NO800828L - Fremgangsmaate ved fremstilling av cefalosporinantibiotika - Google Patents
Fremgangsmaate ved fremstilling av cefalosporinantibiotikaInfo
- Publication number
- NO800828L NO800828L NO800828A NO800828A NO800828L NO 800828 L NO800828 L NO 800828L NO 800828 A NO800828 A NO 800828A NO 800828 A NO800828 A NO 800828A NO 800828 L NO800828 L NO 800828L
- Authority
- NO
- Norway
- Prior art keywords
- group
- formula
- compound
- compounds
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 229940124587 cephalosporin Drugs 0.000 title claims description 20
- 229930186147 Cephalosporin Natural products 0.000 title claims description 19
- 239000003242 anti bacterial agent Substances 0.000 title claims description 17
- 229940088710 antibiotic agent Drugs 0.000 title claims description 15
- 150000001780 cephalosporins Chemical class 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 129
- -1 N-carbamoylmethylpyridin-4-yl group Chemical group 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 231100000252 nontoxic Toxicity 0.000 claims description 20
- 230000003000 nontoxic effect Effects 0.000 claims description 20
- 230000003115 biocidal effect Effects 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000012038 nucleophile Substances 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UFPAOYBOQZUDFO-UHFFFAOYSA-N 2-(2h-pyridin-1-yl)acetamide Chemical group NC(=O)CN1CC=CC=C1 UFPAOYBOQZUDFO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 229910001868 water Inorganic materials 0.000 description 35
- 239000007787 solid Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 150000007513 acids Chemical class 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 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 description 13
- 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
- 239000006260 foam Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000005917 acylation reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 7
- 230000010933 acylation Effects 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- BLTIWAWCPGEDCR-UHFFFAOYSA-N 2-(4-sulfanylidenepyridin-1-yl)acetamide Chemical compound NC(=O)CN1C=CC(=S)C=C1 BLTIWAWCPGEDCR-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 239000012346 acetyl chloride Substances 0.000 description 5
- 229940126575 aminoglycoside Drugs 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 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 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
- 235000010262 sodium metabisulphite Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
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- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 229940001584 sodium metabisulfite Drugs 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
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- 230000009471 action Effects 0.000 description 2
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- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 2
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- 150000002500 ions Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
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- 235000010755 mineral Nutrition 0.000 description 2
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- 229910017604 nitric acid Inorganic materials 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
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- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- AAMCVENDCXWDPJ-UHFFFAOYSA-N sulfanyl acetate Chemical class CC(=O)OS AAMCVENDCXWDPJ-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7910088 | 1979-03-22 | ||
| GB7932982 | 1979-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO800828L true NO800828L (no) | 1980-09-23 |
Family
ID=26270985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO800828A NO800828L (no) | 1979-03-22 | 1980-03-21 | Fremgangsmaate ved fremstilling av cefalosporinantibiotika |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4315005A (xx) |
| CA (1) | CA1144920A (xx) |
| CH (1) | CH651574A5 (xx) |
| DE (1) | DE3011038A1 (xx) |
| DK (1) | DK123480A (xx) |
| ES (3) | ES489781A0 (xx) |
| FI (1) | FI800889A (xx) |
| FR (1) | FR2451921A1 (xx) |
| IE (1) | IE49569B1 (xx) |
| IL (1) | IL59680A (xx) |
| IT (1) | IT1143081B (xx) |
| LU (1) | LU82285A1 (xx) |
| NL (1) | NL8001673A (xx) |
| NO (1) | NO800828L (xx) |
| NZ (1) | NZ193212A (xx) |
| PH (1) | PH15777A (xx) |
| PT (3) | PT70995B (xx) |
| SE (1) | SE8002217L (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR231986A1 (es) * | 1978-05-26 | 1985-04-30 | Glaxo Group Ltd | Procedimiento para preparar antibioticos de cefalosporina |
| IT1207008B (it) * | 1978-11-17 | 1989-05-17 | Glaxo Group Ltd | Antibiotici cefalosporinici composizioni che li contengono e procedimenti per produrli |
| US4443444A (en) * | 1980-08-11 | 1984-04-17 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| GR75487B (xx) * | 1981-06-22 | 1984-07-23 | Fujisawa Pharmaceutical Co | |
| FR2516515A1 (fr) * | 1981-11-16 | 1983-05-20 | Sanofi Sa | Nouveaux derives de pyridinium thiomethyl cephalosporines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2517309A1 (fr) * | 1981-12-01 | 1983-06-03 | Sanofi Sa | Nouveaux derives de cephalosporines substitues en position 3 par un groupe heterocycle thiomethyl; procede de preparation desdits composes et compositions pharmaceutiques en contenant |
| US4616081A (en) * | 1982-07-07 | 1986-10-07 | Asahi Kasei Kogyo Kabushiki Kaisha | Cephalosporin compounds |
| WO1997022611A1 (en) * | 1995-12-20 | 1997-06-26 | Bristol-Myers Squibb Company | Cephalosporin derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4033950A (en) * | 1971-05-14 | 1977-07-05 | Glaxo Laboratories Limited | 3-Hydroxymethyl-7β-(2-alkoxy-or benzyloxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof |
| US4144393A (en) * | 1973-12-21 | 1979-03-13 | Glaxo Laboratories Limited | 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group |
| US4144392A (en) * | 1973-12-21 | 1979-03-13 | Glaxo Laboratories Limited | Cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyimino-arylacetamido group and at position-3 the residue of a sulphur nucleophile |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| US4166115A (en) * | 1976-04-12 | 1979-08-28 | Fujisawa Pharmaceutical Co., Ltd. | Syn 7-oxoimino substituted derivatives of cephalosporanic acid |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
-
1980
- 1980-03-21 FI FI800889A patent/FI800889A/fi not_active Application Discontinuation
- 1980-03-21 DK DK123480A patent/DK123480A/da not_active IP Right Cessation
- 1980-03-21 IT IT48230/80A patent/IT1143081B/it active
- 1980-03-21 ES ES489781A patent/ES489781A0/es active Granted
- 1980-03-21 PT PT70995A patent/PT70995B/pt unknown
- 1980-03-21 PH PH23792A patent/PH15777A/en unknown
- 1980-03-21 DE DE19803011038 patent/DE3011038A1/de not_active Withdrawn
- 1980-03-21 IL IL59680A patent/IL59680A/xx unknown
- 1980-03-21 PT PT70996A patent/PT70996B/pt unknown
- 1980-03-21 IE IE593/80A patent/IE49569B1/en unknown
- 1980-03-21 NZ NZ193212A patent/NZ193212A/xx unknown
- 1980-03-21 NL NL8001673A patent/NL8001673A/nl not_active Application Discontinuation
- 1980-03-21 ES ES489782A patent/ES8103757A1/es not_active Expired
- 1980-03-21 CH CH2257/80A patent/CH651574A5/de not_active IP Right Cessation
- 1980-03-21 LU LU82285A patent/LU82285A1/fr unknown
- 1980-03-21 ES ES489783A patent/ES8103105A1/es not_active Expired
- 1980-03-21 PT PT70994A patent/PT70994B/pt unknown
- 1980-03-21 US US06/132,644 patent/US4315005A/en not_active Expired - Lifetime
- 1980-03-21 SE SE8002217A patent/SE8002217L/xx not_active Application Discontinuation
- 1980-03-21 NO NO800828A patent/NO800828L/no unknown
- 1980-03-24 FR FR8006473A patent/FR2451921A1/fr active Granted
- 1980-03-24 CA CA000348258A patent/CA1144920A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE8002217L (sv) | 1980-10-31 |
| IL59680A0 (en) | 1980-06-30 |
| IE49569B1 (en) | 1985-10-30 |
| CA1144920A (en) | 1983-04-19 |
| NZ193212A (en) | 1982-12-07 |
| IE800593L (en) | 1980-09-22 |
| IL59680A (en) | 1983-07-31 |
| DE3011038A1 (de) | 1980-11-27 |
| PT70994B (en) | 1982-11-22 |
| US4315005A (en) | 1982-02-09 |
| CH651574A5 (de) | 1985-09-30 |
| ES489782A0 (es) | 1981-03-16 |
| ES8103757A1 (es) | 1981-03-16 |
| FR2451921B1 (xx) | 1984-04-27 |
| PT70995B (en) | 1981-06-25 |
| ES8103101A1 (es) | 1981-02-16 |
| LU82285A1 (fr) | 1980-10-08 |
| PT70994A (en) | 1980-04-01 |
| PH15777A (en) | 1983-03-24 |
| PT70996B (en) | 1981-06-25 |
| ES489783A0 (es) | 1981-02-16 |
| NL8001673A (nl) | 1980-09-24 |
| FI800889A (fi) | 1980-09-23 |
| ES489781A0 (es) | 1981-02-16 |
| ES8103105A1 (es) | 1981-02-16 |
| PT70995A (en) | 1980-04-01 |
| IT1143081B (it) | 1986-10-22 |
| PT70996A (en) | 1980-04-01 |
| DK123480A (da) | 1980-09-23 |
| FR2451921A1 (fr) | 1980-10-17 |
| IT8048230A0 (it) | 1980-03-21 |
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