CA1292985C - Penames tricycliques; preparation et utilisation - Google Patents

Penames tricycliques; preparation et utilisation

Info

Publication number: CA1292985C
Authority: CA; Canada
Prior art keywords: compound; dioxo; alkyl; group; reaction
Prior art date: 1987-06-16
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CA000539827A

Other languages

English (en)

Inventor

Nobuo Choh

Noriyoshi Noguchi

Akira Morimoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-06-16

Filing date

1987-06-16

Publication date

1991-12-10

1987-06-16 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1987-06-16 Priority to CA000539827A priority Critical patent/CA1292985C/fr

1991-12-10 Application granted granted Critical

1991-12-10 Publication of CA1292985C publication Critical patent/CA1292985C/fr

2008-12-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 83
150000002959 penams Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 542
150000002148 esters Chemical class 0.000 claims abstract description 71
150000003839 salts Chemical class 0.000 claims abstract description 62
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
239000003242 anti bacterial agent Substances 0.000 claims abstract 3
-1 (8R,9S)-4,10-dioxo-9-[(1R)-1-hydroxy-ethyl]-3-oxa-7-thia-1-azatricyclo[6,2,0,02,6]decane-2-carboxylic acid Chemical compound 0.000 claims description 352
238000000034 method Methods 0.000 claims description 98
125000000217 alkyl group Chemical group 0.000 claims description 81
239000001257 hydrogen Substances 0.000 claims description 64
229910052739 hydrogen Inorganic materials 0.000 claims description 64
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
229910052736 halogen Inorganic materials 0.000 claims description 44
150000002367 halogens Chemical group 0.000 claims description 44
150000002431 hydrogen Chemical class 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
125000002252 acyl group Chemical group 0.000 claims description 33
239000003795 chemical substances by application Substances 0.000 claims description 33
125000003277 amino group Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000004442 acylamino group Chemical group 0.000 claims description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
230000000844 anti-bacterial effect Effects 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
125000004185 ester group Chemical group 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000002841 Lewis acid Substances 0.000 claims description 4
239000012190 activator Substances 0.000 claims description 4
210000004899 c-terminal region Anatomy 0.000 claims description 4
230000003301 hydrolyzing effect Effects 0.000 claims description 4
150000007517 lewis acids Chemical class 0.000 claims description 4
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
CSMOKSSLTYRTPF-UHFFFAOYSA-N 3,9-dioxo-10-oxa-6-thia-2-azatricyclo[5.3.0.02,5]decane-1-carboxylic acid Chemical compound OC(=O)C12OC(=O)CC1SC1N2C(=O)C1 CSMOKSSLTYRTPF-UHFFFAOYSA-N 0.000 claims 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
125000001246 bromo group Chemical group Br* 0.000 claims 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
VVKRBUUXVTUCRG-HVOGRVBKSA-N (1R,4R,5R,7S)-3,9-dioxo-4-[(2-phenylacetyl)amino]-10-oxa-6-thia-2-azatricyclo[5.3.0.02,5]decane-1-carboxylic acid Chemical compound N([C@H]1[C@H]2S[C@H]3CC(=O)O[C@]3(N2C1=O)C(=O)O)C(=O)CC1=CC=CC=C1 VVKRBUUXVTUCRG-HVOGRVBKSA-N 0.000 claims 1
JQMYZFDVJOUZEA-NLDHIRIYSA-N (1R,4R,5R,7S)-4-[[(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-3,9-dioxo-10-oxa-6-thia-2-azatricyclo[5.3.0.02,5]decane-1-carboxylic acid Chemical compound N([C@@H]1C(N2[C@@]3(OC(=O)C[C@@H]3S[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(NC(=O)CCl)=N1 JQMYZFDVJOUZEA-NLDHIRIYSA-N 0.000 claims 1
BGABIAQJTAPXRW-VYUPESLNSA-N (1S,4R,5R,7R)-3,9-dioxo-4-[(2-phenoxyacetyl)amino]-10-oxa-6-thia-2-azatricyclo[5.3.0.02,5]decane-1-carboxylic acid Chemical compound N([C@H]1[C@H]2S[C@@H]3CC(=O)O[C@@]3(N2C1=O)C(=O)O)C(=O)COC1=CC=CC=C1 BGABIAQJTAPXRW-VYUPESLNSA-N 0.000 claims 1
VVKRBUUXVTUCRG-VYUPESLNSA-N (1S,4R,5R,7R)-3,9-dioxo-4-[(2-phenylacetyl)amino]-10-oxa-6-thia-2-azatricyclo[5.3.0.02,5]decane-1-carboxylic acid Chemical compound N([C@H]1[C@H]2S[C@@H]3CC(=O)O[C@@]3(N2C1=O)C(=O)O)C(=O)CC1=CC=CC=C1 VVKRBUUXVTUCRG-VYUPESLNSA-N 0.000 claims 1
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 79
229910052757 nitrogen Inorganic materials 0.000 abstract description 38
229910052799 carbon Inorganic materials 0.000 abstract description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 294
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 267
239000000243 solution Substances 0.000 description 192
238000006243 chemical reaction Methods 0.000 description 180
239000002904 solvent Substances 0.000 description 158
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 148
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 111
235000019439 ethyl acetate Nutrition 0.000 description 98
229940093499 ethyl acetate Drugs 0.000 description 98
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 92
239000011541 reaction mixture Substances 0.000 description 90
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 89
125000001424 substituent group Chemical group 0.000 description 86
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 81
239000000047 product Substances 0.000 description 76
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 73
238000005481 NMR spectroscopy Methods 0.000 description 71
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 70
239000000203 mixture Substances 0.000 description 70
238000001816 cooling Methods 0.000 description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
239000000741 silica gel Substances 0.000 description 59
229910002027 silica gel Inorganic materials 0.000 description 59
125000003118 aryl group Chemical group 0.000 description 57
239000002585 base Substances 0.000 description 54
239000002253 acid Substances 0.000 description 51
125000000623 heterocyclic group Chemical group 0.000 description 51
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
239000000126 substance Substances 0.000 description 50
229910052943 magnesium sulfate Inorganic materials 0.000 description 49
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 47
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
239000013078 crystal Substances 0.000 description 45
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 43
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
239000012044 organic layer Substances 0.000 description 41
239000000843 powder Substances 0.000 description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
125000003545 alkoxy group Chemical group 0.000 description 36
235000019341 magnesium sulphate Nutrition 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000000725 suspension Substances 0.000 description 33
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
238000003756 stirring Methods 0.000 description 32
235000019441 ethanol Nutrition 0.000 description 31
229960000443 hydrochloric acid Drugs 0.000 description 30
229940086542 triethylamine Drugs 0.000 description 30
239000007858 starting material Substances 0.000 description 29
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
229910001873 dinitrogen Inorganic materials 0.000 description 28
235000011167 hydrochloric acid Nutrition 0.000 description 28
125000004432 carbon atom Chemical group C* 0.000 description 27
125000000753 cycloalkyl group Chemical group 0.000 description 27
239000010410 layer Substances 0.000 description 26
230000035484 reaction time Effects 0.000 description 26
239000011734 sodium Substances 0.000 description 25
125000003342 alkenyl group Chemical group 0.000 description 24
229910052708 sodium Inorganic materials 0.000 description 24
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 23
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 21
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 20
239000007864 aqueous solution Substances 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
239000012267 brine Substances 0.000 description 19
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
SAOSCTYRONNFTC-UHFFFAOYSA-N 2-methyl-decanoic acid Chemical group CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 17
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
238000004440 column chromatography Methods 0.000 description 16
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 16
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
239000011259 mixed solution Substances 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
150000008065 acid anhydrides Chemical class 0.000 description 15
239000012043 crude product Substances 0.000 description 15
125000004093 cyano group Chemical group *C#N 0.000 description 15
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 14
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 14
230000001376 precipitating effect Effects 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
235000011054 acetic acid Nutrition 0.000 description 13
150000007513 acids Chemical class 0.000 description 13
239000003054 catalyst Substances 0.000 description 13
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
238000006722 reduction reaction Methods 0.000 description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 12
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 12
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
239000007832 Na2SO4 Substances 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
229910052783 alkali metal Inorganic materials 0.000 description 12
239000012046 mixed solvent Substances 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
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 12
101150041968 CDC13 gene Proteins 0.000 description 11
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 11
125000003282 alkyl amino group Chemical group 0.000 description 11
238000005886 esterification reaction Methods 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
125000004433 nitrogen atom Chemical group N* 0.000 description 11
QQRIOTHLERJVGI-UHFFFAOYSA-N 3-bromo-5-[(4-nitrophenyl)methoxy]-4,5-dioxopentanoic acid Chemical compound OC(=O)CC(Br)C(=O)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QQRIOTHLERJVGI-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 10
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 10
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
229920001429 chelating resin Polymers 0.000 description 10
238000000921 elemental analysis Methods 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
239000008055 phosphate buffer solution Substances 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
239000011591 potassium Substances 0.000 description 10
229910052700 potassium Inorganic materials 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 9
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
229930182555 Penicillin Natural products 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000004104 aryloxy group Chemical group 0.000 description 9
238000010511 deprotection reaction Methods 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
230000032050 esterification Effects 0.000 description 9
239000000284 extract Substances 0.000 description 9
238000000434 field desorption mass spectrometry Methods 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000011777 magnesium Substances 0.000 description 9
229940049954 penicillin Drugs 0.000 description 9
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 8
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
241001024304 Mino Species 0.000 description 8
125000004423 acyloxy group Chemical group 0.000 description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
238000001035 drying Methods 0.000 description 8
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HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
CHVZPRDGLWBEMJ-UHFFFAOYSA-N n-chlorobenzenesulfonamide Chemical compound ClNS(=O)(=O)C1=CC=CC=C1 CHVZPRDGLWBEMJ-UHFFFAOYSA-N 0.000 description 1
DISPOJHKKXSCLS-UHFFFAOYSA-N n-diaminophosphorylmethanamine Chemical compound CNP(N)(N)=O DISPOJHKKXSCLS-UHFFFAOYSA-N 0.000 description 1
KUUCNJRLGRMLLA-UHFFFAOYSA-N n-ethylethanamine;n-propylpropan-1-amine Chemical compound CCNCC.CCCNCCC KUUCNJRLGRMLLA-UHFFFAOYSA-N 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
XUZLXCQFXTZASF-UHFFFAOYSA-N nitro(phenyl)methanol Chemical compound [O-][N+](=O)C(O)C1=CC=CC=C1 XUZLXCQFXTZASF-UHFFFAOYSA-N 0.000 description 1
FYWSTUCDSVYLPV-UHFFFAOYSA-N nitrooxythallium Chemical compound [Tl+].[O-][N+]([O-])=O FYWSTUCDSVYLPV-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008183 oral pharmaceutical preparation Substances 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
238000012856 packing Methods 0.000 description 1
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam group Chemical group S1CCN2[C@H]1CC2=O WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
125000000405 phenylalanyl group Chemical group 0.000 description 1
229940117953 phenylisothiocyanate Drugs 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 description 1
JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 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
238000001004 secondary ion mass spectrometry Methods 0.000 description 1
125000002072 seryl group Chemical group 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 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
239000007974 sodium acetate buffer Substances 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
MOTOGHHLNTXPTI-UHFFFAOYSA-M sodium;5-hydroxy-2,5-dioxopentanoate Chemical compound [Na+].OC(=O)CCC(=O)C([O-])=O MOTOGHHLNTXPTI-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
229960002920 sorbitol Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
YLXNLHFGLNCGEK-UHFFFAOYSA-N tert-butyl 5-oxooxolane-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCC(=O)O1 YLXNLHFGLNCGEK-UHFFFAOYSA-N 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
125000001239 threonyl group Chemical group 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
239000005051 trimethylchlorosilane Substances 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
JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
NRAPCRKPJHRWMI-UHFFFAOYSA-N tritylboron Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([B])C1=CC=CC=C1 NRAPCRKPJHRWMI-UHFFFAOYSA-N 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
239000012000 urushibara nickel Substances 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002114 valyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000539827A 1987-06-16 1987-06-16 Penames tricycliques; preparation et utilisation Expired - Lifetime CA1292985C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000539827A CA1292985C (fr)	1987-06-16	1987-06-16	Penames tricycliques; preparation et utilisation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000539827A CA1292985C (fr)	1987-06-16	1987-06-16	Penames tricycliques; preparation et utilisation

Publications (1)

Publication Number	Publication Date
CA1292985C true CA1292985C (fr)	1991-12-10

Family

ID=4135915

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000539827A Expired - Lifetime CA1292985C (fr)	1987-06-16	1987-06-16	Penames tricycliques; preparation et utilisation

Country Status (1)

Country	Link
CA (1)	CA1292985C (fr)

1987
- 1987-06-16 CA CA000539827A patent/CA1292985C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1999-12-10	MKLA	Lapsed

Publication	Publication Date	Title
FI80271B (fi)	1990-01-31	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 1-sulfo-2-azetidinoniderivat, och nya som mellanprodukt anvaendbara 2-azetidinonderivat.
US4794108A (en)	1988-12-27	1-carboxymethoxy acetidinones and their production
NL8105470A (nl)	1982-07-01	1-sulfo 2-oxoazetidinederivaten, alsmede bereiding en toepassing daarvan.
GB2124207A (en)	1984-02-15	1-sulfo-2-oxoazetidine derivatives
JP2695132B2 (ja)	1997-12-24	新規な、単環式又は二環式ｄｎａジャイレース阻害剤
KR880001564B1 (ko)	1988-08-22	2-옥소아제티딘 유도체의 제법
AU2002215212B2 (en)	2004-10-14	1-methylcarbapenem derivatives
US4891427A (en)	1990-01-02	Tricyclic cepham compounds
US4876251A (en)	1989-10-24	Tricyclic penam compounds, their production and their use
US4897489A (en)	1990-01-30	Antibiotic derivatives, their production and use
CA1292985C (fr)	1991-12-10	Penames tricycliques; preparation et utilisation
JPS6383082A (ja)	1988-04-13	テトラヒドロフランカルボン酸誘導体の製造法
US4851422A (en)	1989-07-25	Antibiotic 2-(3-oxo-2-isoxazolidinyl)-5-oxo-2-tetrahydrofuran-carboxylates
HU192819B (en)	1987-07-28	Process for preparing antibacterial penemic derivatives
WO1986006380A1 (fr)	1986-11-06	Composes antibacteriens, utilisation et preparation
EP0191989A1 (fr)	1986-08-27	Dérivés de l'isoxazole à activité antibiotique, leur préparation et leur application
GB2233330A (en)	1991-01-09	Penams
EP0416810A2 (fr)	1991-03-13	Dérivés de céphalosporine, leur procédé de préparation, compositions pharmaceutiques et intermédiaires
JPH06500788A (ja)	1994-01-27	セファロスポリン誘導体およびそれらの同族体
KR930005174B1 (ko)	1993-06-16	항생물질 유도체의 제조방법
KR870000528B1 (ko)	1987-03-14	3-아지도 세팔로스포린의 제조방법
EP0187500B1 (fr)	1993-04-28	Monobactames
WO1987000527A1 (fr)	1987-01-29	Composes antibacteriens, leur utilisation et procede de preparation
KR930001405B1 (ko)	1993-02-27	2-(4-치환아미노-3-옥소-이속사졸리디닐)-5-옥소-2-테트라히드로푸란카르복실산 유도체의 제조방법
Singh et al.	1989	Desulfation and rearrangement of tigemonam to an isoxazolidin‐5‐one and the synthesis of the rearrangement product