UA77210C2 - Macrolids, process for their manufacture (variants), pharmaceutical composition, method for treatment of bacterial infections - Google Patents
Macrolids, process for their manufacture (variants), pharmaceutical composition, method for treatment of bacterial infections Download PDFInfo
- Publication number
- UA77210C2 UA77210C2 UA20040503313A UA20040503313A UA77210C2 UA 77210 C2 UA77210 C2 UA 77210C2 UA 20040503313 A UA20040503313 A UA 20040503313A UA 20040503313 A UA20040503313 A UA 20040503313A UA 77210 C2 UA77210 C2 UA 77210C2
- Authority
- UA
- Ukraine
- Prior art keywords
- amino
- dihydro
- oxo
- compound
- cyclopropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 208000035143 Bacterial infection Diseases 0.000 title claims abstract description 8
- 208000022362 bacterial infectious disease Diseases 0.000 title claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 230000009885 systemic effect Effects 0.000 claims abstract description 5
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 439
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 147
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 124
- 229960002626 clarithromycin Drugs 0.000 claims description 73
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 229960004099 azithromycin Drugs 0.000 claims description 31
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 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 description 6
- 241000282414 Homo sapiens Species 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 244000068988 Glycine max Species 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 3
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- 229940079593 drug Drugs 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
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- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 claims 1
- 244000309466 calf Species 0.000 claims 1
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- 238000012876 topography Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 379
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- 238000003818 flash chromatography Methods 0.000 description 69
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 37
- 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 35
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- -1 for example Chemical group 0.000 description 28
- 229920006395 saturated elastomer Polymers 0.000 description 28
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- 239000007864 aqueous solution Substances 0.000 description 26
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- 239000012044 organic layer Substances 0.000 description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 18
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 17
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
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- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 8
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- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 7
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- 238000001556 precipitation Methods 0.000 description 7
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
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- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 6
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 6
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- 239000002798 polar solvent Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0127349.9A GB0127349D0 (en) | 2001-11-14 | 2001-11-14 | Macrolides |
| PCT/GB2002/005101 WO2003042228A1 (en) | 2001-11-14 | 2002-11-13 | Macrolides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77210C2 true UA77210C2 (en) | 2006-11-15 |
Family
ID=9925777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040503313A UA77210C2 (en) | 2001-11-14 | 2002-11-13 | Macrolids, process for their manufacture (variants), pharmaceutical composition, method for treatment of bacterial infections |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7202221B2 (zh) |
| EP (1) | EP1453846B1 (zh) |
| JP (1) | JP2005515978A (zh) |
| CN (1) | CN1307194C (zh) |
| AR (1) | AR037371A1 (zh) |
| AT (1) | ATE362479T1 (zh) |
| BR (1) | BR0214132A (zh) |
| CA (1) | CA2466975A1 (zh) |
| DE (1) | DE60220180T2 (zh) |
| EA (1) | EA007433B1 (zh) |
| ES (1) | ES2287332T3 (zh) |
| GB (1) | GB0127349D0 (zh) |
| HR (1) | HRP20040433A2 (zh) |
| HU (1) | HUP0402225A3 (zh) |
| IL (1) | IL161710A0 (zh) |
| PL (1) | PL371472A1 (zh) |
| RS (1) | RS41904A (zh) |
| UA (1) | UA77210C2 (zh) |
| WO (1) | WO2003042228A1 (zh) |
| ZA (1) | ZA200403684B (zh) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6995143B2 (en) * | 2002-02-28 | 2006-02-07 | Basilea Pharmaceutica Ag | Macrolides with antibacterial activity |
| US7910558B2 (en) | 2002-05-13 | 2011-03-22 | Enanta Pharmaceuticals, Inc. | Bridged macrocyclic compounds and processes for the preparation thereof |
| US6764998B1 (en) | 2003-06-18 | 2004-07-20 | Enanta Pharmaceuticals, Inc. | 6,11-4C-bicyclic 9a-azalide 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 |
| WO2005070918A1 (en) | 2002-05-13 | 2005-08-04 | Enanta Pharmaceuticals, Inc. | Process for the preparation of t-11 bicyclic erythromycin derivatives |
| CN1652784A (zh) * | 2002-05-14 | 2005-08-10 | 加利福尼亚大学董事会 | 取代的喹诺酮羧酸、它们的衍生物、作用部位、以及其用途 |
| AR043050A1 (es) | 2002-09-26 | 2005-07-13 | Rib X Pharmaceuticals Inc | Compuestos heterociclicos bifuncionales y metodos para preparar y usar los mismos |
| GB0225384D0 (en) | 2002-10-31 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
| US6645941B1 (en) | 2003-03-26 | 2003-11-11 | Enanta Pharmaceuticals, Inc. | 6,11-3C-bicyclic 9a-azalide derivatives |
| GB0310979D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| GB0310984D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| PL1628989T3 (pl) * | 2003-05-13 | 2007-05-31 | Glaxo Group Ltd | Nowe związki o 14- i 15- członowym pierścieniu |
| GB0310986D0 (en) | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| GB0310980D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| US7276487B2 (en) | 2003-09-23 | 2007-10-02 | Enanta Pharmaceuticals, Inc. | 9a, 11-3C-bicyclic 9a-azalide derivatives |
| WO2005070113A2 (en) | 2004-01-09 | 2005-08-04 | Enanta Pharmaceuticals, Inc. | 9n-substituted 6-11 bicyclic erythromycin derivatives |
| CN102816194A (zh) | 2004-02-27 | 2012-12-12 | 瑞伯-X医药品有限公司 | 大环化合物以及其制作和使用方法 |
| JP2007536372A (ja) * | 2004-05-06 | 2007-12-13 | グラクソスミスクライン・イストラジヴァッキ・センタル・ザグレブ・ドルズバ・ゼー・オメイェノ・オドゴヴォルノスティオ | 微生物感染症の治療に有用なカルバミン酸エステル結合マクロライド |
| BRPI0510328A (pt) * | 2004-05-06 | 2007-10-23 | Glaxosmithkline Zagreb | macrolìdeos ligados a éster úteis para o tratamento de infecções microbianas |
| WO2006047167A2 (en) * | 2004-10-21 | 2006-05-04 | Janssen Pharmaceutica, N.V. | 9 alkyl and 9 alkylidenyl 6-0 alkyl-11, 12 carbamate ketolide antimicrobials |
| GB0424959D0 (en) | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| GB0424951D0 (en) * | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| GB0424958D0 (en) * | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| GB0424961D0 (en) * | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| JP5254231B2 (ja) * | 2006-08-09 | 2013-08-07 | バジリア ファルマスーチカ アーゲー | 炎症性及びアレルギー性疾患に対して有用な新規マクロライド |
| KR20090042971A (ko) | 2006-08-24 | 2009-05-04 | 욱크하르트 리서치 센터 | 항미생물 활성을 갖는 신규한 마크로라이드 및 케토라이드 |
| BRPI0908343A2 (pt) | 2008-02-08 | 2020-08-18 | Basilea Pharmaceutica Ag | macrolídeos e seu uso |
| EP2435460B1 (en) | 2009-05-27 | 2015-01-07 | Wockhardt Limited | Ketolide compounds having antimicrobial activity |
| PT2673285T (pt) | 2010-12-09 | 2017-10-19 | Wockhardt Ltd | Resumo |
| EP2671887A4 (en) * | 2011-01-31 | 2014-06-25 | Meiji Seika Pharma Co Ltd | NEW MACROLIDE DERIVATIVE |
| CN103619849B (zh) | 2011-03-01 | 2016-05-25 | 沃克哈特有限公司 | 酮内酯中间体的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126344A2 (en) | 1983-05-20 | 1984-11-28 | Abbott Laboratories | Tripeptide esters of therapeutic agents |
| US4742049A (en) * | 1986-06-04 | 1988-05-03 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
| IL93936A (en) | 1989-03-28 | 1994-06-24 | Abbott Lab | History of 9-dioxo-21,9-epoxy - erythromycin, method of preparation History of 11-oxo and 11-hydroxy, and pharmaceutical preparations containing them |
| CA2064634C (en) | 1991-04-04 | 1998-08-04 | James V. Heck | 9-deoxo-8a-aza-8a-homoerythromycin a derivatives modified at the 4"- and8a-positions |
| IL126625A0 (en) | 1996-05-07 | 1999-08-17 | Abbott Lab | 6-o-substituted erythromycin compounds and method for making same |
| EP0895999A1 (en) * | 1997-08-06 | 1999-02-10 | Pfizer Products Inc. | C-4" substituted macrolide antibiotics |
| US6262030B1 (en) * | 1998-11-03 | 2001-07-17 | Pfizer Inc. | Erythromycin derivatives |
| EP1180110A1 (en) | 1999-05-24 | 2002-02-20 | Pfizer Products Inc. | 13-methyl-erythromycin derivatives |
| PT1206476E (pt) | 1999-08-24 | 2006-05-31 | Abbott Lab | 9a-azalidos com actividade antibacteriana |
| EP1259923B1 (en) | 2000-02-24 | 2005-12-14 | Abbott Laboratories | Anti-infective agents useful against mulitidrug-resistant strains of bacteria |
| US6946446B2 (en) * | 2000-02-24 | 2005-09-20 | Abbott Laboratories | Anti-infective agents useful against multidrug-resistant strains of bacteria |
| JP2002173498A (ja) | 2000-09-27 | 2002-06-21 | Hokuriku Seiyaku Co Ltd | エリスロマイシン誘導体 |
| GB0025688D0 (en) * | 2000-10-19 | 2000-12-06 | Glaxo Group Ltd | Macrolides |
-
2001
- 2001-11-14 GB GBGB0127349.9A patent/GB0127349D0/en not_active Ceased
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2002
- 2002-11-13 AR ARP020104364A patent/AR037371A1/es unknown
- 2002-11-13 DE DE60220180T patent/DE60220180T2/de not_active Expired - Fee Related
- 2002-11-13 ES ES02779670T patent/ES2287332T3/es not_active Expired - Lifetime
- 2002-11-13 PL PL02371472A patent/PL371472A1/xx not_active Application Discontinuation
- 2002-11-13 HU HU0402225A patent/HUP0402225A3/hu unknown
- 2002-11-13 AT AT02779670T patent/ATE362479T1/de not_active IP Right Cessation
- 2002-11-13 CN CNB028270452A patent/CN1307194C/zh not_active Expired - Fee Related
- 2002-11-13 BR BR0214132-9A patent/BR0214132A/pt not_active IP Right Cessation
- 2002-11-13 RS YU41904A patent/RS41904A/sr unknown
- 2002-11-13 JP JP2003544063A patent/JP2005515978A/ja active Pending
- 2002-11-13 CA CA002466975A patent/CA2466975A1/en not_active Abandoned
- 2002-11-13 UA UA20040503313A patent/UA77210C2/uk unknown
- 2002-11-13 WO PCT/GB2002/005101 patent/WO2003042228A1/en active IP Right Grant
- 2002-11-13 EA EA200400536A patent/EA007433B1/ru not_active IP Right Cessation
- 2002-11-13 EP EP02779670A patent/EP1453846B1/en not_active Expired - Lifetime
- 2002-11-13 IL IL16171002A patent/IL161710A0/xx unknown
- 2002-11-13 US US10/495,413 patent/US7202221B2/en not_active Expired - Fee Related
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2004
- 2004-05-13 ZA ZA200403684A patent/ZA200403684B/xx unknown
- 2004-05-14 HR HR20040433A patent/HRP20040433A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US7202221B2 (en) | 2007-04-10 |
| EP1453846B1 (en) | 2007-05-16 |
| HUP0402225A2 (hu) | 2005-02-28 |
| EP1453846A1 (en) | 2004-09-08 |
| DE60220180D1 (de) | 2007-06-28 |
| DE60220180T2 (de) | 2008-01-17 |
| PL371472A1 (en) | 2005-06-13 |
| US20050080025A1 (en) | 2005-04-14 |
| ATE362479T1 (de) | 2007-06-15 |
| HUP0402225A3 (en) | 2006-01-30 |
| CN1612888A (zh) | 2005-05-04 |
| WO2003042228A1 (en) | 2003-05-22 |
| RS41904A (en) | 2006-10-27 |
| CN1307194C (zh) | 2007-03-28 |
| ZA200403684B (en) | 2005-09-13 |
| EA007433B1 (ru) | 2006-10-27 |
| BR0214132A (pt) | 2004-09-14 |
| AR037371A1 (es) | 2004-11-03 |
| ES2287332T3 (es) | 2007-12-16 |
| JP2005515978A (ja) | 2005-06-02 |
| HRP20040433A2 (en) | 2005-04-30 |
| IL161710A0 (en) | 2004-09-27 |
| CA2466975A1 (en) | 2003-05-22 |
| GB0127349D0 (en) | 2002-01-02 |
| EA200400536A1 (ru) | 2004-12-30 |
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