CA1041087A - SUBSTITUTED .alpha.-CARBOXY ACETAMIDOCEPHALOSPORINS - Google Patents

SUBSTITUTED .alpha.-CARBOXY ACETAMIDOCEPHALOSPORINS

Info

Publication number: CA1041087A
Authority: CA; Canada
Prior art keywords: thienyl; ylthiomethyl; cephem; reduced pressure; water
Prior art date: 1974-05-22
Legal status (The legal status 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 status listed.): Expired

Application number

CA227,351A

Other languages

English (en)

French (fr)

Other versions

CA227351S (en

Inventor

Pierre Crooij

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

RECHERCHE ET INDUSTRIE THERAPEUTIQUES RIT

Original Assignee

RECHERCHE ET INDUSTRIE THERAPEUTIQUES RIT

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.)

1974-05-22

Filing date

1975-05-20

Publication date

1978-10-24

1975-05-20 Application filed by RECHERCHE ET INDUSTRIE THERAPEUTIQUES RIT filed Critical RECHERCHE ET INDUSTRIE THERAPEUTIQUES RIT

1978-10-24 Application granted granted Critical

1978-10-24 Publication of CA1041087A publication Critical patent/CA1041087A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 13
238000000034 method Methods 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 9
229960002317 succinimide Drugs 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 4
XUTQHTOXGKVJPN-UHFFFAOYSA-N 7-azaniumyl-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)C2SC1 XUTQHTOXGKVJPN-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 1
230000001131 transforming effect Effects 0.000 claims 1
229930186147 Cephalosporin Natural products 0.000 abstract description 10
229940124587 cephalosporin Drugs 0.000 abstract description 10
150000001780 cephalosporins Chemical class 0.000 abstract description 8
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
239000000203 mixture Substances 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000001514 detection method Methods 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
-1 cephalosporin compounds Chemical class 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
229960004132 diethyl ether Drugs 0.000 description 7
239000010410 layer Substances 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
239000012043 crude product Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000607720 Serratia Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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 3
241000588772 Morganella morganii Species 0.000 description 3
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
244000309464 bull Species 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
RQTQBOHDZFBYFI-UHFFFAOYSA-N tert-butyl 2-thiophen-2-ylacetate Chemical compound CC(C)(C)OC(=O)CC1=CC=CS1 RQTQBOHDZFBYFI-UHFFFAOYSA-N 0.000 description 3
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 2
AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
INAOLJFAUXIMFC-UHFFFAOYSA-N benzyl 2-thiophen-2-ylacetate Chemical compound C=1C=CC=CC=1COC(=O)CC1=CC=CS1 INAOLJFAUXIMFC-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 2
229960003669 carbenicillin Drugs 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
230000021523 carboxylation Effects 0.000 description 2
238000006473 carboxylation reaction Methods 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
239000003610 charcoal Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
ASGIQPRGHDBJBR-XCGJVMPOSA-N (6r)-4-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1C=C(C(O)=O)N2C(=O)C[C@H]2S1 ASGIQPRGHDBJBR-XCGJVMPOSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 1
OIJPSMYQMUNKSB-UHFFFAOYSA-N 2-thiophen-2-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)C1=CC=CS1 OIJPSMYQMUNKSB-UHFFFAOYSA-N 0.000 description 1
LBEYVKSLSBONOF-UHFFFAOYSA-N 3-O-tert-butyl 1-O-thiophen-3-yl propanedioate Chemical compound C(CC(=O)OC1=CSC=C1)(=O)OC(C)(C)C LBEYVKSLSBONOF-UHFFFAOYSA-N 0.000 description 1
PDCRXJKDRLZGBX-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxy]-3-oxo-2-thiophen-2-ylpropanoic acid Chemical compound CC(C)(C)OC(=O)C(C(O)=O)C1=CC=CS1 PDCRXJKDRLZGBX-UHFFFAOYSA-N 0.000 description 1
IZCKKYIBCWNRNP-UHFFFAOYSA-N 3-oxo-3-phenylmethoxy-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C(=O)O)C(=O)OCC1=CC=CC=C1 IZCKKYIBCWNRNP-UHFFFAOYSA-N 0.000 description 1
DDSSZBSJRNFOJW-UHFFFAOYSA-N 3-phenyl-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C(=O)O)CC1=CC=CC=C1 DDSSZBSJRNFOJW-UHFFFAOYSA-N 0.000 description 1
MKNQNPYGAQGARI-UHFFFAOYSA-N 4-(bromomethyl)phenol Chemical compound OC1=CC=C(CBr)C=C1 MKNQNPYGAQGARI-UHFFFAOYSA-N 0.000 description 1
CFYIUBWVKZQDOG-UHFFFAOYSA-N 4-[[2-[[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-oxobutanoic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1NC(=O)C(NC(=O)CNC(=O)CNC(=O)CCC(=O)O)CC1=CC=CC=C1 CFYIUBWVKZQDOG-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 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
241000894006 Bacteria Species 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241000607768 Shigella Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229960002376 chymotrypsin Drugs 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
KCWYOFZQRFCIIE-UHFFFAOYSA-N ethylsilane Chemical compound CC[SiH3] KCWYOFZQRFCIIE-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
MOAHAJQWMOMVFS-UHFFFAOYSA-N tert-butyl 2-thiophen-3-ylacetate Chemical compound CC(C)(C)OC(=O)CC=1C=CSC=1 MOAHAJQWMOMVFS-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

CA227,351A 1974-05-22 1975-05-20 SUBSTITUTED .alpha.-CARBOXY ACETAMIDOCEPHALOSPORINS Expired CA1041087A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US47226374A	1974-05-22	1974-05-22
US53798775A	1975-01-02	1975-01-02

Publications (1)

Publication Number	Publication Date
CA1041087A true CA1041087A (en)	1978-10-24

Family

ID=27043712

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA227,351A Expired CA1041087A (en)	1974-05-22	1975-05-20	SUBSTITUTED .alpha.-CARBOXY ACETAMIDOCEPHALOSPORINS

Country Status (13)

Country	Link
JP (1)	JPS511489A (da)
AU (1)	AU8059475A (da)
CA (1)	CA1041087A (da)
DE (1)	DE2521062A1 (da)
DK (1)	DK203575A (da)
ES (1)	ES437182A1 (da)
FR (1)	FR2271827A1 (da)
GB (1)	GB1457237A (da)
IE (1)	IE41622B1 (da)
IL (1)	IL47176A0 (da)
LU (1)	LU72530A1 (da)
NL (1)	NL7505962A (da)
SE (1)	SE7504669L (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5321191A (en) *	1976-08-10	1978-02-27	Shionogi & Co Ltd	7-arylmalonamidocephem derivatives
JPS60215690A (ja) *	1984-04-09	1985-10-29	Meiji Seika Kaisha Ltd	セフアロスポリン化合物及びそれを有効成分とする抗菌剤

1975
- 1975-04-23 SE SE7504669A patent/SE7504669L/xx unknown
- 1975-04-25 IL IL47176A patent/IL47176A0/xx unknown
- 1975-04-28 AU AU80594/75A patent/AU8059475A/en not_active Expired
- 1975-04-29 ES ES437182A patent/ES437182A1/es not_active Expired
- 1975-04-29 FR FR7513352A patent/FR2271827A1/fr not_active Withdrawn
- 1975-05-07 DK DK203575A patent/DK203575A/da unknown
- 1975-05-12 DE DE19752521062 patent/DE2521062A1/de active Pending
- 1975-05-20 CA CA227,351A patent/CA1041087A/en not_active Expired
- 1975-05-20 LU LU72530A patent/LU72530A1/xx unknown
- 1975-05-21 NL NL7505962A patent/NL7505962A/xx unknown
- 1975-05-21 GB GB2181675A patent/GB1457237A/en not_active Expired
- 1975-05-22 JP JP50061783A patent/JPS511489A/ja active Pending
- 1975-05-22 IE IE1145/75A patent/IE41622B1/en unknown

Also Published As

Publication number	Publication date
AU8059475A (en)	1976-11-04
DK203575A (da)	1975-11-23
LU72530A1 (da)	1975-10-08
IL47176A0 (en)	1975-06-25
SE7504669L (sv)	1975-11-24
DE2521062A1 (de)	1975-12-04
IE41622B1 (en)	1980-02-13
IE41622L (en)	1975-11-22
ES437182A1 (es)	1977-01-16
GB1457237A (en)	1976-12-01
NL7505962A (nl)	1975-11-25
FR2271827A1 (da)	1975-12-19
JPS511489A (en)	1976-01-08

Publication	Publication Date	Title
FI67555C (fi)	1985-04-10	Foerfarande foer framstaellning av terapeutiskt anvaendbart (6 7r)-7-((z)-2-(2-aminotiazol-4-yl)-2-(2-karboxiprop-2-oxi imno)-acetamido)-3-(1-pyridiniummetyl)-cef-3-em-4-karboxyla t
JPH0567632B2 (da)	1993-09-27
CA1060432A (en)	1979-08-14	7 .alpha. METHOXYCEPHALOSPORIN DERIVATIVES
JPS6157316B2 (da)	1986-12-06
US4138555A (en)	1979-02-06	(6R,7R)-7-[2-aryl-2-(etherified oximino)acetamido]-3-carbamoyloxymethylceph-3-em-4-carboxylic acid 1-oxides
CA1041087A (en)	1978-10-24	SUBSTITUTED .alpha.-CARBOXY ACETAMIDOCEPHALOSPORINS
US4104469A (en)	1978-08-01	7-(Syn-α-alkoxy-iminofuryl)acetamido-3-(2-methyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
KR870002181B1 (ko)	1987-12-28	세팔로스포린의 제조방법
US4031083A (en)	1977-06-21	Cephalosporin antibiotics
US4103085A (en)	1978-07-25	7-(Syn-α-alkoxy-iminofurylacetamido-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US4060686A (en)	1977-11-29	Cephalosporins having a 7-(carboxy substituted α-etherified oximinoarylacetamido) group
US4151352A (en)	1979-04-24	7-Amino-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US4162360A (en)	1979-07-24	3-Carbamoyloxymethyl-7-substituted oximino acetamido cephalosporanic acid derivatives
DE3115935A1 (de)	1982-02-25	Substituierte 7-((alpha)-oxyimino-acetamido)-cephalosporine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische oder veterinaermedizinische mittel
US4093804A (en)	1978-06-06	Pyridiniummethylaryl-substituted cephalosporin derivatives
EP0015690B1 (en)	1983-04-06	Penicillin derivatives, process for their preparation and pharmaceutical composition comprising them
CA1113455A (en)	1981-12-01	7-acylamido-3-(2-carboxyalkyl-2,3-dihydro-3-triazolo ¬4,3-b\| pyridazin-3-on-6-ylthiomethyl)-3-cephem- 4-carboxylic acids
US4182863A (en)	1980-01-08	7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
NO760151L (da)	1976-07-20
US3996216A (en)	1976-12-07	3-Heterothio derivatives of (formylamino)acetylamino-7-alpha-methoxy cephalosporins
US3994889A (en)	1976-11-30	3-Heterothio derivatives of (α-thiocarbonylaminol)-7α-methoxy-cephalosporins
US4003893A (en)	1977-01-18	3-Heterothio[(thioalkyl)thioacetyl]cephalosporanic derivatives
US3996219A (en)	1976-12-07	3-Heterothio derivatives of (α-thiocarbonylamino) cephalosporins
US3994875A (en)	1976-11-30	Antibiotics
US4497811A (en)	1985-02-05	1-Oxadethiacephalosporin compound and antibacterial agent containing the _same