JP2008524306A5 - - Google Patents
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- Publication number
- JP2008524306A5 JP2008524306A5 JP2007547467A JP2007547467A JP2008524306A5 JP 2008524306 A5 JP2008524306 A5 JP 2008524306A5 JP 2007547467 A JP2007547467 A JP 2007547467A JP 2007547467 A JP2007547467 A JP 2007547467A JP 2008524306 A5 JP2008524306 A5 JP 2008524306A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- camptothecin
- ray diffraction
- butyloxyiminomethyl
- crystalline 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 17
- 238000000034 method Methods 0.000 claims 14
- 238000002441 X-ray diffraction Methods 0.000 claims 9
- 229940127093 camptothecin Drugs 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 150000001241 acetals Chemical class 0.000 claims 4
- 239000002244 precipitate Substances 0.000 claims 4
- XKIDBQHJMYSFPX-NRFANRHFSA-N 80758-83-4 Chemical compound C1=CC=C2C(C=O)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 XKIDBQHJMYSFPX-NRFANRHFSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
- 239000006184 cosolvent Substances 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000000707 stereoselective effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04030246 | 2004-12-21 | ||
| EP04030246.5 | 2004-12-21 | ||
| PCT/EP2005/056849 WO2006067092A2 (en) | 2004-12-21 | 2005-12-16 | Stereoselective process and crystalline forms of a camptothecin |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012247587A Division JP5982261B2 (ja) | 2004-12-21 | 2012-11-09 | 立体選択的方法およびカンプトテシンの結晶形態 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008524306A JP2008524306A (ja) | 2008-07-10 |
| JP2008524306A5 true JP2008524306A5 (enExample) | 2009-02-12 |
| JP5491699B2 JP5491699B2 (ja) | 2014-05-14 |
Family
ID=34927884
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007547467A Expired - Fee Related JP5491699B2 (ja) | 2004-12-21 | 2005-12-16 | 立体選択的方法およびカンプトテシンの結晶形態 |
| JP2012247587A Expired - Fee Related JP5982261B2 (ja) | 2004-12-21 | 2012-11-09 | 立体選択的方法およびカンプトテシンの結晶形態 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012247587A Expired - Fee Related JP5982261B2 (ja) | 2004-12-21 | 2012-11-09 | 立体選択的方法およびカンプトテシンの結晶形態 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US7799921B2 (enExample) |
| EP (1) | EP1828196B1 (enExample) |
| JP (2) | JP5491699B2 (enExample) |
| KR (1) | KR101355121B1 (enExample) |
| CN (1) | CN101084221B (enExample) |
| AU (1) | AU2005318227B2 (enExample) |
| BR (1) | BRPI0515832A (enExample) |
| CA (1) | CA2590756C (enExample) |
| CY (1) | CY1117243T1 (enExample) |
| DK (1) | DK1828196T3 (enExample) |
| ES (1) | ES2395930T3 (enExample) |
| HR (1) | HRP20120926T1 (enExample) |
| ME (1) | ME01495B (enExample) |
| PL (1) | PL1828196T3 (enExample) |
| PT (1) | PT1828196E (enExample) |
| RS (1) | RS52585B (enExample) |
| SI (1) | SI1828196T1 (enExample) |
| WO (1) | WO2006067092A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1828196B1 (en) * | 2004-12-21 | 2012-10-17 | SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A. | Stereoselective process and crystalline forms of a camptothecin |
| ITRM20050418A1 (it) * | 2005-08-04 | 2007-02-05 | Sigma Tau Ind Farmaceuti | Sistemi terapeutici a rilascio immediato per il migliorato assorbimento orale di 7-[(e)-t-butilossimminometil] camptotecina. |
| FR2938534B1 (fr) | 2008-11-14 | 2012-10-26 | Sanofi Aventis | Procede de preparation de l'hemifumarate d'eplivanserine |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03271278A (ja) * | 1990-03-16 | 1991-12-03 | Nissan Chem Ind Ltd | ２―アニリノピリミジン誘導体および農園芸用殺菌剤 |
| JP3046401B2 (ja) * | 1991-06-18 | 2000-05-29 | イハラケミカル工業株式会社 | ６−〔１−（ｎ−アルコキシイミノ）エチル〕サリチル酸誘導体及びその製造法 |
| IL106786A (en) * | 1992-09-10 | 1997-02-18 | Basf Ag | Substituted pyridine derivatives and fungicidal compositions containing them |
| EP1044977B1 (en) * | 1999-03-09 | 2002-05-02 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Camptothecin derivatives having antitumor activity |
| AU2003215594A1 (en) * | 2002-03-01 | 2003-09-16 | Pharmacia Italia S.P.A. | Crystalline polymorphic form of irinotecan hydrochloride |
| EP1828196B1 (en) * | 2004-12-21 | 2012-10-17 | SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A. | Stereoselective process and crystalline forms of a camptothecin |
-
2005
- 2005-12-16 EP EP05849781A patent/EP1828196B1/en not_active Expired - Lifetime
- 2005-12-16 HR HRP20120926TT patent/HRP20120926T1/hr unknown
- 2005-12-16 ME MEP-2012-128A patent/ME01495B/me unknown
- 2005-12-16 PT PT05849781T patent/PT1828196E/pt unknown
- 2005-12-16 DK DK05849781.9T patent/DK1828196T3/da active
- 2005-12-16 CA CA2590756A patent/CA2590756C/en not_active Expired - Fee Related
- 2005-12-16 ES ES05849781T patent/ES2395930T3/es not_active Expired - Lifetime
- 2005-12-16 KR KR1020077016814A patent/KR101355121B1/ko not_active Expired - Fee Related
- 2005-12-16 PL PL05849781T patent/PL1828196T3/pl unknown
- 2005-12-16 SI SI200531610T patent/SI1828196T1/sl unknown
- 2005-12-16 AU AU2005318227A patent/AU2005318227B2/en not_active Ceased
- 2005-12-16 CN CN2005800440829A patent/CN101084221B/zh not_active Expired - Lifetime
- 2005-12-16 WO PCT/EP2005/056849 patent/WO2006067092A2/en not_active Ceased
- 2005-12-16 RS RS20120505A patent/RS52585B/sr unknown
- 2005-12-16 US US11/721,282 patent/US7799921B2/en not_active Expired - Fee Related
- 2005-12-16 JP JP2007547467A patent/JP5491699B2/ja not_active Expired - Fee Related
- 2005-12-16 BR BRPI0515832-0A patent/BRPI0515832A/pt not_active Application Discontinuation
-
2010
- 2010-08-17 US US12/857,743 patent/US8124769B2/en not_active Expired - Fee Related
- 2010-08-17 US US12/857,776 patent/US8101758B2/en not_active Expired - Fee Related
-
2012
- 2012-10-30 CY CY20121101034T patent/CY1117243T1/el unknown
- 2012-11-09 JP JP2012247587A patent/JP5982261B2/ja not_active Expired - Fee Related
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