SI9600371B - Etilidenski derivati tricikličnih karbapenemov - Google Patents
Etilidenski derivati tricikličnih karbapenemov Download PDFInfo
- 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
Links
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 title claims abstract 12
- 239000002253 acid Substances 0.000 claims abstract 10
- 150000002148 esters Chemical class 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 229940041011 carbapenems Drugs 0.000 claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 238000002360 preparation method Methods 0.000 claims abstract 4
- 239000004480 active ingredient Substances 0.000 claims abstract 3
- 239000003814 drug Substances 0.000 claims abstract 3
- 208000035143 Bacterial infection Diseases 0.000 claims abstract 2
- 108090000204 Dipeptidase 1 Proteins 0.000 claims abstract 2
- 241001465754 Metazoa Species 0.000 claims abstract 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract 2
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims abstract 2
- 102000006635 beta-lactamase Human genes 0.000 claims abstract 2
- 239000003937 drug carrier Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 239000002132 β-lactam antibiotic Substances 0.000 claims abstract 2
- 229940124586 β-lactam antibiotics Drugs 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- CJHIIEVRZUZNQE-PCBOLFQESA-N (1S,2R,3E)-3-ethylidene-4-oxo-10-thia-5-azatricyclo[5.4.0.02,5]undec-6-ene-6-carboxylic acid Chemical compound C([C@@H]12)SCCC1=C(C(O)=O)N1[C@H]2\C(=C/C)C1=O CJHIIEVRZUZNQE-PCBOLFQESA-N 0.000 claims 1
- CIJAZLWHLDAZJS-ULYYBGRJSA-N (1e,8ar,8br)-1-ethylidene-2-oxo-5,6,7,8,8a,8b-hexahydroazeto[1,2-b]isoindole-4-carboxylic acid Chemical compound C([C@H]12)CCCC1=C(C(O)=O)N1[C@H]2\C(=C/C)C1=O CIJAZLWHLDAZJS-ULYYBGRJSA-N 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- LDCMOCGAIMMZPI-UHFFFAOYSA-N 2-methylundec-2-enoic acid Chemical compound CCCCCCCCC=C(C)C(O)=O LDCMOCGAIMMZPI-UHFFFAOYSA-N 0.000 claims 1
- CJHIIEVRZUZNQE-OLYQCDQKSA-N C([C@H]12)SCCC1=C(C(O)=O)N1[C@H]2\C(=C/C)C1=O Chemical compound C([C@H]12)SCCC1=C(C(O)=O)N1[C@H]2\C(=C/C)C1=O CJHIIEVRZUZNQE-OLYQCDQKSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000005633 phthalidyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9600371A SI9600371B (sl) | 1996-12-18 | 1996-12-18 | Etilidenski derivati tricikličnih karbapenemov |
| US09/319,660 US6489318B1 (en) | 1996-12-18 | 1997-12-18 | Ethylidene derivatives of tricyclic 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 |
| EP97947251A EP0946558B1 (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 |
| 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 |
| PCT/SI1997/000035 WO1998027094A1 (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 (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2350907B (en) * | 1999-06-09 | 2002-02-13 | Keith Andrew Burton | Computer system |
| PE20010635A1 (es) | 1999-10-08 | 2001-08-15 | Smithkline Beecham Corp | Inhibidores de fab i utiles para el tratamiento de infecciones bacterianas |
| AU2002367773A1 (en) | 2001-04-06 | 2003-11-03 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| SI1575951T1 (sl) | 2002-12-06 | 2014-10-30 | Debiopharm International Sa Forum "Apres-Demain" | Heterociklične spojine, postopki za njihovo izdelavo in njihova uporaba v terapiji |
| ATE409485T1 (de) * | 2003-03-17 | 2008-10-15 | Affinium Pharm Inc | Pharmazeutische zusammensetzungen inhibitoren von fab i und weitere antibiotika enthaltend |
| US8450307B2 (en) | 2004-06-04 | 2013-05-28 | Affinium Pharmaceuticals, Inc. | Therapeutic agents, and methods of making and using the same |
| EP1842524B1 (en) * | 2004-12-13 | 2013-01-23 | APT Co., Ltd. | Cleaning liquid for oral cavity |
| JP5468899B2 (ja) | 2006-07-20 | 2014-04-09 | アフィニウム ファーマシューティカルズ， インク． | Ｆａｂｉインヒビターとしてのアクリルアミド誘導体 |
| EP1958630A1 (en) * | 2007-02-13 | 2008-08-20 | LEK Pharmaceuticals d.d. | Antibacterial combination of a tricyclic carbapenem and an antibiotic |
| EP3255045A1 (en) | 2007-02-16 | 2017-12-13 | Debiopharm International SA | 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 |
| MY170437A (en) | 2012-06-19 | 2019-07-31 | Debiopharm Int Sa | Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
| PL3419628T3 (pl) | 2016-02-26 | 2021-05-31 | Debiopharm International Sa | Lek do leczenia zakażeń stopy cukrzycowej |
| AU2017273857B2 (en) | 2016-06-01 | 2021-08-19 | Athira Pharma, Inc. | Compounds |
| HRP20230437T1 (hr) | 2019-02-14 | 2023-07-07 | Debiopharm International S.A. | Formulacija afabicina, postupak izrade iste |
| CN113939306B (zh) | 2019-06-14 | 2024-07-19 | 德彪药业国际股份公司 | 用于治疗涉及生物膜的细菌感染的药物及其用途 |
| TW202210472A (zh) | 2020-06-05 | 2022-03-16 | 美商奇奈特生物製藥公司 | 纖維母細胞生長因子受體激酶之抑制劑 |
Family Cites Families (9)
| 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 |
| GB9104832D0 (en) * | 1991-03-07 | 1991-04-17 | Glaxo Spa | Heterocyclic compounds |
| GB9104769D0 (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 |
-
1996
- 1996-12-18 SI SI9600371A patent/SI9600371B/sl not_active IP Right Cessation
-
1997
- 1997-12-18 WO PCT/SI1997/000035 patent/WO1998027094A1/en not_active Ceased
- 1997-12-18 DE DE69723864T patent/DE69723864T2/de not_active Expired - Lifetime
- 1997-12-18 AT AT97947251T patent/ATE246192T1/de active
- 1997-12-18 EP EP97947251A patent/EP0946558B1/en not_active Expired - Lifetime
- 1997-12-18 US US09/319,660 patent/US6489318B1/en not_active Expired - Fee Related
- 1997-12-18 AU AU52375/98A patent/AU5237598A/en not_active Abandoned
- 1997-12-18 JP JP52763998A patent/JP4252628B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SI9600371A (sl) | 1998-06-30 |
| ATE246192T1 (de) | 2003-08-15 |
| US6489318B1 (en) | 2002-12-03 |
| EP0946558B1 (en) | 2003-07-30 |
| WO1998027094A1 (en) | 1998-06-25 |
| DE69723864D1 (en) | 2003-09-04 |
| AU5237598A (en) | 1998-07-15 |
| JP4252628B2 (ja) | 2009-04-08 |
| EP0946558A1 (en) | 1999-10-06 |
| DE69723864T2 (de) | 2004-04-22 |
| JP2001506258A (ja) | 2001-05-15 |
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