CH629208A5 - Verfahren zur herstellung von neuen arylmalonamido-1-oxadethiacephalosporinen. - Google Patents
Verfahren zur herstellung von neuen arylmalonamido-1-oxadethiacephalosporinen. Download PDFInfo
- Publication number
- CH629208A5 CH629208A5 CH383177A CH383177A CH629208A5 CH 629208 A5 CH629208 A5 CH 629208A5 CH 383177 A CH383177 A CH 383177A CH 383177 A CH383177 A CH 383177A CH 629208 A5 CH629208 A5 CH 629208A5
- Authority
- CH
- Switzerland
- Prior art keywords
- cephem
- oxadethia
- thiomethyl
- mixture
- methoxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 p-hydroxyphenyl Chemical group 0.000 claims description 148
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 42
- 125000002252 acyl group Chemical group 0.000 claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- CJVFIJXEPCVCTK-LWMBYGOMSA-N (2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-methylbutanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](N)C(C)C)C(C)C CJVFIJXEPCVCTK-LWMBYGOMSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 291
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 285
- 239000000203 mixture Substances 0.000 description 163
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 144
- 239000000243 solution Substances 0.000 description 139
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 124
- 235000019439 ethyl acetate Nutrition 0.000 description 97
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 85
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 76
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 238000003756 stirring Methods 0.000 description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 39
- 239000000843 powder Substances 0.000 description 38
- 238000001816 cooling Methods 0.000 description 31
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 30
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 235000017557 sodium bicarbonate Nutrition 0.000 description 26
- 239000006260 foam Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 229940086542 triethylamine Drugs 0.000 description 22
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 21
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 125000006239 protecting group Chemical group 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 13
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- 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 12
- 125000005982 diphenylmethyl group Chemical class [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 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 125000005633 phthalidyl group Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 9
- 230000010933 acylation Effects 0.000 description 9
- 238000005917 acylation reaction Methods 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 8
- 125000003368 amide group Chemical group 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 7
- 229940124587 cephalosporin Drugs 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- 150000007530 organic bases Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
- 230000009471 action Effects 0.000 description 5
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- 239000002585 base Substances 0.000 description 5
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
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- 230000000694 effects Effects 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 4
- 229930186147 Cephalosporin Natural products 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- 150000001780 cephalosporins Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
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- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005042 acyloxymethyl group Chemical group 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000036765 blood level Effects 0.000 description 3
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- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000002221 trityl group Chemical class [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 3
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- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
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- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
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- 125000003460 beta-lactamyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
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- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- GXVPDDAKKBHBED-UHFFFAOYSA-N n,n-diethyl-2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN(CC)CC)C1=CC=CC=C1 GXVPDDAKKBHBED-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 201000004537 pyelitis Diseases 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 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
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3340176A JPS52122386A (en) | 1976-03-25 | 1976-03-25 | Cephalosporin analogous compounds as antibacterials |
| JP5029576A JPS52133997A (en) | 1976-04-30 | 1976-04-30 | Cephalosporin antibiotics |
| AU53625/79A AU528617B2 (en) | 1976-03-25 | 1979-12-07 | 1-oxadethia-cephalosporin antibiotics |
| AU57286/80A AU531661B2 (en) | 1976-03-25 | 1980-04-09 | 1-oxadethia-cephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629208A5 true CH629208A5 (de) | 1982-04-15 |
Family
ID=27423456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH383177A CH629208A5 (de) | 1976-03-25 | 1977-03-25 | Verfahren zur herstellung von neuen arylmalonamido-1-oxadethiacephalosporinen. |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US4138486A (enExample) |
| AT (1) | AT353959B (enExample) |
| AU (4) | AU510169B2 (enExample) |
| BE (1) | BE852912A (enExample) |
| CA (1) | CA1085392A (enExample) |
| CH (1) | CH629208A5 (enExample) |
| FR (1) | FR2345452A1 (enExample) |
| GB (1) | GB1547351A (enExample) |
| NL (1) | NL176074C (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1085392A (en) * | 1976-03-25 | 1980-09-09 | Masayuki Narisada | Arylmalonamido-1-oxadethiacephalosporins |
| US4180571A (en) * | 1976-03-25 | 1979-12-25 | Shionogi & Co., Ltd. | Arylmalonamido-1-oxadethiacephalosporins |
| AU514377B2 (en) * | 1977-02-15 | 1981-02-05 | Shionogi & Co., Ltd. | l-OXADETHIACEPHAM COMPOUNDS |
| US4533730A (en) * | 1977-02-15 | 1985-08-06 | Shionogi & Co., Ltd. | 1-Oxadethiacepham compounds |
| US4443598A (en) * | 1977-02-15 | 1984-04-17 | Shionogi & Co., Ltd. | 1-Oxadethiacepham compounds |
| CA1100962A (en) * | 1977-04-28 | 1981-05-12 | Yoshio Hamashima | Haloarylmalonamidooxacephalosporins |
| JPS5419990A (en) * | 1977-07-14 | 1979-02-15 | Shionogi & Co Ltd | Dihydrotriazinylthioxacephalosporin |
| JPS609718B2 (ja) * | 1977-08-25 | 1985-03-12 | 塩野義製薬株式会社 | チアジアゾリルチオセフアロスポリン類縁抗生物質 |
| US4259485A (en) * | 1979-04-24 | 1981-03-31 | Eli Lilly And Company | Crystallization process |
| US4252953A (en) * | 1979-05-01 | 1981-02-24 | Eli Lilly And Company | Antibiotic crystalline epimer |
| JPS5690088A (en) * | 1979-11-02 | 1981-07-21 | Meiji Seika Kaisha Ltd | Novel cephalosporin analog compound |
| JPS56103185A (en) * | 1980-01-22 | 1981-08-18 | Shionogi & Co Ltd | Malonamidoxa-dethia-cephem compound |
| US4452778A (en) * | 1980-03-31 | 1984-06-05 | Eli Lilly And Company | Synergistic antibacterial compositions and method of treatment of infections caused by multiple antibiotic-resistant organisms |
| US4304774A (en) * | 1980-09-17 | 1981-12-08 | Eli Lilly And Company | Bis-tetrazolmethyl substituted β-lactam antibiotics |
| US4301282A (en) * | 1980-09-17 | 1981-11-17 | Eli Lilly And Company | 1-Oxa-β-lactam antibiotics |
| US4368156A (en) * | 1981-03-09 | 1983-01-11 | Eli Lilly And Company | Preparation of 4-haloazetidin-2-ones from 4-sulfinoazetidin-2-ones |
| DE3269313D1 (en) * | 1981-05-14 | 1986-04-03 | Beecham Group Plc | Process for the preparation of an enantiomer of a beta-lactam derivative |
| JPS5857360A (ja) * | 1981-10-01 | 1983-04-05 | Ajinomoto Co Inc | アゼチジノン誘導体 |
| US4391975A (en) * | 1981-12-15 | 1983-07-05 | Queen's University At Kingston | Process for 1-oxacephem derivatives |
| US4552763A (en) * | 1981-12-21 | 1985-11-12 | Eli Lilly And Company | Synergistic antibacterial compositions and method of treatment of infections caused by multiple antibiotic-resistant organisms |
| US4594247A (en) * | 1981-12-21 | 1986-06-10 | Eli Lilly And Company | Synergistic antibacterial compositions and method of treatment of infections caused by multiple antibiotic-resistant organisms |
| JPS597193A (ja) * | 1982-07-02 | 1984-01-14 | Shionogi & Co Ltd | マロニルメチル基の異性化方法 |
| US4472576A (en) * | 1982-12-03 | 1984-09-18 | Merck & Co., Inc. | Processes for the production of antibiotic 1-oxadethiacephalosporins |
| JPS59152385A (ja) * | 1983-02-17 | 1984-08-31 | Shionogi & Co Ltd | ヒドロキサム酸系セフアロスポリン誘導体 |
| SE8301182D0 (sv) * | 1983-03-04 | 1983-03-04 | Haessle Ab | Novel compounds |
| JPS60123490A (ja) * | 1983-12-07 | 1985-07-02 | Shionogi & Co Ltd | マロニルオキサセフェムカルボン酸誘導体 |
| SK13897A3 (en) | 1996-02-06 | 1998-05-06 | Pliva Pharm & Chem Works | 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, method for preparation thereof and their use |
| US6426342B2 (en) * | 1999-08-16 | 2002-07-30 | Revaax Pharmaceuticals, Llc | Use of β-lactamase inhibitors as neuroprotectants |
| ES2258980T3 (es) * | 1999-08-16 | 2006-09-16 | Revaax Pharmaceuticals Llc | Composiciones farmaceuticas que comprenden acido clavulanico o derivados del mismo para el tratamiento de trastornos del comportamiento. |
| US6489319B2 (en) * | 1999-08-16 | 2002-12-03 | Revaax Pharmaceuticals, Llc | Neurotherapeutic use of carboxypeptidase inhibitors |
| KR20050083971A (ko) * | 2002-11-22 | 2005-08-26 | 더 존스 홉킨스 유니버시티 | 인지능 손상의 치료를 위한 표적 |
| US20100255099A1 (en) * | 2007-10-26 | 2010-10-07 | Rexahn Pharmaceuticals, Inc. | Clavulanate formulation for neuroprotection and treatment of neurodegenerative disorders |
| CN102260280A (zh) * | 2010-05-28 | 2011-11-30 | 上海医药工业研究院 | 拉氧头孢钠的制备方法 |
| CN102603784B (zh) * | 2012-04-06 | 2014-12-31 | 浙江惠迪森药业有限公司 | 一种拉氧头孢氯化铝(锡)苯甲醚络合物及其制备方法和应用 |
| CN102827191B (zh) * | 2012-09-24 | 2015-03-11 | 浙江东邦药业有限公司 | 一种氧头孢类化合物的制备方法 |
| CN107383066A (zh) * | 2017-07-31 | 2017-11-24 | 山西千岫制药有限公司 | 一种拉氧头孢酸去保护基的方法 |
| KR102115644B1 (ko) * | 2017-09-13 | 2020-05-27 | 주식회사 동도물산 | 7α-알콕시옥사세펨 중간체의 제조방법 |
| CN117069739A (zh) * | 2023-08-17 | 2023-11-17 | 山西千岫制药有限公司 | 一种高纯度拉氧头孢钠的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1914366U (de) | 1965-01-08 | 1965-04-22 | Otto Liebmann Fa | Schutzhuelle fuer zigarettenschachteln oder -packungen. |
| US3769277A (en) * | 1970-01-23 | 1973-10-30 | Glaxo Lab Ltd | Preparation of delta3-4 carboxy cephalosporins having a 3-vinyl or substituted 3-vinyl group |
| US3728342A (en) * | 1970-12-03 | 1973-04-17 | Lilly Co Eli | 3-acyloxymethyl cephalosporins and method of preparation |
| US3795672A (en) * | 1971-06-09 | 1974-03-05 | Lilly Co Eli | Process for the preparation of delta2-cephem-4-carboxylic acid esters |
| NL7314706A (enExample) | 1972-11-06 | 1974-05-08 | ||
| NL178005C (nl) | 1972-11-06 | 1986-01-02 | Merck & Co Inc | Werkwijze voor het bereiden van een farmaceutisch preparaat met antibacteriele werking, alsmede werkwijze ter bereiding van een cefalosporine-antibioticum. |
| GB1510794A (en) * | 1974-08-06 | 1978-05-17 | Univ Kingston | 1-oxacephems and intermediates therefor |
| US4011216A (en) * | 1975-04-11 | 1977-03-08 | Bristol-Myers Company | Δ2,3-0-2-Isocephem-4-carboxylic acid and derivatives thereof as antibacterial agents |
| US4013648A (en) * | 1975-07-23 | 1977-03-22 | Bristol-Myers Company | Δ2,3 -0-2-Isocephem-4-carboxylic acid and derivatives as antibacterial agents |
| CA1085392A (en) * | 1976-03-25 | 1980-09-09 | Masayuki Narisada | Arylmalonamido-1-oxadethiacephalosporins |
| US4180571A (en) * | 1976-03-25 | 1979-12-25 | Shionogi & Co., Ltd. | Arylmalonamido-1-oxadethiacephalosporins |
-
1977
- 1977-03-18 CA CA274,261A patent/CA1085392A/en not_active Expired
- 1977-03-22 AU AU23508/77A patent/AU510169B2/en not_active Expired
- 1977-03-22 US US05/780,183 patent/US4138486A/en not_active Expired - Lifetime
- 1977-03-23 GB GB12326/77A patent/GB1547351A/en not_active Expired
- 1977-03-24 AT AT205777A patent/AT353959B/de not_active IP Right Cessation
- 1977-03-25 BE BE176149A patent/BE852912A/xx not_active IP Right Cessation
- 1977-03-25 NL NLAANVRAGE7703282,A patent/NL176074C/xx not_active IP Right Cessation
- 1977-03-25 FR FR7709107A patent/FR2345452A1/fr active Granted
- 1977-03-25 CH CH383177A patent/CH629208A5/de not_active IP Right Cessation
-
1979
- 1979-12-07 AU AU53624/79A patent/AU527733B2/en not_active Expired
- 1979-12-07 AU AU53625/79A patent/AU528617B2/en not_active Expired
-
1980
- 1980-04-09 AU AU57286/80A patent/AU531661B2/en not_active Expired
- 1980-06-05 US US06/156,872 patent/US4323567A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU528617B2 (en) | 1983-05-05 |
| AU510169B2 (en) | 1980-06-12 |
| ATA205777A (de) | 1979-05-15 |
| AU5362579A (en) | 1980-05-01 |
| BE852912A (fr) | 1977-09-26 |
| CA1085392A (en) | 1980-09-09 |
| GB1547351A (en) | 1979-06-13 |
| AU531661B2 (en) | 1983-09-01 |
| AT353959B (de) | 1979-12-10 |
| AU5362479A (en) | 1980-05-01 |
| US4138486A (en) | 1979-02-06 |
| AU2350877A (en) | 1978-09-28 |
| FR2345452B1 (enExample) | 1980-07-25 |
| US4323567A (en) | 1982-04-06 |
| AU527733B2 (en) | 1983-03-17 |
| NL7703282A (nl) | 1977-09-27 |
| FR2345452A1 (fr) | 1977-10-21 |
| NL176074C (nl) | 1985-02-18 |
| NL176074B (nl) | 1984-09-17 |
| AU5728680A (en) | 1980-06-19 |
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