IL109321A - Cephalosporin derivatives their manufacture and pharmaceutical compositions containing them - Google Patents

Cephalosporin derivatives their manufacture and pharmaceutical compositions containing them

Info

Publication number: IL109321A
Authority: IL; Israel
Prior art keywords: oxo; ene; oct; compounds; carboxylic acid
Prior art date: 1993-04-16

Application number

IL10932194A

Other languages

English (en)

Other versions

IL109321A0 (en

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.)

1993-04-16

Filing date

1994-04-15

Publication date

1998-07-15

1994-03-21 Priority claimed from US08/213,562 external-priority patent/US5523400A/en

1994-04-15 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1994-07-31 Publication of IL109321A0 publication Critical patent/IL109321A0/xx

1998-07-15 Publication of IL109321A publication Critical patent/IL109321A/en

Links

229930186147 Cephalosporin Natural products 0.000 title claims abstract description 8
229940124587 cephalosporin Drugs 0.000 title claims abstract description 8
150000001780 cephalosporins Chemical class 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title claims description 20
239000008194 pharmaceutical composition Substances 0.000 title description 4
-1 carboxy, amino Chemical group 0.000 claims abstract description 350
150000001875 compounds Chemical class 0.000 claims abstract description 196
150000003839 salts Chemical class 0.000 claims abstract description 91
150000002148 esters Chemical class 0.000 claims abstract description 77
125000000217 alkyl group Chemical group 0.000 claims abstract description 56
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
239000001257 hydrogen Substances 0.000 claims abstract description 46
150000004677 hydrates Chemical class 0.000 claims abstract description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 26
150000002431 hydrogen Chemical class 0.000 claims abstract description 25
125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 23
125000003118 aryl group Chemical group 0.000 claims abstract description 20
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
125000002252 acyl group Chemical group 0.000 claims abstract description 19
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
150000002367 halogens Chemical class 0.000 claims abstract description 16
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 7
125000006244 carboxylic acid protecting group Chemical group 0.000 claims abstract description 6
SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 claims description 100
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 73
238000000034 method Methods 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 48
125000006239 protecting group Chemical group 0.000 claims description 26
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 13
230000008569 process Effects 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
GBEPMLYZCPHOBB-UHFFFAOYSA-N 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCSC2CCN12 GBEPMLYZCPHOBB-UHFFFAOYSA-N 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
208000035473 Communicable disease Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 164
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 125
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
239000000203 mixture Substances 0.000 description 74
238000005481 NMR spectroscopy Methods 0.000 description 68
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
229940093499 ethyl acetate Drugs 0.000 description 54
235000019439 ethyl acetate Nutrition 0.000 description 54
235000002639 sodium chloride Nutrition 0.000 description 51
239000000243 solution Substances 0.000 description 49
238000006243 chemical reaction Methods 0.000 description 44
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
239000002904 solvent Substances 0.000 description 42
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 41
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000007787 solid Substances 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
239000000047 product Substances 0.000 description 18
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
238000004452 microanalysis Methods 0.000 description 16
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 16
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 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
239000012267 brine Substances 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 12
235000019341 magnesium sulphate Nutrition 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
229960001407 sodium bicarbonate Drugs 0.000 description 12
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
125000001841 imino group Chemical group [H]N=* 0.000 description 11
239000011734 sodium Substances 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
125000001246 bromo group Chemical group Br* 0.000 description 10
229960004132 diethyl ether Drugs 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
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 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
125000004494 ethyl ester group Chemical group 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
150000007529 inorganic bases Chemical class 0.000 description 8
239000000463 material Substances 0.000 description 8
150000007530 organic bases Chemical class 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
239000011343 solid material Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
125000004185 ester group Chemical group 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
239000012071 phase Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
238000007239 Wittig reaction Methods 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000012442 inert solvent Substances 0.000 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 description 6
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
239000000725 suspension Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
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 6
WGGBNFPFDAICPR-UHFFFAOYSA-N 3-methylideneazetidin-2-one Chemical class C=C1CNC1=O WGGBNFPFDAICPR-UHFFFAOYSA-N 0.000 description 5
101150046236 CNR1 gene Proteins 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
125000002837 carbocyclic group Chemical group 0.000 description 5
239000012876 carrier material Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 5
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
OBRJBKJCXLWCTB-UHFFFAOYSA-N 4-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(=O)SC2CCN12 OBRJBKJCXLWCTB-UHFFFAOYSA-N 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
239000001828 Gelatine Substances 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
238000005903 acid hydrolysis reaction Methods 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
125000004442 acylamino group Chemical group 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
239000002274 desiccant Substances 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
125000001183 hydrocarbyl group Chemical group 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
125000001979 organolithium group Chemical group 0.000 description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
235000019345 sodium thiosulphate Nutrition 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
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001718 carbodiimides Chemical class 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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229940075931 sodium dithionate Drugs 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
CUXKZYSCZCNPNX-UHFFFAOYSA-N tetradecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCC[NH3+] CUXKZYSCZCNPNX-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
238000010555 transalkylation reaction Methods 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
JJPVWQWOOQYHCB-UHFFFAOYSA-N triethyl(phenyl)azanium Chemical compound CC[N+](CC)(CC)C1=CC=CC=C1 JJPVWQWOOQYHCB-UHFFFAOYSA-N 0.000 description 1
CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
125000005023 xylyl group Chemical group 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
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL10932194A 1993-04-16 1994-04-15 Cephalosporin derivatives their manufacture and pharmaceutical compositions containing them IL109321A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4868893A	1993-04-16	1993-04-16
US08/213,562 US5523400A (en)	1993-04-16	1994-03-21	Cephalosporin antibiotics

Publications (2)

Publication Number	Publication Date
IL109321A0 IL109321A0 (en)	1994-07-31
IL109321A true IL109321A (en)	1998-07-15

Family

ID=26726411

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10932194A IL109321A (en)	1993-04-16	1994-04-15	Cephalosporin derivatives their manufacture and pharmaceutical compositions containing them

Country Status (32)

Country	Link
EP (1)	EP0620225B1 (fr)
JP (1)	JP2845752B2 (fr)
CN (1)	CN1046524C (fr)
AT (1)	ATE227728T1 (fr)
AU (1)	AU675695B2 (fr)
BG (1)	BG61450B1 (fr)
BR (1)	BR9401503A (fr)
CA (1)	CA2121324C (fr)
CY (1)	CY2189B1 (fr)
CZ (1)	CZ91394A3 (fr)
DE (1)	DE69431691T2 (fr)
DK (1)	DK0620225T3 (fr)
ES (1)	ES2185634T3 (fr)
FI (1)	FI115525B (fr)
GB (1)	GB2277737B (fr)
GE (1)	GEP20002332B (fr)
HR (1)	HRP940252A2 (fr)
HU (2)	HUT71252A (fr)
IL (1)	IL109321A (fr)
IS (1)	IS4151A (fr)
LT (1)	LT3289B (fr)
LV (1)	LV10778B (fr)
NO (1)	NO305601B1 (fr)
NZ (1)	NZ260308A (fr)
OA (1)	OA10064A (fr)
PT (1)	PT620225E (fr)
RU (1)	RU2130939C1 (fr)
SG (1)	SG49814A1 (fr)
SK (1)	SK42694A3 (fr)
TW (1)	TW412537B (fr)
ZA (1)	ZA942612B (fr)
ZW (1)	ZW4794A1 (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5523400A (en) *	1993-04-16	1996-06-04	Hoffmann-La Roche Inc.	Cephalosporin antibiotics
US5856474A (en)	1994-04-25	1999-01-05	Biochemie Gesellschaft, M.B.H.	Cephalosporin synthesis
JPH11501017A (ja) *	1995-02-27	1999-01-26	エフ・ホフマン−ラロシュアーゲー	３−ピロリジリデン−２−オン−セファロスポリンの誘導体
US5804577A (en) *	1995-09-12	1998-09-08	Hoffmann-La Roche Inc.	Cephalosporin derivatives
EP0761673A1 (fr) *	1995-09-12	1997-03-12	F. Hoffmann-La Roche Ag	Dérivés de céphalosporine
US5811419A (en) *	1996-01-16	1998-09-22	Hoffmann-La Roche Inc.	Isooxacephem-derivatives
US5883247A (en) *	1996-06-10	1999-03-16	Hoffmann-La Roche Inc.	Preparation of cephem and isooxacephem derivatives
SG53049A1 (en) *	1996-09-23	1998-09-28	Hoffmann La Roche	1-carba-(dethia)-cephalosporin derivatives
EP0831093A1 (fr) *	1996-09-23	1998-03-25	F. Hoffmann-La Roche Ag	Dérivés de 1-carba-(déthia)-céphalosporine
TW446707B (en) *	1996-10-22	2001-07-21	Hoffmann La Roche	Cephalosporin pyridinium derivatives
EP0838465A1 (fr) *	1996-10-22	1998-04-29	F. Hoffmann-La Roche Ag	Dérivés de (lactamylvinyl)cephalosporin pyridinium substitués, leur préparation et leur utilisation comme antibiotiques
EP0841339B1 (fr) *	1996-11-06	2007-02-21	Basilea Pharmaceutica AG	Dérivés de vinylpyrrolidone-céphalosporine
TW415949B (en) *	1996-12-19	2000-12-21	Hoffmann La Roche	Vinyl pyrrolidine cephalosporin derivatives with basic substituents
US6114541A (en) *	1997-03-10	2000-09-05	Hoffmann-La Roche Inc.	Method for the preparation of α-Bromo-Lactam derivatives
US6150350A (en) *	1997-09-15	2000-11-21	Hoffman-La Roche Inc.	Antimicrobial compositions
ATE370146T1 (de)	1999-07-05	2007-09-15	Basilea Pharmaceutica Ag	Verfahren zur herstellung von cephalosporin- derivaten
KR100342944B1 (ko)	1999-11-08	2002-07-02	민경윤	고순도 세프포독심 프록세틸의 제조방법
ES2272372T3 (es)	2000-04-19	2007-05-01	Basilea Pharmaceutica Ag	Procedimiento para la preparacion de derivados de asparagina.
US6504025B2 (en) *	2000-05-24	2003-01-07	Basilea Pharmaceutica Ag	Process for the preparation of vinyl-pyrrolidinone cephalosporin derivatives
EP1723160A4 (fr) *	2004-03-04	2008-04-23	Univ British Columbia	Prevision de l'evolution de l'etat de patients au moyen des haplotypes du recepteur 2 de type toll (tlr-2)
AU2006316005A1 (en) *	2005-11-18	2007-05-24	Eisai R & D Management Co., Ltd.	Process for production of cinnamamide derivative
CN101245077B (zh) *	2007-02-14	2010-06-02	山东轩竹医药科技有限公司	头孢菌素衍生物
JP5403205B2 (ja) *	2007-10-29	2014-01-29	日産化学工業株式会社	２−アミノ−ｎ−（２，２，２−トリフルオロエチル）アセトアミド化合物又はその塩の製造方法
UY35103A (es)	2012-10-29	2014-05-30	Glaxo Group Ltd	Compuestos de cefem 2-sustituidos

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3971778A (en) *	1972-05-12	1976-07-27	Glaxo Laboratories Limited	Cephalosporins having (α-etherified oximino)acylamido groups at the 7-position
JPS5854157B2 (ja)	1977-06-10	1983-12-02	山之内製薬株式会社	セフアロスポリン化合物の新規誘導体ならびにその製造方法
US4255423A (en) *	1977-07-27	1981-03-10	Merck & Co., Inc.	Cephalosporin compounds
JPH0686463B2 (ja) *	1988-07-01	1994-11-02	明治製菓株式会社	新規セフェム化合物、その製造法及び抗菌剤
GB8821797D0 (en) *	1988-09-16	1988-10-19	Beecham Group Plc	Novel compounds

1994
- 1994-03-30 ES ES94104997T patent/ES2185634T3/es not_active Expired - Lifetime
- 1994-03-30 AT AT94104997T patent/ATE227728T1/de active
- 1994-03-30 DK DK94104997T patent/DK0620225T3/da active
- 1994-03-30 EP EP94104997A patent/EP0620225B1/fr not_active Expired - Lifetime
- 1994-03-30 PT PT94104997T patent/PT620225E/pt unknown
- 1994-03-30 DE DE69431691T patent/DE69431691T2/de not_active Expired - Lifetime
- 1994-04-14 GB GB9407400A patent/GB2277737B/en not_active Expired - Lifetime
- 1994-04-14 CA CA002121324A patent/CA2121324C/fr not_active Expired - Lifetime
- 1994-04-14 NZ NZ260308A patent/NZ260308A/xx unknown
- 1994-04-14 NO NO941342A patent/NO305601B1/no not_active IP Right Cessation
- 1994-04-14 SK SK426-94A patent/SK42694A3/sk unknown
- 1994-04-14 RU RU94012924A patent/RU2130939C1/ru active
- 1994-04-15 JP JP6101558A patent/JP2845752B2/ja not_active Expired - Lifetime
- 1994-04-15 FI FI941775A patent/FI115525B/fi not_active IP Right Cessation
- 1994-04-15 ZW ZW4794A patent/ZW4794A1/xx unknown
- 1994-04-15 LV LVP-94-73A patent/LV10778B/en unknown
- 1994-04-15 HR HR08/048,688A patent/HRP940252A2/hr not_active Application Discontinuation
- 1994-04-15 BR BR9401503A patent/BR9401503A/pt not_active Application Discontinuation
- 1994-04-15 TW TW083103375A patent/TW412537B/zh not_active IP Right Cessation
- 1994-04-15 GE GEAP19941859A patent/GEP20002332B/en unknown
- 1994-04-15 CN CN94104429A patent/CN1046524C/zh not_active Expired - Lifetime
- 1994-04-15 IL IL10932194A patent/IL109321A/en not_active IP Right Cessation
- 1994-04-15 IS IS4151A patent/IS4151A/is unknown
- 1994-04-15 CZ CZ94913A patent/CZ91394A3/cs unknown
- 1994-04-15 OA OA60495A patent/OA10064A/fr unknown
- 1994-04-15 BG BG98723A patent/BG61450B1/bg unknown
- 1994-04-15 HU HU9401080A patent/HUT71252A/hu unknown
- 1994-04-15 LT LTIP1916A patent/LT3289B/lt not_active IP Right Cessation
- 1994-04-15 AU AU59494/94A patent/AU675695B2/en not_active Expired
- 1994-04-15 ZA ZA942612A patent/ZA942612B/xx unknown
1995
- 1995-06-20 HU HU95P/P00262P patent/HU211652A9/hu unknown
1996
- 1996-03-28 SG SG1996006705A patent/SG49814A1/en unknown
1999
- 1999-07-26 CY CY9900020A patent/CY2189B1/xx unknown

Also Published As

Publication number	Publication date
NO305601B1 (no)	1999-06-28
ES2185634T3 (es)	2003-05-01
HRP940252A2 (en)	1996-08-31
HU211652A9 (en)	1995-12-28
CA2121324C (fr)	2007-07-10
LT3289B (en)	1995-06-26
GB9407400D0 (en)	1994-06-08
CA2121324A1 (fr)	1994-10-17
DE69431691T2 (de)	2003-08-21
EP0620225A1 (fr)	1994-10-19
SG49814A1 (en)	1998-06-15
ZA942612B (en)	1994-10-17
JPH06321954A (ja)	1994-11-22
NO941342D0 (no)	1994-04-14
HK1000423A1 (en)	1998-03-20
HU9401080D0 (en)	1994-07-28
ZW4794A1 (en)	1995-01-05
BG98723A (en)	1995-03-31
LTIP1916A (en)	1994-11-25
DE69431691D1 (de)	2002-12-19
NZ260308A (en)	1996-05-28
HUT71252A (en)	1995-11-28
AU5949494A (en)	1994-10-20
RU2130939C1 (ru)	1999-05-27
GB2277737B (en)	1996-09-25
EP0620225B1 (fr)	2002-11-13
BG61450B1 (bg)	1997-08-29
FI941775A0 (fi)	1994-04-15
IL109321A0 (en)	1994-07-31
CZ91394A3 (en)	1994-11-16
CY2189B1 (en)	2002-11-08
LV10778B (en)	1996-06-20
ATE227728T1 (de)	2002-11-15
GEP20002332B (en)	2000-12-25
GB2277737A (en)	1994-11-09
SK42694A3 (en)	1995-02-08
CN1046524C (zh)	1999-11-17
AU675695B2 (en)	1997-02-13
NO941342L (no)	1994-10-17
FI115525B (fi)	2005-05-31
JP2845752B2 (ja)	1999-01-13
BR9401503A (pt)	1994-10-25
DK0620225T3 (da)	2003-03-17
PT620225E (pt)	2003-03-31
LV10778A (lv)	1995-08-20
OA10064A (fr)	1996-10-14
TW412537B (en)	2000-11-21
FI941775L (fi)	1994-10-17
IS4151A (is)	1994-10-17
CN1105365A (zh)	1995-07-19

Legal Events

Date	Code	Title
1998-12-06	FF	Patent granted
2000-08-31	KB	Patent renewed
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
IL109321A (en)	1998-07-15	Cephalosporin derivatives their manufacture and pharmaceutical compositions containing them
KR100309516B1 (ko)	2006-05-25	세팔로스포린유도체
US5981519A (en)	1999-11-09	Vinyl-pyrrolidinone cephalosporins
HU183236B (en)	1984-04-28	Process for producing new 6-beta-hydroxyalkyl-penicillanic acid derivatives
EP0199446B1 (fr)	1990-06-13	Dérivés de pénème, leur préparation et application
AU624810B2 (en)	1992-06-25	Acyl derivatives
US6218379B1 (en)	2001-04-17	Tricyclic carbacephems
US5925632A (en)	1999-07-20	Derivatives of 3-pyrrolidylidene-2-one-cephalsporines
US5919939A (en)	1999-07-06	Preparation of cephem and isooxacephem derivatives
US5811419A (en)	1998-09-22	Isooxacephem-derivatives
US5362724A (en)	1994-11-08	Thioalkylthio carbacephalosporin derivatives
JP2002518505A (ja)	2002-06-25	プロペニルセファロスポリン誘導体
US4801704A (en)	1989-01-31	Methylene penam and derivatives thereof
CZ292097A3 (cs)	1998-04-15	1-Karba-(dethia)-Cefalosporinové deriváty
HU209817B (en)	1994-11-28	Process for the production of antibacterial 2-carbapenem derivatives
JPS61165366A (ja)	1986-07-26	ラクタム化合物の製造方法
JPH0475238B2 (fr)	1992-11-30
WO2001004127A1 (fr)	2001-01-18	Derives de vinylpyrrolidinone a cycle thiazole substitue
CS216936B2 (cs)	1982-12-31	Způsob výroby derivátů 7/3-aminothiazolylacetainido- -3-cefem-4-karboxylové kyseliny
MXPA00012689A (en)	2001-07-31	Propenyl cephalosporin derivatives