JP5268601B2 - イソフラボン類を含有する治療方法及び組成物 - Google Patents
イソフラボン類を含有する治療方法及び組成物 Download PDFInfo
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- JP5268601B2 JP5268601B2 JP2008309525A JP2008309525A JP5268601B2 JP 5268601 B2 JP5268601 B2 JP 5268601B2 JP 2008309525 A JP2008309525 A JP 2008309525A JP 2008309525 A JP2008309525 A JP 2008309525A JP 5268601 B2 JP5268601 B2 JP 5268601B2
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- 0 *C(*c1cc(S)cc(*)c11)C(c(cc2)ccc2O)C1=O Chemical compound *C(*c1cc(S)cc(*)c11)C(c(cc2)ccc2O)C1=O 0.000 description 5
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Description
ZはH,R1はH,若しくはRACO、ここでRAはC1-10のアルキル若しくはアミノ酸、R2はH、OH若しくはORBここでRBはアミノ酸若しくはCORA、ここでRAは前記定義と同じ、
WはH,AはH若しくはOH、Bは以下から選択される、
WとAとBがそれらが結合している官能基と一緒に以下を構成する、
WとAがそれらが結合している官能基と一緒になり以下を構成し、
Bは
ここでR3はH、CORA、ここでRAは前記定義と同じ、CO2RCここでRCはC1-10アルキル基、若しくはCORBここでRBは前記定義と同じ、
R4はH,CORDここでRDはH,OH、C1-10アルキル基若しくはアミノ酸、CO2RCここでRCは前記定義と同じ、
COREここでREはH,C1-10アルキル基若しくはアミノ酸、COOH,CORCここでRCは上記定義と同じ、又はCONHREここでREは前記定義と同じ、
R5はH,CO2RCここでRCは前記定義と同じ、若しくはCORCOREここでRCとRは前記定義と同じ、そして2個のR5はそれらが同じ若しくは異なる同じ官能基に結合している、R6はH若しくはヒドロキシC1-10アルキル基、Xは好ましくはO、しかしながらN若しくはSでもよい、そしてYは
ここでR7はH若しくはC1-10アルキル基式Iの化合物は好ましくは以下から選択される:
ここでR8はCORここでRDは前記定義と同じR9はCO2RC若しくはCOREここでRCとREは前記定義と同じR10はCORC若しくはCORCOREここでRCとREは前記定義と同じR11はH若しくはOHR12はH,COOH,CO2RCここでRCは前記定義と同じ、若しくはCONHREここでREは前記定義と同じR13はOH,ORBここでRBは前記定義と同じ、若しくはCORAここでRAは前記定義と同じR14はH、若しくはCORAここでRAは前記定義と同じR15はCORAここでRAは前記定義と同じR16はH,CORB若しくはCO2RCここでRBとRCは前記定義と同じR17はH若しくはヒドロキシC1-10アルキル基R18はH若しくはC1-10アルキル基
そして、"---" は単結合、若しくは二重結合を示す。
上記化合物のあるものは、ジヒドロダイゼイン(化合物1でR8がH),ジヒドロゲニステイン(化合物2及び5)、デヒドロ−O−デスメチルアンゴレンシン(化合物11)、テトラヒドロダイゼイン(化合物8)、エクオル及びデヒドロエクオル(化合物10)、O−デスメチル−アンゴレンシン(ODMA−化合物13)、及び6−ヒドロキシ−O−デスメチルアンゴレンシン(6−ヒドロキシ−ODMA−化合物14)
ここで、R1,R2,Z,W,A及びBは前記定義と同じで、単独若しくは薬理学的に許容しうる担体、及び・若しくは賦形剤とともに投与される。
本発明の第3の見地は、一つ以上の治療適応症の治療、改善、防御、予防及び若しくは防止に式Iの化合物の一つ以上を使用することである。式1〜19の化合物が特に好ましい。
ここで、A’はHまたはR1,ここでR1は前記定義と同じ、R8とR11とXは前記定義と同じ。化合物2、3、4、5、6、及び7はこの方法で調製される。化合物5から7は化合物2から4のエノール型である。
B:水素化ホウ素ナトリウムによるダイゼインとダイゼイン誘導体の還元は以下の通
り:
ここで、R9とXは前記定義と同じ。化合物8はこの方法で調製される。
C.パラジウム/活性炭を用いたダイゼイン及びダイゼイン誘導体の水素化
ここでR11及びR12は前記定義と同じ。化合物10はこの方法で調製される。
D.レゾルシノールまたはその誘導体のアシル化、引き続き臭素化リチウムで脱水素化
化合物11と14はこの方法で調製される。化合物12は類似の方法で調製される。
ここでR13とR15は前記定義と同じ。化合物15及び16はこの方法で調製される。
ここで、R11,R17とR18は前記定義と同じ
生成物の同定は質量分析で確認できる。式1〜19の化合物はJoannou等の方法(1995)により精製することができる。J.Steroid.Biochem.Molec.Biol.54,167-184は参照するこにより本明細書に援用する。
実施例1
ダイゼインは、Wahalaの方法(Finnish Chem.Lett.1989,16,79)に従って、レゾルシノールを4−ヒドロキシ−フェニル酢酸とを三フッカホウ素エーテル錯化合物を触媒として用いて、フリーデルクラフトアシル化反応を行い、その後DMFとメタンスルフォニルクロリドとで処理して、72%の収率で得ることができる。ゲニステインは市販されているが非常に高価である。しかしながら、レゾルシノールの代わりに1、3、5−トリヒドロキシベンゼンを用いてダイゼインと同じ方法で合成できる。
ここでRは、生成物がダイゼインのときはH、ゲニステインのときはOHである。
パラジウム/炭酸カルシウムを触媒として用いて、ダイゼイン及びゲニステインを水素化すると良い収率でジヒドロダイゼインとジヒドロゲニステインが得られる。
ここで、Rは、ジヒドロダイゼインのときはH、ジヒドロゲニステインのときはOHである。
ダイゼインを水素化ほう素ナトリウムで還元すると標題化合物が得られる。
エクオル誘導体はダイゼイン誘導体をパラジウム/活性炭を触媒として用いて水素化することにより得られる(Finnish Chem.Lett.1989,16,79)。
4−ヒドロキシフェニルイソプロピル酸を1、3、5−トリヒドロキシベンゼンでアシル化することにより標題化合物が得る。
標題化合物は、下記のようにレゾルシノールのアシル化、引き続く脱水素化により得られる。
化合物17
ここで、R11,R17、及びR18は前記定義と同じ。
化合物18
ここで、R24,R25及びR26は前記定義と同じ。
化合物19
ここで、R11,R17及びR18は前記定義と同じ。
実施例2
実施例3
1.1:2−(p−メトキシフェニル)プロピオン酸
p−メトキシプロピオフェノン(2.39g、14.5mmol)、90%酢酸鉛(IV)(6.45g,14.5mmol)、トリエチルオルト蟻酸(15ml)及び過塩素酸(1.2ml,29mmol)の混合物を18時間、55℃まで加熱した。混合物を冷却し、減圧下でトリエチルオルト蟻酸を除去した。残査をクロロホルムに溶解し、残った沈殿物を濾過し除いた。クロロホルム溶液を水で洗浄し、蒸発させて粗エステルを得た。この粗エステル生成物を10%KOH 1:1 水:メタノール溶液に溶解し、それを3時間還流した。冷却後、メタノールを減圧下に蒸発させ、水溶液をジエチルエーテル(3 x 25ml)で洗浄した。水溶液を2N硫酸で酸性にし、再び、ジエチルエーテルで洗浄した(3 x 25ml)。2回目のエーテル洗浄からのも併せた分画を硫酸ナトリウムで乾燥し、蒸発させると上記プロピオン酸が得られた(1.66g,63%)。
2−(p−メトキシフェニル)プロピオン酸(0.39g,4mmo1)と1,3−ジメトキシベンゼン(0.5g,0.5ml,4mmol)をポリリン酸(PPA)(10g)中で混合し、反応混合物を機械的に75℃で5時間撹拌した。反応混合物を室温まで冷却し、さらに12時間機械的に撹拌した。反応を氷水で止め、生成物をクロロホルムで抽出した(3 x 25ml)。クロロホルム層をNa2SO4で乾燥し溶媒を減圧下で除去した。残査粗生成物をシリカゲルカラムクロマトグラフィー(溶離液 7:2 CH2Cl2:EtOAc)で精製して純粋な2,4,4’−トリメトキシ−α−メチルデスオキシベンゾイン(0.68g,58%)を得た。
2,4,4’−トリメトキシ−α−メチルデスオキシベンゾィン(0.312g,1.04mmol)をドライCH2Cl2(10ml)に溶解した。この溶液に、ヘキサン(1.3g、5.2ml,5.2mmol)中の5当量の1.0M BBr3をゆっくり添加し、反応混合物を室温で6日間窒素雰囲気下で撹拌した。反応を氷水で停止し、1時間撹拌後ジエチルエーテルで抽出した(3 x 25ml)。エーテル層をNa2SO4で乾燥し、溶媒を減圧下に除去した。残査の粗生成物をシリカゲルカラムクロマトグラフィー(溶離液 7:1 CH2Cl2:EtOAc)で精製し、純粋な2,4,4’−トリヒドロキシフェニル−α−メチルデスオキシベンゾイン(0.68g、58%)を得た。
2.1:フロログリシノールとp−メトキシフェニルプロピオン酸との反応でPOCl3の使用
2−(p−メトキシフェニル)プロピオン酸(0.1g,0.55mmol)
と1.1当量の1,3,5−トリヒドロキシベンゼン(フロログリシノール)(0.077g,0.61mmol)を乾燥テトラヒドロフラン(THF)(2ml)に溶解した。蒸留したばかりのPOCl3をその溶液に添加し反応混合物を室温で4日間撹拌した。反応をその後氷水で停止させジエチルエーテル(3 x 10ml)で生成物を抽出した。エーテル層をNa2SO4で乾燥し溶媒を減圧下で除去した。残査の粗生成物をシリカゲルカラムクロマトグラフィー(溶離液 7:2 CH2Cl2:EtOAc)で精製し二つの生成物、即ちエステル(1)、及び目的の4’メトキシ−6−OH−ODMA(2)を得た。
が得られた。
4:テトラヒドロダイゼイン トランス/シス異性体の合成(化合物8)
4−1.テトラヒドロダイゼイン トランス/シスの合成
得られた混合物を35分間95℃まで加熱し、ベンゼンを蒸発させ、粗生成物をHPLC(メタノール/水=60:40)で精製し、デヒドロエクオルとエクオルを得た。デヒドロエクオルはHーNMR,GC−MSと高分解能MSで確認した。
還元生成物をHPLCで精製した。
実施例4
実施例5
一連の製剤は活性化合物を40−200mgの間の投与形態からなるように調製する。
この実施例のために、活性化合物1〜19のそれぞれ200mg含有するゼラチンカプセルと錠剤を上記の大豆粉基材で、若しくはコレステロールを含まないヨーグルト基材で調製する。
実施例6
ラット大動脈輪を用いた血管反応性の研究は一般的には上記状態の治療での候補化合物の生物学的効果を直接予測しうるものとみなされている(Karapapanis,S等,(1994)HePtology、20,6,1516-1521)。大動脈輪における収縮反応に対する抑制効果を血管収縮物質であるノルアドレナリンの存在下に上述のKarapapanisの操作法に従って測定する。ジヒドロダイゼイン(化合物1)、ジヒドロゲニステイン(化合物2及び5)、テトラヒドロダイゼイン(化合物8)、ODMA(化合物13)、及びエクオル(化合物10)全てがノルアドレナリンに対する反応に抑制効果を示す、即ち、それらは血管収縮反応を抑制した。引き続く臨床研究では、上記の状態の治療にこれらの化合物を用いた治療効果が得られる。
ホルモン反応性癌細胞の増殖を阻害する本発明の化合物の活性を、良く特性のわかっているヒト反応性癌細胞株K562及びHL60を用いて試験した。抗癌スクリーニングアッセイによって最終的な分化細胞死に至る細胞増殖の阻害を測定した。細胞死はODMA(化合物13)とエクオル(化合物10)、若しくは細胞株K563とHL60の増殖阻害剤によるアポトーシス若しくは壊死による。従って、この結果から、これらの化合物が上述のようなホルモン関連癌の増殖を阻害するということを直接予想できるものである。テトラヒドロダイゼイン(化合物8)は細胞株HL60に強い阻害を示した。
多くの研究が抗酸化剤活性を有する化合物が上記の状態の治療に有用な治療剤であることを示している(例えば、Mc Laughlan等(1995)Biochem.Soc.Trans.23(2)2575;van't Veer等(1996)Cancer Epidemiol Biomarkers Prev.5(6)441-7)。本発明の化合物は抗酸化剤活性を有する。
試料 ラグタイム−分 対照に対する増加%
対照 20
アスコルビン酸 50 150
テトラヒドロダイゼイン >140 >600
デヒドロエクオル >140 >600
この試験ではビタミンEの存在下でLDL脂質の酸化を抑制する化合物の能力を測定する。この試験は生理的試験であり、ビタミンE(α−トコフェロール)は血流中にLDLとともに存在し、LDL酸化は動脈硬化の進展の主要な因子の一つと考えられている。この値が低ければ低いほど、レドックス活性が高い。高いレドックス活性は、その化合物が恐らくα−トコフェロキシラジカルを還元することによりLDLのα−トコフェロールと相互作用することができるということを示している。この試験は間接的に緩和な、化学的に調節された酸化を受けながらヒトLDL中のα−トコフェロールと相乗作用する化合物の能力を測定する。酸化を内因性のα−トコフェロールが20%消費された時点でのコレステロールエステルヒドロパーオキシドの蓄積で測定する。ブチル化ヒドロキシトルエン(BHT10μM)を陽性対照として用いる。レドックス指標は、試料の存在下にLDLの酸化の相対的な程度を試験化合物が存在しないときの相対的な酸化の程度で除したものにより測定する。活性化合物は低いレドックス指標を与える。試験はBowry,V.W.等(1995) J.Bio.Chem.270(11)5756-5763に従って行った。そのような試験は化合物1〜19が同調的にビタミンEと相互作用して脂質、蛋白質及び他の生物学的物質の酸化を抑制することを示している。
この試験はセチルトリメチル塩化アンモニウム(HTAC)若しくはSDSミセル中でα−トコフェロールを減衰させる試験試料の能力を測定するものである。アスコルビン酸を陽性対照に用いる。結果は、試験試料存在下のα−トコフェロールラジカルの相対的分解速度常数を試験試料の存在しない場合のα−トコフェロールラジカルの相対的分解速度常数で除したものとして表される。TRAA測定単位は相乗活性が低いと考えられており、一方、活性化合物が混合すると直ぐにα−トコフェロキシラジカルを除去するので大きな値を示す。
この研究によって、LDLレセプターを上流制御する化合物は循環LDLを減少させ、従って、動脈硬化、心筋梗塞、発作及び高血圧の可能性を減少させることを確立されるであろう。Stephan Z.F.とYurachek,E.C.(1993)J.Lipid Res.
34,325-330に従ったアッセイを利用して、式1〜19の化合物がLDLの肝細胞への取り込みを増加させ、これが、ヒト血流中の循環LDLの現象を直接予測させるものであることを示している。ODMAとエクオルは特にこの点に関して活性である。
実施例7
思春期以来アクネで、避妊ピル若しくはどの局所クリームにも反応しない18歳の少女が、安全の見地からややもするとロアクタンを使っていたが、尿分析で証明されているように代謝物、即ち化合物1、2、5、8、10、11、13と14に変換されるゲニステイン、ダイゼイン、ホルムオノネチンやビオカイン−Aを含有する大豆イソフラボンが投与された。一日40mg2回投与された結果アクネの状態、色及び全身状態が2週間で著しく改善された。
実施例8
実施例9
実施例10
実施例11
本発明はその精神及び範囲内であるそのような変化及び修飾を全て含むものであることは理解されるべきことである。本発明は本明細書に言及され、示された全てのステップ、特徴、組成物、化合物を個々に、若しくは集合的に、そして当該ステップ、若しくは特徴のいずれの2以上のどのような、及び全ての組み合わせをも含むものである。
Claims (10)
- 高血圧、動脈硬化、心筋梗塞、発作、又は日光誘導皮膚傷害を治療、予防、改善、防御及び/又は防止用の薬剤を製造するための化合物の使用であって、
上記化合物は、下記式(10)の化合物を有効成分として含む、薬剤を製造するための化合物の使用。
ここで、
R11はH、
R12はHであり、
そして、“−−−”は単結合又は二重結合を示す。 - 上記式(10)の化合物は、下記式(10’)の化合物である、請求項1記載の薬剤を製造するための化合物の使用。
(10’)
- さらに薬学的に許容できる担体又は賦形剤を含んでなる請求項1又は2記載の薬剤を製造するための化合物の使用。
- 下記式(10)又は(10’)の化合物を含む、高血圧、動脈硬化、心筋梗塞、発作、及び日光誘導皮膚傷害からなる群から選択される1又は複数の治療適応症の治療、予防、改善、防御及び/若しくは防止用の薬剤。
(10’)
ここで、
R11はH、
R12はHであり、
そして、“−−−”は単結合又は二重結合を示す。 - 1又は複数の治療適応症が動脈硬化である、請求項4記載の薬剤。
- 単位投与、注射、又は局所投与の剤型である、請求項4又は5に記載の薬剤。
- 上記化合物が0.1mgから2gの範囲の量である、請求項6に記載の単位投与剤型の薬剤。
- 上記化合物が50mgから200mgの範囲の量である、請求項6に記載の単位投与剤型の薬剤。
- 下記式(10’)の化合物と薬理学的及び/若しくは化粧品学的に許容できる担体及び/若しくは賦形剤とを含む抗酸化組成物。
(10’) - 下記式(10’)の化合物を含有する固体投与単位組成物を含む、請求項9記載の組成物。
(10’)
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