JP2015515998A - （ｒ）−ニフラテル、感染を治療するためのその使用ならびに（ｒ）および（ｓ）−ニフラテルの合成 - Google Patents

（ｒ）−ニフラテル、感染を治療するためのその使用ならびに（ｒ）および（ｓ）−ニフラテルの合成 Download PDF

Info

Publication number
JP2015515998A
JP2015515998A JP2015510685A JP2015510685A JP2015515998A JP 2015515998 A JP2015515998 A JP 2015515998A JP 2015510685 A JP2015510685 A JP 2015510685A JP 2015510685 A JP2015510685 A JP 2015510685A JP 2015515998 A JP2015515998 A JP 2015515998A
Authority
JP
Japan
Prior art keywords
compound
nifratel
carried out
steps
solvent
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.)
Pending
Application number
JP2015510685A
Other languages
English (en)
Japanese (ja)
Inventor
ガグリアルディ ステファニア
ガグリアルディ ステファニア
コンソンニ アレッサンドラ
コンソンニ アレッサンドラ
メラン フェデリコ
メラン フェデリコ
ブルゲローニ アンナ
ブルゲローニ アンナ
Original Assignee
ポリケム・エスエイ
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=47846051&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JP2015515998(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by ポリケム・エスエイ filed Critical ポリケム・エスエイ
Publication of JP2015515998A publication Critical patent/JP2015515998A/ja
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C241/02—Preparation of hydrazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Gynecology & Obstetrics (AREA)
  • Urology & Nephrology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2015510685A 2012-05-11 2013-03-13 （ｒ）−ニフラテル、感染を治療するためのその使用ならびに（ｒ）および（ｓ）−ニフラテルの合成 Pending JP2015515998A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12167640.7 2012-05-11
EP20120167640 EP2662371A1 (en) 2012-05-11 2012-05-11 (R)-Nifuratel and synthesis of (R) and (S)-Nifuratel
PCT/EP2013/055078 WO2013167295A1 (en) 2012-05-11 2013-03-13 (r) -nifuratel, its use for the treatment of infections and synthesis of (r) and (s) -nifuratel

Publications (1)

Publication Number Publication Date
JP2015515998A true JP2015515998A (ja) 2015-06-04

Family

ID=47846051

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2015510685A Pending JP2015515998A (ja) 2012-05-11 2013-03-13 （ｒ）−ニフラテル、感染を治療するためのその使用ならびに（ｒ）および（ｓ）−ニフラテルの合成

Country Status (27)

Country Link
US (2) US9284306B2 (enExample)
EP (2) EP2662371A1 (enExample)
JP (1) JP2015515998A (enExample)
KR (1) KR20150008871A (enExample)
CN (1) CN104379580A (enExample)
AU (1) AU2013258385A1 (enExample)
BR (1) BR112014027953A2 (enExample)
CA (1) CA2869827A1 (enExample)
CL (1) CL2014002951A1 (enExample)
CO (1) CO7131368A2 (enExample)
CR (1) CR20140505A (enExample)
DO (1) DOP2014000252A (enExample)
EA (1) EA201492081A1 (enExample)
EC (1) ECSP14026432A (enExample)
GE (2) GEP201606595B (enExample)
HK (1) HK1202539A1 (enExample)
IL (1) IL235429A0 (enExample)
IN (1) IN2014DN09256A (enExample)
MA (1) MA20150279A1 (enExample)
MX (1) MX2014013759A (enExample)
NZ (1) NZ700752A (enExample)
PE (1) PE20150167A1 (enExample)
PH (2) PH12014502500B1 (enExample)
SG (2) SG11201406447SA (enExample)
TN (1) TN2014000430A1 (enExample)
WO (1) WO2013167295A1 (enExample)
ZA (1) ZA201407596B (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108254453A (zh) * 2016-12-28 2018-07-06 苏州电器科学研究院股份有限公司 一种有效测定塑料制品中邻苯二甲酸酯含量的检测方法
US10301319B2 (en) 2017-09-20 2019-05-28 Ph Pharma Co., Ltd. Thailanstatin analogs
CN108760950B (zh) * 2018-04-25 2022-07-15 国检测试控股集团京诚检测有限公司 一种测定硝基呋喃代谢物的方法
CN111892557B (zh) * 2019-05-05 2022-11-08 河北圣泰材料股份有限公司 哌嗪类成膜离子液体的合成方法
CN110672765B (zh) * 2019-10-11 2022-03-18 温州海鹤药业有限公司 一种定量检测硝呋太尔中顺式异构体杂质的方法
CN112457304B (zh) * 2020-12-07 2022-03-11 中国药科大学 一种硝呋太尔的制备方法
CN113828243B (zh) * 2021-09-14 2022-06-28 南京南大药业有限责任公司 一种硝呋太尔制霉菌素栓制造方法及设备
WO2024220546A2 (en) 2023-04-17 2024-10-24 Peak Bio, Inc. Antibodies and antibody-drug conjugates and methods of use and synthetic processes and intermediates
CN116947838B (zh) * 2023-07-25 2025-08-19 北京金城泰尔制药有限公司沧州分公司 高纯度硝呋太尔的生产方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB969126A (en) * 1962-08-01 1964-09-09 Polichimica Sap S P A Substituted oxazolidinones
CN101037435A (zh) * 2006-03-16 2007-09-19 韩志强 (s)－硝呋太尔,其制备方法和应用
WO2010121980A1 (en) * 2009-04-20 2010-10-28 Polichem S.A. Use of nifuratel to treat infections caused by atopobium species

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100516063C (zh) * 2006-03-16 2009-07-22 韩志强 硝呋太尔的生产方法
CN101434584A (zh) * 2007-11-15 2009-05-20 中山大学 具有抗菌活性的手性噁唑烷酮类化合物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB969126A (en) * 1962-08-01 1964-09-09 Polichimica Sap S P A Substituted oxazolidinones
CN101037435A (zh) * 2006-03-16 2007-09-19 韩志强 (s)－硝呋太尔,其制备方法和应用
WO2010121980A1 (en) * 2009-04-20 2010-10-28 Polichem S.A. Use of nifuratel to treat infections caused by atopobium species

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
JPN6016023822; Ｈａｏ，　Ｊｉｎｈｅｎｇ　ｅｔ　ａｌ．: 'Ｓｙｎｔｈｅｓｉｓ　ａｎｄ　ａｎｔｉｂａｃｔｅｒｉａｌ　ａｃｔｉｖｉｔｉｅｓ　ｏｆ　ｎｅｗ　ｏｘａｚｏｌｉｄｉｎｏｎｅ　ｄｅｒｉｖａｔｉｖｅｓ' Ｚｈｏｎｇｇｕｏ　Ｙａｏｗｕ　Ｈｕａｘｕｅ　Ｚａｚｈｉ Ｖｏｌ．１５（２）, 2005, ｐｐ．７６-７９，　８４ *
JPN6016023824; Ｚｈａｉ，　Ｘｉｎ；　Ｈｏｎｇ，　Ｗｅｉ；　Ｘｉｏｎｇ，　Ｙｉｎｇ；　Ｇｏｎｇ，　Ｐｉｎｇ: 'Ｓｙｎｔｈｅｓｉｓ　ａｎｄ　ａｎｔｉｂａｃｔｅｒｉａｌ　ａｃｔｉｖｉｔｉｅｓ　ｏｆ　ｎｅｗ　ｏｘａｚｏｌｉｄｉｎｏｎｅ　ｄｅｒｉｖａｔｉｖｅｓ' Ｚｈｏｎｇｇｕｏ　Ｙａｏｗｕ　Ｈｕａｘｕｅ　Ｚａｚｈｉ Ｖｏｌ．１４（５）, 2004, ｐｐ．２６３-２６６ *
JPN6016023826; Ｄｅｎｉｓ，　Ａ．；　Ｖｉｌｌｅｔｔｅ，　Ｔ．: '５-ａｒｙｌ-beta，gamma　ｂｕｔｅｎｏｌｉｄｅ，　ａ　ｎｅｗ　ｃｌａｓｓ　ｏｆ　ａｎｔｉｂａｃｔｅｒｉａｌ　ｄｅｒｉｖｅｄｆｒｏｍ　ｔｈｅ　Ｎ-ａｒｙｌｏｘａｚｏｌｉｄｉｎｏｎｅ　ＤＵＰ　７２１' Ｂｉｏｏｒｇａｎｉｃ　＆　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ　Ｌｅｔｔｅｒｓ Ｖｏｌ．４，　Ｎｏ．１６, 1994, ｐｐ．１９２５-３０ *
JPN6016023829; Ｂｒｕｎｏ， Ｏｌｇａ； Ｂｏｎｄａｖａｌｌｉ ｅｔ ａｌ．: '３，５-Ｄｉｐｈｅｎｙｌ-１Ｈ-ｐｙｒａｚｏｌｅ ｄｅｒｉｖａｔｉｖｅｓ． ＶＩＩ - Ｅｓｔｅｒｓ， ２-ｄｉａｌｋｙｌａｍｉｎｏｅｔｈｙｌ ｅｔｈｅｒｓ ａｎｄ Ｎ-ｓｕｂｓｔｉｔｕｔｅｄ ｃａ' Ｆａｒｍａｃｏ Ｖｏｌ．４５（５）, 1990, ｐｐ．５２７-４３ *
JPN6016023832; Ｒｕｄｒａ，　Ｓｏｎａｌｉ　ｅｔ　ａｌ．: 'Ｓｙｎｔｈｅｓｉｓ　ａｎｄ　ａｎｔｉｂａｃｔｅｒｉａｌ　ａｃｔｉｖｉｔｙ　ｏｆ　ｎｏｖｅｌ　ｏｘａｚｏｌｉｄｉｎｏｎｅｓ　ｗｉｔｈ　ｍｅｔｈｙｌｅｎｅ　ｏｘｙｇｅｎ-　ａｎｄ　ｍｅｔｈｙｌｅｎｅ　ｓｕ' Ｂｉｏｏｒｇａｎｉｃ　＆　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ　Ｌｅｔｔｅｒｓ Ｖｏｌ．１７（１７）, 2007, ｐｐ．４７７８-４７８３ *
JPN6016023833; Ｃｒｉｍｍｉｎｓ，　Ｍｉｃｈａｅｌ　Ｔ．；　Ｄｉａｚ，　Ｃａｒｏｌｉｎｅ　Ｊ．；　Ｅｍｍｉｔｔｅ，　Ｋｙｌｅ　Ａ．: 'Ａ　ｕｎｉｆｉｅｄ　ａｐｐｒｏａｃｈ　ｔｏ　ｔｈｅ　ｅｎａｎｔｉｏｓｅｌｅｃｔｉｖｅ　ｓｙｎｔｈｅｓｉｓ　ｏｆ　２，６-ｃｉｓ-　ａｎｄ　ｔｒａｎｓ-ｄｉｓｕｂｓｔｉｔｕｔｅｄ　ｔｅｔｒａｈｙｄｒｏｐ' Ｈｅｔｅｒｏｃｙｃｌｅｓ Ｖｏｌ．６２, 2004, ｐｐ．１７９-１８３ *

Also Published As

Publication number Publication date
WO2013167295A1 (en) 2013-11-14
NZ700752A (en) 2016-02-26
PH12014502500A1 (en) 2014-12-15
ECSP14026432A (es) 2015-09-30
SG11201406447SA (en) 2014-11-27
PE20150167A1 (es) 2015-02-07
TN2014000430A1 (en) 2016-03-30
EA201492081A1 (ru) 2015-06-30
BR112014027953A2 (pt) 2018-02-06
DOP2014000252A (es) 2014-12-31
IN2014DN09256A (enExample) 2015-07-10
US20150148547A1 (en) 2015-05-28
ZA201407596B (en) 2016-05-25
US20150119431A1 (en) 2015-04-30
EP2662371A1 (en) 2013-11-13
CN104379580A (zh) 2015-02-25
US9284306B2 (en) 2016-03-15
MA20150279A1 (fr) 2015-08-31
PH12014502500B1 (en) 2014-12-15
GEP201706626B (en) 2017-02-10
GEP201606595B (en) 2017-01-10
CA2869827A1 (en) 2013-11-14
SG10201608485XA (en) 2016-12-29
CR20140505A (es) 2015-02-06
MX2014013759A (es) 2015-08-07
AU2013258385A1 (en) 2014-10-30
PH12015502241A1 (en) 2016-08-15
CO7131368A2 (es) 2014-12-01
HK1202539A1 (en) 2015-10-02
US9067927B2 (en) 2015-06-30
CL2014002951A1 (es) 2014-12-26
KR20150008871A (ko) 2015-01-23
EP2847189A1 (en) 2015-03-18
IL235429A0 (en) 2014-12-31

Similar Documents

Publication Publication Date Title
JP2015515998A (ja) （ｒ）−ニフラテル、感染を治療するためのその使用ならびに（ｒ）および（ｓ）−ニフラテルの合成
JP2020007327A (ja) 癌の治療のためのｅｒｂｂチロシンキナーゼ阻害剤としてのベンゾイミダゾール誘導体
KR19990072109A (ko) 4-피리미디닐- 또는 4-피라지닐-피페라지닐-페닐-옥사졸리디논유도체, 그의 제조방법 및 그의 항균제로서의 용도
IE58325B1 (en) Aminomethyl oxooxazolidinyl benzene Derivatives useful as antibacterial agents
RU2215740C2 (ru) Оксазолидиноновые производные и фармацевтические композиции на их основе
JPH09502436A (ja) 置換オキサジンおよびチアジンオキサゾリジノン抗微生物剤
JP2000500489A (ja) 三環置換基を有するオキサゾリジノン抗菌剤
US11332477B2 (en) Nitrogen containing heterocycle substituted benzoxazine oxazolidinone compound and preparation method and use thereof
EP3164393B1 (fr) Dérivés de flavaglines
WO2018149359A1 (zh) 三氮唑抗菌衍生物、其药物组合物和用途
TW470742B (en) Benzimidazole derivatives, preparation and pharmaceutical compositions thereof
RU2527165C2 (ru) 2, 5-дизамещенные арилсульфонамидные антагонисты ссr3
CN107033186B (zh) 泊沙康唑衍生物、其药物组合物和用途
JP7222909B2 (ja) （ｓ）－アフォキソラネルの結晶形
CN105189513A (zh) 葡萄糖醇，1-脱氧-1-(甲胺基)-,1-(6-氨基-3,5-二氟吡啶-2-基)-8-氯-6-氟-1,4-二氢-7-(3-羟基氮杂环丁烷-l-基)-4-氧-3-喹啉羧酸盐的结晶形态
US20080275035A1 (en) Nitroimidazole Compounds
TWI473793B (zh) 芳基磺醯胺ｃｃｒ３拮抗劑
JP5662940B2 (ja) 新規な抗微生物薬
KR20050055793A (ko) 항미생물제로서의엔-설포닐-4-메틸렌아미노-3-하이드록시-2-피리돈
JP5934647B2 (ja) クロストリジウム・ディフィシル感染症のための選択的抗菌薬
TW202245746A (zh) Ｎ－（（ｒ）－２，３－二羥基丙氧基）—３，４—二氟—２—（２—氟—４—碘—苯基胺基)—苯甲醯胺之基本上純的形式ｉｖ之組合物及其用途
CN1671725A (zh) 新的无定形9－脱氧－9a－氮杂－9a－甲基－9a－高红霉素a、其制备方法和应用
CN101341150A (zh) 硝基咪唑化合物
US10870646B2 (en) Oxazolidinones and pharmaceutical compositions thereof for treating bacterial infections, including infection of Mycobacterium tuberculosis
US9657037B2 (en) Pyrrole compounds with silicon incorporation

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20141218

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20150924

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20160519

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20160628

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20160928

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20170207