KR100934785B1 - (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트의신규한 결정형 및 그의 제조방법 - Google Patents
(1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트의신규한 결정형 및 그의 제조방법 Download PDFInfo
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- 238000009448 modified atmosphere packaging Methods 0.000 description 57
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
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- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
Claims (17)
- X-선 분말회절분석에서 5.680, 6.980, 10.240, 10.620, 11.160, 15.020, 15.500, 16.720, 20.200, 20.720, 21.260, 22.200, 22.660, 25.060, 25.640, 26.020, 26.380, 28.000, 29.980, 31.060, 35.400, 36.800, 39.420, 45.260, 45.800 및 49.040의 2θ 회절각을 갖는, (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트(MAP)의 결정형 II.
- 결정형 I의 (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트(MAP)를 에틸아세테이트, 아세톤 또는 이소프로필알콜에 용해시킨 후, 이 용액을 0.1 내지 30K/분의 속도로 냉각시키는 것을 포함하는, 제 1 항의 MAP의 결정형 II의 제조방법.
- 제 2 항에 있어서,상기 에틸아세테이트, 아세톤 또는 이소프로필알콜을 MAP의 2 내지 12배 중량의 양으로 사용하는 것을 특징으로 하는, MAP의 결정형 II의 제조방법.
- 제 2 항에 있어서,상기 MAP를 에틸아세테이트에 용해시키고, 이때 MAP의 용해를 65 내지 75℃에서, 용액의 냉각을 5 내지 35℃에서 수행하고, 용액의 냉각시 용액을 250 내지 350rpm 의 속도로 교반하는 것을 특징으로 하는, MAP의 결정형 II의 제조방법.
- 제 2 항에 있어서,상기 MAP를 아세톤에 용해시키고, 이때 MAP의 용해를 30 내지 45℃에서, 용액의 냉각을 0 내지 -30℃에서 수행하고 용액의 냉각시 용액을 400 내지 500rpm의 속도로 교반하는 것을 특징으로 하는, MAP의 결정형 II의 제조방법.
- 제 2 항에 있어서,상기 MAP를 이소프로필알콜에 용해시킨 후 용액의 냉각에 앞서 용액에 용액의 0.3 내지 1배 중량의 물을 추가로 첨가하는 것을 특징으로 하는, MAP의 결정형 II의 제조방법.
- 제 6 항에 있어서,상기 MAP의 용해를 70 내지 80℃에서, 용액의 냉각을 -10 내지 10℃에서 수행하고, 용액의 냉각시 용액을 교반하지 않는 것을 특징으로 하는, MAP의 결정형 II의 제조방법.
- X-선 분말회절분석에서 5.660, 6.920, 10.660, 13.800, 15.500, 16.660, 20.700, 21.240, 25.060, 26.020, 27.560, 29.920, 31.080, 32.000, 36.820, 37.680 및 41.120의 2θ 회절각을 갖는, (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6- [(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트(MAP)의 결정형 III.
- 결정형 I의 (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트(MAP)를 메틸에틸케톤 또는 메틸아테세이트에 용해시킨 후, 이 용액을 0.1 내지 15K/분의 속도로 냉각시키는 것을 포함하는, 제 8 항의 MAP의 결정형 III의 제조방법.
- 제 9 항에 있어서,상기 메틸에틸케톤 또는 메틸아세테이트를 MAP의 3 내지 7배 중량의 양으로 사용하는 것을 특징으로 하는, MAP의 결정형 III의 제조방법.
- 제 9 항에 있어서,상기 MAP를 메틸에틸케톤에 용해시키고, 이때 MAP의 용해를 40 내지 55℃에서, 용액의 냉각을 0 내지 -30℃에서 수행하고, 용액의 냉각시 용액을 100 내지 300rpm으로 교반하는 것을 특징으로 하는, MAP의 결정형 III의 제조방법.
- 제 9 항에 있어서,상기 MAP를 메틸아세테이트에 용해시키고, 이때 MAP의 용해를 40 내지 55℃에서, 용액의 냉각을 0 내지 -30℃에서 수행하고, 용액의 냉각시 용액을 교반하지 않는 것을 특징으로 하는, MAP의 결정형 III의 제조방법.
- X-선 분말회절분석에서 3 내지 30의 범위 내에서 5.600, 6.860, 10.580, 13.280, 14.040, 15.480, 15.960, 16.640, 17.680, 17.960, 18.320, 20.840, 21.200, 21.820, 22.720, 24.960, 25.640, 26.300 및 30.000의 2θ 회절각을 갖는, (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트(MAP)의 무정형-함유 결정형.
- 제 13 항에 있어서,상기 결정형이 무정형을 75 내지 85%의 부피로 함유하는 것을 특징으로 하는, MAP의 무정형-함유 결정형.
- 결정형 I의 (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트(MAP)를 이소프로필알콜에 용해시킨 후, 이 용액과 사이클로헥산을 혼합하여 0.1 내지 15K/분의 속도로 냉각시키는 것을 포함하는, 제 13 항의 MAP의 무정형-함유 결정형의 제조방법.
- 제 15 항에 있어서,상기 MAP, 이소프로필알콜 및 사이클로헥산을 1:8~15:8~15의 중량비로 사용하는 것을 특징으로 하는, MAP의 무정형-함유 결정형의 제조방법.
- 제 15 항에 있어서,상기 MAP의 용해를 70 내지 80℃에서, 용액의 냉각을 0 내지 40℃에서 수행하고, 용액의 냉각시 용액을 100 내지 300rpm으로 교반하는 것을 특징으로 하는, MAP의 무정형-함유 결정형의 제조방법.
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KR1020070124602A KR100934785B1 (ko) | 2007-12-03 | 2007-12-03 | (1R,5R,6S)-p-니트로벤질-2-(디페닐포스포릴옥시)-6-[(R)-1-히드록시에틸]-1-메틸-카바페넴-3-카복실레이트의신규한 결정형 및 그의 제조방법 |
JP2008308764A JP4588087B2 (ja) | 2007-12-03 | 2008-12-03 | (1R,5R,6S)−p−ニトロベンジル−2−(ジフェニルホスホリルオキシ)−6−[(R)−1−ヒドロキシエチル]−1−メチル−カルバペネム−3−カルボキシレートの新規な結晶形及びその製造方法 |
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US6346617B1 (en) * | 1997-08-26 | 2002-02-12 | Merck & Co., Inc. | Crystalline 2-hydroxymethyl carbapenem intermediate compounds and process for synthesis thereof |
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JP3834798B2 (ja) * | 1995-05-16 | 2006-10-18 | 日本曹達株式会社 | アゼチジノン化合物の製造方法 |
JP4028098B2 (ja) * | 1998-07-30 | 2007-12-26 | 株式会社カネカ | カルバペネム抗生物質中間体の製造方法 |
US8093378B2 (en) * | 2006-04-28 | 2012-01-10 | Kaneka Corporation | Crystallization method for intermediates of carbapenem antibiotics |
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JP3080417B2 (ja) * | 1991-02-28 | 2000-08-28 | 日本ワイスレダリー株式会社 | 結晶形態の1−メチル−2−ジフエニルホスホリルオキシ−カルバペネム化合物 |
US6346617B1 (en) * | 1997-08-26 | 2002-02-12 | Merck & Co., Inc. | Crystalline 2-hydroxymethyl carbapenem intermediate compounds and process for synthesis thereof |
JP3684339B2 (ja) * | 2001-07-10 | 2005-08-17 | ワイス株式会社 | カルバペネム化合物の製造方法 |
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