IE42961B1 - Cephalosporin compounds - Google Patents
Cephalosporin compoundsInfo
- Publication number
- IE42961B1 IE42961B1 IE406/76A IE40676A IE42961B1 IE 42961 B1 IE42961 B1 IE 42961B1 IE 406/76 A IE406/76 A IE 406/76A IE 40676 A IE40676 A IE 40676A IE 42961 B1 IE42961 B1 IE 42961B1
- Authority
- IE
- Ireland
- Prior art keywords
- cephem
- carboxylic acid
- acid
- thiol
- compound according
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 8
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 7
- -1 Cephalosporin compounds Chemical class 0.000 title claims description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 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 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- IAIJXUHASIZJOZ-WPZCJLIBSA-N (6r)-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CC=3SC=CC=3)[C@H]2SC1 IAIJXUHASIZJOZ-WPZCJLIBSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 5
- 150000001782 cephems Chemical class 0.000 abstract description 4
- 150000001780 cephalosporins Chemical class 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 25
- 229910052799 carbon Inorganic materials 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- 235000017557 sodium bicarbonate Nutrition 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 159000000000 sodium salts Chemical class 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 12
- 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 11
- 239000000284 extract Substances 0.000 description 11
- UOTQEHLQKASWQO-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1N=NN=C1S UOTQEHLQKASWQO-UHFFFAOYSA-N 0.000 description 10
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 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 8
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical class SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 3
- BKZLVXLDRQUFHT-UHFFFAOYSA-N 3-(5-sulfanylidene-2h-tetrazol-1-yl)propanoic acid Chemical compound OC(=O)CCN1N=NN=C1S BKZLVXLDRQUFHT-UHFFFAOYSA-N 0.000 description 3
- MORHPNKHDKWZHZ-UHFFFAOYSA-N 4-(5-sulfanylidene-2h-tetrazol-1-yl)butanoic acid Chemical compound OC(=O)CCCN1N=NN=C1S MORHPNKHDKWZHZ-UHFFFAOYSA-N 0.000 description 3
- GNCPNAQCXHPXOX-UHFFFAOYSA-N 5-sulfanylidene-1,2-dihydrotriazole-4-carboxylic acid Chemical compound OC(=O)C1=NNNC1=S GNCPNAQCXHPXOX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 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 3
- 238000001704 evaporation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- HRDIKQFHFOTXDL-UHFFFAOYSA-N 1-o,1-o-diethyl 3-o-methyl propane-1,1,3-tricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)CCC(=O)OC HRDIKQFHFOTXDL-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- 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 2
- CVYLWKKBVGCWBQ-UHFFFAOYSA-N 2-(methylsulfanylcarbothioylamino)acetic acid Chemical compound CSC(=S)NCC(O)=O CVYLWKKBVGCWBQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XSHRIGOGVGDZIX-UHFFFAOYSA-N 3-(5-sulfanylidene-2h-tetrazol-1-yl)propanamide Chemical compound NC(=O)CCN1N=NN=C1S XSHRIGOGVGDZIX-UHFFFAOYSA-N 0.000 description 2
- PBBKFUOGKZPENI-UHFFFAOYSA-N 3-(methylsulfanylcarbothioylamino)propanoic acid Chemical compound CSC(=S)NCCC(O)=O PBBKFUOGKZPENI-UHFFFAOYSA-N 0.000 description 2
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 2
- JQATYBMVAFRQNM-UHFFFAOYSA-N 4-(methylsulfanylcarbothioylamino)butanoic acid Chemical compound CSC(=S)NCCCC(O)=O JQATYBMVAFRQNM-UHFFFAOYSA-N 0.000 description 2
- BQIWJFVLKNPOGK-UHFFFAOYSA-N 6-(5-sulfanylidene-2h-tetrazol-1-yl)hexanoic acid Chemical compound OC(=O)CCCCCN1N=NN=C1S BQIWJFVLKNPOGK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- JNQWOJBFORLKBB-UHFFFAOYSA-M [Na+].C(=O)([O-])CC1=NNC(=N1)S Chemical compound [Na+].C(=O)([O-])CC1=NNC(=N1)S JNQWOJBFORLKBB-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- YJLZLUSKICMKJX-UHFFFAOYSA-N chloroform;formic acid;propan-2-ol Chemical compound OC=O.CC(C)O.ClC(Cl)Cl YJLZLUSKICMKJX-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 2
- IYPSSPPKMLXXRN-UHFFFAOYSA-N ethyl 2-isothiocyanatoacetate Chemical compound CCOC(=O)CN=C=S IYPSSPPKMLXXRN-UHFFFAOYSA-N 0.000 description 2
- ORPRVDCFUJMTEZ-UHFFFAOYSA-N ethyl 3-(1-benzyl-5-chlorotriazol-4-yl)propanoate Chemical compound ClC1=C(CCC(=O)OCC)N=NN1CC1=CC=CC=C1 ORPRVDCFUJMTEZ-UHFFFAOYSA-N 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- LWBZAWFABLYPDP-UHFFFAOYSA-N 1,2-dihydrotriazole-5-thione;sodium Chemical class [Na].S=C1C=NNN1 LWBZAWFABLYPDP-UHFFFAOYSA-N 0.000 description 1
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical class NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- AXKPLOXWGRGZDU-UHFFFAOYSA-N 11-(5-sulfanylidene-2h-tetrazol-1-yl)undecanamide Chemical compound NC(=O)CCCCCCCCCCN1NN=NC1=S AXKPLOXWGRGZDU-UHFFFAOYSA-N 0.000 description 1
- MWJYRAUQODYNLH-UHFFFAOYSA-N 11-(5-sulfanylidene-2h-tetrazol-1-yl)undecanoic acid Chemical compound OC(=O)CCCCCCCCCCN1NN=NC1=S MWJYRAUQODYNLH-UHFFFAOYSA-N 0.000 description 1
- HNRQWFXWCSGIQR-UHFFFAOYSA-N 11-(methylsulfanylcarbothioylamino)undecanoic acid Chemical compound CSC(=S)NCCCCCCCCCCC(O)=O HNRQWFXWCSGIQR-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical class OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- RHJDIDBHTPSUBU-UHFFFAOYSA-N 2-(5-sulfanylidene-1,2-dihydrotriazol-4-yl)acetic acid Chemical compound OC(=O)CC=1N=NNC=1S RHJDIDBHTPSUBU-UHFFFAOYSA-N 0.000 description 1
- RWVPFRSKYWPNIT-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)acetamide Chemical compound NC(=O)CN1N=NN=C1S RWVPFRSKYWPNIT-UHFFFAOYSA-N 0.000 description 1
- AMYWRUIDQFIWOZ-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)pentanoic acid Chemical compound CCCC(C(O)=O)N1N=NN=C1S AMYWRUIDQFIWOZ-UHFFFAOYSA-N 0.000 description 1
- GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 description 1
- JVWNFKQEATXYQZ-UHFFFAOYSA-N 2-aminobutanoic acid 2-aminohexanoic acid 2-aminopentanoic acid Chemical compound NC(C(=O)O)CCCC.NC(C(=O)O)CCC.NC(C(=O)O)CC JVWNFKQEATXYQZ-UHFFFAOYSA-N 0.000 description 1
- PQWPMAKLNGBTJD-UHFFFAOYSA-N 2-methyl-2-(5-sulfanylidene-1,2-dihydrotriazol-4-yl)propanoic acid Chemical compound OC(=O)C(C)(C)C=1N=NNC=1S PQWPMAKLNGBTJD-UHFFFAOYSA-N 0.000 description 1
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 description 1
- DIAYJFJPTYLIQC-UHFFFAOYSA-N 3-(1-benzyl-5-oxo-2h-triazol-4-yl)propanoic acid Chemical compound O=C1C(CCC(=O)O)=NNN1CC1=CC=CC=C1 DIAYJFJPTYLIQC-UHFFFAOYSA-N 0.000 description 1
- HDCRPLDQSLGQQA-UHFFFAOYSA-N 3-(5-sulfanylidene-2h-tetrazol-1-yl)butanoic acid Chemical compound OC(=O)CC(C)N1N=NN=C1S HDCRPLDQSLGQQA-UHFFFAOYSA-N 0.000 description 1
- XXEVPKIDUINGSD-UHFFFAOYSA-N 3-(methylsulfanylcarbothioylamino)butanoic acid Chemical compound CSC(=S)NC(C)CC(O)=O XXEVPKIDUINGSD-UHFFFAOYSA-N 0.000 description 1
- WHNOEVOISMYRDZ-UHFFFAOYSA-N 4-(5-sulfanylidene-2h-tetrazol-1-yl)butanamide Chemical compound NC(=O)CCCN1N=NN=C1S WHNOEVOISMYRDZ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- AZMSMQZKBRVUHB-UHFFFAOYSA-N 5-sulfanylidene-1,2-dihydrotriazole-4-carboxamide Chemical compound NC(=O)C1=NNNC1=S AZMSMQZKBRVUHB-UHFFFAOYSA-N 0.000 description 1
- CDAOOUIBHCVUSV-UHFFFAOYSA-N 6-(5-sulfanylidene-2h-tetrazol-1-yl)hexanamide Chemical compound NC(=O)CCCCCN1N=NN=C1S CDAOOUIBHCVUSV-UHFFFAOYSA-N 0.000 description 1
- OJIOPDXKHZOIIZ-UHFFFAOYSA-N 6-(methylsulfanylcarbothioylamino)hexanoic acid Chemical compound CSC(=S)NCCCCCC(O)=O OJIOPDXKHZOIIZ-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CFZOLBHYUXCTNM-UHFFFAOYSA-N CN1N=NN=C1CC(N)=O Chemical compound CN1N=NN=C1CC(N)=O CFZOLBHYUXCTNM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ZREDENZRJAVARE-UHFFFAOYSA-N OC1=C(CCC(=O)OCC)N=NN1CC1=CC=CC=C1 Chemical compound OC1=C(CCC(=O)OCC)N=NN1CC1=CC=CC=C1 ZREDENZRJAVARE-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YPEDJASLNYHCRR-UHFFFAOYSA-N SC1=C(CCC(=O)O)N=NN1CC1=CC=CC=C1 Chemical compound SC1=C(CCC(=O)O)N=NN1CC1=CC=CC=C1 YPEDJASLNYHCRR-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QMIBOUMLJFRULI-UHFFFAOYSA-M [O-]C(CC(N=NN1)=C1S)=O.[Na+] Chemical compound [O-]C(CC(N=NN1)=C1S)=O.[Na+] QMIBOUMLJFRULI-UHFFFAOYSA-M 0.000 description 1
- AGCWSCLQLWMQKM-UHFFFAOYSA-M [O-]C(CCCC(N=NN1)=C1S)=O.[Na+] Chemical compound [O-]C(CCCC(N=NN1)=C1S)=O.[Na+] AGCWSCLQLWMQKM-UHFFFAOYSA-M 0.000 description 1
- SZEABXKOFYZRNX-SWEFTRPJSA-L [O-]C(CN1N=NN=C1SCC(CS[C@@H]1C2NC(CC3=CC=CS3)=O)=C(C([O-])=O)N1C2=O)=O.[Na+].[Na+] Chemical compound [O-]C(CN1N=NN=C1SCC(CS[C@@H]1C2NC(CC3=CC=CS3)=O)=C(C([O-])=O)N1C2=O)=O.[Na+].[Na+] SZEABXKOFYZRNX-SWEFTRPJSA-L 0.000 description 1
- VXDSLUMUNWTSDB-UHFFFAOYSA-N acetic acid;chloroform;methanol Chemical compound OC.CC(O)=O.ClC(Cl)Cl VXDSLUMUNWTSDB-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- UDLLFLQFQMACJB-UHFFFAOYSA-N azidomethylbenzene Chemical compound [N-]=[N+]=NCC1=CC=CC=C1 UDLLFLQFQMACJB-UHFFFAOYSA-N 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
- 229940000635 beta-alanine Drugs 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- TUVQNCVMAQUSIM-UHFFFAOYSA-N n-methyl-2-(2h-tetrazol-5-ylsulfanyl)acetamide Chemical compound CNC(=O)CSC=1N=NNN=1 TUVQNCVMAQUSIM-UHFFFAOYSA-N 0.000 description 1
- ZQHKBCHGNNTTDZ-UHFFFAOYSA-N n-methyl-2-(tetrazol-1-yl)acetamide Chemical compound CNC(=O)CN1C=NN=N1 ZQHKBCHGNNTTDZ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 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 1
- 239000012071 phase Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SKMDLXMIOJGLBV-UHFFFAOYSA-N sodium;5-sulfanylidene-1,2-dihydrotriazole-4-carboxamide Chemical compound [Na].NC(=O)C1=NNNC1=S SKMDLXMIOJGLBV-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 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
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- FHDFMQBXVDYVGQ-UHFFFAOYSA-N triethyl 2-methylpropane-1,1,2-tricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(C)(C)C(=O)OCC FHDFMQBXVDYVGQ-UHFFFAOYSA-N 0.000 description 1
- CTFRGNLAGFUMHR-UHFFFAOYSA-N triethyl ethane-1,1,1-tricarboxylate Chemical compound CCOC(=O)C(C)(C(=O)OCC)C(=O)OCC CTFRGNLAGFUMHR-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55372275A | 1975-02-27 | 1975-02-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42961L IE42961L (en) | 1976-08-27 |
| IE42961B1 true IE42961B1 (en) | 1980-11-19 |
Family
ID=24210475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE406/76A IE42961B1 (en) | 1975-02-27 | 1976-02-27 | Cephalosporin compounds |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4112086A (en) * | 1976-11-02 | 1978-09-05 | Smithkline Corporation | 7β-Acylamino-3-(phosphonoalkyl and esterified phosphonoalkyl substituted tetrazolylthiomethyl)cephalosporins |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2068419A1 (en) * | 1969-10-27 | 1971-08-27 | Fujisawa Pharmaceutical Co | Antibacterial cephalosporin compsns |
| BE793037A (fr) * | 1971-12-23 | 1973-06-20 | Fujisawa Pharmaceutical Co | Procede de preparation de derives d'acide 7-acylamino-3-substitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus |
| JPS612674B2 (enrdf_load_stackoverflow) * | 1974-06-20 | 1986-01-27 | Meiji Seika Co |
-
1976
- 1976-01-27 ZA ZA451A patent/ZA76451B/xx unknown
- 1976-02-16 CA CA245,853A patent/CA1072543A/en not_active Expired
- 1976-02-18 GB GB6367/76A patent/GB1544703A/en not_active Expired
- 1976-02-19 IL IL49066A patent/IL49066A/xx unknown
- 1976-02-20 BE BE164478A patent/BE838760A/xx not_active IP Right Cessation
- 1976-02-23 IT IT20483/76A patent/IT1055451B/it active
- 1976-02-24 JP JP51019818A patent/JPS51110595A/ja active Pending
- 1976-02-25 LU LU74427A patent/LU74427A1/xx unknown
- 1976-02-25 DE DE19762607681 patent/DE2607681A1/de not_active Withdrawn
- 1976-02-25 AU AU11406/76A patent/AU499565B2/en not_active Expired
- 1976-02-25 NL NL7601935A patent/NL7601935A/xx not_active Application Discontinuation
- 1976-02-27 FR FR7605506A patent/FR2302098A1/fr active Granted
- 1976-02-27 IE IE406/76A patent/IE42961B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7601935A (nl) | 1976-08-31 |
| IE42961L (en) | 1976-08-27 |
| IT1055451B (it) | 1981-12-21 |
| GB1544703A (en) | 1979-04-25 |
| DE2607681A1 (de) | 1976-09-09 |
| IL49066A0 (en) | 1976-04-30 |
| CA1072543A (en) | 1980-02-26 |
| AU499565B2 (en) | 1979-04-26 |
| BE838760A (fr) | 1976-08-20 |
| LU74427A1 (enrdf_load_stackoverflow) | 1976-08-13 |
| FR2302098B1 (enrdf_load_stackoverflow) | 1979-09-21 |
| FR2302098A1 (fr) | 1976-09-24 |
| AU1140676A (en) | 1977-09-01 |
| JPS51110595A (enrdf_load_stackoverflow) | 1976-09-30 |
| ZA76451B (en) | 1977-01-26 |
| IL49066A (en) | 1982-07-30 |
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