JPS6129956B2 - - Google Patents

Info

Publication number: JPS6129956B2
Authority: JP; Japan
Prior art keywords: oxo; acid; methyl; dihydro; formula
Prior art date: 1974-07-08
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

Application number

JP50084346A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5134190A (en

Inventor

Buroieru Heruman

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.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

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.)

1974-07-08

Filing date

1975-07-08

Publication date

1986-07-10

1974-07-08 Priority claimed from US486542A external-priority patent/US3929782A/en

1975-07-08 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1976-03-23 Publication of JPS5134190A publication Critical patent/JPS5134190A/ja

1986-07-10 Publication of JPS6129956B2 publication Critical patent/JPS6129956B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229930186147 Cephalosporin Natural products 0.000 claims description 4
229940124587 cephalosporin Drugs 0.000 claims description 4
150000001780 cephalosporins Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
-1 7-aminocephalosporanic acid compound Chemical class 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 23
239000002253 acid Substances 0.000 description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 15
239000000203 mixture Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000000034 method Methods 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012346 acetyl chloride Substances 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
125000000446 sulfanediyl group Chemical group *S* 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
LQUWADVPDDPELS-UHFFFAOYSA-N 2-(5-oxo-2h-1,2,4-oxadiazol-3-yl)-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1=NOC(=O)N1 LQUWADVPDDPELS-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
238000004140 cleaning Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 description 2
PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical compound O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 description 2
LJXPALUWVNDHRT-UHFFFAOYSA-N 3-(thiophen-2-ylmethyl)-5-(trichloromethyl)-1,2,4-oxadiazole Chemical compound O1C(C(Cl)(Cl)Cl)=NC(CC=2SC=CC=2)=N1 LJXPALUWVNDHRT-UHFFFAOYSA-N 0.000 description 2
VJUMTDFMVOOCKK-UHFFFAOYSA-N 3-benzyl-2h-1,2,4-oxadiazol-5-one Chemical compound O1C(O)=NC(CC=2C=CC=CC=2)=N1 VJUMTDFMVOOCKK-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000193996 Streptococcus pyogenes Species 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000000249 desinfective effect Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
239000006186 oral dosage form Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
150000005071 1,2,4-oxadiazoles Chemical class 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
DFFJRZQBFKVZCU-UHFFFAOYSA-N 2-(2h-oxadiazol-3-yl)acetic acid Chemical compound OC(=O)CN1NOC=C1 DFFJRZQBFKVZCU-UHFFFAOYSA-N 0.000 description 1
UFDRMVSAVLUJCV-UHFFFAOYSA-N 2-(5-oxo-2h-1,2,4-oxadiazol-3-yl)-2-thiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(C(=O)O)C1=NOC(=O)N1 UFDRMVSAVLUJCV-UHFFFAOYSA-N 0.000 description 1
YJVXEQJVAOGXKM-UHFFFAOYSA-N 2-ethoxy-2h-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(O)=O)C(OCC)C=CC2=C1 YJVXEQJVAOGXKM-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 description 1
BKSWBXKELOQRGD-UHFFFAOYSA-N 3-(thiophen-2-ylmethyl)-2h-1,2,4-oxadiazol-5-one Chemical compound O1C(=O)NC(CC=2SC=CC=2)=N1 BKSWBXKELOQRGD-UHFFFAOYSA-N 0.000 description 1
PEADFXIZRFVTIP-UHFFFAOYSA-N 3-benzyl-4-methyl-1,2,4-oxadiazol-5-one Chemical compound O1C(=O)N(C)C(CC=2C=CC=CC=2)=N1 PEADFXIZRFVTIP-UHFFFAOYSA-N 0.000 description 1
HZYYPAZDJHOJTH-UHFFFAOYSA-N 3-benzyl-5-(trichloromethyl)-1,2,4-oxadiazole Chemical compound O1C(C(Cl)(Cl)Cl)=NC(CC=2C=CC=CC=2)=N1 HZYYPAZDJHOJTH-UHFFFAOYSA-N 0.000 description 1
FASWFFAQTUBTSL-UHFFFAOYSA-N 3-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound S1C(=O)C(C(=O)O)N2CCC21 FASWFFAQTUBTSL-UHFFFAOYSA-N 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
CTQPPUPWHLGKOB-UHFFFAOYSA-N 4h-oxadiazol-5-one Chemical compound O=C1CN=NO1 CTQPPUPWHLGKOB-UHFFFAOYSA-N 0.000 description 1
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 1
241000234282 Allium Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000005973 Carvone Substances 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
206010017533 Fungal infection Diseases 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
241000256215 Spongomorpha aeruginosa Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
150000007960 acetonitrile Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
SYPOLUBDFBZUAI-XMSQKQJNSA-N benzhydryl (6r,7r)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@H]1N2C([C@H]1N)=O)CC(COC(=O)C)=C2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 SYPOLUBDFBZUAI-XMSQKQJNSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000013365 dairy product Nutrition 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
244000144972 livestock Species 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
LHSWRTYGIVUVHO-UHFFFAOYSA-N n'-hydroxy-2-thiophen-2-ylethanimidamide Chemical compound ON=C(N)CC1=CC=CS1 LHSWRTYGIVUVHO-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- 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
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

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

JP50084346A 1974-07-08 1975-07-08 Penishirinruioyobi sefuarosuhorinruino seiho Granted JPS5134190A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US486542A US3929782A (en)	1974-03-13	1974-07-08	1,2,4-Oxadiazolonylacetyl cephalosporins

Publications (2)

Publication Number	Publication Date
JPS5134190A JPS5134190A (en)	1976-03-23
JPS6129956B2 true JPS6129956B2 (fr)	1986-07-10

Family

ID=23932297

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP50084346A Granted JPS5134190A (en)	1974-07-08	1975-07-08	Penishirinruioyobi sefuarosuhorinruino seiho

Country Status (3)

Country	Link
JP (1)	JPS5134190A (fr)
CA (1)	CA1068679A (fr)
DE (1)	DE2529089A1 (fr)

1975
- 1975-06-10 CA CA228,973A patent/CA1068679A/fr not_active Expired
- 1975-06-30 DE DE19752529089 patent/DE2529089A1/de not_active Withdrawn
- 1975-07-08 JP JP50084346A patent/JPS5134190A/ja active Granted

Also Published As

Publication number	Publication date
JPS5134190A (en)	1976-03-23
CA1068679A (fr)	1979-12-25
DE2529089A1 (de)	1976-01-22

Publication	Publication Date	Title
DK144763B (da)	1982-06-01	Analogifremgangsmaade til fremstilling af cephalosporinderivater
US3634405A (en)	1972-01-11	Synthetic penicillins
JPH0140837B2 (fr)	1989-08-31
DK174331B1 (da)	2002-12-09	Krystalliserede cephem-syreadditionssalte, dets fremstilling og anvendelse til fremstilling af et lægemiddel samt lægemiddel indeholdende saltet
DK145262B (da)	1982-10-18	Analogifremgangsmaade til fremstilling af cephalosporansyrederivater og estere og salte deraf
US4104469A (en)	1978-08-01	7-(Syn-α-alkoxy-iminofuryl)acetamido-3-(2-methyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US3919208A (en)	1975-11-11	7-(Cyanomethylaryl)acetamide-cephalosporin derivatives
US4103085A (en)	1978-07-25	7-(Syn-α-alkoxy-iminofurylacetamido-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US3960849A (en)	1976-06-01	Amino-1,2,4-oxadiazolyl-3-acetyl cephalosporins
JPS5953273B2 (ja)	1984-12-24	シアノメチルチオアセチルセフアロスポリン類の製造法
US3929782A (en)	1975-12-30	1,2,4-Oxadiazolonylacetyl cephalosporins
JPS6129956B2 (fr)	1986-07-10
JPS5823378B2 (ja)	1983-05-14	抗バクテリア剤中間体の合成法
US3720664A (en)	1973-03-13	Alpha-ureidocyclohexadienylalkylene-penicillins
JPS6133825B2 (fr)	1986-08-04
US4182863A (en)	1980-01-08	7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
US4160829A (en)	1979-07-10	Antibacterial 1,2,4-oxadiazolylacetamido cephalosporins
US3959259A (en)	1976-05-25	1,2,4-Oxadiazolonylacetyl penicillins
US3994889A (en)	1976-11-30	3-Heterothio derivatives of (α-thiocarbonylaminol)-7α-methoxy-cephalosporins
US3996219A (en)	1976-12-07	3-Heterothio derivatives of (α-thiocarbonylamino) cephalosporins
US3996216A (en)	1976-12-07	3-Heterothio derivatives of (formylamino)acetylamino-7-alpha-methoxy cephalosporins
US4128724A (en)	1978-12-05	Hydrazinocarbonylamino cephalosporins
US4180658A (en)	1979-12-25	7[-2-Alkoxyamino(acetamido)]cephalosporin derivatives
US3859274A (en)	1975-01-07	Acylthiomethyl esters of penicillins
US3931170A (en)	1976-01-06	3-Heterothio derivatives of (carbamoylthioacetyl)cephalosporins