JP4588087B2 - （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 - Google Patents
（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 Download PDFInfo
- Publication number
- JP4588087B2 JP4588087B2 JP2008308764A JP2008308764A JP4588087B2 JP 4588087 B2 JP4588087 B2 JP 4588087B2 JP 2008308764 A JP2008308764 A JP 2008308764A JP 2008308764 A JP2008308764 A JP 2008308764A JP 4588087 B2 JP4588087 B2 JP 4588087B2
- Authority
- JP
- Japan
- Prior art keywords
- map
- crystal
- solution
- cooling
- crystal form
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- YLXDRUQODCBMGR-BWGZFRQBSA-N (4R,5R,6S)-3-diphenylphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-4-[(4-nitrophenyl)methyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C[C@H]([C@@H]1[C@@H]2[C@@](C(=C(N2C1=O)C(=O)O)OP(=O)(C3=CC=CC=C3)C4=CC=CC=C4)(C)CC5=CC=C(C=C5)[N+](=O)[O-])O YLXDRUQODCBMGR-BWGZFRQBSA-N 0.000 title claims 2
- 239000013078 crystal Substances 0.000 claims description 96
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 48
- 238000001816 cooling Methods 0.000 claims description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 238000003756 stirring Methods 0.000 claims description 25
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- -1 diphenylphosphoryloxy Chemical group 0.000 claims description 5
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 206010013647 Drowning Diseases 0.000 description 2
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000002528 anti-freeze Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 101150116596 dhp-1 gene Proteins 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229960002182 imipenem Drugs 0.000 description 2
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Natural products CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 1
- HJXQYXPYIPAFNR-UHFFFAOYSA-N OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.Br Chemical compound OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.Br HJXQYXPYIPAFNR-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DHSUYTOATWAVLW-WFVMDLQDSA-N cilastatin Chemical compound CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C(O)=O)C(O)=O DHSUYTOATWAVLW-WFVMDLQDSA-N 0.000 description 1
- 229960004912 cilastatin Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- HXBZCHYDLURWIZ-UHFFFAOYSA-N diphenyl hydrogen phosphate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 HXBZCHYDLURWIZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009137959A JP2009137959A (ja) | 2009-06-25 |
| JP4588087B2 true JP4588087B2 (ja) | 2010-11-24 |
Family
ID=40868950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008308764A Expired - Fee Related 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 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP4588087B2 (ko) |
| KR (1) | KR100934785B1 (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103374037B (zh) * | 2012-04-12 | 2016-08-31 | 浙江九洲药业股份有限公司 | 碳青霉烯类化合物中间体的结晶纯化方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000044587A (ja) * | 1998-07-30 | 2000-02-15 | Kanegafuchi Chem Ind Co Ltd | カルバペネム抗生物質中間体の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP3479720B2 (ja) * | 1992-07-08 | 2003-12-15 | 武田薬品工業株式会社 | カルバペネム類の製造法 |
| 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 |
| 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 |
| US8093378B2 (en) * | 2006-04-28 | 2012-01-10 | Kaneka Corporation | Crystallization method for intermediates of carbapenem antibiotics |
-
2007
- 2007-12-03 KR KR1020070124602A patent/KR100934785B1/ko active IP Right Grant
-
2008
- 2008-12-03 JP JP2008308764A patent/JP4588087B2/ja not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000044587A (ja) * | 1998-07-30 | 2000-02-15 | Kanegafuchi Chem Ind Co Ltd | カルバペネム抗生物質中間体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20090057843A (ko) | 2009-06-08 |
| KR100934785B1 (ko) | 2009-12-31 |
| JP2009137959A (ja) | 2009-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2855022C (en) | 7-{(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidine-1-yl}-6-fluoro-1-(2-fluoroethyl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid crystal | |
| CA2956714A1 (en) | Coformer salts of (2s,3s)-methyl 7-fluoro-2-(4-fluorophenyl)-3-(1-methyl-1h-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate and methods of preparing them | |
| KR20100038081A (ko) | 비정질 리팍시민 제조방법 및 이에 의해 제조된 비정질 리팍시민 | |
| JP6321735B2 (ja) | エルタペネムナトリウムの結晶形およびその調製方法 | |
| EP1740593A1 (en) | Processes for the preparation of clopidogrel hydrogen sulfate polymorphic form i | |
| US20050137182A1 (en) | Novel crystalline form of cefdinir | |
| JP4588087B2 (ja) | （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 | |
| JP2005508334A (ja) | カルバペネム化合物の製造方法 | |
| WO2017202357A1 (zh) | 一种三氟甲基取代的吡喃衍生物的制备方法 | |
| JP5671204B2 (ja) | カルバペネム抗生物質中間体の改良された晶析方法 | |
| WO2002092605A1 (fr) | Cristal d'hydrate de compose de $g(b)-lactame | |
| EP2598485B1 (en) | Novel montelukast 4-halobenzylamine salt and method for preparing montelukast sodium salt by using the same | |
| JPS62164672A (ja) | １，２−ジメチルイミダゾ−ルの製造法 | |
| CA2928305A1 (en) | A crystalline anhydrous form of cabazitaxel, process for the preparation and pharmaceutical compositions thereof | |
| JPS62149679A (ja) | 新規な結晶構造を有するヒドロキシフエニルプロピオン酸エステル及びその製造法 | |
| CN108586450B (zh) | 一种胆碱m受体抗结剂的重结晶纯化方法 | |
| KR20110088755A (ko) | 이미페넴 중간체의 제조방법 | |
| JPS6289684A (ja) | ヒドロキシフエニルプロピオン酸エステルの製造法 | |
| KR101017944B1 (ko) | (1Ｒ, 5Ｒ, 6Ｓ)-ｐ-나이트로벤질-2-(다이페닐포스포릴옥시)-6-[(Ｒ)-1-하이드록시에틸]-1-메틸-카바페넴-3-카복실레이트(ＭＡＰ)결정형 Ⅱ의 제조방법 | |
| EP1637538B1 (en) | Crystalline carbapenem intermediate | |
| JP4655930B2 (ja) | キノリンカルボン酸誘導体溶媒和物の結晶 | |
| JP6975107B2 (ja) | ４−ハロシクロヘキサン−１−カルボン酸の精製方法、および、４−ハロシクロヘキサン−１−カルボン酸を含む生成物の製造方法 | |
| KR101256692B1 (ko) | 결정 형태의 １β-메틸카르바페넴 중간체 | |
| CN106083859B (zh) | 一种亚胺培南一水合物晶体的制备方法 | |
| KR20140084429A (ko) | 신규한 결정형의 리네졸리드 및 그 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20091117 |
|
| A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20091117 |
|
| A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20091225 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100112 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100405 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100511 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100723 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100817 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100907 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4588087 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130917 Year of fee payment: 3 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |