HU190716B - Process for preparing antibiotics containing carbapenemic skeleton - Google Patents

Process for preparing antibiotics containing carbapenemic skeleton Download PDF

Info

Publication number: HU190716B
Authority: HU; Hungary
Prior art keywords: formula; compounds; group; alkyl; compound
Prior art date: 1982-04-08

Application number

HU831201A

Other languages

English (en)

Hungarian (hu)

Inventor

Uen K Choung

Original Assignee

Bristol Myers Co

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.)

1982-04-08

Filing date

1983-04-07

Publication date

1986-10-28

1983-04-07 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1986-10-28 Publication of HU190716B publication Critical patent/HU190716B/hu

Links

239000003242 anti bacterial agent Substances 0.000 title abstract description 5
229940088710 antibiotic agent Drugs 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 17
238000002360 preparation method Methods 0.000 claims abstract description 16
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 94
125000004432 carbon atom Chemical group C* 0.000 claims description 46
-1 silver ions Chemical class 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 15
150000001450 anions Chemical group 0.000 claims description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 6
125000000129 anionic group Chemical group 0.000 claims description 6
229910052709 silver Inorganic materials 0.000 claims description 5
239000004332 silver Substances 0.000 claims description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 3
229940006461 iodide ion Drugs 0.000 claims description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
230000001681 protective effect Effects 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
239000000463 material Substances 0.000 claims 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 18
125000000623 heterocyclic group Chemical group 0.000 abstract description 16
125000001072 heteroaryl group Chemical group 0.000 abstract description 13
125000001931 aliphatic group Chemical group 0.000 abstract description 6
230000003389 potentiating effect Effects 0.000 abstract description 6
229910052717 sulfur Inorganic materials 0.000 abstract description 6
239000011593 sulfur Substances 0.000 abstract description 5
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 abstract 1
150000003463 sulfur Chemical class 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 description 33
BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical group OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 29
239000000543 intermediate Substances 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
150000002431 hydrogen Chemical class 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
125000002252 acyl group Chemical group 0.000 description 14
239000000243 solution Substances 0.000 description 14
241000699670 Mus sp. Species 0.000 description 13
125000003342 alkenyl group Chemical group 0.000 description 13
125000003710 aryl alkyl group Chemical group 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
125000000753 cycloalkyl group Chemical group 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
125000000304 alkynyl group Chemical group 0.000 description 10
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
239000000203 mixture Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 8
ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000588724 Escherichia coli Species 0.000 description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
244000005700 microbiome Species 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
125000000392 cycloalkenyl group Chemical group 0.000 description 6
238000010790 dilution Methods 0.000 description 6
239000012895 dilution Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 5
238000009472 formulation Methods 0.000 description 5
125000002950 monocyclic group Chemical group 0.000 description 5
241000894006 Bacteria Species 0.000 description 4
241000421809 Brisaster fragilis Species 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
125000004043 oxo group Chemical group O=* 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
241000588697 Enterobacter cloacae Species 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
241000606768 Haemophilus influenzae Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
238000007917 intracranial administration Methods 0.000 description 3
238000007918 intramuscular administration Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000000547 substituted alkyl group Chemical group 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
238000011282 treatment Methods 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000588772 Morganella morganii Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
244000038458 Nepenthes mirabilis Species 0.000 description 2
244000110797 Polygonum persicaria Species 0.000 description 2
241000607715 Serratia marcescens Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
241000894007 species Species 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
238000006257 total synthesis reaction Methods 0.000 description 2
230000036325 urinary excretion Effects 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
238000005406 washing Methods 0.000 description 2
150000003952 β-lactams Chemical class 0.000 description 2
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 1
BSIMZHVOQZIAOY-UHFFFAOYSA-N 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCC2CC(=O)N12 BSIMZHVOQZIAOY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
125000005865 C2-C10alkynyl group Chemical group 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000588777 Providencia rettgeri Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
241001147855 Streptomyces cattleya Species 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
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238000005917 acylation reaction Methods 0.000 description 1
125000005041 acyloxyalkyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
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230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
125000005135 aryl sulfinyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
102000006635 beta-lactamase Human genes 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036765 blood level Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
230000007073 chemical hydrolysis Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229920001577 copolymer Chemical group 0.000 description 1
238000012258 culturing Methods 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000003113 dilution method Methods 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
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
FQQFFZPBGYGDSX-NJFHWYBASA-N epithienamycin E Chemical compound C1C(S\C=C\NC(C)=O)=C(C(O)=O)N2C(=O)[C@@H]([C@@H](OS(O)(=O)=O)C)[C@H]21 FQQFFZPBGYGDSX-NJFHWYBASA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
238000007429 general method Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
229960002182 imipenem Drugs 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
208000037797 influenza A Diseases 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000011068 loading method Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
239000005445 natural material Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000003973 paint Substances 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229940100890 silver compound Drugs 0.000 description 1
150000003379 silver compounds Chemical class 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000017105 transposition Effects 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
- 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)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (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 Condensed Heterocyclic Rings (AREA)

HU831201A 1982-04-08 1983-04-07 Process for preparing antibiotics containing carbapenemic skeleton HU190716B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US36662782A	1982-04-08	1982-04-08

Publications (1)

Publication Number	Publication Date
HU190716B true HU190716B (en)	1986-10-28

Family

ID=23443823

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU831201A HU190716B (en)	1982-04-08	1983-04-07	Process for preparing antibiotics containing carbapenemic skeleton

Country Status (25)

Country	Link
JP (1)	JPS58188887A (fr)
KR (1)	KR880001055B1 (fr)
AT (1)	AT383126B (fr)
AU (1)	AU567092B2 (fr)
BE (1)	BE896407A (fr)
CA (1)	CA1198440A (fr)
CH (1)	CH661927A5 (fr)
DE (1)	DE3312517A1 (fr)
DK (1)	DK155983A (fr)
ES (1)	ES8405399A1 (fr)
FI (1)	FI74009C (fr)
FR (1)	FR2524888B1 (fr)
GB (1)	GB2118183B (fr)
GR (1)	GR78822B (fr)
HU (1)	HU190716B (fr)
IE (1)	IE55225B1 (fr)
IL (1)	IL68295A0 (fr)
IT (1)	IT1168854B (fr)
LU (1)	LU84739A1 (fr)
MY (1)	MY8700945A (fr)
NL (1)	NL8301193A (fr)
OA (1)	OA07395A (fr)
PT (1)	PT76518B (fr)
SE (1)	SE460197B (fr)
ZA (1)	ZA832411B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4683301A (en) *	1982-04-08	1987-07-28	Bristol-Myers Company	Carbapenem antibiotics
US4552696A (en) *	1982-04-09	1985-11-12	Bristol-Myers Company	Carbapenem antibiotics
US4536335A (en) *	1982-06-18	1985-08-20	Bristol-Myers Company	Carbapenem antibiotics
AT396473B (de) *	1984-10-02	1993-09-27	Bristol Myers Squibb Co	Verfahren zur herstellung von neuen carbapenemderivaten
US4665169A (en) *	1985-09-11	1987-05-12	Bristol-Myers Company	Carbapenem antibiotics

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU531084B2 (en) *	1977-10-19	1983-08-11	Merck & Co., Inc.	Azetidine derivatives
EP0017992A1 (fr) *	1979-04-19	1980-10-29	Merck & Co. Inc.	Acides 1-carbadéthiapén-2-èm-carboxyliques substitués en position 2 et 6, procédés pour les préparer, compositions pharmaceutiques antibiotiques les contenant et procédé pour préparer des intermédiaires
EP0038869A1 (fr) *	1980-04-30	1981-11-04	Merck & Co. Inc.	Procédé de préparation de 1-carbapénèmes et intermédiaires pour leur préparation
HU185493B (en) *	1981-12-30	1985-02-28	Richter Gedeon Vegyeszet	Process for producing new azabicyclo-bracket-3.2.0-bracket closedheptene derivatives
US4552696A (en) *	1982-04-09	1985-11-12	Bristol-Myers Company	Carbapenem antibiotics
US4536335A (en) *	1982-06-18	1985-08-20	Bristol-Myers Company	Carbapenem antibiotics

1983
- 1983-03-22 CA CA000424190A patent/CA1198440A/fr not_active Expired
- 1983-04-01 FR FR8305431A patent/FR2524888B1/fr not_active Expired
- 1983-04-04 KR KR1019830001386A patent/KR880001055B1/ko not_active IP Right Cessation
- 1983-04-05 NL NL8301193A patent/NL8301193A/nl not_active Application Discontinuation
- 1983-04-05 IL IL68295A patent/IL68295A0/xx not_active IP Right Cessation
- 1983-04-05 ES ES521224A patent/ES8405399A1/es not_active Expired
- 1983-04-05 ZA ZA832411A patent/ZA832411B/xx unknown
- 1983-04-05 FI FI831135A patent/FI74009C/fi not_active IP Right Cessation
- 1983-04-06 AU AU13198/83A patent/AU567092B2/en not_active Ceased
- 1983-04-07 PT PT76518A patent/PT76518B/pt not_active IP Right Cessation
- 1983-04-07 SE SE8301928A patent/SE460197B/sv not_active IP Right Cessation
- 1983-04-07 BE BE0/210512A patent/BE896407A/fr not_active IP Right Cessation
- 1983-04-07 GR GR71026A patent/GR78822B/el unknown
- 1983-04-07 IT IT48061/83A patent/IT1168854B/it active
- 1983-04-07 LU LU84739A patent/LU84739A1/fr unknown
- 1983-04-07 GB GB08309505A patent/GB2118183B/en not_active Expired
- 1983-04-07 DE DE19833312517 patent/DE3312517A1/de active Granted
- 1983-04-07 DK DK155983A patent/DK155983A/da not_active IP Right Cessation
- 1983-04-07 HU HU831201A patent/HU190716B/hu unknown
- 1983-04-07 IE IE800/83A patent/IE55225B1/en not_active IP Right Cessation
- 1983-04-08 AT AT0125583A patent/AT383126B/de not_active IP Right Cessation
- 1983-04-08 OA OA57966A patent/OA07395A/fr unknown
- 1983-04-08 JP JP58061072A patent/JPS58188887A/ja active Granted
- 1983-04-08 CH CH1915/83A patent/CH661927A5/de not_active IP Right Cessation
1987
- 1987-12-30 MY MY945/87A patent/MY8700945A/xx unknown

Also Published As

Publication number	Publication date
PT76518B (en)	1986-02-06
IE55225B1 (en)	1990-07-04
AU567092B2 (en)	1987-11-12
IT8348061A0 (it)	1983-04-07
OA07395A (fr)	1984-06-30
JPS58188887A (ja)	1983-11-04
AU1319883A (en)	1983-10-13
DK155983A (da)	1983-10-09
DE3312517C2 (fr)	1991-10-31
IT1168854B (it)	1987-05-20
BE896407A (fr)	1983-10-07
ES521224A0 (es)	1984-06-01
GB2118183A (en)	1983-10-26
KR880001055B1 (ko)	1988-06-18
ATA125583A (de)	1986-10-15
CA1198440A (fr)	1985-12-24
IL68295A0 (en)	1983-07-31
FI74009C (fi)	1987-12-10
SE460197B (sv)	1989-09-18
FR2524888A1 (fr)	1983-10-14
FI74009B (fi)	1987-08-31
SE8301928L (sv)	1983-12-02
FR2524888B1 (fr)	1985-12-13
DK155983D0 (da)	1983-04-07
MY8700945A (en)	1987-12-31
NL8301193A (nl)	1983-11-01
PT76518A (en)	1983-05-01
CH661927A5 (de)	1987-08-31
KR840004429A (ko)	1984-10-15
FI831135A0 (fi)	1983-04-05
IE830800L (en)	1983-10-08
GB8309505D0 (en)	1983-05-11
DE3312517A1 (de)	1983-10-20
SE8301928D0 (sv)	1983-04-07
JPH0524156B2 (fr)	1993-04-06
ES8405399A1 (es)	1984-06-01
FI831135L (fi)	1983-10-09
GR78822B (fr)	1984-10-02
GB2118183B (en)	1985-11-27
ZA832411B (en)	1983-12-28
LU84739A1 (fr)	1983-12-05
AT383126B (de)	1987-05-25

Publication	Publication Date	Title
EP0072710B1 (fr)	1986-02-19	Dérivés de Carbapénème, leur préparation et compositions les contenant
CZ286878B6 (en)	2000-07-12	Carbapenems, process of their preparation, intermediates for their preparation, those carbapenems used for treating infections and pharmaceutical preparations
EP0597821A1 (fr)	1994-05-18	Dérivés de (hétérocyclylthio)-2-carbapénème, leur préparation et application comme antibiotiques
HU196800B (en)	1989-01-30	Process for producing carbepeneme derivatives and pharmaceutical compositions containing them as active component
US4536335A (en)	1985-08-20	Carbapenem antibiotics
HU201762B (en)	1990-12-28	Process for producing 3-pyrrolidinylthio-1-azobicyclo(3.2.0)hept-2-en-2-carboxylic acid derivatives
KR100589030B1 (ko)	2006-06-13	카르바페넴 유도체, 그 사용 방법 및 그 중간체 화합물
SI9600371A (sl)	1998-06-30	Etilidenski derivati tricikličnih karbapenemov
HU190083B (en)	1986-08-28	Process for preparing carbapenem derivatives
RU2247725C2 (ru)	2005-03-10	Производные 1-метилкарбапенема
KR890002228B1 (ko)	1989-06-24	카르바페넴 유도체 및 그의 제조방법
NL8101039A (nl)	1981-10-01	7-oxo-1-azabicyclo3,2,0 hept-2-een-2-carbonzuurverbindingen, hun gebruik en bereiding.
HU190716B (en)	1986-10-28	Process for preparing antibiotics containing carbapenemic skeleton
DE69120572T2 (de)	1997-01-09	Carbapenem-Derivate, in 2-Stellung substituiert mit substituierten Pyrrolidinylthio-Gruppen
KR100530478B1 (ko)	2005-11-23	카르바페넴 화합물, 이의 용도 및 이의 중간체 화합물
FI81577C (fi)	1990-11-12	Foerfarande foer framstaellning av som laekemedel anvaendbara 2-(2-substituerad-2-iminoetyltio)-6-(1-hydroxietyl)- 1-karbapen -2-em-3-karboxylsyror.
DE69523058T2 (de)	2002-02-07	Carbapenem-derivate
KR910009270B1 (ko)	1991-11-08	카바펜엠 항생제의 제조방법
CS259892B2 (en)	1988-11-15	Method of 6-(1-hydroxyethyl)-7-oxo-1-azabiclo/3,2,o/hept-en-2-carboxyl acid's derivatives production
GB2183237A (en)	1987-06-03	Carbapenem antibiotics
DE2448582A1 (de)	1975-06-19	Verfahren zur herstellung von cephalosporinen
JP2003183282A (ja)	2003-07-03	カルバペネム化合物
EP0050927A1 (fr)	1982-05-05	La préparation de bêta-lactames antibiotiques
JPH0429675B2 (fr)	1992-05-19
WO1995014692A1 (fr)	1995-06-01	Derives de carbapenem et leurs procedes de preparation

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628