FI65253C - Foerfarande foer framstaellning av antibakteriellt verksamma 9-aminodeoxi-clavulansyraderivat - Google Patents
Foerfarande foer framstaellning av antibakteriellt verksamma 9-aminodeoxi-clavulansyraderivat Download PDFInfo
- Publication number
- FI65253C FI65253C FI781201A FI781201A FI65253C FI 65253 C FI65253 C FI 65253C FI 781201 A FI781201 A FI 781201A FI 781201 A FI781201 A FI 781201A FI 65253 C FI65253 C FI 65253C
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- Finland
- Prior art keywords
- acid
- benzyl
- formula
- evaporated
- water
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 105
- 150000003839 salts Chemical class 0.000 claims description 44
- 238000002360 preparation method Methods 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 207
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 111
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- -1 hydrochloric Chemical class 0.000 description 67
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 51
- 239000003921 oil Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 239000000203 mixture Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 36
- 239000000047 product Substances 0.000 description 35
- 229910004298 SiO 2 Inorganic materials 0.000 description 33
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 31
- 229940090805 clavulanate Drugs 0.000 description 31
- 229960003022 amoxicillin Drugs 0.000 description 29
- 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 29
- 239000002904 solvent Substances 0.000 description 27
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000012286 potassium permanganate Substances 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 238000001514 detection method Methods 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 229930182555 Penicillin Natural products 0.000 description 15
- 238000005507 spraying Methods 0.000 description 15
- 229930186147 Cephalosporin Natural products 0.000 description 14
- 229940124587 cephalosporin Drugs 0.000 description 14
- 150000001780 cephalosporins Chemical class 0.000 description 14
- 238000005984 hydrogenation reaction Methods 0.000 description 14
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 13
- 239000001913 cellulose Substances 0.000 description 13
- 229920002678 cellulose Polymers 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- 239000006260 foam Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 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 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- 239000012230 colorless oil Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 238000001665 trituration Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 229940049954 penicillin Drugs 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
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- 239000012074 organic phase Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 7
- 241000588724 Escherichia coli Species 0.000 description 7
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- 229910002091 carbon monoxide Inorganic materials 0.000 description 7
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229940016273 amoxicillin 50 mg Drugs 0.000 description 6
- DADQTDAEJJZHDV-UHFFFAOYSA-N butan-1-ol;propan-2-ol;hydrate Chemical compound O.CC(C)O.CCCCO DADQTDAEJJZHDV-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 150000002960 penicillins Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 230000002195 synergetic effect Effects 0.000 description 6
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 5
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 5
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229960001139 cefazolin Drugs 0.000 description 5
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 5
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- 108090000204 Dipeptidase 1 Proteins 0.000 description 4
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 3
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 3
- AZUFHGGGPUUXKI-FLFDDASRSA-N benzyl (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound O=C([C@@H]1N2C(=O)C[C@H]2O\C1=C/CO)OCC1=CC=CC=C1 AZUFHGGGPUUXKI-FLFDDASRSA-N 0.000 description 3
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- 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)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Medical Uses (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16764/77A GB1604822A (en) | 1977-04-22 | 1977-04-22 | N-monosubstituted-9-amino-9-deoxyclavulanic acid derivative |
| GB1676477 | 1977-04-22 | ||
| GB3707277 | 1977-09-06 | ||
| GB3707277 | 1977-09-06 | ||
| GB5022977 | 1977-12-02 | ||
| GB5022977 | 1977-12-02 | ||
| GB5386677 | 1977-12-23 | ||
| GB5386677 | 1977-12-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI781201A7 FI781201A7 (fi) | 1978-10-23 |
| FI65253B FI65253B (fi) | 1983-12-30 |
| FI65253C true FI65253C (fi) | 1984-04-10 |
Family
ID=27448369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI781201A FI65253C (fi) | 1977-04-22 | 1978-04-19 | Foerfarande foer framstaellning av antibakteriellt verksamma 9-aminodeoxi-clavulansyraderivat |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4435565A (de) |
| JP (1) | JPS53132593A (de) |
| AR (1) | AR221051A1 (de) |
| AT (1) | AT357673B (de) |
| BE (1) | BE866276A (de) |
| CA (1) | CA1102810A (de) |
| DE (1) | DE2817085A1 (de) |
| DK (1) | DK171678A (de) |
| ES (1) | ES469051A1 (de) |
| FI (1) | FI65253C (de) |
| FR (1) | FR2387986A1 (de) |
| GB (1) | GB1604822A (de) |
| GR (1) | GR65296B (de) |
| IE (1) | IE46623B1 (de) |
| IL (2) | IL54535A0 (de) |
| IT (1) | IT1105353B (de) |
| LU (1) | LU79494A1 (de) |
| NL (1) | NL7804273A (de) |
| NO (3) | NO781372L (de) |
| NZ (1) | NZ187018A (de) |
| PT (1) | PT67924B (de) |
| SE (3) | SE7804485L (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005014A1 (de) * | 1978-04-22 | 1979-10-31 | Beecham Group Plc | Clavulansäure-Derivate, Herstellung und Zusammensetzungen |
| DE2963534D1 (en) * | 1978-07-29 | 1982-10-07 | Beecham Group Plc | Clavulanic acid derivatives, a process for their preparation, their use, and pharmaceutical compositions containing them |
| EP0076369A1 (de) * | 1978-09-09 | 1983-04-13 | Beecham Group Plc | Beta-Lactam-Derivate |
| EP0008884B1 (de) * | 1978-09-09 | 1983-08-17 | Beecham Group Plc | Clavulansäure-Derivate, ein Verfahren zu ihrer Herstellung und ihre Zusammensetzungen |
| EP0010369B1 (de) * | 1978-10-25 | 1983-07-20 | Beecham Group Plc | Clavulansäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| ZA804670B (en) * | 1979-08-03 | 1981-07-29 | Beecham Group Ltd | Derivatives of clavulanic acid, a process for their preparation and their use |
| EP0062407A1 (de) * | 1981-03-10 | 1982-10-13 | Beecham Group Plc | Beta-Lactame enthaltende therapeutische Verbindungen |
| US5566055A (en) * | 1995-03-03 | 1996-10-15 | Parker-Hannifin Corporation | Shieled enclosure for electronics |
| EP1386527A1 (de) | 2001-05-10 | 2004-02-04 | Parker Hannifin Corporation | Herstellung eines gehäuses für elektronik mit einer metallisierten schutzschicht |
| DE60206489T2 (de) | 2001-05-11 | 2006-07-13 | Parker-Hannifin Corp., Cleveland | Gezahnte Dichtung für EMI-Abschirmungsanwendungen mit niedrigen Verpressungskräften |
| US6809254B2 (en) | 2001-07-20 | 2004-10-26 | Parker-Hannifin Corporation | Electronics enclosure having an interior EMI shielding and cosmetic coating |
| US20030091777A1 (en) * | 2001-08-14 | 2003-05-15 | Peter Jones | Clean release tape for EMI shielding |
| US6784363B2 (en) | 2001-10-02 | 2004-08-31 | Parker-Hannifin Corporation | EMI shielding gasket construction |
| JP6169040B2 (ja) | 2014-05-12 | 2017-07-26 | 東京エレクトロン株式会社 | プラズマ処理装置の上部電極構造、プラズマ処理装置、及びプラズマ処理装置の運用方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU503489B2 (en) * | 1975-10-13 | 1979-09-06 | Beecham Group Limited | Substituted aminodeoxy clavulanic acid |
| GB1585124A (en) * | 1976-06-04 | 1981-02-25 | Glaxo Lab Ltd | Clavulanic acid derivatives |
| NZ187013A (en) | 1977-04-27 | 1985-04-30 | Beecham Group Ltd | 9-amino-9-deoxy-clavulanic acid derivatives and pharmaceutical compositions |
-
1977
- 1977-04-22 GB GB16764/77A patent/GB1604822A/en not_active Expired
-
1978
- 1978-04-18 GR GR56014A patent/GR65296B/el unknown
- 1978-04-18 IL IL54535A patent/IL54535A0/xx unknown
- 1978-04-19 SE SE7804485A patent/SE7804485L/xx unknown
- 1978-04-19 DE DE19782817085 patent/DE2817085A1/de not_active Withdrawn
- 1978-04-19 DK DK171678A patent/DK171678A/da active IP Right Grant
- 1978-04-19 FI FI781201A patent/FI65253C/fi not_active IP Right Cessation
- 1978-04-19 NZ NZ187018A patent/NZ187018A/en unknown
- 1978-04-19 NO NO781372A patent/NO781372L/no unknown
- 1978-04-20 PT PT67924A patent/PT67924B/pt unknown
- 1978-04-21 ES ES469051A patent/ES469051A1/es not_active Expired
- 1978-04-21 BE BE187034A patent/BE866276A/xx not_active IP Right Cessation
- 1978-04-21 IE IE792/78A patent/IE46623B1/en unknown
- 1978-04-21 LU LU79494A patent/LU79494A1/xx unknown
- 1978-04-21 NL NL7804273A patent/NL7804273A/xx not_active Application Discontinuation
- 1978-04-21 CA CA301,662A patent/CA1102810A/en not_active Expired
- 1978-04-21 FR FR7811851A patent/FR2387986A1/fr active Granted
- 1978-04-22 JP JP4829278A patent/JPS53132593A/ja active Pending
- 1978-04-24 AT AT292078A patent/AT357673B/de not_active IP Right Cessation
- 1978-04-24 AR AR271869A patent/AR221051A1/es active
- 1978-04-24 IT IT49037/78A patent/IT1105353B/it active
-
1980
- 1980-09-10 NO NO802682A patent/NO802682L/no unknown
- 1980-09-10 NO NO802686A patent/NO802686L/no unknown
-
1981
- 1981-03-16 US US06/244,098 patent/US4435565A/en not_active Expired - Fee Related
- 1981-06-11 IL IL63083A patent/IL63083A0/xx unknown
-
1983
- 1983-09-23 SE SE8305161A patent/SE8305161L/sv not_active Application Discontinuation
- 1983-09-23 SE SE8305160A patent/SE8305160D0/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7804273A (nl) | 1978-10-24 |
| GB1604822A (en) | 1981-12-16 |
| SE8305160L (sv) | 1983-09-23 |
| IT7849037A0 (it) | 1978-04-24 |
| NO781372L (no) | 1978-10-24 |
| US4435565A (en) | 1984-03-06 |
| NO802682L (no) | 1978-10-24 |
| BE866276A (fr) | 1978-10-23 |
| IL63083A0 (en) | 1981-09-13 |
| NZ187018A (en) | 1985-04-30 |
| IE46623B1 (en) | 1983-08-10 |
| PT67924B (en) | 1979-11-14 |
| CA1102810A (en) | 1981-06-09 |
| FI781201A7 (fi) | 1978-10-23 |
| SE8305160D0 (sv) | 1983-09-23 |
| PT67924A (en) | 1978-05-01 |
| IE780792L (en) | 1978-10-22 |
| AT357673B (de) | 1980-07-25 |
| GR65296B (en) | 1980-08-01 |
| NO802686L (no) | 1978-10-24 |
| IT1105353B (it) | 1985-10-28 |
| FR2387986A1 (fr) | 1978-11-17 |
| JPS53132593A (en) | 1978-11-18 |
| FR2387986B1 (de) | 1980-10-31 |
| ATA292078A (de) | 1979-12-15 |
| ES469051A1 (es) | 1980-01-16 |
| SE8305161D0 (sv) | 1983-09-23 |
| DE2817085A1 (de) | 1978-10-26 |
| IL54535A0 (en) | 1978-07-31 |
| LU79494A1 (fr) | 1978-09-29 |
| SE7804485L (sv) | 1978-10-23 |
| AR221051A1 (es) | 1980-12-30 |
| SE8305161L (sv) | 1983-09-23 |
| FI65253B (fi) | 1983-12-30 |
| DK171678A (da) | 1978-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: BEECHAM GROUP LTD |