JP5078014B2 - ジケトピペラジン合成の触媒反応 - Google Patents

ジケトピペラジン合成の触媒反応 Download PDF

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JP5078014B2
JP5078014B2 JP2007528088A JP2007528088A JP5078014B2 JP 5078014 B2 JP5078014 B2 JP 5078014B2 JP 2007528088 A JP2007528088 A JP 2007528088A JP 2007528088 A JP2007528088 A JP 2007528088A JP 5078014 B2 JP5078014 B2 JP 5078014B2
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スティーブンソン，ジョン・ジェイ
モイエ−シャーマン・デスターディ
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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Description

発明の詳細な説明
関連出願
本特許出願は、2004年8月20日付け出願の米国仮特許出願第60/603,340号に対し、35U.S.C.§119(e)に基づいて優先権を主張する。
発明の分野
本発明は、一般には化学合成に関する。さらに詳細には、本発明は、N-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンの改良された合成に関する。
背景技術
ドラッグデリバリーは医薬技術において永続的な難題となっており、特に、薬物が不安定である場合、および/または、薬物が投与される体内の場所において薬物が吸収されにくい場合にそうである。このような種類の薬物としては、式1の一般構造を有する2,5-ジケトピペラジンがある。
Figure 0005078014
これらの2,5-ジケトピペラジンは、ドラッグデリバリーにおいて有用であることが明らかになっており、特に、酸性のR基を有する2,5-ジケトピペラジンが有用である(たとえば、“Self-assembling diketopiperazine drug delivery system”と題する米国特許第5,352,461号;“Method for making self-assembling diketopiperazine drug delivery system”と題する米国特許第5,503,852号;“Microparticles for lung delivery comprising diketopiperazine”と題する米国特許第6,071,497号;および“Carbon-substituted diketopiperazine delivery system”と題する米国特許第6,331,318号;を参照。これら特許はいずれも、ジケトピペラジンとジケトピペラジンで媒介されるドラッグデリバリーに関して開示しており、全開示内容を参照により本明細書に含める)。ジケトピペラジンは、薬物を組み込む粒子、または薬物を吸着させることのできる粒子に作製することができる。薬物とジケトピペラジンとを組み合わせると、薬物安定性の向上をもたらすことができる。これらの粒子は、種々の投与経路によって投与することができる。これらの粒子は、乾燥粉末として、粒径に応じて呼吸器系の特定の部分に供給することができる。これらの粒子は、静脈注射用懸濁液の剤形中に組み込むのに十分なほどに小さくすることができる。懸濁液を使用する経口デリバリーも可能であり、あるいは錠剤中に圧入したり、またはカプセル中に収容したりすることもできる。これらのジケトピペラジンはさらに、関連した薬物の吸収を容易にすることもできる。
2,5-ジケトピペラジンの合成における従来の手順は、リシンの熱縮合によってN-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンを製造することを含む。従来の工業的製造法では、(N-ベンジルオキシカルボニル)-リシン(Cbz-L-リシン)を使用してビス-3,6-[(N-ベンジルオキシカルボニル)-4-アミノブチル]-2,5-ジケトピペラジン(DKP1)を生成させる。この製造法は、Cbz-L-リシンをm-クレゾール中にて160℃〜170℃で18〜22時間加熱することを必要とし、氷酢酸からの再結晶後に、約47.5%の平均収率にてDKP1が得られる。
したがって本発明の目的は、ジケトピペラジンの改良された合成方法を提供することにある。
発明の要旨
本発明は、従来の手順/方法と比較して、より速やかな反応時間とより高い収率が達成されるよう、触媒を使用してジケトピペラジンを合成する方法を提供する。縮合環化反応において、本発明の触媒(五酸化リン)を使用すると、従来の手順/方法より短い反応時間にて、より高い収率とより高い純度のジケトピペラジンの合成が可能となる。
本発明は、硫酸(H2SO4)、リン酸(H3PO4)、および五酸化リン(P2O5)からなる群から選択される触媒の存在下にてε-アミノ保護リシンの溶液を加熱する工程を含む、N-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンの合成方法を提供する。
本発明の1つの実施態様は、ε-アミノ保護リシンが(N-ベンジルオキシカルボニル)-リシン(Cbz-L-リシン)であって、生成物がビス-3,6-[(N-ベンジルオキシカルボニル)-4-アミノブチル]-2,5-ジケトピペラジン(DKP1)である場合の、N-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンの合成方法を提供する。
本発明の他の実施態様は、溶液を約160℃〜約170℃のターゲット温度に加熱という場合の、N-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンの合成方法を提供する。このターゲット温度は約4〜6時間で達成されるのが好ましい。
本発明のさらに他の実施態様においては、ターゲット温度に達する約10時間以内に合成が実質的に完了するという場合の、触媒の存在下にてε-アミノ保護リシンの溶液を加熱する工程を含むN-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンの合成方法が提供される。ターゲット温度に達する約8時間以内、約6時間以内、約4時間以内、約3時間以内、または約2時間以内に合成が実質的に完了するのがさらに好ましい。ターゲット温度に達する約1.5時間以内に合成が実質的に完了するのが最も好ましい。
本発明の他の実施態様は、合成の収率が50%より高い場合の、触媒(たとえば五酸化リン)の存在下にてε-アミノ保護リシン〔たとえば(N-ベンジルオキシカルボニル)-リシン(Cbz-L-リシン)〕の溶液を加熱する工程を含むN-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンの合成方法を提供する。
本発明の他の実施態様は、五酸化リン触媒の濃度が約5%〜約10%であるという場合の、五酸化リン触媒の存在下にてN-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンを合成する方法を提供する。
本発明の上記の目的、利点、および特徴、ならびに本発明の他の目的、利点、および特徴は、下記の説明を考察することによってより理解が深まるであろう。
発明の詳細な説明
本発明は、従来の手順/方法と比較して、より速やかな反応時間とより高い収率が達成されるよう、触媒を使用してジケトピペラジンを合成するための方法を提供する。縮合環化反応において、本発明の触媒(五酸化リン)を使用すると、従来の手順/方法より短い反応時間にて、より高い収率とより高い純度のジケトピペラジンの合成が可能となる。
ドラッグデリバリーにおいて有用なジケトピペラジン〔たとえば、2,5-ジケト-3,6-ジ(4-フマリルアミノブチル)ピペラジン(フマリルジケトピペラジン、FDKP)〕の従来の合成は通常、ε-アミノ保護リシン〔たとえば、(N-ベンジルオキシカルボニル)-リシン(Cbz-L-リシン)〕の熱縮合環化から始まる(図1と図2を参照)。無触媒の反応は長い時間がかかり(18〜33時間)、収率は50%未満であり、場合によっては25%にしかならない。このように反応時間が長く、収率が比較的低いと、工業的応用において反応器の処理量が少なくなるので望ましくない。
周知のように、ジケトピペラジンを製造するのに、五酸化リン(P2O5)が触媒として、そしてポリリン酸が溶媒として使用されている。たとえば、Galinskyらによる「J.Am.Pharm.Assoc,1957,46:391-3」(グリシン、アラニン、ロイシン、イソロイシン、およびフェニルアラニンジケトピペラジンを製造する上で、ポリリン酸をP2O5と共に使用することが説明されている);およびKappeらによる「ARKIVOC2001(ii),p.122-134」〔P2O5(ポリリン酸エステルとして)を縮合環化/脱水の試剤として使用するBiginelliジヒドロピリミドンの合成が説明されている〕を参照のこと。さらに、Erlangerによる「J.Org.Chem.,1961,26:2534-6“Phosphorus pentoxide as a reagent in peptide synthesis”」を参照のこと。この文献には、保護アミノ酸フラグメントから線状ジペプチドを製造するための試剤としてP2O5が(ブタノール亜リン酸水素ジエチル（butanol diethyl hydrogen phosphite）と共に)使用されていることが説明されている。しかしながら驚くべきことに、上記文献に記載の反応条件と溶媒では、出発物質である(N-ベンジルオキシカルボニル)-リシンの分解が起こり、したがって本発明の開示内容とは相容れない、ということが本発明者らによって発見された。したがって、反応を早めることができて、且つより高い収率をもたらすことができる触媒が求められた。
本発明の1つの実施態様は、反応の速度を増大させ、より高い収率もたらすための触媒を上記反応中に組み込むことを含む。硫酸(H2SO4)、リン酸(H3PO4)、および五酸化リン(P2O5)の3種の試剤を、m-クレゾールを溶媒として使用するこの脱水縮合環化反応のための触媒としての有用性に関して評価した。本発明の合成に関して本明細書で使用している“実質的に完了する(substantially complete)”とは、出発物質の少なくとも約80%が所定の時間内に消費される、ということを表わしている。有望な触媒のそれぞれを使用して反応を行った。Cbz-L-リシンの消費と、ビス-3,6-[(N-ベンジルオキシカルボニル)-4-アミノブチル]-2,5-ジケトピペラジン(DKP1)の出現を、本反応の全体を通した幾つかの時点において、高速液体クロマトグラフィー(HPLC)によってモニターした。選定した時点においてDKP1を単離し、その収率を算出した。
硫酸を触媒として使用すると、約35%の収率が得られた(この値は無触媒反応の範囲内である)。しかしながらこの35%の収率は、同等の反応収率(%)を達成するのに約18時間〜約33時間かかるという従来の無触媒での反応時間と比較して、わずか4時間で達成された(図3を参照)。
リン酸触媒反応は、Cbz-L-リシンの少なくとも約80%が消費されたという点において、約3時間で実質的に完了した。DKP1は、反応の4時間以内に評価したときには安定であり、収率は約55%であることがわかった(図4)。
五酸化リン触媒反応では、Cbz-L-リシンの約90%が1時間で消費され、Cbz-L-リシンのほぼ全てが約1.5時間で消費された。この時点において、収率は約60%であることがわかった(図5を参照)。したがって、これら3種の触媒はいずれも、反応速度を大幅に増大させ、さらに、リン酸と五酸化リンは収率(%)も増大させた(図6と表1を参照)。
Figure 0005078014
本発明の反応において使用するのに適した溶媒としては、m-クレゾール、エチレングリコール、プロピレングリコール、トルエン、キシレン、および当業者に公知の同等物などがあるが、これらに限定されない。さらに、当業者には周知のことであるが、各種の溶媒は異なった沸点と極性を有し、したがって反応温度と反応時間は溶媒に応じて変わってよい。
実施例
実施例1
五酸化リン触媒による3,6-ビス[4-(N-ベンジルオキシカルボニル)アミノプロピル]-2,5-ジケトピペラジン(DKP1)の合成I
Figure 0005078014
メカニカルスターラー、熱電対温度読み出し/コントローラ、窒素ガス入口、およびショートパス蒸留装置を装備した1リットルの4つ口丸底フラスコに、100gのCbz-オルニチン、7.5gの五酸化リン、および300mLのm-クレゾールを装入した。攪拌と窒素パージを開始した。生成したスラリーを165℃±5℃に加熱した。完全な溶液が形成された後(約30〜60分)、混合物を165℃でさらに60分保持した。加熱用マントルを取り除き、溶液を50℃に冷却した。メタノールと水との80:20混合物(1000mL)からなるクエンチ溶液を2000mLビーカー中に調製した。暖かな反応溶液を攪拌状態のメタノール(MeOH)溶液中に注ぎ込み、生成した懸濁液を30分攪拌した。懸濁液を、中度多孔性の焼結ガラス漏斗を通して濾過し、濾過ケーキを、250mLのMeOH、250mLの脱イオン水、および2×250mLのMeOHで逐次洗浄した。単離した生成物を真空オーブン中にて一晩乾燥した(50℃、30インチ水銀)。粗生成物を酢酸から再結晶し、真空オーブン中にて乾燥して58.5g(63%)の所望のジケトピペラジンを得た。
元素分析：計算値 C 62.89 H 6.50 N 11.28
実測値 C 62.15 H 6.64 N 11.09
1H NMR分析：(d6-DMSO):
δ8.97, 2H (NH); δ 7.28-7.37, 10H (CH); δ7.08, 2H (NH); δ5.01, 4H (CH 2); δ3.79, 2H (CH); δ2.99-3.01, 4H (CH 2); δ1.60-1.70, 4H (CH 2); δ1.46-1.57, 4H (CH 2)
実施例2
五酸化リン触媒によるDKP1の合成II
メカニカルスターラー、ショートパス蒸留装置、熱電対温度読み出し/コントローラ、および窒素ガス入口を装備した1リットルの丸底フラスコに、Cbz-L-リシン(100g)、m-クレゾール(200g)、および五酸化リン(7.5g)を装入した。反応混合物を攪拌し、165℃のターゲット温度に加熱し、165℃にて1.5時間保持した。図7を参照。
加熱時間の終了後、反応溶液を室温(22〜25℃)に冷却し、脱イオン水(100mL)とMeOH(400mL)との溶液でクエンチした。得られた懸濁液を30〜60分攪拌し、中度多孔性の焼結ガラス漏斗を通して濾過した。濾過ケーキを、250mLのMeOH、2×250mLの脱イオン水、および2×250mLのMeOHで逐次洗浄した。
湿潤ケーキを真空オーブン中にて50℃で乾燥した。回収した物質をHPLCによって分析し、下記の手順にしたがって氷酢酸(粗生成物1g当たり3mL)から再結晶した。粗製の乾燥DKP1を酢酸中に混合し、温度計と還流冷却器(窒素ヘッドと窒素出口がアルカリスクラバーに連結されている)とを取り付けた三角フラスコ中にて加熱還流した。5〜10分後(完全に溶解したことを確認した後)、加熱を止め、混合物を100℃未満の温度に冷却した。フラスコに脱イオン水(粗生成物1g当たり1mL)を加え、生成した懸濁液を、攪拌しながら6〜18時間にわたって室温に冷却した。沈殿した固体を、中度多孔性の焼結ガラス漏斗を通して濾過し、脱イオン水(3×100mL)とアセトン(3×100mL)で洗浄した。再結晶した湿潤ケーキを真空オーブン中にて50℃で乾燥した。
実施例3
五酸化リン触媒によるDKP1の合成の最適化
DKP1を形成させるためのCbz-L-リシンの脱水カップリングと環化を、反応加熱時間とP2O5装入量の関数として評価した。5%、7.5%、または10%のP2O5(Cbz-L-リシンを基準とした重量%)を使用して、種々の加熱時間にて反応を行った(表2)。これらのデータから、7.5%のP2O5を使用したときに収率と純度が最大になることがわかった。
7.5%五酸化リン触媒によるCbz-L-リシンのDKP1への転化に対する最適条件を確認するために、引き続き実験を計画した。さらに、これらの反応を、Cbz-L-リシンの消失に関してモニターした。図5は、Cbz-L-リシン/クレゾール/P2O5(7.5%)の反応混合物を、3時間にわたってDKP1の形成に関してモニターした、という実験から得られたデータを示している。この時間中、反応温度を165℃±5℃に保持した。反応全体の特定の時点にてアリコート(3mL)を取り出し、脱イオン水/メタノールでクエンチし、濾過によって生成物を単離した。これらサンプルのHPLC分析から、DKP1の収率は、1〜3時間加熱した後に最大に達するということがわかった(表2)。165℃±5℃にて4時間後、DKP1の収率が7〜8%低下することが観察された。
1〜3時間が最適反応時間であることが確認されたので、この時間内にて単離DKP1の収率を測定するために、幾つかの反応(100gスケール)を行った。図8は、単離DKP1の最大収率(60.9%)が1.5時間後に得られたということを示している。HPLC分析から、この物質が99.5%を超える純度のDKP1であることがわかった。この反応を繰り返したところ、同等の結果が得られた。すなわち、DKP1(100.0面積%)が63.0%の収率で単離された。さらに、長い加熱時間をシミュレートするために、4時間と6時間の加熱傾斜（ヒートランプ：heat ramp）を使用してこの反応を行った。これらの反応の収率は、それぞれ59.9%と63.1%であった(表2)。
Figure 0005078014
最適化された条件(7.5%のP2O5、165℃、1.5時間)を、5リットルのスケールにて2回実証した。再び、4時間と6時間のランプを使用して、製造量(production volume)において使用される加熱プロフィールをシミュレートした。どちらの反応も、1リットルスケールにおいて得られた結果を再現した。これらの反応は58.9%と58.4%の全収率をもたらし、生成物の純度は、現行のプロセスと同等(99.8%)であった。
特に明記しない限り、明細書と特許請求の範囲において使用されている、成分の量、分子量のような特性、および反応条件など、を表示している全ての数は、“およそ(about)”という言葉で規定されているものと考えるべきである。したがって、それと反対の表示がなされない限り、下記の明細書と特許請求の範囲に記載の数値パラメーターは近似値であり、これらの値は、本発明によって得ようとする所望の特性に応じて変わることがある。控えめに言っても、特許請求の範囲への均等論の適用を限定しようとするものではなく、それぞれの数値パラメーターは、少なくとも、記載されている有効数字の数を考慮して、また通常の四捨五入法を適用することによって解釈すべきである。本発明の広い範囲を示している数値範囲と数値パラメーターが近似値であるという点にもかかわらず、特定の実施例において示されている数値は可能な限り正確に記載されている。しかしながら、いかなる数値も、個々の試験測定値において見られる標準偏差から必然的に生じる特定の誤差を本質的に含む。
本発明を説明する文脈において(特に、特許請求の範囲の文脈において)使用されている“a”、“an”、“the”、および類似の表示は、特に明記しない限り、あるいは文脈によって明確に否定しない限り、単数と複数の両方を含んでいるものと解釈すべきである。本明細書における値の範囲の列挙は、単に、範囲内に含まれている個々の値に個別に言及する簡便な方法として役立つよう意図されている。特に明記しない限り、それぞれの個別の値は、明細書に個別に挙げられたかのごとく明細書中に組み込まれる。本明細書に記載の方法はいずれも、特に明記しない限り、あるいは文脈によって明確に否定しない限り、任意の適切な順序で行うことができる。本明細書に記載の全ての実施例または例示的な言い回し〔たとえば“等の(such as)”〕は、単に、本発明をよりわかりやすく実証すべく意図されており、特許請求している本発明の範囲に対して限定をもたらすものではない。明細書中の言い回しは、本発明の実施に対して必須の、特許請求されていないエレメントを全て示していると解釈すべきではない。
本明細書に開示の本発明の別のエレメントや実施態様のグループ分け(grouping)は、限定として解釈すべきではない。各グループメンバーは、個別に言及して特許請求することもできるし、あるいはグループの他のメンバーまたは本明細書中に見られる他のエレメントと任意に組み合わせて言及して特許請求することもできる。便宜上の点から、および/または特許性の点から、あるグループの1つ以上のメンバーを、あるグループに組み入れることもできるし、あるいはあるグループから削除することもできる、と考えられる。このような組み入れや削除が行われる場合は、明細書は、グループを修正されたものとして含み、したがって、特許請求の範囲において使用されている全てのマルクーシュ・グループの記載要件が満たされる。
本発明を実施するために本発明者らが認識しているベストモードを含め、本発明の好ましい実施態様が説明されている。言うまでもないが、好ましい実施態様に対する種々のバリエーションは、上記の説明を読めば当業者にとっては明らかとなろう。本発明者らは、当業者がこのようなバリエーションを必要に応じて使用するものと考えており、また本発明が、本明細書に具体的に説明されているのとは別のやり方で実施されることを意図している。したがって本発明は、特許請求の範囲に挙げられている主題に対する全ての改良形と等価形を、適用法にしたがって認められるものとして含む。さらに、特に明記しない限り、あるいは文脈によって明確に否定しない限り、全ての可能なバリエーションにおける上記エレメントの任意の組み合わせも本発明に包含される。
さらに、特許や印刷された刊行物に対しても言及がなされている。上記の引用文献や印刷刊行物のそれぞれの全記載内容を参照により本明細書に含める。
最後に、本明細書に開示の本発明の実施態様は、本発明の原理を例示しているにすぎないことは言うまでもない。使用できる他の改良形も本発明の範囲内に含まれる。したがってたとえば、本発明の他の形態(限定ではない)も、本明細書中の開示内容にしたがって使用することができる。したがって本発明は、正確に図示および説明されている実施態様に限定されない。
図1は、本発明の1つの態様にしたがった、2,5-ジケト-3,6-ジ(4-フマリルアミノブチル)ピペラジン(フマリルジケトピペラジン、FDKP)合成のフローチャートである。 図2は、本発明の1つの態様にしたがった、ビス-3,6-[(N-ベンジルオキシカルボニル)-4-アミノブチル]-2,5-ジケトピペラジン(DKP1)合成のフローチャートである。 図3は、本発明の1つの態様にしたがった、硫酸触媒法を使用した場合の、(N-ベンジルオキシカルボニル)-リシン(Cbz-L-リシン)のDKP1への転化を示している。 図4は、本発明の1つの態様にしたがった、リン酸触媒法を使用した場合の、Cbz-L-リシンのDKP1への転化を示している。 図5は、本発明の1つの態様にしたがった、五酸化リン触媒法を使用した場合の、Cbz-L-リシンのDKP1への転化を示している。 図6は、本発明の1つの態様による、3種の触媒の比較を示している。 図7は、本発明の1つの態様にしたがった、P2O5-触媒作用による環化二量化の反応シーケンスを示している。 図8は、本発明の五酸化リン触媒を使用した場合の、DKP1の全収率対時間の関係を示している（５リットルスケールの反応）。

Claims (10)

  1. 硫酸、リン酸、および五酸化リンからなる群から選択される触媒の存在下、ｍ−クレゾール、エチレングリコール、トルエン及びキシレンからなる群から選択される溶媒中で、ε-アミノ保護リシンの溶液を加熱する工程を含む、N-保護したビス-3,6-[4-アミノブチル]-2,5-ジケトピペラジンの合成方法。
  2. 前記ε-アミノ保護リシンが(N-ベンジルオキシカルボニル)-リシン(Cbz-L-リシン)である、請求項１に記載の合成方法。
  3. 前記触媒が硫酸である、請求項１に記載の合成方法。
  4. 前記触媒がリン酸である、請求項１に記載の合成方法。
  5. 前記触媒が五酸化リンである、請求項１に記載の合成方法。
  6. 五酸化リンの濃度が5%〜10%である、請求項５に記載の合成方法。
  7. 五酸化リンの濃度が7.5%である、請求項６に記載の合成方法。
  8. 前記溶液を160℃〜170℃のターゲット温度に加熱する、請求項１に記載の合成方法。
  9. ターゲット温度が4時間〜6時間で達成される、請求項８に記載の合成方法。
  10. 五酸化リン触媒の存在下、ｍ−クレゾール溶媒中で、Ｎ−ベンジルオキシカルボニル−オルニチンの溶液を加熱する工程を含む、３，６−ビス［４−（Ｎ−ベンジルオキシカルボニル）アミノプロピル］−２，５−ジケトピペラジンの合成方法。
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