JP5878928B2 - ベンプロペリン誘導体を有効成分として含有する、血管新生関連疾患の予防及び治療用組成物 - Google Patents
ベンプロペリン誘導体を有効成分として含有する、血管新生関連疾患の予防及び治療用組成物 Download PDFInfo
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- JP5878928B2 JP5878928B2 JP2013538655A JP2013538655A JP5878928B2 JP 5878928 B2 JP5878928 B2 JP 5878928B2 JP 2013538655 A JP2013538655 A JP 2013538655A JP 2013538655 A JP2013538655 A JP 2013538655A JP 5878928 B2 JP5878928 B2 JP 5878928B2
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- cancer
- benproperin
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- angiogenesis
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Description
文献に報告された方法を参考に反応式1により化学式2〜化学式4のベンプロペリン誘導体を合成した(非特許文献6)。
1H NMR(CDCl3):7.23(6H,m),7.09(1H,d,J=6.6),6.86(2H,t,8.1),4.07(1H,m),3.98(2H,s),3.85(1H,m),2.97(1H,m),2.54(4H,m),1.55(4H,m),1.42(2H,m),1.11(3H,d,J=6.6)
1H−NMR(CDCl3):7.28(7H,m),6.85(2H,m),4.12(1H,m),4.01(2H,m),3.85(2H,m),3.68(5H,m),2.57(4H,m),1.21(3H,m)
1H−NMR(CDCl3):7.3(1H,m),7.18(1H,m),7.04(2H,m),6.93(2H,m),6.80(2H,m),4.09(1H,m),4.01(2H,d,J=8.76),3.89(2H,d,J=8.79),2.71(5H,m),1.7(5H,m),1.17(3H,d,J=3.3)
参考例1で合成されたベンプロペリン誘導体の細胞毒性を検証するために、がん転移関連遺伝子であるPRL−3が過剰発現されたヒト大腸がん細胞株DLD−1細胞(ATCC CCL−221)を、10%ウシ胎児血清(FBS)を含むRPMI培地で37℃、5%CO2を維持して培養し、その後0.05%トリプシンEDTAを用いて細胞を採取した。10%FBS含有培地を含む96ウェルプレートの各ウェルに血球計数器(hematocytometer)で計数した4×103個の細胞を接種し、5%CO2を含む培養器にて37℃で培養した。24時間経過後、各ウェルの培地を、対照群(0.1%DMSO)と参考例1で合成された化学式2のベンプロペリンを各濃度(5及び10μM)で含む新鮮な培地に交換し、5%CO2培養器にて37℃で48時間培養した。前記プレートの各ウェルにWST−1(Roche)を10μlずつ添加して2時間培養し、その後ELISAリーダー(ELISA Reader, Bio-Rad)を用いて450nmにおける吸光度を測定した。
本発明によるベンプロペリン誘導体の試験管内の細胞移動阻害活性を分析するために、PRL−3が過剰発現された大腸がん細胞株DLD−1細胞(ATCC CCL−221)を、RPMI培地を含む培養皿で約90%成長させ、その後培地を除去してPBSで洗浄した。洗浄した細胞をトリプシンEDTAで処理し、CO2培養器にて37℃で15時間培養して細胞を採取した。これに10%FBS含有RPMI培地を添加してファルコンチューブ(falcon tube)に入れ、その後遠心分離して培地を除去した。得られた細胞にFBS非含有RPMI培地を添加し、遠心分離して培地を除去する過程を2回繰り返した。こうして得られた細胞にFBS非含有RPMI培地を添加して懸濁させ、その後血球計数器を用いて細胞数を計数した。
本発明によるベンプロペリンの血管新生阻害活性を、ヒト由来細胞株である血管内皮細胞HUVEC(Human Umbilical Vein Endothelial Cells)における試験管内の内皮形態形成(in vitro endothelial morphogenesis)分析法を用いて生体内と類似の環境で観察した。
本発明によるベンプロペリンの生体内の細胞移動阻害活性を分析するために、黒色腫細胞を移植した腫瘍モデルを用いてベンプロペリンのがん転移抑制活性を分析した。
本発明によるベンプロペリン及びその薬学的に許容される塩の毒性を確認するために、下記の通り実験動物における急性毒性実験を行った。
ベンプロペリン、その誘導体又はその薬学的に許容される塩……………………20mg
ラクトース……………………………………………………………………………100mg
タルク……………………………………………………………………………………10mg
ベンプロペリン、その誘導体又はその薬学的に許容される塩……………………10mg
トウモロコシデンプン………………………………………………………………100mg
ラクトース……………………………………………………………………………100mg
ステアリン酸マグネシウム………………………………………………………………2mg
ベンプロペリン、その誘導体又はその薬学的に許容される塩……………………10mg
結晶性セルロース…………………………………………………………………………3mg
ラクトース…………………………………………………………………………14.8mg
ステアリン酸マグネシウム…………………………………………………………0.2mg
ベンプロペリン、その誘導体又はその薬学的に許容される塩……………………10mg
マンニトール…………………………………………………………………………180mg
注射用滅菌蒸留水…………………………………………………………………2974mg
Na2HPO412H2O………………………………………………………………26mg
ベンプロペリン、その誘導体又はその薬学的に許容される塩……………………10mg
異性化糖……………………………………………………………………………………10g
マンニトール…………………………………………………………………………………5g
精製水…………………………………………………………………………………………適量
ベンプロペリン、その誘導体又はその薬学的に許容される塩……………………10mg
ビタミン混合物………………………………………………………………………………適量
ビタミンAアセテート…………………………………………………………………70μg
ビタミンE……………………………………………………………………………1.0mg
ビタミンB1………………………………………………………………………0.13mg
ビタミンB2………………………………………………………………………0.15mg
ビタミンB6…………………………………………………………………………0.5mg
ビタミンB12………………………………………………………………………0.2μg
ビタミンC………………………………………………………………………………10mg
ビオチン…………………………………………………………………………………10μg
ニコチン酸アミド……………………………………………………………………1.7mg
葉酸………………………………………………………………………………………50μg
パントテン酸カルシウム……………………………………………………………0.5mg
無機混合物……………………………………………………………………………………適量
硫酸第一鉄…………………………………………………………………………1.75mg
酸化亜鉛……………………………………………………………………………0.82mg
炭酸マグネシウム…………………………………………………………………25.3mg
第一リン酸カリウム……………………………………………………………………15mg
第二リン酸カルシウム…………………………………………………………………55mg
クエン酸カリウム………………………………………………………………………90mg
炭酸カルシウム………………………………………………………………………100mg
塩化マグネシウム…………………………………………………………………24.8mg
ベンプロペリン、その誘導体又はその薬学的に許容される塩……………………10mg
ビタミンC…………………………………………………………………………………15g
ビタミンE(粉末)……………………………………………………………………100g
乳酸鉄………………………………………………………………………………19.75g
酸化亜鉛…………………………………………………………………………………3.5g
ニコチン酸アミド………………………………………………………………………3.5g
ビタミンA………………………………………………………………………………0.2g
ビタミンB1…………………………………………………………………………0.25g
ビタミンB2……………………………………………………………………………0.3g
水………………………………………………………………………………………………定量
Claims (10)
- ベンプロペリン誘導体の薬学的に許容される塩がベンプロペリンリン酸塩、ベンプロペリンナトリウム塩、ベンプロペリンカリウム塩及びベンプロペリンマグネシウム塩からなる群から選択される請求項1または2に記載の薬学的組成物。
- がんが子宮頸がん、肺がん、膵がん、非小細胞肺がん、肝がん、結腸がん、骨肉腫、皮膚がん、頭部がん、頸部がん、皮膚黒色腫、眼球内黒色腫、子宮がん、卵巣がん、直腸がん、脳腫瘍、血液がん、胃がん、肛門周囲腺がん、乳がん、卵管がん、子宮内膜がん、膣がん、外陰がん、ホジキン病、食道がん、小腸がん、内分泌腺がん、甲状腺がん、副甲状腺がん、副腎がん、軟部組織肉腫、尿道がん、陰茎がん、前立腺がん、膀胱がん、腎がん、尿管がん、腎細胞がん、腎盂がん、中枢神経系腫瘍、原発性CNSリンパ腫、脊髄腫瘍、脳幹神経膠腫又は脳下垂体腺腫である請求項1〜3のいずれか一項に記載の薬学的組成物。
- 抗がん剤をさらに含む請求項1〜4のいずれか一項に記載の薬学的組成物。
- 抗がん剤がDNAアルキル化剤、抗がん性抗生物質及び植物アルカロイドからなる群から選択される少なくとも1種である請求項5に記載の薬学的組成物。
- 血管新生阻害剤をさらに含む請求項1〜6のいずれか一項に記載の薬学的組成物。
- ベンプロペリン誘導体の薬学的に許容される塩がベンプロペリンリン酸塩、ベンプロペリンナトリウム塩、ベンプロペリンカリウム塩及びベンプロペリンマグネシウム塩からなる群から選択される請求項8または9に記載の健康機能食品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20100112343 | 2010-11-11 | ||
KR10-2010-0112343 | 2010-11-11 | ||
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US8628554B2 (en) | 2010-06-13 | 2014-01-14 | Virender K. Sharma | Intragastric device for treating obesity |
US10010439B2 (en) | 2010-06-13 | 2018-07-03 | Synerz Medical, Inc. | Intragastric device for treating obesity |
US9526648B2 (en) | 2010-06-13 | 2016-12-27 | Synerz Medical, Inc. | Intragastric device for treating obesity |
US10420665B2 (en) | 2010-06-13 | 2019-09-24 | W. L. Gore & Associates, Inc. | Intragastric device for treating obesity |
CN103626722B (zh) * | 2012-08-27 | 2016-06-01 | 天津药物研究院 | 一氧化氮供体型降血糖化合物、其制备方法和用途 |
CN104784122A (zh) * | 2014-01-20 | 2015-07-22 | 广东东阳光药业有限公司 | 一种包含苯丙哌林的固体制剂 |
KR20160041746A (ko) * | 2014-10-07 | 2016-04-18 | 한국생명공학연구원 | (s)-(-)-벤프로페린을 포함하는 암 예방 또는 치료용 조성물 |
US10779980B2 (en) | 2016-04-27 | 2020-09-22 | Synerz Medical, Inc. | Intragastric device for treating obesity |
KR102259291B1 (ko) * | 2018-05-04 | 2021-06-01 | 주식회사 브이에스팜텍 | 암 세포의 이동과 침윤 억제를 통한 암 전이 억제제 |
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