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SI9600371B - Etilidenski derivati tricikličnih karbapenemov - Google Patents

Etilidenski derivati tricikličnih karbapenemov Download PDF

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Publication number
SI9600371B
SI9600371B SI9600371A SI9600371A SI9600371B SI 9600371 B SI9600371 B SI 9600371B SI 9600371 A SI9600371 A SI 9600371A SI 9600371 A SI9600371 A SI 9600371A SI 9600371 B SI9600371 B SI 9600371B
Authority
SI
Slovenia
Prior art keywords
ethylidene
acid
formula
pharmaceutically acceptable
ester
Prior art date
Application number
SI9600371A
Other languages
English (en)
Other versions
SI9600371A (sl
Inventor
Anton Opar
Toma� �olmajer
Borut An�i�
Tadeja Kuzman
Toma� Mesar
Darko Kocjan
Original Assignee
LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d.
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 LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. filed Critical LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d.
Priority to SI9600371A priority Critical patent/SI9600371B/sl
Priority to AT97947251T priority patent/ATE246192T1/de
Priority to DE69723864T priority patent/DE69723864T2/de
Priority to JP52763998A priority patent/JP4252628B2/ja
Priority to PCT/SI1997/000035 priority patent/WO1998027094A1/en
Priority to EP97947251A priority patent/EP0946558B1/en
Priority to US09/319,660 priority patent/US6489318B1/en
Priority to AU52375/98A priority patent/AU5237598A/en
Publication of SI9600371A publication Critical patent/SI9600371A/sl
Publication of SI9600371B publication Critical patent/SI9600371B/sl

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Classifications

    • 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
    • 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
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medical Preparation Storing Or Oral Administration Devices (AREA)

Description

* V tem dokumentu so objavljeni spremenjeni zahtevki patenta 9600371 A. Zahtevki so bili spremenjeni na podlagi ugotovitvene odločbe, izdane po členu 93(l)(b) Zakona o industrijski lastnini (Uradni list RS, št. 102/04)

Claims (12)

1. Etilidenski derivati tricikličnih karbapenemov s formulo I coox
R v kateri je Y S in je R vodik ali je Y CH2 in je lahko R vodik, (C-i-C4)-alkoksi ali (CiC4)-alkiloksimetil in kjer lahko X pomeni
i. vodikov atom, ii. alkalijsko kovino, iii. zemljoalkalijsko kovino, iv. amonijev ion ali protonirano obliko mono, di ali trisubstituiranega necikličnega ali cikličnega alifatskega amina ali protonirano obliko druge dušikove baze,
v. kvaterniziran amonijev ion, vi. radikal R4, kije lahko:
a) izbran iz skupine, ki obsega (C-i-C2o)-alkil, (CrC2o)-alkenil, substituiran alkil, substituiran silil, ftalidil,
b) ostanek, ki se lahko zapiše v naslednji obliki
2. Etilidenski derivati po zahtevku 1 v obliki čistih diastereoizomerov.
v kateri R5 predstavlja vodik, nižji alkil z 1 do 4 ogljikovimi atomi,
R6 predstavlja vodik, alkil, cikloalkil, alkoksi, cikloalkoksi, cikloalkilalkil, alkeniloksi, fenil.
3. Etilidenski derivati po zahtevku 1 v obliki čistih geometrijskih izomerov.
4. (8S,9R)-10-((E)-etil id en)-11 -okso-1 -azatriciklo[7.2.0.03,8]undec-2-en-2karboksilna kislina, njena farmacevtsko sprejemljiva sol ali ester.
5. (8R,9R)-10-(( E)-etiliden)-11 -okso-1 -azatriciklo[7.2.0.03,8]undec-2-en-2karboksilna kislina, njena farmacevtsko sprejemljiva sol ali ester.
6. (8S,9R)-10-((E)-etiliden)-11-okso-1-aza-6-tiatriciklo[7.2.0.03,8]undec-2-en-2karboksilna kislina, njena farmacevtsko sprejemljiva sol ali ester.
7. (8R,9R)-10-((E)-etiiiden)-11 -okso-1 -aza-6-tiatriciklo[7.2.0.03,8]undec-2-en-2karboksilna kislina, njena farmacevtsko sprejemljiva sol ali ester.
8. Postopek priprave etilidenskih derivatov tricikličnih karbapenemov po zahtevku 1 s formulo I
I v kateri imajo Y, R in X v zahtevku 1 navedene pomene, označen s tem, da
i. spojino s formulo II v kateri R7 pomeni estrsko lahko odstranljivo zaščitno skupino ter imata Y in R v zahtevku 1 navedeni pomen, presnovimo pri temperaturi od -78°C do temperature refluksa z reaktivnim kislinskim derivatom v prisotnosti baze v inertnem organskem topilu ali s kislino R8OH, kjer ima R8 spodaj navedeni pomen, v spojino s formulo III
OR8 kjer imajo R7, Y in R zgoraj navedene pomene in je lahko R8 derivat alifatske kisline, derivat alkansulfonske kisline, derivat arensulfonske kisline, derivat heteroarensulfonske kisline;
ii. spojino s formulo III
O
COOR7 v kateri imajo R7, R8, Y in R zgoraj navedene pomene, pretvorimo z bazno katalizirano eliminacijo pri temperaturi od -78°C do temperature refluksa topila v inertnem organskem topilu v spojino s formulo IV v kateri imajo R7, Y in R zgoraj navedene pomene;
iii. spojino s formulo IV v kateri imajo R7, Y in R zgoraj navedene pomene, po običajnih metodah za odstranitev zaščitne skupine pretvorimo v spojino s formulo I v kateri imajo Y, R in X v zahtevku 1 navedene pomene.
9. Farmacevtski pripravek, ki obsega terapevtsko učinkovito množino etiilidenskega derivata po kateremkoli od zahtevkov 1 do 7 v obliki kisline, farmacevtsko sprejemljive soli ali estra kot učinkovino ter običajne farmacevtsko sprejemljive nosilce in pomožne snovi.
10. Farmacevtski pripravek po zahtevku 9, ki nadalje obsega terapevtsko učinkovito množino β-laktamskega antibiotika kot učinkovino.
11. Uporaba etilidenskega derivata po kateremkoli od zahtevkov 1 do 7 v obliki kisline, farmacevtsko sprejemljive soli ali estra za pripravo farmacevtskega pripravka za zdravljenje bakterijskih infekcij pri ljudeh in živalih.
12. Uporaba etilidenskega derivata po kateremkoli od zahtevkov 1 do 7 v obliki kisline, farmacevtsko sprejemljive soli ali estra za pripravo farmacevtskega pripravka za inhibicijo encima β-laktamaze v medicini in veterini.
SI9600371A 1996-12-18 1996-12-18 Etilidenski derivati tricikličnih karbapenemov SI9600371B (sl)

Priority Applications (8)

Application Number Priority Date Filing Date Title
SI9600371A SI9600371B (sl) 1996-12-18 1996-12-18 Etilidenski derivati tricikličnih karbapenemov
AT97947251T ATE246192T1 (de) 1996-12-18 1997-12-18 Ethyliden-derivate tricyclyscher carbapenems
DE69723864T DE69723864T2 (de) 1996-12-18 1997-12-18 Ethyliden-derivate tricyclyscher carbapenems
JP52763998A JP4252628B2 (ja) 1996-12-18 1997-12-18 三環型カルバペネムのエチリデン誘導体
PCT/SI1997/000035 WO1998027094A1 (en) 1996-12-18 1997-12-18 Ethylidene derivatives of tricyclic carbapenems
EP97947251A EP0946558B1 (en) 1996-12-18 1997-12-18 Ethylidene derivatives of tricyclic carbapenems
US09/319,660 US6489318B1 (en) 1996-12-18 1997-12-18 Ethylidene derivatives of tricyclic carbapenems
AU52375/98A AU5237598A (en) 1996-12-18 1997-12-18 Ethylidene derivatives of tricyclic carbapenems

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SI9600371A SI9600371B (sl) 1996-12-18 1996-12-18 Etilidenski derivati tricikličnih karbapenemov

Publications (2)

Publication Number Publication Date
SI9600371A SI9600371A (sl) 1998-06-30
SI9600371B true SI9600371B (sl) 2005-04-30

Family

ID=20431974

Family Applications (1)

Application Number Title Priority Date Filing Date
SI9600371A SI9600371B (sl) 1996-12-18 1996-12-18 Etilidenski derivati tricikličnih karbapenemov

Country Status (8)

Country Link
US (1) US6489318B1 (sl)
EP (1) EP0946558B1 (sl)
JP (1) JP4252628B2 (sl)
AT (1) ATE246192T1 (sl)
AU (1) AU5237598A (sl)
DE (1) DE69723864T2 (sl)
SI (1) SI9600371B (sl)
WO (1) WO1998027094A1 (sl)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2350907B (en) * 1999-06-09 2002-02-13 Keith Andrew Burton Computer system
UY26380A1 (es) 1999-10-08 2001-04-30 Smithkline Beecham Corp Inhibidores de fab i
EP1560584B1 (en) 2001-04-06 2009-01-14 Affinium Pharmaceuticals, Inc. Fab i inhibitors
US7790709B2 (en) 2002-12-06 2010-09-07 Affinium Pharmaceuticals, Inc. Heterocyclic compounds, methods of making them and their use in therapy
DE602004016831D1 (de) * 2003-03-17 2008-11-13 Affinium Pharm Inc Pharmazeutische zusammensetzungen inhibitoren von fab i und weitere antibiotika enthaltend
KR101299399B1 (ko) 2004-06-04 2013-08-22 아피늄 파마슈티컬스, 인크. 치료제, 및 그의 제조 및 사용 방법
US20090155316A1 (en) * 2004-12-13 2009-06-18 Apt Co., Ltd. Oral Wash
US8318720B2 (en) 2006-07-20 2012-11-27 Affinium Pharmaceuticals, Inc. Acrylamide derivatives as Fab I inhibitors
EP1958630A1 (en) * 2007-02-13 2008-08-20 LEK Pharmaceuticals d.d. Antibacterial combination of a tricyclic carbapenem and an antibiotic
US8263613B2 (en) 2007-02-16 2012-09-11 Affinium Pharmaceuticals, Inc. Salts, prodrugs and polymorphs of fab I inhibitors
EP2085084A1 (en) 2008-01-29 2009-08-05 LEK Pharmaceuticals D.D. Use of inhibitor of beta-lactamases and its combination with beta-lactam antibiotics
EP2135871A1 (en) * 2008-06-18 2009-12-23 LEK Pharmaceuticals D.D. New trinem antibiotics and inhibitors of beta-lactamases
BR122021020778B1 (pt) 2012-06-19 2022-07-12 Debiopharm International Sa Derivados de pró-fármaco de (e)-n-metil-n-((3-metilbenzofuran-2-il) metil)-3-(7-oxo-5,6,7,8-tetraidro- 1, 8- naftirindin-3-il) acrilamida
US10751351B2 (en) 2016-02-26 2020-08-25 Debiopharm International S.A. Medicament for treatment of diabetic foot infections
RS63143B1 (sr) 2016-06-01 2022-05-31 Athira Pharma Inc Jedinjenja
IL298760A (en) 2020-06-05 2023-02-01 Kinnate Biopharma Inc Fibroblast growth factor receptor kinase inhibitors

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005349A1 (en) * 1978-05-06 1979-11-14 Beecham Group Plc Alkylcarbapenems, their preparation, use in pharmaceutical compositions and intermediates
US4235922A (en) 1979-06-15 1980-11-25 Merck & Co., Inc. 3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acid
AU636913B2 (en) * 1989-10-11 1993-05-13 Takeda Chemical Industries Ltd. Tricyclic carbapenem compounds
GB9104769D0 (en) * 1991-03-07 1991-04-17 Glaxo Spa Heterocyclic compounds
GB9104832D0 (en) * 1991-03-07 1991-04-17 Glaxo Spa Heterocyclic compounds
EP0507313A1 (en) * 1991-04-05 1992-10-07 Takeda Chemical Industries, Ltd. Polycyclic carbapenem compounds, their production and use
JPH06166688A (ja) * 1992-10-02 1994-06-14 Takeda Chem Ind Ltd カルバペネム化合物、その製造法および抗菌組成物
GB9323137D0 (en) * 1993-11-10 1994-01-05 Glaxo Spa Chemical compounds
GB9403729D0 (en) * 1994-02-26 1994-04-13 Glaxo Spa Amine derivatives

Also Published As

Publication number Publication date
DE69723864D1 (en) 2003-09-04
WO1998027094A1 (en) 1998-06-25
US6489318B1 (en) 2002-12-03
EP0946558A1 (en) 1999-10-06
AU5237598A (en) 1998-07-15
DE69723864T2 (de) 2004-04-22
ATE246192T1 (de) 2003-08-15
JP2001506258A (ja) 2001-05-15
EP0946558B1 (en) 2003-07-30
JP4252628B2 (ja) 2009-04-08
SI9600371A (sl) 1998-06-30

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Legal Events

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IF Valid on the event date
OU02 Decision according to article 73(2) ipa 1992, publication of decision on partial fulfilment of the invention and change of patent claims

Effective date: 20050210

KO00 Lapse of patent

Effective date: 20130719