JP2018184452A - 置換アシルアニリドおよびそれらの使用方法 - Google Patents
置換アシルアニリドおよびそれらの使用方法 Download PDFInfo
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- JP2018184452A JP2018184452A JP2018140123A JP2018140123A JP2018184452A JP 2018184452 A JP2018184452 A JP 2018184452A JP 2018140123 A JP2018140123 A JP 2018140123A JP 2018140123 A JP2018140123 A JP 2018140123A JP 2018184452 A JP2018184452 A JP 2018184452A
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Abstract
Description
[00020]米国(US)では、腎不全の発生率および有病率が上昇している。末期腎疾患(ESRD)Medicare設立プログラムに登録された患者数は、1973年に約10,000人の受給者から、1983年に86,354人、そして2002年12月31日現在431,284人へと増加した。2002年だけで、100,359人の患者が、US ESRDプログラムの一員となった。慢性腎疾患(CKD)は、ESRDの前兆であり、腎臓が体内から老廃物を十分に除去することができない場合に生じる。CKDは、徐々に進行する疾患であり、この場合、糖尿病、高血圧症および貧血が、共存状態でありうる。
[00023]熱傷は、テストステロン減少、窒素レベル減少および骨密度(BMD)の減少を引き起こし、それは、傷害後1年の長期間も持続することがありうるし、しかも創傷治癒障害、感染リスク増加、除脂肪体重の低下、リハビリテーション阻害、および熱傷生存者の社会復帰遅延に関連している。熱傷の結果として開始する異化作用は、有意の不随意体重減少をもたらして、問題を更に複雑にする。
[00027]一つの態様において、本発明は、式(I):
[00028]一つの態様において、本発明は、式S−(I):
[00029]一つの態様において、本発明は、式R−(I):
[00036]一つの態様において、本発明は、雄性対象の避妊方法であって、その対象に、式(I)の選択的アンドロゲン受容体モジュレーター化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、水和物、N−オキシドまたはいずれかそれらの組合せ、またはそれを含む組成物を、対象の精子生産を抑制することによって対象に避妊を行う有効量で投与する工程を含む方法を提供する。
[00038]一つの態様において、本発明は、ホルモン療法の方法であって、対象のアンドロゲン受容体と、式(I)の選択的アンドロゲン受容体モジュレーター化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、水和物、N−オキシドまたはいずれかそれらの組合せ、またはそれを含む組成物とを、アンドロゲン依存状態を変化させる有効量で接触させる工程を含む方法を提供する。一つの態様において、式Iの化合物は、式S−(I)を有する構造で表され、または一つの態様において、式Iの化合物は、式R−(I)を有する構造で表される。
[00049]一つの態様において、本発明は、ヒト対象の高インスリン血症を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる方法であって、その対象に、有効量の式(I)の化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、N−オキシド、水和物またはいずれかそれらの組合せを投与する工程を含む方法を提供する。
[00051]一つの態様において、本発明は、ヒト対象のインスリン抵抗性を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる方法であって、その対象に、有効量の式(I)の化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、N−オキシド、水和物またはいずれかそれらの組合せを投与する工程を含む方法を提供する。
[00053]一つの態様において、本発明は、糖尿病に関連した疾患を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる方法であって、その対象に、有効量の式(I)の化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、N−オキシド、水和物またはいずれかそれらの組合せを投与する工程を含む方法を提供する。一つの態様において、式Iの化合物は、式S−(I)を有する構造で表され、または一つの態様において、式Iの化合物は、式R−(I)を有する構造で表される。
[00059]一つの態様において、本発明は、対象の脂肪質量を減少させる方法であって、その対象に、有効量の式(I)の化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、N−オキシド、水和物またはいずれかそれらの組合せを投与する工程を含む方法を提供する。
[00061]一つの態様において、本発明は、対象の除脂肪質量を増加させる方法であって、その対象に、有効量の式(I)の化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、N−オキシド、水和物またはいずれかそれらの組合せを投与する工程を含む方法を提供する。
[00063]別の態様において、本発明は、精子形成を抑制する;雄性の避妊;ホルモン療法;前立腺癌を処置する;前立腺癌の進行を遅延させる;対象の骨関連障害を処置するまたは対象の骨質量を増加させるおよび/または対象の骨形成を促進する;筋消耗障害を処置する、その発生率を減少させる、その進行を遅延させる、その重症度を減少させる、またはそれに関連した症状を減少させる;糖尿病を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;グルコース不耐症を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;高インスリン血症を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;インスリン抵抗性を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;糖尿病に関連した疾患を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;脂肪肝状態を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;心臓血管疾患を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;悪液質を処置する、その重症度を減少させる、その発生率を減少させる、その開始を遅延させる、またはその病原を減少させる;眼の疾患または状態を処置する;脂肪質量を減少させる;または対象の除脂肪質量を増加させる方法であって、本明細書中に記載のように対象に、有効量の式(I)の化合物またはその異性体、薬学的に許容しうる塩、医薬製品、結晶、N−オキシド、水和物またはいずれかそれらの組合せを投与する工程を含む方法を提供する。
[00074]次の詳細な説明において、多くの具体的な詳細は、本発明について十分な理解を与えるために示している。しかしながら、本発明を、これら具体的な詳細を伴うことなく行うことができるということは、当業者に理解されるであろう。他の場合、周知の方法、手順および成分は、本発明を不明確にしないように、詳細に記載しなかった。
[00079]一つの態様において、本発明は、式S−(I):
[00087]式Iのアミンの適する薬学的に許容しうる塩は、無機酸からまたは有機酸から製造することができる。一つの態様において、アミンの無機塩の例は、重硫酸塩、ホウ酸塩、臭化物、塩化物、半硫酸塩、臭化水素酸塩、塩酸塩、2−ヒドロキシエチルスルホン酸塩(ヒドロキシエタンスルホン酸塩)、ヨウ素酸塩、ヨウ化物、イソチオン酸塩、硝酸塩、過硫酸塩、リン酸塩、硫酸塩、スルファミン酸塩、スルファニル酸塩、スルホン酸(アルキルスルホン酸塩、アリールスルホン酸塩、ハロゲン置換アルキルスルホン酸塩、ハロゲン置換アリールスルホン酸塩)、スルホン酸塩およびチオシアン酸塩である。
[00098]一つの態様において、「ハロゲン」という用語は、一つの態様において、F、別の態様において、Cl、別の態様において、Br、別の態様において、Iを意味する。「アリールアルキル」基は、別の態様において、アリールに結合したアルキルを意味し、ここにおいて、アルキルおよびアリールは、上に定義の通りである。アリールアルキル基の例は、ベンジル基である。
[000101]本発明は、それら化合物の誘導体を提供する。一つの態様において、「誘導体」には、エーテル誘導体、酸誘導体、アミド誘導体、エステル誘導体等が含まれるが、これに制限されるわけではない。別の態様において、本発明は、更に、それら化合物の水和物を包含する。
[000103]本発明は、他の態様において、それら化合物の代謝産物を提供する。一つの態様において、「代謝産物」とは、代謝または代謝過程によって別の物質から生じるいずれかの物質を意味する。
[000107]一つの態様において、式IのSARM化合物は、本明細書中に示されるような方法によって、更には、当業者に知られているであろうように製造することができる。
(a)式17:
(b)式R−19のアミドと、式20:
[000110]一つの態様において、工程(a)の化合物R−18を、カップリング剤と反応させた後、式17の化合物を加える。
[000112]別の態様において、本明細書中に上に概説された方法の工程(b)の条件は、炭酸カリウム、炭酸ナトリウムまたは炭酸セシウム、または2−プロパノール、THFまたはメチルエチルケトンを溶媒として用い、場合により、転移触媒、BTBAC(ベンジルトリブチルアンモニウムクロリド)または他の適する物質を含むこの反応に適当な別の塩基を含んでよい。
(a)式17:
(b)式S−19のアミドと、式20
[000114]一つの態様において、工程(a)の化合物S−18を、カップリング剤と反応させた後、式17の化合物を加える。
[000116]別の態様において、本明細書中に上に概説された方法の工程(b)の条件は、炭酸カリウム、炭酸ナトリウムまたは炭酸セシウム、または2−プロパノール、THFまたはメチルエチルケトンを溶媒として用い、場合により、転移触媒、BTBAC(ベンジルトリブチルアンモニウムクロリド)または他の適する物質を含むこの反応に適当な別の塩基を含んでよい。
(a)式17:
(b)式R−19のアミドと、塩基とを反応させて、オキシランS−21
(c)式S−21のオキシランと、式20:
[000118]一つの態様において、それによって、工程(a)の化合物R−18を、カップリング剤と反応させた後、式17の化合物を加える。
[000120]別の態様において、本発明は、式R−(I):
(a)式17:
(b)式S−19のアミドと、塩基とを反応させて、オキシランS−21
(c)式S−21のオキシランと、式20
[000121]一つの態様において、それによって、工程(a)の化合物S−18を、カップリング剤と反応させた後、式17の化合物を加える。
[000123]別の態様において、本発明は、式S−(I)
(a)式S−22
(a)式R−23の化合物を開環して、式S−24
式S−24の化合物のカルボン酸と、式17
[000124]図1Eは、式S−(I)の化合物のこのような製造方法の態様を示す。
(a)式R−22
(b)式S−23の化合物を開環して、式R−24
式R−24の化合物のカルボン酸と、式17
[000126]図1Fは、式R−(I)の化合物のこのような製造方法の態様を示す。
(a)式R−18
(b)式R−26の化合物を開環して、式S−24
式S−24の化合物のカルボン酸と、式17
[000128]図1Gは、式S−(I)の化合物のこのような製造方法の態様を示す。
(a)式S−18
式S−26の化合物を開環して、式R−24
式R−24の化合物のカルボン酸と、式17:
[000130]図1Hは、式R−(I)の化合物のこのような製造方法の態様を示す。
(a)式24
を有する化合物とを反応させて、式28aまたは式28b
(b)式28aまたは式28bのオキサゾリジンジオンまたは2−チオキソオキサゾリド−4−オンを、塩基の存在下で開環して、式(I)の化合物を生じる工程を含む方法を提供する。
[000133]別の態様において、本発明は、式(I):
(a)メタクリル酸を塩素化し、
(c)式29のアミドを酸化して、式21
(d)式21のオキシランと、式20
[000134]別の態様において、工程(c)の式29のアミドの酸化は、オゾンを含む。別の態様において、酸化剤は、ペルオキシ酸、例えば、過酢酸(CH3COOOH)である。別の態様において、酸化剤は、メタクロロ過安息香酸(m−CPBA)である。別の態様において、酸化剤は、マグネシウムモノペルオキシフタル酸(MagnesiumMonoPeroxyPthalicAcis)(MMPP)である。別の態様において、酸化剤は、触媒量(1.0〜0.1mol%)のマンガン(2+)塩と一緒の過酸化水素である。
[000136]一つの態様において、本発明は、本発明の化合物の純粋な鏡像異性体を製造する方法であって、(a)本発明の化合物のラセミ混合物を製造し;そして(b)それらラセミ混合物から本発明の純粋な化合物を分離する工程を含む方法を提供する。
いろな結晶化が含まれる。別の態様において、本発明のラセミ化合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、ラセミ体混合物と別のキラル基とを反応させ、ジアステレオマー混合物を形成後、ジアステレオマーの分離を行い、そして追加したキラル基を除去して、純粋な鏡像異性体を得ることを含む。別の態様において、本発明の化合物のラセミ混合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、キラル合成を含む。別の態様において、本発明の化合物のラセミ混合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、生物学的分割を含む。別の態様において、本発明の化合物のラセミ混合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、酵素的分割を含む。別の態様において、本発明の化合物のラセミ混合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、キラル固定相を用いたクロマトグラフィー分離を含む。別の態様において、本発明の化合物のラセミ混合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、アフィニティークロマトグラフィーを含む。別の態様において、本発明の化合物のラセミ混合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、キャピラリー電気泳動を含む。別の態様において、本発明の化合物のラセミ混合物からの光学活性な(R)異性体または(S)鏡像異性体の分離は、キラル炭素のヒドロキシル基のエステル基を、光学活性な酸、例えば、(−)−カンファン酸で形成し、そのようにして得られたジアステレオマーエステルを、分別結晶化または好ましくは、フラッシュクロマトグラフィーによって分離後、別々のエステルを各々加水分解してアルコールにすることを含む。
[000149]若干の態様において、本明細書中に記載の化合物は、単独でかまたは組成物として、男性および女性において、性腺機能低下、骨量減少、勃起障害、リビドー欠乏、骨粗鬆症および生殖能力などのいろいろなホルモン関連状態の処置に有用である。若干の態様において、本明細書中に記載の化合物は、特に、赤血球生成、骨形成、筋成長、グルコース取込み、インスリン分泌を促進すること、および/または脂質形成、凝固、インスリン抵抗性、アテローム性動脈硬化症、破骨活性およびその他を予防することを含めた、本明細書中に記載の状態の処置を引き続き生じるいろいろな過程への機能を刺激するまたは促進するまたは回復する場合に有用である。
[000151]若干の態様において、本発明は、記載の化合物を含む組成物を投与することを含む使用方法を提供する。本明細書中で用いられる「医薬組成物」は、「治療的有効量」の活性成分、すなわち、薬学的に許容しうる担体または希釈剤と一緒の式Iの化合物を意味する。本明細書中で用いられる「治療的有効量」は、ある一定の状態および投与計画に治療的作用を与えるその量を意味する。
[000164]適する賦形剤および担体は、本発明の態様により、固形または液状であってよく、そのタイプは、概して、用いられている投与タイプに基づいて選択される。リポソームは、組成物を送達するのに用いることもできる。適する固形担体の例には、ラクトース、スクロース、ゼラチンおよび寒天が含まれる。経口剤形は、適する結合剤、滑沢剤、希釈剤、崩壊剤、着色剤、着香剤、流動誘導剤および溶融剤を含有してよい。液状剤形は、例えば、適する溶媒、保存剤、乳化剤、懸濁化剤、希釈剤、甘味剤、増粘剤および溶融剤を含有してよい。非経口および静脈内の形は、更に、選択された注射またはデリバリーシステムのタイプとそれらを適合性にする鉱物または他の物質を包含すべきである。当然ながら、他の賦形剤を用いることもできる。
(1984) を参照されたい)。他の制御放出システムは、Langer(Science249:1627-1633(1990))によって概説に論じられている。
ミフェン(toremifene)、オスペミフェン(ospemifene)、ドロロキシフェン(droloxifene)、ラロキシフェン、アルゾキシフェン(arzoxifene)、バゼドキシフェン(bazedoxifene)、PPT(1,3,5−トリス(4−ヒドロキシフェニル)−4−プロピル−1H−ピラゾール)、DPN(ジアリールプロピオニトリル)、ラソフォキシフェン(lasofoxifene)、ピペンドキシフェン(pipendoxifene)、EM−800、EM−652、ナフォキシジン(nafoxidine)、ジンドキシフェン(zindoxifene)、テスミリフェン(tesmilifene)、ミプロキシフェン(miproxifene)ホスフェート、RU58,688、EM139、ICI164,384、ICI182,780、クロミフェン(clomiphene)、MER−25、ジエチルスチベストロル(diethylstibestrol)、クメストロル(coumestrol)、ゲニステイン(genistein)、GW5638、LY353581、ズクロミフェン(zuclomiphene)、エンクロミフェン(enclomiphene)、デルマジノンアセテート(delmadinoneacetate)、DPPE、(N,N−ジエチル−2−{4−(フェニルメチル)−フェノキシ}エタンアミン)、TSE−424、WAY−070、WAY−292、WAY−818、シクロコムノル(cyclocommunol)、プリナベレル(prinaberel)、ERB−041、WAY−397、WAY−244、ERB−196、WAY−169122、MF−101、ERb−002、ERB−037、ERB−017、BE−1060、BE−380、BE−381、WAY−358、[18F]FEDNP、LSN−500307、AA−102、Banzhilian、CT−101、CT−102、VG−101などのSERM;ロイプロリド、ゴセレリン、トリプトレリン(triptorelin)、アルファプロストル(alfaprostol)、ヒストレリン(histrelin)、デチレリクス(detirelix)、ガニレリクス(ganirelix)、アンチドイツレリクス(antideiturelix)、セトロレリクス(cetrorelix)、ラモレリクス(ramorelix)、ガニレリクス、アンタレリクス(antarelix)、テベレリクス(teverelix)、アバレリクス(abarelix)、オザレリクス(ozarelix)、スフゴリクス(sufugolix)、プラザレリクス(prazarelix)、デガレリクス(degarelix)、NBI−56418、TAK−810、アシリン(acyline)などのGnRHアゴニストまたはアンタゴニスト;FSHアゴニスト/アンタゴニスト、LHアゴニスト/アンタゴニスト、レトロゾール、アナストラゾール、アタメスタン(atamestane)、ファドロゾール(fadrozole)、ミナメスタン(minamestane)、エクセメスタン、プロメスタン(plomestane)、リアロゾール(liarozole)、NKS−01、ボロゾール(vorozole)、YM−511、フィンロゾール(finrozole)、4−ヒドロキシアンドロステンジオン、アミノグルエチミド(aminogluethimide)、ログレチミド(rogletimide)などのアロマターゼ阻害剤;ZK−216348、ZK−243149、ZK−243185、LGD−5552、ミフェプリストン、RPR−106541、ORG−34517、GW−215864X、Sesquicillin、CP−472555、CP−394531、A−222977、AL−438、A−216054、A−276575、CP−394531、CP−409069、UGR−07などのステロイド性または非ステロイド性グルココルチコイド受容体リガンド;ステロイド性または非ステロイド性プロゲステロン受容体リガンド;フルタミド(flutamide)、ヒドロキシフルタミド、ビカルタミド(bicalutamide)、ニルタミド(nilutamide)などのステロイド性または非ステロイド性ARアンタゴニスト、ヒドロキシステロイドデヒドロゲナーゼ阻害剤、ベザフィブラート(bezafibrate)、フェノフィブラート(fenofibrate)、ジェムフィブロジル(gemfibrozil)などのPPARαリガンド;ダルグリタゾン(darglitazone)、ピオグリタゾン(pioglitazone)、ロシグリタゾン(rosiglitazone)、イサグリタゾン(isaglitazone)、リボグリタゾン(rivoglitazone)、ネトグリタゾン(netoglitazone)などのPPARγリガンド;ナベグリタザル(naveglitazar)、ファルグリタザル(farglitazar)、テサグリタザル(tesaglitazar)、ラガグリタザル(ragaglitazar)、オキセグリタザル(oxeglitazar)、PN−2034、PPARδなどの二重作用性PPARリガンド;17−ケトレダクターゼ阻害剤、3β−DHΔ4,6−イソメラーゼ阻害剤、3β−DHΔ4,5−イソメラーゼ阻害剤、17,20デスモラーゼ阻害剤、p450c17阻害剤、p450ssc阻害剤、17,20−リアーゼ阻害剤またはそれらの組合せを含めた別の治療的化合物を含むであろう。
て、抗癌化学療法薬は、アナストラゾール、エクセメスタンまたはレトロゾールなどがあるがそれに制限されるわけではないアロマターゼ阻害剤である。
tamycin)およびネトロプシンなどの物質も、本発明の化合物と医薬組成物中で組み合わせることができる。アシクロビル、アデニン、β−1−D−アラビノシド、アメトプテリン、アミノプテリン、2−アミノプリン、アフィジコリン、8−アザグアニン、アザセリン、6−アザウラシル、2’−アジド−2’−デオキシヌクレオシド(deoxynucliosides)、5−ブロモデオキシシチジン、シトシン、β−1−D−アラビノシド、ジアゾオキシノルロイシン、ジデオキシヌクレオシド、5−フルオロデオキシシチジン、5−フルオロデオキシウリジン、5−フルオロウラシル、ヒドロキシ尿素および6−メルカプトプリンなどのDNA塩基類似体も、本発明の化合物との組合せ療法で用いることができる。クーママイシン、ナリジクス酸、ノボビオシンおよびオキソリン酸などのトポイソメラーゼ阻害剤、コルセミド、コルヒチン、ビンブラスチンおよびビンクリスチンを含めた細胞分裂阻害剤;およびアクチノマイシンD、α−アマニチンおよび他の真菌アマトキシン、コルジセピン(3’−デオキシアデノシン)、ジクロロリボフラノシル、ベンゾイミダゾール、リファンピシン、ストレプトバリシンおよびストレプトリジギンを含めたRNA合成阻害剤も、本発明の化合物と組み合わせて、医薬組成物を提供することができる。
非特異的免疫刺激因子は、Hunter's TiterMax である。一つの態様において、非特異的免疫刺激因子は、アルミニウム塩アジュバントである。一つの態様において、非特異的免疫刺激因子は、ニトロセルロース吸着タンパク質である。一つの態様において、非特異的免疫刺激因子は、GerbuAdjubantである。
アジド、HydroDIURIL(登録商標)、HYDROFLUMETHIAZIDE、Hydromox(登録商標)、Hygroton(登録商標)、インダパミド、Lozol(登録商標)、メチクロチアジド、メトラゾン、Mykrox(登録商標)、Naqua(登録商標)、Naturetin(登録商標)、Oretic(登録商標)、ポリチアジド、キネタゾン、Renese(登録商標)、トリクロルメチアジド、ジパミド(xipamide)またはZaroxolyn(登録商標)が含まれるが、これ
に制限されるわけではない。若干の態様において、ループ利尿薬には、フロセミド/フルセミド、ブメタニドまたはトラセミド(torasemide)が含まれるが、これに制限されるわけではない。若干の態様において、カリウム保持性利尿薬には、アミロリド(amiloride)、トリアムテレン、アルドステロンアンタゴニストまたはスピロノラクトンが含まれるが、これに制限されるわけではない。
Clまたはエゼチミベ(ezetimibe)などの高コレステロール血症薬である。
障害処置薬は、ベカプレルミン(becaplermin)、エタネルセプト(etanercept)、デニロイキン・ディフティトクス(denileukin diftitox)またはボツリヌス毒素などのタンパク質またはリコンビナントタンパク質である。一つの態様において、皮膚科障害処置薬は、カプサイシン、アントラリン(anthralin)、過酸化ベンゾイルまたはカルシポトリエン(calcipotriene)である。
サンプレナビル(fosamprenavir)またはチプラナビル(tipranavir)が含まれるが、これに制限されるわけではない。一つの態様において、抗ウイルス薬は、エンフビルチドなどの融合阻害剤である。一つの態様において、抗ウイルス薬または抗レトロウイルス薬の組合せが望まれる。一つの態様において、抗ウイルス薬または抗レトロウイルス薬またはそれらの組合せは、更に、ヒドロキシ尿素、レスベラトロール(resveratrol)、グレープフルーツ、リトナビル、レフルノミド(leflunomide)またはそれらの組合せを含む。
、成長ホルモン放出因子およびその類似体または成長ホルモンおよびその類似体と一緒に、またはクロニジンなどのα−アドレナリン受容体アゴニストまたはスマトリプタン(sumatriptan)などのセロトニン5−HTDアゴニスト、またはフィゾスチグミンおよびピリドスチグミン(pyridostigmine)などの、ソマトスタチンまたはその放出を阻害する物質と一緒に含んでよい。若干の態様において、消耗疾患処置薬は、副甲状腺ホルモン、PTH(1−34)、またはMK−217(アレンドロネート)などのビスホスホネートを含んでよい。他の態様において、消耗疾患処置薬は、更に、エストロゲン、タモキシフェンまたはラロキシフェンなどの選択的エストロゲン受容体モジュレーター、またはEdwards,J. P. etal., Bio. Med. Chem. Let., 9, 1003-1008(1999) および Hamann, L.G. et al.,J. Med.Chem., 42,210-212(1999) に開示されたものなどの他のアンドロゲン受容体モジュレーターを含んでよい。若干の態様において、消耗疾患処置薬は、更に、レボノルゲストレル(levonorgestrel)、メドロキシプロゲステロンアセテート(MPA)などのプロゲステロン受容体アゴニスト(「PRA」)を含んでよい。若干の態様において、消耗疾患処置薬には、米国特許第5,179,080号に記載のものなどの栄養サプリメントが含まれてよく、それは、他の態様において、乳清タンパク質またはカゼイン、アミノ酸(ロイシン、分岐状アミノ酸およびヒドロキシメチルブチレートなど)、トリグリセリド、ビタミン(例えば、A、B6、B12、フォレート、C、DおよびE)、鉱物(例えば、セレン、マグネシウム、亜鉛、クロム、カルシウムおよびカリウム)、カルニチン、リポ酸、クレアチン、β−ヒドロキシ−β−メチルブチレート(Juven)および補酵素Qとの組合せである。一つの態様において、消耗疾患処置薬は、更に、抗吸収薬、ビタミンD類似体、元素カルシウムおよびカルシウムサプリメント、カテプシンK阻害剤、MMP阻害剤、ビトロネクチン受容体アンタゴニスト、Src SH2アンタゴニスト、液胞型−H+−ATPアーゼ阻害剤、イプリフラボン、フッ化物、チボロン、プロスタノイド、17−βヒドロキシステロイドデヒドロゲナーゼ阻害剤およびSrcキナーゼ阻害剤を含んでよい。
[000363]本発明の化合物は、若干の態様において、経口テストステロン補充療法に有用でありうる。他の態様において、適当に置換された化合物は、(a)男性用避妊;(b)いろいろなホルモン関連状態、例えば、疲労、うつ病、リビドー低下、性機能不全、勃起障害、性腺機能低下、骨粗鬆症、毛髪減少、肥満、骨量減少、オステオペニア、良性前立腺増殖症、および気分および認知の変調などのADAMに関連した状態の処置;(c)性機能不全、性欲低下、性腺機能低下、骨量減少、オステオペニア、骨粗鬆症、認知および気分の変調、うつ病、貧血、毛髪減少、肥満、子宮内膜症、乳癌、子宮癌および卵巣癌などのADIFに関連した状態の処置;(d)慢性筋消耗の処置および/または予防;(e)前立腺癌の処置、前立腺癌の画像化、前立腺癌の発生率を減少させること、前立腺癌を停止させるまたは退行させること;(f)I型糖尿病の処置;(g)II型糖尿病の処置;(h)糖尿病を抑制すること、阻止することまたはその発生率を減少させること;(i)グルコース不耐症の処置;(j)高インスリン血症の処置;(k)インスリン抵抗性の処置;(l)糖尿病性腎症の処置;(m)糖尿病性ニューロパシーの処置;(n)糖尿病性網膜症の処置;(o)脂肪肝状態の処置;(p)悪液質の処置;(q)経口アンドロゲン補充および/または、本明細書中の「処置すること」という用語によって包含されるいずれかの態様を含めた他の臨床治療的および/または診断的分野に有用である。
新生物、菌状息肉腫、骨髄異形成症候群、骨髄増殖性障害、鼻咽喉癌、神経芽細胞腫、口咽頭癌、骨肉腫、卵巣上皮癌、卵巣胚細胞腫瘍、卵巣低悪性可能性腫瘍、膵臓癌、外分泌、膵臓癌、島細胞癌、副鼻腔および鼻腔癌、副甲状腺癌、陰茎癌、クロム親和性細胞腫癌、下垂体癌、形質細胞新生物、前立腺癌、黄紋筋肉腫、直腸癌、腎細胞癌、唾液腺癌、Sezary症候群、皮膚癌、皮膚T細胞リンパ腫、皮膚癌、カポジ肉腫、皮膚癌、黒色腫、小
腸癌、軟組織肉腫、軟組織肉腫、精巣癌、胸腺腫、悪性甲状腺癌、尿道癌、子宮癌、肉腫、小児期の特異癌、膣癌、外陰癌、ウィルムス腫瘍またはいずれかそれらの組合せを含む。
モン、副甲状腺ホルモン、副甲状腺ホルモン関連ペプチド、アクチビン、インヒビン、フォリスタチン、フリズルド(frizzled)、フルズブ(frzb)またはフラズルド(frazzled)タンパク質などのホルモン;コーディン(chordin)およびフェチュインなどのBMP結合タンパク質;IL−3、IL−7、GM−CSFなどのサイトカイン;エオタキシンなどのケモカイン;コラーゲン、オステオカルシン、オステオネクチンおよびその他を含んでよい。
[000405]一つの態様において、本発明は、(1)筋消耗障害を処置する;(2)筋消耗障害を予防する;(3)筋消耗障害による筋減少を処置する、予防する、抑制する、阻害するまたは減少させる;(4)筋消耗障害による筋消耗を処置する、予防する、阻害する、減少させるまたは抑制する;および/または(5)筋消耗障害による筋タンパク質異化作用を処置する、予防する、阻害する、減少させるまたは抑制する;および/または末期腎疾患またはCKDによる筋消耗を処置する、予防する、阻害する、減少させるまたは抑制する;および/または(6)虚弱を処置する、予防する、阻害する、減少させるまたは抑制するための、本明細書中に記載の化合物またはそのプロドラッグ、類似体、異性体、代謝産物、誘導体、薬学的に許容しうる塩、医薬製品、多形、結晶、不純物、N−オキシド、水和物またはいずれかそれらの組合せの使用を提供する。
[000413]筋ジストロフィーは、運動を制御する骨格筋または随意筋の進行性衰弱および変性を特徴とする遺伝的疾患である。心筋および若干の他の不随意筋も、若干の形の筋ジストロフィーにおいて影響される。筋ジストロフィー(MD)の主な形は、デュシェーヌ筋ジストロフィー、筋緊張性ジストロフィー、デュシェーヌ筋ジストロフィー、ベッカー筋ジストロフィー、肢帯筋ジストロフィー、顔面肩甲上腕筋ジストロフィー、先天性筋ジストロフィー、眼咽頭筋ジストロフィー、遠位筋ジストロフィーおよびエメリー・ドライフス筋ジストロフィーである。
[000422]一つの態様において、本発明は、対象の消耗疾患、障害または状態の処置のための、本明細書中に記載のSARM化合物またはそのプロドラッグ、類似体、異性体、代謝産物、誘導体、薬学的に許容しうる塩、医薬製品、多形、結晶、不純物、N−オキシド、水和物またはいずれかそれらの組合せの使用を提供する。
[000424]本発明は、若干の態様において、筋消耗、体重減少、栄養失調、飢餓、またはいずれかの消耗または組織質量減少による機能性減少に反映されることがありうるいずれかの消耗障害を処置することに関する。
[000437]若干の態様において、中枢神経系疾患は、アルツハイマー病、クモ膜炎、脳膿瘍、脳虚血、中枢神経系感染、脳性麻痺、脳血管障害、大脳皮質基底核神経節変性(CBGD)、Creutzfeldt-Jakob症候群、ダンディー・ウォーカー症候群、痴呆、脳炎、脳脊髄炎、癲癇、癲癇で誘発される性腺機能低下および/または代謝亢進状態、本態性振戦、フリードライヒ運動失調、ゲルストマン・シュトロイスラー・シャインカー病、ハレルフォルデン・シュパッツ症候群、ハンチントン病、脳水腫、低酸素症、不眠症、虚血性発作、クールー、ランドー・クレッフナー症候群、レヴィ小体病、マシャド・ジョセフ病、メージ症候群、髄膜炎、細菌性髄膜炎、ウイルス性、片頭痛障害、運動障害、多系統萎縮、脊髄炎、オリーブ橋小脳萎縮、パーキンソン病、パーキンソン障害、ポリオ、ポリオ後症候群、プリオン病、偽脳腫瘍、シャイ・ドレーガー症候群、攣縮、乳児性、脊髄疾患、核上麻痺、脊髄空洞症、視床疾患、チック障害、トゥーレット症候群またはブドウ膜・髄膜・脳炎症候群を含む。若干の態様において、中枢神経系疾患は、嚢胞性線維症で誘発される性腺機能低下状態である。
[000439]若干の態様において、中枢神経系疾患は、中枢神経系(CNS)への傷害または損傷を含む。若干の態様において、CNSへの傷害または損傷は、筋消耗障害に関連していてよい。CNSへの傷害または損傷は、例えば、疾患、外傷または化学薬品によって引き起こされることがありうる。例は、中枢神経傷害または損傷、末梢神経傷害または損傷および脊髄傷害または損傷である。
「創傷」と「潰瘍」、および「創傷」と「褥瘡」という用語の使用には、しばしば、ある種の重複があり、そして更に、それら用語は、しばしば、無作為に用いられる。したがって、上述のように、本文脈中において、「創傷」という用語は、「潰瘍」、「病変」、「褥瘡」および「梗塞」という用語を包含し、そしてそれら用語は、特に断らない限り、無差別に用いられる。
[000457]一つの態様において、本明細書中に記載の化合物は、創傷治癒の場合に、理学療法/リハビリテーションへの補助として、またはアナボリック薬として有用である。別の態様において、本明細書中に記載の化合物は、前十字靱帯(ACL)または内側十字靱帯(MCL)傷害の治癒を促進する場合に、またはACLまたはMCL手術後の回復を加速する場合に有用である。別の態様において、本明細書中に記載の化合物は、運動選手能力を増強する場合に有用である。別の態様において、本明細書中に記載の化合物は、熱傷を処置する場合に有用である。別の態様において、本明細書中に記載の化合物は、軟骨再成長を刺激する場合に有用である。別の態様において、本明細書中に記載の化合物は、長期重病、肺機能不全、人工呼吸器依存、加齢、AIDS、外傷、外科手術、うっ血性心不全、心筋障害、熱傷、癌、COPDを予防する、処置するまたは逆転させる場合に有用である。別の態様において、本明細書中に記載の化合物は、外傷によるタンパク質異化作用を予防するまたは逆転させる場合に有用である。別の態様において、本明細書中に記載の化合物は、(a)外科手術の場合に創傷治癒を促進するために用いられるような焼灼療法(レーザーまたは放射線)への補助;(b)創傷治癒を促進するための細胞療法への補助;(c)脱毛症、性腺機能低下、筋消耗、オステオペニア、骨粗鬆症、骨量減少、増加したLDL、トリグリセリド(TG)または総コレステロール、HDL低下などの副作用を妨げるための化学療法への補助として有用である。別の態様において、本明細書中に記載の化合物は、慢性異化状態(昏睡、消耗状態、飢餓、摂食障害);随伴性骨折および筋損傷;筋または骨消耗が認められる重病;および/または結合組織疾患および障害において有用である。
[000465]若干の態様において、本発明は、対象の泌尿生殖器疾患および/または受胎能を処置する、その発生率を減少させる、その開始または進行を遅延させる、またはそれに関連した症状を減少させるおよび/または無くする方法を提供する。一つの態様において、その方法は、対象に、本発明の化合物と、抗癌薬、免疫調節薬、抗感染薬、腎臓処置薬、遺伝子治療薬、内分泌系処置薬、ビタミンまたはそれらの組合せを含む組成物を投与することを含む。若干の態様において、泌尿生殖器疾患および/または受胎能疾患は、流産、自発性骨盤癒着、カンジダ症、外陰部膣、分娩後うつ病、糖尿病、妊娠性、性交疼痛症、難産、子癇、子宮内膜症、胎児死亡、胎児成長遅滞、胎児被膜、前期破水、生殖器疾患、女性、生殖器新生物、女性、胞状奇胎、妊娠悪阻、不妊症、卵巣嚢胞、卵巣捻転、骨盤内炎症性疾患、胎盤疾患、胎盤不全、多嚢胞性卵巣症候群、羊水過多、分娩後出血、妊娠合併症、妊娠、異所性、外陰そう痒症、産褥障害、産褥感染、卵管炎、栄養膜新生物、子宮頸部不全、子宮内反、子宮脱、膣疾患、外陰部疾患、外陰苔癬硬化症を含む。
[000487]若干の態様において、本発明は、スタチンで誘発される黄紋筋融解の予防方法を提供する。若干の態様において、本発明は、スタチンで誘発される黄紋筋融解、臓器不全または機能不全の予防方法を提供する。若干の態様において、本発明は、スタチンで誘発される腎または肝の不全または機能不全の予防方法を提供する。一つの態様において、その方法は、対象に、本発明の化合物およびスタチンを含む組成物を投与することを含む。
[000505]一つの態様において、本発明は、対象の脂肪質量を減少させるための、本明細書中に記載の化合物の使用を提供する。別の態様において、本発明は、本明細書中に記載の化合物またはそのプロドラッグ、類似体、異性体、代謝産物、誘導体、薬学的に許容しうる塩、医薬製品、多形、結晶、不純物、N−オキシド、水和物またはいずれかそれらの組合せ、またはそれを含む組成物の使用のためのこのような方法を提供する。
[000508]一つの態様において、本発明は、対象の除脂肪質量を増加させるための、本明細書中に記載の化合物の使用を提供する。別の態様において、このような使用は、本明細書中に記載の化合物またはそのプロドラッグ、類似体、異性体、代謝産物、誘導体、薬学的に許容しうる塩、医薬製品、多形、結晶、不純物、N−オキシド、水和物またはいずれかそれらの組合せの投与を含む。
[000510]実施例5は、式(I)の化合物が、アナボリック性で、なお最小限にアンドロゲン性であるということを示しているので、このような化合物は、過去にアンドロゲンが禁忌であった患者群を処置する場合に有用でありうる。式(I)の化合物は、テストステロンの存在下であれ不存在下であれ、筋成長を刺激し、同時に、前立腺に抗増殖作用を及ぼすことが分かったので、一つの態様において、本発明の方法は、骨量減少または悪液質を有する患者の筋質量減少を回復するために与えられる。
[000515]「肥満関連代謝性障害」という用語は、一つの態様において、肥満症によって生じる、その結果である、それによって悪化する、またはその続発性である障害を意味する。このような障害の非制限例は、変形性関節症、II型糖尿病、血圧の増加、卒中および心臓疾患である。
[000529]「関節炎」という用語は、別の態様において、主に高齢者に起こる、関節軟骨の変性、骨および辺縁の肥大、滑膜の変化等を特徴とする非炎症性変性関節疾患を意味する。それは、他の態様において、特に長時間活動後に、疼痛および硬直を伴う。
[000558]一つの態様において、本発明は、ヒト対象の糖尿病を処置する、抑制する、阻害する、またはその発生率を減少させる方法であって、その対象に、式Iの化合物またはその異性体、薬学的に許容しうる塩、医薬製品、水和物、N−オキシドまたはいずれかそれらの組合せを投与する工程を含む方法を提供する。
[000560]一つの態様において、本発明は、グルコース不耐症を有するヒト対象を処置する方法であって、その対象に、式Iの化合物またはその異性体、薬学的に許容しうる塩、医薬製品、水和物、N−オキシドまたはいずれかそれらの組合せを投与する工程を含む方法を提供する。
式(I)の化合物の(S)鏡像異性体の合成(図1A〜1L)
13C NMR(75MHz,DMSO−d6)δ主要回転異性体について173.3,169.1,140.9,116.4,58.3,48.7,28.9,24.7,19.5:微少回転異性体について174.0,170.0,141.6,115.2,60.3,45.9,31.0,22.3,19.7;
IR(KBr)3437(OH),1737(C=O),1647(CO,COOH),1584,1508,1459,1369,1348,1178cm−1;
[α]D 26+80.8°(c=1,MeOH);
C9H13NO3の分析理論値:C59.00,H7.15,N7.65。実測値:C59.13,H7.19,N7.61。
C9H12BrNO3の分析理論値:C41.24,H4.61,N5.34。実測値:C41.46,H4.64,N5.32。
C4H7BrO3の分析理論値:C26.25,H3.86。実測値:C26.28,H3.75。
Mp:103〜105℃。
シトクロムP450酵素の阻害
[000598]CYP酵素は、細胞の滑面小胞体中に局在するヘムタンパク質のスーパーファミリーである。これら酵素は、広い基質特異性を有し、薬物代謝に関与する主要な酵素群である。
リコンビナント酵素(蛍光基剤)検定
[000600]CYP阻害スクリーニング手順を、本質的には、製造者の取扱い説明書にしたがって行った(Gentest,BDBiosciences,Waltham, MA)。簡単にいうと、CYP酵素阻害を、ヒトcDNAで発現されたCYP3A4、2D6、2C19、2C9および1A2酵素を用いて測定した。モデル基質クマリンの類似体を、各々のイソ酵素に利用した。7−ベンジルオキシトリフルオロメチルクマリン(BFC)を3A4に;3−[2−(N,N−ジエチル−N−メチルアミノ)エチル]−7−メトキシ−4−メチルクマリン(AMMC)を2D6に;3−シアノ−7−エトキシクマリン(CEC)を2C19および1A2に;そして7−メトキシ−4−トリフルオロ−メチルクマリン(MFC)を2C9に。これら基質は、各々の基質の見掛けKmまたはその付近において単一濃度(50μMかまたは75μM)で利用した。阻害検定に用いられた正対照阻害剤を、表1に示す。
[000602]蛍光強度は、Wallac1420Victor3 Multi-label Counter Model(Perkin-Elmer,Wellesley, MA)を用いて、405nmの励起波長フィルターおよび460nm(3A4および2C9基質には535nm)の発光フィルターで測定した。Nunc商標光学ボトム黒色96ウェルプレート(#265301)を、全ての検定に用い、そして1.0秒/ウェルのトップ読み取りを、全ての試料について行った。
[000603]二重反復試験平均値(バックグラウンドを差引く)を、Excelで決定し、そしてIC50値を、GraphPadPrism, v4.03で計算した。IC50決定には、Y=Bottom+(Top−Bottom)/(1+10^((LogEC50−X)*HillSlope))(式中、Xは、指定の化合物の対数濃度であり、Yは、応答である)として定義される非線形回帰方程式「シグモイド用量反応、可変勾配」を用いて、データを当てはめた。
[000604]ケトコナゾール、キニジン、トラニルシプロミン(tranylcypromine)、スルファフェナゾールおよびフラフィリン(furafylline)は、それぞれ、CYP3A4、CYP2D6、CYP2C19、CYP2C9およびCYP1A2活性を強力に阻害して、有意のCYPに媒介される薬物:薬物相互作用について可能性を有する化合物を識別するためのこのinvitroCYPスクリーニング検定の有用性が示された。研究用置換アシルアニリド化合物で、CYP3A4、CYP2D6またはCYP1A2を有意に阻害したものはなく、これらCYPイソ酵素による薬物:薬物相互作用は起こりそうにないということが示された。研究用置換アシルアニリド化合物の全てが、CYP2C9活性を適度に阻害したが、それら化合物で、スルファフェナゾールに類似した力価を示したものはなかった。意外にも、S−(I)だけが、CYP2C19を阻害できなかった。
[000605]S−(II)およびS−(III)は、CYP2C9およびCYP2C19の中程度の阻害を示した。意外にも、S−(I)は、CYP2C19またはCYP2C9をほとんど阻害しなかったので、S−(I)の独特の臨床的且つ治療的利点が示された。
SARMのアンドロゲン受容体結合親和性
材料および方法:
[000606]SARMのアンドロゲン受容体(AR)結合親和性を、invitro競合的放射性リガンド結合検定を用いることによって、高親和性ARリガンドである[17α−メチル−3H]−Mibolerone([3H]MIB,PerkinElmer)で決定した。リコンビナントアンドロゲン受容体リガンド結合ドメイン(ARLBD)を、緩衝液A(10mMTris、pH7.4、1.6mM二ナトリウムEDTA、0.26Mスクロース、10mMモリブデン酸ナトリウム、1mM PMSF)中で[3H]MIBと混合して、[3H]MIBの平衡解離定数(Kd)を決定した。全および非特異的結合を決定するために、タンパク質を、増加濃度の[3H]MIBと一緒に、高濃度の未標識MIBを含んでまたは含むことなくインキュベートした。次に、非特異的結合を、全結合から差し引いて、特異的結合を決定し、そして一部位飽和でのリガンド結合曲線について、SigmaPlotおよび非線形回帰を用いてグラフで示して、MIBのKd(1.84nM)を決定した。更に、ARLBDを飽和するのに必要な[3H]MIBの濃度を、4nMであると決定した。
Ki=KdxIC60/(Kd+L)
(式中、Kdは、[3H]MIBの平衡解離定数(1.84nM)であり、Lは、[3H]MIBの濃度(4nM)である)
で決定した。
[000609]式(I)の化合物[S−(I)]への結合親和性は、放射性リガンド結合検定において、ARLBDを受容体として、Ki(nM)=36.9で調べた。
S−(I)と他の核内ホルモン受容体との交差反応性
[000610]本発明の置換アシルアニリド化合物が、他の核内ホルモン受容体シグナリングに影響したかどうかを確かめるために、ERα−、ERβ−、GR−、PR−またはMRで媒介される転写活性化を刺激する(アゴニスト)または阻害する(アンタゴニスト)その比較能力を、他のアシルアニリドと比較した。
一時的トランスフェクション
[000611]ラットGR、MR、PR、ER−αおよびER−βを、個々に、pCR3.1ベクター主鎖中にクローン化した。配列決定を行って、いずれかの突然変異の不存在を示した。HEK−293細胞を、24ウェルプレートの、5%木炭ストリッピング済みFBSを補足したダルベッコの最少必須培地中に90,000個/ウェルでプレーティングした。それら細胞を、Lipofectamine(Invitrogen,Carlsbad,CA)を用いて、GR、MRおよびPRには0.25μgのGRE−LUC、そしてER−αおよびER−βにはERE−LUC、各々の受容体には0.5ngのCMV−LUC(レニラルシフェラーゼ)および12.5〜25ngのそれぞれの発現ベクターでトランスフェクションした。細胞を、トランスフェクションから24時間後に、対照としての既知のアゴニスト(ERにエストラジオール;GRにデキサメタゾン;MRにアルドステロン;PRにプロゲステロン)の不存在下(アゴニスト様式)および存在下(アンタゴニスト様式)において、研究用置換アシルアニリドSARM化合物(S−I、S−IIおよびS−III)で処理した。ルシフェラーゼ検定は、トランスフェクションから48時間後に行った。転写活性化値は、レニラルシフェラーゼに規格化されたホタルルシフェラーゼとして表す。
S−(III)の結果:
[000614]図3は、ER−β−、ER−α−、GR−、PR−およびMRで媒介されるトランス活性化へのS−(III)のアンタゴニスト作用を要約する。指定の受容体および該当する受容体コンストラクトでトランスフェクションされたHEK−293細胞を、滴定量のS−(III)で処理後、ER−βおよびER−αトランス活性化には1nMエストラジオール、MRトランス活性化には1nMアルドステロン、GRトランス活性化には1nMデキサメタゾン、またはPRトランス活性化には1nMプロゲステロンで処理した。エストラジオールは、ER−β−およびER−αで媒介されるトランス活性化を、それぞれ、3倍および5倍増加させた。細胞と滴定量のS−(III)との共インキュベーションは、エストラジオールで誘発されるER−βまたはER−α活性を変更できなかった。同様に、デキサメタゾンで誘発されるGR媒介トランス活性化およびアルドステロンで誘発されるMR媒介トランス活性化は、いずれの試験濃度でも、S−(III)で阻害されなかった。
[000618]図5は、ER−β−、ER−α−、GR−、PR−およびMRで媒介されるトランス活性化へのS−(II)のアンタゴニスト作用を要約する。指定の受容体でトランスフェクションされたHEK−293細胞を、指定濃度のS−(II)で処理し、そして上のように、適当な受容体について既知のアゴニストで処理した。エストラジオールは、ER−β−およびER−αで媒介されるトランス活性化を、それぞれ、3倍および5倍増加させた。細胞と滴定量のS−(II)との共インキュベーションは、エストラジオールで誘発されるER−βまたはER−α活性を変更できなかった。同様に、デキサメタゾンで誘発されるGR媒介トランス活性化およびアルドステロンで誘発されるMR媒介トランス活性化は、いずれの試験濃度でも、S−(II)で阻害されなかった。S−(III)での場合と同様に、S−(II)は、これら条件下において、試験濃度でER、GRまたはMRに拮抗できなかった。
[000622]HEK−293細胞と、指定濃度のS−(I)との共インキュベーションは、エストラジオールで誘発されるER−βまたはER−α活性、デキサメタゾンで誘発されるGR媒介トランス活性化、またはアルドステロンで誘発されるMR媒介トランス活性化を変更できなかった。
無傷および去勢雄ラットにおけるS−(I)の臨床前アナボリックおよびアンドロゲン薬理。
[000627]約200g体重の雄Sprague-Dawleyラットを、Harlan Bioproducts for Science(Indianapolis,IN)より購入した。それら被験動物を、12時間明/暗サイクルにおいて随意に利用可能な食餌(7012C LM−485Mouse/Rat Sterilizable Diet, HarlanTeklad, Madison,WI)および水で維持した。動物用プロトコールは、InstitutionalAnimalCare によって概説され且つ承認されており、無傷の動物における式(I)の化合物のアナボリック活性およびアンドロゲン活性を調べ、更には、急性精巣摘除(ORX)動物における用量反応評価を行った。慢性的(9日間)ORXラットにおける式(I)の化合物の再生作用を、同様に評価した。
[000630]アンドロゲン組織(前立腺および精嚢)およびアナボリック組織(肛門挙筋)双方における式(I)の化合物の力価および効力を評価するための無傷および去勢ラットでの一連の用量反応研究を行った。無傷動物の場合、式(I)化合物処置は、前立腺および精嚢双方の重量の減少を生じたが、肛門挙筋重量は、有意に増加した。化合物(I)処置後の肛門挙筋重量は、0.01mg/日、0.03mg/日、0.1mg/日、0.3mg/日、0.75mg/日および1mg/日の用量後に、それぞれ、無傷対照の107%±5%、103%±7%、97%±7%、103%±5%、118%±7%および118%±7%であった。前立腺重量は、0.01mg/日、0.03mg/日、0.1mg/日、0.3mg/日、0.75mg/日および1mg/日の用量後に、それぞれ、無傷対照の103%±10%、99%±10%、58%±10%、58%±15%、65%±20%および77%±23%であった。これら結果は、現行アンドロゲン療法が、前立腺および乳房の腫瘍での増殖性アンドロゲン作用のために、若干の患者集団において禁忌であることから、有意である。しかしながら、これら集団中の多くの患者は、筋および骨におけるアンドロゲンのアナボリック作用から利益を得ることがありうると考えられる。式(I)の化合物は、組織選択的アナボリック作用を示したので、過去にアンドロゲンが禁忌であった患者群を処置することは可能でありうる。
化合物Iの代謝安定性:
[000635]代謝安定性検定を、ヒト肝ミクロソームと一緒にインキュベートした場合の式(I)の化合物のinvitro 半減期を評価するために行った。固有クリアランス値を外挿した。ヒト腸管上皮単層(Caco−2細胞)を越える化合物の透過性を、腸管透過性の尺度、更には、流出可能性の指標として評価した。Caco−2細胞は、しばしば、経口バイオアベイラビリティーの初期スクリーニング代用として用いられる。ミクロソーム半減期は、肝固有クリアランスを予測する手段としてのinvitro クリアランス値へと変換することができる。固有クリアランスは、薬物および他の化合物を代謝する肝の機能的能力として定義される。
ヒト肝ミクロソームで測定される代謝安定性:
[000636]本研究の式(I)の化合物を、0.6μMの最終濃度でインキュベートした。ミクロソーム反応は、指定のところで、I期かまたは「I・II期」条件下で行った。化合物原液(10mM ACN)を、最初に、60μM濃度(60%ACN/H2O中)に希釈して、100X溶液の「使用原液」を生じた。ヒト肝ミクロソームは、0.6mg/mlの最終濃度で利用した。二重反復試験ウェルを、各々の時点(0、6分、10分、30分および60分)に用いた。反応は、振とう水浴中において37℃で行い、溶媒の最終濃度を、0.6%で一定に保持した。各々の反応の最終容量は、368μlの100mM KPO4緩衝液(pH7.4);12.6μlのHLM(20mg/ml原液より);6μlの100X「使用原液」薬物化合物、および126μlのNRS「マスターミックス」溶液を含んで成る600μlであった。各々の時点で、100μlの反応を取り出し、そして100μlの氷冷100%ACN(内部標準を加える)が入っている試料ウェルに加えて、反応を止めた。NRS「マスターミックス」は、製造者の取扱説明書(BDBiosciences,Waltham,MA)によって調製されたグルコース6−リン酸デヒドロゲナーゼ、NADP+、MgCl2およびグルコース6−リン酸の溶液である。各6.0mlのNRS「マスターミックス」原溶液は、3.8mlのH2O、1.0mlの溶液「A」(Cat.#461220)および0.2mlの溶液「B」(Cat.#461200)を含有する。ヒト肝ミクロソーム(ロット#0610279,XenotechCorp.)は、60ドナーのプールであった。
[000638]透過性は、分極したCaco−2上皮単層を越える頂端(pH6.6)〜側底(pH7.4)方向および側底(pH7.4)〜頂端(pH6.6)方向で測定した。化合物原液(10mMアセトニトリル)を、研究において、10μMの最終濃度で調べた。レシーバーウェル中の薬物濃度は、LC/MS/MSによって、標準曲線を用いて測定した。各々の化合物の見掛け透過性(Papp)を計算し、そして値(A〜B)を、不十分(Papp:<1)、低(Papp1〜2)、中程度(Papp2〜10)または高(Papp>10)のように分類した。
Papp(cm/秒)=[V/(A*Ci)]*(Cf/T)
V=受容体室の容量(mlまたはcm3)
A=膜インサートの面積(cm2)
Ci=薬物の初期濃度(μM)
Cf=薬物の最終濃度(μM)
T=検定時間(秒)
分析方法:
[000639]全ての試料を、MDS/SciexAPI4000QTrap システムにおいて、化合物に依存して正または負SIM様式のエレクトロスプレーイオン化(ESI)で分析した。移動相は、0.4mL/分の流速を有する30%A(水中の0.1%ギ酸)および70%B(アセトニトリル中の0.1%ギ酸)で無勾配であった。PhenomenexLunaPhenyl-Hexyl カラム(60x2.0mmID,6μ)を用いた。注入容量は、10μLであった。試料毎の総運転時間は、1.6〜3.0分であった。タモキシフェンおよびジクロフェナクを、それぞれ、正および負様式の内部標準として用いた。各々の時点後に残留する親薬物化合物の百分率は、反応開始時(T0分)の初期測定濃度に相対して決定した。
[000640]半減期決定には、GraphPadPrism,v4.03を用いて、Y=スパン*exp(−K*X)+プラトー(一次速度定数Kでのプラトーへの崩壊)として定義される非線形回帰方程式「一相指数崩壊(onephaseexponential decay)」で、データを当てはめた。「−K」は、曲線の勾配である。半減期(分)T1/2=ln0.6/−K、したがって、−0.693/−Kまたは0.693/K、a/k/a−0.693/勾配と定義される。固有クリアランス(μl/分/mgタンパク質)は、CLint=0.693*(1/T1/2)*(mlインキュベーション/mgタンパク質)*1000と定義される。この方程式は、(K*1000)/ミクロソーム濃度として表すこともできる。
イヌにおける化合物(I)の薬物動態
[000322]式(I)の化合物のS異性体の薬物動態を確かめるために、その化合物を、ビーグル犬に経口投与し、そして循環血漿レベル、終末排出半減期(terminaleliminationhaf-life)(t1/2)、全身クリアランス(CL)、終末容量分布(Vz)および絶対バイオアベイラビリティー(F%)(表4)を決定した。化合物(I)は、速やかに且つ完全に代謝された。
Claims (4)
- 前記組成物がさらに前記対象の身体機能を向上させる、請求項1に記載の組成物。
- 前記熟年男性のアンドロゲン欠損(ADAM)に関連した状態が、疲労、うつ病、リビドー低下、性機能不全、勃起障害、性腺機能低下、骨粗鬆症、毛髪減少、貧血、肥満、骨量減少、オステオペニア、良性前立腺増殖症、気分および認知の変調ならびに前立腺癌から選択され、前記女性のアンドロゲン欠損(ADIF)に関連した状態が、性機能不全、性欲低下、性腺機能低下、骨量減少、オステオペニア、骨粗鬆症、認知および気分の変調、うつ病、貧血、毛髪減少、肥満、子宮内膜症、乳癌、子宮癌および卵巣癌から選択される、請求項3に記載の組成物。
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CN116836438A (zh) * | 2023-07-11 | 2023-10-03 | 江西塔益莱高分子材料有限公司 | 一种pcb干膜树脂及其制备方法 |
CN116836438B (zh) * | 2023-07-11 | 2024-02-09 | 江西塔益莱高分子材料有限公司 | 一种pcb干膜树脂及其制备方法 |
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