DE2747350A1 - Clavulansaeureanaloge, deren salze und ester und verfahren zu deren herstellung - Google Patents

Clavulansaeureanaloge, deren salze und ester und verfahren zu deren herstellung

Info

Publication number: DE2747350A1
Authority: DE; Germany
Prior art keywords: group; formula; compound; salt; groups
Prior art date: 1976-10-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE19772747350

Other languages

German (de)

English (en)

Inventor

Peter Clive Cherry

Christopher Earle Newall

Alan Paul Tonge

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Laboratories Ltd

Original Assignee

Glaxo Laboratories Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-10-22

Filing date

1977-10-21

Publication date

1978-04-27

1977-10-21 Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd

1978-04-27 Publication of DE2747350A1 publication Critical patent/DE2747350A1/de

Status Withdrawn legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims description 38
238000000034 method Methods 0.000 title claims description 23
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 title description 6
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 69
-1 pentan-2,4-dion-3-yl group Chemical group 0.000 claims description 63
150000002148 esters Chemical class 0.000 claims description 37
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 16
239000003782 beta lactam antibiotic agent Substances 0.000 claims description 16
239000011734 sodium Substances 0.000 claims description 16
239000002132 β-lactam antibiotic Substances 0.000 claims description 16
229940124586 β-lactam antibiotics Drugs 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
150000003952 β-lactams Chemical class 0.000 claims description 13
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 claims description 12
229910052708 sodium Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000012038 nucleophile Substances 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
239000002585 base Substances 0.000 claims description 6
238000003776 cleavage reaction Methods 0.000 claims description 6
150000003983 crown ethers Chemical class 0.000 claims description 6
230000007017 scission Effects 0.000 claims description 6
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
230000003115 biocidal effect Effects 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
150000007529 inorganic bases Chemical class 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
150000008282 halocarbons Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
238000007257 deesterification reaction Methods 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
125000000962 organic group Chemical group 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
229910052716 thallium Inorganic materials 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229910052749 magnesium Inorganic materials 0.000 claims 1
239000011777 magnesium Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
102000006635 beta-lactamase Human genes 0.000 description 7
150000002084 enol ethers Chemical class 0.000 description 7
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
108020004256 Beta-lactamase Proteins 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
229940088710 antibiotic agent Drugs 0.000 description 5
125000005002 aryl methyl group Chemical group 0.000 description 5
239000003480 eluent Substances 0.000 description 5
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
241000191967 Staphylococcus aureus Species 0.000 description 4
229960000723 ampicillin Drugs 0.000 description 4
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 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000003921 oil Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960003324 clavulanic acid Drugs 0.000 description 3
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical class CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
108090000204 Dipeptidase 1 Proteins 0.000 description 2
241000588722 Escherichia Species 0.000 description 2
241000606768 Haemophilus influenzae Species 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000588915 Klebsiella aerogenes Species 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
241000588770 Proteus mirabilis Species 0.000 description 2
241000588767 Proteus vulgaris Species 0.000 description 2
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
125000005042 acyloxymethyl group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229940024554 amdinocillin Drugs 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
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 2
229960003022 amoxicillin Drugs 0.000 description 2
239000003781 beta lactamase inhibitor Substances 0.000 description 2
229940126813 beta-lactamase inhibitor Drugs 0.000 description 2
238000009835 boiling Methods 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
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 description 2
229960003669 carbenicillin Drugs 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 2
229940106164 cephalexin Drugs 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
BWWVAEOLVKTZFQ-ISVUSNJMSA-N chembl530 Chemical compound N(/[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)=C\N1CCCCCC1 BWWVAEOLVKTZFQ-ISVUSNJMSA-N 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
229940047650 haemophilus influenzae Drugs 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000011630 iodine Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910021645 metal ion Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
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 2
125000005633 phthalidyl group Chemical group 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
229940007042 proteus vulgaris Drugs 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
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 description 2
229960004659 ticarcillin Drugs 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
KQPGVCMZXFBYMM-UHFFFAOYSA-N (4-nitrophenyl)methyl 3-oxobutanoate Chemical class CC(=O)CC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 KQPGVCMZXFBYMM-UHFFFAOYSA-N 0.000 description 1
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
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 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
241000588697 Enterobacter cloacae Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical class CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000588772 Morganella morganii Species 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588777 Providencia rettgeri Species 0.000 description 1
241000607760 Shigella sonnei Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000187433 Streptomyces clavuligerus Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 description 1
229960003972 cefacetrile Drugs 0.000 description 1
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 1
229950004030 cefaloglycin Drugs 0.000 description 1
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 description 1
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
229960001139 cefazolin Drugs 0.000 description 1
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 1
150000001780 cephalosporins Chemical class 0.000 description 1
QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
150000002989 phenols Chemical class 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
229910052697 platinum Inorganic materials 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
150000003475 thallium Chemical class 0.000 description 1
ZLUSCZLCHQSJRU-UHFFFAOYSA-N thallium(1+) Chemical class [Tl+] ZLUSCZLCHQSJRU-UHFFFAOYSA-N 0.000 description 1
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1

Classifications

- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DE19772747350 1976-10-22 1977-10-21 Clavulansaeureanaloge, deren salze und ester und verfahren zu deren herstellung Withdrawn DE2747350A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB44033/76A GB1593275A (en)	1976-10-22	1976-10-22	Clavam derivatives

Publications (1)

Publication Number	Publication Date
DE2747350A1 true DE2747350A1 (de)	1978-04-27

Family

ID=10431452

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19772747350 Withdrawn DE2747350A1 (de)	1976-10-22	1977-10-21	Clavulansaeureanaloge, deren salze und ester und verfahren zu deren herstellung

Country Status (6)

Country	Link
JP (1)	JPS5368797A (fr)
BE (1)	BE859979A (fr)
DE (1)	DE2747350A1 (fr)
FR (1)	FR2368489A1 (fr)
GB (1)	GB1593275A (fr)
NL (1)	NL7711577A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0024372A1 (fr) *	1979-08-03	1981-03-04	Beecham Group Plc	Dérivés de l'acide clavulanique, leur préparation et compositions pharmaceutiques les contenant
EP0025287A1 (fr) *	1979-08-21	1981-03-18	Beecham Group Plc	Dérivés de l'acide clavulanique, leur préparation, compositions pharmaceutiques les contenant et leur préparation
EP0301394A1 (fr) *	1987-07-31	1989-02-01	Pfaendler, Hans Rudolf, Prof. Dr.	Acides oxapénèm-3-carboxyliques stables

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0080285A1 (fr) *	1981-11-25	1983-06-01	Beecham Group Plc	Composés thérapeutiques contenant des bêta-lactames
EP0080286A1 (fr) *	1981-11-25	1983-06-01	Beecham Group Plc	Composés antibactériens contenant des bêta-lactames, procédés pour leur préparation et leur application
WO1984003282A1 (fr) *	1983-02-23	1984-08-30	Beecham Group Plc	Derives de clavames

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1529913A (en) *	1976-02-04	1978-10-25	Beecham Group Ltd	Beta-lactam compounds

1976
- 1976-10-22 GB GB44033/76A patent/GB1593275A/en not_active Expired
1977
- 1977-10-21 JP JP12587077A patent/JPS5368797A/ja active Pending
- 1977-10-21 DE DE19772747350 patent/DE2747350A1/de not_active Withdrawn
- 1977-10-21 BE BE181949A patent/BE859979A/fr unknown
- 1977-10-21 FR FR7731770A patent/FR2368489A1/fr not_active Withdrawn
- 1977-10-21 NL NL7711577A patent/NL7711577A/xx not_active Application Discontinuation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0024372A1 (fr) *	1979-08-03	1981-03-04	Beecham Group Plc	Dérivés de l'acide clavulanique, leur préparation et compositions pharmaceutiques les contenant
EP0025287A1 (fr) *	1979-08-21	1981-03-18	Beecham Group Plc	Dérivés de l'acide clavulanique, leur préparation, compositions pharmaceutiques les contenant et leur préparation
EP0301394A1 (fr) *	1987-07-31	1989-02-01	Pfaendler, Hans Rudolf, Prof. Dr.	Acides oxapénèm-3-carboxyliques stables
US5096899A (en) *	1987-07-31	1992-03-17	Bayer Aktiengesellschaft	Oxapenem-3-carboxylic acids

Also Published As

Publication number	Publication date
FR2368489A1 (fr)	1978-05-19
GB1593275A (en)	1981-07-15
JPS5368797A (en)	1978-06-19
BE859979A (fr)	1978-04-21
NL7711577A (nl)	1978-04-25

Publication	Publication Date	Title
DE2837264C2 (fr)	1991-06-13
DE3039504C2 (de)	1984-10-11	Derivate von 6&beta;-Hydroxyalkylpenicillansäuren und solche Derivate enthaltende Arzneimittel
DE2615693A1 (de)	1976-10-28	Antibakterielle mittel und verfahren zu ihrer herstellung
DD280533A5 (de)	1990-07-11	Verfahren zur herstellung von 3-trifluormethan-sulfonyloxy-3-cephem-zwischenverbindungen
DE2151567C2 (de)	1982-11-04	7-Amino-ceph-3-em-4-carbonsäure-Verbindungen und Verfahren zu ihrer Herstellung
DE2324272A1 (de)	1973-11-29	3-methylencephalosporine
DE2312041A1 (de)	1973-10-11	Penicilline, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
DE2747350A1 (de)	1978-04-27	Clavulansaeureanaloge, deren salze und ester und verfahren zu deren herstellung
DE2538801A1 (de)	1976-03-18	Cephalosporinderivate und verfahren zu ihrer herstellung
DE2311005A1 (de)	1973-10-31	Beta-lactamderivate, verfahren zu deren herstellung und sie enthaltende pharmazeutische mittel
CH648850A5 (de)	1985-04-15	Penicillansaeure-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel.
DE3008257A1 (de)	1980-09-11	Verfahren zur herstellung von penicillansaeure-1,1-dioxid und dessen estern sowie zwischenstufen zur durchfuehrung des verfahrens
DE2345236A1 (de)	1974-08-22	Quaternaere ammoniumverbindungen, verfahren zu deren herstellung und sie enthaltende arzneimittel
CH628055A5 (en)	1982-02-15	Process for the preparation of clavamic acid derivatives
CH639100A5 (de)	1983-10-31	Verfahren zur herstellung neuer beta-lactam antibiotika.
DE2600842C2 (fr)	1987-12-23
DE2657048A1 (de)	1977-06-23	Neue antibiotika
CH620444A5 (en)	1980-11-28	Process for the preparation of bicyclic unsaturated thiaaza compounds
DE2336344A1 (de)	1974-03-14	Penicillin- und cephalosporin-rsulfoxide, ihre salze und ester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2747599A1 (de)	1978-04-27	Clavulansaeurederivate, verfahren zu deren herstellung und diese enthaltende zusammensetzungen
DE3231596A1 (de)	1983-03-10	Penem-3-carbonsaeurederivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
DE69130363T2 (de)	1999-04-22	Antibakterielle penemverbindungen
CH616938A5 (en)	1980-04-30	Process for the preparation of 6beta-acylamino-1-oxadethiapenicillanic acids
DE3639542C2 (de)	1995-07-13	Carbamoyloxymethylalkylcarbapenem-Verbindungen
DE2302184C2 (de)	1982-04-01	6-[&alpha;-Aminocyclopropylacetamido]-penicillansäure, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneipräparate

Legal Events

Date	Code	Title	Description
1982-05-13	8139	Disposal/non-payment of the annual fee