JP5785939B2 - オキサゾリジノン含有二量体化合物、組成物、ならびに作製および使用方法 - Google Patents
オキサゾリジノン含有二量体化合物、組成物、ならびに作製および使用方法 Download PDFInfo
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- JP5785939B2 JP5785939B2 JP2012513234A JP2012513234A JP5785939B2 JP 5785939 B2 JP5785939 B2 JP 5785939B2 JP 2012513234 A JP2012513234 A JP 2012513234A JP 2012513234 A JP2012513234 A JP 2012513234A JP 5785939 B2 JP5785939 B2 JP 5785939B2
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- QCGUSIANLFXSGE-GFCCVEGCSA-N C[n]1nnc(-c(cc2)ncc2-c(c(F)c2)ccc2N(C[C@H](COP(O)(O)=O)O2)C2=O)n1 Chemical compound C[n]1nnc(-c(cc2)ncc2-c(c(F)c2)ccc2N(C[C@H](COP(O)(O)=O)O2)C2=O)n1 QCGUSIANLFXSGE-GFCCVEGCSA-N 0.000 description 1
- XFALPSLJIHVRKE-GFCCVEGCSA-O C[n]1nnc(-c(cc2)ncc2-c(c(F)c2)ccc2N(C[C@H](C[OH2+])O2)C2=O)n1 Chemical compound C[n]1nnc(-c(cc2)ncc2-c(c(F)c2)ccc2N(C[C@H](C[OH2+])O2)C2=O)n1 XFALPSLJIHVRKE-GFCCVEGCSA-O 0.000 description 1
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- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
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Description
本出願は、参照により本明細書に組み込まれている米国仮出願第61/181,955号の優先権を主張するものである。
式中、nは、非負の整数であり、
各Zは、切断時にin vivoで抗生物質活性を有するオキサゾリジノン含有部分であり、
Mは、独立して、OR1またはNR1R2
(式中、R1およびR2は、独立して、H、1個もしくは複数のヘテロ原子を含有し得る場合により置換されたヒドロカルビル残基または薬学的に許容されるカチオンからなる群から選択される)
である。
式中、*は、ZのPへの結合点であり、
R1aおよびR1bは、独立してHおよびFから選択されるが、ただし、R1aおよびR1bの少なくとも一方はFであり、
Hetは、少なくとも1個のN、O、またはS原子を含む場合により置換された五または六員複素環である。
式中、nは、非負の整数であり、
Zは、切断時にin vivoで抗生物質活性を有するオキサゾリジノン含有部分であり、
Mは、独立して、OR1またはNR1R2
(式中、R1およびR2は、独立して、H、場合により置換されたヒドロカルビル残基または薬学的に許容されるカチオンからなる群から選択される)
である。
式中、*は、ZのPへの結合点であり、
R1aおよびR1bは、独立してHおよびFから選択されるが、ただし、R1aおよびR1bの少なくとも一方はFであり、
Hetは、テトラゾリルまたはオキサジアゾリルなどの、少なくとも1個のN、O、またはS原子を含む場合により置換された五または六員複素環である。
式II
(実施例)
この実施例および以下の実施例において、「式III」は、式中、Zが
実施例2〜5において、「式IV」は、式中、Zが
Balb/c雌マウス、6〜7週齢(約20g)を3匹の動物の処置群に無作為化した。試験化合物のそれぞれの薬物動態を評価した。尾静脈を介してまたは経口で試験化合物(10mg/kg)を試験マウスに投与した。5(静脈内投与した化合物のみ)、15、30分および1、4、6、8、12および24時間(各時点でn=3)の時点で、心臓穿刺により血液を採取した。有効なHPLC/UV法の使用を介して、式Ia、(実施例1に定義の)III、および(実施例2に定義の)IVの化合物のそれぞれの血漿濃度を分析した。データを図1および図2にプロットしている。
臨床検査標準協会(Clinical and Laboratory Standards Institute)(CLSI)が承認した方法(M7−A7)に従ってブロス微量希釈により最小阻止濃度を測定し、Alamar Blueを使用して可視化して細胞生存度を判断した。該化合物のそれぞれの希釈度を黄色ブドウ球菌(S. aureus)Smith株または黄色ブドウ球菌(S. aureus)+20%マウス血清に対して試験した。
Balb/c雌マウス、6〜7週齢(約20g)を10匹の動物の処置群に無作為化した。黄色ブドウ球菌(Staphylococcus aureus)Smith株ATCC#13709を、BHI培地において37℃で終夜培養した。細胞を1:10逆希釈し、5時間増殖させた。マウスを感染させるのに使用した菌種は、5%ブタ胃ムチン/PBS中の培養物を1×106cfu/mlの濃度まで希釈することにより用意した。段階希釈および培養物のプレーティングにより開始cfu/mlを求めるために100μlの培養物/ムチンを取っておいた。投薬の直前にマウスに500μlの菌種を感染させた。感染の15分以内に薬物を投与した。
Claims (14)
- R1は薬学的に許容されるカチオンである、
請求項1に記載の製剤または医薬組成物。 - R1がナトリウムカチオンである、請求項2に記載の製剤または医薬組成物。
- 薬学的に許容される担体、希釈剤または医薬品添加物をさらに含む、請求項1に記載の製剤または医薬組成物。
- R1がナトリウムカチオンである、請求項5に記載の製剤または医薬組成物。
- R1がHである、請求項5に記載の製剤または医薬組成物。
- 細菌感染症を治療するための請求項1から10のいずれかに記載の製剤または医薬組成物。
- リン酸化剤がPOCl3である、請求項12に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18195509P | 2009-05-28 | 2009-05-28 | |
US61/181,955 | 2009-05-28 | ||
US12/787,293 | 2010-05-25 | ||
US12/787,293 US8580767B2 (en) | 2009-05-28 | 2010-05-25 | Oxazolidinone containing dimer compounds, compositions and methods to make and use |
PCT/US2010/036283 WO2010138649A1 (en) | 2009-05-28 | 2010-05-27 | Oxazolidinone containing dimer compounds, compositions and methods to make and use |
Related Child Applications (1)
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JP2015147363A Division JP6010196B2 (ja) | 2009-05-28 | 2015-07-27 | オキサゾリジノン含有二量体化合物、組成物、ならびに作製および使用方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012528182A JP2012528182A (ja) | 2012-11-12 |
JP5785939B2 true JP5785939B2 (ja) | 2015-09-30 |
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JP2012513234A Expired - Fee Related JP5785939B2 (ja) | 2009-05-28 | 2010-05-27 | オキサゾリジノン含有二量体化合物、組成物、ならびに作製および使用方法 |
JP2015147363A Expired - Fee Related JP6010196B2 (ja) | 2009-05-28 | 2015-07-27 | オキサゾリジノン含有二量体化合物、組成物、ならびに作製および使用方法 |
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JP2015147363A Expired - Fee Related JP6010196B2 (ja) | 2009-05-28 | 2015-07-27 | オキサゾリジノン含有二量体化合物、組成物、ならびに作製および使用方法 |
Country Status (13)
Country | Link |
---|---|
US (2) | US8580767B2 (ja) |
EP (1) | EP2435051A1 (ja) |
JP (2) | JP5785939B2 (ja) |
KR (1) | KR101745511B1 (ja) |
CN (2) | CN103923122B (ja) |
AU (1) | AU2010254039B2 (ja) |
BR (1) | BRPI1012047A2 (ja) |
CA (1) | CA2769769A1 (ja) |
IL (2) | IL216547A0 (ja) |
MX (2) | MX2011012544A (ja) |
NZ (2) | NZ620552A (ja) |
RU (2) | RU2557910C2 (ja) |
WO (1) | WO2010138649A1 (ja) |
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KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
CN106220621B (zh) | 2008-10-10 | 2019-06-11 | 默沙东公司 | 制备噁唑烷酮类的方法及含有噁唑烷酮类的组合物 |
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CN111825666B (zh) * | 2019-04-23 | 2024-03-08 | 上海仕谱生物科技有限公司 | 二聚或多聚体形式的突变型idh抑制剂 |
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US8580767B2 (en) | 2009-05-28 | 2013-11-12 | Trius Therapeutics, Inc. | Oxazolidinone containing dimer compounds, compositions and methods to make and use |
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MX2011012544A (es) | 2012-02-28 |
RU2557910C2 (ru) | 2015-07-27 |
BRPI1012047A2 (pt) | 2019-09-24 |
JP2016026145A (ja) | 2016-02-12 |
AU2010254039A1 (en) | 2011-12-15 |
NZ596602A (en) | 2014-02-28 |
KR101745511B1 (ko) | 2017-06-20 |
EP2435051A1 (en) | 2012-04-04 |
IL239049A0 (en) | 2015-07-30 |
RU2015122032A (ru) | 2015-12-10 |
CN103923122B (zh) | 2016-08-24 |
CN102497866B (zh) | 2014-09-17 |
NZ620552A (en) | 2015-08-28 |
US8580767B2 (en) | 2013-11-12 |
AU2010254039B2 (en) | 2016-03-03 |
JP2012528182A (ja) | 2012-11-12 |
IL239049A (en) | 2017-07-31 |
US20140057874A1 (en) | 2014-02-27 |
CN103923122A (zh) | 2014-07-16 |
IL216547A0 (en) | 2012-02-29 |
JP6010196B2 (ja) | 2016-10-19 |
CA2769769A1 (en) | 2010-12-02 |
CN102497866A (zh) | 2012-06-13 |
KR20120026568A (ko) | 2012-03-19 |
WO2010138649A1 (en) | 2010-12-02 |
US20100305069A1 (en) | 2010-12-02 |
MX2014001282A (es) | 2014-06-10 |
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