JP2017523133A - ニコチン塩、共結晶、及び塩共結晶複合体 - Google Patents
ニコチン塩、共結晶、及び塩共結晶複合体 Download PDFInfo
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Abstract
Description
置換及び非置換芳香族ジカルボン酸(例えば、1,2−ベンゼンジカルボン酸(フタル酸)、1,3−ベンゼンジカルボン酸(イソフタル酸)、1,4−ベンゼンジカルボン酸(テレフタル酸)、2−ヨード−1,3−ベンゼンジカルボン酸、2−ヒドロキシ−1,4−ベンゼンジカルボン酸、2−ニトロ−1,4−ベンゼンジカルボン酸、3−フルオロ−1,2−ベンゼンジカルボン酸、3−アミノ−1,2−ベンゼンジカルボン酸、3−ニトロ−1,2−ベンゼンジカルボン酸、4−ブロモ−1,3−ベンゼンジカルボン酸、4−ヒドロキシ−1,3−ベンゼンジカルボン酸、4−アミノ−1,2−ベンゼンジカルボン酸、4−ニトロ−1,2−ベンゼンジカルボン酸、4−スルホ−1,2−ベンゼンジカルボン酸、4−アミノ−1,3−ベンゼンジカルボン酸、5−ブロモ−1,3−ベンゼンジカルボン酸、5−ヒドロキシ−1,3−ベンゼンジカルボン酸、5−アミノ−1,3−ベンゼンジカルボン酸、5−ニトロ−1,3−ベンゼンジカルボン酸、5−エチニル−1,3−ベンゼンジカルボン酸、5−シアノ−1,3−ベンゼンジカルボン酸、5−ニトロ−1,3−ベンゼンジカルボン酸、2,5−ヒドロキシ−1,4−ベンゼンジカルボン酸、及び2,3,5,6−テトラフルオロ−1,4−ベンゼンジカルボン酸;
置換及び非置換ヒドロキシ安息香酸(例えば、2−ヒドロキシ安息香酸(サリチル酸)、3−ヒドロキシ安息香酸、4−ヒドロキシ安息香酸、2−メチル−4−ヒドロキシ安息香酸、3−tert−ブチル−4−ヒドロキシ安息香酸、4−エトキシ−2−ヒドロキシ安息香酸、3−クロロ−5−ヒドロキシ安息香酸、5−クロロ−2−ヒドロキシ安息香酸、3−ブロモ−4−ヒドロキシ安息香酸、3−ブロモ−5−ヒドロキシ安息香酸、4−ブロモ−2−ヒドロキシ安息香酸、5−ブロモ−2−ヒドロキシ安息香酸、2−フルオロ−5−ヒドロキシ安息香酸、3−フルオロ−4−ヒドロキシ安息香酸、3−フルオロ−2−ヒドロキシ安息香酸、3−フルオロ−5−ヒドロキシ安息香酸、2−フルオロ−6−ヒドロキシ安息香酸、4−フルオロ−3−ヒドロキシ安息香酸、2−フルオロ−4−ヒドロキシ安息香酸、5−フルオロ−2−ヒドロキシ安息香酸、2−アミノ−3−ヒドロキシ安息香酸、2−アミノ−5−ヒドロキシ安息香酸、3−アミノ−2−ヒドロキシ安息香酸、3−アミノ−4−ヒドロキシ安息香酸、3−アミノ−5−ヒドロキシ安息香酸、4−アミノ−2−ヒドロキシ安息香酸、4−アミノ−3−ヒドロキシ安息香酸、5−アミノ−2−ヒドロキシ安息香酸(メサラミン)、5−アミノエチル−2−ヒドロキシ安息香酸、4−ホルミル−3−ヒドロキシ安息香酸、3−ホルミル−4−ヒドロキシ安息香酸、5−(アセチルアミノ)−2−ヒドロキシ安息香酸)、4−ニトロ−2−ヒドロキシ安息香酸、3,5−ジエチル−4−ヒドロキシ安息香酸、3,5−ジ−tert−ブチル−4−ヒドロキシ安息香酸、3,5−ジイソプロピル−2−ヒドロキシ安息香酸、3,4−ジメトキシ−4−ヒドロキシ安息香酸(シリンガ酸)、3,5−ジクロロ−2−ヒドロキシ安息香酸、3,5−ジクロロ−4−ヒドロキシ安息香酸、3,6−ジクロロ−2−ヒドロキシ安息香酸、2,3−ジフルオロ−4−ヒドロキシ安息香酸、3,4−ジフルオロ−2−ヒドロキシ安息香酸、3,5−ジブロモ−2−ヒドロキシ安息香酸、3,5−ジヨード−2−ヒドロキシ安息香酸、4−アミノ−5−クロロ−2−ヒドロキシ安息香酸、3,5−ジニトロ−2−ヒドロキシ安息香酸、2,4,6−トリブロモ−2−ヒドロキシ安息香酸、2,3,5,6−テトラフルオロ−4−ヒドロキシ安息香酸、及び2,3,4,5−テトラフルオロ−6−ヒドロキシ安息香酸);
置換及び非置換ジヒドロキシ安息香酸(例えば、2,3−ジヒドロキシ安息香酸(ピロカテキン酸/乳汁酸)、2,4−ジヒドロキシ安息香酸(β−レソルシル酸)、2,5−ジヒドロキシ安息香酸(ゲンチジン酸/ヒドロキノンカルボン酸)、2,6−ジヒドロキシ安息香酸(γ−レソルシル酸)、3,4−ジヒドロキシ安息香酸(プロトカテキン酸)、3,5−ジヒドロキシ安息香酸(α−レソルシル酸)、4−ヒドロキシ−3−メトキシ安息香酸(バニリン酸)、6−メチル−2,4−ジヒドロキシ安息香酸(オルセレン酸)、4−ブロモ−3,5−ジヒドロキシ安息香酸、5−ブロモ−2,4−ジヒドロキシ安息香酸、5−ブロモ−3,4−ジヒドロキシ安息香酸、6−カルボキシメチル−2,3−ジヒドロキシ安息香酸、3,5−ジブロモ−2,4−ジヒドロキシ安息香酸、3,5−ジクロロ−2,6−ジヒドロキシ安息香酸、及び5−アミノ−3−クロロ−2,4−ジヒドロキシ安息香酸);ならびに
置換及び非置換トリヒドロキシ安息香酸(例えば、2,3,4−トリヒドロキシ安息香酸、2,4,5−トリヒドロキシ安息香酸、2,4,6−トリヒドロキシ安息香酸(フロログルシノールカルボン酸)、及び3,4,5−トリヒドロキシ安息香酸(没食子酸))。
置換及び非置換芳香族トリカルボン酸(例えば、1,2,3−ベンゼントリカルボン酸、1,2,4−ベンゼントリカルボン酸(トリメリト酸);ならびに
置換及び非置換芳香族テトラカルボン酸(例えば、1,2,3,4−ベンゼンテトラカルボン酸(メロファン酸)及び1,2,4,5−ベンゼンテトラカルボン酸(ピロメリト酸)であり得る。
一般的
X線粉末回折(XRPD)
X線粉末回折パターンを、Bruker AXS C2 GADDS回折計上でCu Kα照射(40kV、40mA)、自動XYZステージ、自動試料位置付けのためのレーザービデオ顕微鏡、及びHiStar2次元面検出器を使用して収集する。X線光学は、0.3mmのピンホールコリメータと連結された単一Gobel多層ミラーからなる。認証された標準NIST 1976コランダム(平板)を使用して週1回の性能チェックを行う。ビーム広がり、すなわち、試料上のX線ビームの有効サイズは約4mmである。θ−θ連続走査モードは、20cmの試料−検出器距離で用いられ、3.2°〜29.7°の有効2θ範囲を付与する。典型的に、試料は、X線ビームに120秒間曝露される。データ収集に使用されるソフトウェアは、XP/2000 4.1.43の場合、GADDSであり、Diffrac Plus EVA v13.0.0.2またはv15.0.0.0を使用してデータを分析して提示する。
Oxford Diffraction Supernova Dual Source、Cu at Zero、Atlas Oxford Cryosystems Cobra冷却デバイスを備えるCCD回折計上でデータを収集する。CuKα照射を使用してデータを収集する。構造は、典型的にSHELXSまたはSHELXDプログラムのいずれかを使用して解明され、Bruker AXS SHELXTLスイート(V6.10)の一部としてSHELXLプログラムを用いて精緻化する。別途記載されない限り、炭素原子に結合した水素原子は、幾何学的に置かれ、騎乗等方性変位パラメータを用いて精緻化することを可能にする。ヘテロ原子に結合した水素原子は、差フーリエ合成に位置し、等方性変位パラメータを用いて自由に精緻化されることを可能にする。
スクリーニング実験を最初に行い、ムチン酸の塩の形成のための無溶媒方法を評価する。必要とされる量のムチン酸(100μLのニコチンに対して)を、HPLCバイアル瓶に計量する。(S)−ニコチンを各バイアル瓶に分注し、バイアル瓶を室温で3日間振動させる。固体を試料採取し、XRPDによって特徴付ける。表1に示すように、XRPD分析結果は、バイアル瓶内で形成された固体が、ムチン酸の塩の形成を指示する、新たな結晶相形態を含むことを示す。
スクリーニング実験を最初に行い、4−アセトアミド安息香酸の塩の形成のための無溶媒方法を評価する。4−アセトアミド安息香酸(111mg)を、移動スラリー(400μL)を生成するために必要な最小量の(S)−ニコチンに懸濁する。スラリーを、室温で48時間振動させる。結果として得られる白色の粉末固体を、濾過によって単離し、試料採取してXRPDによって特徴付けを行ったところ、新たな結晶形態を示す。
スクリーニング実験を最初に行い、ゲンチジン酸の塩の形成のための無溶媒方法を評価する。ゲンチジン酸(95mg)を、移動スラリー(200μL)を生成するために必要な最小量の(S)−ニコチンに懸濁する。スラリーを、室温で48時間振動させる。結果として得られるピンク色の固体を、濾過によって単離し、試料採取してXRPDによって特徴付けを行ったところ、新たな結晶形態を示す。
スクリーニング実験を最初に行い、3−ヒドロキシ安息香酸の塩の形成のための無溶媒方法を評価する。3−ヒドロキシ安息香酸(85mg)を、移動スラリー(200μL)を生成するために必要な最小量の(S)−ニコチンに懸濁する。スラリーを、室温で48時間振動させる。結果として得られるガムを試料採取し、XRPDによって特徴付ける(試料が溶解したことを示す)。
スクリーニング実験を最初に行い、L−リンゴ酸の塩の形成のための無溶媒方法を評価する。必要とされる量のL−リンゴ酸(100μLのニコチンに対して)を、HPLCバイアル瓶に2:1、1:1、及び1:2の比のニコチン:酸で計量する。(S)−ニコチンを各バイアル瓶に分注し、バイアル瓶を室温で3日間振動させる。固体を試料採取し、XRPDによって特徴付ける。
最初にスクリーニング実験を行い、純ニコチンからの結晶化による3,5−ジヒドロキシ安息香酸とのニコチン塩の形成を評価する。3,5−ジヒドロキシ安息香酸(25mg)を(S)−ニコチン(100μL)と複合し、混合物を室温で終夜撹拌する。3,5−ジヒドロキシ安息香酸はニコチンに溶解し、固体は観察されない。
最初にスクリーニング実験を行い、純ニコチンからの結晶化による2,3−ジヒドロキシ安息香酸とのニコチン塩の形成を評価する。2,3−ジヒドロキシ安息香酸(約25mg)を(S)−ニコチン(100μL)と複合し、混合物を室温で終夜振動させる。結果として得られる固体材料を試料採取し、XPRDによって特徴付ける(新たな形態を示す)。100mgスケールで研究を繰り返し、生成された固体を濾過によって単離し、ヘプタン(2×1mL)で洗浄し、XPRD及び1H NMRによって特徴付ける(1:1の化学量論を示した)。
最初にスクリーニング実験を行い、純ニコチンからの結晶化による2,3−ジヒドロキシ安息香酸とのニコチン塩の形成を評価する。1−ヒドロキシ−2−ナフトエ酸(約25mg)を(S)−ニコチン(100μL)と複合し、混合物を室温で終夜撹拌する。結果として得られる固体材料をサンプリングし、XPRDによって特徴付ける(新たな形態を示す)。100mgスケールで研究を繰り返し、生成された固体を濾過によって単離し、ヘプタン(2×1mL)で洗浄し、XPRD及び1H NMRによって特徴付ける(1:1の化学量論を示した)。
ニコチンムチン酸塩、ニコチン4−アセトアミド安息香酸塩、ニコチンゲンチジン酸塩、ニコチン3−ヒドロキシ安息香酸塩、ニコチンL−リンゴ酸塩、ニコチン3,5−ジヒドロキシ安息香酸塩、ニコチン2,3−ジヒドロキシ安息香酸塩、及びニコチン1−ヒドロキシ−2−ナフトエ酸塩を含む、ニコチンのいくつかの塩を、ヘリウム中650℃で熱分解して、加熱時に各塩から生成される熱分解生成物を評価する。全ての試料において、高収率のニコチンが生成され、ニコチンがこの評価された温度で塩から遊離することを示す。
ニコチンムチン酸塩、ニコチンサリチル酸塩、ニコチン4−アセトアミド安息香酸塩、ニコチンゲンチジン酸塩、ニコチン3−ヒドロキシ安息香酸塩、ニコチンL−リンゴ酸塩、ニコチン3,5−ジヒドロキシ安息香酸塩、ニコチン2,3−ジヒドロキシ安息香酸塩、及びニコチン1−ヒドロキシ−2−ナフトエ酸塩を含む、ニコチンのいくつかの塩を、トローチ剤の形態の無煙タバコ製品に組み込む。トローチ剤は、一般に、参照により本明細書に組み込まれる、米国特許出願公開第2013/0078307号(Holton,Jr.)に開示される成分を含み得る。例えば、代表的なトローチ剤は、イソマルト、マルチトールシロップ、風味材料(複数可)、水、及びニコチン化合物を含み得る(参考文献に開示されるニコチン化合物の代わりに使用される、本明細書に開示されるニコチン塩、共結晶、または塩共結晶のうちの1つ以上と共に)。各トローチ剤に含まれるニコチン塩、共結晶、または塩共結晶の量は、2mgのニコチンを提供するのに十分な量である(特定の共形成剤の重量に基づいて調整される)。感覚(例えば、味及び口の感覚)特徴及び/またはトローチ剤の安定性は、いくつかの実施形態において、ニコチン塩、共結晶、または塩共結晶の選択によって影響され得る。
Claims (16)
- ニコチン及びムチン酸の塩;ニコチン及び3,5−ジヒドロキシ安息香酸の塩;ニコチン及び2,3−ジヒドロキシ安息香酸の塩;ニコチン1−ヒドロキシ−2−ナフトエ酸塩の結晶多形形態であって、前記形態が、以下の2θ回折角、すなわち15.6、16.1、20.5、22.5、及び27.1のうちの1つ以上においてピークを有するX線粉末回折パターンによって特徴付けられる、結晶多形形態;ニコチン4−アセトアミド安息香酸塩の結晶多形形態であって、前記形態が、以下の2θ回折角、すなわち16.839、17.854、20.134、及び23.265のうちの1つ以上においてピークを有するX線粉末回折パターンによって特徴付けられる、結晶多形形態、ならびにニコチンゲンチジン酸塩の結晶多形形態であって、前記形態が、以下の2θ回折角、すなわち13.000、19.017、20.194、及び21.000のうちの1つ以上においてピークを有するX線粉末回折パターンによって特徴付けられる、結晶多形形態からなる群から選択される、ニコチン塩または結晶多形形態。
- ニコチン及びムチン酸の塩を含み、前記形態が、以下の2θ回折角、すなわち14.289、15,449、19.66、及び20.412のうちの1つ以上においてピークを有するX線粉末回折パターンによって特徴付けられる、請求項1に記載のニコチン塩または結晶多形形態。
- 前記塩または結晶多形形態の少なくとも約50%が、結晶形態である、請求項1に記載のニコチン塩または結晶多形形態。
- ニコチン及び3,5−ジヒドロキシ安息香酸の塩を含み、前記形態が、以下の2θ回折角、すなわち12.7、17.8、19.7、20.2、21.3、24.5、24.9、25.8、及び29.8のうちの1つ以上においてピークを有するX線粉末回折パターンによって特徴付けられる無水形態である、請求項1に記載のニコチン塩または結晶多形形態。
- ニコチン及び3,5−ジヒドロキシ安息香酸の塩を含み、前記形態が、以下の2θ回折角、すなわち10.7、13.4、15.0、17.2、17.3、19.0、21.4、21.6、22.2、22.6、22.9、24.3、25.1、25.5、及び29.7のうちの1つ以上においてピークを有するX線粉末回折パターンによって特徴付けられる水和形態である、請求項1に記載のニコチン塩または結晶多形形態。
- ニコチン及び2,3−ジヒドロキシ安息香酸の塩を含み、前記形態が、以下の2θ回折角、すなわち12.4、12.5、15.2、18.3、19.7、20.3、20.9、24.9、25.2、26.5、及び30.4のうちの1つ以上においてピークを有するX線粉末回折パターンによって特徴付けられる、請求項1に記載のニコチン塩または結晶多形形態。
- カートリッジ本体内に収容された吸入可能な物質媒体と、前記吸入可能な物質媒体の少なくとも一部分に熱を提供するように位置付けられた加熱部材と、を備える、電子喫煙物品であって、前記吸入可能な物質媒体が、請求項1に記載のニコチン塩または結晶多形形態のうちの1つ以上を含む、電子喫煙物品。
- 前記吸入可能な物質媒体が、グリセリン、水、及び風味材料のうちの1つ以上をさらに含む、請求項7に記載の電子喫煙物品。
- ニコチン塩または結晶多形形態の量が、前記物品の一吹き当たり約0.01mg〜約0.5mgの量のニコチンを提供するのに十分な量である、請求項7に記載の電子喫煙物品。
- ニコチン塩または結晶多形形態の量が、前記物品の一吹き当たり約0.05mg〜約0.3mgの量のニコチンを提供するのに十分な量である、請求項7に記載の電子喫煙物品。
- ニコチン塩または結晶多形形態の量が、前記物品の一吹き当たり約0.1mg〜約0.2mgの量のニコチンを提供するのに十分な量である、請求項7に記載の電子喫煙物品。
- 請求項1に記載のニコチン塩または結晶多形形態のうちの1つ以上を含む、無煙タバコ製品。
- ルース湿性嗅ぎタバコ(例えば、スヌース(snus));ルース乾性嗅ぎタバコ;噛みタバコ;ペレット状タバコ片;押出または形成されたタバコストリップ、小片、棒、円筒、またはスティック;微細化砕粉末;粉末状小片及び成分の微細化または微粉砕凝集体;フレーク様小片;成型タバコ片;ガム;テープ様フィルムのロール;易水溶性または水分散性フィルムまたはストリップ;溶融性組成物;トローチ剤;ドロップ;ならびに外殻及び内部領域を有するカプセル様物質からなる群から選択される、請求項12に記載の無煙タバコ製品。
- 請求項1に記載のニコチン塩または結晶多形形態のうちの1つ以上を含む、医薬製品。
- ピル、錠剤、トローチ剤、カプセル、カプレット、パウチ、ガム、吸入剤、溶液、及びクリームからなる群から選択される形態である、請求項14に記載の医薬製品。
- 請求項1に記載のニコチン塩または結晶多形形態のうちの1つ以上、及び少なくとも約50重量%のイソマルトを含む、トローチ剤。
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EP3148982A1 (en) | 2017-04-05 |
JP2020128376A (ja) | 2020-08-27 |
JP2022160452A (ja) | 2022-10-19 |
US20170334881A1 (en) | 2017-11-23 |
JP7168609B2 (ja) | 2022-11-09 |
US20200148664A1 (en) | 2020-05-14 |
EP3871515A1 (en) | 2021-09-01 |
US11136305B2 (en) | 2021-10-05 |
US20210395219A1 (en) | 2021-12-23 |
CN113816940A (zh) | 2021-12-21 |
US20150344456A1 (en) | 2015-12-03 |
CN113754634A (zh) | 2021-12-07 |
US9738622B2 (en) | 2017-08-22 |
WO2015183801A1 (en) | 2015-12-03 |
JP6745728B2 (ja) | 2020-08-26 |
US10556880B2 (en) | 2020-02-11 |
CN106536501A (zh) | 2017-03-22 |
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