PL195910B1 - Sposób wytwarzania 9-deokso-9a-aza-9a-metylo-9a-homoerytromycyny A w formie niekrystalicznej - Google Patents
Sposób wytwarzania 9-deokso-9a-aza-9a-metylo-9a-homoerytromycyny A w formie niekrystalicznejInfo
- Publication number
- PL195910B1 PL195910B1 PL344101A PL34410100A PL195910B1 PL 195910 B1 PL195910 B1 PL 195910B1 PL 344101 A PL344101 A PL 344101A PL 34410100 A PL34410100 A PL 34410100A PL 195910 B1 PL195910 B1 PL 195910B1
- Authority
- PL
- Poland
- Prior art keywords
- aza
- azithromycin
- methyl
- crystalline
- homoerythromycin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 150000004683 dihydrates Chemical class 0.000 title abstract description 13
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims abstract description 36
- 229960004099 azithromycin Drugs 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
- HQUPLSLYZHKKQT-WVVFQGGUSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-o Chemical compound O.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 HQUPLSLYZHKKQT-WVVFQGGUSA-N 0.000 claims description 8
- 229960003256 azithromycin monohydrate Drugs 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000002441 X-ray diffraction Methods 0.000 abstract description 5
- 239000003120 macrolide antibiotic agent Substances 0.000 abstract description 4
- 238000004566 IR spectroscopy Methods 0.000 abstract description 2
- 238000007707 calorimetry Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- VQEMDSRIOVZAOM-UHFFFAOYSA-N 4-(4-methylsulfonylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CSC(N)=N1 VQEMDSRIOVZAOM-UHFFFAOYSA-N 0.000 description 6
- 229960004924 azithromycin dihydrate Drugs 0.000 description 6
- 150000004682 monohydrates Chemical class 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000001907 polarising light microscopy Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HRKNNHYKWGYTEN-HOQMJRDDSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 HRKNNHYKWGYTEN-HOQMJRDDSA-N 0.000 description 1
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009902620A ES2177373B1 (es) | 1999-11-26 | 1999-11-26 | Preparacion de azitromicina en su forma no cristalina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL344101A1 PL344101A1 (en) | 2001-06-04 |
| PL195910B1 true PL195910B1 (pl) | 2007-11-30 |
Family
ID=8310747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL344101A PL195910B1 (pl) | 1999-11-26 | 2000-11-24 | Sposób wytwarzania 9-deokso-9a-aza-9a-metylo-9a-homoerytromycyny A w formie niekrystalicznej |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6451990B1 (https=) |
| EP (2) | EP1103558B1 (https=) |
| JP (2) | JP4260354B2 (https=) |
| AT (2) | ATE325805T1 (https=) |
| CA (1) | CA2326930C (https=) |
| DE (2) | DE60003509T2 (https=) |
| ES (2) | ES2177373B1 (https=) |
| PL (1) | PL195910B1 (https=) |
| TR (1) | TR200003474A3 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20020231A2 (en) * | 2002-03-18 | 2003-12-31 | Pliva D D | ISOSTRUCTURAL PSEUDOPOLYMORPHS OF 9-DEOXO-9a-AZA-9a-METHYL-9a-HOMOERYTHROMYCIN A |
| CA2245398C (en) | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| ES2162764B1 (es) * | 2000-05-17 | 2003-04-01 | Ercros Ind Sa | Forma polimorfica del dihidrato de azitromicina, y su procedimiento deobtencion. |
| HRP20030430B1 (hr) * | 2000-11-27 | 2011-11-30 | Biochemie S.A. | Makrolidni solvati |
| IN190080B (https=) * | 2001-01-29 | 2003-06-07 | Alembic Ltd | |
| KR100491183B1 (ko) * | 2001-03-21 | 2005-05-25 | 한미약품 주식회사 | 아지트로마이신의 제조방법 및 이 방법에 사용되는9-데옥소-9에이-아자-9에이-호모에리트로마이신 에이의결정성 수화물 |
| SI1390377T1 (sl) * | 2001-05-22 | 2006-06-30 | Pfizer Prod Inc | Nova kristalna oblika azitromicina |
| ES2258142T3 (es) | 2001-05-22 | 2006-08-16 | Pfizer Products Inc. | Nueva forma cristalina. |
| US6861413B2 (en) | 2001-05-22 | 2005-03-01 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| PL371259A1 (pl) | 2001-12-21 | 2005-06-13 | Pfizer Products Inc. | Bezpośrednio sprasowywalne preparaty azytromycyny |
| MXPA04007847A (es) | 2002-02-13 | 2005-02-24 | Biogal Gyogyszergyar | Metodo para extraer un macrolido de biomateria. |
| US7452692B2 (en) | 2002-02-13 | 2008-11-18 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Method for extracting a macrolide from biomatter |
| HRP20020614A2 (en) | 2002-07-22 | 2004-06-30 | PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. | Rhombic pseudopolymorph of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin a |
| WO2004089958A2 (en) * | 2003-03-31 | 2004-10-21 | TEVA Gyógyszergyár Részvénytársaság | Crystallization and purification of macrolides |
| PL1558622T3 (pl) | 2003-07-24 | 2008-06-30 | Teva Gyogyszergyar Zartkoerueen Muekoedoe Reszvenytarsasag | Sposób oczyszczania makrolidów |
| KR100844628B1 (ko) * | 2003-12-04 | 2008-07-07 | 화이자 프로덕츠 인크. | 제약상 다입자의 제조 방법 |
| US7384921B2 (en) * | 2004-02-20 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | Polymorphic forms of 6-11 bicyclic ketolide derivatives |
| US7468428B2 (en) | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| US20060116336A1 (en) * | 2004-03-17 | 2006-06-01 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
| WO2006115494A1 (en) * | 2005-04-26 | 2006-11-02 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
| US7683162B2 (en) | 2004-08-30 | 2010-03-23 | Taro Pharmaceutical Industries Limited | Process of preparing a crystalline azithromycin monohydrate |
| US7464012B2 (en) * | 2004-12-10 | 2008-12-09 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Simplified process simulator |
| US7582312B2 (en) * | 2004-11-15 | 2009-09-01 | Discovery Laboratories, Inc. | Methods to produce lung surfactant formulations via lyophilization and formulations and uses thereof |
| CA2584430A1 (en) | 2004-12-01 | 2006-06-08 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Methods for preparing pimecrolimus |
| JP2009501206A (ja) * | 2005-07-14 | 2009-01-15 | ファイザー・プロダクツ・インク | 非晶質アジスロマイシン粒子の生成方法 |
| WO2007067566A2 (en) * | 2005-12-07 | 2007-06-14 | Wyeth | Methods for preparing crystalline rapamycin and for measuring crystallinity of rapamycin compounds using differential scanning calorimetry |
| UA102128C2 (en) * | 2008-12-05 | 2013-06-10 | Х. Луннбек А/С | Nalmefene hydrochloride dihydrate |
| WO2011015219A1 (en) | 2009-08-06 | 2011-02-10 | Shifa Pharmed Industrial Group Co. | Process for the purification of azithromycin by separation from its thermal degradation products and/or isomers |
| CA2784494C (en) * | 2009-12-18 | 2019-03-12 | North-West University | Composition comprising an amorphous non-crystalline glass form of roxithromycin |
| WO2013088274A1 (en) * | 2011-12-14 | 2013-06-20 | Wockhardt Limited | Anhydrous amorphous azithromycin composition free of azithromycin dihydrate |
| CN106188177A (zh) * | 2016-07-12 | 2016-12-07 | 浙江亚太药业股份有限公司 | 一种阿奇霉素化合物的制备方法及其药物制剂 |
| CN108003109A (zh) * | 2017-12-18 | 2018-05-08 | 南开大学 | 一种大环内酯化合物的晶型及其制备方法与用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI8110592A8 (en) * | 1981-03-06 | 1996-06-30 | Pliva Pharm & Chem Works | Process for preparing of n-methyl-11-aza-10-deoxo-10-dihydroerythromycine a and derivatives thereof |
| US4474768A (en) | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| WO1989000576A1 (en) * | 1987-07-09 | 1989-01-26 | Pfizer Inc. | Azithromycin dihydrate |
| US5686587A (en) | 1993-05-19 | 1997-11-11 | Pfizer Inc. | Intermediate for azithromycin |
| ECSP951389A (es) | 1995-02-21 | 1996-05-10 | Un procedimiento de obtencion de hidrato de azitromicina | |
| ES2122905B1 (es) | 1996-07-11 | 1999-11-16 | Astur Pharma Sa | Sintesis de 11,12-hidrogenoortoborato de 9-desoxo-9a-aza-11,12-desoxi-9a-metil-9a-homoeritromicina a. un procedimiento para la preparacion de 9-desoxo-9a-aza-9a-metil-9a-homoeritromicina a dihidrato (azitromicina dihidrato). |
| PT102130A (pt) | 1998-03-13 | 1999-09-30 | Hovione Sociedade Quimica S A | Processo de preparacao de dihidrato de azitromicina |
| TW546302B (en) * | 1998-05-08 | 2003-08-11 | Biochemie Sa | Improvements in macrolide production |
| CA2245398C (en) * | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
-
1999
- 1999-11-26 ES ES009902620A patent/ES2177373B1/es not_active Expired - Fee Related
-
2000
- 2000-02-23 EP EP00500028A patent/EP1103558B1/en not_active Expired - Lifetime
- 2000-02-23 AT AT01204550T patent/ATE325805T1/de not_active IP Right Cessation
- 2000-02-23 EP EP01204550A patent/EP1234833B1/en not_active Expired - Lifetime
- 2000-02-23 AT AT00500028T patent/ATE243704T1/de not_active IP Right Cessation
- 2000-02-23 DE DE60003509T patent/DE60003509T2/de not_active Expired - Fee Related
- 2000-02-23 DE DE60027919T patent/DE60027919D1/de not_active Expired - Lifetime
- 2000-11-22 US US09/718,833 patent/US6451990B1/en not_active Expired - Fee Related
- 2000-11-23 TR TR2000/03474A patent/TR200003474A3/tr unknown
- 2000-11-24 PL PL344101A patent/PL195910B1/pl not_active IP Right Cessation
- 2000-11-24 CA CA002326930A patent/CA2326930C/en not_active Expired - Fee Related
- 2000-11-27 JP JP2000359948A patent/JP4260354B2/ja not_active Expired - Fee Related
-
2002
- 2002-10-09 ES ES200202318A patent/ES2207403B1/es not_active Expired - Fee Related
-
2008
- 2008-08-26 JP JP2008217072A patent/JP2009007376A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATE243704T1 (de) | 2003-07-15 |
| EP1103558A3 (en) | 2001-07-04 |
| EP1234833A3 (en) | 2003-03-12 |
| PL344101A1 (en) | 2001-06-04 |
| JP4260354B2 (ja) | 2009-04-30 |
| JP2009007376A (ja) | 2009-01-15 |
| DE60003509D1 (de) | 2003-07-31 |
| ATE325805T1 (de) | 2006-06-15 |
| EP1103558A2 (en) | 2001-05-30 |
| EP1234833B1 (en) | 2006-05-10 |
| ES2177373A1 (es) | 2002-12-01 |
| US6451990B1 (en) | 2002-09-17 |
| TR200003474A2 (tr) | 2001-07-23 |
| TR200003474A3 (tr) | 2001-07-23 |
| ES2207403B1 (es) | 2005-03-01 |
| EP1103558B1 (en) | 2003-06-25 |
| DE60027919D1 (de) | 2006-06-14 |
| JP2001187797A (ja) | 2001-07-10 |
| ES2177373B1 (es) | 2003-11-01 |
| DE60003509T2 (de) | 2004-04-15 |
| EP1234833A2 (en) | 2002-08-28 |
| ES2207403A1 (es) | 2004-05-16 |
| CA2326930A1 (en) | 2001-05-26 |
| CA2326930C (en) | 2005-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL195910B1 (pl) | Sposób wytwarzania 9-deokso-9a-aza-9a-metylo-9a-homoerytromycyny A w formie niekrystalicznej | |
| JP3101590B2 (ja) | アジトロマイシン・２水和物の製法及びその中間体 | |
| HU193886B (en) | Process for preparing epimer azahomoerythromycin a derivatives | |
| HU215158B (hu) | Eljárás egy azitromicin A O-benziloxi-karbonil-származék előállítására | |
| KR100600463B1 (ko) | 항균 활성을 갖는 15-원 락탐 케톨라이드 | |
| JP2001520234A (ja) | ９ａ−アザリド類から誘導される新規３，６−ヘミケタール類 | |
| JPS58109496A (ja) | マクロライド抗生物質の合成の化学的方法 | |
| CA2067274C (en) | Solvates of dirithromycin and a process for isolating form ii dirithromycin | |
| EP0503949A1 (en) | Novel process for the preparation of 9-deoxo-9(z)-hydroxyiminoerythromycin A | |
| JPS63107994A (ja) | エリスロマイシン誘導体 | |
| EP0503932A1 (en) | 9-Deoxo-9(z)-hydroxy-iminoerythromycin A and O-derivatives thereof | |
| CA1106366A (en) | Semi-synthetic 4"-amino-oleandomycin derivatives | |
| CA2485433C (en) | Preparation of non-crystalline and crystalline dihydrate forms of azithromycin | |
| KR100490074B1 (ko) | 신규한 에리트로마이신 유도체, 그의 제조 방법 및 의약품으로서의 그의 용도 | |
| Kurihara et al. | Cladinose analogues of sixteen-membered macrolide antibiotics I. Synthesis of 4-O-alkyl-l-cladinose analogues via glycosylation | |
| JP2001513101A (ja) | 新規のエリスロマイシン誘導体、その製造方法及びその薬剤としての使用 | |
| RU2234510C2 (ru) | Производные класса олеандомицина и способ их получения | |
| WO2018191682A1 (en) | Triazole compounds and methods of making and using the same | |
| JP4522496B2 (ja) | 新規なエリスロマイシン誘導体、製造方法及び医薬としての利用 | |
| JP3227871B2 (ja) | ６−ｏ−メチルエリスロマイシンａ誘導体 | |
| JP2003502338A (ja) | ４’−デミカロシル−８ａ−アザ−８ａ−ホモタイロシンの誘導体 | |
| EP0508795A1 (en) | 8a-aza-8a-homoerythromycin cyclic iminoethers | |
| JP2006507315A (ja) | ９−デオキソ−９−ジヒドロ−９ａ−アザ−９ａ−ホモエリスロマイシンＡ及び５−Ｏ−デソサミニル−９−デオキソ−９−ジヒドロ−９ａ−アザ−９ａ−ホモエリスロノリドＡの置換した９ａ−Ｎ−｛Ｎ’−［４−（スルホニル）フェニルカルバモイル］｝誘導体 | |
| MXPA99005226A (en) | Novel erythromycin derivatives, method for preparing them and their use as medicine | |
| JP2003534231A (ja) | 新規の６−デオキシエリスロマイシン誘導体、それらの製造方法及びそれらの薬剤としての使用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20101124 |