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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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 |
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| Country | Link |
|---|---|
| US (1) | US7202221B2 (enExample) |
| EP (1) | EP1453846B1 (enExample) |
| JP (1) | JP2005515978A (enExample) |
| CN (1) | CN1307194C (enExample) |
| AR (1) | AR037371A1 (enExample) |
| AT (1) | ATE362479T1 (enExample) |
| BR (1) | BR0214132A (enExample) |
| CA (1) | CA2466975A1 (enExample) |
| DE (1) | DE60220180T2 (enExample) |
| EA (1) | EA007433B1 (enExample) |
| ES (1) | ES2287332T3 (enExample) |
| GB (1) | GB0127349D0 (enExample) |
| HR (1) | HRP20040433A2 (enExample) |
| HU (1) | HUP0402225A3 (enExample) |
| IL (1) | IL161710A0 (enExample) |
| PL (1) | PL371472A1 (enExample) |
| RS (1) | RS41904A (enExample) |
| UA (1) | UA77210C2 (enExample) |
| WO (1) | WO2003042228A1 (enExample) |
| ZA (1) | ZA200403684B (enExample) |
Families Citing this family (32)
| 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 |
| US7022679B2 (en) | 2002-05-13 | 2006-04-04 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of 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 |
| 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 |
| US6764998B1 (en) | 2003-06-18 | 2004-07-20 | Enanta Pharmaceuticals, Inc. | 6,11-4C-bicyclic 9a-azalide derivatives |
| EP1503759B1 (en) * | 2002-05-14 | 2008-12-17 | The Regents Of The University Of California | Substituted quinolone carboxylic acids, their derivatives, site of action, and uses thereof |
| US7091196B2 (en) | 2002-09-26 | 2006-08-15 | Rib-X Pharmaceuticals, Inc. | Bifunctional heterocyclic compounds and methods of making and using same |
| 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 |
| EP1628989B1 (en) * | 2003-05-13 | 2006-12-20 | Glaxo Group Limited | Novel 14 and 15 membered-ring compounds |
| 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 |
| GB0310980D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| GB0310986D0 (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 |
| US7265094B2 (en) | 2004-01-09 | 2007-09-04 | Enanta Pharmaceuticals, Inc. | 9N-substituted 6-11 bicyclic erythromycin derivatives |
| EP2716647A3 (en) | 2004-02-27 | 2014-08-20 | Rib-X Pharmaceuticals, Inc. | Macrocyclic compounds and methods of making and using the same |
| AU2005240849B2 (en) * | 2004-05-06 | 2008-10-23 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | Ester linked macrolides useful for the treatment of microbial infections |
| CA2566112A1 (en) * | 2004-05-06 | 2005-11-17 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O | Carbamate linked macrolides useful for the treatment of microbial infections |
| 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 |
| GB0424961D0 (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 |
| 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 |
| ES2428874T3 (es) * | 2006-08-09 | 2013-11-12 | Basilea Pharmaceutica Ag | Nuevos macrólidos útiles contra las enfermedades inflamatorias y alérgicas |
| CN101541331A (zh) | 2006-08-24 | 2009-09-23 | 沃克哈特研究中心 | 具有抗微生物活性的新颖大环内酯和酮内酯 |
| US8410065B2 (en) | 2008-02-08 | 2013-04-02 | Basilea Pharmaceutica Ag | Macrolides and their use |
| EP2435460B1 (en) | 2009-05-27 | 2015-01-07 | Wockhardt Limited | Ketolide compounds having antimicrobial activity |
| RU2601550C2 (ru) | 2010-12-09 | 2016-11-10 | Вокхардт Лимитед | Кетолидные соединения |
| EP2671887A4 (en) * | 2011-01-31 | 2014-06-25 | Meiji Seika Pharma Co Ltd | NEW MAKROLIDE DERIVATIVES |
| 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 |
| CN119060110A (zh) * | 2023-05-30 | 2024-12-03 | 北京理工大学 | 一种红霉素衍生物及其制备方法和应用 |
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 |
| ES2252784T3 (es) | 1996-05-07 | 2006-05-16 | Abbott Laboratories | Compuestos a base de eritromicina 6-0 sustituida y tecnica de produccion. |
| 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 |
| EE200100613A (et) | 1999-05-24 | 2003-02-17 | Pfizer Products Inc. | 13-metüülerütromütsiini derivaadid |
| CA2380455C (en) | 1999-08-24 | 2009-06-02 | Abbott Laboratories | 9a-azalides with antibacterial activity |
| WO2001063539A2 (en) | 2000-02-24 | 2001-08-30 | Abbott Laboratories | Anti-infective agents useful against multidrug-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
-
2002
- 2002-11-13 AR ARP020104364A patent/AR037371A1/es unknown
- 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 WO PCT/GB2002/005101 patent/WO2003042228A1/en not_active Ceased
- 2002-11-13 HU HU0402225A patent/HUP0402225A3/hu unknown
- 2002-11-13 HR HR20040433A patent/HRP20040433A2/hr not_active Application Discontinuation
- 2002-11-13 CN CNB028270452A patent/CN1307194C/zh not_active Expired - Fee Related
- 2002-11-13 US US10/495,413 patent/US7202221B2/en not_active Expired - Fee Related
- 2002-11-13 EA EA200400536A patent/EA007433B1/ru not_active IP Right Cessation
- 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 CA CA002466975A patent/CA2466975A1/en not_active Abandoned
- 2002-11-13 EP EP02779670A patent/EP1453846B1/en not_active Expired - Lifetime
- 2002-11-13 UA UA20040503313A patent/UA77210C2/uk unknown
- 2002-11-13 IL IL16171002A patent/IL161710A0/xx unknown
- 2002-11-13 AT AT02779670T patent/ATE362479T1/de not_active IP Right Cessation
- 2002-11-13 PL PL02371472A patent/PL371472A1/xx not_active Application Discontinuation
- 2002-11-13 JP JP2003544063A patent/JP2005515978A/ja active Pending
-
2004
- 2004-05-13 ZA ZA200403684A patent/ZA200403684B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR037371A1 (es) | 2004-11-03 |
| US7202221B2 (en) | 2007-04-10 |
| EA007433B1 (ru) | 2006-10-27 |
| ATE362479T1 (de) | 2007-06-15 |
| DE60220180D1 (de) | 2007-06-28 |
| HUP0402225A3 (en) | 2006-01-30 |
| GB0127349D0 (en) | 2002-01-02 |
| IL161710A0 (en) | 2004-09-27 |
| US20050080025A1 (en) | 2005-04-14 |
| CN1307194C (zh) | 2007-03-28 |
| WO2003042228A1 (en) | 2003-05-22 |
| ZA200403684B (en) | 2005-09-13 |
| EP1453846B1 (en) | 2007-05-16 |
| BR0214132A (pt) | 2004-09-14 |
| CA2466975A1 (en) | 2003-05-22 |
| HRP20040433A2 (en) | 2005-04-30 |
| EA200400536A1 (ru) | 2004-12-30 |
| PL371472A1 (en) | 2005-06-13 |
| HUP0402225A2 (hu) | 2005-02-28 |
| RS41904A (sr) | 2006-10-27 |
| JP2005515978A (ja) | 2005-06-02 |
| CN1612888A (zh) | 2005-05-04 |
| DE60220180T2 (de) | 2008-01-17 |
| ES2287332T3 (es) | 2007-12-16 |
| EP1453846A1 (en) | 2004-09-08 |
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