NO832001L - Fremgangsmaate ved fremstilling av 1-sulfo-2-okso-azetidinderivater - Google Patents

Fremgangsmaate ved fremstilling av 1-sulfo-2-okso-azetidinderivater

Info

Publication number: NO832001L
Authority: NO; Norway
Prior art keywords: amino; alkyl; oxo; thiazolyl; group
Prior art date: 1982-06-03

Application number

NO832001A

Other languages

English (en)

Norwegian (no)

Inventor

Werner Hofheinz

Andre Furlenmeier

Hans Peter Isenring

Christian Nicolas Hubschwerlen

Original Assignee

Hoffmann La Roche

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.)

1982-06-03

Filing date

1983-06-02

Publication date

1983-12-05

1983-06-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1983-12-05 Publication of NO832001L publication Critical patent/NO832001L/no

Links

238000000034 method Methods 0.000 title claims description 44
CDFGMYLBUSYTKQ-UHFFFAOYSA-N 2-oxoazetidine-1-sulfonic acid Chemical class OS(=O)(=O)N1CCC1=O CDFGMYLBUSYTKQ-UHFFFAOYSA-N 0.000 title claims description 7
-1 5- or 6-membered Chemical group 0.000 claims abstract description 164
150000001875 compounds Chemical class 0.000 claims abstract description 84
150000003839 salts Chemical class 0.000 claims abstract description 54
125000000217 alkyl group Chemical group 0.000 claims abstract description 35
150000002148 esters Chemical class 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 17
125000003277 amino group Chemical group 0.000 claims abstract description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 81
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 79
239000007858 starting material Substances 0.000 claims description 43
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 41
238000006243 chemical reaction Methods 0.000 claims description 40
239000000047 product Substances 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 31
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
150000007970 thio esters Chemical class 0.000 claims description 13
239000007795 chemical reaction product Substances 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
XVAYDLJEBGHLSX-GBXIJSLDSA-N (2s,3s)-3-amino-2-(carbamoyloxymethyl)-4-oxoazetidine-1-sulfonic acid Chemical compound N[C@H]1[C@@H](COC(N)=O)N(S(O)(=O)=O)C1=O XVAYDLJEBGHLSX-GBXIJSLDSA-N 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
125000004185 ester group Chemical group 0.000 claims description 5
NKFMHVSOHCEONZ-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetamide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)N)C1=CC=CC=C1 NKFMHVSOHCEONZ-UHFFFAOYSA-N 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 6
150000001539 azetidines Chemical class 0.000 claims 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 2
150000007524 organic acids Chemical class 0.000 claims 2
230000000845 anti-microbial effect Effects 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 169
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 162
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 156
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 138
229910001868 water Inorganic materials 0.000 description 131
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 127
239000000243 solution Substances 0.000 description 122
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 105
238000005481 NMR spectroscopy Methods 0.000 description 65
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
235000019439 ethyl acetate Nutrition 0.000 description 54
238000003756 stirring Methods 0.000 description 49
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 44
239000011541 reaction mixture Substances 0.000 description 43
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
125000001841 imino group Chemical group [H]N=* 0.000 description 39
230000002829 reductive effect Effects 0.000 description 37
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 36
230000008018 melting Effects 0.000 description 36
238000002844 melting Methods 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 34
239000002904 solvent Substances 0.000 description 34
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
239000013078 crystal Substances 0.000 description 27
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
238000001704 evaporation Methods 0.000 description 23
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
238000000921 elemental analysis Methods 0.000 description 22
235000017557 sodium bicarbonate Nutrition 0.000 description 21
229910000030 sodium bicarbonate Inorganic materials 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 19
239000000725 suspension Substances 0.000 description 19
239000003480 eluent Substances 0.000 description 18
239000012071 phase Substances 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
239000003054 catalyst Substances 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 17
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 17
230000008020 evaporation Effects 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
238000001035 drying Methods 0.000 description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
238000001816 cooling Methods 0.000 description 13
239000000499 gel Substances 0.000 description 13
239000003960 organic solvent Substances 0.000 description 13
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
239000011734 sodium Substances 0.000 description 11
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 11
238000004108 freeze drying Methods 0.000 description 10
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
150000007530 organic bases Chemical class 0.000 description 8
230000002441 reversible effect Effects 0.000 description 8
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 5
KHUNFTAJVUPPCY-UHFFFAOYSA-N azetidine-1-sulfonic acid Chemical compound OS(=O)(=O)N1CCC1 KHUNFTAJVUPPCY-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 5
DUPBILVWMPJNKH-UHFFFAOYSA-N pyridine;sulfur dioxide Chemical compound O=S=O.C1=CC=NC=C1 DUPBILVWMPJNKH-UHFFFAOYSA-N 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
HGNLFHAIJFSFEC-DMTCNVIQSA-N (2r,3s)-3-amino-2-ethynyl-4-oxoazetidine-1-sulfonic acid Chemical compound N[C@H]1[C@@H](C#C)N(S(O)(=O)=O)C1=O HGNLFHAIJFSFEC-DMTCNVIQSA-N 0.000 description 4
YEXUKJOCDUCFNK-VXKWHMMOSA-N (3s,4s)-4-ethynyl-3-(tritylamino)azetidin-2-one Chemical compound O=C1N[C@@H](C#C)[C@@H]1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YEXUKJOCDUCFNK-VXKWHMMOSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 4
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
QSMGUTWCBAOBCD-UHFFFAOYSA-M sodium azetidine-1-sulfonate Chemical compound [Na+].N1(CCC1)S(=O)(=O)[O-] QSMGUTWCBAOBCD-UHFFFAOYSA-M 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
ZUYRWQOQZXOGET-DMTCNVIQSA-N (2S,3S)-3-amino-2-(methoxyiminomethyl)-4-oxoazetidine-1-sulfonic acid Chemical compound CON=C[C@@H]1[C@H](N)C(=O)N1S(O)(=O)=O ZUYRWQOQZXOGET-DMTCNVIQSA-N 0.000 description 3
PTBAVHOIUFBPKD-HCWXCVPCSA-N (2s,3s)-3-amino-2-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-oxoazetidine-1-sulfonic acid Chemical compound O1C(C)(C)OC[C@H]1[C@H]1N(S(O)(=O)=O)C(=O)[C@H]1N PTBAVHOIUFBPKD-HCWXCVPCSA-N 0.000 description 3
FHSVXTNWSNNOLT-YADHBBJMSA-N (3s,4r)-4-ethenyl-3-(tritylamino)azetidin-2-one Chemical compound C=C[C@H]1NC(=O)[C@H]1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FHSVXTNWSNNOLT-YADHBBJMSA-N 0.000 description 3
JEFBHIVPSVBWOV-PKTZIBPZSA-N (3s,4r)-4-propyl-3-(tritylamino)azetidin-2-one Chemical compound CCC[C@H]1NC(=O)[C@H]1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JEFBHIVPSVBWOV-PKTZIBPZSA-N 0.000 description 3
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239000011707 mineral Substances 0.000 description 1
NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
235000021395 porridge Nutrition 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
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
235000019394 potassium persulphate Nutrition 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011697 sodium iodate Substances 0.000 description 1
235000015281 sodium iodate Nutrition 0.000 description 1
229940032753 sodium iodate Drugs 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
JVKDHPFQMHOYQK-GWHWORMBSA-M sodium;(2r,3r)-2-[(e)-3-amino-3-oxoprop-1-enyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxoazetidine-1-sulfonate Chemical compound [Na+].CC(C)(C)OC(=O)N[C@@H]1[C@@H](\C=C\C(N)=O)N(S([O-])(=O)=O)C1=O JVKDHPFQMHOYQK-GWHWORMBSA-M 0.000 description 1
WPPPJPRAQQWDLC-HNJRQZNRSA-M sodium;(2r,3s)-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-ethenyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=NOC)C(=O)N[C@H]1[C@@H](C=C)N(S([O-])(=O)=O)C1=O WPPPJPRAQQWDLC-HNJRQZNRSA-M 0.000 description 1
MIXGOOFOPYJAFD-OTWOCUTASA-M sodium;(2s,3s)-3-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-formyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=N/OC)/C(=O)N[C@H]1[C@@H](C=O)N(S([O-])(=O)=O)C1=O MIXGOOFOPYJAFD-OTWOCUTASA-M 0.000 description 1
VSNMUZAGYUXMEY-MUWMCQJSSA-M sodium;(2s,3s)-3-amino-2-(carbamoyloxymethyl)-4-oxoazetidine-1-sulfonate Chemical compound [Na+].N[C@H]1[C@@H](COC(N)=O)N(S([O-])(=O)=O)C1=O VSNMUZAGYUXMEY-MUWMCQJSSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
PPDWIVUCWRYPPC-JBRJIWJGSA-N tert-butyl n-[(2s,3r)-2-[(e)-3-amino-3-oxoprop-1-enyl]-1-[(2,4-dimethoxyphenyl)methyl]-4-oxoazetidin-3-yl]carbamate Chemical compound COC1=CC(OC)=CC=C1CN1C(=O)[C@H](NC(=O)OC(C)(C)C)[C@@H]1\C=C\C(N)=O PPDWIVUCWRYPPC-JBRJIWJGSA-N 0.000 description 1
SBOVKKFBEPSWRA-KIEHPGSMSA-N tert-butyl n-[(2s,3r)-2-[(e)-3-amino-3-oxoprop-1-enyl]-4-oxoazetidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1[C@H](\C=C\C(N)=O)NC1=O SBOVKKFBEPSWRA-KIEHPGSMSA-N 0.000 description 1
SXBAXOWGUYAQRZ-WDSOQIARSA-N tert-butyl n-[(2s,3s)-1-[(2,4-dimethoxyphenyl)methyl]-2-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]azetidin-3-yl]carbamate Chemical compound COC1=CC(OC)=CC=C1CN1[C@H]([C@H]2OC(C)(C)OC2)[C@@H](NC(=O)OC(C)(C)C)C1 SXBAXOWGUYAQRZ-WDSOQIARSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- 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
- C07D205/085—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 nitrogen atom directly attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

NO832001A 1982-06-03 1983-06-02 Fremgangsmaate ved fremstilling av 1-sulfo-2-okso-azetidinderivater NO832001L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH341682		1982-06-03
CH341782		1982-06-03
CH220183		1983-04-25

Publications (1)

Publication Number	Publication Date
NO832001L true NO832001L (no)	1983-12-05

Family

ID=27173519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO832001A NO832001L (no)	1982-06-03	1983-06-02	Fremgangsmaate ved fremstilling av 1-sulfo-2-okso-azetidinderivater

Country Status (14)

Country	Link
EP (1)	EP0096297B1 (fr)
AU (1)	AU558593B2 (fr)
DE (1)	DE3377061D1 (fr)
DK (1)	DK241883A (fr)
ES (2)	ES522886A0 (fr)
FI (1)	FI832004L (fr)
GR (1)	GR78269B (fr)
IE (1)	IE55402B1 (fr)
IL (1)	IL68817A (fr)
MC (1)	MC1527A1 (fr)
NO (1)	NO832001L (fr)
NZ (1)	NZ204386A (fr)
PH (2)	PH18877A (fr)
PT (1)	PT76809A (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MA19602A1 (fr) *	1981-09-30	1983-04-01	Ciba Geigy Ag	Composes d'amino-oxazolyle, procede pour leur preparation, preparations pharmaceutiques qui contiennent ces composes, et leur application
AU564150B2 (en) *	1982-04-30	1987-08-06	Takeda Chemical Industries Ltd.	1-sulfo-2-azetidinone derivatives
CA1263399A (fr) *	1984-12-19	1989-11-28	Hoffmann-La Roche Limited	Methode de preparation de derives d'acide aminothiazolacetique
US4883869A (en) *	1984-12-20	1989-11-28	The Upjohn Company	Novel beta-lactams containing amino acid substituents
US4837318A (en) *	1985-05-09	1989-06-06	The Upjohn Company	Carbonate substituted monobactams as antibiotics
WO1986006722A1 (fr) *	1985-05-09	1986-11-20	The Upjohn Company	Monobactames substitues par du carbonate servant d'antibiotiques
US4675398A (en) *	1985-08-16	1987-06-23	E. R. Squibb & Sons, Inc.	Copper-mediated oximation reaction
US4684722A (en) *	1986-01-06	1987-08-04	E. R. Squibb & Sons, Inc.	Monosulfactams
SI8711089A8 (en) *	1987-06-11	1996-08-31	Krka Tovarna Zdravil	Process for preparation of 6-/d(-)-alpha-(4-ethyl-2,3-dioxo-1- piperazine-carboxyamido)-phenylacetamido/-penicillanic acid
US5015737A (en) *	1987-07-22	1991-05-14	The Upjohn Company	Therapeutically useful beta-lactams
WO1992007840A1 (fr) *	1990-11-02	1992-05-14	Taisho Pharmaceutical Co., Ltd.	Derive de thioester de thiazole
AT402928B (de) *	1994-12-23	1997-09-25	Biochemie Gmbh	Neues verfahren zur herstellung von cefotaxim
AT406773B (de) *	1998-04-02	2000-08-25	Biochemie Gmbh	Neues salz von 7-(2-(aminothiazol-4yl)-2-
US8242153B2 (en)	2008-07-24	2012-08-14	Hoffmann-La Roche Inc.	4,5-dihydro-oxazol-2YL derivatives
BRPI0916363A2 (pt) *	2008-07-24	2018-05-29	Hoffmann La Roche	derivados de 4,5-di-hidro-oxazol-2-ila
EP3511328B1 (fr)	2014-03-24	2021-03-03	Novartis AG	Composés organiques de la famille des monobactams pour le traitement d'infections bactériennes
PT3353175T (pt)	2015-09-23	2020-09-10	Novartis Ag	Sais e formas sólidas de um antibiótico monobactâmico
CN111094281B (zh)	2017-08-02	2023-08-29	诺华股份有限公司	用于制备单内酰胺抗生素的化学方法及其中间体

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0009008A3 (fr) *	1978-09-08	1980-05-14	Ciba-Geigy Ag	Dérivés de céphalosporine, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0021678B1 (fr) *	1979-06-08	1984-11-07	Takeda Chemical Industries, Ltd.	Dérivés de 1-sulfo-2-azétidinone, leur préparation et leurs compositions pharmaceutiques
NZ196202A (en) *	1980-02-07	1984-07-31	Squibb & Sons Inc	Beta-lactam antibiotics (of azetidine-sulphonic acid type)
EP0037380B1 (fr) *	1980-03-28	1984-09-12	BIOCHEMIE Gesellschaft m.b.H.	Procédé pour la production d'antibiotiques du type céphalosporine, intermédiaires pour utilisation dans ce procédé et leur production
WO1982001873A1 (fr) *	1980-12-05	1982-06-10	Takeda Chemical Industries Ltd	Derives 1-sulfo-2-oxoazetidine et leur procede de preparation
EP0059683A3 (fr) *	1981-02-27	1982-12-01	Ciba-Geigy Ag	Acides 7-acylamido-3-céphem-4 carboxyliques, leur préparation, compositions pharmaceutiques les contenant et leur application
EP0075104A3 (fr) *	1981-09-23	1984-11-28	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Dérivés de céphalosporine, procédé pour leur préparation, compositions pharmaceutiques et intermédiaires
MA19602A1 (fr) *	1981-09-30	1983-04-01	Ciba Geigy Ag	Composes d'amino-oxazolyle, procede pour leur preparation, preparations pharmaceutiques qui contiennent ces composes, et leur application
US4379787A (en) *	1981-10-02	1983-04-12	Eli Lilly And Company	Oximino-substituted cephalosporin compounds
FR2515182B1 (fr) *	1981-10-23	1986-05-09	Roussel Uclaf	Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine 1-sulfamique, leur procede de preparation, leur application comme medicaments et les produits intermediaires necessaires a leur preparation

1983
- 1983-05-25 EP EP83105155A patent/EP0096297B1/fr not_active Expired
- 1983-05-25 DE DE8383105155T patent/DE3377061D1/de not_active Expired
- 1983-05-27 DK DK241883A patent/DK241883A/da not_active Application Discontinuation
- 1983-05-27 NZ NZ204386A patent/NZ204386A/en unknown
- 1983-05-30 AU AU15068/83A patent/AU558593B2/en not_active Ceased
- 1983-05-30 IL IL68817A patent/IL68817A/xx unknown
- 1983-06-01 GR GR71525A patent/GR78269B/el unknown
- 1983-06-01 MC MC831639A patent/MC1527A1/fr unknown
- 1983-06-01 ES ES522886A patent/ES522886A0/es active Granted
- 1983-06-02 IE IE1305/83A patent/IE55402B1/en not_active IP Right Cessation
- 1983-06-02 PH PH29003A patent/PH18877A/en unknown
- 1983-06-02 NO NO832001A patent/NO832001L/no unknown
- 1983-06-03 PT PT76809A patent/PT76809A/pt unknown
- 1983-06-03 FI FI832004A patent/FI832004L/fi not_active Application Discontinuation
1984
- 1984-02-16 ES ES529774A patent/ES8601123A1/es not_active Expired
1985
- 1985-01-17 PH PH31733A patent/PH21897A/en unknown

Also Published As

Publication number	Publication date
AU558593B2 (en)	1987-02-05
ES8504120A1 (es)	1985-04-16
IE831305L (en)	1983-12-05
MC1527A1 (fr)	1984-04-13
ES522886A0 (es)	1985-04-16
PH18877A (en)	1985-10-22
NZ204386A (en)	1986-12-05
EP0096297A2 (fr)	1983-12-21
IL68817A0 (en)	1983-09-30
GR78269B (fr)	1984-09-26
PH21897A (en)	1988-04-07
DE3377061D1 (en)	1988-07-21
ES529774A0 (es)	1985-11-01
EP0096297B1 (fr)	1988-06-15
EP0096297A3 (en)	1984-04-11
FI832004A0 (fi)	1983-06-03
IE55402B1 (en)	1990-09-12
ES8601123A1 (es)	1985-11-01
AU1506883A (en)	1983-12-15
IL68817A (en)	1989-08-15
FI832004L (fi)	1983-12-04
DK241883A (da)	1983-12-04
DK241883D0 (da)	1983-05-27
PT76809A (en)	1983-07-01

Publication	Publication Date	Title
NO832001L (no)	1983-12-05	Fremgangsmaate ved fremstilling av 1-sulfo-2-okso-azetidinderivater
EP0053816B1 (fr)	1988-05-04	Dérivés de 1-sulfo-2-azétidinone, leur préparation et leur utilisation
US4794108A (en)	1988-12-27	1-carboxymethoxy acetidinones and their production
US4816582A (en)	1989-03-28	Antimicrobial 2-oxo-1-azetidinesulphonic acids
GB2139618A (en)	1984-11-14	beta -Lactam antibiotics
CA1246572A (fr)	1988-12-13	2-oxo-1-[[(sulfonyl substitue)amino]- carbonyl]azetidines
US4652651A (en)	1987-03-24	Process for the manufacture of 1-sulpho-2-oxoazetidine carboxylic acid intermediates via catalytic ester cleavage
US4587047A (en)	1986-05-06	2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines
IE55839B1 (en)	1991-01-30	Azetidine compounds
EP0093376B2 (fr)	1999-04-07	Dérivés de l'acide 2-azétidinone-1-sulfonique, leur préparation et leur utilisation
NZ199168A (en)	1985-08-30	2-oxoazetidine derivatives and pharmaceutical compositions
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