ZA200302804B - Pharmaceutical compositions containing oxapenem-3-carboxylic acids. - Google Patents
Pharmaceutical compositions containing oxapenem-3-carboxylic acids. Download PDFInfo
- Publication number
- ZA200302804B ZA200302804B ZA200302804A ZA200302804A ZA200302804B ZA 200302804 B ZA200302804 B ZA 200302804B ZA 200302804 A ZA200302804 A ZA 200302804A ZA 200302804 A ZA200302804 A ZA 200302804A ZA 200302804 B ZA200302804 B ZA 200302804B
- Authority
- ZA
- South Africa
- Prior art keywords
- oxapenem
- protonated
- formula
- compound according
- solution
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- NTSDTZZTKYEUBA-YFKPBYRVSA-N (5S)-7-oxo-6-oxa-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CS[C@@H]2OC(=O)N12 NTSDTZZTKYEUBA-YFKPBYRVSA-N 0.000 title description 3
- -1 oxapenem compound Chemical class 0.000 claims description 20
- 230000003115 biocidal effect Effects 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229940123930 Lactamase inhibitor Drugs 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 101710150104 Sensory rhodopsin-1 Proteins 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
- 239000000243 solution Substances 0.000 description 47
- 150000001875 compounds Chemical class 0.000 description 44
- NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 32
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- JTCJHLLFFDVSII-BYPYZUCNSA-N (5S)-6-oxa-4-thia-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class O=C1O[C@H]2SC=CN12 JTCJHLLFFDVSII-BYPYZUCNSA-N 0.000 description 19
- 230000000694 effects Effects 0.000 description 18
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- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 4
- 101000740462 Escherichia coli Beta-lactamase TEM Proteins 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 3
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- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
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- 229940090805 clavulanate Drugs 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- DKJUQGIRQHSEEB-VAQYAFAPSA-N diazonio-[4-methyl-4-[(5r,6r)-2-[(4-nitrophenyl)methoxycarbonyl]-6-[(1s)-1-[(4-nitrophenyl)methoxycarbonyloxy]ethyl]-7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-en-3-yl]pentyl]azanide Chemical compound O([C@@H](C)[C@H]1C(N2C(=C(O[C@@H]21)C(C)(C)CCCN=[N+]=[N-])C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)=O)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 DKJUQGIRQHSEEB-VAQYAFAPSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- LJKNRSBEKUSSIE-UHFFFAOYSA-N hept-2-ene Chemical compound [CH2]CCCC=CC LJKNRSBEKUSSIE-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229960002182 imipenem Drugs 0.000 description 1
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 description 1
- DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 108040006686 pyruvate synthase activity proteins Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0046—Ear
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Otolaryngology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00309207A EP1199077A1 (de) | 2000-10-19 | 2000-10-19 | Stabilisierte Oxapenem-3-carbonsäure enthaltende Arzneimittel durch Gefriergetrocknen mit pharmazeutischen Trägern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302804B true ZA200302804B (en) | 2005-02-23 |
Family
ID=8173326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302804A ZA200302804B (en) | 2000-10-19 | 2003-04-10 | Pharmaceutical compositions containing oxapenem-3-carboxylic acids. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20040043980A1 (de) |
| EP (2) | EP1199077A1 (de) |
| JP (1) | JP2004511520A (de) |
| AT (1) | ATE311881T1 (de) |
| AU (1) | AU2001294007A1 (de) |
| CY (1) | CY1106058T1 (de) |
| DE (1) | DE60115687T2 (de) |
| DK (1) | DK1326608T3 (de) |
| ES (1) | ES2250483T3 (de) |
| HK (1) | HK1053612A1 (de) |
| WO (1) | WO2002032424A1 (de) |
| ZA (1) | ZA200302804B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1219512C (zh) * | 2000-10-19 | 2005-09-21 | 阿姆拉有限公司 | 含奥沙培南－3－羧酸的药物组合物 |
| GB0106428D0 (en) * | 2001-03-15 | 2001-05-02 | Amura Ltd | Antibacterial composition |
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US43980A (en) * | 1864-08-30 | Improvement in horse-rakes | ||
| US176349A (en) * | 1876-04-18 | Improvement in carbureters | ||
| GB2045236A (en) * | 1979-03-26 | 1980-10-29 | Hoechst Uk Ltd | Oxapenem derivatives |
| US4293555A (en) * | 1979-04-17 | 1981-10-06 | Merck & Co., Inc. | 6- and 6,6-Disubstituted-2-substituted-oxapen-2-em-3-carboxylic acids |
| DE2925009A1 (de) * | 1979-06-21 | 1981-01-08 | Basf Ag | Zubereitung fuer substanzen, verfahren zu deren herstellung und deren verwendung |
| DE3725375A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | Stabile oxapenem-3-carbonsaeuren |
| DE3833693A1 (de) * | 1988-10-04 | 1990-04-05 | Bayer Ag | Stabile oxapenem-3-carbonsaeuren und ihre verwendung als ss-lactamasehemmer |
| DE4027928A1 (de) * | 1990-09-04 | 1992-03-05 | Bayer Ag | Neue 2-tert.substituierte methyl-oxapenem-3-carbonsaeuren und -ester, verfahren zu ihrer herstellung und ihre verwendung |
| DE4142423A1 (de) * | 1991-12-20 | 1993-06-24 | Pfaendler Hans Rudolf | ((ls)-hydroxyalkyl)oxapenem-3-carbonsaeuren und ihre verwendung als betalactamasehemmer |
| DE69532032T2 (de) * | 1994-04-25 | 2004-07-22 | Smithkline Beecham P.L.C., Brentford | Pharmazeutische formulierung, die ein beta-lactamase hemmendes penem in kombination mit einem beta-laktam-antibiotikum enthalten und ihre verwendung zur behandlung von bakteriellen infektionen |
| AU5985596A (en) * | 1995-05-31 | 1996-12-18 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
-
2000
- 2000-10-19 EP EP00309207A patent/EP1199077A1/de not_active Withdrawn
-
2001
- 2001-10-11 EP EP01974492A patent/EP1326608B1/de not_active Expired - Lifetime
- 2001-10-11 JP JP2002535662A patent/JP2004511520A/ja active Pending
- 2001-10-11 AT AT01974492T patent/ATE311881T1/de not_active IP Right Cessation
- 2001-10-11 DK DK01974492T patent/DK1326608T3/da active
- 2001-10-11 ES ES01974492T patent/ES2250483T3/es not_active Expired - Lifetime
- 2001-10-11 US US10/399,703 patent/US20040043980A1/en not_active Abandoned
- 2001-10-11 WO PCT/GB2001/004530 patent/WO2002032424A1/en active IP Right Grant
- 2001-10-11 AU AU2001294007A patent/AU2001294007A1/en not_active Abandoned
- 2001-10-11 DE DE60115687T patent/DE60115687T2/de not_active Expired - Fee Related
-
2003
- 2003-04-10 ZA ZA200302804A patent/ZA200302804B/en unknown
- 2003-08-21 HK HK03105980A patent/HK1053612A1/xx not_active IP Right Cessation
-
2005
- 2005-12-14 CY CY20051101547T patent/CY1106058T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1326608A1 (de) | 2003-07-16 |
| EP1326608B1 (de) | 2005-12-07 |
| DK1326608T3 (da) | 2006-02-06 |
| DE60115687T2 (de) | 2006-06-29 |
| AU2001294007A1 (en) | 2002-04-29 |
| ATE311881T1 (de) | 2005-12-15 |
| US20040043980A1 (en) | 2004-03-04 |
| EP1199077A1 (de) | 2002-04-24 |
| ES2250483T3 (es) | 2006-04-16 |
| WO2002032424A1 (en) | 2002-04-25 |
| HK1053612A1 (en) | 2003-10-31 |
| DE60115687D1 (de) | 2006-01-12 |
| CY1106058T1 (el) | 2011-04-06 |
| JP2004511520A (ja) | 2004-04-15 |
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