NO800828L - Fremgangsmaate ved fremstilling av cefalosporinantibiotika - Google Patents

Fremgangsmaate ved fremstilling av cefalosporinantibiotika

Info

Publication number: NO800828L
Authority: NO; Norway
Prior art keywords: group; formula; compound; compounds; acid
Prior art date: 1979-03-22

Application number

NO800828A

Other languages

English (en)

Norwegian (no)

Inventor

Barry Edward Ayres

Niall Galbraith Weir

Original Assignee

Glaxo Group Ltd

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.)

1979-03-22

Filing date

1980-03-21

Publication date

1980-09-23

1980-03-21 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1980-09-23 Publication of NO800828L publication Critical patent/NO800828L/no

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
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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
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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
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241000589516 Pseudomonas Species 0.000 description 3
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
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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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239000003960 organic solvent Substances 0.000 description 3
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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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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
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
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RRNJROHIFSLGRA-JEDNCBNOSA-N acetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.NCCCC[C@H](N)C(O)=O RRNJROHIFSLGRA-JEDNCBNOSA-N 0.000 description 2
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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239000000543 intermediate Substances 0.000 description 2
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CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 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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GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
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239000000829 suppository Substances 0.000 description 2
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ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
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
229960004919 procaine Drugs 0.000 description 1
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239000003586 protic polar solvent Substances 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
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
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
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229940115939 shigella sonnei Drugs 0.000 description 1
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SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
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JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
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238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
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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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
125000005490 tosylate group Chemical group 0.000 description 1
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 1
238000005866 tritylation reaction Methods 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

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)

NO800828A 1979-03-22 1980-03-21 Fremgangsmaate ved fremstilling av cefalosporinantibiotika NO800828L (no)

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)	ES8103105A1 (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)	PT70996B (xx)
SE (1)	SE8002217L (xx)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
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
ZA796195B (en) *	1978-11-17	1980-11-26	Glaxo Group Ltd	Cephalosporin antibiotics
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
US5734047A (en) *	1995-12-20	1998-03-31	Bristol-Myers Squibb Company	Cephalosporin derivatives

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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
US4095021A (en) *	1973-12-21	1978-06-13	Glaxo Laboratories Limited	3-Carbamoyloxymethyl or N-methyl-carbamoyloxymethyl-7-[2-carboxymethoxyimino-2-(fur-2-yl or thien-2-yl)acetamido]ceph-3-em-4-carboxylic acids and derivatives thereof
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 US US06/132,644 patent/US4315005A/en not_active Expired - Lifetime
- 1980-03-21 DK DK123480A patent/DK123480A/da not_active IP Right Cessation
- 1980-03-21 ES ES489783A patent/ES8103105A1/es not_active Expired
- 1980-03-21 IL IL59680A patent/IL59680A/xx unknown
- 1980-03-21 PT PT70996A patent/PT70996B/pt unknown
- 1980-03-21 PT PT70995A patent/PT70995B/pt unknown
- 1980-03-21 ES ES489782A patent/ES489782A0/es active Granted
- 1980-03-21 LU LU82285A patent/LU82285A1/fr unknown
- 1980-03-21 FI FI800889A patent/FI800889A/fi not_active Application Discontinuation
- 1980-03-21 ES ES489781A patent/ES489781A0/es active Granted
- 1980-03-21 SE SE8002217A patent/SE8002217L/xx not_active Application Discontinuation
- 1980-03-21 NO NO800828A patent/NO800828L/no unknown
- 1980-03-21 NL NL8001673A patent/NL8001673A/nl not_active Application Discontinuation
- 1980-03-21 PH PH23792A patent/PH15777A/en unknown
- 1980-03-21 IE IE593/80A patent/IE49569B1/en unknown
- 1980-03-21 NZ NZ193212A patent/NZ193212A/xx unknown
- 1980-03-21 PT PT70994A patent/PT70994B/pt unknown
- 1980-03-21 CH CH2257/80A patent/CH651574A5/de not_active IP Right Cessation
- 1980-03-21 DE DE19803011038 patent/DE3011038A1/de not_active Withdrawn
- 1980-03-21 IT IT48230/80A patent/IT1143081B/it active
- 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
NZ193212A (en)	1982-12-07
IL59680A0 (en)	1980-06-30
SE8002217L (sv)	1980-10-31
ES8103757A1 (es)	1981-03-16
IE800593L (en)	1980-09-22
FI800889A (fi)	1980-09-23
ES489782A0 (es)	1981-03-16
PT70994B (en)	1982-11-22
DK123480A (da)	1980-09-23
FR2451921A1 (fr)	1980-10-17
NL8001673A (nl)	1980-09-24
CA1144920A (en)	1983-04-19
PT70995A (en)	1980-04-01
PT70995B (en)	1981-06-25
LU82285A1 (fr)	1980-10-08
ES489783A0 (es)	1981-02-16
IT1143081B (it)	1986-10-22
IL59680A (en)	1983-07-31
PT70996A (en)	1980-04-01
ES8103101A1 (es)	1981-02-16
US4315005A (en)	1982-02-09
IE49569B1 (en)	1985-10-30
DE3011038A1 (de)	1980-11-27
FR2451921B1 (xx)	1984-04-27
PT70996B (en)	1981-06-25
ES8103105A1 (es)	1981-02-16
IT8048230A0 (it)	1980-03-21
PT70994A (en)	1980-04-01
CH651574A5 (de)	1985-09-30
ES489781A0 (es)	1981-02-16
PH15777A (en)	1983-03-24

Publication	Publication Date	Title
US4258041A (en)	1981-03-24	(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-pyridiniummethyl)-ceph-3-em-4-carboxylate and salts thereof
KR830000835B1 (ko)	1983-04-20	세팔로스포린 항생제의 제조방법
US4621081A (en)	1986-11-04	Cephalosporin antibiotics
US4464368A (en)	1984-08-07	Cephalosporin antibiotics
NO800828L (no)	1980-09-23	Fremgangsmaate ved fremstilling av cefalosporinantibiotika
GB2036724A (en)	1980-07-02	Cephalosporin compounds
CA1144156A (en)	1983-04-05	Cephalosporin antibiotics
US4504477A (en)	1985-03-12	Cephalosporin antibiotics
KR830001130B1 (ko)	1983-06-14	세팔로스포린 항생제의 제조방법
GB2046261A (en)	1980-11-12	Cephalosporin antibiotics
US4200746A (en)	1980-04-29	Cephalosporins
GB2036738A (en)	1980-07-02	Cephalosporin antibiotics
IE49099B1 (en)	1985-07-24	Cephalosporin compounds
GB2037281A (en)	1980-07-09	7-( alpha -(2-amino.4-thiazolyl)- alpha - hydroximino-acetamido)- cephalosporins
GB2027691A (en)	1980-02-27	Cephalosporin Antibiotics
GB2177691A (en)	1987-01-28	Cephalosporin antibiotics
NO832376L (no)	1984-01-02	Cephalosporin-antibiotika.
CA1129408A (en)	1982-08-10	Cephalosporin antibiotics
KR830001593B1 (ko)	1983-08-16	세팔로스포린 항생제의 제조방법
EP0095329A2 (en)	1983-11-30	Cephalosporin antibiotics
GB2062624A (en)	1981-05-28	Cephalosporin Antibiotics
GB2123415A (en)	1984-02-01	Cephalosporin antibiotics