DK2590978T3 - Carbapenem-antibakterielle midler med gram-negativ aktivitet - Google Patents

Carbapenem-antibakterielle midler med gram-negativ aktivitet Download PDF

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DK2590978T3
DK2590978T3 DK11796509.5T DK11796509T DK2590978T3 DK 2590978 T3 DK2590978 T3 DK 2590978T3 DK 11796509 T DK11796509 T DK 11796509T DK 2590978 T3 DK2590978 T3 DK 2590978T3
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Woo-Baeg Choi
Deog-Il Kim
Ewa Gruszecka-Kowalik
Hyung-Yeul Joo
Shuangpei Liu
Shuli Mao
Yongfeng Li
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Fob Synthesis Inc
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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
    • A61K31/33—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
    • 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
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (24)

1. Forbindelse med formel I:
eller et farmaceutisk acceptabelt salt, eller ester deraf, hvor R1 og R2 er hver uafhængigt valgt fra H eller alkyl; P er H, OH, halogen, eller hydroxyl beskyttet af en hydroxylbeskyttelsesgruppe; hvor hydroxylbeskyttelsesgruppen er triethylsilyl (TES), t-butyldimethylsilyl (TBDMS), o-nitrobenzyloxycarbonyl (ONB), p-nitrobenzyloxycarbonyl (PNB), benzyloxycarbonyl (Cbz), allyloxycarbonyl (Alloc), t-butyloxycarbonyl (Boc) eller 2,2,2-trichlorethyloxycarbonyl (Troc); n er 0, 1 eller 2; X er -(CR2)m- eller -C(=0)-; m er 0, 1 eller 2; Y er CN, SR' eller NRR'; hver R er uafhængigt valgt fra H, alkyl eller haloalkyl; R' er alkyl, NR2; C(=0)R; S02R; SO2NR2; C(=NR)NR2; C(=0)NR2; CR2C(=0)NR2; C(=NR)R; C(=NR)NRS02R; C(=NR)NRC(=0)R; C(=0)CR2NRS02NR2; eller C(=0)CR2NRC(=NR)NR2; og Z er H, alkyl, halo, CN, OR, SR' eller NRR'.
2. Forbindelse med formel II:
eller et farmaceutisk acceptabelt salt, eller ester deraf, hvor R1 og R2 er hver uafhængigt valgt fra H eller alkyl; P er H, OH, halogen, eller hydroxyl beskyttet af en hydroxylbeskyttelsesgruppe; hvor hydroxylbeskyttelsesgruppen er triethylsilyl (TES), t-butyldimethylsilyl (TBDMS), o-nitrobenzyloxycarbonyl (ONB), p-nitrobenzyloxycarbonyl (PNB), benzyloxycarbonyl (Cbz), allyloxycarbonyl (Alloc), t-butyloxycarbonyl (Boc) eller 2,2,2-trichlorethyloxycarbonyl (Troc); X er -(CR2)m- eller -C(=0)-; m er 0, 1 eller 2; Y er CN, OR, SR' eller NRR'; hver R er uafhængigt valgt fra H, alkyl eller haloalkyl; R' er H, alkyl, NR2; C(=0)R; S02R; SO2NR2; C(=NR)NR2; C(=0)NR2; CR2C(=0)NR2; C(=NR)R; C(=NR)NRS02R; C(=NR)NRC(=0)R; C(=0)CR2NRS02NR2; eller C(=0)CR2NRC(=NR)NR2; og Z er H, alkyl, halo, CN, OR, SR' eller NRR'.
3. Forbindelse ifølge krav 1 med formel III:
eller et farmaceutisk acceptabelt salt, eller ester deraf, hvor R1 og R2 er hver uafhængigt valgt fra H eller alkyl; P er H, OH, halogen, eller hydroxyl beskyttet af en hydroxylbeskyttelsesgruppe; hvor hydroxylbeskyttelsesgruppen er triethylsilyl (TES), t-butyldimethylsilyl (TBDMS), o-nitrobenzyloxycarbonyl (ONB), p-nitrobenzyloxycarbonyl (PNB), benzyloxycarbonyl (Cbz), allyloxycarbonyl (Alloc), t-butyloxycarbonyl (Boc) eller 2,2,2-trichlorethyloxycarbonyl (Troc); X er -(CR2)m- eller -C(=0)-; m er 0, 1 eller 2; Y er CN, SR' eller NRR'; hver R er uafhængigt valgt fra H, alkyl eller haloalkyl; R' er alkyl, NR2; C(=0)R; S02R; SO2NR2; C(=NR)NR2; C(=0)NR2; CR2C(=0)NR2; C(=NR)R; C(=NR)NRS02R; C(=NR)NRC(=0)R; C(=0)CR2NRS02NR2; eller C(=0)CR2NRC(=NR)NR2; og Z er H, alkyl, halo, CN, OR, SR' eller NRR'.
4. Forbindelse med formel IV:
eller et farmaceutisk acceptabelt salt, eller ester deraf, hvor R1, R2 og R3 er hver uafhængigt valgt fra H eller alkyl; P er H, OH, halogen, eller hydroxyl beskyttet af en hydroxylbeskyttelsesgruppe; hvor hydroxylbeskyttelsesgruppen er triethylsilyl (TES), t-butyldimethylsilyl (TBDMS), o-nitrobenzyloxycarbonyl (ONB), p-nitrobenzyloxycarbonyl (PNB), benzyloxycarbonyl (Cbz), allyloxycarbonyl (Alloc), t-butyloxycarbonyl (Boc) eller 2,2,2-trichlorethyloxycarbonyl (Troc); n er 0, 1, eller 2 X er -(CR2)m- eller -C(=0)-; m er 0, 1 eller 2; Y er CN, OR, SR' eller NRR'; hver R er uafhængigt valgt fra H, alkyl eller haloalkyl; R' er H, alkyl, NR2; C(=0)R; S02R; SO2NR2; C(=NR)NR2; C(=0)NR2; CR2C(=0)NR2; C(=NR)R; C(=NR)NRS02R; C(=NR)NRC(=0)R; C(=0)CR2NRS02NR2; eller C(=0)CR2NRC(=NR)NR2; og Z er H, alkyl, halo, CN, OR, SR' eller NRR'.
5. Forbindelse ifølge krav 4 med formel V:
eller et farmaceutisk acceptabelt salt, eller ester deraf, hvor R1, R2 og R3 er hver uafhængigt valgt fra H eller alkyl; P er H, OH, halogen, eller hydroxyl beskyttet af en hydroxylbeskyttelsesgruppe; hvor hydroxylbeskyttelsesgruppen er triethylsilyl (TES), t-butyldimethylsilyl (TBDMS), o-nitrobenzyloxycarbonyl (ONB), p-nitrobenzyloxycarbonyl (PNB), benzyloxycarbonyl (Cbz), allyloxycarbonyl (Alloc), t-butyloxycarbonyl (Boc) eller 2,2,2-trichlorethyloxycarbonyl (Troc); X er -(CR2)m- eller -C(=0)-; m er 0, 1 eller 2; Y er CN, OR, SR' eller NRR'; hver R er uafhængigt valgt fra H, alkyl eller haloalkyl; R' er H, alkyl, NR2; C(=0)R; S02R; SO2NR2; C(=NR)NR2; C(=0)NR2; CR2C(=0)NR2; C(=NR)R; C(=NR)NRS02R; C(=NR)NRC(=0)R; C(=0)CR2NRS02NR2; eller C(=0)CR2NRC(=NR)NR2; og Z er H, alkyl, halo, CN, OR, SR' eller NRR'.
6. Forbindelse ifølge krav 1 med formel VI:
eller et farmaceutisk acceptabelt salt, eller ester deraf, hvor R1 og R2 er hver uafhængigt valgt fra H eller alkyl; P er H, OH, halogen, eller hydroxyl beskyttet af en hydroxylbeskyttelsesgruppe; hvor hydroxylbeskyttelsesgruppen er triethylsilyl (TES), t-butyldimethylsilyl (TBDMS), o-nitrobenzyloxycarbonyl (ONB), p-nitrobenzyloxycarbonyl (PNB), benzyloxycarbonyl (Cbz), allyloxycarbonyl (Alloc), t-butyloxycarbonyl (Boc) eller 2,2,2-trichlorethyloxycarbonyl (Troc); X er -(CR2)m- eller -C(=0)-; m er 0, 1 eller 2; Y er CN, SR' eller NRR'; hver R er uafhængigt valgt fra H, alkyl eller haloalkyl; R' er alkyl, NR2; C(=0)R; S02R; SO2NR2; C(=NR)NR2; C(=0)NR2; CR2C( = 0)NR2; C( = NR)R; C(=NR)NRS02R; C( = NR)NRC(=0)R; C(=0)CR2NRS02NR2; eller C(=0)CR2NRC(=NR)NR2; og Z er H, alkyl, halo, CN, OR, SR' eller NRR'.
7. Forbindelse ifølge krav 6, hvor Z-substituenten og X-Y-substituenten er i transkonfiguration i forhold til hinanden.
8. Forbindelse ifølge krav 7, hvor Z er hydroxyl.
9. Forbindelse ifølge krav 8, hvor m er 0, og Y er NRR', hvor R er H og R' er C(=NR)NR2.
10. Forbindelse ifølge krav 1 eller krav 2 valgt fra gruppen bestående af
eller et farmaceutisk acceptabelt salt, eller ester deraf.
11. Forbindelse ifølge krav 1 valgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt, eller ester deraf.
12. Farmaceutisk sammensætning omfattende en forbindelse ifølge et hvilket som helst af kravene 1 til 11 og en farmaceutisk acceptabel bærer eller diluent.
13. Farmaceutisk sammensætning ifølge krav 12, endvidere omfattende mindst et yderligere anti-bakterielt middel.
14. Farmaceutisk sammensætning ifølge krav 13, hvor det yderligere anti-bakterielle middel er en β-lactamase-inhibitor.
15. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 til anvendelse i en fremgangsmåde til behandling afen bakterieinfektion hos en vært.
16. Forbindelse til anvendelse ifølge krav 15, hvor værten er et menneske.
17. Forbindelse til anvendelse ifølge krav 15 eller 16, hvor forbindelsen indgives oralt, parenteralt, intravenøst, intradermalt, subkutant eller topisk.
18. Forbindelse til anvendelse ifølge et hvilket som helst af kravene 15 til 17, hvor bakterieinfektionen skyldes gram-negative bakterier.
19. Forbindelse til anvendelse ifølge et hvilket som helst af kravene 15 til 17, hvor bakterieinfektionen er en bakterieinfektion der er resistent over for et lægemiddel eller flere typer lægemidler.
20. Forbindelse til anvendelse ifølge et hvilket som helst af kravene 15 til 17, hvor forbindelsen indgives i kombination eller skiftevis med et andet anti-bakterielt middel.
21. Forbindelse til anvendelse ifølge krav 20, hvor det andet anti-bakterielle middel er en β-lactamase-inhibitor.
22. Forbindelse ifølge krav 1 hvor forbindelsen er:
eller et farmaceutisk acceptabelt salt, eller ester deraf.
23. Forbindelse ifølge krav 1 hvor forbindelsen er:
eller et farmaceutisk acceptabelt salt, eller ester deraf.
24. Forbindelse til anvendelse ifølge et hvilket som helst af kravene 15 til 17, hvor bakterieinfektionen skyldes Acinetobacter baumannii.
DK11796509.5T 2010-06-18 2011-06-17 Carbapenem-antibakterielle midler med gram-negativ aktivitet DK2590978T3 (da)

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US35639810P 2010-06-18 2010-06-18
PCT/US2011/040883 WO2011160020A2 (en) 2010-06-18 2011-06-17 Carbapenem antibacterials with gram-negative activity

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US (2) US9149461B2 (da)
EP (1) EP2590978B1 (da)
JP (1) JP5922110B2 (da)
KR (1) KR101862041B1 (da)
CA (1) CA2802529C (da)
DK (1) DK2590978T3 (da)
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WO (1) WO2011160020A2 (da)

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KR101798840B1 (ko) 2017-05-17 2017-11-17 주식회사 레고켐 바이오사이언스 신규 오토탁신 저해 화합물 및 이를 함유하는 약제학적 조성물
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JP7458690B2 (ja) * 2018-04-12 2024-04-01 バイエル・アクチエンゲゼルシヤフト 殺有害生物剤としてのｎ－（シクロプロピルメチル）－５－（メチルスルホニル）－ｎ－｛１－［１－（ピリミジン－２－イル）－１ｈ－１，２，４－トリアゾール－５－イル］エチル｝ベンズアミド誘導体及び対応するピリジン－カルボキサミド誘導体
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

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EP2590978A4 (en) 2013-12-25
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US20130172313A1 (en) 2013-07-04
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US9937151B2 (en) 2018-04-10
WO2011160020A3 (en) 2012-04-12
US20150306071A1 (en) 2015-10-29
JP5922110B2 (ja) 2016-05-24
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CA2802529A1 (en) 2011-12-22
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