KR20030028806A - 항염증제로서의 6.알파.,9.알파.-디플루오로-17.알파.-'(2-푸라닐카르복실)옥시-11.베타.-히드록시-16.알파.-메틸-3-옥소-안드로스트-1,4-디엔-17-카르보티오산 s-플루오로메틸 에스테르 - Google Patents
항염증제로서의 6.알파.,9.알파.-디플루오로-17.알파.-'(2-푸라닐카르복실)옥시-11.베타.-히드록시-16.알파.-메틸-3-옥소-안드로스트-1,4-디엔-17-카르보티오산 s-플루오로메틸 에스테르 Download PDFInfo
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Abstract
Description
트랜스액티베이션(GR)ED50(nM) | 트랜스리프레션(NFκB)ED50(nM) | |
화학식 (Ⅰ)의 화합물 | 0.06 | 0.20 |
대사물 | >250 | >1000 |
플루티카손 프로피오네이트 | 0.07 | 0.16 |
시험체 번호 | 세포 밀도(백만세포/mL) | 17-β산 대사물의 생성율(pmol/h) | |
화합물(Ⅰ) | 플루티카손 프로피오네이트 | ||
1 | 0.2 | 48.9 | 18.8 |
1 | 0.7 | 73.3 | 35.4 |
2 | 0.2 | 118 | 9.7 |
2 | 0.7 | 903 | 23.7 |
3 | 0.2 | 102 | 6.6 |
3 | 0.7 | 580 | 23.9 |
Cmax(pg/ml) | AUC(0-inf)(hr.pg/mL) | |||
돼지 1 | 돼지 2 | 돼지 1 | 돼지 2 | |
화학식(Ⅰ)의 화합물 | 117 | 81 | 254 | 221 |
플루티카손 프로피오네이트 | 277 | 218 | 455 | 495 |
형태 1 | 형태 3 | |
아세토니트릴 | +13.74 | +8.62 |
DMSO | +1.46 | -5.21 |
Claims (63)
- 하기 화학식 (Ⅰ)의 화합물 또는 이것의 용매화물:
- 제 1 항에 있어서, 비용매화된 형태임을 특징으로 하는 화학식 (Ⅰ)의 화합물.
- 제 2 항에 있어서, 형태 1의 다형체의 형태임을 특징으로 하는 비용매화된 형태의 화학식 (Ⅰ)의 화합물.
- 제 2 항에 있어서, 형태 2의 다형체의 형태임을 특징으로 하는 비용매화된 형태의 화학식 (Ⅰ)의 화합물.
- 제 2 항에 있어서, 형태 3의 다형체의 형태임을 특징으로 하는 비용매화된 형태의 화학식 (Ⅰ)의 화합물.
- 제 1 항에 있어서, 아세톤과의 본질적인 화학양론비의 용매화물의 형태로 결정 고형물로서 존재함을 특징으로 하는 화학식 (Ⅰ)의 화합물.
- 제 1 항에 있어서, 테트라히드로푸란과의 본질적인 화학양론비의 용매화물의 형태로 결정 고형물로서 존재함을 특징으로 하는 화학식 (Ⅰ)의 화합물.
- 제 1 항에 있어서, 이소프로판올과의 본질적인 화학양론비의 용매화물의 형태로 결정 고형물로서 존재함을 특징으로 하는 화학식 (Ⅰ)의 화합물.
- 제 1 항에 있어서, 메틸에틸케톤과의 본질적인 화학양론비의 용매화물의 형태로 결정 고형물로서 존재함을 특징으로 하는 화학식 (Ⅰ)의 화합물.
- 제 1 항에 있어서, 디메틸포름아미드와의 본질적인 화학양론비의 용매화물의 형태로 결정 고형물로서 존재함을 특징으로 하는 화학식 (Ⅰ)의 화합물.
- 제 1 항 내지 제 5 항중의 어느 한 항에 있어서, 가축 또는 사람 약물에 사용됨을 특징으로 하는 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물.
- 염증 및/또는 알레르기성 질환을 치료하기 위한 약제 제조에 사용되는, 제 1항 내지 제 5 항중의 어느 한 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물의 용도.
- 1종 이상의 생리학적으로 허용되는 희석제 또는 담체와 혼합된, 제 1 항 내지 제 5 항중의 어느 한 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물을 포함하는 약제 조성물.
- 제 13 항에 있어서, 비가압적으로, 건식 분말로서 구강을 통해 폐로 국부적으로 투여되기에 적합함을 특징으로 하는 약제 제형.
- 제 13 항 또는 제 14 항에 있어서, 희석제 또는 담체로서 락토오스 또는 전분을 함유함을 특징으로 하는 약제 제형.
- 제 13 항에 있어서, 비가압적이고, 비강으로 국부적으로 투여되기에 적합함을 특징으로 하는 약제 제형.
- 제 16 항에 있어서, 희석제 또는 담체로서 물을 함유함을 특징으로 하는 약제 제형.
- 계면활성제 및/또는 공용매와 선택적으로 혼합된, 추진제로서의 플루오로카본 또는 수소함유 클로로플루오로카본 및 제 1 항 내지 제 5 항중의 어느 한 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물을 포함하는, 에어로졸 약제 제형.
- 제 18 항에 있어서, 물 첨가제(즉, 초기 제형의 물 이외에 첨가되는 물)를 포함하는 특정 약제, 추진제 및 안정화제를 포함하지 않으며, 아미노산, 이것의 유도체 또는 이들의 혼합물을 포함하는 특정 약제, 추진제 및 안정화제를 포함하지 않음을 특징으로 하는 에어로졸 약제 제형.
- 제 18 항 또는 제 19 항에 있어서, 제 1 항 내지 제 3 항중의 어느 한 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물, 추진제로서의 플루오로카본 또는 수소함유 클로로플루오로카본, 및 추진제에 용해되는 현탁제를 포함함을 특징으로 하는 에어로졸 약제 제형.
- 제 20 항에 있어서, 현탁제가 올리고락트산 또는 이것의 유도체임을 특징으로 하는 에어로졸 약제 제형.
- 제 18 항 내지 제 21 항중의 어느 한 항에 있어서, 추진제가 1,1,1,2-테트라플루오로에탄, 1,1,1,2,3,3,3-헵타플루오로-n-프로판 및 이들의 혼합물로부터 선택됨을 특징으로 하는 에어로졸 약제 제형.
- 제 18 항 또는 제 19 항에 있어서, 기타 치료학적 활성제, 및 1,1,1,2-테트라플루오로에탄, 1,1,1,2,3,3,3-헵타플루오로-n-프로판 및 이들의 혼합물로부터 선택된 추진제와 선택적으로 혼합된, 제 1 항 내지 제 3 항중의 어느 한 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물을 필수 성분으로 함을 특징으로 하는 에어로졸 약제 제형.
- 제 13 항 내지 제 22 항중의 어느 한 항에 있어서, 기타 치료학적 활성제를 추가로 포함함을 특징으로 하는 약제 조성물.
- 제 24 항에 있어서, 기타 치료학적 활성제가 β2-아드레날린 수용체 작용제임을 특징으로 하는 약제 조성물.
- 제 1 항 내지 제 5 항중의 어느 한 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물, PDE4 억제제 및 생리학적으로 허용되는 희석제 또는 담체와의 혼합물을 포함하는 약제 조성물.
- 항염증 및/또는 알레르기성 질환을 앓는 사람 또는 동물을 치료하는 방법으로서, 상기 사람 또는 동물에 유효량의 제 1 항 내지 제 5 항중의 어느 한 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 생리학적으로 허용되는 용매화물을 투여하는 것을 포함하는 방법.
- 제 1 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 용매화물을 제조하는 방법으로서, 하기 화학식 (Ⅱ)의 화합물 또는 이것의 염을 알키화시키는 것을 포함하는 방법:
- 제 28 항에 있어서, 알킬화가 화학식 (Ⅱ)의 화합물 또는 이것의 염을 플루오로메틸 할라이드와 반응시킴으로써 수행됨을 특징으로 하는 방법.
- 제 3 항에 따른 비용매화된 형태 1의 다형체로서 화학식 (Ⅰ)의 화합물을 제조하는 방법으로서,(a) 비용매화 용매의 존재하에 화학식 (Ⅰ)의 화합물을 결정화시키거나;(b) 용매화된 형태의 화학식 (Ⅰ)의 화합물을 탈용매화시키는 것을 포함하는 방법.
- 제 3 항에 따른 비용매화된 형태 1의 다형체로서의 화학식 (Ⅰ)의 화합물을 제조하는 방법으로서, 화학식 (Ⅰ)의 화합물을 메틸이소부틸케톤, 에틸 아세테이트 또는 메틸 아세테이트중에 용해시키고, 비용매화 역용매를 첨가하므로써 비용매화된 형태 1로서의 화학식 (Ⅰ)의 화합물을 생성시키는 것을 포함하는 방법.
- 하기 화학식 (Ⅱ)의 화합물 또는 이것의 염:
- 제 32 항에 있어서, 고형의 결정 염의 형태로 존재함을 특징으로 하는 화학식 (Ⅱ)의 화합물.
- 제 33 항에 있어서, 디이소프로필에틸아민 염의 형태로 존재함을 특징으로 하는 화학식 (Ⅱ)의 화합물.
- 제 32 항에 따른 화학식 (Ⅱ)의 화합물을 제조하는 방법으로서,(a) 화학식 (Ⅲ)의 화합물 1몰당 2-푸로산의 활성화된 유도체 2몰 이상을 반응시켜 하기 화학식 (ⅡA)의 화합물을 생성시키고;(b) 단계 (a)의 생성물을 수용성 2-푸로일 아미드를 생성시킬 수 있는 1차 또는 2차 유기 아민 염기와 반응시켜 화학식 (ⅡA)의 화합물로부터 황-연결된 2-푸로일 부분을 제거하는 것을 포함하는 방법.
- 제 35 항에 있어서, 화학식 (Ⅱ)의 화합물을 제조하는 방법으로서,(c1) 단계 (b)의 생성물이 사실상 불수용성 유기 용매에 용해될 경우, 단계 (b)의 아미드 부산물을 수성 세척함으로써 화학식 (Ⅱ)의 화합물을 정화시키는 단계, 또는(c2) 단계 (b)의 생성물이 수용성 용매에 용해될 경우, 단계 (b)의 생성물을 수성 매질로 처리하여 순수한 화학식 (Ⅱ)의 화합물 또는 이것의 염을 침전시킴으로써 화학식 (Ⅱ)의 화합물을 정화시키는 단계를 추가로 포함함을 특징으로 하는 방법.
- 제 32 항에 따른 화학식 (Ⅱ)의 화합물을 제조하는 방법으로서,(a) 1몰의 화학식 (Ⅲ)의 화합물을 2-푸로산의 활성화된 유도체 2몰 이상과반응시켜 제 35 항에 따른 화학식 (ⅡA)의 화합물을 생성시키고;(b) 단계 (a)의 생성물을 추가 몰의 화학식 (Ⅲ)의 화합물과 반응시켜, 화학식 (ⅡA)의 화합물로부터 황-연결된 2-푸로일 부분을 제거하여 2몰의 화학식 (Ⅱ)의 화합물을 제공하는 것을 포함하는 방법.
- 하기 화학식 (ⅡA)의 화합물:
- 하기 화학식 (Ⅵ)의 화합물:
- 하기 화학식 (Ⅶ)의 화합물 또는 이것의 염:
- 하기 화학식 (Ⅷ)의 화합물:
- 하기 화학식 (Ⅸ)의 화합물:
- 하기 화학식 (ⅨA)의 화합물:상기 식에서, X는 할로겐이다.
- 하기 화학식 (ⅩⅡ)의 화합물 또는 이것의 염:
- 하기 화학식 (ⅩⅤ)의 화합물:상기 식에서, P는 히드록시 보호기이다.
- 하기 화학식 (ⅩⅥ)의 화합물:
- 하기 화학식 (ⅩⅦ)의 화합물 또는 이것의 염:상기 식에서, P는 히드록시 보호기이다.
- 11-카르보닐기가 마스킹된 하기 화학식 (ⅩⅩ)의 화합물 또는 이것의 염:
- 하기 화학식 (ⅩⅩⅢ)의 화합물:상기 식에서, L은 플루오르를 제외한 이탈기이다.
- 제 4 항에 따른 비용매화된 형태 2의 다형체로서의 화학식 (Ⅰ)의 화합물을 제조하는 방법으로서, 비용매화된 형태의 화학식 (Ⅰ)의 화합물을 메탄올 또는 무수 디클로로메탄중에 용해시키고, 비용매화된 형태 2의 다형체로서의 화학식 (Ⅰ)의 화합물을 재결정화시키는 것을 포함하는 방법.
- 제 5 항에 따른 비용매화된 형태 3의 다형체로서의 화학식 (Ⅰ)의 화합물을 제조하는 방법으로서, 물의 존재하에 화학식 (Ⅰ)의 화합물 또는 이것의 용매화물을 디클로로메탄중에 용해시키고, 비용매화된 형태 3의 다형체로서의 화학식 (Ⅰ)의 화합물을 재결정화시키는 것을 포함하는 방법.
- 제 1 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 염을 제조하는 방법으로서, 하기 화학식 (Ⅵ)의 화합물을 플루오르 공급원과 반응시키는 것을 포함하는 방법:
- 제 1 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 용매화물을 제조하는 방법으로서, 11-β-히드록시기가 보호되거나 마스킹된 화학식 (Ⅰ)의 화합물을 탈보호시키거나 비마스킹시키는 것을 포함하는 방법.
- 제 53 항에 있어서, 11-β-히드록시기가 보호된 경우, 하기 화학식 (ⅩⅤ)의 화합물을 탈보호시키는 것을 포함함을 특징으로 하는 방법:상기 식에서, P는 히드록시 보호기이다.
- 제 53 항에 있어서, 11-β-히드록시기를 마스킹된 경우, 11-카르보닐기가 마스킹된 하기 화학식 (ⅩⅥ)의 화합물 또는 이것의 유도체를 환원시키는 것을 포함함을 특징으로 하는 방법:
- 제 1 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 용매화물을 제조하는 방법으로서, 하기 화학식 (ⅩⅩⅢ)의 화합물을 플루오르 공급원과 반응시키는 것을 포함하는 방법:상기 식에서, L은 이탈기이다.
- 하기 화학식 (ⅩⅢ)의 화합물:
- 하기 화학식 (ⅩⅣ)의 화합물 또는 이것의 염:
- 11-카르보닐기가 마스킹된 하기 화학식 (ⅩⅩⅠ)의 화합물 또는 이것의 유도체:
- 11-카르보닐기가 마스킹된 하기 화학식 (ⅩⅩⅡ)의 화합물 또는 이것의 유도체:
- 하기 화학식 (Ⅹ)의 화합물:
- 제 1 항에 따른 화학식 (Ⅰ)의 화합물 또는 이것의 용매화물을 제조하는 방법으로서, 3-카르보닐기가 보호되거나 마스킹된 화학식 (Ⅰ)의 화합물의 유도체를 탈보호하거나 비마스킹시키는 것을 포함하는 방법.
- 제 30 항에 따른 화학식 (Ⅱ)의 화합물을 제조하는 방법으로서, 제 62 항에 따른 화학식(Ⅹ)의 화합물을, 카르복실산을 카르보티오산으로 전환시키기에 적합한 시약으로 처리하는 것을 포함하는 방법.
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PCT/GB2001/003495 WO2002012265A1 (en) | 2000-08-05 | 2001-08-03 | 6.ALPHA., 9.ALPHA.-DIFLUORO-17.ALPHA.-`(2-FURANYLCARBOXYL) OXY!-11.BETA.-HYDROXY-16.ALPHA.-METHYL-3-OXO-ANDROST-1,4,-DIENE-17-CARBOTHIOIC ACID S-FLUOROMETHYL ESTER AS AN ANTI-INFLAMMATORY AGENT |
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