CA2287219C - 2-oxo-1-azetidine sulfonic acid derivatives as potent .beta.-lactamase inhibitors - Google Patents

2-oxo-1-azetidine sulfonic acid derivatives as potent .beta.-lactamase inhibitors Download PDF

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Publication number
CA2287219C
CA2287219C CA002287219A CA2287219A CA2287219C CA 2287219 C CA2287219 C CA 2287219C CA 002287219 A CA002287219 A CA 002287219A CA 2287219 A CA2287219 A CA 2287219A CA 2287219 C CA2287219 C CA 2287219C
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CA
Canada
Prior art keywords
compound
beta
pharmaceutically acceptable
group
formula
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.)
Expired - Fee Related
Application number
CA002287219A
Other languages
English (en)
French (fr)
Other versions
CA2287219A1 (en
Inventor
Samarendra N. Maiti
Eduardo L. Setti
Oludotun A. Phillips
Andhe V. Narender Reddy
Ronald George Micetich
Rajeshwar Singh
Fusahiro Higashitani
Chieko Kunugita
Koichi Nishida
Tatsuya Uji
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Naeja Pharmaceutical Inc
Taiho Pharmaceutical Co Ltd
Original Assignee
Naeja Pharmaceutical Inc
Taiho Pharmaceutical Co Ltd
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
Application filed by Naeja Pharmaceutical Inc, Taiho Pharmaceutical Co Ltd filed Critical Naeja Pharmaceutical Inc
Publication of CA2287219A1 publication Critical patent/CA2287219A1/en
Application granted granted Critical
Publication of CA2287219C publication Critical patent/CA2287219C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D419/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • 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)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA002287219A 1997-04-24 1998-04-23 2-oxo-1-azetidine sulfonic acid derivatives as potent .beta.-lactamase inhibitors Expired - Fee Related CA2287219C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/840,608 US5888998A (en) 1997-04-24 1997-04-24 2-oxo-1-azetidine sulfonic acid derivatives as potent β-lactamase inhibitors
US08/840,608 1997-04-24
PCT/IB1998/000622 WO1998047895A1 (en) 1997-04-24 1998-04-23 2-OXO-1-AZETIDINE SULFONIC ACID DERIVATIVES AS POTENT β-LACTAMASE INHIBITORS

Publications (2)

Publication Number Publication Date
CA2287219A1 CA2287219A1 (en) 1998-10-29
CA2287219C true CA2287219C (en) 2010-01-12

Family

ID=25282793

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002287219A Expired - Fee Related CA2287219C (en) 1997-04-24 1998-04-23 2-oxo-1-azetidine sulfonic acid derivatives as potent .beta.-lactamase inhibitors

Country Status (10)

Country Link
US (1) US5888998A (enExample)
EP (1) EP0979229B1 (enExample)
JP (1) JP2001521549A (enExample)
KR (1) KR20010020181A (enExample)
AU (1) AU740446B2 (enExample)
CA (1) CA2287219C (enExample)
DE (1) DE69808901T2 (enExample)
HU (1) HUP0001269A3 (enExample)
NO (1) NO995108L (enExample)
WO (1) WO1998047895A1 (enExample)

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KR20010002705A (ko) * 1999-06-17 2001-01-15 고두모 신규 티아졸 초산의 반응성 포스페이트 유도체의 제조방법
DE60111757T2 (de) * 2000-09-14 2006-04-27 Pantherix Ltd. 3-(Heteroarylacetamido)-2-oxoazetidin-1-sulfonsäure-derivate als antibakterielle Mittel
ES2373461T3 (es) * 2005-12-07 2012-02-03 Basilea Pharmaceutica Ag Antibióticos útiles de monobactama.
RU2488394C2 (ru) * 2007-03-23 2013-07-27 Базилеа Фармацойтика Аг Комбинированные лекарственные средства для лечения бактериальных инфекций
RU2599791C2 (ru) 2010-08-10 2016-10-20 Ремпекс Фармасьютикэлз, Инч. Циклические бороновые кислотно-эфирные производные и их использование в терапии
US8806158B2 (en) 2010-09-22 2014-08-12 International Business Machines Corporation Intelligent computer memory management
WO2013033461A1 (en) 2011-08-31 2013-03-07 Rempex Pharmaceuticals, Inc. Heterocyclic boronic acid ester derivatives and therapeutic uses thereof
US9156858B2 (en) 2012-05-23 2015-10-13 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US10561675B2 (en) 2012-06-06 2020-02-18 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
CN103435650B (zh) * 2012-12-28 2015-12-02 南京海融医药科技有限公司 单环β-内酰胺类化合物、制备方法及其制药用途
WO2014107535A1 (en) 2013-01-04 2014-07-10 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9101638B2 (en) 2013-01-04 2015-08-11 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US9241947B2 (en) 2013-01-04 2016-01-26 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
MX2015008627A (es) 2013-01-04 2015-09-23 Rempex Pharmaceuticals Inc Derivados de acido boronico y usos terapeuticos de los mismos.
US9687497B1 (en) 2014-05-05 2017-06-27 Rempex Pharmaceuticals, Inc. Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof
EP3140310B1 (en) 2014-05-05 2019-08-07 Rempex Pharmaceuticals, Inc. Synthesis of boronate salts and uses thereof
MX2016015093A (es) 2014-05-19 2017-03-27 Rempex Pharmaceuticals Inc Derivados de acido boronico y sus usos terapeuticos.
KR20170024087A (ko) 2014-07-01 2017-03-06 렘펙스 파머수티클스 인코퍼레이티드 보론산 유도체 및 그의 치료적 용도
US10662205B2 (en) 2014-11-18 2020-05-26 Qpex Biopharma, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
EP3233869B1 (en) 2014-12-19 2019-09-25 Rempex Pharmaceuticals, Inc. Apparatus and continuous flow process for production of boronic acid derivatives
WO2016149393A1 (en) 2015-03-17 2016-09-22 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
RU2618433C2 (ru) * 2015-08-10 2017-05-03 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Санкт-Петербургский государственный университет" (СПбГУ) Антимикробная комбинация в отношении устойчивых к карбапенемам грамотрицательных бактерий вида pseudomonas aeruginosa, продуцирующих металло-β-лактамазу
EP3478693B1 (en) 2016-06-30 2021-07-21 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
CN107641119B (zh) * 2016-07-21 2019-11-08 中国科学院上海药物研究所 单环β-内酰胺-铁载体轭合物及其制备方法和用途
RU2664434C2 (ru) * 2016-12-01 2018-08-17 Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет" (СПбГУ) АНТИМИКРОБНАЯ КОМБИНАЦИЯ В ОТНОШЕНИИ УСТОЙЧИВЫХ К КАРБАПЕНЕМАМ ГРАМОТРИЦАТЕЛЬНЫХ БАКТЕРИЙ ВИДА KLEBSIELLA PNEUMONIAE, ПРОДУЦИРУЮЩИХ МЕТАЛЛО-β-ЛАКТАМАЗУ
RU2666619C2 (ru) * 2016-12-01 2018-09-11 Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет" (СПбГУ) АНТИМИКРОБНАЯ КОМБИНАЦИЯ В ОТНОШЕНИИ УСТОЙЧИВЫХ К КАРБАПЕНЕМАМ ГРАМОТРИЦАТЕЛЬНЫХ БАКТЕРИЙ ВИДА ACINETOBACTER BAUMANNII, ПРОДУЦИРУЮЩИХ МЕТАЛЛО-β-ЛАКТАМАЗУ
CN111212843B (zh) 2017-10-11 2025-05-16 Qpex生物制药有限公司 硼酸衍生物及其合成
JP7329260B2 (ja) 2018-04-20 2023-08-18 キューペックス バイオファーマ, インコーポレイテッド ボロン酸誘導体およびその治療的使用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4775670A (en) * 1980-09-29 1988-10-04 E. R. Squibb & Sons, Inc. 2-oxo-1-azetidinesulfonic acid salts
US4632985A (en) * 1985-06-03 1986-12-30 E. R. Squibb & Sons, Inc. 3-acylamino-2-oxo-1-azetidinesulfonic acids
US5006650A (en) * 1987-02-11 1991-04-09 The Upjohn Company Novel N-1 substituted beta-lactams as antibiotics
EP0357604A1 (en) * 1987-02-27 1990-03-14 The Upjohn Company Antibiotic beta-lactams containing a pyridone carboxylic acid or acid derivative
US5112968A (en) * 1989-07-28 1992-05-12 E. R. Squibb & Sons, Inc. Monobactam hydrazide derivatives
CA2024282A1 (en) * 1989-09-21 1991-03-22 Peter H. Ermann Heterocyclic hydrazide derivatives of monocyclic beta-lactam antibiotics
ZA918014B (en) * 1990-11-05 1992-07-29 Squibb & Sons Inc Heteroaroyl derivatives of monocyclic beta-lactam antibiotics

Also Published As

Publication number Publication date
HUP0001269A3 (en) 2001-11-28
HUP0001269A2 (hu) 2001-05-28
DE69808901D1 (de) 2002-11-28
AU6931498A (en) 1998-11-13
KR20010020181A (ko) 2001-03-15
EP0979229B1 (en) 2002-10-23
CA2287219A1 (en) 1998-10-29
NO995108D0 (no) 1999-10-20
EP0979229A1 (en) 2000-02-16
US5888998A (en) 1999-03-30
AU740446B2 (en) 2001-11-01
DE69808901T2 (de) 2003-07-31
WO1998047895A1 (en) 1998-10-29
NO995108L (no) 1999-10-20
JP2001521549A (ja) 2001-11-06

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