JP2010516749A - 治療用化合物のトシル酸塩およびその医薬組成物 - Google Patents
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Abstract
【図1】
Description
(i)適切な溶媒に溶かした式1の化合物を、パラ−トルエンスルホン酸(一般に、トシル酸と称される)と接触させるステップと、
(ii)形成した結晶を回収するステップとを含む。
1(a).結晶化度
試料を、シリコーン油中に調製し、交差分極光下で観察した。試料は、結晶質であり、多少の凝集体を伴う高複屈折不規則プリズム形状粒子を含有する。試料中で、非晶質物質は観察されなかった。
粉末X線回折図を、本発明のトシル酸塩について、銅放射線源、固定スリット(拡散1.0mm、散乱線除去体1.0mmおよび受信0.6mm)およびSolex固体検出器を備えたBruker D5000回折計(Madison、Wisconsin)を使用して集めた。データを、シータ−2(2θ)シータゴニオメーター構成で、平板試料ホルダーから、銅波長Kα1=1.54056およびKα2=1.54439(相対強度0.5)で、3.0から40.0度までの2シータで、0.040度のステップサイズおよび1秒のステップ時間を使用して集めた。X線管電圧およびアンペア数を、それぞれ40kVおよび30mAに設定した。
示差走査熱分析により、約161℃の開始温度での単一吸熱イベント(ΔH=100.4J/g)、続いて、約175℃で開始する発熱イベントが同定された(図2参照)。これは、ホットステージ溶融顕微鏡法の間に観察された物質の溶融および分解と一致する。
当初乾燥サイクル(25℃、相対湿度1%)の間、0.1%未満の重量損失が観察され、これは、無水非吸湿性形態と一致する。試料を相対湿度5%から90%に25℃で曝露すると、重量の約0.06%の上昇が、DVS分析により検出された。相対湿度が5%に低下すると、放出相は、吸収相に似る。加えて、吸湿性試験後の試料での粉末X線回折図は、試験前の試料の図と一致した。
次の情報は、水溶性に関して決定した。本発明のトシル酸塩は、0.1Mのリン酸緩衝溶液(最終pH6.5)中で10mg/mLを超える溶解性;6.5の最終pHで、タウロコール酸ナトリウム/ホスファチジルコリン塩0.5重量%を伴う0.1Mのリン酸緩衝溶液中で11mg/mLを超える溶解性;および非緩衝水(最終pH3.8)中で23.6mg/mLを有する。これらの値は、薬物媒体混合物を温度サイクルプログラム(40℃で8時間、15℃で5時間および25℃で12時間)に掛けた後にRP−HPLC分析を介して決定された結晶質化合物の溶解性を示している。
実施例1−トランス−N−エチル−3−フルオロ−3−[3−フルオロ−4−(ピロリジン−1−イルメチル)フェニル]−シクロ−ブタンカルボキサミドのトシル酸塩
p−トルエンスルホン酸(2.50g、13.14mmol)の酢酸エチル(70mL)溶液を、撹拌されているトランス−N−エチル−3−フルオロ−3−[3−フルオロ−4−(ピロリジン−1−イルメチル)フェニル]−シクロブタンカルボキサミド(4.18g、12.97mmol)の酢酸エチル(35mL)溶液に20分にわたって加えた。生じた混合物をさらに1時間撹拌した。白色の沈殿物を濾過し、EtOAcですすぎ、空気乾燥させると、トシル酸塩6.32gが得られた。この物質をメタノールに溶かし、濾過して、微粒子を除去し、再濃縮した。生じた固体をメタノール約12〜14mLに、穏やかに加熱しながら溶かした。酢酸エチル(75mL)を20分にわたって加え、次いで、混合物を室温で1時間撹拌した。固体を濾過し、酢酸エチルですすぎ、空気乾燥させると、(トランス)−3−フルオロ−3−[3−フルオロ−4−(ピロリジン−1−イルメチル)フェニル]シクロブタンカルボン酸エチルアミドトシル酸塩5.59gが白色の結晶粉末として得られた。
1H NMR(CDCl3)δ 7.71(d,J=8.3Hz,2H)、7.65(t,J=7.9Hz,1H)、7.28〜7.22(m,2H)、7.15(d,J=7.9Hz,2H)、6.52(br s,1H)、4.28(d,J=5.4Hz,2H)、3.68〜3.37(m,2H)、3.33〜3.18(m,3H)、2.97〜2.88(m,2H)、2.84〜2.57(m,4H)、2.32(s,3H)、2.27〜1.96(m,4H)、1.07(t,J=7.3Hz,3H)。
13C NMR(CDCl3)δ 173.8、161.3(d,JC−F=248.7Hz)、147.4(dd,JC−F=24.1,7.5Hz)、142.4、140.4、133.5、129.1、126.0、121.7(d,JC−F=6.0Hz)、116.4(d,JC−F=14.3Hz)、112.6(dd,JC−F=23.3,9.0Hz)、96.7(d,JC−F=197.6Hz)、53.4、50.4、39.0、38.7、34.7、32.6、23.0、21.52、14.9。
Claims (12)
- トランス−N−エチル−3−フルオロ−3−[3−フルオロ−4−(ピロリジン−1−イルメチル)−フェニル]−シクロブタンカルボキサミドのトシル酸塩。
- 8.959±0.2の2θでの銅(Kα1=1.54056、Kα2=1.54439)放射線で測定されるX線回折図ピークにより実質的に特徴づけられるX線回折図を有する、請求項1または2に記載のトシル酸塩。
- 17.991±0.2の2θでの銅(Kα1=1.54056、Kα2=1.54439)放射線で測定されるX線回折図ピークにより実質的に特徴づけられるX線回折図を有する、請求項1または2に記載のトシル酸塩。
- 21.054±0.2の2θでの銅(Kα1=1.54056、Kα2=1.54439)放射線で測定されるX線回折図ピークにより実質的に特徴づけられるX線回折図を有する、請求項1または2に記載のトシル酸塩。
- 22.590±0.2の2θでの銅(Kα1=1.54056、Kα2=1.54439)放射線で測定されるX線回折図ピークにより実質的に特徴づけられるX線回折図を有する、請求項1または2のいずれかに記載のトシル酸塩。
- 28.050±0.2の2θでの銅(Kα1=1.54056、Kα2=1.54439)放射線で測定されるX線回折図ピークにより実質的に特徴づけられるX線回折図を有する、請求項1または2のいずれかに記載のトシル酸塩。
- 15.515(±0.2)の2θでの銅(Kα1=1.54056、Kα2=1.54439)放射線で測定されるX線回折図ピークにより実質的に特徴づけられるX線回折図を有する、請求項1または2に記載のトシル酸塩。
- 8.959;15.515;17.991;21.054;22.590;および28.050の2θ(±0.2)での銅(Kα1=1.54056、Kα2=1.54439)放射線で測定されるX線回折図ピークにより実質的に特徴づけられるX線回折図を有する、請求項1または2に記載のトシル酸塩。
- 前記塩が無水である、請求項1または2に記載のトシル酸塩。
- 請求項1から10のいずれかに記載のトシル酸塩および薬学的に許容できる担体を含む医薬組成物。
- 哺乳動物におけるうつ病、気分障害、統合失調症、不安障害、認識障害、アルツハイマー病、注意欠陥障害(ADD)、注意欠陥多動障害(ADHD)、精神病、睡眠障害、肥満、めまい、てんかん、乗り物酔い、呼吸疾患、アレルギー、アレルギー誘発気道応答、アレルギー性鼻炎、鼻詰まり、アレルギー性うっ血、うっ血、低血圧、心臓血管疾患、胃腸管の疾患、胃腸管の亢進および減弱した運動および酸分泌を治療する方法であって、治療を必要とする対象に、治療有効量の請求項1または請求項2に記載のトシル酸塩を投与することを含む方法。
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WO2007150010A2 (en) * | 2006-06-23 | 2007-12-27 | Abbott Laboratories | Cyclopropyl amine derivatives as histamin h3 receptor modulators |
CA2708043C (en) * | 2007-12-07 | 2012-11-13 | Pfizer Inc. | Tosylate salt of trans-n-isobutyl-3-fluoro-3- [3-fluoro-4- (pyrrolidin-1-yl-methyl) -phenyl] cyclobut anecarboxamide |
US8383657B2 (en) * | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
US20090221648A1 (en) * | 2007-12-21 | 2009-09-03 | Abbott Laboratories | Compositions for treatment of cognitive disorders |
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