NO312678B1 - Nye 5-O-deoaminyl-6-O-metylerytronolid A-derivater, fremgangsmåte for fremstilling av disse, og mellomprodukter veddenne - Google Patents
Nye 5-O-deoaminyl-6-O-metylerytronolid A-derivater, fremgangsmåte for fremstilling av disse, og mellomprodukter veddenne Download PDFInfo
- Publication number
- NO312678B1 NO312678B1 NO19981053A NO981053A NO312678B1 NO 312678 B1 NO312678 B1 NO 312678B1 NO 19981053 A NO19981053 A NO 19981053A NO 981053 A NO981053 A NO 981053A NO 312678 B1 NO312678 B1 NO 312678B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- formula
- compound
- compounds
- oxime
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000543 intermediate Substances 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- -1 alkoxy radical Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229960003276 erythromycin Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 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 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9510601A FR2738571B1 (fr) | 1995-09-11 | 1995-09-11 | Nouveaux derives de la 5-0-desosaminyl 6-0-methyl- erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs |
| PCT/FR1996/001384 WO1997010251A1 (fr) | 1995-09-11 | 1996-09-10 | Nouveaux derives de la 5-0-desosaminyl 6-0-methyl erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO981053D0 NO981053D0 (no) | 1998-03-10 |
| NO981053L NO981053L (no) | 1998-03-10 |
| NO312678B1 true NO312678B1 (no) | 2002-06-17 |
Family
ID=9482423
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19981053A NO312678B1 (no) | 1995-09-11 | 1998-03-10 | Nye 5-O-deoaminyl-6-O-metylerytronolid A-derivater, fremgangsmåte for fremstilling av disse, og mellomprodukter veddenne |
| NO20021111A NO315048B1 (no) | 1995-09-11 | 2002-03-06 | Fremgangsmåte for fremstilling av 5-O-desosaminyl-6-O- metylerytronolid A-derivater |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20021111A NO315048B1 (no) | 1995-09-11 | 2002-03-06 | Fremgangsmåte for fremstilling av 5-O-desosaminyl-6-O- metylerytronolid A-derivater |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US5969161A (uk) |
| EP (1) | EP0854880B1 (uk) |
| JP (1) | JP4332218B2 (uk) |
| KR (1) | KR100457755B1 (uk) |
| CN (2) | CN1237069C (uk) |
| AP (1) | AP887A (uk) |
| AR (1) | AR004195A1 (uk) |
| AT (1) | ATE266035T1 (uk) |
| AU (1) | AU708811B2 (uk) |
| BG (1) | BG63822B1 (uk) |
| BR (1) | BR9610503A (uk) |
| CA (1) | CA2228670C (uk) |
| CZ (3) | CZ294865B6 (uk) |
| DE (1) | DE69632405T2 (uk) |
| DK (1) | DK0854880T3 (uk) |
| EA (1) | EA000575B1 (uk) |
| EE (1) | EE03774B1 (uk) |
| ES (1) | ES2219698T3 (uk) |
| FR (1) | FR2738571B1 (uk) |
| GE (1) | GEP20022838B (uk) |
| HK (2) | HK1016187A1 (uk) |
| HU (1) | HU227565B1 (uk) |
| IL (1) | IL123550A (uk) |
| MX (1) | MX9801859A (uk) |
| NO (2) | NO312678B1 (uk) |
| PL (1) | PL183652B1 (uk) |
| PT (1) | PT854880E (uk) |
| RO (1) | RO120137B1 (uk) |
| SI (1) | SI0854880T1 (uk) |
| SK (3) | SK283690B6 (uk) |
| TR (1) | TR199800438T1 (uk) |
| UA (1) | UA53628C2 (uk) |
| WO (1) | WO1997010251A1 (uk) |
| ZA (1) | ZA966837B (uk) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA51730C2 (uk) * | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
| KR100610043B1 (ko) * | 1996-09-04 | 2006-08-08 | 아보트 러보러터리즈 | 항균 활성을 지닌 6-ｏ-치환된 케톨라이드 |
| US6034069A (en) * | 1997-09-30 | 2000-03-07 | Abbott Laboratories | 3-'N-modified 6-O-substituted erythromycin ketolide derivatives having antibacterial activity |
| US6046171A (en) * | 1997-10-29 | 2000-04-04 | Abbott Laboratories | 6,11-bridged erythromycin derivatives |
| US6124269A (en) * | 1997-10-29 | 2000-09-26 | Abbott Laboratories | 2-Halo-6-O-substituted ketolide derivatives |
| US6054435A (en) * | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
| US6420535B1 (en) | 1999-06-07 | 2002-07-16 | Abbott Laboratories | 6-O-carbamate ketolide derivatives |
| US7579324B2 (en) * | 2002-02-15 | 2009-08-25 | C-A-I-R Biosciences Gmbh | Conjugates of biologically active compounds, methods for their preparation and use, formulation and pharmaceutical applications thereof |
| WO2005070918A1 (en) * | 2002-05-13 | 2005-08-04 | Enanta Pharmaceuticals, Inc. | Process for the preparation of t-11 bicyclic erythromycin derivatives |
| US6841664B2 (en) | 2002-07-25 | 2005-01-11 | Enanra Pharmaceuticals, Inc. | 6,11-4-carbon bridged ketolides |
| US6764998B1 (en) | 2003-06-18 | 2004-07-20 | Enanta Pharmaceuticals, Inc. | 6,11-4C-bicyclic 9a-azalide derivatives |
| US6753318B1 (en) | 2002-07-25 | 2004-06-22 | Enanta Pharmaceuticals, Inc. | 6,11-4-carbon bridged erythromycin derivatives |
| US7135573B2 (en) * | 2002-05-13 | 2006-11-14 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of O-(6-Pyrazol-1-yl-pyridin-3-ylmethyl)-hydroxylamine |
| US6878691B2 (en) * | 2002-05-13 | 2005-04-12 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide derivatives |
| EP1509538A1 (en) * | 2002-05-13 | 2005-03-02 | Enanta Pharmaceuticals, Inc. | 6,11 bicyclic erythromycin derivatives |
| US7910558B2 (en) * | 2002-05-13 | 2011-03-22 | Enanta Pharmaceuticals, Inc. | Bridged macrocyclic compounds and processes for the preparation thereof |
| US7273853B2 (en) * | 2002-05-13 | 2007-09-25 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide derivatives |
| US7064110B2 (en) * | 2002-05-13 | 2006-06-20 | Enanta Pharmaceuticals, Inc. | 6-11 bicycle ketolide derivatives |
| ITMI20021726A1 (it) * | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| US6645941B1 (en) | 2003-03-26 | 2003-11-11 | Enanta Pharmaceuticals, Inc. | 6,11-3C-bicyclic 9a-azalide derivatives |
| US7276487B2 (en) * | 2003-09-23 | 2007-10-02 | Enanta Pharmaceuticals, Inc. | 9a, 11-3C-bicyclic 9a-azalide derivatives |
| WO2005067564A2 (en) | 2004-01-07 | 2005-07-28 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic erythromycin derivatives |
| US7265094B2 (en) * | 2004-01-09 | 2007-09-04 | Enanta Pharmaceuticals, Inc. | 9N-substituted 6-11 bicyclic erythromycin derivatives |
| US7229972B2 (en) | 2004-12-07 | 2007-06-12 | Enanta Pharmaceuticals, Inc. | 3,6-Bicyclolides |
| US7419962B2 (en) | 2004-12-07 | 2008-09-02 | Enanta Pharmaceuticals, Inc. | 3,6-bicyclolides |
| WO2006065721A2 (en) | 2004-12-13 | 2006-06-22 | Enanta Pharmaceuticals, Inc. | 11, 12-lactone bicyclolides |
| TW200635600A (en) | 2004-12-13 | 2006-10-16 | Enanta Pharm Inc | Tetracyclic bicyclolides |
| US7384922B2 (en) * | 2005-05-04 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | 6-11 bridged oxime erythromycin derivatives |
| WO2007012464A1 (en) * | 2005-07-26 | 2007-02-01 | Merckle Gmbh | Macrolide conjugates of pyrrolizine and indolizine compounds as inhibitors of 5-lipooxygenase and cyclooxygenase |
| US8354383B2 (en) * | 2007-09-17 | 2013-01-15 | Enanta Pharmaceuticals, Inc. | 6,11-bridged biaryl macrolides |
| US8273720B2 (en) * | 2007-09-17 | 2012-09-25 | Enanta Pharmaceuticals, Inc. | 6,11-bicyclolides: bridged biaryl macrolide derivatives |
| EP2203435B1 (en) * | 2007-09-17 | 2018-07-18 | Enanta Pharmaceuticals, Inc. | 6, 11-bridged biaryl macrolides |
| CN103232501A (zh) * | 2013-04-11 | 2013-08-07 | 宜昌东阳光药业股份有限公司 | 阿奇霉素或阿奇霉素的中间体脱去克拉定糖化合物的制备工艺 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960000434B1 (ko) * | 1986-12-17 | 1996-01-06 | 다이쇼 세이야꾸 가부시끼가이샤 | 에리스로마이신 a유도체 및 그의 제조 방법 |
| US5523399A (en) * | 1991-12-27 | 1996-06-04 | Taisho Pharmaceutical Co., Ltd. | 5-O-desosaminylerythronolide derivatives |
-
1995
- 1995-09-11 FR FR9510601A patent/FR2738571B1/fr not_active Expired - Lifetime
-
1996
- 1996-08-13 ZA ZA9606837A patent/ZA966837B/xx unknown
- 1996-09-05 AR ARP960104239A patent/AR004195A1/es unknown
- 1996-09-10 US US09/043,044 patent/US5969161A/en not_active Expired - Lifetime
- 1996-09-10 SI SI9630684T patent/SI0854880T1/xx unknown
- 1996-09-10 PL PL96326274A patent/PL183652B1/pl unknown
- 1996-09-10 HU HU9802930A patent/HU227565B1/hu unknown
- 1996-09-10 AT AT96931098T patent/ATE266035T1/de active
- 1996-09-10 BR BR9610503A patent/BR9610503A/pt not_active IP Right Cessation
- 1996-09-10 SK SK294-98A patent/SK283690B6/sk not_active IP Right Cessation
- 1996-09-10 AU AU69910/96A patent/AU708811B2/en not_active Expired
- 1996-09-10 CZ CZ20012389A patent/CZ294865B6/cs not_active IP Right Cessation
- 1996-09-10 EA EA199800288A patent/EA000575B1/ru not_active IP Right Cessation
- 1996-09-10 RO RO98-00685A patent/RO120137B1/ro unknown
- 1996-09-10 CZ CZ20012390A patent/CZ294866B6/cs not_active IP Right Cessation
- 1996-09-10 JP JP51169697A patent/JP4332218B2/ja not_active Expired - Lifetime
- 1996-09-10 KR KR10-1998-0701791A patent/KR100457755B1/ko not_active IP Right Cessation
- 1996-09-10 PT PT96931098T patent/PT854880E/pt unknown
- 1996-09-10 WO PCT/FR1996/001384 patent/WO1997010251A1/fr active IP Right Grant
- 1996-09-10 TR TR1998/00438T patent/TR199800438T1/xx unknown
- 1996-09-10 SK SK893-2003A patent/SK285853B6/sk not_active IP Right Cessation
- 1996-09-10 DE DE69632405T patent/DE69632405T2/de not_active Expired - Lifetime
- 1996-09-10 CN CNB001309064A patent/CN1237069C/zh not_active Expired - Lifetime
- 1996-09-10 DK DK96931098T patent/DK0854880T3/da active
- 1996-09-10 AP APAP/P/1998/001210A patent/AP887A/en active
- 1996-09-10 EP EP96931098A patent/EP0854880B1/fr not_active Expired - Lifetime
- 1996-09-10 IL IL12355096A patent/IL123550A/en not_active IP Right Cessation
- 1996-09-10 GE GEAP19964228A patent/GEP20022838B/en unknown
- 1996-09-10 EE EE9800065A patent/EE03774B1/xx unknown
- 1996-09-10 CN CN96198171A patent/CN1070498C/zh not_active Expired - Lifetime
- 1996-09-10 ES ES96931098T patent/ES2219698T3/es not_active Expired - Lifetime
- 1996-09-10 SK SK892-2003A patent/SK285995B6/sk not_active IP Right Cessation
- 1996-09-10 CA CA002228670A patent/CA2228670C/fr not_active Expired - Lifetime
- 1996-09-10 CZ CZ1998717A patent/CZ289945B6/cs not_active IP Right Cessation
- 1996-10-09 UA UA98041835A patent/UA53628C2/uk unknown
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1998
- 1998-03-09 MX MX9801859A patent/MX9801859A/es unknown
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- 1998-03-10 NO NO19981053A patent/NO312678B1/no not_active IP Right Cessation
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1999
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2002
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