FI79112C - 6-aminoalkylpenicillansyra-1,1-dioxider och deras derivat som -laktamas-inhibitorer. - Google Patents
6-aminoalkylpenicillansyra-1,1-dioxider och deras derivat som -laktamas-inhibitorer. Download PDFInfo
- Publication number
- FI79112C FI79112C FI830081A FI830081A FI79112C FI 79112 C FI79112 C FI 79112C FI 830081 A FI830081 A FI 830081A FI 830081 A FI830081 A FI 830081A FI 79112 C FI79112 C FI 79112C
- Authority
- FI
- Finland
- Prior art keywords
- benzyl
- acid
- hydrogen
- title product
- ethyl acetate
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 15
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000003951 lactams Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 66
- -1 pivaloyloxymethyl Chemical group 0.000 claims description 51
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006289 hydroxybenzyl group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
- 239000000047 product Substances 0.000 description 100
- 239000000243 solution Substances 0.000 description 38
- 239000000203 mixture Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 27
- 239000002132 β-lactam antibiotic Substances 0.000 description 26
- 229940124586 β-lactam antibiotics Drugs 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000010410 layer Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229920003045 dextran sodium sulfate Polymers 0.000 description 10
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 229930182555 Penicillin Natural products 0.000 description 9
- 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 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 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 5
- 239000003781 beta lactamase inhibitor Substances 0.000 description 5
- 102000006635 beta-lactamase Human genes 0.000 description 5
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
- 229940049954 penicillin Drugs 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229930186147 Cephalosporin Natural products 0.000 description 4
- 108090000204 Dipeptidase 1 Proteins 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 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 4
- 229960000723 ampicillin Drugs 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 4
- 229940124587 cephalosporin Drugs 0.000 description 4
- 150000001780 cephalosporins Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
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- 239000012452 mother liquor Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 4
- ZMMRLWFGWQVVJD-UHFFFAOYSA-O (n,n-dimethylcarbamimidoyl)-dimethylazanium;azide Chemical compound [N-]=[N+]=[N-].CN(C)C(N)=[N+](C)C ZMMRLWFGWQVVJD-UHFFFAOYSA-O 0.000 description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 3
- WYUIPMUZDFHKMP-UHFFFAOYSA-N 5-chloro-1,3-dihydropyrrolo[3,2-b]pyridin-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=N1 WYUIPMUZDFHKMP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229960003022 amoxicillin Drugs 0.000 description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
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- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
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- 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 3
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- 230000003389 potentiating effect Effects 0.000 description 3
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical group O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 239000005909 Kieselgur Substances 0.000 description 2
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- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GCFBRXLSHGKWDP-XCGNWRKASA-N cefoperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 GCFBRXLSHGKWDP-XCGNWRKASA-N 0.000 description 2
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
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- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
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- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 2
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- 238000010561 standard procedure Methods 0.000 description 2
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- 150000003952 β-lactams Chemical group 0.000 description 2
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- WRFCGBVLTRJBKN-QSNWEANLSA-N (2s,5r,6r)-6-[[(2r)-2-[[2-[[amino(pyridin-4-yl)methylidene]amino]acetyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC=CC=1)C(=O)CN=C(N)C1=CC=NC=C1 WRFCGBVLTRJBKN-QSNWEANLSA-N 0.000 description 1
- SBUCDZYLTRYMFG-PBFPGSCMSA-N (6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](N)C=3C=CC(O)=CC=3)[C@H]2SC1 SBUCDZYLTRYMFG-PBFPGSCMSA-N 0.000 description 1
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- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
- 150000003953 γ-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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- 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
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; 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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33879782A | 1982-01-11 | 1982-01-11 | |
| US33879782 | 1982-01-11 | ||
| US38832482A | 1982-06-14 | 1982-06-14 | |
| US38832482 | 1982-06-14 | ||
| US38832382 | 1982-06-14 | ||
| US06/388,323 US4427678A (en) | 1982-01-11 | 1982-06-14 | 6-Aminomethylpenicillanic acid 1,1-dioxide derivatives as beta-lactamase inhibitors |
| US43437182 | 1982-10-21 | ||
| US06/434,371 US4452796A (en) | 1982-06-14 | 1982-10-21 | 6-Aminoalkylpenicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI830081A0 FI830081A0 (fi) | 1983-01-10 |
| FI830081L FI830081L (fi) | 1983-07-12 |
| FI79112B FI79112B (fi) | 1989-07-31 |
| FI79112C true FI79112C (fi) | 1989-11-10 |
Family
ID=27502592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI830081A FI79112C (fi) | 1982-01-11 | 1983-01-10 | 6-aminoalkylpenicillansyra-1,1-dioxider och deras derivat som -laktamas-inhibitorer. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0084925B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH0689005B2 (cg-RX-API-DMAC7.html) |
| AU (1) | AU538468B2 (cg-RX-API-DMAC7.html) |
| BG (1) | BG42676A3 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1190921A (cg-RX-API-DMAC7.html) |
| DD (2) | DD218365A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3362826D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK166883B1 (cg-RX-API-DMAC7.html) |
| ES (2) | ES8403489A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI79112C (cg-RX-API-DMAC7.html) |
| GR (1) | GR77152B (cg-RX-API-DMAC7.html) |
| HU (1) | HU189211B (cg-RX-API-DMAC7.html) |
| IE (1) | IE54390B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL67647A (cg-RX-API-DMAC7.html) |
| NO (6) | NO830046L (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ202982A (cg-RX-API-DMAC7.html) |
| PL (1) | PL142315B1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT76077B (cg-RX-API-DMAC7.html) |
| RO (2) | RO84910B (cg-RX-API-DMAC7.html) |
| YU (1) | YU43646B (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4499017A (en) * | 1983-06-06 | 1985-02-12 | Pfizer Inc. | Beta-lactamase inhibiting 6-(alkoxyamino-methyl) penicillanic acid 1,1-dioxide and derivatives |
| US4502990A (en) * | 1983-06-06 | 1985-03-05 | Pfizer Inc. | Process for 6-(aminomethyl)penicillanic acid 1,1-dioxide and derivatives thereof |
| JPS60239489A (ja) * | 1984-05-15 | 1985-11-28 | Meiji Seika Kaisha Ltd | ６−エピペニシリンスルホン化合物及びその製造方法 |
| GB2206579B (en) * | 1987-07-10 | 1991-05-29 | Erba Farmitalia | 6a and 6b-(substituted methyl)-penicillanic acid derivatives |
| WO2008141764A1 (en) * | 2007-05-21 | 2008-11-27 | Hans Rudolf Pfaendler | Bactericidal anti-mrsa active pharmaceutical composition containing carbapenems |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4237051A (en) * | 1979-04-19 | 1980-12-02 | Schering Corporation | Stereospecific production of 6- or 7-carbon-substituted-β-lactams |
| DE2927004A1 (de) * | 1979-07-04 | 1981-05-27 | Bayer Ag, 5090 Leverkusen | Penicillansaeure-1,1-dioxide, ihre herstellung und ihre verwendung als arzneimittel als arzneimittel |
| US4287181A (en) * | 1979-10-22 | 1981-09-01 | Pfizer Inc. | Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors |
-
1983
- 1983-01-04 RO RO109609A patent/RO84910B/ro unknown
- 1983-01-04 RO RO83113375A patent/RO87705A/ro unknown
- 1983-01-05 DE DE8383300042T patent/DE3362826D1/de not_active Expired
- 1983-01-05 EP EP83300042A patent/EP0084925B1/en not_active Expired
- 1983-01-07 NO NO830046A patent/NO830046L/no unknown
- 1983-01-07 GR GR70215A patent/GR77152B/el unknown
- 1983-01-10 IE IE42/83A patent/IE54390B1/en not_active IP Right Cessation
- 1983-01-10 FI FI830081A patent/FI79112C/fi not_active IP Right Cessation
- 1983-01-10 AU AU10232/83A patent/AU538468B2/en not_active Ceased
- 1983-01-10 BG BG059284A patent/BG42676A3/xx unknown
- 1983-01-10 YU YU44/83A patent/YU43646B/xx unknown
- 1983-01-10 HU HU8370A patent/HU189211B/hu not_active IP Right Cessation
- 1983-01-10 PT PT76077A patent/PT76077B/pt not_active IP Right Cessation
- 1983-01-10 DK DK007483A patent/DK166883B1/da active
- 1983-01-10 NZ NZ202982A patent/NZ202982A/en unknown
- 1983-01-10 CA CA000419181A patent/CA1190921A/en not_active Expired
- 1983-01-10 IL IL67647A patent/IL67647A/xx not_active IP Right Cessation
- 1983-01-11 DD DD83262053A patent/DD218365A5/de not_active IP Right Cessation
- 1983-01-11 DD DD83247166A patent/DD209462A5/de not_active IP Right Cessation
- 1983-01-11 PL PL1983240108A patent/PL142315B1/pl unknown
- 1983-01-11 JP JP58002768A patent/JPH0689005B2/ja not_active Expired - Lifetime
- 1983-01-11 ES ES518912A patent/ES8403489A1/es not_active Expired
- 1983-08-30 ES ES525238A patent/ES8507147A1/es not_active Expired
- 1983-09-22 NO NO833415A patent/NO833415L/no unknown
- 1983-09-22 NO NO833416A patent/NO833416L/no unknown
-
1984
- 1984-03-20 NO NO841069A patent/NO841069L/no unknown
- 1984-03-20 NO NO841068A patent/NO841068L/no unknown
- 1984-03-20 NO NO841070A patent/NO841070L/no unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: PFIZER INC. |