LV12538B - Aizvietotu hidroksiacetil-piperazīn-fenil-oksazolidinonu esteri - Google Patents

Aizvietotu hidroksiacetil-piperazīn-fenil-oksazolidinonu esteri Download PDF

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Publication number
LV12538B
LV12538B LVP-00-91A LV000091A LV12538B LV 12538 B LV12538 B LV 12538B LV 000091 A LV000091 A LV 000091A LV 12538 B LV12538 B LV 12538B
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oxo
piperazinyl
methyl
oxazolidinyl
acetylamino
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LVP-00-91A
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English (en)
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LV12538A (en
Inventor
Steven J. Brickner
Michael R. Barbachyn
Douglas K. Hutchinson
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Pharmacia & Upjohn Company
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Publication of LV12538A publication Critical patent/LV12538A/xx
Publication of LV12538B publication Critical patent/LV12538B/lv

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    • 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
    • C07D413/10—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 carbon chain containing aromatic rings
    • 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
    • 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
    • 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
    • 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 Table
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (6)

  1. LV 12538 IZGUDROJUMA FORMULA 1. Savienojums ar struktūrformulu I
    vai tā farmaceitiski pieņemami sāļi, kurā R ir -C(0)-R\ -P03= vai -P(0)(0H)2; R1 ir C^alkilgrupa, -N(R1 2 3)2, C^alkil-NKR1),,, -fenil-N(R1)2, -fenil-NHC(0)CH2NH2, -C2H4-morfolinilgrupa, piridinilgrupa, C^alkil-OH, C^alkil-OCH3> Cļ.ealkil-CiOJC^, -O-C^alkil-OCI-Ļ C0.3alkil-piperazinilgrupa (neobligāti aizvietota ar C^alkilgrupu), imidazolilgrupa, C^alkil-COOH, -C(CH2OH)2CH3; R2 un R4 ir neatkarīgi izvēlēti no ūdeņraža atoma vai F, izņemot to, ka vismaz viens no R2 vai R4 ir F; R1 ir neatkarīgi izvēlēti no ūdeņraža atoma vai C^alkilgrupas.
  2. 2. Savienojums saskaņā ar 1. punktu, kurā R ir -C(0)-R\ kurā R1 ir C^alkil-grupa, -N(R1)2, C1.6alkil-N(R1)2, -C2H4-morfolinilgrupa, C^alkil-OH, C^galkil-OCH3, OCļ.galkil-OCHg, C0.3alkil-piperazinilgrupa (neobligāti aizvietota ar C^alkilgrupu), imidazolilgrupa, C^alkil-COOH. 1 Savienojums saskaņā ar 1. punktu, kurā R ir -P(0)(0H)2. 2 Savienojums saskaņā ar 1. punktu, kurā R ir -P03=. 3 Savienojums saskaņā ar 2. - 5. punktiem, kas ir optiski tīrs enantiomērs ar 4 Savienojums saskaņā ar 2. punktu, kurā R1 ir -CH3, -CH2N(CH3)2, -CjhVmor-folinilgrupa vai -CH2OH. 2 10 15 20 25 30 S-konfigurāciju oksazolidinona ciklā pie C5. 7. Savienojums saskaņā ar 2. - 6. punktiem, kurā viens no R2 un R3 ir F un otrs ir ūdeņraža atoms. 8. Savienojums saskaņā ar 1. punktu, kurš ir: 1) 3-(4-Morfolinil)propānskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-ok-sazolidinil)-2-fIuorfenil)-1-piperazinil)-2-oksoetilesteris, (S); 2) Nikotīnskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluorfenilj-1 -piperazinil]-2-oksoetilesteris, (S)-; 3) Nikotīnskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2,6-difluorfenil]-1 -piperazinil]-2-oksoetilesteris, (S)-; 4) 1 H-lmidazol-1 -ogļskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksa-zolidinil]-2-fluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-; 5) 1 H-lmidazol-1-ogļskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksa-zoiidinil]-2,6-difluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-; 6) Ogļskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluor-fenil]-1-piperazinil]-2-oksoetilester-2-metoksietilesteris, (S); 7) 4-Dimetilaminobenzoskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-; 8) 4-Dimetilaminobenzoskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2,6-difluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-; 9) Ν,Ν-Dimetilglicīna 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluorfenil]-1 -piperazinil]-2-oksoetilesteris, (S)-; 10) Ν,Ν-Dimetilglicīna 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2,6-difluorfenil]-1 -piperazinil]-2-oksoetilesteris, (S)-; 11) 3-(Dimetilamino)propānskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-; 12) 4(Dimetilamino)butānskābes 2-[4-[4-[5-[(acetilamino)me-til]-2-okso-3-oksazolidinil]-2-fluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-; 13) (4-Metil-1 -piperazinil)etiķskābes 2-[4-[4-[5-[(acetilamino)meti!j-2-okso-3-oksazolidinil]-2-fluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-; 14) Etiķskābes 2-(4-(4-(5~((acetilamino)metil)-2-okso-3-oksazolidinil)-2,6-difluorfenil)-1 -piperazinil)-2-oksoetilesteris, (S); 35 3 LV 12538 15) Sukcinskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-oksazolidinil)-2,6-difluorfenil)-1 -piperazinil)-2-oksoetilmonoesteris, (S); 16) Sukcinskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-oksazolidinil)-2,6-difluorfenil)-1-piperazinil)-2-oksoetilmonoesteris, nātrija sāls, (S); 17) Sukcinskābes 2-(4-(4-(5-((acetiiamino)metil)-2-okso-3-oksazolidinil)-2,6-difluorfenil)-1 -piperazinil)-2-oksoetilmonoesteris, (S); 18) 4-Okso-pentānskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-oksa-zolidinil)-2,6-difluorfenil)-1-piperazinil)-2-oksoetilesteris, (S); 19) 4-Okso-pentānskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-oksa-zolidinil)-2-fluorfenil)-1-piperazinil)-2-oksoetilmonoesteris, (S); 20) Fosforskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-oksazolidinil)-2-fluorfenil)-1 -piperazinil)-2-oksoetilesteris, (S); 21) 4-Aminobenzoskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksa-zolidinii]-2-fluorfenil]-1 -piperazmil]-2-oksoetilesteris, (S)-; 22) 2,2-bis-(Hidroksimetil)propānskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluorfenil]-1-piperazinil]-2-oksoetilesteris, (S)-r 23) Hidroksietiķskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluorfenil]-1-piperazinil]-2-oksoetilesteris, (S); 24) Hidroksietiķskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinilj-2,6-difluorfenil]-1 -piperaziniij-2-oksoetilesteris, (S); 25) Metoksietiķskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-oksazoJidi-nil)-2-fluorfenil)-1-piperazinil)-2-oksoetilesteris, (S); 26) 3-(N-Morfolinil)propānskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3-oksazolidinil)-2,6-difluorfenil)-1-piperazinil)-2-oksoetilesteris, (S); 29) 4-N-(glicinil)aminobenzoskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluorfenii]-1 -piperazinii]-2-oksoetilesteris, (S)-; vai 30) Etiķskābes 2-[4-[4-[5-[(acetilamino)metil]-2-okso-3-oksazolidinil]-2-fluor-fenil]-1 -piperazinil]-2-oksoetilesteris, (S)-. Savienojums saskaņā ar 1. punktu, kurā R ir -CO-fenil-N(R4)2, -CO- piridinilgrupa, -CO-Cļ.ealkil-COCHa, -CO-C(CH2OH)2CH3 vai -CO-fenil-NH- CO-CH2NH2. Savienojums saskaņā ar 9. punktu, kas ir optiski tīrs enantiomērs ar S-konfigurāciju oksazolidinona ciklā pie C5. 4
  3. 11. Savienojums saskaņā ar 9. punktu vai 10. punktu, kurā R2 ir H un R3 ir F.
  4. 12. Savienojums, kurš ir 5 27) (4-Morfolinil)etiķskābes 2-(4-(4-(5-((acetilamino)metil)-2-okso-3- oksazolidinil)-2-fluorfenil)-1 -piperazinil)-2-oksoetilesteris, (S)- vai 28) 4-N-(N,N-dimetilglicinil)aminobenzoskābes 2-[4-[4-[5-[(acetil-amino)metil]-2-okso-3-oksazolidinil]-2-fluorfenil]-1-piperazinil]-2-okso-etilesteris, (S)-. 10
  5. 13. Savienojums saskaņā ar kādu no iepriekšējiem punktiem izmantošanai mikrobu izraisītu infekciju ārstēšanā siltasiņu dzīvniekiem.
  6. 14. Savienojuma saskaņā ar kādu no 1. līdz 12. punktam izmantošana 15 medikamenta ražošanai izmantošanai mikrobu izraisītu infekciju ārstēšanā siltasiņu dzīvniekiem.
LVP-00-91A 1993-11-22 2000-07-14 Aizvietotu hidroksiacetil-piperazīn-fenil-oksazolidinonu esteri LV12538B (lv)

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IL111215A0 (en) 1994-12-29
KR960705818A (ko) 1996-11-08
CO4290433A1 (es) 1996-04-17
PE22896A1 (es) 1996-06-07
DE69419523D1 (en) 1999-08-19
AU8010394A (en) 1995-06-13
EP0730591B1 (en) 1999-07-14
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DE69419523T2 (de) 1999-11-25
CN1046276C (zh) 1999-11-10
CN1135752A (zh) 1996-11-13
JP3698724B2 (ja) 2005-09-21
US5652238A (en) 1997-07-29
ATE182142T1 (de) 1999-07-15
WO1995014684A1 (en) 1995-06-01
EP0730591A1 (en) 1996-09-11
AU698699B2 (en) 1998-11-05
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LV12538A (en) 2000-10-20
DK0730591T3 (da) 2000-01-31
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CA2174107A1 (en) 1995-06-01

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