CA2802529C - Carbapenem antibacterials with gram-negative activity - Google Patents

Carbapenem antibacterials with gram-negative activity Download PDF

Info

Publication number
CA2802529C
CA2802529C CA2802529A CA2802529A CA2802529C CA 2802529 C CA2802529 C CA 2802529C CA 2802529 A CA2802529 A CA 2802529A CA 2802529 A CA2802529 A CA 2802529A CA 2802529 C CA2802529 C CA 2802529C
Authority
CA
Canada
Prior art keywords
alkyl
compound
nrr
independently selected
pharmaceutically acceptable
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.)
Active
Application number
CA2802529A
Other languages
English (en)
French (fr)
Other versions
CA2802529A1 (en
Inventor
Woo-Baeg Choi
Deog-Il Kim
Ewa Gruszecka-Kowalik
Hyung-Yeul Joo
Shuangpei Liu
Shuli Mao
Yongfeng Li
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.)
FOB Synthesis Inc
Original Assignee
FOB Synthesis Inc
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 FOB Synthesis Inc filed Critical FOB Synthesis Inc
Publication of CA2802529A1 publication Critical patent/CA2802529A1/en
Application granted granted Critical
Publication of CA2802529C publication Critical patent/CA2802529C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/14—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2802529A 2010-06-18 2011-06-17 Carbapenem antibacterials with gram-negative activity Active CA2802529C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US35639810P 2010-06-18 2010-06-18
US61/356,398 2010-06-18
PCT/US2011/040883 WO2011160020A2 (en) 2010-06-18 2011-06-17 Carbapenem antibacterials with gram-negative activity

Publications (2)

Publication Number Publication Date
CA2802529A1 CA2802529A1 (en) 2011-12-22
CA2802529C true CA2802529C (en) 2019-10-29

Family

ID=45348895

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2802529A Active CA2802529C (en) 2010-06-18 2011-06-17 Carbapenem antibacterials with gram-negative activity

Country Status (8)

Country Link
US (2) US9149461B2 (enExample)
EP (1) EP2590978B1 (enExample)
JP (1) JP5922110B2 (enExample)
KR (1) KR101862041B1 (enExample)
CA (1) CA2802529C (enExample)
DK (1) DK2590978T3 (enExample)
ES (1) ES2653837T3 (enExample)
WO (1) WO2011160020A2 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2013203774A1 (en) 2012-01-27 2013-08-15 Los Angeles Biomedical Research Institute At Harbor-Ucla Medical Center Compositions and methods for immunization against bacteria expressing a carbapenemase
GB2529738B (en) * 2014-03-27 2018-10-17 Johnson Matthey Plc Process for preparing a carbapenem antibiotic
JP2017061430A (ja) * 2015-09-25 2017-03-30 芳男 ▲浜▼田 新規なプロドラッグ
US9751894B2 (en) * 2015-12-10 2017-09-05 Naeja-Rgm Pharmaceuticals Inc. Cephem compounds, their production and use
KR101798840B1 (ko) 2017-05-17 2017-11-17 주식회사 레고켐 바이오사이언스 신규 오토탁신 저해 화합물 및 이를 함유하는 약제학적 조성물
KR102694317B1 (ko) * 2017-06-09 2024-08-09 포브 신서시스 인코포레이티드 세균 감염의 치료를 위한 카바페넴 화합물 및 조성물
WO2019197468A1 (en) * 2018-04-12 2019-10-17 Bayer Aktiengesellschaft N-(cyclopropylmethyl)-5-(methylsulfonyl)-n-{1-[1-(pyrimidin-2-yl)-1h-1,2,4-triazol-5-yl]ethyl}benzamide derivatives and the corresponding pyridine-carboxamide derivatives as pesticides
CN109851542A (zh) * 2019-01-28 2019-06-07 爱斯特(成都)生物制药股份有限公司 一种(s)-n-甲基-n-(吡咯烷-3-基)乙酰胺二盐酸盐及其合成方法
CN111763170B (zh) * 2020-07-10 2022-03-18 江苏豪森药业集团有限公司 氟马替尼中间体的制备方法

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3950357A (en) 1974-11-25 1976-04-13 Merck & Co., Inc. Antibiotics
US4424230A (en) 1977-10-19 1984-01-03 Merck & Co., Inc. 6-(1'-Hydroxyethyl)-3-substituted amino-1-azabicyclo- 3.2.0!hept-2-en-7-one-2-carboxylic acid
EP0082133A3 (en) 1979-04-19 1983-07-20 Merck & Co. Inc. A process for preparing intermediates useful for preparing 2-substituted-6-substituted-1-carbadethiapen-2-em-3-carboxylic acids
EP0048116A1 (en) 1980-09-04 1982-03-24 The Rank Organisation Limited Moving coil loudspeaker
CA1283906C (en) 1983-05-09 1991-05-07 Makoto Sunagawa .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF
DE3579888D1 (de) 1984-11-08 1990-10-31 Sumitomo Pharma Carbapenemverbindungen und deren herstellung.
US4680292A (en) * 1984-12-13 1987-07-14 Merck & Co., Inc. Carbapenems and 1-methylcarbapenems having a 2-heteroaryliumaliphatic substituent
EP0184844A1 (en) 1984-12-13 1986-06-18 Merck & Co. Inc. 1-Methylcarbapenems having a 2-position substituent joined through an alkylenethio bridge
US4782051A (en) * 1985-06-10 1988-11-01 Merck & Co., Inc. 2-aza-substituted 1-carbadethiapen-2-em-3 carboxylic acids
EP0208889A1 (en) * 1985-06-10 1987-01-21 Merck & Co. Inc. 2-Aza-substituted 1-carbadethiapen-2-EM-3-carboxylic acids
US4866171A (en) 1987-04-11 1989-09-12 Lederle (Japan), Ltd. (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)]thio-6-[R-1-hydroxyethyl]-1-methyl-carbapenum-3-carboxylate
EP0292191A1 (en) 1987-05-21 1988-11-23 Merck & Co. Inc. 2-(Substituted methyl)-1-alkylcarbapenem derivatives
US4925838A (en) 1988-03-18 1990-05-15 Fujisawa Pharmaceutical Company, Ltd. 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds
US5102877A (en) 1989-04-28 1992-04-07 Fujisawa Pharmaceutical Co., Ltd. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds
JPH03120280A (ja) * 1989-10-03 1991-05-22 Shionogi & Co Ltd ハロメチルカルバペネム化合物の製法
JPH04234886A (ja) * 1990-03-08 1992-08-24 Fujisawa Pharmaceut Co Ltd 1−アザビシクロ[3.2.0]ヘプト−2−エン−2−カルボン酸化合物
US5011832A (en) 1990-06-26 1991-04-30 Merck & Co., Inc. 2-biphenyl-carbapenem antibacterial agents
WO1992002521A1 (en) 1990-07-27 1992-02-20 Fujisawa Pharmaceutical Co., Ltd. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds
US5034384A (en) 1990-08-01 1991-07-23 Merck & Co., Inc. 2-(9-fluorenonyl)-carbapenem antibacterial agents
JPH04164091A (ja) 1990-10-29 1992-06-09 Shionogi & Co Ltd ハロメチルカルバペネム化合物の製法
US5539102A (en) 1992-02-21 1996-07-23 Shionogi Seiyaku Kabushiki Kaisha Production method for sulfamide
DE4234078A1 (de) 1992-10-09 1994-04-14 Bayer Ag Chinoloncarbonsäuren
US5756725A (en) 1996-04-24 1998-05-26 Merck & Co., Inc. Carbapenem antibacterial compounds, compositions containing such compounds and methods of treatment
US6255300B1 (en) 1997-09-09 2001-07-03 Merck & Co., Inc. Carbapenem antibacterial compounds, compositions containing such compounds and methods of treatment
US6140318A (en) 1997-10-23 2000-10-31 Merck & Co., Inc. Carbapenem antibacterial compounds, compositions containing such compounds and methods of treatment
US6395894B2 (en) 1998-04-16 2002-05-28 Philip J. Pye Process for the synthesis of carbapenem intermidiates, and compounds produced
US6310055B2 (en) 1998-06-02 2001-10-30 Merck & Co., Inc. Halophenoxy substituted carbapenem antibacterial compounds
JP2000136133A (ja) 1998-08-25 2000-05-16 Banyu Pharmaceut Co Ltd メタロ―β―ラクタマ―ゼ阻害剤
EP1505080A1 (en) * 2003-07-28 2005-02-09 KRATON Polymers Research B.V. Method for partially and selectively hydrogenating polymers made of conjugated dienes
WO2005123066A1 (en) * 2004-06-10 2005-12-29 Fob Synthesis, Inc. Carbapenem antibacterials with gram-negative activity and processes for their preparation

Also Published As

Publication number Publication date
CA2802529A1 (en) 2011-12-22
EP2590978B1 (en) 2017-09-20
US20150306071A1 (en) 2015-10-29
JP5922110B2 (ja) 2016-05-24
KR20140018831A (ko) 2014-02-13
US9149461B2 (en) 2015-10-06
ES2653837T3 (es) 2018-02-09
US9937151B2 (en) 2018-04-10
US20130172313A1 (en) 2013-07-04
KR101862041B1 (ko) 2018-05-29
JP2013528659A (ja) 2013-07-11
EP2590978A4 (en) 2013-12-25
EP2590978A2 (en) 2013-05-15
DK2590978T3 (en) 2018-01-02
WO2011160020A3 (en) 2012-04-12
WO2011160020A2 (en) 2011-12-22

Similar Documents

Publication Publication Date Title
US9149461B2 (en) Carbapenem antibacterials with gram-negative activity
US8232268B2 (en) Carbapenem antibacterials with gram-negative activity and processes for their preparation
AU2016239209A1 (en) Novel heterocyclic compounds and their use in preventing or treating bacterial infections
JP7326164B2 (ja) 細菌感染治療のためのカルバペネム化合物及び組成物
JP7589139B2 (ja) 複素環式化合物及び細菌感染の予防又は治療へのそれらの使用
KR20070030856A (ko) 그램-양성 카바페넴 항균제 및 그의 제조방법

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20160614

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20251021

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20260202

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260203

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260804