ZA200301047B - New macrolides with antibacterial activity. - Google Patents
New macrolides with antibacterial activity. Download PDFInfo
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- ZA200301047B ZA200301047B ZA200301047A ZA200301047A ZA200301047B ZA 200301047 B ZA200301047 B ZA 200301047B ZA 200301047 A ZA200301047 A ZA 200301047A ZA 200301047 A ZA200301047 A ZA 200301047A ZA 200301047 B ZA200301047 B ZA 200301047B
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- ZA
- South Africa
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- thio
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- 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 11
- 229940041033 macrolides Drugs 0.000 title abstract description 4
- 230000000844 anti-bacterial effect Effects 0.000 title description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000001727 in vivo Methods 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 pyridinyl- 1H-pyrazol-1-yl Chemical group 0.000 claims description 52
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 41
- KTSNTUOKEHVPGX-UHFFFAOYSA-N 1-oxacyclotetradeca-7,9-diene-2,5,11,13-tetrone Chemical compound O=C1CCC(=O)OCC(=O)CC(=O)C=CC=CC1 KTSNTUOKEHVPGX-UHFFFAOYSA-N 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 13
- 208000035473 Communicable disease Diseases 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000848 adenin-9-yl group Chemical group [H]N([H])C1=C2N=C([H])N(*)C2=NC([H])=N1 0.000 claims description 3
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- 239000000126 substance Substances 0.000 claims 6
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- 230000004071 biological effect Effects 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 13
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=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 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 10
- 239000003835 ketolide antibiotic agent Substances 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 9
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 8
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 8
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- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000010511 deprotection reaction Methods 0.000 description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 6
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
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- 241000606768 Haemophilus influenzae Species 0.000 description 4
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- 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 description 4
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Classifications
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0031—Rectum, anus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00117971 | 2000-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200301047B true ZA200301047B (en) | 2004-05-06 |
Family
ID=8169600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200301047A ZA200301047B (en) | 2000-08-22 | 2003-02-06 | New macrolides with antibacterial activity. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6740642B2 (zh) |
| EP (1) | EP1313751B1 (zh) |
| JP (1) | JP4162992B2 (zh) |
| KR (1) | KR100502031B1 (zh) |
| CN (1) | CN1234718C (zh) |
| AT (1) | ATE408614T1 (zh) |
| AU (1) | AU2001282105A1 (zh) |
| BR (1) | BR0113472A (zh) |
| CA (1) | CA2419296C (zh) |
| DE (1) | DE60135859D1 (zh) |
| ES (1) | ES2313975T3 (zh) |
| MX (1) | MXPA03001607A (zh) |
| WO (1) | WO2002016380A1 (zh) |
| ZA (1) | ZA200301047B (zh) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60124594T2 (de) * | 2000-12-21 | 2007-10-04 | Glaxo Group Ltd., Greenford | Makrolidantibiotika |
| FR2826274B1 (fr) * | 2001-06-21 | 2003-09-26 | Aventis Pharma Sa | Formulation pharmaceutique au gout masque et son procede de preparation |
| EP1430068A1 (en) | 2001-09-17 | 2004-06-23 | Ortho-Mcneil Pharmaceutical, Inc. | 6-o-carbamate-11,12-lacto-ketolide antimicrobials |
| US6995143B2 (en) * | 2002-02-28 | 2006-02-07 | Basilea Pharmaceutica Ag | Macrolides with antibacterial activity |
| US6727229B2 (en) * | 2002-08-19 | 2004-04-27 | Enanta Pharmaceuticals, Inc. | 11,12-substituted lactone ketolide derivatives having antibacterial activity |
| US6720308B1 (en) | 2002-11-07 | 2004-04-13 | Enanta Pharmaceuticals, Inc. | Anhydrolide derivatives having antibacterial activity |
| US20040254126A1 (en) * | 2003-06-05 | 2004-12-16 | Yao-Ling Qiu | 11-12 Bicyclic erythromycin derivatives |
| WO2004108745A2 (en) * | 2003-06-05 | 2004-12-16 | Enanta Pharmaceuticals, Inc. | 11-12 bicyclic erythromycin derivatives |
| US6716820B1 (en) | 2003-06-05 | 2004-04-06 | Enanta Pharmaceuticals, Inc. | 6-O-substituted bicyclic macrolides |
| US6774115B1 (en) | 2003-06-05 | 2004-08-10 | Enanta Pharmaceuticals, Inc. | 6-O-substituted bicyclic ketolides |
| US6765016B1 (en) | 2003-06-05 | 2004-07-20 | Enanta Pharmaceuticals, Inc. | Bicyclic ketolide derivatives |
| US6790835B1 (en) | 2003-06-05 | 2004-09-14 | Enanta Pharmaceuticals, Inc. | Bicyclic macrolide derivatives |
| US7291602B2 (en) * | 2004-12-13 | 2007-11-06 | Enanta Pharmaceuticals, Inc. | 11,12-lactone bicyclolides |
| ES2322775T3 (es) * | 2005-02-09 | 2009-06-26 | Basilea Pharmaceutica Ag | Nuevos macrolidos. |
| CN101115764B (zh) * | 2005-02-09 | 2012-09-26 | 巴斯利尔药物股份公司 | 大环内酯类化合物 |
| US7517859B2 (en) * | 2005-05-04 | 2009-04-14 | Enanta Pharmaceuticals, Inc. | Spirocyclic bicyclolides |
| WO2007025098A2 (en) | 2005-08-24 | 2007-03-01 | Rib-X Pharmaceuticals, Inc. | Triazole compounds and methods of making and using the same |
| EP2049556B1 (en) * | 2006-08-09 | 2013-07-03 | Basilea Pharmaceutica AG | New macrolides useful against inflammatory and allergic diseases |
| JP2010501541A (ja) * | 2006-08-24 | 2010-01-21 | ウォックハート リサーチ センター | 抗菌活性を有する新規マクロライド及びケトライド |
| WO2009106419A1 (en) * | 2008-02-08 | 2009-09-03 | Basilea Pharmaceutica Ag | New macrolides and their use |
| PT2247294E (pt) * | 2008-02-08 | 2014-07-10 | Basilea Pharmaceutica Ag | Macrólidos para o tratamento de doenças induzidas por inibição de pde |
| NZ596628A (en) | 2009-05-27 | 2013-03-28 | Ketolide compounds having antimicrobial activity | |
| US8796474B1 (en) | 2010-08-23 | 2014-08-05 | Rutgers, The State University Of New Jersey | Macrolide compounds and methods and intermediates useful for their preparation |
| CN102417530A (zh) * | 2010-09-26 | 2012-04-18 | 中国医学科学院药物研究所 | 广谱抗菌素红霉素a大环酮内酯类衍生物的合成方法和用途 |
| US9175031B2 (en) | 2010-12-09 | 2015-11-03 | Wockhardt Limited | Ketolide compounds |
| 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 |
| DK2938623T3 (en) * | 2012-12-31 | 2017-01-09 | Basilea Pharmaceutica Ag | SELECTED macrolides having PDE4 inhibitory activity |
| EP3402467A1 (en) * | 2016-01-12 | 2018-11-21 | Wockhardt Limited | Pharmaceutical compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2719587B1 (fr) * | 1994-05-03 | 1996-07-12 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
-
2001
- 2001-08-20 CN CNB018160891A patent/CN1234718C/zh not_active Expired - Fee Related
- 2001-08-20 BR BR0113472-8A patent/BR0113472A/pt not_active Application Discontinuation
- 2001-08-20 AT AT01960680T patent/ATE408614T1/de not_active IP Right Cessation
- 2001-08-20 DE DE60135859T patent/DE60135859D1/de not_active Expired - Lifetime
- 2001-08-20 EP EP01960680A patent/EP1313751B1/en not_active Expired - Lifetime
- 2001-08-20 KR KR10-2003-7002616A patent/KR100502031B1/ko not_active IP Right Cessation
- 2001-08-20 AU AU2001282105A patent/AU2001282105A1/en not_active Abandoned
- 2001-08-20 US US10/362,526 patent/US6740642B2/en not_active Expired - Lifetime
- 2001-08-20 ES ES01960680T patent/ES2313975T3/es not_active Expired - Lifetime
- 2001-08-20 CA CA002419296A patent/CA2419296C/en not_active Expired - Fee Related
- 2001-08-20 MX MXPA03001607A patent/MXPA03001607A/es active IP Right Grant
- 2001-08-20 WO PCT/EP2001/009560 patent/WO2002016380A1/en active IP Right Grant
- 2001-08-20 JP JP2002521477A patent/JP4162992B2/ja not_active Expired - Fee Related
-
2003
- 2003-02-06 ZA ZA200301047A patent/ZA200301047B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE408614T1 (de) | 2008-10-15 |
| US6740642B2 (en) | 2004-05-25 |
| KR20030029839A (ko) | 2003-04-16 |
| MXPA03001607A (es) | 2003-06-04 |
| KR100502031B1 (ko) | 2005-07-25 |
| CA2419296A1 (en) | 2002-02-28 |
| WO2002016380A1 (en) | 2002-02-28 |
| AU2001282105A1 (en) | 2002-03-04 |
| JP4162992B2 (ja) | 2008-10-08 |
| JP2004506740A (ja) | 2004-03-04 |
| CA2419296C (en) | 2008-12-09 |
| CN1234718C (zh) | 2006-01-04 |
| BR0113472A (pt) | 2003-07-01 |
| ES2313975T3 (es) | 2009-03-16 |
| DE60135859D1 (de) | 2008-10-30 |
| US20030199459A1 (en) | 2003-10-23 |
| EP1313751A1 (en) | 2003-05-28 |
| EP1313751B1 (en) | 2008-09-17 |
| CN1464880A (zh) | 2003-12-31 |
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