CN101541331A - 具有抗微生物活性的新颖大环内酯和酮内酯 - Google Patents
具有抗微生物活性的新颖大环内酯和酮内酯 Download PDFInfo
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- CN101541331A CN101541331A CNA2007800373931A CN200780037393A CN101541331A CN 101541331 A CN101541331 A CN 101541331A CN A2007800373931 A CNA2007800373931 A CN A2007800373931A CN 200780037393 A CN200780037393 A CN 200780037393A CN 101541331 A CN101541331 A CN 101541331A
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- chemical compound
- phenyl
- oxadiazole
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- 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 25
- 239000003835 ketolide antibiotic agent Substances 0.000 title abstract description 14
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- 238000000034 method Methods 0.000 claims abstract description 38
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- -1 triethylsilyl Chemical group 0.000 claims description 222
- 239000002585 base Substances 0.000 claims description 140
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
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- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
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- 125000002769 thiazolinyl group Chemical group 0.000 claims description 10
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- YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
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- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 229950004288 tosilate Drugs 0.000 description 1
- 230000008359 toxicosis Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1336MU2006 | 2006-08-24 | ||
| IN1336/MUM/2006 | 2006-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101541331A true CN101541331A (zh) | 2009-09-23 |
Family
ID=39107171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007800373931A Pending CN101541331A (zh) | 2006-08-24 | 2007-08-22 | 具有抗微生物活性的新颖大环内酯和酮内酯 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8097594B2 (https=) |
| EP (1) | EP2056844A4 (https=) |
| JP (1) | JP2010501541A (https=) |
| KR (1) | KR20090042971A (https=) |
| CN (1) | CN101541331A (https=) |
| CA (1) | CA2661538A1 (https=) |
| WO (1) | WO2008023248A2 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012163291A1 (zh) * | 2011-06-02 | 2012-12-06 | 广州翰鼎医药科技有限公司 | 用于抑制肿瘤转移和肿瘤血管生长的苯基哌嗪类衍生物 |
| CN103384676A (zh) * | 2010-12-09 | 2013-11-06 | 沃克哈特有限公司 | 酮内酯化合物 |
| CN103619863A (zh) * | 2011-03-22 | 2014-03-05 | 沃克哈特有限公司 | 酮内酯化合物的制备方法 |
| CN103619849A (zh) * | 2011-03-01 | 2014-03-05 | 沃克哈特有限公司 | 酮内酯中间体的制备方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101669432B1 (ko) | 2007-08-27 | 2016-10-26 | 다트 뉴로사이언스 (케이만) 엘티디. | 치료적 이속사졸 화합물 |
| CN101910159B (zh) * | 2007-12-26 | 2013-06-19 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的制备方法 |
| ES2561332T3 (es) | 2009-05-27 | 2016-02-25 | Wockhardt Limited | Compuestos cetólidos que tienen actividad antimicrobiana |
| WO2012129564A2 (en) | 2011-03-24 | 2012-09-27 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Proteasome chymotrypsin-like inhibition using pi-1833 analogs |
| CN106998685A (zh) * | 2014-10-08 | 2017-08-01 | 哈佛大学的校长及成员们 | 14‑元酮内酯及其制备和使用方法 |
| KR20190129863A (ko) * | 2017-03-16 | 2019-11-20 | 욱크하르트 리미티드 | 케톨라이드 화합물의 제조 방법 |
| ES2948122A1 (es) * | 2022-02-10 | 2023-08-31 | Fundacion Instituto De Investig Sanitaria Aragon | Compuestos para el tratamiento y/o prevención de una infección o enfermedad causada por Helicobacter o Campylobacter |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2473525A1 (fr) | 1980-01-11 | 1981-07-17 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US4331803A (en) | 1980-06-04 | 1982-05-25 | Taisho Pharmaceutical Co., Ltd. | Novel erythromycin compounds |
| 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 |
| FR2719587B1 (fr) | 1994-05-03 | 1996-07-12 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| DE69733422T2 (de) | 1996-09-04 | 2006-05-04 | Abbott Laboratories, Abbott Park | 6-0-substituierte ketoliden mit antibakteriellen wirkung |
| JP4162992B2 (ja) * | 2000-08-22 | 2008-10-08 | バジリア ファルマスーチカ アーゲー | 抗菌活性を有する新規マクロライド |
| US20040077557A1 (en) * | 2000-12-21 | 2004-04-22 | Sulejman Ali | Macrolide antibiotics |
| GB0031312D0 (en) | 2000-12-21 | 2001-02-07 | Glaxo Group Ltd | Macrolides |
| EP1406898B1 (en) | 2001-07-19 | 2005-04-06 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| GB0127349D0 (en) | 2001-11-14 | 2002-01-02 | Glaxo Group Ltd | Macrolides |
| 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 |
| JP5112079B2 (ja) * | 2005-02-09 | 2013-01-09 | バジリア ファルマスーチカ アーゲー | 新規なマクロライド |
-
2007
- 2007-08-22 CA CA002661538A patent/CA2661538A1/en not_active Abandoned
- 2007-08-22 EP EP07804796A patent/EP2056844A4/en not_active Withdrawn
- 2007-08-22 WO PCT/IB2007/002405 patent/WO2008023248A2/en not_active Ceased
- 2007-08-22 JP JP2009525123A patent/JP2010501541A/ja active Pending
- 2007-08-22 CN CNA2007800373931A patent/CN101541331A/zh active Pending
- 2007-08-22 KR KR1020097005432A patent/KR20090042971A/ko not_active Ceased
-
2009
- 2009-02-24 US US12/379,539 patent/US8097594B2/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103384676A (zh) * | 2010-12-09 | 2013-11-06 | 沃克哈特有限公司 | 酮内酯化合物 |
| CN103384676B (zh) * | 2010-12-09 | 2016-02-03 | 沃克哈特有限公司 | 酮内酯化合物 |
| CN105669803A (zh) * | 2010-12-09 | 2016-06-15 | 沃克哈特有限公司 | 酮内酯化合物 |
| CN103619849A (zh) * | 2011-03-01 | 2014-03-05 | 沃克哈特有限公司 | 酮内酯中间体的制备方法 |
| 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 |
| CN103619863A (zh) * | 2011-03-22 | 2014-03-05 | 沃克哈特有限公司 | 酮内酯化合物的制备方法 |
| CN103619863B (zh) * | 2011-03-22 | 2016-03-16 | 沃克哈特有限公司 | 酮内酯化合物的制备方法 |
| WO2012163291A1 (zh) * | 2011-06-02 | 2012-12-06 | 广州翰鼎医药科技有限公司 | 用于抑制肿瘤转移和肿瘤血管生长的苯基哌嗪类衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2056844A4 (en) | 2010-11-24 |
| KR20090042971A (ko) | 2009-05-04 |
| US8097594B2 (en) | 2012-01-17 |
| WO2008023248A2 (en) | 2008-02-28 |
| CA2661538A1 (en) | 2008-02-28 |
| US20090247478A1 (en) | 2009-10-01 |
| EP2056844A2 (en) | 2009-05-13 |
| JP2010501541A (ja) | 2010-01-21 |
| WO2008023248A3 (en) | 2009-04-23 |
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Open date: 20090923 |