CH619235A5 - - Google Patents

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Info

Publication number: CH619235A5
Authority: CH; Switzerland
Prior art keywords: group; formula; atoms; alkyl; triazol
Prior art date: 1974-06-20

Application number

CH806775A

Other languages

German (de)

English (en)

Inventor

Fumio Kai

Toshinori Saito

Shigeo Seki

Toyoaki Kawasaki

Original Assignee

Meiji Seika Kaisha

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.)

1974-06-20

Filing date

1975-06-20

Publication date

1980-09-15

1975-06-20 Application filed by Meiji Seika Kaisha filed Critical Meiji Seika Kaisha

1980-09-15 Publication of CH619235A5 publication Critical patent/CH619235A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 55
-1 cephalosporin compound Chemical class 0.000 claims description 50
125000004432 carbon atom Chemical group C* 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 23
238000000034 method Methods 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
229930186147 Cephalosporin Natural products 0.000 claims description 18
229940124587 cephalosporin Drugs 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 15
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000005907 alkyl ester group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000004450 alkenylene group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
159000000000 sodium salts Chemical class 0.000 description 18
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
230000000845 anti-microbial effect Effects 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
150000001780 cephalosporins Chemical class 0.000 description 15
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
241000588767 Proteus vulgaris Species 0.000 description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
229940007042 proteus vulgaris Drugs 0.000 description 13
238000012360 testing method Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
241000607142 Salmonella Species 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
244000005700 microbiome Species 0.000 description 12
239000000047 product Substances 0.000 description 12
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 11
241000588724 Escherichia coli Species 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000003242 anti bacterial agent Substances 0.000 description 10
229940088710 antibiotic agent Drugs 0.000 description 10
238000006114 decarboxylation reaction Methods 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 9
235000019260 propionic acid Nutrition 0.000 description 9
239000002904 solvent Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000000862 absorption spectrum Methods 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
241000191940 Staphylococcus Species 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
239000002585 base Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 3
231100000053 low toxicity Toxicity 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
239000000376 reactant Substances 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
150000003852 triazoles Chemical group 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 2
MCLMZMISZCYBBG-UHFFFAOYSA-N 3-ethylheptanoic acid Chemical compound CCCCC(CC)CC(O)=O MCLMZMISZCYBBG-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001243 acetic acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 2
229960001139 cefazolin Drugs 0.000 description 2
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 description 2
230000000052 comparative effect Effects 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012071 phase Substances 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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000004672 propanoic acids Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
OYLWNIRWHSRRDC-UHFFFAOYSA-N 2-(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)acetic acid Chemical compound OC(=O)CC1=NN=C(S)N1 OYLWNIRWHSRRDC-UHFFFAOYSA-N 0.000 description 1
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
QTAITSULXIMAEA-UHFFFAOYSA-N 4-(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN=C(S)N1 QTAITSULXIMAEA-UHFFFAOYSA-N 0.000 description 1
108020004256 Beta-lactamase Proteins 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001253 acrylic acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
229960003866 cefaloridine Drugs 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
150000001782 cephems Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
UIUWNILCHFBLEQ-UHFFFAOYSA-N pent-3-enoic acid Chemical compound CC=CCC(O)=O UIUWNILCHFBLEQ-UHFFFAOYSA-N 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
HWEXKRHYVOGVDA-UHFFFAOYSA-M sodium;3-trimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[Si](C)(C)CCCS([O-])(=O)=O HWEXKRHYVOGVDA-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- 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

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

CH806775A 1974-06-20 1975-06-20 CH619235A5 (nl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP49069641A JPS612674B2 (nl)	1974-06-20	1974-06-20

Publications (1)

Publication Number	Publication Date
CH619235A5 true CH619235A5 (nl)	1980-09-15

Family

ID=13408675

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH806775A CH619235A5 (nl)	1974-06-20	1975-06-20

Country Status (14)

Country	Link
US (1)	US4113944A (nl)
JP (1)	JPS612674B2 (nl)
AR (2)	AR211850A1 (nl)
BE (1)	BE830457A (nl)
CA (1)	CA1072950A (nl)
CH (1)	CH619235A5 (nl)
DE (1)	DE2527653C3 (nl)
FR (1)	FR2275479A1 (nl)
GB (1)	GB1467217A (nl)
HU (2)	HU176287B (nl)
IL (1)	IL47477A (nl)
NL (1)	NL166943C (nl)
SE (1)	SE429235B (nl)
YU (1)	YU37348B (nl)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4297489A (en) *	1974-09-03	1981-10-27	Bristol-Myers Company	7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids
ZA76451B (en) *	1975-02-27	1977-01-26	Smithkline Corp	New cephalosporin compounds
US4220644A (en) *	1976-05-03	1980-09-02	Smithkline Corporation	7-Acylamino-3-(substituted tetrazolyl thiomethyl) cephalosporins
NZ186610A (en) *	1977-03-07	1979-11-01	Lilly Co Eli	Preparing of cephalosporins where the acetoxy group is displaced by a sulphur nucleophile
US4174324A (en) *	1977-06-30	1979-11-13	Smithkline Corporation	3-(Carboxymethyl)thio-1H-1,2,4-triazol-5-thione
US4404375A (en) *	1980-04-30	1983-09-13	American Cyanamid Company	Cephalosporanic acid derivatives
US4404376A (en) *	1980-04-30	1983-09-13	American Cyanamid Company	Cephalosporanic acid derivatives
US4404374A (en) *	1980-04-30	1983-09-13	American Cyanamid Company	Cephalosporanic acid derivatives
US4336375A (en) *	1980-04-30	1982-06-22	American Cyanamid Company	Cephalosporanic acid derivatives
US4334062A (en) *	1980-10-24	1982-06-08	American Cyanamid Company	Cephalosporanic acid derivatives
JP2534588Y2 (ja) *	1992-05-19	1997-04-30	鐘紡株式会社	アンケートボード

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH527215A (de) *	1967-04-15	1972-08-31	Fujisawa Pharmaceutical Co	Verfahren zur Herstellung von 3,7-disubstituierten Cephalosporinderivaten
US3819623A (en) *	1968-04-12	1974-06-25	Fujisawa Pharmaceutical Co	3,7-disubstituted cephalosporin compounds
US3641021A (en) *	1969-04-18	1972-02-08	Lilly Co Eli	3 7-(ring-substituted) cephalosporin compounds
JPS49124574A (nl) *	1972-09-15	1974-11-28
US3989694A (en) *	1974-12-27	1976-11-02	Smithkline Corporation	7-Acyl-3-(substituted triazolyl thiomethyl)cephalosporins

1974
- 1974-06-20 JP JP49069641A patent/JPS612674B2/ja not_active Expired
1975
- 1975-06-13 IL IL47477A patent/IL47477A/xx unknown
- 1975-06-19 GB GB2607175A patent/GB1467217A/en not_active Expired
- 1975-06-19 HU HU75ME1960A patent/HU176287B/hu not_active IP Right Cessation
- 1975-06-19 AR AR259284A patent/AR211850A1/es active
- 1975-06-19 YU YU1574/75A patent/YU37348B/xx unknown
- 1975-06-19 SE SE7507124A patent/SE429235B/xx not_active IP Right Cessation
- 1975-06-19 HU HU75ME00001866A patent/HU172045B/hu not_active IP Right Cessation
- 1975-06-19 US US05/588,555 patent/US4113944A/en not_active Expired - Lifetime
- 1975-06-20 NL NL7507404.A patent/NL166943C/nl not_active IP Right Cessation
- 1975-06-20 CA CA229,809A patent/CA1072950A/en not_active Expired
- 1975-06-20 FR FR7519352A patent/FR2275479A1/fr active Granted
- 1975-06-20 DE DE2527653A patent/DE2527653C3/de not_active Expired
- 1975-06-20 BE BE157519A patent/BE830457A/xx not_active IP Right Cessation
- 1975-06-20 CH CH806775A patent/CH619235A5/de not_active IP Right Cessation
1976
- 1976-04-19 AR AR262927A patent/AR210118A1/es active

Also Published As

Publication number	Publication date
AU8217575A (en)	1976-12-23
FR2275479B1 (nl)	1979-10-19
YU37348B (en)	1984-08-31
JPS612674B2 (nl)	1986-01-27
BE830457A (fr)	1975-12-22
GB1467217A (en)	1977-03-16
HU176287B (en)	1981-01-28
IL47477A0 (en)	1975-08-31
JPS511487A (nl)	1976-01-08
YU157475A (en)	1983-04-27
NL7507404A (nl)	1975-12-23
DE2527653C3 (de)	1981-01-22
AR210118A1 (es)	1977-06-30
US4113944A (en)	1978-09-12
AR211850A1 (es)	1978-03-31
CA1072950A (en)	1980-03-04
SE7507124L (sv)	1975-12-22
DE2527653A1 (de)	1976-05-06
NL166943C (nl)	1981-10-15
HU172045B (hu)	1978-05-28
IL47477A (en)	1978-09-29
FR2275479A1 (fr)	1976-01-16
SE429235B (sv)	1983-08-22
DE2527653B2 (de)	1980-05-08
NL166943B (nl)	1981-05-15

Publication	Publication Date	Title
CH628058A5 (de)	1982-02-15	Verfahren zur herstellung von cephemverbindungen.
CH634578A5 (de)	1983-02-15	Verfahren zur herstellung von neuen cephalosporinderivaten.
CH641467A5 (de)	1984-02-29	(2-(syn)-carbamoyloximinoacetamido)-cephalosporine.
CH619235A5 (nl)	1980-09-15
DE3233377A1 (de)	1983-03-24	Cephalosporinisochinoliniumbetaine und sie enthaltende pharmazeutische mittel
CH657857A5 (de)	1986-09-30	In 7-stellung substituierte 3-vinyl-3-cephemverbindungen und verfahren zur herstellung derselben.
DE2056983B2 (de)	1979-11-15	S-Heterocyclylthiomethyl-Cephalosporine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
CH626090A5 (nl)	1981-10-30
DE3035259C2 (de)	1986-03-13	Cephalosporinverbindungen, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
DE2239947A1 (de)	1973-03-15	Cephalosporinverbindungen und verfahren zu deren herstellung
CH583242A5 (de)	1976-12-31	Verfahren zur Herstellung von Verbindungen der Cephalosporinreihe
DE2638028A1 (de)	1977-03-10	Neue cephalosporinverbindungen
EP0553792B1 (de)	1999-05-26	Verfahren zur Herstellung von Ceftriaxon-dinatriumsalzhemiheptahydrat
CH627758A5 (en)	1982-01-29	Process for the preparation of the syn isomer or a mixture of the syn isomer and anti isomer of 7beta-acylamidoceph-3-em-4-carboxylic acids with the antibiotic activity
DE2600880A1 (de)	1977-07-21	Neue cephalosporine, verfahren zur herstellung derselben und mittel mit einem gehalt derselben
CH634326A5 (de)	1983-01-31	2-hydroxyiminoacetamido-cephemcarbonsaeuren und ihre herstellung.
DE2336344A1 (de)	1974-03-14	Penicillin- und cephalosporin-rsulfoxide, ihre salze und ester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2236422C2 (de)	1981-12-10	Cephalosporinverbindungen und Verfahren zu deren Herstellung
DE2559932C2 (de)	1983-04-21	Cephalosporine, Verfahren zur Herstellung derselben und Mittel mit einem Gehalt derselben
DE2841706C2 (de)	1982-11-04	N,N-Dimethylacetamid-Addukt der 7-[D(-)-&alpha;-(4-Äthyl-2,3-dioxo-1-piperazincarboxamido)-&alpha;-(4-hydroxyphenyl)-acetamido]-3-[5-(1-methyl-1,2,3,4-tetrazolyl)-thiomethyl]-&Delta;&uarr;3&uarr;-cephem--4-carbonsäure, Verfahren zu seiner Herstellung und seine Verwendung
AT309684B (de)	1973-08-27	Verfahren zur Herstellung von neuen Penicillinen und Cephalosporinen
DD201142A5 (de)	1983-07-06	Verfahren zur herstellung von bistetrazolyl-methylsubstituierten cephalosporiantibiotika
DE1445701A1 (de)	1969-08-28	Verfahren zur Herstellung von Cephalosporin-Verbindungen
DE2702025A1 (de)	1977-07-21	Neue derivate des cephalosporins, ihre herstellung und die sie enthaltenden zusammensetzungen
AT314086B (de)	1974-03-25	Verfahren zur Herstellung von neuen Cephalosporinverbindungen

Legal Events

Date	Code	Title	Description
1993-02-26	PL	Patent ceased
2024-10-31	PL	Patent ceased