DK141502B - Fremgangsmåde til fremstilling af en 7-acylamido-3-methyl-3-cephem-4-carboxylsyreester. - Google Patents

Fremgangsmåde til fremstilling af en 7-acylamido-3-methyl-3-cephem-4-carboxylsyreester. Download PDF

Info

Publication number: DK141502B
Authority: DK; Denmark
Prior art keywords: ester; product; methyl; acid; carboxylic acid
Prior art date: 1974-12-13

Application number

DK556475AA

Other languages

Danish (da)

English (en)

Other versions

DK141502C (nl

DK556475A (nl

Inventor

Lowell Deloss Hatfield

Original Assignee

Lilly Co Eli

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-12-13

Filing date

1975-12-09

Publication date

1980-03-31

1975-12-09 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1976-06-14 Publication of DK556475A publication Critical patent/DK556475A/da

1980-03-31 Publication of DK141502B publication Critical patent/DK141502B/da

1980-09-22 Application granted granted Critical

1980-09-22 Publication of DK141502C publication Critical patent/DK141502C/da

Links

239000002253 acid Substances 0.000 title description 21
238000004519 manufacturing process Methods 0.000 title description 4
-1 sulfoxide ester Chemical class 0.000 description 44
238000000034 method Methods 0.000 description 43
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 34
239000002904 solvent Substances 0.000 description 27
150000002148 esters Chemical class 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
229930182555 Penicillin Natural products 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 11
230000003115 biocidal effect Effects 0.000 description 11
238000009835 boiling Methods 0.000 description 11
229940049954 penicillin Drugs 0.000 description 11
238000006049 ring expansion reaction Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 9
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 8
229940106164 cephalexin Drugs 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
XJMFIMBSWLGRQW-UHFFFAOYSA-N P(O)(O)=O.ClCCl Chemical compound P(O)(O)=O.ClCCl XJMFIMBSWLGRQW-UHFFFAOYSA-N 0.000 description 7
ZYDCYYCORHLHDQ-UHFFFAOYSA-N P([O-])([O-])=O.ClCCl.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1 Chemical compound P([O-])([O-])=O.ClCCl.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1 ZYDCYYCORHLHDQ-UHFFFAOYSA-N 0.000 description 7
125000004185 ester group Chemical group 0.000 description 7
239000000203 mixture Substances 0.000 description 7
150000002960 penicillins Chemical class 0.000 description 7
230000008707 rearrangement Effects 0.000 description 7
239000007858 starting material Substances 0.000 description 7
150000003462 sulfoxides Chemical class 0.000 description 7
229930186147 Cephalosporin Natural products 0.000 description 6
229940124587 cephalosporin Drugs 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000003377 acid catalyst Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
150000001780 cephalosporins Chemical class 0.000 description 4
229940075894 denatured ethanol Drugs 0.000 description 4
NNQIJOYQWYKBOW-UHFFFAOYSA-N desacetoxycephalosphorin G Natural products S1CC(C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 NNQIJOYQWYKBOW-UHFFFAOYSA-N 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
230000007017 scission Effects 0.000 description 4
DYSKJEHQMVZZTP-FQNRMIAFSA-N 2,2,2-trichloroethyl (6r)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(=O)OCC(Cl)(Cl)Cl)NC(=O)CC1=CC=CC=C1 DYSKJEHQMVZZTP-FQNRMIAFSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IQTYUGSHUITLHX-UHFFFAOYSA-N P([O-])(O)=O.ClCCl.[NH+]1=CC=CC=C1 Chemical compound P([O-])(O)=O.ClCCl.[NH+]1=CC=CC=C1 IQTYUGSHUITLHX-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 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
229940056360 penicillin g Drugs 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000006462 rearrangement reaction Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
150000003860 tertiary carboxamides Chemical class 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
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
DNPOVSLJNLLGMA-SJUANORRSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)COC1=CC=CC=C1 DNPOVSLJNLLGMA-SJUANORRSA-N 0.000 description 1
IWAAXRFPRHQKAZ-RKOYOZNISA-N (6R)-3-methyl-4-[(4-nitrophenyl)methyl]-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound [N+](=O)([O-])C1=CC=C(CC2S[C@H]3N(C(=C2C)C(=O)O)C(C3NC(COC3=CC=CC=C3)=O)=O)C=C1 IWAAXRFPRHQKAZ-RKOYOZNISA-N 0.000 description 1
LFMBIMXJWIQULB-SSDOTTSWSA-N (6r)-3-methyl-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC(C)=CN2C(=O)C[C@H]21 LFMBIMXJWIQULB-SSDOTTSWSA-N 0.000 description 1
RKPYPVYWRWYHKC-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)COC1=CC=CC=C1 RKPYPVYWRWYHKC-WPZCJLIBSA-N 0.000 description 1
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 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 1
125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
STHDVBYGYGGFLQ-UHFFFAOYSA-N 2-(4-nitrophenyl)-3-phenylpropanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C(=O)N)CC1=CC=CC=C1 STHDVBYGYGGFLQ-UHFFFAOYSA-N 0.000 description 1
NWWJFMCCTZLKNT-UHFFFAOYSA-N 3,4-dihydro-2h-thiazine Chemical group C1CC=CSN1 NWWJFMCCTZLKNT-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001602880 Delos Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
125000006244 carboxylic acid protecting group Chemical group 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
IXTGXVWLIBNABC-UHFFFAOYSA-N dichloromethylphosphonic acid Chemical compound OP(O)(=O)C(Cl)Cl IXTGXVWLIBNABC-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
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 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000005179 haloacetyl group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004687 hexahydrates Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
150000005331 phenylglycines Chemical class 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
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005303 weighing Methods 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Cephalosporin Compounds (AREA)

DK556475AA 1974-12-13 1975-12-09 Fremgangsmåde til fremstilling af en 7-acylamido-3-methyl-3-cephem-4-carboxylsyreester. DK141502B (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/532,536 US3953440A (en)	1974-12-13	1974-12-13	Deacetoxycephalosporins via penicillin sulfoxide rearrangement
US53253674		1974-12-13

Publications (3)

Publication Number	Publication Date
DK556475A DK556475A (nl)	1976-06-14
DK141502B true DK141502B (da)	1980-03-31
DK141502C DK141502C (nl)	1980-09-22

Family

ID=24122205

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK556475AA DK141502B (da)	1974-12-13	1975-12-09	Fremgangsmåde til fremstilling af en 7-acylamido-3-methyl-3-cephem-4-carboxylsyreester.

Country Status (26)

Country	Link
US (1)	US3953440A (nl)
JP (1)	JPS5532715B2 (nl)
AR (1)	AR208576A1 (nl)
AT (1)	AT344893B (nl)
BE (1)	BE836414A (nl)
BG (1)	BG26393A3 (nl)
CA (1)	CA1053225A (nl)
CH (1)	CH601308A5 (nl)
CS (1)	CS203983B2 (nl)
DD (1)	DD123753A5 (nl)
DE (1)	DE2555183C3 (nl)
DK (1)	DK141502B (nl)
ES (1)	ES443462A1 (nl)
FR (1)	FR2294178A1 (nl)
GB (1)	GB1535341A (nl)
GR (1)	GR59923B (nl)
HU (1)	HU173324B (nl)
IE (1)	IE42380B1 (nl)
IL (1)	IL48602A (nl)
NL (1)	NL175623C (nl)
PH (1)	PH13532A (nl)
PL (1)	PL105054B1 (nl)
RO (1)	RO68208A (nl)
SE (1)	SE426829B (nl)
YU (1)	YU304675A (nl)
ZA (1)	ZA757743B (nl)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1465893A (en) *	1973-02-09	1977-03-02	Gist Brocades Nv	I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use
ES431585A1 (es) *	1974-11-02	1976-11-16	Gema Sa	Procedimiento para la transformacion de acido 6-aminopeni- cilanico en 7-amino-desacetoxicefalosporanico.
US20060201522A1 (en) *	2005-03-10	2006-09-14	Yoshiaki Sato	Method for lowering blood glucose levels, method of treating diabetes, and method of prevention of diabetes
CN102432627A (zh) *	2011-09-19	2012-05-02	江苏九九久科技股份有限公司	生产对硝基苄基青霉素g亚砜酯的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3819622A (en) *	1969-03-11	1974-06-25	Glaxo Lab Ltd	Method of producing 7beta-acylamido-3-methylceph-3-em-4-carboxylic acid esters
HU167757B (nl) *	1969-03-11	1975-12-25
GB1312233A (en) *	1969-12-05	1973-04-04	Glaxo Lab Ltd	Cephalosporin compounds
US3843637A (en) *	1971-05-11	1974-10-22	Bristol Myers Co	Process for rearranging 6-acylamidopenicillanic acid-1-oxides to 7-acyla mido-3-methyl-ceph-3-em-4-carboxylic acids
JPS4844296A (nl) *	1971-10-14	1973-06-26
NL7303263A (nl) *	1972-03-09	1973-09-11
JPS536158B2 (nl) *	1972-03-23	1978-03-04
JPS4943999A (nl) *	1972-09-01	1974-04-25

1974
- 1974-12-13 US US05/532,536 patent/US3953440A/en not_active Expired - Lifetime
1975
- 1975-12-03 CA CA241,008A patent/CA1053225A/en not_active Expired
- 1975-12-03 YU YU03046/75A patent/YU304675A/xx unknown
- 1975-12-03 IL IL48602A patent/IL48602A/xx unknown
- 1975-12-03 GR GR49523A patent/GR59923B/el unknown
- 1975-12-04 SE SE7513702A patent/SE426829B/xx not_active IP Right Cessation
- 1975-12-05 PH PH17835A patent/PH13532A/en unknown
- 1975-12-05 AR AR261513A patent/AR208576A1/es active
- 1975-12-08 NL NLAANVRAGE7514296,A patent/NL175623C/nl not_active IP Right Cessation
- 1975-12-08 DE DE2555183A patent/DE2555183C3/de not_active Expired
- 1975-12-09 GB GB50354/75A patent/GB1535341A/en not_active Expired
- 1975-12-09 JP JP14681975A patent/JPS5532715B2/ja not_active Expired
- 1975-12-09 DK DK556475AA patent/DK141502B/da not_active IP Right Cessation
- 1975-12-09 BE BE1007067A patent/BE836414A/xx not_active IP Right Cessation
- 1975-12-10 RO RO7584155A patent/RO68208A/ro unknown
- 1975-12-10 ZA ZA757743A patent/ZA757743B/xx unknown
- 1975-12-10 FR FR7537770A patent/FR2294178A1/fr active Granted
- 1975-12-11 HU HU75EI659A patent/HU173324B/hu unknown
- 1975-12-11 BG BG7531760A patent/BG26393A3/xx unknown
- 1975-12-11 IE IE2703/75A patent/IE42380B1/en unknown
- 1975-12-11 AT AT940875A patent/AT344893B/de not_active IP Right Cessation
- 1975-12-12 CS CS758486A patent/CS203983B2/cs unknown
- 1975-12-12 DD DD190104A patent/DD123753A5/xx unknown
- 1975-12-12 PL PL1975185465A patent/PL105054B1/pl unknown
- 1975-12-12 CH CH1616375A patent/CH601308A5/xx not_active IP Right Cessation
- 1975-12-12 ES ES443462A patent/ES443462A1/es not_active Expired

Also Published As

Publication number	Publication date
FR2294178A1 (fr)	1976-07-09
JPS5532715B2 (nl)	1980-08-26
FR2294178B1 (nl)	1979-10-19
NL7514296A (nl)	1976-06-15
AU8730175A (en)	1977-06-09
DK141502C (nl)	1980-09-22
IL48602A (en)	1979-03-12
NL175623B (nl)	1984-07-02
IL48602A0 (en)	1976-02-29
DE2555183C3 (de)	1981-10-29
HU173324B (hu)	1979-04-28
AR208576A1 (es)	1977-02-15
SE7513702L (sv)	1976-06-14
AT344893B (de)	1978-08-10
CS203983B2 (en)	1981-03-31
IE42380B1 (en)	1980-07-30
NL175623C (nl)	1984-12-03
BE836414A (fr)	1976-06-09
DE2555183B2 (de)	1980-09-11
DK556475A (nl)	1976-06-14
PL105054B1 (pl)	1979-09-29
DE2555183A1 (de)	1976-06-16
GR59923B (en)	1978-03-20
SE426829B (sv)	1983-02-14
PH13532A (en)	1980-06-19
DD123753A5 (nl)	1977-01-12
BG26393A3 (nl)	1979-03-15
CA1053225A (en)	1979-04-24
ZA757743B (en)	1977-07-27
ATA940875A (de)	1977-12-15
GB1535341A (en)	1978-12-13
JPS5182293A (nl)	1976-07-19
RO68208A (ro)	1980-08-15
CH601308A5 (nl)	1978-07-14
YU304675A (en)	1982-05-31
ES443462A1 (es)	1977-08-16
IE42380L (en)	1976-06-13
US3953440A (en)	1976-04-27

Legal Events

Date	Code	Title	Description
1996-01-22	PUP	Patent expired

Publication	Publication Date	Title
SU841588A3 (ru)	1981-06-23	Способ получени -окси- - - бЕНзОТиАзиН- -КАРбОКСАМид- -диОК-СидОВ или иХ СОлЕй C НЕОРгАНи-чЕСКиМи или ОРгАНичЕСКиМи OCHO-ВАНи Ми
JP5247436B2 (ja)	2013-07-24	メチレンジスルホネート化合物の製造方法
JPS5834474B2 (ja)	1983-07-27	チアゾリジン誘導体の製造法
SU662013A3 (ru)	1979-05-05	Способ получени гетацефалексина или его солей
CS228520B2 (en)	1984-05-14	Method for the production of 4-hydroxy-2-methyl-n-2-pyridyl-2h-1,2-benzothiazin-3-carboxamid-1,1-dioxide
DK141502B (da)	1980-03-31	Fremgangsmåde til fremstilling af en 7-acylamido-3-methyl-3-cephem-4-carboxylsyreester.
US3976641A (en)	1976-08-24	Cephalosporin intermediates and process therefor
JP2003513983A (ja)	2003-04-15	高純度セフポドキシムプロキセチルの製造方法
SU797579A3 (ru)	1981-01-15	Способ получени амидов кислот или ихСОлЕй C щЕлОчНыМи МЕТАллАМи или ТРиАл-КилАМиНАМи
SU1245262A3 (ru)	1986-07-15	Способ получени сложного 1-этоксикарбонилоксиэтилового эфира 6- @ -(-)-2-амино-2-фенилацетамидо @ пенициллановой кислоты в виде его аддитивной соли с галоидводородной кислотой
CA1236089A (en)	1988-05-03	Ceftazidime
RU2248347C2 (ru)	2005-03-20	Способ получения ацилированных 1,3-дикарбонильных соединений
US3966720A (en)	1976-06-29	Process for producing desacetoxy cephalosporanic acid compound
KR790001071B1 (ko)	1979-08-24	페니실린 설폭사이드를 전위시켜서 테아세톡시 세팔로스포린을 제조하는 방법
PL85296B1 (en)	1976-04-30	Production of antibacterial agents[gb1314758a]
PL171318B1 (en)	1997-04-30	Method of obtaining benzo[b]naphtyridines
EP0163506B1 (en)	1989-11-02	Process for the preparation of a pyridil-propanoic acid
KR810000290B1 (ko)	1981-03-30	3, 4-디하이드로-2-메틸-4-옥소-2h-1, 2-벤조티아진-3-카복실산-1, 1-디옥사이드의 제조방법
JPS6251959B2 (nl)	1987-11-02
HU186568B (en)	1985-08-28	Process for producing 4-methyl-5-oxo-3-thioxo-tetrahydro-1,2,4-bracket-2h,4h-bracket closed-triazines
US4231954A (en)	1980-11-04	Dane salt and process for preparing aminopenicillins therefrom
JPS6127396B2 (nl)	1986-06-25
KR100412334B1 (ko)	2003-12-31	4-치환된-1ｈ-피롤-3-카복실산 에스테르의 새로운 제조방법
EP0217376A2 (en)	1987-04-08	Process for preparing optically active alpha-haloalkyl-arylketones
US3372158A (en)	1968-03-05	Process for the preparation of penicillins