IL90497A - אזטידינוניםכ חומרי ביניים להכנת 1-קרבה )דתיה( צפלוספורינים - Google Patents

אזטידינוניםכ חומרי ביניים להכנת 1-קרבה )דתיה( צפלוספורינים

Info

Publication number: IL90497A
Authority: IL; Israel
Prior art keywords: compound; formula; carba; azetidinone; dethia
Prior art date: 1988-06-06

Application number

IL9049789A

Other languages

English (en)

Other versions

IL90497A0 (en

Original Assignee

Lilly Co Eli

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.)

1988-06-06

Filing date

1989-06-01

Publication date

1994-02-27

1989-06-01 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1990-01-18 Publication of IL90497A0 publication Critical patent/IL90497A0/xx

1994-02-27 Publication of IL90497A publication Critical patent/IL90497A/he

Links

MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title description 30
229940124587 cephalosporin Drugs 0.000 title description 15
229930186147 Cephalosporin Natural products 0.000 title description 13
239000000543 intermediate Substances 0.000 title description 13
150000001780 cephalosporins Chemical class 0.000 title description 12
-1 p-methoxybenzyl Chemical group 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 29
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004185 ester group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
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 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
239000000047 product Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000002253 acid Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
239000002904 solvent Substances 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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
KQLYGALWBRSYQB-UHFFFAOYSA-N 4-oxoazetidine-2-carbaldehyde Chemical compound O=CC1CC(=O)N1 KQLYGALWBRSYQB-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
CLJBDOUIEHLLEN-UHFFFAOYSA-N 4-keto-n-caproic acid Chemical compound CCC(=O)CCC(O)=O CLJBDOUIEHLLEN-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
159000000003 magnesium salts Chemical class 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
VTKBVZBJLMNZKR-UHFFFAOYSA-J [Rh+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O Chemical compound [Rh+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O VTKBVZBJLMNZKR-UHFFFAOYSA-J 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
OTRQFHJPBPUOES-UHFFFAOYSA-N benzyl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OCC1=CC=CC=C1 OTRQFHJPBPUOES-UHFFFAOYSA-N 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 1
VURCBCQGFLMYRK-UHFFFAOYSA-N 3-(4-oxoazetidin-2-yl)propanoic acid Chemical class OC(=O)CCC1CC(=O)N1 VURCBCQGFLMYRK-UHFFFAOYSA-N 0.000 description 1
GCBWDZYSLVSRRI-UHFFFAOYSA-N 3-aminoazetidin-2-one Chemical compound NC1CNC1=O GCBWDZYSLVSRRI-UHFFFAOYSA-N 0.000 description 1
HAQOEZOMHMJWIQ-UHFFFAOYSA-N 4-(3-imidazol-1-yl-3-oxopropyl)azetidin-2-one Chemical class C1=CN=CN1C(=O)CCC1CC(=O)N1 HAQOEZOMHMJWIQ-UHFFFAOYSA-N 0.000 description 1
OWULJVXJAZBQLL-UHFFFAOYSA-N 4-azidosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 OWULJVXJAZBQLL-UHFFFAOYSA-N 0.000 description 1
IHVUPGWCHADOPR-UHFFFAOYSA-N 5-diazo-4-oxohexanoic acid Chemical compound C(=O)(O)CCC(C(C)=[N+]=[N-])=O IHVUPGWCHADOPR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
PJJISXIOSNSQCV-UHFFFAOYSA-N CCC(=O)CCC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 Chemical compound CCC(=O)CCC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 PJJISXIOSNSQCV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
239000005046 Chlorosilane Substances 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
229910018540 Si C Inorganic materials 0.000 description 1
241000534944 Thia Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
238000011929 asymmetric total synthesis Methods 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 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
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 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
- C07D205/085—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
- 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

IL9049789A 1988-06-06 1989-06-01 אזטידינוניםכ חומרי ביניים להכנת 1-קרבה )דתיה( צפלוספורינים IL90497A (he)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/202,287 US4885362A (en)	1988-06-06	1988-06-06	Azetidinone intermediates for 1-carba(dethia)caphalosporins

Publications (2)

Publication Number	Publication Date
IL90497A0 IL90497A0 (en)	1990-01-18
IL90497A true IL90497A (he)	1994-02-27

Family

ID=22749255

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9049789A IL90497A (he)	1988-06-06	1989-06-01	אזטידינוניםכ חומרי ביניים להכנת 1-קרבה )דתיה( צפלוספורינים

Country Status (7)

Country	Link
US (1)	US4885362A (he)
EP (1)	EP0345997A3 (he)
JP (1)	JPH0225491A (he)
KR (1)	KR910000634A (he)
CA (1)	CA1330565C (he)
HU (1)	HU205941B (he)
IL (1)	IL90497A (he)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5750681A (en) *	1995-06-19	1998-05-12	University Of Notre Dame Du Lac	Bicyclic beta-lactams and process therefor
SE0303307L (sv)	2003-12-10	2004-10-19	Swep Int Ab	Plattvärmeväxlare

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4226866A (en) *	1972-11-06	1980-10-07	Merck & Co., Inc.	Novel antibiotic analogues of cephalosporins
EP0034443B1 (en) *	1980-02-14	1984-09-26	Beecham Group Plc	Beta-lactam antibacterial compounds, their preparation and pharmaceutical compositions containing them
WO1982001873A1 (en) *	1980-12-05	1982-06-10	Takeda Chemical Industries Ltd	1-sulfo-2-oxoazetidine derivatives and process for their preparation
CA1249279A (en) *	1984-05-22	1989-01-24	Larry C. Blaszczak	Process for carbon-carbon bond formation at the c-4 position of 3-acylaminoazetidinones
US4665171A (en) *	1985-07-17	1987-05-12	Harvard University	Process and intermediates for β-lactam antibiotics

1988
- 1988-06-06 US US07/202,287 patent/US4885362A/en not_active Expired - Lifetime
1989
- 1989-06-01 EP EP19890305512 patent/EP0345997A3/en not_active Withdrawn
- 1989-06-01 KR KR1019890007507A patent/KR910000634A/ko not_active Withdrawn
- 1989-06-01 IL IL9049789A patent/IL90497A/he not_active IP Right Cessation
- 1989-06-01 JP JP1140239A patent/JPH0225491A/ja active Pending
- 1989-06-01 CA CA000601456A patent/CA1330565C/en not_active Expired - Fee Related
- 1989-06-02 HU HU892829A patent/HU205941B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL90497A0 (en)	1990-01-18
EP0345997A2 (en)	1989-12-13
KR910000634A (ko)	1991-01-29
EP0345997A3 (en)	1991-05-15
CA1330565C (en)	1994-07-05
HU205941B (en)	1992-07-28
US4885362A (en)	1989-12-05
JPH0225491A (ja)	1990-01-26
HUT50481A (en)	1990-02-28

Legal Events

Date	Code	Title	Description
1996-03-31	RH	Patent void

Publication	Publication Date	Title
EP0180252B1 (en)	1989-04-26	Process of preparing azetidinone compounds
EP0054917B1 (en)	1988-03-09	6- and 4-substituted-1-azabicyclo(3.2.0)heptan-3,7-dione-2-carboxylates
EP0023097B1 (en)	1984-08-01	De-arylmethylation of n-mono- or n-diarylmethyl-beta-lactams; novel azetizinones having anti-bacterial activity
CA1234099A (en)	1988-03-15	Process for the production of penems
US4443373A (en)	1984-04-17	Process for the production of antibiotic penems
EP0167155B1 (en)	1989-03-08	Beta-lactam compound and preparing thereof
US4639335A (en)	1987-01-27	Stereocontrolled acetoxyazetidinone process
US4885362A (en)	1989-12-05	Azetidinone intermediates for 1-carba(dethia)caphalosporins
US4610823A (en)	1986-09-09	Process for preparing substituted 2-thioxopenams and 2-substituted thiopenems
EP0414904B1 (en)	1995-03-29	Preparation of enol silyl ether compounds
CA1327045C (en)	1994-02-15	Azetidinone derivative and process for preparing the same
PL172378B1 (pl)	1997-09-30	Sposób wytwarzania nowych 4-podstawionych azetydynonów PL PL PL PL PL PL
US5106968A (en)	1992-04-21	Process for bicyclic β-lactams diazo-β-keto-butyrate-intermediates for bicyclic β-lactams
US4511509A (en)	1985-04-16	3-Alkylidine azetidine compound and their production
EP0308123B1 (en)	1993-12-08	Crystalline antibiotic intermediate
US4663451A (en)	1987-05-05	Process for the synthesis of penems and penams
US4939249A (en)	1990-07-03	Process for 1-carba(dethia) cephalosporins
JPH04368365A (ja)	1992-12-21	アゼチジノン誘導体の製法
EP0066301B1 (en)	1986-01-22	Intermediates for the preparation of thienamycin and process for preparing the same
JP2810731B2 (ja)	1998-10-15	β―ラクタム化合物の製法
JP3476852B2 (ja)	2003-12-10	アゼチジノン誘導体の製造法
US4760058A (en)	1988-07-26	Penam derivatives
JPH0256349B2 (he)	1990-11-29
JPH085853B2 (ja)	1996-01-24	ラクタム化合物およびその製法
JPH0321025B2 (he)	1991-03-20