CA1338539C - Derives de la 1-sulfo-2-oxoazetidine et leur preparation - Google Patents

Derives de la 1-sulfo-2-oxoazetidine et leur preparation

Info

Publication number: CA1338539C
Authority: CA; Canada
Prior art keywords: amino; thiazolyl; group; alkyl; oxoazetidine
Prior art date: 1980-12-04
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 - Fee Related

Application number

CA000391401A

Other languages

English (en)

Inventor

Taisuke Matsuo

Michihiko Ochiai

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.)

1980-12-04

Filing date

1981-12-03

Publication date

1996-08-20

1980-12-04 Priority claimed from PCT/JP1980/000295 external-priority patent/WO1982001820A1/fr

1980-12-05 Priority claimed from PCT/JP1980/000297 external-priority patent/WO1982001873A1/fr

1981-10-23 Priority claimed from EP81304996A external-priority patent/EP0050965A1/fr

1981-10-23 Priority claimed from JP56170634A external-priority patent/JPS5798258A/ja

1981-12-03 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1996-08-20 Application granted granted Critical

1996-08-20 Publication of CA1338539C publication Critical patent/CA1338539C/fr

2013-08-20 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

CDFGMYLBUSYTKQ-UHFFFAOYSA-N 2-oxoazetidine-1-sulfonic acid Chemical class OS(=O)(=O)N1CCC1=O CDFGMYLBUSYTKQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 107
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 54
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 51
150000003839 salts Chemical class 0.000 claims abstract description 46
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
239000001257 hydrogen Substances 0.000 claims abstract description 42
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
230000000845 anti-microbial effect Effects 0.000 claims abstract description 7
-1 nitro, amino, oxo, thioxo Chemical group 0.000 claims description 446
239000000203 mixture Substances 0.000 claims description 256
239000011734 sodium Substances 0.000 claims description 158
229910052708 sodium Inorganic materials 0.000 claims description 158
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 claims description 155
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 67
238000000034 method Methods 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 57
125000000623 heterocyclic group Chemical group 0.000 claims description 45
125000002252 acyl group Chemical group 0.000 claims description 44
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 43
229910052736 halogen Inorganic materials 0.000 claims description 42
150000002367 halogens Chemical group 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
125000006239 protecting group Chemical group 0.000 claims description 38
125000001424 substituent group Chemical group 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
229910052717 sulfur Inorganic materials 0.000 claims description 27
239000003795 chemical substances by application Substances 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 19
125000004423 acyloxy group Chemical group 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
208000015181 infectious disease Diseases 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000004442 acylamino group Chemical group 0.000 claims description 5
125000004450 alkenylene group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000000539 amino acid group Chemical group 0.000 claims description 5
239000003242 anti bacterial agent Substances 0.000 claims description 5
230000003115 biocidal effect Effects 0.000 claims description 5
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
241000894006 Bacteria Species 0.000 claims description 4
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
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 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
238000011282 treatment Methods 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
125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 3
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 3
125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 3
125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims description 3
229950003188 isovaleryl diethylamide Drugs 0.000 claims description 3
125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
125000000405 phenylalanyl group Chemical group 0.000 claims description 3
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 3
125000000349 (Z)-3-carboxyprop-2-enoyl group Chemical group O=C([*])/C([H])=C([H])\C(O[H])=O 0.000 claims description 2
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
125000006032 3-methyl-3-butenyl group Chemical group 0.000 claims description 2
PVEFUFWXAAQQFP-XMLTWROESA-M ClCC(=O)NC=1SC=C(N1)C(C(=O)N[C@@H]1C(N([C@H]1C)S(=O)(=O)[O-])=O)=NOC.[Na+] Chemical compound ClCC(=O)NC=1SC=C(N1)C(C(=O)N[C@@H]1C(N([C@H]1C)S(=O)(=O)[O-])=O)=NOC.[Na+] PVEFUFWXAAQQFP-XMLTWROESA-M 0.000 claims description 2
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 26
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 22
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
125000000204 (C2-C4) acyl group Chemical group 0.000 claims 2
125000001980 alanyl group Chemical group 0.000 claims 2
125000005724 cycloalkenylene group Chemical group 0.000 claims 2
125000001288 lysyl group Chemical group 0.000 claims 2
125000002072 seryl group Chemical group 0.000 claims 2
125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 2
125000002114 valyl group Chemical group 0.000 claims 2
125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 1
150000002148 esters Chemical class 0.000 abstract description 24
125000003277 amino group Chemical group 0.000 abstract description 21
229910052799 carbon Inorganic materials 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 7
241001465754 Metazoa Species 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 4
241000282414 Homo sapiens Species 0.000 abstract description 3
239000004599 antimicrobial Substances 0.000 abstract description 3
125000002393 azetidinyl group Chemical group 0.000 abstract description 3
229940079593 drug Drugs 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 292
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 287
229910001868 water Inorganic materials 0.000 description 226
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 218
239000000243 solution Substances 0.000 description 165
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 141
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 126
230000002829 reductive effect Effects 0.000 description 117
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 114
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 109
238000000921 elemental analysis Methods 0.000 description 109
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 107
238000001816 cooling Methods 0.000 description 104
229940093499 ethyl acetate Drugs 0.000 description 98
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 97
235000019439 ethyl acetate Nutrition 0.000 description 97
239000013078 crystal Substances 0.000 description 96
238000001914 filtration Methods 0.000 description 91
239000007864 aqueous solution Substances 0.000 description 90
239000002904 solvent Substances 0.000 description 90
238000003756 stirring Methods 0.000 description 87
239000011541 reaction mixture Substances 0.000 description 74
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 73
239000000047 product Substances 0.000 description 68
239000000706 filtrate Substances 0.000 description 65
239000010410 layer Substances 0.000 description 63
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 57
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 55
239000011780 sodium chloride Substances 0.000 description 54
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 53
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
229910000030 sodium bicarbonate Inorganic materials 0.000 description 51
238000004440 column chromatography Methods 0.000 description 48
235000017557 sodium bicarbonate Nutrition 0.000 description 48
235000019441 ethanol Nutrition 0.000 description 46
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
229920005989 resin Polymers 0.000 description 44
239000011347 resin Substances 0.000 description 44
229920001429 chelating resin Polymers 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
125000003118 aryl group Chemical group 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
229920001467 poly(styrenesulfonates) Polymers 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
239000003480 eluent Substances 0.000 description 31
229920006395 saturated elastomer Polymers 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
239000000843 powder Substances 0.000 description 26
125000003545 alkoxy group Chemical group 0.000 description 24
239000000725 suspension Substances 0.000 description 24
101150041968 CDC13 gene Proteins 0.000 description 23
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
239000003054 catalyst Substances 0.000 description 22
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 22
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
229960001866 silicon dioxide Drugs 0.000 description 22
239000002253 acid Substances 0.000 description 21
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
125000003710 aryl alkyl group Chemical group 0.000 description 18
239000000284 extract Substances 0.000 description 18
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 18
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 18
238000004587 chromatography analysis Methods 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
230000010933 acylation Effects 0.000 description 15
238000005917 acylation reaction Methods 0.000 description 15
239000002585 base Substances 0.000 description 14
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 14
238000000605 extraction Methods 0.000 description 14
239000000460 chlorine Substances 0.000 description 13
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 13
238000010992 reflux Methods 0.000 description 13
239000007787 solid Substances 0.000 description 13
229940086542 triethylamine Drugs 0.000 description 13
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 12
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 12
238000001035 drying Methods 0.000 description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
235000011054 acetic acid Nutrition 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
238000010531 catalytic reduction reaction Methods 0.000 description 11
235000008504 concentrate Nutrition 0.000 description 11
239000012141 concentrate Substances 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
235000011167 hydrochloric acid Nutrition 0.000 description 11
229960000443 hydrochloric acid Drugs 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 10
125000003342 alkenyl group Chemical group 0.000 description 10
239000012298 atmosphere Substances 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
239000007788 liquid Substances 0.000 description 10
KDGBDILWXRRBDF-HRFVKAFMSA-N methyl (2s,3s)-3-amino-4-oxoazetidine-2-carboxylate Chemical compound COC(=O)[C@H]1NC(=O)[C@H]1N KDGBDILWXRRBDF-HRFVKAFMSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 9
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229910052742 iron Inorganic materials 0.000 description 1
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125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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HRWBUBXJQMPIMU-GHXNOFRVSA-N methyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-propoxyiminoacetate Chemical compound CCCO\N=C(/C(=O)OC)C1=CSC(N)=N1 HRWBUBXJQMPIMU-GHXNOFRVSA-N 0.000 description 1
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LVNCRQYBZYZEPP-UCORVYFPSA-N methyl 2-[(2s,3s)-3-azido-4-oxoazetidin-2-yl]acetate Chemical compound COC(=O)C[C@@H]1NC(=O)[C@H]1N=[N+]=[N-] LVNCRQYBZYZEPP-UCORVYFPSA-N 0.000 description 1
UEANFLFICLOLKW-UHFFFAOYSA-N methyl 2-[3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-4-oxoazetidin-2-yl]acetate Chemical compound C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)NC1C(CC(=O)OC)NC1=O UEANFLFICLOLKW-UHFFFAOYSA-N 0.000 description 1
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125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
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FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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SDRZXZKXVBHREH-UHFFFAOYSA-M potassium;dihydrogen phosphate;phosphoric acid Chemical compound [K+].OP(O)(O)=O.OP(O)([O-])=O SDRZXZKXVBHREH-UHFFFAOYSA-M 0.000 description 1
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125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 description 1
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150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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238000007789 sealing Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
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IMIKTJFVUONBDK-MCJVGQIASA-M sodium (2R,3S)-3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-[2-methyl-1-[(4-nitrophenyl)methoxy]-1-oxopropan-2-yl]oxyiminoacetyl]amino]-2-methoxycarbonyl-4-oxoazetidine-1-sulfonate Chemical compound ClCC(=O)NC=1SC=C(N1)C(C(=O)N[C@@H]1C(N([C@H]1C(=O)OC)S(=O)(=O)[O-])=O)=NOC(C)(C(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])C.[Na+] IMIKTJFVUONBDK-MCJVGQIASA-M 0.000 description 1
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235000019345 sodium thiosulphate Nutrition 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
LTMJDMOBNQGDKG-UOERWJHTSA-M sodium;(2r,3s)-3-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-2-methoxycarbonyl-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(N)=NC=1C(=NOC)C(=O)N[C@H]1[C@H](C(=O)OC)N(S([O-])(=O)=O)C1=O LTMJDMOBNQGDKG-UOERWJHTSA-M 0.000 description 1
IILIQBOOOGBVKN-UHFFFAOYSA-M sodium;3-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-2-(2-methoxy-2-oxoethyl)-4-oxoazetidine-1-sulfonate Chemical compound [Na+].C=1SC(NC(=O)CCl)=NC=1C(=NOC)C(=O)NC1C(CC(=O)OC)N(S([O-])(=O)=O)C1=O IILIQBOOOGBVKN-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229960004932 sulbenicillin Drugs 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
230000001502 supplementing effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000011975 tartaric acid Substances 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
RWXVMOBDVOAUHW-UHFFFAOYSA-N tert-butyl-chloro-diethylsilane Chemical compound CC[Si](Cl)(CC)C(C)(C)C RWXVMOBDVOAUHW-UHFFFAOYSA-N 0.000 description 1
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 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
150000003512 tertiary amines Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000004385 trihaloalkyl group Chemical group 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
239000006150 trypticase soy agar Substances 0.000 description 1
125000005454 tryptophanyl group Chemical group 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 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
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000391401A 1980-12-04 1981-12-03 Derives de la 1-sulfo-2-oxoazetidine et leur preparation Expired - Fee Related CA1338539C (fr)

Applications Claiming Priority (14)

Application Number	Priority Date	Filing Date	Title
PCT/JP1980/000295 WO1982001820A1 (fr)	1980-12-04	1980-12-04	Composition d'inhibition de la (beta) lactamase
JPPCT/JP80/00295		1980-12-04
PCT/JP1980/000297 WO1982001873A1 (fr)	1980-12-05	1980-12-05	Derives 1-sulfo-2-oxoazetidine et leur procede de preparation
JPPCT/JP80/00297		1980-12-05
PCT/JP1981/000103 WO1982003859A1 (fr)	1980-12-05	1981-04-30	Derives de 1-sulfo-2-oxoazetidine et procede de preparation
JPPCT/JP81/00103		1981-04-30
JPPCT/JP81/00183		1981-08-21
PCT/JP1981/000183 WO1983000689A1 (fr)	1980-12-05	1981-08-21	Derives de 1-sulfo-2-oxoazetidine et leur procede de preparation
PCT/JP1981/000252 WO1983001063A1 (fr)	1980-12-05	1981-09-24	Derives de 1-sulfo-2-oxoazetidine et leur procede de preparation
JPPCT/JP81/00252		1981-09-24
EP81304996A EP0050965A1 (fr)	1980-10-23	1981-10-23	Composition inhibitrice de bêta-lactamase
JP56170634A JPS5798258A (en)	1980-10-23	1981-10-23	Beta-lactamase inhibitor composition
EP81304996.2		1981-10-23
JP170634/1981		1981-10-23

Publications (1)

Publication Number	Publication Date
CA1338539C true CA1338539C (fr)	1996-08-20

Family

ID=27561867

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000391401A Expired - Fee Related CA1338539C (fr)	1980-12-04	1981-12-03	Derives de la 1-sulfo-2-oxoazetidine et leur preparation

Country Status (1)

Country	Link
CA (1)	CA1338539C (fr)

1981
- 1981-12-03 CA CA000391401A patent/CA1338539C/fr not_active Expired - Fee Related

Publication	Publication Date	Title
EP0053816B1 (fr)	1988-05-04	Dérivés de 1-sulfo-2-azétidinone, leur préparation et leur utilisation
EP0093376B2 (fr)	1999-04-07	Dérivés de l'acide 2-azétidinone-1-sulfonique, leur préparation et leur utilisation
US4794108A (en)	1988-12-27	1-carboxymethoxy acetidinones and their production
CA1224784A (fr)	1987-07-28	Amides derives d'acides 2-oxo-1-azetidinesulfoniques
JPH03135973A (ja)	1991-06-10	アミノチアゾリル酢酸類
US4596869A (en)	1986-06-24	Pyridinyl and pyrimidinyl derivatives
NZ199168A (en)	1985-08-30	2-oxoazetidine derivatives and pharmaceutical compositions
FR2569195A1 (fr)	1986-02-21	Derives du 7-carboxymethoxyphenylacetamido-3-cepheme utiles comme medicaments antibacteriens et procedes pour leur preparation
US4363807A (en)	1982-12-14	Cepham compounds
US4725591A (en)	1988-02-16	β-lactamase inhibitory composition
CA1338539C (fr)	1996-08-20	Derives de la 1-sulfo-2-oxoazetidine et leur preparation
US4684724A (en)	1987-08-04	4-Cyano-2-azetidinones and production thereof
US4172198A (en)	1979-10-23	7-(N-substituted-2-phenylglycinamido)-3-substituted-3-cephem-4-carboxylic acid compounds and preparation thereof
DD236930A5 (de)	1986-06-25	Verfahren zur herstellung eines aktiven thioesters
US4771045A (en)	1988-09-13	2-oxozetidinone derivatives, their production and use
EP0100041B1 (fr)	1986-10-22	Dérivés de 1-sulpho-2-azétidinone, leur production et application
US4472300A (en)	1984-09-18	Azetidinone derivatives and process for preparation thereof
US4533495A (en)	1985-08-06	Method of producing 2-azetidinone-1-sulfonic acid compounds
KR890000226B1 (ko)	1989-03-11	1-술포-2-옥소아제티딘 유도체의 제조방법
CS253572B2 (cs)	1987-11-12	Způsob přípravy 1-sulfo-2-oxoazetidinu
CA1308109C (fr)	1992-09-29	Intermediaires pour la preparation de monosulfactames
EP0010667B1 (fr)	1983-07-20	Composés de céphame, compositions pharmaceutiques les contenant et procédés pour leur préparation et pour la préparation de composés de céphème connus
KR880000874B1 (ko)	1988-05-28	1-술포-2-옥소아제티딘 유도체의 제조방법
US4187374A (en)	1980-02-05	7-(β-Aminoacylamino)-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereof
JPS62289584A (ja)	1987-12-16	セフエム化合物およびその塩類

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