NO743198L - - Google Patents

Info

Publication number: NO743198L
Authority: NO; Norway
Prior art keywords: group; acid; denotes; compound; methyl
Prior art date: 1973-09-06

Application number

NO743198A

Other languages

English (en)

Norwegian (no)

Inventor

J Bouchaudon

Roy P Le

M N Messer

Original Assignee

Rhone Poulenc Sa

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.)

1973-09-06

Filing date

1974-09-05

Publication date

1975-04-01

1973-09-06 Priority claimed from FR7332150A external-priority patent/FR2243199A1/fr

1974-03-12 Priority claimed from FR7408378A external-priority patent/FR2264020A2/fr

1974-09-05 Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa

1975-04-01 Publication of NO743198L publication Critical patent/NO743198L/no

Links

-1 p-methoxybenzyl group Chemical group 0.000 claims description 67
150000001875 compounds Chemical class 0.000 claims description 50
238000000034 method Methods 0.000 claims description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
229910052783 alkali metal Inorganic materials 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 10
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
239000002609 medium Substances 0.000 claims description 7
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 claims description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 4
125000006000 trichloroethyl group Chemical group 0.000 claims description 4
FPVUWZFFEGYCGB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=NN=C(S)S1 FPVUWZFFEGYCGB-UHFFFAOYSA-N 0.000 claims description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
239000003495 polar organic solvent Substances 0.000 claims 3
238000005903 acid hydrolysis reaction Methods 0.000 claims 2
229960001324 deslanoside Drugs 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 120
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
239000000203 mixture Substances 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 26
239000007787 solid Substances 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 20
238000001914 filtration Methods 0.000 description 19
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
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 17
238000002329 infrared spectrum Methods 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
230000007935 neutral effect Effects 0.000 description 16
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 16
239000000047 product Substances 0.000 description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 15
235000011152 sodium sulphate Nutrition 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
150000001408 amides Chemical class 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
229950005228 bromoform Drugs 0.000 description 13
239000012153 distilled water Substances 0.000 description 11
238000001035 drying Methods 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
230000003287 optical effect Effects 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
235000012239 silicon dioxide Nutrition 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
150000003462 sulfoxides Chemical class 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
229940056360 penicillin g Drugs 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
238000010908 decantation Methods 0.000 description 6
239000005457 ice water Substances 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
150000003952 β-lactams Chemical class 0.000 description 6
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
239000001110 calcium chloride Substances 0.000 description 5
229910001628 calcium chloride Inorganic materials 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
150000002960 penicillins Chemical class 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 4
229930186147 Cephalosporin Natural products 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
229940124587 cephalosporin Drugs 0.000 description 4
150000001780 cephalosporins Chemical class 0.000 description 4
229910001873 dinitrogen Inorganic materials 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
238000006418 Brown reaction Methods 0.000 description 3
241001070941 Castanea Species 0.000 description 3
235000014036 Castanea Nutrition 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000155 melt Substances 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
229940045348 brown mixture Drugs 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
QOXNYNXEVAJYCY-UHFFFAOYSA-N (4-methoxyphenyl)methyl 3-methyl-8-oxo-7-[(2,2,2-trichloroacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)C1=C(C)CSC2N1C(=O)C2NC(=O)C(Cl)(Cl)Cl QOXNYNXEVAJYCY-UHFFFAOYSA-N 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
DYSKJEHQMVZZTP-UHFFFAOYSA-N 2,2,2-trichloroethyl 3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC(C)=C(C(=O)OCC(Cl)(Cl)Cl)N(C2=O)C1C2NC(=O)CC1=CC=CC=C1 DYSKJEHQMVZZTP-UHFFFAOYSA-N 0.000 description 1
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
NVIAYEIXYQCDAN-UHFFFAOYSA-N 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)C12 NVIAYEIXYQCDAN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
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 1
229940106164 cephalexin Drugs 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
229940056367 penicillin v Drugs 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
229960004838 phosphoric acid Drugs 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
YNLZKJXZEZFHDO-UHFFFAOYSA-M potassium;2,2,2-trichloroacetate Chemical compound [K+].[O-]C(=O)C(Cl)(Cl)Cl YNLZKJXZEZFHDO-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
MZKUGCOENXBMFR-UHFFFAOYSA-N pyridin-1-ium;phosphate Chemical compound [O-]P([O-])([O-])=O.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 MZKUGCOENXBMFR-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension 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
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO743198A 1973-09-06 1974-09-05 NO743198L (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7332150A FR2243199A1 (en)	1973-09-06	1973-09-06	7-Trichloroacetamido-3-desacetoxy cephalosporanic acids - inters. for 7-ADCA e.g. by reducing off 7-acyl residue
FR7408378A FR2264020A2 (en)	1974-03-12	1974-03-12	7-Trichloroacetamido-3-desacetoxy cephalosporanic acids - inters. for 7-ADCA e.g. by reducing off 7-acyl residue

Publications (1)

Publication Number	Publication Date
NO743198L true NO743198L (es)	1975-04-01

Family

ID=26217924

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO743198A NO743198L (es)	1973-09-06	1974-09-05
NO750734A NO750734L (es)	1973-09-06	1975-03-05

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO750734A NO750734L (es)	1973-09-06	1975-03-05

Country Status (16)

Country	Link
US (1)	US3975385A (es)
JP (2)	JPS5418278B2 (es)
AR (1)	AR202040A1 (es)
AU (1)	AU464455B2 (es)
DD (1)	DD114416A5 (es)
DE (1)	DE2442661A1 (es)
DK (1)	DK470174A (es)
ES (2)	ES429818A1 (es)
FI (1)	FI261874A (es)
GB (1)	GB1454589A (es)
HU (1)	HU168679B (es)
IL (1)	IL45603A0 (es)
LU (1)	LU70863A1 (es)
NL (1)	NL7411505A (es)
NO (2)	NO743198L (es)
SE (1)	SE7411226L (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK635474A (es) *	1974-02-05	1975-10-13	Ciba Geigy Ag
US4024152A (en) *	1975-09-19	1977-05-17	Eli Lilly And Company	4-Dithio-3-imido-azetidin-2-ones
US4075203A (en) *	1976-06-16	1978-02-21	Eli Lilly And Company	Process for preparing a 3-exomethylenecepham sulfoxide from penicillin sulfoxides
JP3195371B2 (ja) *	1991-03-11	2001-08-06	大塚化学株式会社	セフエム誘導体の製造法
AU2003269416A1 (en) *	2002-11-01	2004-05-25	Orchid Chemicals And Pharmaceuticals Ltd	An improved process for the preparation of chloro methyl cephem derivatives
JP4658806B2 (ja) *	2003-09-09	2011-03-23	日本化学工業株式会社	３−クロロメチル−３−セフェム誘導体の製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1670492A1 (de) *	1966-12-20	1970-03-19	Ciba Geigy	Neue Cephalosporansaeurederivate
US3591585A (en) *	1969-02-14	1971-07-06	Lilly Co Eli	Process for making desacetoxycephalosporins
BE794659A (fr) *	1972-01-28	1973-07-30	Glaxo Lab Ltd	Procede de preparation de composes intermediaires pour l'obtention d'antibiotiques de type beta-lactame

1974
- 1974-08-29 NL NL7411505A patent/NL7411505A/xx not_active Application Discontinuation
- 1974-09-04 DD DD180905A patent/DD114416A5/xx unknown
- 1974-09-04 HU HURO796A patent/HU168679B/hu unknown
- 1974-09-05 JP JP10142774A patent/JPS5418278B2/ja not_active Expired
- 1974-09-05 SE SE7411226A patent/SE7411226L/xx unknown
- 1974-09-05 AU AU73025/74A patent/AU464455B2/en not_active Expired
- 1974-09-05 DK DK470174A patent/DK470174A/da unknown
- 1974-09-05 IL IL45603A patent/IL45603A0/xx unknown
- 1974-09-05 US US05/503,274 patent/US3975385A/en not_active Expired - Lifetime
- 1974-09-05 GB GB3888374A patent/GB1454589A/en not_active Expired
- 1974-09-05 LU LU70863A patent/LU70863A1/xx unknown
- 1974-09-05 NO NO743198A patent/NO743198L/no unknown
- 1974-09-06 FI FI2618/74A patent/FI261874A/fi unknown
- 1974-09-06 ES ES429818A patent/ES429818A1/es not_active Expired
- 1974-09-06 AR AR255504A patent/AR202040A1/es active
- 1974-09-06 DE DE2442661A patent/DE2442661A1/de active Pending
- 1974-10-23 ES ES431287A patent/ES431287A1/es not_active Expired
1975
- 1975-03-05 NO NO750734A patent/NO750734L/no unknown
1977
- 1977-12-09 JP JP14727577A patent/JPS5390288A/ja active Pending

Also Published As

Publication number	Publication date
HU168679B (es)	1976-06-28
JPS5052085A (es)	1975-05-09
US3975385A (en)	1976-08-17
NO750734L (es)	1975-04-14
SE7411226L (es)	1975-03-07
DE2442661A1 (de)	1975-03-27
GB1454589A (en)	1976-11-03
LU70863A1 (es)	1975-05-28
IL45603A0 (en)	1974-11-29
NL7411505A (nl)	1975-03-10
FI261874A (es)	1975-03-07
DK470174A (es)	1975-05-05
JPS5390288A (en)	1978-08-08
ES429818A1 (es)	1976-09-01
AU464455B2 (en)	1975-08-28
AU7302574A (en)	1975-08-28
DD114416A5 (es)	1975-08-05
JPS5418278B2 (es)	1979-07-06
AR202040A1 (es)	1975-05-09
ES431287A1 (es)	1976-11-01

Publication	Publication Date	Title
EP0043546B1 (en)	1986-01-29	7-oxo-cephalosporins and 6-oxo-penicillins, their analogues and process for their preparation
HU184140B (en)	1984-07-30	Process for preparing 7-cef-3-em-4-carboxylic acid derivatives
NO743198L (es)	1975-04-01
EP0036510B1 (en)	1984-11-21	Synisomer cephalosporin compounds and processes for their preparation
US3872086A (en)	1975-03-18	Certain disulfide derivatives of 2-azetidinones
DE2063268A1 (de)	1971-07-08	Antibiotika
NO152653B (no)	1985-07-22	Fremgangsmaate for fremstilling av en 7-(substituert)-amino-3-substituert tiometyl-delta 3-cefem-4-karboksylsyre
SU546282A3 (ru)	1977-02-05	Способ получени 7- -амино-7 метокси-цефалоспориновых эфиров
DK159154B (da)	1990-09-10	Fremgangsmaade til fremstilling af cephalosporinderivater eller salte deraf
FI75165C (fi)	1988-05-09	Foerbaettrat foerfarande foer framstaellning av penicillansyraklormetylestrar.
AU619201B2 (en)	1992-01-23	Process for the preparation of 3-exomethylene cepham derivatives
NO743197L (es)	1975-04-01
CA1056812A (en)	1979-06-19	7a-methoxycephalosporin compounds
CH637135A5 (en)	1983-07-15	Cephalosporin derivatives and a process for their preparation
Brownsort et al.	1987	Nitrile sulphides. Part 7. Synthesis of [1] benzopyrano [4, 3-c] isothiazoles and isothiazolo [4, 3-c] quinolines
NO148376B (no)	1983-06-20	Analogifremgangsmaate til fremstilling av terapeutisk virksomme 7-acylamino-3-halogen-cefalosporinforbindelser
EP0001149B1 (en)	1981-06-03	Process for the preparation of 3-bromomethyl-3-cephem-sulphoxide derivatives
NO752373L (es)	1976-01-05
NO743200L (es)	1975-04-01
US4092474A (en)	1978-05-30	Cephalosporins having a metaloxy group in 3-substituent
AT331983B (de)	1976-09-10	Verfahren zur herstellung eines neuen derivates der 7-trichlor-acetamido -3- desacetoxy-cephalosporansaure
CA1155835A (en)	1983-10-25	Process for preparing cephalosporin derivatives
DE2337105A1 (de)	1974-01-31	Antibiotika und verfahren zu ihrer herstellung
US4115646A (en)	1978-09-19	Process for preparing 7-aminocephalosporanic acid derivatives
NO743199L (es)	1975-04-01