WO2003018615A1 - Nouveau cristal de compose lipopeptidique cyclique - Google Patents
Nouveau cristal de compose lipopeptidique cyclique Download PDFInfo
- Publication number
- WO2003018615A1 WO2003018615A1 PCT/JP2002/008694 JP0208694W WO03018615A1 WO 2003018615 A1 WO2003018615 A1 WO 2003018615A1 JP 0208694 W JP0208694 W JP 0208694W WO 03018615 A1 WO03018615 A1 WO 03018615A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- around
- acetone
- cyclic lipopeptide
- lipopeptide compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 82
- 239000013078 crystal Substances 0.000 title claims abstract description 49
- 108010028921 Lipopeptides Proteins 0.000 title claims abstract description 14
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims description 14
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 238000001816 cooling Methods 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000011549 crystallization solution Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 206010035660 Pneumocystis Infections Diseases 0.000 description 1
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 description 1
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Definitions
- This compound has antimicrobial activity (especially antifungal activity) and 8-1,3-glucan synthase inhibitory activity, and is effective in preventing Pneumocystis carinii infections, such as pneumocystis pneumonia. It is useful for prevention and treatment of various infectious diseases including. Background art
- the B82 type crystal of compound (I) obtained by the above production method is filtered and dried by a conventional method.
- the B82 type crystal of the compound (I) has extremely excellent advantages, and is very superior to the amorphous compound (I).
- Test sample 1 Amorphous compound (I) obtained in Example 25 in WO966Z11210
- FIG. 1 shows a powder X-ray diffraction pattern of the B82 type 2 crystal.
- FIG. 2 shows an infrared absorption spectrum (KBr method) of the B82 type crystal.
- Figure 1 shows the powder X-ray diffraction pattern.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pulmonology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001-263320 | 2001-08-31 | ||
| JP2001263320A JP2005053782A (ja) | 2001-08-31 | 2001-08-31 | 環状リポペプチド化合物の新規結晶 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2003018615A1 true WO2003018615A1 (fr) | 2003-03-06 |
Family
ID=19090093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2002/008694 WO2003018615A1 (fr) | 2001-08-31 | 2002-08-28 | Nouveau cristal de compose lipopeptidique cyclique |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2005053782A (fr) |
| AR (1) | AR036317A1 (fr) |
| WO (1) | WO2003018615A1 (fr) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8101712B2 (en) | 2006-10-16 | 2012-01-24 | TEVA Gyógyszergyár Zártkör{acute over ())}{acute over (})}úen M{acute over ())}{acute over (})}úköd{acute over ())}{acute over (})}ó Részvénytársaság | Purification processes for echinocandin-type compounds |
| WO2013143501A1 (fr) | 2012-03-30 | 2013-10-03 | 上海天伟生物制药有限公司 | Hydrate d'un composé cyclopeptidique, son procédé de préparation et son utilisation |
| WO2013143497A1 (fr) | 2012-03-30 | 2013-10-03 | 上海天伟生物制药有限公司 | Composé de cyclopeptide de grande pureté et procédé de préparation et utilisation associés |
| CN104788545A (zh) * | 2014-05-29 | 2015-07-22 | 上海天伟生物制药有限公司 | 一种环肽类化合物的结晶粉末及其制备方法和用途 |
| CN104861043A (zh) * | 2014-05-29 | 2015-08-26 | 上海天伟生物制药有限公司 | 一种环肽类化合物的组合物及其制备方法和用途 |
| CN104877012A (zh) * | 2014-05-29 | 2015-09-02 | 上海天伟生物制药有限公司 | 环肽类化合物的晶体及其制备方法和用途 |
| EP2832743A4 (fr) * | 2012-03-30 | 2015-09-23 | Shanghai Techwell Biopharm Co | Cristal de cyclopeptide de grande pureté et procédé de préparation et utilisation associés |
| EP3150623A4 (fr) * | 2014-05-29 | 2017-12-20 | Shanghai Techwell Biopharmaceutical Co., Ltd | Solvate d'un composé peptidique cyclique, son procédé de préparation et ses utilisations |
| CN108752430A (zh) * | 2018-05-31 | 2018-11-06 | 杭州中美华东制药有限公司 | 米卡芬净钠新晶型及其制备方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2583262C2 (ru) * | 2011-04-20 | 2016-05-10 | Кселлия Фармасьютикалз Апс | Способ очистки микафунгина |
| KR20250088544A (ko) * | 2022-10-20 | 2025-06-17 | 추가이 세이야쿠 가부시키가이샤 | 고리형 펩티드 결정을 제조하는 방법 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0511866A2 (fr) * | 1991-05-01 | 1992-11-04 | Merck & Co. Inc. | Procédé pour la cristalisation de lipopeptides cicliques |
| WO1996011210A1 (fr) * | 1994-10-07 | 1996-04-18 | Fujisawa Pharmaceutical Co., Ltd. | Hexapeptides cycliques a activite antibiotique |
| WO2000052037A1 (fr) * | 1999-03-03 | 2000-09-08 | Eli Lilly And Company | Complexes d'echinocandine/glucide |
-
2001
- 2001-08-31 JP JP2001263320A patent/JP2005053782A/ja not_active Withdrawn
-
2002
- 2002-08-28 WO PCT/JP2002/008694 patent/WO2003018615A1/fr active Application Filing
- 2002-08-29 AR ARP020103266A patent/AR036317A1/es not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0511866A2 (fr) * | 1991-05-01 | 1992-11-04 | Merck & Co. Inc. | Procédé pour la cristalisation de lipopeptides cicliques |
| WO1996011210A1 (fr) * | 1994-10-07 | 1996-04-18 | Fujisawa Pharmaceutical Co., Ltd. | Hexapeptides cycliques a activite antibiotique |
| WO2000052037A1 (fr) * | 1999-03-03 | 2000-09-08 | Eli Lilly And Company | Complexes d'echinocandine/glucide |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8101712B2 (en) | 2006-10-16 | 2012-01-24 | TEVA Gyógyszergyár Zártkör{acute over ())}{acute over (})}úen M{acute over ())}{acute over (})}úköd{acute over ())}{acute over (})}ó Részvénytársaság | Purification processes for echinocandin-type compounds |
| EP2832743A4 (fr) * | 2012-03-30 | 2015-09-23 | Shanghai Techwell Biopharm Co | Cristal de cyclopeptide de grande pureté et procédé de préparation et utilisation associés |
| WO2013143501A1 (fr) | 2012-03-30 | 2013-10-03 | 上海天伟生物制药有限公司 | Hydrate d'un composé cyclopeptidique, son procédé de préparation et son utilisation |
| WO2013143497A1 (fr) | 2012-03-30 | 2013-10-03 | 上海天伟生物制药有限公司 | Composé de cyclopeptide de grande pureté et procédé de préparation et utilisation associés |
| RU2607083C2 (ru) * | 2012-03-30 | 2017-01-10 | Шанхай Техвелл Биофармасьютикал Ко., Лтд | Кристалл циклопептида высокой чистоты, а также способ его получения и его применение |
| JP2017519042A (ja) * | 2014-05-29 | 2017-07-13 | シャンハイ テックウェル バイオファーマシューティカル カンパニー リミテッドShanghai Techwell Biopharmaceutical Co.,Ltd | シクロペプチド系化合物の組成物およびその製造方法と使用 |
| EP3150621A4 (fr) * | 2014-05-29 | 2017-12-27 | Shanghai Techwell Biopharmaceutical Co., Ltd | Composition de composé peptidique cyclique, son procédé de préparation et ses utilisations |
| WO2015180680A1 (fr) * | 2014-05-29 | 2015-12-03 | 上海天伟生物制药有限公司 | Poudre cristalline de composé peptidique cyclique, son procédé de préparation et ses utilisations |
| WO2015180678A1 (fr) * | 2014-05-29 | 2015-12-03 | 上海天伟生物制药有限公司 | Cristal de composé peptidique cyclique, son procédé de préparation et ses utilisations |
| JP2016538329A (ja) * | 2014-05-29 | 2016-12-08 | シャンハイ テックウェル バイオファーマシューティカル カンパニー リミテッドShanghai Techwell Biopharmaceutical Co.,Ltd | シクロペプチド系化合物の結晶およびその製造方法と使用 |
| JP2016538330A (ja) * | 2014-05-29 | 2016-12-08 | シャンハイ テックウェル バイオファーマシューティカル カンパニー リミテッドShanghai Techwell Biopharmaceutical Co.,Ltd | シクロペプチド系化合物の結晶粉末およびその製造方法と使用 |
| CN104861043A (zh) * | 2014-05-29 | 2015-08-26 | 上海天伟生物制药有限公司 | 一种环肽类化合物的组合物及其制备方法和用途 |
| CN104788545A (zh) * | 2014-05-29 | 2015-07-22 | 上海天伟生物制药有限公司 | 一种环肽类化合物的结晶粉末及其制备方法和用途 |
| EP3150623A4 (fr) * | 2014-05-29 | 2017-12-20 | Shanghai Techwell Biopharmaceutical Co., Ltd | Solvate d'un composé peptidique cyclique, son procédé de préparation et ses utilisations |
| CN104877012A (zh) * | 2014-05-29 | 2015-09-02 | 上海天伟生物制药有限公司 | 环肽类化合物的晶体及其制备方法和用途 |
| CN108276478A (zh) * | 2014-05-29 | 2018-07-13 | 上海天伟生物制药有限公司 | 环肽类化合物的晶体及其制备方法和用途 |
| JP7109189B2 (ja) | 2014-05-29 | 2022-07-29 | シャンハイ テックウェル バイオファーマシューティカル カンパニー リミテッド | シクロペプチド系化合物の組成物およびその製造方法と使用 |
| US10138274B2 (en) | 2014-05-29 | 2018-11-27 | Shanghai Techwell Biopharmaceutical Co., Ltd | Crystal of cyclic peptide compound, preparation method for same and uses thereof |
| US10138275B2 (en) | 2014-05-29 | 2018-11-27 | Shanghai Techwell Biopharmaceutical Co., Ltd. | Crystalline powder of cyclic peptide compound, preparation method for same, and uses thereof |
| CN104861043B (zh) * | 2014-05-29 | 2019-03-01 | 上海天伟生物制药有限公司 | 一种环肽类化合物的组合物及其制备方法和用途 |
| CN104877012B (zh) * | 2014-05-29 | 2019-03-01 | 上海天伟生物制药有限公司 | 环肽类化合物的晶体及其制备方法和用途 |
| CN108276478B (zh) * | 2014-05-29 | 2021-09-28 | 上海天伟生物制药有限公司 | 环肽类化合物的晶体及其制备方法和用途 |
| CN113087775A (zh) * | 2018-05-31 | 2021-07-09 | 杭州中美华东制药有限公司 | 米卡芬净钠新晶型ii及其制备方法 |
| CN113087775B (zh) * | 2018-05-31 | 2022-07-08 | 杭州中美华东制药有限公司 | 米卡芬净钠新晶型ii及其制备方法 |
| CN108752430A (zh) * | 2018-05-31 | 2018-11-06 | 杭州中美华东制药有限公司 | 米卡芬净钠新晶型及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AR036317A1 (es) | 2004-08-25 |
| JP2005053782A (ja) | 2005-03-03 |
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