NO852356L - Antibakterielle 7-okso-4-tia-1-azabisyklo-(3,2,0)hept-2-ene derivater. - Google Patents

Antibakterielle 7-okso-4-tia-1-azabisyklo-(3,2,0)hept-2-ene derivater.

Info

Publication number: NO852356L
Authority: NO; Norway
Prior art keywords: formula; group; compound; ester; stands
Prior art date: 1984-06-29

Application number

NO852356A

Other languages

English (en)

Norwegian (no)

Inventor

Barry Clive Ross

Michael David Cooke

Nicholas Iain Carruthers

Andrew John Barker

Original Assignee

Hoechst Uk 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.)

1984-06-29

Filing date

1985-06-11

Publication date

1985-12-30

1985-06-11 Application filed by Hoechst Uk Ltd filed Critical Hoechst Uk Ltd

1985-12-30 Publication of NO852356L publication Critical patent/NO852356L/no

Links

230000000844 anti-bacterial effect Effects 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 205
150000002148 esters Chemical class 0.000 claims description 82
-1 with an alcohol Chemical class 0.000 claims description 80
238000006243 chemical reaction Methods 0.000 claims description 67
150000003839 salts Chemical class 0.000 claims description 56
238000000034 method Methods 0.000 claims description 49
239000002253 acid Substances 0.000 claims description 48
125000004432 carbon atom Chemical group C* 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 27
239000002585 base Substances 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
150000001412 amines Chemical class 0.000 claims description 14
125000002843 carboxylic acid group Chemical group 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 13
125000004185 ester group Chemical group 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 12
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
230000009467 reduction Effects 0.000 claims description 10
230000007062 hydrolysis Effects 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
230000009471 action Effects 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
238000005660 chlorination reaction Methods 0.000 claims description 6
125000004494 ethyl ester group Chemical group 0.000 claims description 6
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 6
230000004962 physiological condition Effects 0.000 claims description 6
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
108090000371 Esterases Proteins 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001718 carbodiimides Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
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 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
238000006303 photolysis reaction Methods 0.000 claims description 5
230000015843 photosynthesis, light reaction Effects 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
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 claims description 2
GGHFOAXOFHKEMQ-UHFFFAOYSA-N 3-(3-carbamoylphenoxy)-6-(1-hydroxyethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C=1N2C(=O)C(C(O)C)C2SC=1OC1=CC=CC(C(N)=O)=C1 GGHFOAXOFHKEMQ-UHFFFAOYSA-N 0.000 claims description 2
MVTIDDWEBUVRRW-UHFFFAOYSA-N 3-(4-carbamoylphenoxy)-6-(1-hydroxyethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C=1N2C(=O)C(C(O)C)C2SC=1OC1=CC=C(C(N)=O)C=C1 MVTIDDWEBUVRRW-UHFFFAOYSA-N 0.000 claims description 2
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000005042 acyloxymethyl group Chemical group 0.000 claims description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
125000005633 phthalidyl group Chemical group 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
230000003213 activating effect Effects 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
239000000203 mixture Substances 0.000 description 105
239000000243 solution Substances 0.000 description 83
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
239000012044 organic layer Substances 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
238000004587 chromatography analysis Methods 0.000 description 27
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
239000000741 silica gel Substances 0.000 description 26
229910002027 silica gel Inorganic materials 0.000 description 26
239000002904 solvent Substances 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
239000012267 brine Substances 0.000 description 23
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000010828 elution Methods 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
235000015497 potassium bicarbonate Nutrition 0.000 description 9
229910000028 potassium bicarbonate Inorganic materials 0.000 description 9
239000011736 potassium bicarbonate Substances 0.000 description 9
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000005909 Kieselgur Substances 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
239000003480 eluent Substances 0.000 description 7
229960003975 potassium Drugs 0.000 description 7
239000011591 potassium Substances 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
230000008901 benefit Effects 0.000 description 5
PQPKPCPUSAPERC-UHFFFAOYSA-N ethyl acetate;formic acid;hexane Chemical compound OC=O.CCCCCC.CCOC(C)=O PQPKPCPUSAPERC-UHFFFAOYSA-N 0.000 description 5
238000004108 freeze drying Methods 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
PLUVDASVCADYIX-UHFFFAOYSA-N 2,2-dimethylpropanoyl bromide Chemical compound CC(C)(C)C(Br)=O PLUVDASVCADYIX-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 4
239000010502 orange oil Substances 0.000 description 4
150000002961 penems Chemical class 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
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SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
LSYBEKRLBPCVES-UHFFFAOYSA-N ethyl acetate formic acid Chemical compound C(C)(=O)OCC.C(=O)O.C(=O)O LSYBEKRLBPCVES-UHFFFAOYSA-N 0.000 description 1
LZPGAKXEPQTPJB-UHFFFAOYSA-N ethyl iodomethyl carbonate Chemical compound CCOC(=O)OCI LZPGAKXEPQTPJB-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
NZDJTVSTIFYISQ-UHFFFAOYSA-N iodomethyl acetate Chemical compound CC(=O)OCI NZDJTVSTIFYISQ-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
ANYSGBYRTLOUPO-UHFFFAOYSA-N lithium tetramethylpiperidide Chemical compound [Li]N1C(C)(C)CCCC1(C)C ANYSGBYRTLOUPO-UHFFFAOYSA-N 0.000 description 1
UPRXAOPZPSAYHF-UHFFFAOYSA-N lithium;cyclohexyl(propan-2-yl)azanide Chemical compound CC(C)N([Li])C1CCCCC1 UPRXAOPZPSAYHF-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
ZSVBYTJWYWOCJD-RNMHUYSQSA-N o-[(4-nitrophenyl)methyl] 2-[(2r,3s)-2-ethylsulfanyl-3-[(1r)-1-hydroxyethyl]-4-oxoazetidin-1-yl]-5,5-dimethyl-4-oxo-3-(4-phenylsulfanylcarbonylphenoxy)hex-2-enethioate Chemical compound CCS[C@@H]1[C@@H]([C@@H](C)O)C(=O)N1C(C(=S)OCC=1C=CC(=CC=1)[N+]([O-])=O)=C(C(=O)C(C)(C)C)OC1=CC=C(C(=O)SC=2C=CC=CC=2)C=C1 ZSVBYTJWYWOCJD-RNMHUYSQSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical group [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
PKRNTEFTZRPPFJ-UHFFFAOYSA-N prop-2-enethioyl 2,2-dimethylpropanoate Chemical compound CC(C(=O)OC(C=C)=S)(C)C PKRNTEFTZRPPFJ-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
229940071536 silver acetate Drugs 0.000 description 1
KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
SUGXYMLKALUNIU-UHFFFAOYSA-N silver;imidazol-3-ide Chemical compound [Ag+].C1=C[N-]C=N1 SUGXYMLKALUNIU-UHFFFAOYSA-N 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/90—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl and carboxyl groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO852356A 1984-06-29 1985-06-11 Antibakterielle 7-okso-4-tia-1-azabisyklo-(3,2,0)hept-2-ene derivater. NO852356L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB848416565A GB8416565D0 (en)	1984-06-29	1984-06-29	Antibacterial derivatives

Publications (1)

Publication Number	Publication Date
NO852356L true NO852356L (no)	1985-12-30

Family

ID=10563160

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
NO852356A NO852356L (no)	1984-06-29	1985-06-11	Antibakterielle 7-okso-4-tia-1-azabisyklo-(3,2,0)hept-2-ene derivater.
NO860974A NO860974L (no)	1984-06-29	1986-03-14	Mellomprodukt for fremstilling av terapeutisk virksomme 7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en derivater.
NO860975A NO860975L (no)	1984-06-29	1986-03-14	Mellomprodukt for fremstilling av terapeutisk virksomme 7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en derivater.

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
NO860974A NO860974L (no)	1984-06-29	1986-03-14	Mellomprodukt for fremstilling av terapeutisk virksomme 7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en derivater.
NO860975A NO860975L (no)	1984-06-29	1986-03-14	Mellomprodukt for fremstilling av terapeutisk virksomme 7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en derivater.

Country Status (17)

Country	Link
US (1)	US4795748A (hu)
EP (1)	EP0170028A1 (hu)
JP (1)	JPS6118760A (hu)
KR (1)	KR860000300A (hu)
AU (1)	AU583521B2 (hu)
DK (1)	DK296085A (hu)
ES (11)	ES8707963A1 (hu)
FI (1)	FI852554L (hu)
GB (2)	GB8416565D0 (hu)
GR (1)	GR851584B (hu)
HU (3)	HU196748B (hu)
IL (1)	IL75675A0 (hu)
NO (3)	NO852356L (hu)
NZ (1)	NZ212572A (hu)
PH (1)	PH22117A (hu)
PT (1)	PT80736B (hu)
ZA (1)	ZA854901B (hu)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2195627A (en) *	1986-08-12	1988-04-13	Hoechst Uk Ltd	Penem derivatives
DE3882730D1 (de) *	1987-02-11	1993-09-09	Ciba Geigy Ag	Bicyclische beta-lactam-carbonsaeuren.
AT392903B (de) *	1987-10-08	1991-07-10	Hoechst Ag	Pharmazeutische zubereitung enthaltend ein cephalosporin und ein penemantibiotikum
SE535691C2 (sv)	2011-03-08	2012-11-13	Kat2Biz Ab	Reduktion av C-O-bindningar via katalytisk transfer hydrogenolys
MX2015004636A (es) *	2012-10-12	2015-10-22	Lilly Co Eli	Motores químicos y métodos para su uso, especialmente en la inyección de fluidos altamente viscosos.
JP6841937B2 (ja)	2017-02-17	2021-03-10	イーライリリーアンドカンパニー	化学反応による流体の送達のためのプロセスおよびデバイス
CN111050826B (zh)	2017-09-08	2022-05-31	伊莱利利公司	用于控制药物递送装置内的气体生成的系统
AU2019402055B2 (en)	2018-12-19	2022-09-29	Eli Lilly And Company	Devices for delivery of therapeutic fluids

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4168314A (en) *	1977-11-17	1979-09-18	Merck & Co., Inc.	6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
JPS5625110A (en) *	1978-12-18	1981-03-10	Bristol Myers Co	Antibacterial
ES8305366A1 (es) *	1981-07-08	1983-04-01	Hoechst Uk Ltd	"procedimiento para la preparacion de derivados de penem".
EP0069378B1 (en) *	1981-07-08	1987-01-07	Hoechst Uk Limited	Antibacterial penem derivatives
KR900007181B1 (ko) *	1982-07-08	1990-09-29	훽스트 유케이 리미티드	펜엠 유도체의 제조방법
GB2164334B (en) *	1984-09-10	1988-08-03	Hoechst Uk Ltd	Antibacterial 7-oxo-4-thia-1-azabicyclo 3,2,0 hept-2-ene derivativess

1984
- 1984-06-29 GB GB848416565A patent/GB8416565D0/en active Pending
1985
- 1985-06-11 NO NO852356A patent/NO852356L/no unknown
- 1985-06-19 EP EP85107547A patent/EP0170028A1/en not_active Withdrawn
- 1985-06-24 HU HU855309A patent/HU196748B/hu unknown
- 1985-06-24 HU HU855310A patent/HU196809B/hu unknown
- 1985-06-24 HU HU852470A patent/HU194890B/hu not_active IP Right Cessation
- 1985-06-27 PH PH32465A patent/PH22117A/en unknown
- 1985-06-27 US US06/749,384 patent/US4795748A/en not_active Expired - Fee Related
- 1985-06-27 FI FI852554A patent/FI852554L/fi not_active Application Discontinuation
- 1985-06-27 GR GR851584A patent/GR851584B/el unknown
- 1985-06-27 NZ NZ212572A patent/NZ212572A/xx unknown
- 1985-06-27 ES ES544625A patent/ES8707963A1/es not_active Expired
- 1985-06-28 ZA ZA854901A patent/ZA854901B/xx unknown
- 1985-06-28 KR KR1019850004633A patent/KR860000300A/ko not_active Application Discontinuation
- 1985-06-28 IL IL75675A patent/IL75675A0/xx unknown
- 1985-06-28 AU AU44408/85A patent/AU583521B2/en not_active Expired - Fee Related
- 1985-06-28 PT PT80736A patent/PT80736B/pt unknown
- 1985-06-28 GB GB8516493A patent/GB2161161B/en not_active Expired
- 1985-06-28 JP JP60140707A patent/JPS6118760A/ja active Pending
- 1985-06-28 DK DK296085A patent/DK296085A/da not_active Application Discontinuation
1986
- 1986-02-01 ES ES551561A patent/ES9000004A1/es not_active Expired
- 1986-02-01 ES ES551562A patent/ES8801660A1/es not_active Expired
- 1986-03-14 NO NO860974A patent/NO860974L/no unknown
- 1986-03-14 NO NO860975A patent/NO860975L/no unknown
- 1986-09-29 ES ES557086A patent/ES8707539A1/es not_active Expired
- 1986-09-29 ES ES557092A patent/ES8800898A1/es not_active Expired
- 1986-09-29 ES ES557088A patent/ES8707496A1/es not_active Expired
- 1986-09-29 ES ES557087A patent/ES8707495A1/es not_active Expired
- 1986-09-29 ES ES557089A patent/ES8707540A1/es not_active Expired
- 1986-09-29 ES ES557091A patent/ES8707498A1/es not_active Expired
- 1986-09-29 ES ES557090A patent/ES8707497A1/es not_active Expired
1987
- 1987-05-13 ES ES557535A patent/ES8801661A1/es not_active Expired

Also Published As

Publication number	Publication date
ES8707498A1 (es)	1987-08-01
ES551562A0 (es)	1988-02-16
ES9000004A1 (es)	1988-12-16
ZA854901B (en)	1986-02-26
NO860974L (no)	1985-12-30
EP0170028A1 (en)	1986-02-05
ES557092A0 (es)	1987-12-01
US4795748A (en)	1989-01-03
HU194890B (en)	1988-03-28
ES557091A0 (es)	1987-08-01
ES557535A0 (es)	1988-02-16
GB8516493D0 (en)	1985-07-31
GB8416565D0 (en)	1984-08-01
PH22117A (en)	1988-06-01
HUT37942A (en)	1986-03-28
PT80736A (en)	1985-10-01
ES557088A0 (es)	1987-08-01
NO860975L (no)	1985-12-30
HU196748B (en)	1989-01-30
ES8707540A1 (es)	1987-08-01
ES8801660A1 (es)	1988-02-16
ES8707495A1 (es)	1987-08-01
PT80736B (en)	1987-03-17
GR851584B (hu)	1985-11-25
IL75675A0 (en)	1985-10-31
AU4440885A (en)	1986-01-02
ES557087A0 (es)	1987-08-01
AU583521B2 (en)	1989-05-04
ES544625A0 (es)	1987-09-01
ES557089A0 (es)	1987-08-01
ES557090A0 (es)	1987-08-01
ES8707539A1 (es)	1987-08-01
ES8800898A1 (es)	1987-12-01
FI852554A0 (fi)	1985-06-27
FI852554L (fi)	1985-12-30
ES551561A0 (es)	1988-12-16
ES8801661A1 (es)	1988-02-16
DK296085D0 (da)	1985-06-28
GB2161161A (en)	1986-01-08
ES8707963A1 (es)	1987-09-01
HU196809B (en)	1989-01-30
JPS6118760A (ja)	1986-01-27
GB2161161B (en)	1989-05-24
KR860000300A (ko)	1986-01-27
ES8707496A1 (es)	1987-08-01
NZ212572A (en)	1989-02-24
ES557086A0 (es)	1987-08-01
DK296085A (da)	1985-12-30
ES8707497A1 (es)	1987-08-01

Publication	Publication Date	Title
US4474793A (en)	1984-10-02	7-Oxo-4-thia-1-aza[3,2,0]heptane and 7-oxo-4-thia-1-aza[3,2,0]hept-2-ene derivatives
KR890001885B1 (ko)	1989-05-29	항균성 페넴 유도체의 제조방법
NO852356L (no)	1985-12-30	Antibakterielle 7-okso-4-tia-1-azabisyklo-(3,2,0)hept-2-ene derivater.
US4684640A (en)	1987-08-04	Antibacterial penem derivatives
KR900007181B1 (ko)	1990-09-29	펜엠 유도체의 제조방법
GB2092147A (en)	1982-08-11	Azabicycloheptene compounds
EP0031509B1 (en)	1984-10-24	Penem derivatives
NO860103L (no)	1986-03-11	Mellomprodukt for fremstilling av terapeutisk virksomme 7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en-derivater.
NO873353L (no)	1988-02-15	Fremgangsmaate for fremstilling av antibakterielle 7-okso-4-tia-1-azabicyklo(3.2.0)hept-2-en-derivater.
NO863304L (no)	1987-02-17	7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en-derivater.
GB2197864A (en)	1988-06-02	7-oxo-4-thia-1-azabicyclo(3,2,0)hept-2-ene derivatives
GB2197865A (en)	1988-06-02	Azetidinone derivatives
CS255871B2 (en)	1988-03-15	Process for preparing derivatives of 6-/1-acyl-1-hydrohymethyl/-penicillanic acid
US5200403A (en)	1993-04-06	Inhibition of βlactamase with 6 β-(substituted methyl)-penicillanic acid derivatives
IT9009393A1 (it)	1991-11-16	Penem ditiocarbammati, loro uso e procedimento di fabbricazione relativi
NO871933L (no)	1987-02-17	7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en-derivater.
NO871934L (no)	1987-02-17	7-okso-4-tia-1-azabicyklo(3,2,0)hept-2-en-derivater.
JPS6248687A (ja)	1987-03-03	７−オキソ−４−チア−１−アザビシクロ〔３．２．０〕ヘプト−２−エン誘導体
JPS63188684A (ja)	1988-08-04	７−オキソ−４−チア−１−アザビシクロ［３．２．０］ヘプト−２−エン誘導体の製造法
JPS6176492A (ja)	1986-04-18	７‐オキソ‐４チア‐１‐アザビシクロ〔３．２．０〕ヘプタ‐２‐エン誘導体