RU2650883C2 - Кристаллические формы макролида и их применение - Google Patents
Кристаллические формы макролида и их применение Download PDFInfo
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- RU2650883C2 RU2650883C2 RU2012144614A RU2012144614A RU2650883C2 RU 2650883 C2 RU2650883 C2 RU 2650883C2 RU 2012144614 A RU2012144614 A RU 2012144614A RU 2012144614 A RU2012144614 A RU 2012144614A RU 2650883 C2 RU2650883 C2 RU 2650883C2
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- 239000003120 macrolide antibiotic agent Substances 0.000 title description 5
- 229940041033 macrolides Drugs 0.000 title description 2
- IXXFZUPTQVDPPK-ZAWHAJPISA-N (1r,2r,4r,6r,7r,8r,10s,13r,14s)-17-[4-[4-(3-aminophenyl)triazol-1-yl]butyl]-7-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-10-fluoro-6-methoxy-2,4,6,8,10,14-hexamethyl-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tet Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@](C)(F)C(=O)O[C@@H]([C@]2(OC(=O)N(CCCCN3N=NC(=C3)C=3C=C(N)C=CC=3)[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O IXXFZUPTQVDPPK-ZAWHAJPISA-N 0.000 claims abstract description 182
- 239000000203 mixture Substances 0.000 claims abstract description 58
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229920003075 Plasdone™ K-29/32 polymer Polymers 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
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- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 241000270322 Lepidosauria Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
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- 229940088710 antibiotic agent Drugs 0.000 description 1
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- RFAZFSACZIVZDV-UHFFFAOYSA-N butan-2-one Chemical group CCC(C)=O.CCC(C)=O RFAZFSACZIVZDV-UHFFFAOYSA-N 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/04—Nitro compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31606310P | 2010-03-22 | 2010-03-22 | |
| US61/316,063 | 2010-03-22 | ||
| PCT/US2011/029424 WO2011119604A1 (en) | 2010-03-22 | 2011-03-22 | Crystalline forms of a macrolide, and uses therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012144614A RU2012144614A (ru) | 2014-04-27 |
| RU2650883C2 true RU2650883C2 (ru) | 2018-04-18 |
Family
ID=44673574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012144614A RU2650883C2 (ru) | 2010-03-22 | 2011-03-22 | Кристаллические формы макролида и их применение |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US8975386B2 (enExample) |
| EP (2) | EP3009442B1 (enExample) |
| JP (4) | JP5711352B2 (enExample) |
| KR (2) | KR20180101643A (enExample) |
| CN (2) | CN108570083A (enExample) |
| AU (2) | AU2011232627B2 (enExample) |
| BR (1) | BR112012023950A2 (enExample) |
| CA (1) | CA2793884C (enExample) |
| DK (1) | DK2550286T3 (enExample) |
| ES (1) | ES2564097T3 (enExample) |
| HR (1) | HRP20160168T1 (enExample) |
| IL (1) | IL222018B (enExample) |
| MX (1) | MX361413B (enExample) |
| MY (1) | MY162411A (enExample) |
| NZ (1) | NZ602544A (enExample) |
| PL (1) | PL2550286T3 (enExample) |
| RU (1) | RU2650883C2 (enExample) |
| SI (1) | SI2550286T1 (enExample) |
| WO (1) | WO2011119604A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7601695B2 (en) | 2003-03-10 | 2009-10-13 | Optimer Pharmaceuticals, Inc. | Antibacterial agents |
| EP2214484A4 (en) | 2007-10-25 | 2013-01-02 | Cempra Pharmaceuticals Inc | PROCESS FOR PREPARING ANTIBACTERIAL MAKROLIDE AGENTS |
| CN102245195B (zh) | 2008-10-24 | 2016-01-13 | 森普拉制药公司 | 使用含三唑的大环内酯的生物防御 |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| JP5914335B2 (ja) | 2009-09-10 | 2016-05-11 | センプラ ファーマシューティカルズ，インコーポレイテッド | マラリア、結核、及びｍａｃ病の治療方法 |
| EP3009442B1 (en) | 2010-03-22 | 2019-06-19 | Cempra Pharmaceuticals, Inc. | Crystalline forms of a macrolide, and uses therefor |
| CA2799937A1 (en) | 2010-05-20 | 2011-11-24 | Cempra Pharmaceuticals, Inc. | Processes for preparing macrolides and ketolides and intermediates therefor |
| WO2012034058A1 (en) | 2010-09-10 | 2012-03-15 | Cempra Pharmaceuticals, Inc. | Hydrogen bond forming fluoro ketolides for treating diseases |
| CA2868262A1 (en) | 2012-03-27 | 2013-10-03 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| HK1217665A1 (zh) | 2013-03-14 | 2017-01-20 | 森普拉制药公司 | 用於治療呼吸道疾病的方法及其製劑 |
| HK1218864A1 (zh) | 2013-03-15 | 2017-03-17 | 森普拉制药公司 | 用於制备大环内酯抗菌剂的收敛方法 |
| KR102363621B1 (ko) | 2013-04-04 | 2022-02-25 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 매크롤라이드 그리고 그의 제조방법 및 용도 |
| JP2017523975A (ja) * | 2014-08-05 | 2017-08-24 | センプラ ファーマシューティカルズ，インコーポレイテッド | 経口抗菌薬粉末懸濁製剤 |
| CN104151382B (zh) * | 2014-08-08 | 2016-09-14 | 广东东阳光药业有限公司 | 一种固态大环内酯的晶型 |
| CN104311611B (zh) * | 2014-08-13 | 2017-01-18 | 广东东阳光药业有限公司 | 一种制备固态大环内酯的方法 |
| CA2963815A1 (en) | 2014-10-08 | 2016-04-14 | President And Fellows Of Harvard College | 14-membered ketolides and methods of their preparation and use |
| WO2016154591A1 (en) | 2015-03-25 | 2016-09-29 | President And Fellows Of Harvard College | Macrolides with modified desosamine sugars and uses thereof |
| JP6112696B1 (ja) * | 2015-10-05 | 2017-04-12 | 富山化学工業株式会社 | ソリスロマイシンを含む錠剤 |
| EP3190122A1 (en) * | 2016-01-08 | 2017-07-12 | LEK Pharmaceuticals d.d. | A novel synthetic pathway towards solithromycin and purification thereof |
| TW201811811A (zh) * | 2016-09-02 | 2018-04-01 | 森普拉製藥公司 | 製備氟酮內酯之方法 |
| JP7693669B2 (ja) * | 2019-12-02 | 2025-06-17 | アリクァンタムアールエクス，インコーポレイテッド | 疾患の治療のためのセスロマイシンの塩及び多形体 セスロマイシンの塩及び多形体 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060100164A1 (en) * | 2003-03-10 | 2006-05-11 | Chang-Hsing Liang | Novel antibacterial agents |
| EA011281B1 (ru) * | 2004-12-21 | 2009-02-27 | Пфайзер Продактс Инк. | Макролиды |
| WO2009055557A1 (en) * | 2007-10-25 | 2009-04-30 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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