JPS58113142A - 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

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Publication number
JPS58113142A
JPS58113142A JP57190680A JP19068082A JPS58113142A JP S58113142 A JPS58113142 A JP S58113142A JP 57190680 A JP57190680 A JP 57190680A JP 19068082 A JP19068082 A JP 19068082A JP S58113142 A JPS58113142 A JP S58113142A
Authority
JP
Japan
Prior art keywords
formula
compound
manufacture
naphthalene derivative
medoxy
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.)
Granted
Application number
JP57190680A
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English (en)
Other versions
JPS5921850B2 (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)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

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島導体ば有用ｔＪ抗炎症性を有し、
種々のリウマチ性および関節炎ｒ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
す７タレン計導体のび−とりに式（Ｔ）ＣＨａ 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椋の化合物は
英国時計第１，２７１，１３２号、同絨１，２７４，２
７１号、同第１．２７４．２７２号、同第１，２７４，
２７３号、同第１，２９１，３８６号、同第１，２１１
，１３４号、　同第１、２９７．３０６号、同第１，２
７６．２６１号、同第１．２１６，８８２号、同第１．
２８９．０４１号、同第１、３２１．３４７号および同
第１．’２９６，４９３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−
Ｃｈｅｍ、　１３．２０！１、（１９７０）、Ｊ−Ｐｈ
ａｍ−Ｅｘｐ−’ｌｆ”ｈｅｒａ、１７９．　１１４、
（１９７１））に記載されている一１ 残念ながら式（Ｉ）の化合物は治療用投与■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。
本発明によって、他のナフタレンき導体が良好に基いて
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
った。この化合物は式（ＪＴ）を有する化合物である。
従って本発明の化合物は４−　（＜！、７−メドキシー
２−ナフチル）ブドー３−エンーγ−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
１００ｍ９／に９／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倍も高い投与量で冑に刺激を与え
なかった。
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
することかできる。
単位投与量を含有する形のときには通常式（ＩＴ）の薬
効成分を２０〜１１０００ｒｎ、さらに一般的には１０
０〜６００■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、７
０ｋｇの体重の人間の１日投与量が通常３００〜３００
０■、さらに好ましくは５００〜２０００ｍ９たとえば
６００〜１６００■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（ＩＩＩ　）の新しい
化合物の製法が得られる。
ａ）式（ＴＩＴ） を有する６−メドキシー２−ナフトアルデヒドを、式（
ＴＶ） Ｑ＝ＣＨＣＯＣトム　　　　　　　（ＩＶ）を有するラ
イｆ　イヒ（Ｗｉｔｂｉｇ　ｒｅａｇｅｎｔ）の反応剤
シ（式中Ｑは三賃換リン原子である）と反応させるか、
ｂ）式（Ｖ） を有する４　ｙ　（６’−メトキシ−２′−す７チル）
ブドー４−ヒドロキシ−２−オンを脱水することによっ
て式（ＩＴ）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のグループにハＰｈ５
Ｐ、　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。
６−メドキシー２−ナフトアルデヒド１．５ｇ、トリフ
ェニルアセトニルホスフィン４９、テトラヒドロフラン
２００　ｍｌを１２０時間時間下に保持した。＆ＮＨＣ
７１００ｙｄをこの混合物に添加し、更に酢酸エチル７
００ｒｎｌを添加した。有機層を分離し、水性層を酢酸
エチル（２Ｘ２００ｍｌ）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４
０３ｍｇと４−　（６１−メトキシ−２′−ナフチル）
−ブドー３−エン−２−オン１．１５　！；！が得られ
た。石油エーテル（８０〜１００°Ｃ）からの融点１２
０℃ ６−メドキシー２−す７トアルデヒド６０ｇをアセトン
５００闘中で１０％の水酸化ナトリウム水溶液１０ｍ１
と３時間かきまぜて４−（６１−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０エーテル溶液をＭｇＳ
Ｏ４で乾燥し、減圧蒸発すると固体３０．９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°Ｃの４−　（／）／−
メトキシ−２′−ナ７チル）−ブドー６−エン−２−オ
ン１５．９を得る。
参考例１　薬理学的データ 通常のアレン、トイジー試験を使用し、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（５ｔａｎｄａｒ
ｄＲａｔ　Ｐａｗ　Ｃａｒｒａｇｅｅｉｎ　Ｔｅ５ｔ　
）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Ｏ 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６００ｍ９／ｋｇ／日を経口投与して
６日後のネズミの胃に過度の刺激を与えないが、式（Ｉ
）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。
・、１ 代理人　弁理士　　秋　沢　政　光 他１名

Claims (2)

    【特許請求の範囲】
  1. （１）式（ＴＩＩ） を有する６−メドキシー２−ナフトアルデヒドを、式（
    ＴＶ） Ｑ：ＣＨＣＯＣＨ３（ＩＶ） （式中、Ｑは三置換リン原子を表す）を有するウイティ
    ヒの反応剤と反応させることを特徴とする、式（ｎ） を有する４　−（６／−メトキ多−２′−す７チル）ブ
    ドー３−エン−２−オンの製法。
  2. （２）式（Ｖ） を有する化合物を脱水することを特徴とする式（ＩＩ） を有する４　−（６’−メトキシ−２′−す７チル）ブ
    ドー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
GB4255073A GB1474377A (en) 1973-09-11 1973-09-11 Naphthalene derivatives
GB42550 1973-09-11

Publications (2)

Publication Number Publication Date
JPS58113142A true JPS58113142A (ja) 1983-07-05
JPS5921850B2 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
JP57190681A Expired JPS605580B2 (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

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
JP57190681A Expired JPS605580B2 (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

Country Status (15)

Country Link
JP (4) JPS5920655B2 (ja)
BE (1) BE819794A (ja)
CH (8) CH603524A5 (ja)
CY (2) CY1082A (ja)
DE (2) DE2463219C2 (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)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5504502A (en) * 1990-09-18 1996-04-02 Fujitsu Limited Pointing control device for moving a cursor on a display on a computer
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

Families Citing this family (12)

* 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
EP0003074B1 (en) * 1978-01-07 1981-04-15 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
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
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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
AU2003229142A1 (en) * 2002-06-07 2003-12-22 Cortical Pty Ltd Naphthalene derivatives which inhibit the cytokine or biological activity of macrophage inhibitory factor (MIF)

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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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US5504502A (en) * 1990-09-18 1996-04-02 Fujitsu Limited Pointing control device for moving a cursor on a display on a computer
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

Also Published As

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IE40001B1 (en) 1979-02-14
CH603525A5 (ja) 1978-08-15
ZA745441B (en) 1975-08-27
MY8100198A (en) 1981-12-31
CH603524A5 (ja) 1978-08-15
SE7907064L (sv) 1979-08-23
BE819794A (fr) 1975-03-11
JPS5890526A (ja) 1983-05-30
DK156642B (da) 1989-09-18
DE2442305A1 (de) 1975-03-13
FR2242972A1 (ja) 1975-04-04
AU7313674A (en) 1976-03-11
MY8100197A (en) 1981-12-31
DK477674A (ja) 1975-05-12
SE7411261L (ja) 1975-03-12
JPS605580B2 (ja) 1985-02-12
IE40001L (en) 1975-03-11
CH599090A5 (ja) 1978-05-12
JPS5920655B2 (ja) 1984-05-15
KE3082A (en) 1980-10-03
JPS5053359A (ja) 1975-05-12
CY1083A (en) 1980-12-27
CH603523A5 (ja) 1978-08-15
SE7907064A0 (sv) 1979-08-23
HK56280A (en) 1980-10-10
CY1082A (en) 1980-12-27
CH603527A5 (ja) 1978-08-15
DE2463219C2 (ja) 1988-02-04
NL175812B (nl) 1984-08-01
JPS5896036A (ja) 1983-06-07
NL7412060A (nl) 1975-03-13
KE3081A (en) 1980-10-03
JPS5921850B2 (ja) 1984-05-22
GB1474377A (en) 1977-05-25
JPS6033818B2 (ja) 1985-08-05
CH613932A5 (ja) 1979-10-31
CH603543A5 (ja) 1978-08-31
CH603526A5 (ja) 1978-08-15
NL175812C (nl) 1985-01-02
DK156642C (da) 1990-01-29
SE420598B (sv) 1981-10-19
DE2442305C2 (de) 1986-04-03
HK56180A (en) 1980-10-10
FR2242972B1 (ja) 1978-07-21

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