JP2011528354A - 抗生物質 - Google Patents
抗生物質 Download PDFInfo
- Publication number
- JP2011528354A JP2011528354A JP2011518807A JP2011518807A JP2011528354A JP 2011528354 A JP2011528354 A JP 2011528354A JP 2011518807 A JP2011518807 A JP 2011518807A JP 2011518807 A JP2011518807 A JP 2011518807A JP 2011528354 A JP2011528354 A JP 2011528354A
- Authority
- JP
- Japan
- Prior art keywords
- malic acid
- resistant
- oxo
- acid
- cyclopropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003242 anti bacterial agent Substances 0.000 title description 2
- 229940088710 antibiotic agent Drugs 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 18
- AVPQPGFLVZTJOR-NEPJUHHUSA-N 7-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2C[C@@H](N)C[C@@H](C)C2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 AVPQPGFLVZTJOR-NEPJUHHUSA-N 0.000 claims abstract description 13
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 13
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 57
- 229940049920 malate Drugs 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 31
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 19
- 241000191967 Staphylococcus aureus Species 0.000 claims description 18
- 235000011090 malic acid Nutrition 0.000 claims description 18
- 241000193998 Streptococcus pneumoniae Species 0.000 claims description 15
- 208000015181 infectious disease Diseases 0.000 claims description 13
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 13
- 239000001630 malic acid Substances 0.000 claims description 12
- 229940099690 malic acid Drugs 0.000 claims description 12
- 241000194032 Enterococcus faecalis Species 0.000 claims description 10
- 241000606768 Haemophilus influenzae Species 0.000 claims description 9
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 9
- 241000588652 Neisseria gonorrhoeae Species 0.000 claims description 9
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- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 claims description 3
- 108010059993 Vancomycin Proteins 0.000 claims description 3
- 229940116298 l- malic acid Drugs 0.000 claims description 3
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- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 239000000796 flavoring agent Substances 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007919 intrasynovial administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960003376 levofloxacin Drugs 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 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 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8080908P | 2008-07-15 | 2008-07-15 | |
| US61/080,809 | 2008-07-15 | ||
| PCT/US2009/050241 WO2010009014A2 (en) | 2008-07-15 | 2009-07-10 | Antibiotic drug |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011528354A true JP2011528354A (ja) | 2011-11-17 |
| JP2011528354A5 JP2011528354A5 (enExample) | 2012-08-09 |
Family
ID=41550976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011518807A Withdrawn JP2011528354A (ja) | 2008-07-15 | 2009-07-10 | 抗生物質 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20120157492A1 (enExample) |
| JP (1) | JP2011528354A (enExample) |
| KR (1) | KR20110050623A (enExample) |
| CN (1) | CN101628911B (enExample) |
| TW (1) | TW201008567A (enExample) |
| WO (1) | WO2010009014A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0709220A2 (pt) | 2006-03-28 | 2011-07-12 | Procter & Gamble | processo de acoplamento para preparo de intermediários de quinolona |
| WO2010002415A1 (en) * | 2008-07-01 | 2010-01-07 | Taigen Biotechnology Co., Ltd. | Treatment of antibiotic-resistant bacteria infection |
| CN103145615B (zh) * | 2013-03-20 | 2015-07-29 | 浙江医药股份有限公司 | 一种奈诺沙星螯合物的后处理方法 |
| CA2920791C (en) | 2013-10-14 | 2021-11-16 | Eisai R&D Management Co., Ltd. | Selectively substituted quinoline compounds |
| CN106336371A (zh) * | 2016-08-16 | 2017-01-18 | 成都百事兴科技实业有限公司 | 叔丁氧羰基‑l‑焦谷氨酸甲酯的合成方法 |
| CN113640416A (zh) * | 2021-08-12 | 2021-11-12 | 海南海神同洲制药有限公司 | 盐酸左氧氟沙星片的含量测定方法 |
| CN116785271A (zh) * | 2023-07-13 | 2023-09-22 | 河南农业大学 | 苹果酸及其衍生物在制备金属-β-内酰胺酶增敏剂中的应用、组合物和其应用 |
| CN118852222B (zh) * | 2024-06-27 | 2025-09-05 | 南京桦冠生物技术有限公司 | 一种奈诺沙星中间体及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1015445B1 (en) * | 1997-09-15 | 2009-02-25 | The Procter & Gamble Company | Antimicrobial quinolones, their compositions and uses |
| JP4876165B2 (ja) * | 2006-03-28 | 2012-02-15 | ザ プロクター アンド ギャンブル カンパニー | キノロン中間体を調製するための水素化物還元法 |
-
2009
- 2009-07-10 US US12/500,952 patent/US20120157492A1/en not_active Abandoned
- 2009-07-10 WO PCT/US2009/050241 patent/WO2010009014A2/en not_active Ceased
- 2009-07-10 KR KR1020117001200A patent/KR20110050623A/ko not_active Withdrawn
- 2009-07-10 JP JP2011518807A patent/JP2011528354A/ja not_active Withdrawn
- 2009-07-14 TW TW098123739A patent/TW201008567A/zh unknown
- 2009-07-14 CN CN2009101604652A patent/CN101628911B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| HK1139132A1 (en) | 2010-09-10 |
| KR20110050623A (ko) | 2011-05-16 |
| CN101628911A (zh) | 2010-01-20 |
| US20120157492A1 (en) | 2012-06-21 |
| TW201008567A (en) | 2010-03-01 |
| WO2010009014A3 (en) | 2010-04-29 |
| CN101628911B (zh) | 2013-05-29 |
| WO2010009014A2 (en) | 2010-01-21 |
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