NO781372L - Fremgangsmaate for fremstilling av antibakterielle midler - Google Patents
Fremgangsmaate for fremstilling av antibakterielle midlerInfo
- Publication number
- NO781372L NO781372L NO781372A NO781372A NO781372L NO 781372 L NO781372 L NO 781372L NO 781372 A NO781372 A NO 781372A NO 781372 A NO781372 A NO 781372A NO 781372 L NO781372 L NO 781372L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- group
- carbon atoms
- compound
- stated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 68
- 238000002360 preparation method Methods 0.000 title claims description 58
- 239000003242 anti bacterial agent Substances 0.000 title description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 220
- 150000001875 compounds Chemical class 0.000 claims description 190
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 151
- 239000002253 acid Substances 0.000 claims description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims description 84
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 79
- 150000002148 esters Chemical class 0.000 claims description 73
- -1 benzyl ester Chemical class 0.000 claims description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 239000011737 fluorine Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 32
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 238000005984 hydrogenation reaction Methods 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 229930182555 Penicillin Natural products 0.000 claims description 22
- 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 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 229930186147 Cephalosporin Natural products 0.000 claims description 19
- 229940124587 cephalosporin Drugs 0.000 claims description 19
- 150000001780 cephalosporins Chemical class 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- 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 claims description 18
- 229960003022 amoxicillin Drugs 0.000 claims description 18
- 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 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- 239000000460 chlorine Chemical group 0.000 claims description 15
- 229940049954 penicillin Drugs 0.000 claims description 14
- 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 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 13
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 229960000723 ampicillin Drugs 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims description 6
- 229960004659 ticarcillin Drugs 0.000 claims description 6
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 claims description 5
- 229960003669 carbenicillin Drugs 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 230000002195 synergetic effect Effects 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- 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 claims description 4
- 229960001139 cefazolin Drugs 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 claims description 3
- 229960003866 cefaloridine Drugs 0.000 claims description 3
- 125000006502 nitrobenzyl group Chemical group 0.000 claims description 3
- 125000005633 phthalidyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000012374 esterification agent Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229960004592 isopropanol Drugs 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004971 nitroalkyl group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 109
- 239000003921 oil Substances 0.000 description 59
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000000243 solution Substances 0.000 description 32
- 229910004298 SiO 2 Inorganic materials 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 29
- 239000000706 filtrate Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 229960001841 potassium permanganate Drugs 0.000 description 20
- 239000012286 potassium permanganate Substances 0.000 description 20
- 238000001514 detection method Methods 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 19
- 230000008020 evaporation Effects 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class 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
- 239000001913 cellulose Substances 0.000 description 13
- 229920002678 cellulose Polymers 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 238000001665 trituration Methods 0.000 description 10
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000006286 aqueous extract Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 150000002960 penicillins Chemical class 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 6
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical class OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 5
- 229910052681 coesite Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052906 cristobalite Inorganic materials 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 229910052682 stishovite Inorganic materials 0.000 description 5
- 229910052905 tridymite Inorganic materials 0.000 description 5
- 108090000204 Dipeptidase 1 Proteins 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 102000006635 beta-lactamase Human genes 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940102223 injectable solution Drugs 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 235000011090 malic acid Nutrition 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 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
- 230000036765 blood level Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940090805 clavulanate Drugs 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
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- 208000004396 mastitis Diseases 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000008227 sterile water for injection Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000588915 Klebsiella aerogenes Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229960003311 ampicillin trihydrate Drugs 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
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- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229950004791 pirbenicillin Drugs 0.000 description 1
- 229960004632 pivampicillin hydrochloride Drugs 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- HOCWPKXKMNXINF-XQERAMJGSA-N propicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(CC)OC1=CC=CC=C1 HOCWPKXKMNXINF-XQERAMJGSA-N 0.000 description 1
- 229960003672 propicillin Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000020029 respiratory tract infectious disease Diseases 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960002780 talampicillin Drugs 0.000 description 1
- SOROUYSPFADXSN-SUWVAFIASA-N talampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OC2C3=CC=CC=C3C(=O)O2)(C)C)=CC=CC=C1 SOROUYSPFADXSN-SUWVAFIASA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ZBBCUBMBMZNEME-QBGWIPKPSA-L ticarcillin disodium Chemical compound [Na+].[Na+].C=1([C@@H](C([O-])=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)C=CSC=1 ZBBCUBMBMZNEME-QBGWIPKPSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 150000004684 trihydrates Chemical class 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 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 (4)
| 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 |
| GB3707277 | 1977-09-06 | ||
| GB5022977 | 1977-12-02 | ||
| GB5386677 | 1977-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781372L true NO781372L (no) | 1978-10-24 |
Family
ID=27448369
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781372A NO781372L (no) | 1977-04-22 | 1978-04-19 | Fremgangsmaate for fremstilling av antibakterielle midler |
| NO802686A NO802686L (no) | 1977-04-22 | 1980-09-10 | Fremgangsmaate for fremstilling av en ester av et klavulansyreamin |
| NO802682A NO802682L (no) | 1977-04-22 | 1980-09-10 | Fremgangsmaate for fremstilling av et synergistisk farmasoeytisk preparat. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO802686A NO802686L (no) | 1977-04-22 | 1980-09-10 | Fremgangsmaate for fremstilling av en ester av et klavulansyreamin |
| NO802682A NO802682L (no) | 1977-04-22 | 1980-09-10 | Fremgangsmaate for fremstilling av et synergistisk farmasoeytisk preparat. |
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 |
| EP0007717B1 (de) * | 1978-07-29 | 1982-08-11 | Beecham Group Plc | Clavulansäurederivate, ein Verfahren zu ihrer Herstellung, ihre Verwendung und diese enthaltende pharmazeutische Zusammensetzungen |
| EP0008884B1 (de) * | 1978-09-09 | 1983-08-17 | Beecham Group Plc | Clavulansäure-Derivate, ein Verfahren zu ihrer Herstellung und ihre Zusammensetzungen |
| ATE5143T1 (de) * | 1978-09-09 | 1983-11-15 | Beecham Group Plc | Clavulansaeure-derivate und verfahren zu ihrer herstellung. |
| 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 |
| WO2002093996A1 (en) | 2001-05-10 | 2002-11-21 | Parker Hannifin Corporation | Manufacture of electronics enclosure having a metallized shielding layer |
| 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 |
| WO2003030610A1 (en) | 2001-10-02 | 2003-04-10 | 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 IL IL54535A patent/IL54535A0/xx unknown
- 1978-04-18 GR GR56014A patent/GR65296B/el unknown
- 1978-04-19 DE DE19782817085 patent/DE2817085A1/de not_active Withdrawn
- 1978-04-19 FI FI781201A patent/FI65253C/fi not_active IP Right Cessation
- 1978-04-19 DK DK171678A patent/DK171678A/da active IP Right Grant
- 1978-04-19 SE SE7804485A patent/SE7804485L/xx unknown
- 1978-04-19 NO NO781372A patent/NO781372L/no unknown
- 1978-04-19 NZ NZ187018A patent/NZ187018A/en unknown
- 1978-04-20 PT PT67924A patent/PT67924B/pt unknown
- 1978-04-21 NL NL7804273A patent/NL7804273A/xx not_active Application Discontinuation
- 1978-04-21 BE BE187034A patent/BE866276A/xx not_active IP Right Cessation
- 1978-04-21 CA CA301,662A patent/CA1102810A/en not_active Expired
- 1978-04-21 IE IE792/78A patent/IE46623B1/en unknown
- 1978-04-21 FR FR7811851A patent/FR2387986A1/fr active Granted
- 1978-04-21 LU LU79494A patent/LU79494A1/xx unknown
- 1978-04-21 ES ES469051A patent/ES469051A1/es not_active Expired
- 1978-04-22 JP JP4829278A patent/JPS53132593A/ja active Pending
- 1978-04-24 IT IT49037/78A patent/IT1105353B/it active
- 1978-04-24 AR AR271869A patent/AR221051A1/es active
- 1978-04-24 AT AT292078A patent/AT357673B/de not_active IP Right Cessation
-
1980
- 1980-09-10 NO NO802686A patent/NO802686L/no unknown
- 1980-09-10 NO NO802682A patent/NO802682L/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 SE8305160A patent/SE8305160L/sv not_active Application Discontinuation
- 1983-09-23 SE SE8305161A patent/SE8305161D0/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI65253C (fi) | 1984-04-10 |
| AR221051A1 (es) | 1980-12-30 |
| FR2387986B1 (de) | 1980-10-31 |
| FI65253B (fi) | 1983-12-30 |
| SE7804485L (sv) | 1978-10-23 |
| IL63083A0 (en) | 1981-09-13 |
| BE866276A (fr) | 1978-10-23 |
| FI781201A (fi) | 1978-10-23 |
| ES469051A1 (es) | 1980-01-16 |
| IE46623B1 (en) | 1983-08-10 |
| IT1105353B (it) | 1985-10-28 |
| NO802686L (no) | 1978-10-24 |
| DK171678A (da) | 1978-10-23 |
| ATA292078A (de) | 1979-12-15 |
| SE8305160D0 (sv) | 1983-09-23 |
| LU79494A1 (fr) | 1978-09-29 |
| GB1604822A (en) | 1981-12-16 |
| AT357673B (de) | 1980-07-25 |
| JPS53132593A (en) | 1978-11-18 |
| CA1102810A (en) | 1981-06-09 |
| SE8305160L (sv) | 1983-09-23 |
| US4435565A (en) | 1984-03-06 |
| SE8305161L (sv) | 1983-09-23 |
| SE8305161D0 (sv) | 1983-09-23 |
| PT67924A (en) | 1978-05-01 |
| NL7804273A (nl) | 1978-10-24 |
| GR65296B (en) | 1980-08-01 |
| NZ187018A (en) | 1985-04-30 |
| PT67924B (en) | 1979-11-14 |
| IT7849037A0 (it) | 1978-04-24 |
| NO802682L (no) | 1978-10-24 |
| IE780792L (en) | 1978-10-22 |
| FR2387986A1 (fr) | 1978-11-17 |
| IL54535A0 (en) | 1978-07-31 |
| DE2817085A1 (de) | 1978-10-26 |
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