KR20030078117A - 푸마질롤 유도체 또는 그 염의 포접 화합물, 및 이를포함하는 약제학적 조성물 - Google Patents
푸마질롤 유도체 또는 그 염의 포접 화합물, 및 이를포함하는 약제학적 조성물 Download PDFInfo
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Abstract
Description
히드록시프로필-β-시클로덱스트린 농도(w/v%) | 용해도(mg/ml) |
0 | 0.05 |
1.5 | 1.03 |
3.5 | 2.93 |
7.0 | 6.95 |
14.0 | 11.54 |
28.0 | 22.64 |
술포부틸에테르-7-β-시클로덱스트린 농도(w/v%) | 용해도(mg/ml) |
0 | 0.05 |
1.5 | 0.87 |
3.5 | 2.24 |
7.0 | 5.42 |
14.0 | 10.43 |
28.0 | 21.30 |
히드록시프로필-β-시클로덱스트린 농도(w/v%) | 용해도(mg/ml) |
0 | 0.002 |
1.5 | 0.43 |
3.5 | 1.52 |
7.0 | 3.54 |
14.0 | 6.72 |
28.0 | 12.02 |
술포부틸에테르-7-β-시클로덱스트린 농도(w/v%) | 용해도(mg/ml) |
0 | 0.002 |
1.5 | 0.58 |
3.5 | 1.38 |
7.0 | 2.75 |
14.0 | 5.69 |
28.0 | 11.67 |
히드록시프로필-β-시클로덱스트린 농도(w/v%) | 용해도(mg/ml) |
0 | 2.38 |
1.5 | 4.24 |
3.5 | 9.86 |
7.0 | 17.59 |
14.0 | 32.25 |
O-(4-디메틸아미노에톡시신나모일)푸마질롤의 잔존률 | ||||
1개월 경과 | 3개월 경과 | 6개월 경과 | 12개월 경과 | |
O-(4-디메틸아미노에톡시신나모일)푸마질롤 | 72.8 | 54.3 | - | - |
O-(4-디메틸아미노에톡시신나모일)푸마질롤의 포접화합물 | 99.3 | 98.7 | 97.5 | 93.6 |
O-(3, 4, 5-트리메톡시신나모일)푸마질롤의 잔존률(%) | ||||
1개월 경과 | 3개월 경과 | 6개월 경과 | 12개월 경과 | |
O-(3, 4, 5-트리메톡시신나모일)푸마질롤 | 65.3 | - | - | - |
O-(3, 4, 5-트리메톡시신나모일)푸마질롤의 포접화합물 | 99.5 | 97.7 | 94.4 | 93.2 |
산성(pH 3.2) | 중성(pH 7.2) | 염기성(pH 11.5) | ||||
히드록시프로필-β-시클로덱스트린의 농도(w/v%) | 분해속도 상수(h-1) | 억제율(%) | 분해속도 상수(h-1) | 억제율(%) | 분해속도 상수(h-1) | 억제율(%) |
0 | 0.2042 | - | 0.0162 | - | 0.0918 | - |
2 | 0.0976 | 52.20 | 0.0141 | 12.96 | 0.0816 | 5.00 |
5 | 0.0848 | 58.47 | 0.0137 | 15.43 | 0.0580 | 16.55 |
10 | 0.0754 | 63.08 | 0.0122 | 24.96 | 0.0453 | 22.77 |
20 | 0.0665 | 67.43 | 0.0115 | 29.01 | 0.0294 | 30.56 |
총 투여용량(mg/kg) | 억제율(%) | ||
암조직 부피 | 암조직 무게 | ||
대조군 | 150 | 0 | 0 |
600 | 0 | 0 | |
O-(4-디메틸아미노에톡시신나모일)푸마질롤 투여군 | 150 | 37.7 | 33.6 |
600 | 63.3 | 71.4 | |
O-(4-디메틸아미노에톡시신나모일)푸마질롤의 포접화합물 투여군 | 150 | 32.2 | 34.7 |
600 | 60.4 | 70.8 |
Claims (18)
- 하기 화학식 (1)의 푸마질롤 유도체 또는 그 염과 히드록시프로필-β-시클로덱스트린 또는 술포부틸에테르-7-β-시클로덱스트린과의 포접 화합물.화학식 (1)(식중, X는 히드록시, Y는 할로겐이거나, 또는 X와 Y는 함께 옥시란 고리를 형성하며,B는 O 또는 H2이고,R1, R2, R3,R4및 R5는 각각 독립적으로 수소, 히드록시, 아세톡시, C1∼C6알킬, C1∼C6알콕시, 아미노, 알킬아미노, 디알킬아미노, 아미노알킬, 알킬아미노알킬, 디알킬아미노알킬, 아미노알콕시, 알킬아미노알콕시, 디알킬아미노알콕시, 할로겐, 시아노, 트리플루오로메틸, 니트로, 포르밀, 아세트아미도, 메틸렌옥시카르복시, 메틸렌디옥시 또는 에틸렌디옥시기이며, R1, R2, R3,R4및 R5는 동시에 수소일수는 없다.)
- 제 1항에 있어서, 상기 푸마질롤 유도체 또는 그 염이,O-(4-클로로신나모일)푸마질롤;O-(4-아미노신나모일)푸마질롤;O-(4-디메틸아미노에톡시신나모일)푸마질롤;O-(4-메톡시신나모일)푸마질롤;O-(4-디메틸아미노신나모일)푸마질롤;O-(4-히드록시신나모일)푸마질롤;O-(3, 4-디메톡시신나모일)푸마질롤;O-(3, 4-메틸렌디옥시신나모일)푸마질롤;O-(3, 4, 5-트리메톡시신나모일)푸마질롤;O-(4-니트로신나모일)푸마질롤;O-(3, 4-디메톡시-6-아미노신나모일)푸마질롤;O-(4-아세톡시-3, 5-디메톡시신나모일)푸마질롤;O-(4-에틸아미노신나모일)푸마질롤;O-(4-에틸아미노에톡시신나모일)푸마질롤;O-(3-디메틸아미노메틸-4-메톡시신나모일)푸마질롤;O-(4-트리플루오로메틸신나모일)푸마질롤;O-(3, 4-디메톡시-6-니트로신나모일)푸마질롤;O-(4-아세톡시신나모일)푸마질롤;O-(4-시아노신나모일)푸마질롤;4-(4-메톡시신나모일)옥시-2-(1, 2-에폭시-1, 5-디메틸-4-헥세닐)-3-메톡시-1-클로로메틸-1-시클로헥사놀;O-(3, 4, 5-트리메톡시신나밀)푸마질롤;O-(4-디메틸아미노신나밀)푸마질롤;O-(3, 4, 5-트리메톡시신나모일)옥시-2-(1, 2-에폭시-1,5-디메틸-4-헥세닐)-3-메톡시-1-클로로메틸-1-시클로헥사놀;O-(4-디메틸아미노신나모일)옥시-2-(1, 2-에폭시-1, 5-디메틸-4-헥세닐)-3-메톡시-1-클로로메틸-1-시클로헥사놀;O-(3, 5-디메톡시-4-히드록시신나모일)푸마질롤 또는 이들의 염인 것을 특징으로 하는 포접화합물.
- 제 1항에 있어서, 상기 푸마질롤 유도체 또는 그 염이,4-(4-메톡시신나모일)옥시-2-(1, 2-에폭시-1, 5-디메틸-4-헥세닐)-3-메톡시-1-클로로메틸-1-시클로헥사놀;O-(4-메톡시신나모일)푸마질롤;O-(3, 5-디메톡시-4-히드록시신나모일)푸마질롤;O-(4-디메틸아미노에톡시신나모일)푸마질롤;O-(3, 4, 5-트리메톡시신나모일)푸마질롤;O-(3, 4-디메톡시-6-아미노신나모일)푸마질롤 또는 이들의 염인 것을 특징으로 하는 포접화합물.
- 제 1항에 있어서, 상기 푸마질롤 유도체 또는 그 염이 O-(4-디메틸아미노에톡시신나모일)푸마질롤 또는 O-(3, 4, 5-트리메톡시신나모일)푸마질롤인 것을 특징으로 하는 포접화합물.
- 제 1항 내지 4항 중 어느 한 항에 있어서, 푸마질롤 유도체의 염이 푸마질롤 유도체와 염산, 브롬산, 황산, 인산, 질산, 포름산, 초산, 트리플루오로아세트산, 옥살산, 푸마르산, 주석산, 말레인산, 메탄술폰산, 벤젠술폰산 및 파라톨루엔술폰산의 염으로 이루어진 군으로부터 선택된 것임을 특징으로 하는 포접화합물.
- 제 1항에 있어서, 히드록시프로필-β-시클로덱스트린 또는 술포부틸에테르-7-β-시클로덱스트린을 증류수에 가하여 용해시킨 후, 푸마질롤 유도체 또는 그 염을 가하여 진탕함으로써 제조되는 것을 특징으로 하는 포접화합물.
- 제 1항에 있어서, 히드록시프로필-β-시클로덱스트린 또는 술포부틸에테르-7-β-시클로덱스트린을 증류수에 가하여 용해시키고, 희석염산 또는 수산화나트륨 용액을 사용하여 pH 6-8의 범위로 조절한 후, 푸마질롤 유도체 또는 그 염을 가하여 진탕함으로써 제조되는 것을 특징으로 하는 포접화합물.
- 제 1항에 있어서, 인산염을 사용하여 pH 6-8 범위로 조절한 완충액에 히드록시프로필-β-시클로덱스트린 또는 술포부틸에테르-7-β-시클로덱스트린을 가하여 용해시킨 후, 푸마질롤 유도체 또는 그 염을 가하여 진탕함으로써 제조되는 것을 특징으로 하는 포접화합물.
- 제 6항 내지 8항중 어느 한 항에 있어서, 진탕 후 얻어진 최종용액을 동결건조하는 단계를 더 포함하는 제조방법에 의해 얻어지는 것을 특징으로 하는 포접화합물.
- 제 6 내지 8항 중 어느 한 항에 있어서, 푸마질롤 유도체 또는 그 염에 대해 히드록시프로필-β-시클로덱스트린 또는 술포부틸에테르-7-β-시클로덱스트린이 1:1 내지 1:10의 몰비로 사용되는 것을 특징으로 하는 포접화합물.
- 제 1항의 포접화합물과 약제학적으로 허용가능한 첨가제를 포함하는 약제학적 조성물.
- 제 11항에 있어서, 약제학적으로 허용가능한 첨가제가 약제학적으로 허용가능한 희석제, 완충제, 향미제, 결합제, 점조제, 활택제 및 방부제로 이루어진 군으로부터 선택된 1종 이상의 성분임을 특징으로 하는 약제학적 조성물.
- 제 12항에 있어서, 상기 완충제가 인산염 완충제 인것을 특징으로 하는 약제학적 조성물.
- 제 11항에 있어서, 경구 또는 비경구 제제의 형태로 제형화되는 것을 특징으로 하는 약제학적 조성물.
- 제 14항에 있어서, 비경구 제제가 주사제인 것을 특징으로 하는 약제학적 조성물.
- 제 11항에 있어서, 서방성 제제의 형태로 제형화되는 것을 특징으로 하는 약제학적 조성물.
- 제 1항의 포접화합물을 유효성분으로 포함하는 항암제.
- 제 1항의 포접화합물을 유효성분으로 포함하는 암전이 억제제.
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2002-0016946A KR100451485B1 (ko) | 2002-03-28 | 2002-03-28 | 푸마질롤 유도체 또는 그 염의 포접 화합물, 및 이를포함하는 약제학적 조성물 |
JP2003580312A JP4202273B2 (ja) | 2002-03-28 | 2002-04-03 | フマギロール誘導体又はその塩の包接化合物、及び該包接化合物を含む医薬組成物 |
AU2002246411A AU2002246411A1 (en) | 2002-03-28 | 2002-04-03 | Inclusion compounds of fumagillol derivative or its salt, and pharmaceutical compositions comprising the same |
PCT/KR2002/000583 WO2003082845A1 (en) | 2002-03-28 | 2002-04-03 | Inclusion compounds of fumagillol derivative or its salt, and pharmaceutical compositions comprising the same |
US10/951,164 US20050037994A1 (en) | 2002-03-28 | 2004-09-27 | Inclusion compounds of fumagillol derivative or its salt, and pharmaceutical compositions comprising the same |
US11/828,025 US7718695B2 (en) | 2002-03-28 | 2007-07-25 | Inclusion compounds of fumagillol derivative or its salt, and pharmaceutical compositions comprising the same |
US12/756,372 US20110034550A1 (en) | 2002-03-28 | 2010-04-08 | Inclusion Compounds of Fumagillol Derivative or its Salt, and Pharmaceutical Compositions Comprising the Same |
US13/414,215 US20130029936A1 (en) | 2002-03-28 | 2012-03-07 | Inclusion Compounds of Fumagillol Derivative or its Salt, and Pharmaceutical Compositions Comprising the Same |
US13/924,768 US20140155348A1 (en) | 2002-03-28 | 2013-06-24 | Inclusion Compounds of Fumagillol Derivative or its Salt, and Pharmaceutical Compositions Comprising the Same |
US14/502,101 US20150238634A1 (en) | 2002-03-28 | 2014-09-30 | Inclusion Compounds of Fumagillol Derivative or its Salt, and Pharmaceutical Compositions Comprising the Same |
US15/252,625 US20170209596A1 (en) | 2002-03-28 | 2016-08-31 | Inclusion Compounds of Fumagillol Derivative or its Salt, and Pharmaceutical Compositions Comprising the Same |
US15/793,501 US20180271999A1 (en) | 2002-03-28 | 2017-10-25 | Inclusion Compounds of Fumagillol Derivative or its Salt, and Pharmaceutical Compositions Comprising the Same |
US16/366,408 US20200054766A1 (en) | 2002-03-28 | 2019-03-27 | Inclusion Compounds of Fumagillol Derivative or its Salt, and Pharmaceutical Compositions Comprising the Same |
Applications Claiming Priority (1)
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KR10-2002-0016946A KR100451485B1 (ko) | 2002-03-28 | 2002-03-28 | 푸마질롤 유도체 또는 그 염의 포접 화합물, 및 이를포함하는 약제학적 조성물 |
Publications (2)
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KR20030078117A true KR20030078117A (ko) | 2003-10-08 |
KR100451485B1 KR100451485B1 (ko) | 2004-10-06 |
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KR10-2002-0016946A KR100451485B1 (ko) | 2002-03-28 | 2002-03-28 | 푸마질롤 유도체 또는 그 염의 포접 화합물, 및 이를포함하는 약제학적 조성물 |
Country Status (5)
Country | Link |
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US (9) | US20050037994A1 (ko) |
JP (1) | JP4202273B2 (ko) |
KR (1) | KR100451485B1 (ko) |
AU (1) | AU2002246411A1 (ko) |
WO (1) | WO2003082845A1 (ko) |
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KR100789379B1 (ko) * | 2005-11-25 | 2007-12-28 | 한국전자통신연구원 | 멀티캐스트 트래픽 조정 기능을 가지는 홈게이트웨이 장치및 그 방법 |
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2002
- 2002-03-28 KR KR10-2002-0016946A patent/KR100451485B1/ko active IP Right Grant
- 2002-04-03 JP JP2003580312A patent/JP4202273B2/ja not_active Expired - Lifetime
- 2002-04-03 AU AU2002246411A patent/AU2002246411A1/en not_active Abandoned
- 2002-04-03 WO PCT/KR2002/000583 patent/WO2003082845A1/en active Application Filing
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2004
- 2004-09-27 US US10/951,164 patent/US20050037994A1/en not_active Abandoned
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2007
- 2007-07-25 US US11/828,025 patent/US7718695B2/en not_active Expired - Lifetime
-
2010
- 2010-04-08 US US12/756,372 patent/US20110034550A1/en not_active Abandoned
-
2012
- 2012-03-07 US US13/414,215 patent/US20130029936A1/en not_active Abandoned
-
2013
- 2013-06-24 US US13/924,768 patent/US20140155348A1/en not_active Abandoned
-
2014
- 2014-09-30 US US14/502,101 patent/US20150238634A1/en not_active Abandoned
-
2016
- 2016-08-31 US US15/252,625 patent/US20170209596A1/en not_active Abandoned
-
2017
- 2017-10-25 US US15/793,501 patent/US20180271999A1/en not_active Abandoned
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- 2019-03-27 US US16/366,408 patent/US20200054766A1/en not_active Abandoned
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006080591A1 (en) * | 2005-01-26 | 2006-08-03 | Chong Kun Dang Pharmaceutical Corp. | Fumagillol derivatives or method for preparation of fumagillol derivatives, and pharmaceutical compositions comprising the same |
KR100676057B1 (ko) * | 2005-10-19 | 2007-01-30 | 엘지전자 주식회사 | 무선간섭에 따른 자동으로 채널변경이 가능한 무선랜 기기및 그 방법 |
KR100789379B1 (ko) * | 2005-11-25 | 2007-12-28 | 한국전자통신연구원 | 멀티캐스트 트래픽 조정 기능을 가지는 홈게이트웨이 장치및 그 방법 |
Also Published As
Publication number | Publication date |
---|---|
US20180271999A1 (en) | 2018-09-27 |
US20130029936A1 (en) | 2013-01-31 |
JP2005523305A (ja) | 2005-08-04 |
WO2003082845A1 (en) | 2003-10-09 |
AU2002246411A1 (en) | 2003-10-13 |
US20150238634A1 (en) | 2015-08-27 |
US20200054766A1 (en) | 2020-02-20 |
JP4202273B2 (ja) | 2008-12-24 |
US20050037994A1 (en) | 2005-02-17 |
KR100451485B1 (ko) | 2004-10-06 |
US20140155348A1 (en) | 2014-06-05 |
US20080085929A1 (en) | 2008-04-10 |
US20110034550A1 (en) | 2011-02-10 |
US20170209596A1 (en) | 2017-07-27 |
US7718695B2 (en) | 2010-05-18 |
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