KR100885755B1 - 리팍시민의 신규의 다형체, 그의 제조방법, 및 그의의약품으로서의 용도 - Google Patents
리팍시민의 신규의 다형체, 그의 제조방법, 및 그의의약품으로서의 용도 Download PDFInfo
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- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
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Abstract
Description
Cmax ng/ml | Tmax h | AUC0-24 ng·h/ml | |
평균 | 평균 | 평균 | |
다형체 δ | 308.31 | 2 | 801 |
다형체 ε | 6.86 | 4 | 42 |
Cmax ng/ml | Tmax h | AUC0-24 ng·h/ml | |
평균 | 평균 | 평균 | |
다형체 δ | 308.31 | 2 | 801 |
다형체 ε | 6.86 | 4 | 42 |
Claims (12)
- 항균성 리팍시민의 다형체인 리팍시민 δ로서,2.5 % (w/w) 내지 6 % (w/w)의 수분 함량 및 5.7°±0.2, 6.7°±0.2, 7.1°±0.2, 8.0°±0.2, 8.7°±0.2, 10.4°±0.2, 10.8°±0.2, 11.3°±0.2, 12.1°±0.2, 17.0°±0.2, 17.3°±0.2, 17.5°±0.2, 18.5°±0.2, 18.8°±0.2, 19.1°±0.2, 21.0°±0.2, 21.5°±0.2의 회절각도 2θ 값에서 피크를 나타내는 분말 X-선 회절패턴(powder X-ray diffractogram)을 특징으로 하는 리팍시민 δ.
- 항균성 리팍시민의 다형체인 리팍시민 ε으로서,7.0°±0.2, 7.3°±0.2, 8.2°±0.2, 8.7°±0.2, 10.3°±0.2, 11.1°±0.2, 11.7°±0.2, 12.4°±0.2, 14.5°±0.2, 16.3°±0.2, 17.2°±0.2, 18.0°±0.2, 19.4°±0.2의 회절각도 2θ 값에서 피크를 나타내는 분말 X-선 회절패턴(powder X-ray diffractogram)을 특징으로 하는 리팍시민 ε.
- 1:1 내지 2:1의 부피비의 물 및 에틸 알콜의 용매 혼합물 중에서, 2 내지 8 시간 동안, 40℃ 내지 60℃의 온도에서, 1 몰당량의 리파마이신 O를 2-아미노-4-메틸피리딘과 반응시키는 단계;상기 반응 혼합물을 물, 에틸 알콜 및 진한 수성(aqueous) 염산의 혼합물 중의 아스코르빈산 용액으로 18℃ 내지 24℃에서 처리하고, 진한 염산 수용액으로 상기 반응 혼합물의 pH를 pH2.0으로 조절하고, 상기 현탁액을 여과하고, 얻어진 고체를 상기 반응에 사용된 동일한 물/에틸 알콜 혼합물로 세척하는 단계;얻어진 조 리팍시민(raw rifaximin)을 45℃ 내지 65℃의 온도에서 에틸 알콜에 용해시키고, 상기 용해를 위해 사용된 에틸 알콜의 중량에 대하여 15% 내지 70%에 해당하는 함량의 물을 가하여 침전을 유발시키고, 4 내지 36 시간 동안 교반하면서 상기 현탁액의 온도를 50℃ 내지 0℃로 낮추고, 상기 현탁액을 여과하고, 얻어진 고체를 물로 세척하고, 진공 또는 통상의 압력조건에서, 18℃ 내지 105℃의 온도에서, 2 내지 72 시간 동안, 상기 고체를 건조함으로써 상기 조 리팍시민을 정제하는 단계를 포함하는 리팍시민 δ 또는 ε의 제조방법.
- 제3항에 있어서, 조 리팍시민의 에탄올 용액에 물을 가한 후, 온도를 28℃ 내지 32℃로 낮추어 결정화를 유발시키는 단계; 얻어진 현탁액을 40℃ 내지 50℃의 온도에서 6 내지 24 시간 동안 교반한 다음, 15분 내지 1시간 동안 0℃로 냉각하고, 여과한 후, 얻어진 고체를 수분 함량이 2.5 % (w/w) 내지 6 % (w/w)가 될 때까지 건조하는 단계를 포함하는 리팍시민 δ의 제조방법.
- 제3항에 있어서, 진공 또는 대기압 하에서, 리팍시민 δ를 건조(단, 상기 건조는 ε 형태가 얻어지기에 충분한 시간 동안 지속시킨다)하는 단계를 포함하는 리팍시민 ε의 제조방법.
- 리팍시민 δ 및 약제학적으로 허용가능한 담체를 포함하는 항균활성을 갖는 경구용 의약 제제.
- 리팍시민 ε 및 약제학적으로 허용가능한 담체를 포함하는 항균활성을 갖는 경구용 의약 제제.
- 제6항 또는 제7항에 있어서, 상기 제제가 코팅정 및 비-코팅정, 경질 및 연질 젤라틴 캅셀, 당-코팅된 환제, 로젠지(lozenges), 웨이퍼 쉬트(wafer sheets), 펠렛 및 사시에(sachets) 중의 산제로부터 선택되는 것을 특징으로 하는 제제.
- 리팍시민 δ를 포함하는 항균활성을 갖는 국소용 의약 제제.
- 리팍시민 ε를 포함하는 항균활성을 갖는 국소용 의약 제제.
- 제9항 또는 제10항에 있어서, 상기 국소용 제제가 연고제, 포마드(pomades), 크림제, 겔제, 및 로오숀제로부터 선택되는 것을 특징으로 하는 제제.
- 제3항 또는 제5항에 있어서, 상기 건조는 건조제의 존재 하에서 수행하는 것을 특징으로 하는 방법.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP05004695.2A EP1698630B1 (en) | 2005-03-03 | 2005-03-03 | New polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal preparations |
EP05004695.2 | 2005-03-03 |
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KR20060096242A KR20060096242A (ko) | 2006-09-11 |
KR100885755B1 true KR100885755B1 (ko) | 2009-02-26 |
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US (9) | US8193196B2 (ko) |
EP (1) | EP1698630B1 (ko) |
JP (2) | JP5737825B2 (ko) |
KR (1) | KR100885755B1 (ko) |
CN (1) | CN1900077B (ko) |
AU (1) | AU2006222312B8 (ko) |
BR (1) | BRPI0608073A8 (ko) |
CA (1) | CA2594789C (ko) |
DK (1) | DK1698630T3 (ko) |
ES (1) | ES2522895T3 (ko) |
HK (1) | HK1096396A1 (ko) |
HR (1) | HRP20070433B1 (ko) |
IL (1) | IL184694A0 (ko) |
MA (1) | MA29345B1 (ko) |
MD (1) | MD4081G2 (ko) |
ME (1) | ME00272B (ko) |
MX (1) | MX2007010742A (ko) |
NO (1) | NO342197B1 (ko) |
NZ (1) | NZ556737A (ko) |
PL (1) | PL1698630T3 (ko) |
PT (1) | PT1698630E (ko) |
RS (1) | RS54570B1 (ko) |
RU (1) | RU2397985C2 (ko) |
SI (1) | SI1698630T1 (ko) |
TN (1) | TNSN07292A1 (ko) |
UA (1) | UA89809C2 (ko) |
WO (1) | WO2006094662A1 (ko) |
ZA (1) | ZA200707397B (ko) |
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KR20050043589A (ko) * | 2003-11-07 | 2005-05-11 | 알파 와셔만 에스. 피. 에이. | 리팍시민의 다형체, 그의 제조방법, 및 그의의약품으로서의 용도 |
WO2006094662A1 (en) | 2005-03-03 | 2006-09-14 | Alfa Wassermann S.P.A. | New polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal |
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