NL8002049A - Gefalosporinen en een werkwijze ter bereiding ervan. - Google Patents

Gefalosporinen en een werkwijze ter bereiding ervan. Download PDF

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Publication number: NL8002049A
Authority: NL; Netherlands
Prior art keywords: carbon atoms; small number; group; substituted; alkyl
Prior art date: 1979-04-09

Application number

NL8002049A

Other languages

English (en)

Dutch (nl)

Original Assignee

Novo Industri As

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.)

1979-04-09

Filing date

1980-04-08

Publication date

1980-10-13

1980-04-08 Application filed by Novo Industri As filed Critical Novo Industri As

1980-10-13 Publication of NL8002049A publication Critical patent/NL8002049A/nl

Links

238000000034 method Methods 0.000 title claims description 49
-1 carbamoyloxy Chemical group 0.000 claims description 150
125000004432 carbon atom Chemical group C* 0.000 claims description 93
150000001875 compounds Chemical class 0.000 claims description 86
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 22
150000004677 hydrates Chemical class 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 16
125000003710 aryl alkyl group Chemical group 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000001768 cations Chemical class 0.000 claims description 10
125000004423 acyloxy group Chemical group 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
125000000547 substituted alkyl group Chemical group 0.000 claims description 9
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
229930186147 Cephalosporin Natural products 0.000 claims description 8
229940124587 cephalosporin Drugs 0.000 claims description 8
150000001780 cephalosporins Chemical class 0.000 claims description 8
230000007062 hydrolysis Effects 0.000 claims description 8
238000006460 hydrolysis reaction Methods 0.000 claims description 8
150000002500 ions Chemical class 0.000 claims description 8
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000004437 phosphorous atom Chemical group 0.000 claims description 7
125000003107 substituted aryl group Chemical group 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
229910052708 sodium Chemical group 0.000 claims description 5
239000011734 sodium Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 3
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
230000000865 phosphorylative effect Effects 0.000 claims description 3
230000003213 activating effect Effects 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
230000007306 turnover Effects 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000000843 powder Substances 0.000 description 27
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
239000003921 oil Substances 0.000 description 13
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
239000002904 solvent Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
125000003368 amide group Chemical group 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012267 brine Substances 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
238000012746 preparative thin layer chromatography Methods 0.000 description 5
238000003756 stirring Methods 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000012043 crude product Substances 0.000 description 4
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910052710 silicon Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
244000005700 microbiome Species 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
208000003383 pontocerebellar hypoplasia type 3 Diseases 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 3
229960004919 procaine Drugs 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000010703 silicon Substances 0.000 description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000588748 Klebsiella Species 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000005530 alkylenedioxy group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000004438 haloalkoxy group Chemical group 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000010410 layer Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-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
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
YNTYMCARTMFYTD-UHFFFAOYSA-N 2-(6-hydroxyiminocyclohexa-2,4-dien-1-yl)acetic acid Chemical compound ON=C1C=CC=CC1CC(O)=O YNTYMCARTMFYTD-UHFFFAOYSA-N 0.000 description 1
RNNIWANKYVVTII-UHFFFAOYSA-N 2-(furan-2-yl)-2-hydroxyiminoacetic acid Chemical compound ON=C(C(O)=O)C1=CC=CO1 RNNIWANKYVVTII-UHFFFAOYSA-N 0.000 description 1
OGZZDSIYAVGWKQ-UHFFFAOYSA-N 2-[6-(2,2-dichloroacetyl)oxyiminocyclohexa-2,4-dien-1-yl]acetic acid Chemical compound OC(=O)CC1C=CC=CC1=NOC(=O)C(Cl)Cl OGZZDSIYAVGWKQ-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
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125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
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125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003376 silicon Chemical class 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
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125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
- 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

Landscapes

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

NL8002049A 1979-04-09 1980-04-08 Gefalosporinen en een werkwijze ter bereiding ervan. NL8002049A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK145579A DK145579A (da)	1979-04-09	1979-04-09	Fremgangsmaade til fremstilling af cephalosporinderivater
DK145579		1979-04-09

Publications (1)

Publication Number	Publication Date
NL8002049A true NL8002049A (nl)	1980-10-13

Family

ID=8105009

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8002049A NL8002049A (nl)	1979-04-09	1980-04-08	Gefalosporinen en een werkwijze ter bereiding ervan.

Country Status (7)

Country	Link
EP (1)	EP0018155A3 (it)
JP (1)	JPS55149295A (it)
DK (1)	DK145579A (it)
FI (1)	FI801110A7 (it)
IT (1)	IT1147347B (it)
NL (1)	NL8002049A (it)
ZA (1)	ZA802105B (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0182633A3 (en) *	1984-11-20	1987-09-02	Ici Pharma	Cephalosporin derivatives
EP0187456A1 (en) *	1984-11-29	1986-07-16	Ici Pharma	Cephalosporin derivatives
GB8626245D0 (en) *	1985-11-27	1986-12-03	Ici Pharma	Cephalosporin compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3870713A (en) *	1970-12-07	1975-03-11	Pfizer	Phosphono substituted alkylcephalosporins
GB1382169A (en) *	1971-02-22	1975-01-29	Squibb & Sons Inc	Alpha-phosphonoacetylcephalosporins
GB1430074A (en) *	1972-07-13	1976-03-31	Beecham Group Ltd	Penicillins
JPS5084591A (it) *	1973-11-29	1975-07-08
JPS5941999B2 (ja) *	1975-07-24	1984-10-11	武田薬品工業株式会社	セフエムまたはベナム化合物の製造法

1979
- 1979-04-09 DK DK145579A patent/DK145579A/da not_active IP Right Cessation
1980
- 1980-04-08 IT IT21237/80A patent/IT1147347B/it active
- 1980-04-08 EP EP80301118A patent/EP0018155A3/en not_active Withdrawn
- 1980-04-08 NL NL8002049A patent/NL8002049A/nl not_active Application Discontinuation
- 1980-04-08 FI FI801110A patent/FI801110A7/fi not_active Application Discontinuation
- 1980-04-09 JP JP4671680A patent/JPS55149295A/ja active Pending
- 1980-04-09 ZA ZA00802105A patent/ZA802105B/xx unknown

Also Published As

Publication number	Publication date
IT8021237A0 (it)	1980-04-08
ZA802105B (en)	1981-04-29
DK145579A (da)	1980-10-10
IT1147347B (it)	1986-11-19
EP0018155A2 (en)	1980-10-29
EP0018155A3 (en)	1981-05-13
FI801110A7 (fi)	1981-01-01
JPS55149295A (en)	1980-11-20

Legal Events

Date	Code	Title	Description
1982-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
JPS5946955B2 (ja)	1984-11-15	抗生物質の新規中間体の製造方法
EP0338372A2 (en)	1989-10-25	Solubilized pro-drugs
GB2124207A (en)	1984-02-15	1-sulfo-2-oxoazetidine derivatives
AU638556B2 (en)	1993-07-01	3-tetrazolylthiomethyl cephalosporin antibiotics
FR2512449A1 (fr)	1983-03-11	Quinoleinium-betaines de cephalosporine et leur application pharmacolique
JPS63146863A (ja)	1988-06-18	カルボン酸類
CS232735B2 (en)	1985-02-14	Method of making cephalosporine derivatives
NZ199168A (en)	1985-08-30	2-oxoazetidine derivatives and pharmaceutical compositions
JPS5857386A (ja)	1983-04-05	セフアロスポリン・イソキノリニウム・ベタイン類
US5329002A (en)	1994-07-12	Antibacterial cephalosporin compounds
US5116827A (en)	1992-05-26	Quinolinecarboxylic acid derivatives as solubilized pro-drugs
US5077282A (en)	1991-12-31	Solubilized pro-drugs
NL8002049A (nl)	1980-10-13	Gefalosporinen en een werkwijze ter bereiding ervan.
EP0209751A2 (en)	1987-01-28	Cephalosporin derivatives and bactericides containing the same
JPS59231090A (ja)	1984-12-25	フルオロメチルチオオキサセフアロスポリン
JPS6016989A (ja)	1985-01-28	オキソ飽和異項環カルボンアミドセフエム化合物
US4239758A (en)	1980-12-16	Cephalosporins
US4057631A (en)	1977-11-08	7-(α-Substituted phenylacetamido)-3-(1-carboxymethylthioethyltetrazolyl-5-thiomethyl)-3-cephem-4-carboxylic acids
US4801703A (en)	1989-01-31	Method for production of cephalosporin compounds
EP0000100B1 (en)	1982-02-03	7-acylamino-3-(1-(2-sulfamoylaminoethyl)-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids, a process for their preparation and compositions containing them
JPS5932472B2 (ja)	1984-08-09	２−アルキル−７−アシルアミノ−２（または３）−セフエム−４−カルボン酸類の製造法
JPH06179675A (ja)	1994-06-28	カルバペネム、該カルバペネムを含有する抗菌作用を有する医薬調剤および該医薬調剤の製造法並びに該医薬調剤を製造するための中間体
EP0249170A2 (en)	1987-12-16	Cephem compounds, their production and use
JPS58128387A (ja)	1983-07-30	新規β−ラクタム化合物およびその製法と用途
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