JP6347745B2 - 結晶性ジアシルヒドラジンおよびその使用 - Google Patents
結晶性ジアシルヒドラジンおよびその使用 Download PDFInfo
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Description
Leu Thr Ala Asn Gln Gln Phe Leu Ile Ala Arg Leu Ile Trp Tyr Gln Asp Gly Tyr Glu Gln Pro Ser Asp Glu Asp Leu Lys Arg Ile Thr Gln Thr Trp Gln Gln Ala Asp Asp Glu Asn Glu Glu Ser Asp Thr Pro Phe Arg Gln Ile Thr Glu Met Thr Ile Leu Thr Val Gln Leu Ile Val Glu Phe Ala Lys Gly Leu Pro Gly Phe Ala Lys Ile Ser Gln Pro Asp Gln Ile Thr Leu Leu Lys Ala Cys Ser Ser Glu Val Met Met Leu Arg Val Ala Arg Arg Tyr Asp Ala Ala Ser Asp Ser Val(107位) Leu Phe Ala Asn Asn Gln Ala Tyr Thr Arg Asp Asn Tyr Arg Lys Ala Gly Met Ala Tyr(127位) Val Ile Glu Asp Leu Leu His Phe Cys Arg Cys Met Tyr Ser Met Ala Leu Asp Asn Ile His Tyr Ala Leu Leu Thr Ala Val Val Ile Phe Ser Asp Arg Pro Gly Leu Glu Gln Pro Gln Leu Val Glu Glu Ile Gln Arg Tyr Tyr Leu Asn Thr Leu Arg Ile Tyr Ile Leu Asn Gln Leu Ser Gly Ser Ala Arg Ser Ser Val Ile Tyr Gly Lys Ile Leu Ser Ile Leu Ser Glu Leu Arg Thr Leu Gly Met Gln Asn Ser Asn Met Cys Ile Ser Leu Lys Leu Lys Asn Arg Lys Leu Pro Pro Phe Leu Glu Glu Ile Trp Asp Val(配列番号1)
であり、これは、米国特許出願公開第2006/100416A1号にも示されている。
粉末X線回折(PXRD)
Bragg−Brentano反射配置のBruker D8 Advance回折計;Cu Kα照射、40kV/40mA;可変の発散スリット;3°のウィンドウのLynxEye検出器;ステップサイズ、0.02°の2θ;ステップ時間、37秒;スキャニング範囲2θで2〜50°。測定中、サンプルを回転させ(0.5rps)、表面を平坦にするためのわずかな圧力以外のいかなる特定な処理もせずに調製した。シリコン製の単結晶サンプルホルダー中、0.1または1mmの深さにおいて周囲実験室条件下で測定を行った。
Brukder RFS 100 FT−Ramanシステム;1064nmで操作するNIR Nd:YAGレーザーおよび液体窒素で冷却したゲルマニウム検出器によってFT−Ramanシステム;FT−Ramanスペクトルを記録した;みかけのレーザーパワー、300mW;分解能2cm−1によって64スキャン;周囲実験室条件下のアルミニウムサンプルホルダー中でサンプルを測定した。
Perkin Elmer DSC7;窒素雰囲気下で充填した、密封した金るつぼ;加熱速度10℃/分。
Projekt Messtechnik SPS 11−100nマルチサンプル水蒸気吸着分析器またはSurface Measurement Systems Ltd. DVS−1水蒸気吸着分析器。サンプルは、所定の湿度プログラムを開始する前に、50%の相対湿度に平衡化させた。
プログラム:50%相対湿度→0%相対湿度→95%相対湿度→50%相対湿度、Δ相対湿度=5%/時間
−潮解に十分な水が吸収されて液体を形成する
−非常に吸湿性の質量増加は15%以上
−吸湿性の質量増加は15%未満で2%以上
−わずかに吸湿性の質量増加は2%未満で0.2%以上
−非吸湿性の質量増加は0.2%未満
Bruker Vector 22 FTIR分光分析器に連結したNetzsch Thermo−Microbalance TG 209;ピンホールを有するアルミニウムるつぼ、N2雰囲気下での測定、加熱速度10℃/分。
US2009/0163592(実施例1を参照のこと)に記載のスキーム1に従って化合物1を調製した。
本開示の目的のために、化合物1の結晶多形混合物は、指定した形態I−A、形態I−B、形態I−C、形態I−D、形態I−E、形態I−F、形態I−Gおよび形態I−Hである。
実施例1に記載の方法を用いて得られた化合物1を、トルエン/ヘプタンから再結晶化し、濾過し、真空下で乾燥した。得られたこの結晶固体をメタノール/水からの第2の再結晶化に供し、濾過し、真空下で乾燥した。得られた結晶固体を微粒子化して、PXRD、FT−Raman分光分析およびDSCによって特性決定した(それぞれ、図1〜3)結晶多形混合物(微量の形態IVを含む形態II)として、形態I−Aの結晶性化合物1を与えた。微粒子化された形態I−Aの化合物1を、本明細書中の以下の方法2〜40において純粋なII、III、IV、V、VI、VII、VIIIおよび形態IXおよびその混合物を調製するための出発材料として使用した。
102mgの形態I−Aの化合物1を2.0mLのn−ヘキサンに懸濁し、超音波処理した。5℃において16時間撹拌後、固体を濾過によって集め、真空下で30分間乾燥して、形態I−E(形態IIIと微量の形態IVの混合物、図7)を得た。
103mgの形態I−Aの化合物1を0.25mLの酢酸イソプロピルに溶解した。窒素流下で1日、溶媒を蒸発させた。真空下で35分間固体を乾燥して、形態I−F(形態IIと微量の形態IVの混合物、図8)を与えた。
100mgの形態I−Aの化合物1を0.15mLのテトラヒドロフランに溶解した。窒素流下で1日、溶媒を蒸発させた。真空下で35分間固体を乾燥して、形態I−Gの混合物(形態IIと微量の形態IVの混合物、図9)を与えた。
108mgの形態I−Aの化合物1を60℃において3.7mLのジイソプロピルエーテルに溶解し、溶液を65℃に加熱した。溶液を3℃/時間で5℃まで冷却して懸濁液を与えた。濾過により固体を集め、真空下で1時間乾燥して、形態I−H(形態IIおよび形態IIIの混合物、図10)を与えた。
純粋な形態IIの結晶性化合物1を以下の方法に従って調製した:
101mgの形態I−Aの化合物1を1.0mLのシクロヘキサンに懸濁し、超音波処理した。60℃において17日間撹拌後、固体を濾過によって集め、真空下で1時間乾燥して形態IIを与えた。
101mgの形態I−Aの化合物1を0.1mLの1:1(v/v)のベンジルアルコール/シクロヘキサンに懸濁し、超音波処理した。60℃において17日間撹拌後、固体を濾過によって集め、真空下で1時間乾燥して形態IIを与えた。
99mgの形態I−Aの化合物1を0.1mLの3:2(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。60℃において17日間撹拌後、固体を濾過によって集め、真空下で1時間乾燥して形態IIを与えた。
100mgの形態I−Aの化合物1を0.2mLの10:1(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。60℃において17日間撹拌後、固体を濾過によって集め、真空下で1時間乾燥して形態IIを与えた。
105mgの形態I−Aの化合物1を0.1mLの1:10(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。60℃において17日間撹拌後、固体を濾過によって集め、真空下で1時間乾燥して形態IIを与えた。
105mgの形態I−Aの化合物1を0.2mLの3:2(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。90℃において5日間撹拌後、0.1mLの追加の溶媒を添加した。90℃においてさらに2日間撹拌後、固体を濾過によって集め、真空下で20分間乾燥して形態IIを与えた。
203mLの形態I−Aの化合物1を0.2mLのメチルエチルケトンに溶解し、2.0mLのn−ドデカンを添加して沈殿を与えた。沈殿を濾過によって集め、真空下で25分間乾燥して形態IIを与えた。
105mgの形態I−Aの化合物1を0.25mLのアセトニトリルに溶解した。窒素流下で1日間、溶媒を蒸発させた。固体を真空下で35分間乾燥して形態IIを与えた。
105mgの形態I−Aの化合物1を0.25mLの酢酸イソプロピルに溶解した。窒素流下で1日間、溶媒を蒸発させた。固体を真空下で35分間乾燥して形態IIを与えた。
112mgの形態I−Aの化合物1を0.15mLのジクロロメタンに溶解した。窒素流下で1日間、溶媒を蒸発させた。固体を真空下で35分間乾燥して形態IIを与えた。
純粋な形態IIIの結晶性化合物1を以下の方法に従って調製した:
109mgの形態I−Aの化合物1を2.0mLのシクロヘキサンに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
113mgの形態I−Aの化合物1を2.0mLのn−ヘプタンに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
106mgの形態I−Aの化合物1を2.0mLのクメメに懸濁し、超音波処理した。室温で1日間撹拌後、追加の28mgの形態I−Aの化合物1を添加した。室温で13日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
109mgの形態I−Aの化合物1を1.0mLのジエチルエーテルに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
165mgの形態I−Aの化合物1を0.2mLの酢酸エチルに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
105mgの形態I−Aの化合物1を1.0mLのtert−ブチルメチルエーテル(TBME)に懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
103mgの形態I−Aの化合物1を0.2mLのトルエンに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
101mgの形態I−Aの化合物1を2.0mLのn−ドデカンに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
133mgの形態I−Aの化合物1を0.2mLの1:1(v/v)のn−ヘキサン/エタノールに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
178mgの形態I−Aの化合物1を0.2mLの1:1(v/v)のn−オクタン/アセトンに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
111mgの形態I−Aの化合物1を0.7mLの3:2(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で2.5時間乾燥して形態IIIを与えた。
97mgの形態I−Aの化合物1を0.8mLの10:1(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で2.5時間乾燥して形態IIIを与えた。
100mgの形態I−Aの化合物1を0.5mLの1:10(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。室温で1日間撹拌後、30mgの形態I−Aの化合物1を添加した。室温で13日間撹拌後、濾過により固体を集め、真空下で2.5時間乾燥して形態IIIを与えた。
105mgの形態I−Aの化合物1を0.7mLの3:2(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。5℃において16日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
102mgの形態I−Aの化合物1を0.7mLの10:1(v/v)のn-ヘプタン/トルエンに懸濁し、超音波処理した。5℃において16日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
115mgの形態I−Aの化合物1を0.7mLの1:10(v/v)のn−ヘプタン/トルエンに懸濁し、超音波処理した。5℃において16日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IIIを与えた。
純粋な形態IVの結晶性化合物1を以下の方法に従って調製した:
106mgの形態I−Aの化合物1を2.0mLの水に懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IVを与えた。TG−FTIRによる調査は、形態IVが、25℃〜150℃で3.5重量%の水を損失した水和物であること(3.9重量%は一水和物に相当する)を示す。TG−FTIRによれば、水和物は100℃近くで水を放出する。
100mgの形態I−Aの化合物1を5.0mLの1;1(v/v)の水:エタノールに懸濁し、超音波処理した。5℃において16日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IVを与えた。
109mgの形態I−Aの化合物1を5.0mLの1:1(v/v)の水:2−プロパノールに懸濁し、超音波処理した。5℃において16日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態IVを与えた。
方法35
126mgの形態I−Aの化合物1を0.55mLのメタノールに溶解した。溶媒を窒素流下で1日蒸発させた。固体を、真空下で35分間乾燥してV形を与えた。TG−FTIRによる調査は、形態Vが、50℃〜150℃で6.7重量%のメタノールを失ったメタノール一溶媒和物であること(6.8重量%は一溶媒和物に相当する)を示す。
方法36
101mgの形態I−Aの化合物1を5.0mLの1:1(v/v)の水:メタノールに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態VIを与えた。乾燥したサンプルのPXRDパターンは、形態IV(水和物)および形態V(メタノール溶媒和物)の重ね合わせとは異なった。形態VIは、おそらく、メタノール溶媒和物/水和物の混合物である。この形態において、メタノール/水の比率は、固体構造に影響することができ、これは、PXRDピーク位置のシフトをもたらす。TG−FTIRによる調査は、形態VIが、25℃〜90℃での3.8重量%のメタノール(およびいくらかの水)および90℃〜130℃での2.1重量%の水(およびいくらかのメタノール)の損失を示す(3.5重量%のメタノールは、ヘミ溶媒和物に相当し;2.0重量%の水は、ヘミ水和物に相当する)。
方法37
101mgの形態I−Aの化合物1を0.5mLのDMSOに懸濁し、超音波処理した。室温で14日間撹拌後、濾過により固体を集め、真空下で30分間乾燥して形態VIIを与えた。TG−FTIRによる調査は、形態VIIが、25℃〜150℃で9.9重量%のDMSOを損失したDMSO溶媒和物であったこと(8.2重量%のDMSOはヘミ溶媒和物に相当し;15.1重量%は、一溶媒和物に相当する)を示し、形態VIIがDMSO溶媒和物であることを示した。PXRDおよびFT−Ramanによる形態VIIの化合物1の特性決定を、図25および26にそれぞれ提供する。表6は、形態VIIの化合物1のPXRDピーク位置、ピーク強度およびd値を列挙する。
方法38
199mgの形態I−Aの化合物1を0.32mLのベンジルアルコールに溶解し、2.0mLのメチルシクロヘキサンを添加した。5℃において4時間撹拌後、濁った溶液を得た。溶媒を5℃において蒸発させた。濾過により固体を集め、真空下で45分間乾燥して形態VIIIを与えた(図27および28)。表7は、形態VIIIの化合物1のPXRDピーク位置、ピーク強度およびd値を列挙する。TG−FTIRによる調査は、25℃〜250℃での63.0重量%のベンジルアルコールの損失を示した。サンプルは不完全に乾燥された可能性があるが、溶媒和物にも相当する可能性がある。サンプルを再び2週間後に調査した。まだ湿った状態にあり、同じ形態に相当することがわかった。次いで、サンプルを窒素流下で1日、その後、真空下で室温において6日間乾燥した。それは、乾燥粉末に見え、FT−Ramanスペクトラムが形態VIIIに相当し、TG−FTIRによる調査が8.9重量%のベンジルアルコールの損失を示した(放出されたすべての溶媒ではない)。
方法39
198mgの形態I−Aの化合物1を0.2mLのアセトンおよび2.0mLのシクロヘキサンに溶解した。溶液を5℃において4時間撹拌し、次いで、5℃において2時間蒸発させて沈殿を得た。沈殿を濾過により集め、真空下で1時間乾燥して形態IXを与えた(図29および30)。表8は、形態IXの化合物1のPXRDピーク位置、ピーク強度およびd値を列挙する。TG−FTIRによる調査は、25℃〜150℃での51.2重量%のシクロヘキサンの損失を示した。サンプルは不完全に乾燥された可能性があるが、シクロヘキサン溶媒和物にも相当する可能性がある。サンプルのPXRDおよびFT−Raman分光分析による再調査は、サンプルが自発的に形態IIに変換したことを示した。
方法40
128mgの形態I−Aの化合物1を0.2mLのギ酸に溶解した。溶媒を窒素流下で1日蒸発させた。固体を、真空下で35分間乾燥し、PXRDによる特性決定(図31)およびFT−Raman分光分析(図32)に基づいて化合物1を非晶形固体(形態X)として与えた。
温度の関数としての形態IIおよび形態IIIの熱力学的安定性を、懸濁液平衡化実験(suspension equilibration experiment)により調査した。
54.6mgの形態IIIの化合物1と61.2mgの形態IIの化合物1を0.8mLの3:2(v/v)のn−ヘプタン:トルエンに懸濁し、超音波処理した。45℃において6時間撹拌後、濾過により固体を集め、真空下で1時間乾燥して、形態IIIと形態IVの混合物を与えた。この実験において、出発材料は、おそらく周囲湿度を吸収して形態IVを与えた。
18.5mgの形態IIIの化合物1と28.0mgの形態IIの化合物1を0.4mLの3:2(v/v)のn−ヘプタン:トルエンに懸濁し、超音波処理した。60℃において6日間撹拌後、濾過により固体を集めて形態IIを与えた。
35.4mgの形態IIIの化合物1と46.1mgの形態IIの化合物1を0.4mLの3:2(v/v)のn−ヘプタン:トルエンに懸濁し、超音波処理した。50℃において6日間撹拌後、濾過により固体を集めて形態IIおよび形態IIIを与えた。
40.5mgの形態IIIの化合物1と45.7mgの形態IIの化合物1を0.4mLの3:2(v/v)のn−ヘプタン:トルエンに懸濁し、超音波処理した。55℃において6日間撹拌後、濾過により固体を集めて形態IIを与えた。
形態IIの化合物1、形態IIIの化合物1または形態IIおよび形態IIIの化合物1の混合物を95:5のヘプタン:エタノール(無水物)中でスラリー化した。1日後、様々な温度においてスラリーの一部を濾過し、XRPDにより分析した。結果を表9に表す。溶液により仲介された遷移は、95:5のヘプタン/エタノール中、45〜47℃において起こる。45℃未満では、形態IIIの化合物1がより安定であり;47℃超では、形態IIの化合物1がより安定である。
形態II、形態III、形態IVおよび形態Vの化合物1の混合物を、少なくとも3日間、異なる温度において様々な組成のメタノール/水または水中にスラリー化した。結果を表10に表す。60%超の体積のメタノール含有量では、3つの実験すべてにおいて、形態Vが最も安定な化合物1の多形である。60%未満の体積のメタノール含有量では、3つの実験すべてにおいて、形態IVが最も安定な化合物1の多形である。
形態IIの化合物1、形態IIIの化合物1および形態IVの化合物1を、閉栓バイアル中で、60〜65℃において様々な長さの時間、貯蔵した。結果を表11に表す。形態IIおよび形態IIIの化合物1は、これらの条件下で未変化のままであった。形態IVの化合物1は、60〜65℃において10日後、形態IIと形態IIIの混合物に変換した。
以下の構築物をマウス胚性線維芽細胞(NIH3T3)中でトランスフェクトすることによって、細胞の遺伝子スイッチアッセイを実施した。a)トウヒシントメハマキEcR(CfEcR−DEF)、およびb)E274V/V390I/Y410E変異(VY−CfEcR−DEF)を含むトウヒシントメハマキEcRからの野生型D−、E−およびF−ドメインを、GAL4−DBDに融合させ、pBlNDベクター(Promega Corporation, Madison,WI,USA)中、CMVプロモーターの制御下においた。VP16−ADに融合した、SV40eプロモーターの制御下にある、ホモサピエンスRXRbおよびトノサマバッタRXRからのキメラRXRは、先に記載されている。(Kothapalli et al., Dev. Genet. 17:319-330 (1995); Palli et al., FEBS J. 272:5979-5990 (2005);および米国特許第7,935,510B2を参照のこと)。誘導性ルシフェラーゼレポータープラスミド、pFRLuc(Stratagene Cloning Systems, La Jolla, CA, USA)は、GAL4応答エレメントの5つのコピーおよび合成ミニマルプロモーターを含む。
ステージIIIおよびIVの黒色腫を有するヒト対象への、hIL−12およびRTS(登録商標)の制御下の1つまたは複数の他の免疫調節剤を発現するように操作された、アデノウイルスにより形質移入された自己の樹状細胞の腫瘍内注射の安全性、忍容性、トランス遺伝子機能および免疫学的効果を、以下に記載のような手順によって評価する。
明細書に組み込まれる。
本願発明は以下の態様を含み得る。[1]
形態IIIは、8.14、8.52、17.00、18.56および22.19°の2
θにピークを有する粉末X線回折パターンを有することを特徴とし;
形態IVは、6.83、10.31、11.30、12.18、12.98、13.6
9、15.11、16.23、17.60、17.99、20.70、21.15、21
.68、22.71、23.79および24.86°の2θにピークを有する粉末X線回
折パターンを有することを特徴とし;
形態Vは、9.38、12.22、13.18、14.98、17.32、18.40
、22.41、23.40、23.55、24.63、24.79、25.61、28.
02および31.77°の2θにピークを有する粉末X線回折パターンを有することを特
徴とし;
形態VIは、9.38、12.23、13.25、17.48、18.41および22
.41°の2θにピークを有する粉末X線回折パターンを有することを特徴とし;
形態VIIは、8.18、9.71、13.30、16.22、17.73、20.9
8、21.20、22.76、24.68、26.72および29.39°の2θにピー
クを有する粉末X線回折パターンを有することを特徴とし;
形態VIIIは、10.05、10.77、14.06、16.76、18.11、1
8.32、18.43、20.89、21.71、21.87、24.07、24.90
および28.71°の2θにピークを有する粉末X線回折パターンを有することを特徴と
し;
形態IXは、7.06、15.74および18.71°の2θにピークを有する粉末X
線回折パターンを有することを特徴とする、
形態III、形態IV、形態V、形態VI、形態VII、形態VIII、もしくは形態I
X、またはその混合物を含む、結晶性(R)−3,5−ジメチル安息香酸N−(1−te
rt−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジ
ドまたは結晶性(S)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル
)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジド。
[2]
形態IIIもしくは形態IV、またはその混合物を含む、請求項1に記載の(R)−3
,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−
3−メトキシ−ベンゾイル)−ヒドラジドまたは(S)−3,5−ジメチル安息香酸N−
(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)
−ヒドラジド。
[3]
実質的に純粋な形態IIIである、請求項1に記載の(R)−3,5−ジメチル安息香
酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾ
イル)−ヒドラジド。
[4]
純粋な形態IIIである、請求項3に記載の(R)−3,5−ジメチル安息香酸N−(
1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−
ヒドラジド。
[5]
前記純粋な形態IIIが、8.14、8.52、9.62、11.02、11.90、
12.16、14.02、14.62、17.00、17.88、18.56、19.0
2、19.24、20.51、20.93、22.19、22.73、23.22、24
.31、24.53、25.91、26.22、27.36、27.73、28.70、
30.84、31.52、32.30、33.19および34.39°の2θにピークを
有する粉末X線回折パターンを有することを特徴とする、請求項4に記載の(R)−3,
5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3
−メトキシ−ベンゾイル)−ヒドラジド。
[6]
実質的に純粋な形態IVである、請求項1に記載の(R)−3,5−ジメチル安息香酸
N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイ
ル)−ヒドラジド。
[7]
純粋な形態IVである、請求項6に記載の(R)−3,5−ジメチル安息香酸N−(1
−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒ
ドラジド。
[8]
前記純粋な形態IVが、6.83、8.38、8.91、10.11、10.31、1
1.30、11.89、12.18、12.98、13.69、14.14、15.11
、15.81、16.23、17.60、17.99、18.60、19.15、19.
66、20.28、20.70、21.15、21.68、22.44、22.71、2
3.50、23.79、24.06、24.86、25.55、26.53、26.94
、27.21、27.60、28.67、29.79、30.50、30.75、31.
55、31.89、32.78、33.25、33.48、33.81および34.68
°の2θにピークを有する粉末X線回折パターンを有することを特徴とする、請求項7に
記載の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’
−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジド。
[9]
非晶形の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−
N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドまたは(S)−3,5−
ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メ
トキシ−ベンゾイル)−ヒドラジド。
[10]
実質的に純粋である、請求項9に記載の(R)−3,5−ジメチル安息香酸N−(1−
tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒド
ラジド。
[11]
前記(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’
−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態が純粋である、請求項
10に記載の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)
−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジド。
[12]
約10μm以下の平均粒径分布を有する、請求項1から11のいずれか一項に記載の(
R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−
エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態(複数可)。
[13]
約1μm以下の平均粒径分布を有する、請求項12に記載の(R)−3,5−ジメチル
安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−
ベンゾイル)−ヒドラジドの形態(複数可)。
[14]
請求項1から13のいずれか一項に記載の(R)−3,5−ジメチル安息香酸N−(1
−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒ
ドラジドの形態(複数可)および1つまたは複数の添加剤を含む組成物。
[15]
前記1つまたは複数の添加剤が、アセトンまたはジメチルスルホキシドを含む、請求項
14に記載の組成物。
[16]
前記1つまたは複数の添加剤が、1つまたは複数の薬学的に許容される添加剤を含む、
請求項14に記載の組成物。
[17]
前記1つまたは複数の薬学的に許容される添加剤が、Miglyol 812、ホスホ
リポン90G、もしくはトコフェリルポリエチレングリコール1000スクシネート、ま
たはその混合物を含む、請求項16に記載の組成物。
[18]
前記1つまたは複数の薬学的に許容される添加剤が、本質的に、Miglyol 81
2、ホスホリポン90G、もしくはトコフェリルポリエチレングリコール1000スクシ
ネートからなる、請求項17に記載の組成物。
[19]
組成物の製造方法であって、請求項1から13のいずれか一項に記載の形態(複数可)
の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(
2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドおよび添加剤を混合するステップ
を含む、方法。
[20]
単離された宿主細胞における目的の遺伝子の遺伝子発現を調節するインビトロの方法で
あって、前記宿主細胞を請求項14に記載の組成物と接触させるステップを含む、方法。
[21]
宿主細胞が、(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル
)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドを結合するリガンド
結合ドメインを含む遺伝子スイッチをコードするポリヌクレオチドを含む、請求項20に
記載の方法。
[22]
前記目的の遺伝子の発現のレベルが、前記(R)−3,5−ジメチル安息香酸N−(1
−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒ
ドラジドの非存在下における前記目的の遺伝子の発現のレベルに比べて増加する、請求項
20に記載の方法。
[23]
対象における疾患、障害、傷害または状態を治療するための、請求項16に記載の組成
物。
[24]
前記対象内の宿主細胞が、(R)−3,5−ジメチル安息香酸N−(1−tert−ブ
チル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドを結合
するリガンド結合ドメインを含む遺伝子スイッチをコードするポリヌクレオチドを含む、
請求項23に記載の組成物。
[25]
前記疾患、障害、傷害または状態が、癌、代謝関連障害、腎臓疾患、貧血、自己免疫障
害、眼の障害、血液障害、神経障害、肺障害、リウマチ性障害、および感染性疾患からな
る群から選ばれる、請求項24に記載の組成物。
[26]
前記遺伝子スイッチが、エクジソン受容体リガンド結合ドメインを含む、請求項21に
記載の方法。
[27]
前記遺伝子スイッチが、エクジソン受容体リガンド結合ドメインを含む、請求項24に
記載の組成物。
[28]
前記遺伝子スイッチがさらに、(R)−3,5−ジメチル安息香酸N−(1−tert
−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドを
結合する前記リガンド結合ドメインと二量体化するリガンド結合ドメインを含む、請求項
27に記載の組成物。
[29]
(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(
2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドを結合する前記リガンド結合ドメ
インと二量体化する前記リガンド結合ドメインが、レチノイドX受容体リガンド結合ドメ
インである、請求項28に記載の組成物。
[30]
前記レチノイドX受容体リガンド結合ドメインが、キメラレチノイドX受容体リガンド
結合ドメインである、請求項29に記載の組成物。
[31]
前記宿主細胞がさらに、その発現が前記遺伝子スイッチによって調節されるペプチド、
タンパク質またはポリペプチドをコードするポリヌクレオチドを含む、請求項24に記載
の組成物。
[32]
前記ポリヌクレオチドが、IL−12またはそのサブユニットをコードする、請求項3
1に記載の組成物。
[33]
昆虫の防除方法であって、前記昆虫またはその生息場所を、殺昆虫有効量の(R)−3
,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−
3−メトキシ−ベンゾイル)−ヒドラジドもしくは(S)−3,5−ジメチル安息香酸N
−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル
)−ヒドラジドの1つもしくは複数の結晶多形もしくは非晶形、またはその組成物と接触
させるステップを含む、方法。
[34]
純粋な形態IIIの結晶性(R)−3,5−ジメチル安息香酸N−(1−tert−ブ
チル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの製造
方法であって、(a)結晶性または非晶形の(R)−3,5−ジメチル安息香酸N−(1
−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒ
ドラジドの懸濁液を、1つまたは複数の非溶媒和物形成溶媒中、約26℃以下において少
なくとも0.5時間、平衡化するステップ;および(b)前記純粋な形態IIIの結晶性
(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2
−エチル−3−メトキシ−ベンゾイル)−ヒドラジドを単離するステップを含む、方法。
[35]
前記溶媒が、ヘプタンおよびトルエンからなる混合物である、請求項34に記載の方法
。
[36]
請求項1から13のいずれか一項に記載の(R)−3,5−ジメチル安息香酸N−(1
−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒ
ドラジドの形態(複数可)を含むキット。
[37]
請求項14に記載の組成物を含むキット。
Claims (9)
- 8.14、8.52、9.62、11.02、11.90、12.16、14.02、14.62、17.00、17.88、18.56、19.02、19.24、20.51、20.93、22.19、22.73、23.22、24.31、24.53、25.91、26.22、27.36、27.73、28.70、30.84、31.52、32.30、33.19および34.39°の2θにピークを有する粉末X線回折パターンを有することを特徴とする(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態IIIの結晶。
- 10μm以下の平均粒径分布を有する、請求項1に記載の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態IIIの結晶。
- 1μm以下の平均粒径分布を有する、請求項2に記載の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態IIIの結晶。
- 請求項1から3のいずれか一項に記載の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態IIIの結晶および1つまたは複数の添加剤を含む組成物。
- 前記1つまたは複数の添加剤が、1つまたは複数の薬学的に許容される添加剤を含む、請求項4に記載の組成物。
- 組成物の製造方法であって、請求項1から3のいずれか一項に記載の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態IIIの結晶および添加剤を混合するステップを含む、方法。
- 単離された宿主細胞における目的の遺伝子の遺伝子発現を調節する方法であって、前記宿主細胞を請求項4に記載の組成物と接触させるステップを含む、方法。
- 請求項1に記載の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態IIIの結晶の製造方法であって、(a)結晶性または非晶形の(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの1つまたは複数の非溶媒和物形成溶媒中の懸濁液を、26℃以下において少なくとも0.5時間、平衡化するステップ;および(b)前記(R)−3,5−ジメチル安息香酸N−(1−tert−ブチル−ブチル)−N’−(2−エチル−3−メトキシ−ベンゾイル)−ヒドラジドの形態IIIの結晶を単離するステップを含む、方法。
- 前記溶媒が、ヘプタンおよびトルエンからなる混合物である、請求項8に記載の方法。
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