JP2018513139A - セミカルバジド感受性アミンオキシダーゼ酵素阻害剤としての結晶性化合物 - Google Patents
セミカルバジド感受性アミンオキシダーゼ酵素阻害剤としての結晶性化合物 Download PDFInfo
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Abstract
Description
定義
本明細書で用いられる「治療」は、名前が付けられている疾患若しくは病状の予防、またはいったん確立された前記疾患の改善若しくは除去を含む。
組成物
実験方法
分析方法
X線粉末回折(XRPD)
核磁気共鳴(NMR)
液体クロマトグラフィー−質量分析(LCMS)
示差走査熱量分析(DSC)
熱重量分析(TGA)
偏光顕微鏡観察(PLM)
加熱ステージ顕微鏡観察(HSM)[融点]
HPLCによる化学的純度測定
キラルHPLCによるキラル純度測定
カールフィッシャー滴定(KF)による水分測定
重量法蒸気吸着測定(GVS)
イオンクロマトグラフィー(IC)
結果
長期間保存時の安定性/吸湿性
単結晶X線回折(SXRPD)
単結晶構造決定
最終差マップ+0.24〜−0.288eÅ−3の間。
解析した結晶構造パラメータは以下の通り(表3):
原子座標は以下の通り:
合成
以下の略号が用いられた:
Aq 水性
DCM ジクロロメタン
DIPEA ジイソピロピルエチルアミン
ee 鏡像体過剰率
ES+ エレクトロスプレー
EtOAc 酢酸エチル
h 時間(単数又は複数)
HPLC 高速液体クロマトグラフィー
HRMS 高分解能質量分析
LCMS 液体クロマトグラフィー−質量分析
M モル
MeOH メタノール
[MH+] プロトン付加分子イオン
min 分
RP 逆相
MS 質量分析
RT 保持時間
sat 飽和した
THF テトラヒドロフラン
TFA トリフルオロ酢酸
実験方法
分析LCMSはAgilent 1100 HPLCシステムに接続したWaters ZQ質量分析計で行った。分析HPLCはAgilent 1100システムで行った。高分解能質量スペクトル(HRMS)はAgilent 1100 HPLCシステムに接続したAgilent MSD-TOFで得た。分析の間、較正は2つの質量でチェックし、必要に応じて自動的に補正した。スペクトルは正イオンエレクトロスプレーモードで収集した。収集質量範囲はm/z100〜1100であった。質量ピークのプロファイル検出を用いた。フラッシュクロマトグラフィーはRediSepシリカカラムを備えたCombiFlash Companionシステム、またはStrata SI-1シリカギガチューブを備えたFlash Master Personalのいずれかで行った。逆相HPLCはPhenomenex Synergi Hydro RP150x10mm、YMC ODS-A100/150x20mmまたはChirobiotic T250x10mmカラムを備えたGilson システム(Gilson 321平衡ポンプ付きGilson 322ポンプ、およびGilson 215オートサンプラー)で行った。逆相カラムクロマトグラフィーはMerck LiChroprep(登録商標)RP-18(40−63μm)シリカカラムを備えたGilsonシステム(Gilson 321ポンプおよびGilson FC204フラクションコレクター)で行った。化合物はACD6.0を用いて自動的に命名した。すべての化合物は真空ポンプ中で一晩乾燥した。
分析HPLCおよびLCMSデータは以下の条件で得た:
キラルHPLCで他は以下の条件で得た:
中間体1
4−イソプロピル−4,5,6,7−テトラヒドロ−1H−イミダゾ[4,5−c]ピリジンハイドロクロライド
分析LCMS:純度>90%(システムA、RT=0.51分)、ES+:166.4[MH]+。
中間体2
4−ニトロフェニル 4−イソプロピル−1,4,6,7−テトラヒドロ−5H−イミダゾ[4,5−c]ピリジン−5−カルボキシレート
Claims (22)
- 空間群P2(1)2(1)2(1)および実質的に以下に示す単位格子寸法を有する結晶性(3S)−テトラヒドロフラン−3−イル (4S)−4−イソプロピル−1,4,6,7−テトラヒドロ−5H−イミダゾ[4,5−c]ピリジン−5−カルボキシレートメシレート塩:
- CuKα線を用いて測定した以下の2θ値:21.948を含むXRPDパターンを有する結晶性(3S)−テトラヒドロフラン−3−イル (4S)−4−イソプロピル−1,4,6,7−テトラヒドロ−5H−イミダゾ[4,5−c]ピリジン−5−カルボキシレートメシレート塩。
- CuKα線を用いて測定した以下の2θ値:17.744および21.948を含むXRPDパターンを有する請求項2に記載の塩。
- CuKα線を用いて測定した以下の2θ値:17.744、20.886、21.948を含むXRPDパターンを有する請求項2または請求項3に記載の塩。
- CuKα線を用いて測定した以下の2θ値:17.744、20.886、21.948、および9.851を含むXRPDパターンを有する請求項2から4のいずれか1項に記載の塩。
- CuKα線を用いて測定した以下の2θ値:17.744、20.886、21.948、9.851および16.280を含むXRPDパターンを有する請求項2から5のいずれか1項に記載の塩。
- CuKα線を用いて測定した以下の2θ値:9.851、16.280、17.097、17.744、19.694、20.443、20.886、21.948、22.112、23.194、23.653、24.144、27.084、27.283、および29.912を含むXRPDパターンを有する請求項2から6のいずれか1項に記載の塩。
- 表4および/または図2に提示したXRPDパターンを有する請求項2から7のいずれか1項に記載の塩。
- 95%より高い純度を有する請求項1から8のいずれか1項に記載の塩。
- 99%より高い純度を有する請求項1から8のいずれか1項に記載の塩。
- 99.5%より高い純度を有する請求項1から8のいずれか1項に記載の塩。
- 95%より高い鏡像異性純度を有する請求項1から11のいずれか1項に記載の塩。
- 99%より高い鏡像異性純度を有する請求項1から11のいずれか1項に記載の塩。
- 99.5%より高い鏡像異性純度を有する請求項1から11のいずれか1項に記載の塩。
- 請求項1から14のいずれか1項に記載の塩および1種以上の適切な賦形剤を含む医薬用組成物。
- 炎症、炎症性疾患、免疫若しくは自己免疫疾患、または腫瘍成長の阻害の治療における、あるいは治療のための薬剤の製造における使用のための請求項1から14のいずれか1項に記載の塩または請求項15に記載の医薬用組成物。
- 炎症、炎症性疾患、免疫若しくは自己免疫疾患、または腫瘍成長の阻害の治療方法であって、そのような疾患を患っている患者に請求項1から14のいずれか1項に記載の塩または請求項15に記載の医薬用組成物の有効量を投与することを含む方法。
- 前記炎症、または炎症性疾患、または免疫若しくは自己免疫疾患は、関節炎(関節リウマチ、若年性関節リウマチ、変形性関節炎、乾癬性関節炎を含む)、滑膜炎、血管炎、シェーグレン疾患、腸の炎症と関係している状態(クローン病、潰瘍性大腸炎、炎症性大腸炎および過敏性腸症候群を含む)、アテローム性動脈硬化症、多発性硬化症、アルツハイマー病、血管性認知症、パーキンソン病、脳アミロイド血管症、皮質下梗塞および白質脳症を伴う常染色体優性脳動脈症、肺炎症疾患(ぜんそく、慢性閉塞性肺疾患、および呼吸窮迫症候群を含む)、線維性疾患(特発性肺線維症、心臓線維症、肝線維症、および全身性硬化症(強皮症)を含む)、皮膚の炎症性疾患(接触性皮膚炎、アトピー性皮膚炎、および乾癬を含む)、眼の炎症性疾患(加齢性黄斑変性症、ブドウ膜炎、および糖尿病性網膜症を含む)、全身性炎症反応症候群、敗血症、肝臓の炎症性および/または自己免疫性疾患(自己免疫性肝炎、原発性胆汁性肝硬変、アルコール性肝臓疾患、硬化性胆管炎、および自己免疫性胆管炎を含む)、糖尿病(1型または2型)および/またはその合併症、慢性心不全、鬱血性心不全、虚血症(脳卒中、および虚血−再潅流障害を含む)若しくは心筋梗塞および/またはその合併症、あるいはてんかんである、請求項16に記載の塩または請求項17に記載の方法。
- リウマチ性関節炎、変形性関節炎、肝線維症、慢性閉塞性肺疾患、多発性硬化症、シェーグレン疾患、アルツハイマー病、パーキンソン病、炎症性大腸炎または血管性認知症から選択される疾患の治療のための請求項16に記載の塩または請求項17に記載の方法。
- (3S)−テトラヒドロフラン−3−イル (4S)−4−イソプロピル−1,4,6,7−テトラヒドロ−5H−イミダゾ[4,5−c]ピリジン−5−カルボキシレートの遊離塩基からメシレート塩を形成することによる結晶性(3S)−テトラヒドロフラン−3−イル (4S)−4−イソプロピル−1,4,6,7−テトラヒドロ−5H−イミダゾ[4,5−c]ピリジン−5−カルボキシレートメシレート塩の製造方法。
- 前記メシレート塩は、遊離塩基にメタンスルホン酸を加えて形成される請求項20に記載の方法。
- 請求項20または請求項21に記載の方法で得られた結晶性(3S)−テトラヒドロフラン−3−イル (4S)−4−イソプロピル−1,4,6,7−テトラヒドロ−5H−イミダゾ[4,5−c]ピリジン−5−カルボキシレートメシレート塩。
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JP2018520984A (ja) * | 2015-04-24 | 2018-08-02 | ベネボレンタイ ケンブリッジ リミティド | 疼痛の治療 |
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