WO2004096815A1 - キノリンカルボン酸誘導体溶媒和物の結晶 - Google Patents
キノリンカルボン酸誘導体溶媒和物の結晶 Download PDFInfo
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- WO2004096815A1 WO2004096815A1 PCT/JP2004/006216 JP2004006216W WO2004096815A1 WO 2004096815 A1 WO2004096815 A1 WO 2004096815A1 JP 2004006216 W JP2004006216 W JP 2004006216W WO 2004096815 A1 WO2004096815 A1 WO 2004096815A1
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- WIPO (PCT)
- Prior art keywords
- methyl
- compound
- oxo
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- the present invention relates to 6-funoleolone 1-methylol 7- [4 one (5-methinol 1-2-oxo 1 1,3-di-skilled xsolen 1-4-inole) methyl-1-piperazinyl] 1 4-oxo 1 4 H- [1 , 3] thiazet [3, 2-a] quinoline 1-strength norlevonic acid
- Compound B A compound of Acetonitrile (hereinafter referred to as Compound B), a method for producing the compound B crystal, and III of Compound A using the compound B crystal.
- Compound B A compound of Acetonitrile (hereinafter referred to as Compound B), a method for producing the compound B crystal, and III of Compound A using the compound B crystal.
- the present invention relates to a method for producing a crystal.
- Compound A has excellent antibacterial activity (see, for example, Patent Document 1) and is marketed as a synthetic antibacterial agent.
- Compound A is known to have three types of crystal forms (type I, type II, type III), and the high melting point in differential scanning calorimetry (hereinafter referred to as DSC) measurement. It is defined as type I, type II, type III (for example, see Non-Patent Document 1).
- I II type I crystals are marketed (for example, see Non-Patent Document 1).
- type I, type II and type III crystals of compound A are obtained by crystallization from acetonitrile, but the crystallization conditions are unknown, and compound B Is not known (see Non-Patent Document 1, for example).
- Patent Document 1 Japanese Patent Laid-Open No. 1 2 9 4 6 80
- Non-patent document 1 Kazuro Kakemi, 7 others, “Creation of Prul loxacin, physicochemical properties and stability”, Pharmaceutical Research, 1 997, Vol. 28, No. 1, pi— 1 1 Disclosure of the Invention
- the present invention is mainly intended to provide a raw material for producing a type III crystal of compound A having excellent pharmacological activity and a method for producing the same.
- the present inventors were able to preferentially crystallize the compound B by controlling the supersaturation concentration in the course of crystallization using acetonitrile in a solvent.
- a type III crystal of Compound A could be produced, and the present invention was achieved.
- autonomous refers to a crystal nucleus that occurs naturally when crystallizing without using a seed crystal.
- C (g / 100 g) means the mass of Compound B dissolved in 100 g of solvent (solvate-free equivalent amount).
- C s (g / 100 g) is the saturated dissolution amount of compound B dissolved in 100 g of solvent under the ⁇ ! When the natural nucleus is generated or when seed crystals are added (solvate-free amount) Means.
- C ⁇ > 0 means ⁇ is in a supersaturated state
- the “solvate-free mass” refers to the mass of the compound B (molten metal) with respect to the solvent-free product.
- the compound B is 502.5 g.
- the equivalent amount of non-solvent is 461.5 g.
- desolvation means removal of a solvent in a solvate.
- the solvent is water: ⁇ can be cited as an example of forming a hydrate into an anhydride.
- FIG. 1 shows a powder X-ray diffraction spectrum chart of the I-type crystal of Compound A.
- the vertical axis represents intensity (c p s), and the horizontal axis represents diffraction angle (2 ⁇ ⁇ 0.2 degrees).
- Fig. 2 shows a powder X-ray diffraction spectrum chart of the I I crystal of the composite compound.
- the vertical axis represents intensity (c p s), and the horizontal axis represents diffraction angle (2 ⁇ ⁇ 0.2 degrees).
- FIG. 3 shows a powder X-ray diffraction spectrum chart of the crystals of the Aich compound.
- the vertical axis represents intensity (c p s), and the horizontal axis represents diffraction angle (26 ⁇ 0.2 degrees).
- FIG. 4 shows a powder X-ray diffraction spectrum chart of the II-I crystal of Compound A.
- the vertical axis represents intensity (c p s), and the horizontal axis represents diffraction angle (2 ⁇ soil 0.2 degree).
- the crystal of the compound B is crystallized from the acetonitrile solution of the compound A by setting the supersaturation concentration (g / 1 OOg) at the time of natural nucleus generation to 2.15 to 2.36. It can be produced while suppressing the formation of type I or II crystal of compound A.
- the crystals obtained depend on the crystal form of the seed crystal. Therefore, compared to crystal ⁇ ⁇ ⁇ by natural nucleation, crystallization with seed crystals produces crystals of compound B even if the supersaturation concentration (gZl OOg) is 0.41 to 2.36. be able to.
- the seed crystals are powerful (less than 0.004 g and less than 0.004 g Z solvent: 100 g).
- Z solvent i oog Z solvent i oog
- the amount of seed crystal s is low, the added seed crystal stimulates the production of new natural nuclei, and a large amount of ⁇ 1 is added!]
- the next crystal is prioritized and can suppress its own production and avoid the contamination of compound A type I or II crystals as much as possible.
- the temperature is 70 ° C or less, preferably 67 ° C or less.
- the temperature is preferably controlled to 55 ° C or lower.
- solvent-mediated transition means that a crystal is transformed into another crystal form in solution, for example, under a predetermined condition, the crystal force of compound B in a solvent. A transition to A type I crystal.
- I II type I crystals of compound A can be produced by desolvating the crystals of compound B. Desolvation can be carried out as usual by drying the crystals of the melt, but it is preferable to perform it at a temperature below 80 ° C. In addition, as described above, since the III crystal of Compound A causes a solvent-mediated transition, the drying temperature is 70 ° C or lower, preferably 67 ° C or lower, more preferably 55 ° C or lower. Control.
- the crystals of compound B can be produced, for example, as follows. (1) Dissolution process
- Compound A is dissolved in acetonitrile.
- the amount of Compound A and acetonitrile to be used is set so as to achieve a predetermined supersaturation concentration. It is preferable to perform the dissolution by heating. Caro heat is not particularly important, but it is preferable to perform it near the boiling point of acetonitrile. In addition, it is preferable to perform this process under an inert gas stream such as nitrogen or argon.
- the solution may be filtered to remove insolubles. Prevent crystal precipitation during filtration For this reason, it is preferable to use a filter with a pressure sensor under pressure. In order to observe the crystallization output S in the filtrate, it can be re-dissolved by reheating after filtration.
- the solution is cooled to precipitate crystals. Since it is necessary to control the 3 ⁇ 4i at which crystals begin to precipitate, caution must be exercised with respect to the age at which the crystals are formed without holding the seed crystals.
- the cooling after crystallization is not particularly limited, but is preferably about 0.04 ° CZ min or more, and more preferably about 0.22 ° C / min or more.
- the cooling separation (Si when collecting precipitated crystals) is not particularly critical, but is preferably 0 to 45 ° C, more preferably 0 to 25 ° C.
- the holding time after reaching the cooling temperature is not particularly limited, but is preferably 30 minutes or more, more preferably 90 minutes or more. Moreover, it is preferable to perform this process under a stream of inert gas such as nitrogen or argon.
- Precipitated crystals can be collected and dried by known means such as filtration or centrifugation.
- the precipitated crystals can be dried by a conventional method.
- the temperature during drying is set to 70 ° C or lower, preferably 67 ° C or lower, more preferably 55 ° C or lower.
- the crystals are prone to desolvation, and the formation of desolubilized pseudolites is also confirmed: ⁇ .
- I II type I crystals of compound A can be produced by desolvating the crystals of compound B by a conventional method. Drying is particularly important as long as the solvent can be removed from the solvate crystals, but drying at 80 ° C or lower is preferred. In order to prevent solvent-mediated transition, Si during drying is dried at 70 ° C. or lower, more preferably 67 ° C. or lower, more preferably 55 ° C. or lower for several hours to several tens of hours.
- thermal analysis (DSC measurement, TG measurement) is made by Shimadzu Corporation. Measurement of powder X-ray diffraction using DSC-50, a thermogravimetric differential calorimeter made by Sakusho, thermogravimetric measuring device TGA-50, thermal analysis system TA-50, at a temperature rise of 10 ° C / min. This was performed with a powder X-ray diffractometer manufactured by Rigaku Denki. The difference of the device is ⁇ 0.2 degrees.
- Non-Patent Document 1 melting is determined in descending order by DSC measurement as I type, I I type, and I I I type.
- the crystal obtained in this Reference Example corresponded to 1 crystal of Compound A.
- Fig. 1 shows the powder X-ray diffraction spectrum data of the crystals obtained.
- the I-type crystal of Compound A shows unique peaks at 12.5 degrees, 15 degrees, 18.0 degrees, and 24.0 degrees.
- Reference example 2
- Fig. 2 shows the powder X-ray diffraction spectrum data of the crystals obtained.
- the I-type crystal of Compound A shows unique peaks at 9.9 degrees, 18.0 degrees, 20.3 degrees, and 24.6 degrees.
- Example 1
- Fig. 3 shows the powder X-ray diffraction spectrum data of the crystals obtained.
- the crystals of Compound B are characteristic peaks at 7.3 degrees, 12.6 degrees, 14.7 degrees, 16.5 degrees, 19.2 degrees, 22.3 degrees, and 25.8 degrees. Indicates. In particular, the peaks at 7.3 degrees, 14.7 degrees, 19.2 degrees, and 22.3 degrees are characteristic.
- Example 2
- 6-Funoleol 1-methinole 7 _ [4— (5-Methyl-2-oxo-1, 1,3-dioxolen-4-inole) methyl-1-piperazinyl] -4-oxoxo 4 H— [1, 3] Thiazet [3, 2-a] quinoline 3-crystalline rubonic acid 'acetonitrile solvate (compound B)
- I represents the I crystal of Compound A
- II represents the Type II crystal of Compound A
- III represents the Type III crystal of Compound A
- B represents the crystal of Compound B.
- ⁇ is compound B even if the supersaturation concentration (gZ 1 0 0 0 g) at the time of inoculation is 0.4 1 to 2.1 2 Crystal was obtained. This is thought to be due to the preferential crystallization of the compound B crystals by suppressing the production of other crystal nuclei (type I crystals of compound A) by covering the seed crystal.
- Test example 2 Dehi compound B crystals
- the crystals of Compound B were desolvated by ffidrying at 80 for 24 hours, and the obtained crystals were measured with a powder X-ray diffractometer. As a result, the physical property values of the obtained crystal coincided with the spectrum of the crystal obtained in Example 3. Therefore, it can be seen that by desolvating the crystals of compound B, II-I crystals of compound A can be obtained.
- ⁇ indicates that the solvent has a boiling point of 13 ° C or higher, and that the compound A dissolves at 130 ° C, while the boiling point of the solvent is 130 ° C or lower. Indicates that compound A dissolves at its boiling point (solvent considered to be suitable as a crystallization solvent), ⁇ indicates that compound A dissolves at room temperature (possible solvent for crystallization), and X Is a solvent with a boiling point of 130 ° C or higher: ⁇ does not dissolve compound A at 130 ° C. Indicates that it does not dissolve (solvent inappropriate as crystallization solvent). Also, in the column * 2 in Table 2, ⁇ indicates that there was no peak other than Compound A ( ⁇ no premature), and X indicates that there was a peak other than Compound A ( ⁇ is present). One indicates untested.
- the possible solvents that can be used for the crystallization of Compound B are pyridine, nitromethane, chloroacetonitrile, N, N-dimethylformamide, Seven types of formic acid, acetic acid and aniline.
- the compound A of the compound A was observed, so the above three solvents are unsuitable as crystallization solvents.
- the crystals of compound B according to the present invention are important intermediates for producing II 1 crystals of compound A.
- I I I type crystals of compound A can be preferentially produced.
- the strength and the production method provide a high-quality pharmaceutical bulk powder (compound A III crystal). An excellent way to do that. '
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES04730102T ES2388921T3 (es) | 2003-04-30 | 2004-04-28 | Cristales de solvato derivado de ácido quinolincarboxílico |
PL04730102T PL1626051T3 (pl) | 2003-04-30 | 2004-04-28 | Kryształy solwatu pochodnej kwasu chinolinokarboksylowego |
US10/555,039 US7612205B2 (en) | 2003-04-30 | 2004-04-28 | Crystals of quinolinecarboxylic acid derivative solvate |
EP04730102A EP1626051B1 (en) | 2003-04-30 | 2004-04-28 | Crystals of quinolinecarboxylic acid derivative solvate |
BRPI0409930-3A BRPI0409930A (pt) | 2003-04-30 | 2004-04-28 | cristais de solvato derivado do ácido quinolinacarboxìlico |
KR1020057020448A KR101088988B1 (ko) | 2003-04-30 | 2004-04-28 | 퀴놀린카르복실산 유도체 용매화물의 결정 |
CA2523854A CA2523854C (en) | 2003-04-30 | 2004-04-28 | Crystals of quinolinecarboxylic acid derivative solvate |
AU2004234287A AU2004234287A1 (en) | 2003-04-30 | 2004-04-28 | Crystals of quinolinecarboxylic acid derivative solvate |
MXPA05011525A MXPA05011525A (es) | 2003-04-30 | 2004-04-28 | Cristales de solvato de derivado de acido quinolincarboxilico. |
JP2005505937A JP4655930B2 (ja) | 2003-04-30 | 2004-04-28 | キノリンカルボン酸誘導体溶媒和物の結晶 |
AU2010201309A AU2010201309B2 (en) | 2003-04-30 | 2010-04-01 | Crystals of quinolinecarboxylic acid derivative solvate |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003-124643 | 2003-04-30 | ||
JP2003124643 | 2003-04-30 | ||
JP2004006057 | 2004-01-13 | ||
JP2004-006057 | 2004-01-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004096815A1 true WO2004096815A1 (ja) | 2004-11-11 |
Family
ID=33422075
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/006216 WO2004096815A1 (ja) | 2003-04-30 | 2004-04-28 | キノリンカルボン酸誘導体溶媒和物の結晶 |
Country Status (13)
Country | Link |
---|---|
US (1) | US7612205B2 (ja) |
EP (2) | EP1626051B1 (ja) |
JP (1) | JP4655930B2 (ja) |
KR (1) | KR101088988B1 (ja) |
AU (2) | AU2004234287A1 (ja) |
BR (1) | BRPI0409930A (ja) |
CA (1) | CA2523854C (ja) |
ES (1) | ES2388921T3 (ja) |
MX (1) | MXPA05011525A (ja) |
PL (1) | PL1626051T3 (ja) |
PT (1) | PT1626051E (ja) |
RU (1) | RU2335503C2 (ja) |
WO (1) | WO2004096815A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012001357A1 (en) | 2010-06-30 | 2012-01-05 | Cipla Limited | Crystalline form of prulifloxacin and processes for its preparation |
RU2484768C1 (ru) * | 2012-02-07 | 2013-06-20 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Воронежская государственная медицинская академия им. Н.Н. Бурденко" Министерства здравоохранения и социального развития Российской Федерации | Способ прогнозирования течения глаукомной оптической нейропатии |
EP3773579A4 (en) | 2018-03-26 | 2022-03-09 | Clear Creek Bio, Inc. | COMPOSITIONS AND METHODS FOR INHIBITING DIHYDROOROTATE DEHYDROGENASE |
JP2023518419A (ja) * | 2020-03-20 | 2023-05-01 | クリア クリーク バイオ, インコーポレイテッド | ブレキナルナトリウムの安定した多形性組成物ならびにその使用および製造方法 |
US20210300873A1 (en) | 2020-03-20 | 2021-09-30 | Clear Creek Bio, Inc. | Stable polymorphic compositions of brequinar sodium and methods of use and manufacture thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01294680A (ja) * | 1987-11-07 | 1989-11-28 | Nippon Shinyaku Co Ltd | キノリンカルボン酸誘導体 |
-
2004
- 2004-04-28 CA CA2523854A patent/CA2523854C/en not_active Expired - Lifetime
- 2004-04-28 BR BRPI0409930-3A patent/BRPI0409930A/pt not_active Application Discontinuation
- 2004-04-28 US US10/555,039 patent/US7612205B2/en not_active Expired - Lifetime
- 2004-04-28 WO PCT/JP2004/006216 patent/WO2004096815A1/ja active Application Filing
- 2004-04-28 ES ES04730102T patent/ES2388921T3/es not_active Expired - Lifetime
- 2004-04-28 EP EP04730102A patent/EP1626051B1/en not_active Expired - Lifetime
- 2004-04-28 EP EP11161811A patent/EP2354144A1/en not_active Withdrawn
- 2004-04-28 PT PT04730102T patent/PT1626051E/pt unknown
- 2004-04-28 RU RU2005137156/04A patent/RU2335503C2/ru active
- 2004-04-28 PL PL04730102T patent/PL1626051T3/pl unknown
- 2004-04-28 MX MXPA05011525A patent/MXPA05011525A/es active IP Right Grant
- 2004-04-28 KR KR1020057020448A patent/KR101088988B1/ko active IP Right Grant
- 2004-04-28 JP JP2005505937A patent/JP4655930B2/ja not_active Expired - Lifetime
- 2004-04-28 AU AU2004234287A patent/AU2004234287A1/en not_active Abandoned
-
2010
- 2010-04-01 AU AU2010201309A patent/AU2010201309B2/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01294680A (ja) * | 1987-11-07 | 1989-11-28 | Nippon Shinyaku Co Ltd | キノリンカルボン酸誘導体 |
Non-Patent Citations (2)
Title |
---|
KAKEMI K. ET AL.: "Chemical structure, Physico-chemical Properties and Stability of Prulifloxacin", IYAKUHIN KENKYU, vol. 28, no. 1, 20 January 1997 (1997-01-20), pages 1 - 11, XP002987035 * |
See also references of EP1626051A4 * |
Also Published As
Publication number | Publication date |
---|---|
AU2010201309B2 (en) | 2011-10-13 |
BRPI0409930A (pt) | 2006-04-25 |
RU2335503C2 (ru) | 2008-10-10 |
MXPA05011525A (es) | 2005-12-12 |
US7612205B2 (en) | 2009-11-03 |
CA2523854C (en) | 2012-10-16 |
EP2354144A1 (en) | 2011-08-10 |
RU2005137156A (ru) | 2006-06-10 |
AU2004234287A1 (en) | 2004-11-11 |
PT1626051E (pt) | 2012-08-01 |
US20070149540A1 (en) | 2007-06-28 |
KR20060008930A (ko) | 2006-01-27 |
JPWO2004096815A1 (ja) | 2006-07-13 |
AU2010201309A1 (en) | 2010-04-22 |
ES2388921T3 (es) | 2012-10-19 |
EP1626051A1 (en) | 2006-02-15 |
JP4655930B2 (ja) | 2011-03-23 |
PL1626051T3 (pl) | 2012-10-31 |
EP1626051B1 (en) | 2012-06-13 |
KR101088988B1 (ko) | 2011-12-01 |
CA2523854A1 (en) | 2004-11-11 |
EP1626051A4 (en) | 2008-06-25 |
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