DK141100B - Fremgangsmåde til fremstilling af 7-acylamido-3-cephem-4-carboxylsyrer. - Google Patents
Fremgangsmåde til fremstilling af 7-acylamido-3-cephem-4-carboxylsyrer. Download PDFInfo
- Publication number
- DK141100B DK141100B DK647572AA DK647572A DK141100B DK 141100 B DK141100 B DK 141100B DK 647572A A DK647572A A DK 647572AA DK 647572 A DK647572 A DK 647572A DK 141100 B DK141100 B DK 141100B
- Authority
- DK
- Denmark
- Prior art keywords
- acid
- cephem
- added
- amino
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 cyano, hydroxy Chemical group 0.000 claims description 44
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- RJFPBECTFIUTHB-INEUFUBQSA-N (6r,7r)-7-azaniumyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 RJFPBECTFIUTHB-INEUFUBQSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 235000013312 flour Nutrition 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 91
- 239000000203 mixture Substances 0.000 description 59
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- 239000002253 acid Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 27
- 239000013078 crystal Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 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 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 13
- 150000008065 acid anhydrides Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- NVIAYEIXYQCDAN-HWZXHQHMSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 6
- 239000003125 aqueous solvent Substances 0.000 description 6
- 239000002198 insoluble material Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 150000004682 monohydrates Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229930186147 Cephalosporin Natural products 0.000 description 5
- 229930182555 Penicillin Natural products 0.000 description 5
- 229940124587 cephalosporin Drugs 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- HSHGZXNAXBPPDL-IOJJLOCKSA-N (6r)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 HSHGZXNAXBPPDL-IOJJLOCKSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 150000001780 cephalosporins Chemical class 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- WOEWMGJSTHBCRB-HWZXHQHMSA-N (6R)-7-amino-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC1[C@@H]2N(C(=C(CS2)CN=[N+]=[N-])C(=O)O)C1=O WOEWMGJSTHBCRB-HWZXHQHMSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
- 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 2
- 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 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- AVGYWQBCYZHHPN-DLFVXPSJSA-N O.N[C@@H](C(=O)NC1[C@@H]2N(C(=C(CS2)C)C(=O)O)C1=O)C1=CC=CC=C1 Chemical compound O.N[C@@H](C(=O)NC1[C@@H]2N(C(=C(CS2)C)C(=O)O)C1=O)C1=CC=CC=C1 AVGYWQBCYZHHPN-DLFVXPSJSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002081 enamines Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 238000005406 washing Methods 0.000 description 2
- FUBBGQLTSCSAON-HTCLMOQTSA-N (6R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N[C@@H](C(=O)NC1[C@@H]2N(C(=C(CS2)COC(C)=O)C(=O)O)C1=O)C1=CC=CC=C1 FUBBGQLTSCSAON-HTCLMOQTSA-N 0.000 description 1
- LEVGFKLCQCLKRP-IQQIRFCMSA-N (6R)-4-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N[C@@H](C(=O)NC1S[C@H]2N(C(=C1C)C(=O)O)C(C2)=O)C1=CC=CC=C1 LEVGFKLCQCLKRP-IQQIRFCMSA-N 0.000 description 1
- BOEGTKLJZSQCCD-MKOUYDOKSA-N (6R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N[C@@H](C(=O)NC1[C@@H]2N(C(=C(CS2)C)C(=O)O)C1=O)C1=CC=C(C=C1)O BOEGTKLJZSQCCD-MKOUYDOKSA-N 0.000 description 1
- FZDRVLJSDYQRPO-HWZXHQHMSA-N (6r)-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2CC(=O)N21 FZDRVLJSDYQRPO-HWZXHQHMSA-N 0.000 description 1
- IPZYFTKPGPTHNK-JLOHTSLTSA-N (6r)-7-amino-3-(benzoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1COC(=O)C1=CC=CC=C1 IPZYFTKPGPTHNK-JLOHTSLTSA-N 0.000 description 1
- FAKMUWSCVNYPHG-IOJJLOCKSA-N (6r)-7-amino-3-[(5-methyl-1,3,4-oxadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 FAKMUWSCVNYPHG-IOJJLOCKSA-N 0.000 description 1
- BDSDFCVDQUGOFB-XNCJUZBTSA-N (6s,7s)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC)=C(C(O)=O)N2C(=O)[C@H](N)[C@H]12 BDSDFCVDQUGOFB-XNCJUZBTSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ARAFEULRMHFMDE-UHFFFAOYSA-N 1,3-oxazolidine-2,5-dione Chemical compound O=C1CNC(=O)O1 ARAFEULRMHFMDE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- OVIHQCKYIOKFFX-UHFFFAOYSA-N 1-piperidin-1-ylbutane-1,3-dione Chemical compound CC(=O)CC(=O)N1CCCCC1 OVIHQCKYIOKFFX-UHFFFAOYSA-N 0.000 description 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- XNKWTOZWDSBIST-UHFFFAOYSA-N 2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)C(N)C1=CC(Cl)=C(O)C(Cl)=C1 XNKWTOZWDSBIST-UHFFFAOYSA-N 0.000 description 1
- FLZDFFKRJPLFGS-UHFFFAOYSA-N 2-amino-2-(3-chloro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)C(N)C1=CC=C(O)C(Cl)=C1 FLZDFFKRJPLFGS-UHFFFAOYSA-N 0.000 description 1
- GVVFCAFBYHYGEE-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride;hydron;chloride Chemical compound Cl.ClC(=O)C(N)C1=CC=CC=C1 GVVFCAFBYHYGEE-UHFFFAOYSA-N 0.000 description 1
- GXUAKXUIILGDKW-UHFFFAOYSA-N 2-azaniumyl-2-(4-methoxyphenyl)acetate Chemical compound COC1=CC=C(C(N)C(O)=O)C=C1 GXUAKXUIILGDKW-UHFFFAOYSA-N 0.000 description 1
- ZWKWPONGVMNKOM-UHFFFAOYSA-N 2-azaniumyl-2-(4-methylsulfanylphenyl)acetate Chemical compound CSC1=CC=C(C(N)C(O)=O)C=C1 ZWKWPONGVMNKOM-UHFFFAOYSA-N 0.000 description 1
- XLMSKXASROPJNG-UHFFFAOYSA-N 2-azaniumyl-2-thiophen-2-ylacetate Chemical compound OC(=O)C(N)C1=CC=CS1 XLMSKXASROPJNG-UHFFFAOYSA-N 0.000 description 1
- XUICXMXDTICQOZ-UHFFFAOYSA-N 2-azido-2-phenylacetic acid Chemical compound [N-]=[N+]=NC(C(=O)O)C1=CC=CC=C1 XUICXMXDTICQOZ-UHFFFAOYSA-N 0.000 description 1
- KWGQOJWITMQEOT-UHFFFAOYSA-N 2-benzhydryloxyacetic acid Chemical compound C=1C=CC=CC=1C(OCC(=O)O)C1=CC=CC=C1 KWGQOJWITMQEOT-UHFFFAOYSA-N 0.000 description 1
- WAKFRZBXTKUFIW-UHFFFAOYSA-N 2-bromo-2-phenylacetic acid Chemical compound OC(=O)C(Br)C1=CC=CC=C1 WAKFRZBXTKUFIW-UHFFFAOYSA-N 0.000 description 1
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical compound OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- XEPIKYPNVRIQJA-UHFFFAOYSA-N 2-methylsulfanyl-2-phenylacetic acid Chemical compound CSC(C(O)=O)C1=CC=CC=C1 XEPIKYPNVRIQJA-UHFFFAOYSA-N 0.000 description 1
- RZCJYMOBWVJQGV-UHFFFAOYSA-N 2-naphthyloxyacetic acid Chemical compound C1=CC=CC2=CC(OCC(=O)O)=CC=C21 RZCJYMOBWVJQGV-UHFFFAOYSA-N 0.000 description 1
- TVSPPYGAFOVROT-UHFFFAOYSA-N 2-phenoxybutanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC=C1 TVSPPYGAFOVROT-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- ZHRDJBQJJRPNOP-UHFFFAOYSA-N 2-pyridin-4-ylethanethioyl chloride;hydrochloride Chemical compound Cl.ClC(=S)CC1=CC=NC=C1 ZHRDJBQJJRPNOP-UHFFFAOYSA-N 0.000 description 1
- AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 1
- VXNINNWMDGTACV-UHFFFAOYSA-N 3-oxo-n-propylbutanamide Chemical compound CCCNC(=O)CC(C)=O VXNINNWMDGTACV-UHFFFAOYSA-N 0.000 description 1
- CWSGHOHNZXYRER-UHFFFAOYSA-N 3-oxobutanoic acid;propan-2-one Chemical compound CC(C)=O.CC(=O)CC(O)=O CWSGHOHNZXYRER-UHFFFAOYSA-N 0.000 description 1
- SBSYFELXUYBRND-UHFFFAOYSA-N 3-phenoxypropanoyl chloride Chemical compound ClC(=O)CCOC1=CC=CC=C1 SBSYFELXUYBRND-UHFFFAOYSA-N 0.000 description 1
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 description 1
- PENHKTNQUJMHIR-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=CC=CC=C1 PENHKTNQUJMHIR-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- IWYDBHQHNPBIQZ-UHFFFAOYSA-N C(=O)=CC(C)=O.ClC1=C(N)C=CC(=C1)Cl Chemical compound C(=O)=CC(C)=O.ClC1=C(N)C=CC(=C1)Cl IWYDBHQHNPBIQZ-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000004725 beta keto acid derivatives Chemical class 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000004723 keto acid derivatives Chemical class 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- REYAJCIAOQNQTF-UHFFFAOYSA-N n-ethyl-3-oxobutanamide Chemical compound CCNC(=O)CC(C)=O REYAJCIAOQNQTF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22017271 | 1971-12-28 | ||
| JP22027271 | 1971-12-28 | ||
| JP22027271 | 1971-12-28 | ||
| JP22017271 | 1971-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141100B true DK141100B (da) | 1980-01-14 |
| DK141100C DK141100C (enrdf_load_html_response) | 1980-06-16 |
Family
ID=26523569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK647572AA DK141100B (da) | 1971-12-28 | 1972-12-27 | Fremgangsmåde til fremstilling af 7-acylamido-3-cephem-4-carboxylsyrer. |
Country Status (6)
| Country | Link |
|---|---|
| CS (1) | CS185615B2 (enrdf_load_html_response) |
| DD (1) | DD101897A5 (enrdf_load_html_response) |
| DK (1) | DK141100B (enrdf_load_html_response) |
| ES (1) | ES410069A1 (enrdf_load_html_response) |
| HU (1) | HU169409B (enrdf_load_html_response) |
| PL (1) | PL82166B1 (enrdf_load_html_response) |
-
1972
- 1972-05-18 DD DD163067A patent/DD101897A5/xx unknown
- 1972-12-18 CS CS7200008728A patent/CS185615B2/cs unknown
- 1972-12-27 PL PL1972159871A patent/PL82166B1/pl unknown
- 1972-12-27 DK DK647572AA patent/DK141100B/da not_active IP Right Cessation
- 1972-12-27 ES ES410069A patent/ES410069A1/es not_active Expired
- 1972-12-28 HU HUTO895A patent/HU169409B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU169409B (enrdf_load_html_response) | 1976-11-28 |
| ES410069A1 (es) | 1976-05-01 |
| DK141100C (enrdf_load_html_response) | 1980-06-16 |
| CS185615B2 (en) | 1978-10-31 |
| DD101897A5 (enrdf_load_html_response) | 1973-11-20 |
| PL82166B1 (enrdf_load_html_response) | 1975-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO157933B (no) | Analogifremgangsmaate for fremstilling av terapeutisk virksomme cefemforbindelser. | |
| US3864340A (en) | Process for producing 7-aclamida-3-cephem-4-carboxylic acids | |
| US4012382A (en) | α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives | |
| JP2004520336A (ja) | 新規チアゾリル酢酸チオエステル誘導体およびそれらのセファロスポリン化合物製造のための使用 | |
| US7405294B2 (en) | Intermediate cefdinir salts | |
| JPH09512259A (ja) | セファロスポリン合成 | |
| GB2105335A (en) | Cephalosporin quinolinium betaines | |
| JPH01230547A (ja) | ３−オキソ酪酸第三ブチルの製造法及びその用途 | |
| US5387679A (en) | Process for the preparation of cephalosporins intermediates | |
| CA2326441C (en) | Process for purification of a cephalosporin derivative | |
| JPS6337112B2 (enrdf_load_html_response) | ||
| JPH0553798B2 (enrdf_load_html_response) | ||
| JPH04225985A (ja) | セフアロスポリン化合物 | |
| HU213267B (en) | Process for producing stereospecific cefepime-dihydrochloride-hydrate at ph 5-7,5 | |
| DK141100B (da) | Fremgangsmåde til fremstilling af 7-acylamido-3-cephem-4-carboxylsyrer. | |
| NO169231B (no) | Fremgangsmaate ved fremstilling av karboksylsyreamider. | |
| US4092476A (en) | Phthalidyl esters of 7-[(α amino, 2 substituted acetamido)-3-(heterocyclic-thio methyl)]cephalosporins | |
| EP0791597B1 (en) | Method for manufacture of cephalosporins and intermediates thereof | |
| US4338436A (en) | 7-[2-[(Substituted benzoyl)amino]acetamido]cephalosporins | |
| JPS62103092A (ja) | β−ラクタム誘導体 | |
| US3840532A (en) | Process for cleaving cephalosporin compounds | |
| US4237280A (en) | Intermediate for cephalosporin type compound | |
| KR0129567B1 (ko) | 반응성 유기산 유도체로부터 세팔로스포린 화합물의 제조방법 | |
| US4338439A (en) | 7-[2-[(Substituted benzoyl]amino]acetamido]cephalosporins | |
| DK142418B (da) | Fremgangsmåde til fremstilling af 6-acylamidopenicillin- eller 7-acylamidocephalosporin-forbindelser. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |