エン一２−オン１
５７を得る。参考例 １ 薬理学的データ 通常のアレン、ドイジ一試験を使用し、本発明の化合物
の発情性を試験した結果を第１表に示す。
ネズミの足のカラゲエニン標準試，験法（Ｓｔａｎｄａ
ｒｄＲａｔＰａｗＣａｒｒａｇｅｅｉｎＴｅｓｔ）を使
用し、本発明の化合物の炎症静作用を試験した結果も第
１表に示す。この結果は過度の発情性が期待されないよ
うな投与量で本発明の化合物は高水準の鎮静作用を有す
ることを示している。
本発明の化合物は３００Ｔｒ１９／Ｋ９／日を経口投与
して３日後のネズミの胃に過度の刺激を与えないが、式
（）の化合物を同一投与量で経口投与した場合には１．
５日後に、激しい胃の刺激が認められる。

Claims (1)

  1. 【特許請求の範囲】 １ 式（III） ▲数式、化学式、表等があります▼（III）を有する６
    −メトキシ−２−ナフトアルデヒドを、式（IV）Ｑ＝Ｃ
    ＨＣＯＣＨ＿３（IV） （式中、Ｑは三置換リン原子を表す）を有するウイテイ
    ヒの反応剤と反応させることを特徴とする、式（II）▲
    数式、化学式、表等があります▼（II）を有する４−（
    ６′−メトキシ−２′−ナフチル）ブト−３−エン−２
    −オンの製法。 ２ 式（Ｖ） ▲数式、化学式、表等があります▼（Ｖ）を有する化合
    物を脱水することを特徴とする式（II）▲数式、化学式
    、表等があります▼（II）を有する４−（６′−メトキ
    シ−２′−ナフチル）ブト−３−エン−２−オンの製法
    。
JP57190680A 1973-09-11 1982-10-29 新ナフタレン誘導体の製法 Expired JPS5921850B2 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB42550 1973-09-11
GB4255073A GB1474377A (en) 1973-09-11 1973-09-11 Naphthalene derivatives

Publications (2)

Publication Number Publication Date
JPS58113142A JPS58113142A (ja) 1983-07-05
JPS5921850B2 true JPS5921850B2 (ja) 1984-05-22

Family

ID=10424914

Family Applications (4)

Application Number Title Priority Date Filing Date
JP49103764A Expired JPS5920655B2 (ja) 1973-09-11 1974-09-09 新ナフタレン誘導体の製法
JP57190680A Expired JPS5921850B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法
JP57190679A Expired JPS6033818B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法
JP57190681A Expired JPS605580B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法

Family Applications Before (1)

Application Number Title Priority Date Filing Date
JP49103764A Expired JPS5920655B2 (ja) 1973-09-11 1974-09-09 新ナフタレン誘導体の製法

Family Applications After (2)

Application Number Title Priority Date Filing Date
JP57190679A Expired JPS6033818B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法
JP57190681A Expired JPS605580B2 (ja) 1973-09-11 1982-10-29 新ナフタレン誘導体の製法

Country Status (15)

Country Link
JP (4) JPS5920655B2 (ja)
BE (1) BE819794A (ja)
CH (8) CH613932A5 (ja)
CY (2) CY1083A (ja)
DE (2) DE2442305C2 (ja)
DK (1) DK156642C (ja)
FR (1) FR2242972B1 (ja)
GB (1) GB1474377A (ja)
HK (2) HK56180A (ja)
IE (1) IE40001B1 (ja)
KE (2) KE3081A (ja)
MY (2) MY8100198A (ja)
NL (1) NL175812C (ja)
SE (2) SE420598B (ja)
ZA (1) ZA745441B (ja)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL52006A0 (en) * 1976-05-13 1977-07-31 Beecham Group Ltd Novel nephthalene derivatives their preparation and pharmaceutical compositions containing them
GB2014993B (en) * 1977-11-03 1982-05-12 Beecham Group Ltd Chemical compounds
DE2860631D1 (en) * 1978-01-07 1981-05-07 Beecham Group Plc Process for the preparation of 4-(6-methoxy-2-naphthyl)butan-2-one and 2-acetyl-3-(6-methoxy-2-naphthyl) propenoic acid esters
CA1142965A (en) * 1979-06-08 1983-03-15 Alexander C. Goudie Substituted decalins, their preparation and use
GB8416638D0 (en) * 1984-06-29 1984-08-01 Beecham Group Plc Topical treatment and composition
GB8607119D0 (en) * 1986-03-21 1986-04-30 Beecham Group Plc Process
DE69120491T2 (de) * 1990-09-18 1996-11-14 Fujitsu Ltd Cursorverschiebungssteuerungsgerät für eine Rechneranzeige
GB9108128D0 (en) * 1991-04-15 1991-06-05 Zambeletti Spa L Novel formulation
GB9201857D0 (en) 1992-01-29 1992-03-18 Smithkline Beecham Plc Novel compound
GB9222849D0 (en) * 1992-10-31 1992-12-16 Smithkline Beecham Plc Novel use of pharmaceutical compositions
WO1997032837A1 (fr) * 1996-03-06 1997-09-12 Sumitomo Pharmaceuticals Co., Ltd. Derives estrogenes non steroidiens
US5861538A (en) * 1997-08-04 1999-01-19 Albemarle Corporation Production of alkoxynaphthyl-substituted ketones from naphthaldehydes
WO2003104178A1 (en) * 2002-06-07 2003-12-18 Cortical Pty Ltd Napththalene derivatives which inhibit the cytokine or biological activity of macrophage migration inhibitory factor (mif)
EP2123621A1 (de) 2008-05-20 2009-11-25 Bayer Schering Pharma Aktiengesellschaft Neue {F-18}-markierte L-Glutaminsäure- und L-Glutaminderivate (I), ihre Verwendung sowie Verfahren zu ihrer Herstellung
EP2123619A1 (de) 2008-05-20 2009-11-25 Bayer Schering Pharma AG Neue [F-18]-Markierte L-Glutaminsäure-und L-Glutaminderivate (II), ihre Verwendung sowie Verfahren zu ihrer Herstellung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO125971B (ja) * 1969-05-22 1972-12-04 Syntex Corp
BR6915468D0 (pt) * 1969-10-09 1973-03-13 Syntex Corp Processo para a preparacao de d 2-(6-substituido-2-naftil)-propanal

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KE3082A (en) 1980-10-03
JPS58113142A (ja) 1983-07-05
JPS5920655B2 (ja) 1984-05-15
SE420598B (sv) 1981-10-19
SE7907064L (sv) 1979-08-23
DE2442305A1 (de) 1975-03-13
IE40001L (en) 1975-03-11
ZA745441B (en) 1975-08-27
JPS5896036A (ja) 1983-06-07
MY8100198A (en) 1981-12-31
CH603527A5 (ja) 1978-08-15
CH603525A5 (ja) 1978-08-15
KE3081A (en) 1980-10-03
BE819794A (fr) 1975-03-11
GB1474377A (en) 1977-05-25
CY1083A (en) 1980-12-27
IE40001B1 (en) 1979-02-14
HK56180A (en) 1980-10-10
MY8100197A (en) 1981-12-31
DK156642B (da) 1989-09-18
CH603524A5 (ja) 1978-08-15
DK477674A (ja) 1975-05-12
DE2442305C2 (de) 1986-04-03
AU7313674A (en) 1976-03-11
CH613932A5 (ja) 1979-10-31
HK56280A (en) 1980-10-10
NL175812C (nl) 1985-01-02
NL175812B (nl) 1984-08-01
FR2242972A1 (ja) 1975-04-04
CH599090A5 (ja) 1978-05-12
JPS5053359A (ja) 1975-05-12
NL7412060A (nl) 1975-03-13
JPS5890526A (ja) 1983-05-30
CH603523A5 (ja) 1978-08-15
JPS605580B2 (ja) 1985-02-12
DE2463219C2 (ja) 1988-02-04
CH603543A5 (ja) 1978-08-31
FR2242972B1 (ja) 1978-07-21
CY1082A (en) 1980-12-27
JPS6033818B2 (ja) 1985-08-05
SE7907064A0 (sv) 1979-08-23
SE7411261L (ja) 1975-03-12
CH603526A5 (ja) 1978-08-15
DK156642C (da) 1990-01-29

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