JPH0522719B2 - - Google Patents
Info
- Publication number
- JPH0522719B2 JPH0522719B2 JP59138206A JP13820684A JPH0522719B2 JP H0522719 B2 JPH0522719 B2 JP H0522719B2 JP 59138206 A JP59138206 A JP 59138206A JP 13820684 A JP13820684 A JP 13820684A JP H0522719 B2 JPH0522719 B2 JP H0522719B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- cyclopentano
- integer
- substituted
- abq
- Prior art date
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 125000006239 protecting group Chemical group 0.000 claims 10
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 55
- 239000000243 solution Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 238000001914 filtration Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000009518 sodium iodide Nutrition 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 229930186147 Cephalosporin Natural products 0.000 description 6
- 229940124587 cephalosporin Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- -1 cephalosporin compound Chemical class 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- MISJXUDJCSZFAH-UHFFFAOYSA-N 1-sulfanylpyridin-2-one Chemical compound SN1C=CC=CC1=O MISJXUDJCSZFAH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 3
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 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
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- RJLYMCRSFXYRPQ-FMOMHUKBSA-N benzhydryl (2r)-2-amino-3-aminooxypropanoate;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1C(OC(=O)[C@H](N)CON)C1=CC=CC=C1 RJLYMCRSFXYRPQ-FMOMHUKBSA-N 0.000 description 2
- SYPOLUBDFBZUAI-LMNIDFBRSA-N benzhydryl (6r)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@H]1N2C(C1N)=O)CC(COC(=O)C)=C2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 SYPOLUBDFBZUAI-LMNIDFBRSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- UKAUYVFTDYCKQA-UHFFFAOYSA-N homoserine Chemical compound OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003208 petroleum Substances 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- ORMUWUFDWFOUDV-UYLGBJQQSA-M sodium (6R)-4-(acetyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].C(C)(=O)OCC1S[C@H]2N(C(=C1)C(=O)[O-])C(C2)=O ORMUWUFDWFOUDV-UYLGBJQQSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SKNGHROBOKBHGJ-GORDUTHDSA-N (2e)-2-methoxyiminoacetamide Chemical compound CO\N=C\C(N)=O SKNGHROBOKBHGJ-GORDUTHDSA-N 0.000 description 1
- HNMBYRCXKASKEJ-YBBRRFGFSA-N (2r)-2-amino-3-aminooxypropanoic acid;dihydrochloride Chemical compound Cl.Cl.NOC[C@@H](N)C(O)=O HNMBYRCXKASKEJ-YBBRRFGFSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YMRVLINIIYCUHC-UHFFFAOYSA-N 2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CSC(NC(=O)CCl)=N1 YMRVLINIIYCUHC-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- OQFSYHWITGFERZ-UHFFFAOYSA-N 2-bromoethanesulfonic acid Chemical compound OS(=O)(=O)CCBr OQFSYHWITGFERZ-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- ADDBAPLLQRBDLT-UHFFFAOYSA-N 2-ethoxyiminoacetic acid Chemical compound CCON=CC(O)=O ADDBAPLLQRBDLT-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- RGBSGRUHELUMOF-UHFFFAOYSA-N 3,4-cyclopentenopyridine Natural products C1=NC=C2CCCC2=C1 RGBSGRUHELUMOF-UHFFFAOYSA-N 0.000 description 1
- PZEMWPDUXBZKJN-UHFFFAOYSA-N 4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CCO PZEMWPDUXBZKJN-UHFFFAOYSA-N 0.000 description 1
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 1
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- QGFMBZSDXHEQDN-HNNXBMFYSA-N benzhydryl (2S)-2-amino-4-hydroxybutanoate Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)OC([C@@H](N)CCO)=O QGFMBZSDXHEQDN-HNNXBMFYSA-N 0.000 description 1
- LANAHJANVAEXND-UHFFFAOYSA-N benzhydryl 2-[amino-[(2-methylpropan-2-yl)oxycarbonyloxy]amino]-4-hydroxybutanoate Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)OC(C(N(OC(=O)OC(C)(C)C)N)CCO)=O LANAHJANVAEXND-UHFFFAOYSA-N 0.000 description 1
- JNECHASMIHMFLY-UHFFFAOYSA-N benzhydryl 4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound C=1C=CC=CC=1C(OC(=O)C(CCO)NC(=O)OC(C)(C)C)C1=CC=CC=C1 JNECHASMIHMFLY-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- ZZSQFSQIEVZDMA-UHFFFAOYSA-N potassium;sulfane Chemical compound S.[K] ZZSQFSQIEVZDMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- JPJKQVVKHIZICB-FYZOBXCZSA-M sodium;(6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CCS[C@@H]2CC(=O)N12 JPJKQVVKHIZICB-FYZOBXCZSA-M 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Landscapes
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59138206A JPS6117589A (ja) | 1984-07-03 | 1984-07-03 | 新規セフアロスポリン誘導体及びその製造法 |
| US06/704,077 US4785090A (en) | 1984-02-23 | 1985-02-21 | Cephalosporin derivatives |
| KR1019850001075A KR920004820B1 (ko) | 1984-02-23 | 1985-02-21 | 새로운 세팔로스포린 유도체의 제조방법 |
| CA000474936A CA1276013C (en) | 1984-02-23 | 1985-02-22 | Cephalosporin derivatives |
| AT85101934T ATE66233T1 (de) | 1984-02-23 | 1985-02-22 | Cephalosporinverbindungen. |
| ES540664A ES8606360A1 (es) | 1984-02-23 | 1985-02-22 | Un derivado de cefalosporina. |
| DE8585101934T DE3583751D1 (de) | 1984-02-23 | 1985-02-22 | Cephalosporinverbindungen. |
| EP85101934A EP0153709B1 (en) | 1984-02-23 | 1985-02-22 | Novel cephalosporin derivatives |
| ES549498A ES8606361A1 (es) | 1984-02-23 | 1985-12-02 | Un procedimiento para la preparacion de nuevos derivados de cefalosporina. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59138206A JPS6117589A (ja) | 1984-07-03 | 1984-07-03 | 新規セフアロスポリン誘導体及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6117589A JPS6117589A (ja) | 1986-01-25 |
| JPH0522719B2 true JPH0522719B2 (xx) | 1993-03-30 |
Family
ID=15216561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59138206A Granted JPS6117589A (ja) | 1984-02-23 | 1984-07-03 | 新規セフアロスポリン誘導体及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6117589A (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH068299B2 (ja) * | 1986-12-18 | 1994-02-02 | 明治製菓株式会社 | 新規なセフアロスポリン誘導体 |
| US5143910A (en) * | 1989-09-07 | 1992-09-01 | Shionogi & Co., Ltd. | Piperaziniocephalosporins |
| DE102017115653A1 (de) | 2017-07-12 | 2019-01-17 | Festool Gmbh | Saugschlauch für einen Staubsauger |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54154787A (en) * | 1978-05-26 | 1979-12-06 | Glaxo Group Ltd | Cephalosporanic compound |
| JPS5810589A (ja) * | 1981-06-22 | 1983-01-21 | Fujisawa Pharmaceut Co Ltd | 新規セフエム化合物およびその製造法、並びに細菌感染症予防・治療剤 |
| JPS5890590A (ja) * | 1981-11-16 | 1983-05-30 | サノフイ・ソシエテ・アノニム | 新規なセフアロスポリンおよびその製法 |
| JPS60178890A (ja) * | 1984-02-23 | 1985-09-12 | Meiji Seika Kaisha Ltd | 新規セフアロスポリン誘導体およびその製造法 |
-
1984
- 1984-07-03 JP JP59138206A patent/JPS6117589A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54154787A (en) * | 1978-05-26 | 1979-12-06 | Glaxo Group Ltd | Cephalosporanic compound |
| JPS5810589A (ja) * | 1981-06-22 | 1983-01-21 | Fujisawa Pharmaceut Co Ltd | 新規セフエム化合物およびその製造法、並びに細菌感染症予防・治療剤 |
| JPS5890590A (ja) * | 1981-11-16 | 1983-05-30 | サノフイ・ソシエテ・アノニム | 新規なセフアロスポリンおよびその製法 |
| JPS60178890A (ja) * | 1984-02-23 | 1985-09-12 | Meiji Seika Kaisha Ltd | 新規セフアロスポリン誘導体およびその製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6117589A (ja) | 1986-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0313237B2 (xx) | ||
| JPS5946954B2 (ja) | 抗生物質の製法 | |
| JPH0362711B2 (xx) | ||
| DK149062B (da) | Analogifremgangsmaade til fremstilling af cefuroximestere | |
| JPH02311483A (ja) | セフトリアキソンの製造方法 | |
| US4546176A (en) | 7-Carboxymethoxyphenylacetamido-3-cephem derivatives and antibacterial preparations containing the same | |
| CH642662A5 (de) | Cephalosporine und verfahren zu deren herstellung. | |
| FI63586B (fi) | Foerfarande foer framstaellning av 7-beta-(2-oxiimino-2-arylacetamido)-3-(sulfoalkyltetrazol-5-yltiometyl)-3-cefem-4-karboxylsyror med antibakteriell verkan | |
| CS262674B2 (en) | Process for preparing heat stable crystalline cephalosporines | |
| GB2092575A (en) | 7-acylaminocephalosporanic acid derivatives | |
| CA1050531A (en) | Process for preparing cephalosporin derivatives | |
| JPH0522719B2 (xx) | ||
| JPS62491A (ja) | ３−（置換）プロペニルアミノチアゾリルセフアロスポラン酸およびそのエステル | |
| US4247548A (en) | 7α-Methoxycephalosporin derivatives and their pharmaceutical compositions having antibacterial activity | |
| US3928333A (en) | Process for the preparation of 3 cephalosporin esters | |
| JPS596308B2 (ja) | テトラゾ−ルチオ−ル誘導体 | |
| JPS6310707B2 (xx) | ||
| EP0070706A2 (en) | Cephalosporin compounds | |
| US4115646A (en) | Process for preparing 7-aminocephalosporanic acid derivatives | |
| JPS60260584A (ja) | セフアロスポリン誘導体 | |
| KR950008321B1 (ko) | 세펨 유도체 | |
| JPS6053026B2 (ja) | テトラゾ−ルチオ−ル誘導体 | |
| KR790001503B1 (ko) | △3-세팔로스포린 에스테르의 제조방법 | |
| CS196272B2 (en) | Method of producing delta up 3-cephalosporin esters | |
| JPS60120888A (ja) | セフェム誘導体 |