GB1576625A - Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof - Google Patents
Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof Download PDFInfo
- Publication number
- GB1576625A GB1576625A GB14916/76A GB1491676A GB1576625A GB 1576625 A GB1576625 A GB 1576625A GB 14916/76 A GB14916/76 A GB 14916/76A GB 1491676 A GB1491676 A GB 1491676A GB 1576625 A GB1576625 A GB 1576625A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- group
- amino
- methoxyimino
- acetamido
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims description 71
- 238000002360 preparation method Methods 0.000 title description 38
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 title description 2
- -1 nitro, hydroxy Chemical group 0.000 claims description 290
- 150000001875 compounds Chemical class 0.000 claims description 280
- 238000006243 chemical reaction Methods 0.000 claims description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- 150000003839 salts Chemical class 0.000 claims description 87
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 81
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 72
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 72
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000004423 acyloxy group Chemical group 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
- 125000006239 protecting group Chemical group 0.000 claims description 31
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical group 0.000 claims description 28
- 125000004442 acylamino group Chemical group 0.000 claims description 26
- 238000003379 elimination reaction Methods 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 13
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 8
- RTRCVCSWKHSZJC-LNUXAPHWSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC=2SC=NN=2)C(=O)O)C1=O)C=1N=C(SC=1)NC=O RTRCVCSWKHSZJC-LNUXAPHWSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- QDDMXPSXDJRLNO-LESKNEHBSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)COC(N)=O)C(=O)O)C1=O)C=1N=C(SC=1)N QDDMXPSXDJRLNO-LESKNEHBSA-N 0.000 claims description 6
- HJJDBAOLQAWBMH-WCRCJTMVSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O)=NOC HJJDBAOLQAWBMH-WCRCJTMVSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- SRSVDFPJBXWEGG-LNUXAPHWSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC=2SC(=NN=2)C)C(=O)O)C1=O)C=1N=C(SC=1)N SRSVDFPJBXWEGG-LNUXAPHWSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical group [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- FHYWAOQGXIZAAF-LESKNEHBSA-N (6r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]12)CC(CO)=C(C(O)=O)N1C(=O)C2NC(=O)C(=NOC)C1=CSC(N)=N1 FHYWAOQGXIZAAF-LESKNEHBSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- TYSUXLWLQIYEPJ-WCRCJTMVSA-N (6R)-3-(carbamoyloxymethyl)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)COC(N)=O)C(=O)O)C1=O)C=1N=C(SC=1)NC=O TYSUXLWLQIYEPJ-WCRCJTMVSA-N 0.000 claims description 3
- FRJYFZQECCODGB-XPKAQORNSA-N (6R)-7-[[2-methoxyimino-2-[2-(2-methylbutan-2-yloxycarbonylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC=2SC(=NN=2)C)C(=O)O)C1=O)C=1N=C(SC=1)NC(=O)OC(C)(C)CC FRJYFZQECCODGB-XPKAQORNSA-N 0.000 claims description 3
- CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical compound OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 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 claims description 2
- MCSWUKXFFGUOQE-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-N-(3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undec-1(8)-en-4-yl)-2-methoxyiminoacetamide Chemical compound C12SCC(COC3=O)=C3N2C(=O)C1NC(=O)C(=NOC)C1=CSC(N)=N1 MCSWUKXFFGUOQE-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 9
- NWJSHDLORUZMLL-LESKNEHBSA-N (6R)-3-(hydroxymethyl)-7-[[2-methoxyimino-2-[2-[(2,2,2-trifluoroacetyl)amino]-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)CO)C(=O)O)C1=O)C=1N=C(SC=1)NC(C(F)(F)F)=O NWJSHDLORUZMLL-LESKNEHBSA-N 0.000 claims 1
- YSFVFWQKYKNZLS-LESKNEHBSA-N (6R)-3-formyl-7-[[2-methoxyimino-2-[2-[(2,2,2-trifluoroacetyl)amino]-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)C=O)C(=O)O)C1=O)C=1N=C(SC=1)NC(C(F)(F)F)=O YSFVFWQKYKNZLS-LESKNEHBSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 409
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 282
- 239000000203 mixture Substances 0.000 description 192
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 131
- 239000000243 solution Substances 0.000 description 130
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 121
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 116
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 111
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 105
- 239000007864 aqueous solution Substances 0.000 description 96
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 82
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 80
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 79
- 239000002904 solvent Substances 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
- 238000003756 stirring Methods 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
- 238000001816 cooling Methods 0.000 description 59
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 56
- 239000010410 layer Substances 0.000 description 46
- 239000011541 reaction mixture Substances 0.000 description 46
- 239000013078 crystal Substances 0.000 description 40
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 40
- 235000019341 magnesium sulphate Nutrition 0.000 description 40
- 238000001914 filtration Methods 0.000 description 38
- 230000002829 reductive effect Effects 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
- 239000000284 extract Substances 0.000 description 35
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 35
- 235000017557 sodium bicarbonate Nutrition 0.000 description 35
- 239000000843 powder Substances 0.000 description 32
- 239000011780 sodium chloride Substances 0.000 description 31
- 125000002252 acyl group Chemical group 0.000 description 29
- 239000000706 filtrate Substances 0.000 description 29
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 27
- 235000011054 acetic acid Nutrition 0.000 description 26
- 239000003921 oil Substances 0.000 description 26
- 239000007858 starting material Substances 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- 230000007062 hydrolysis Effects 0.000 description 22
- 238000006460 hydrolysis reaction Methods 0.000 description 22
- 239000000725 suspension Substances 0.000 description 22
- 230000001376 precipitating effect Effects 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 229910052783 alkali metal Inorganic materials 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- 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 15
- 238000004440 column chromatography Methods 0.000 description 15
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000002198 insoluble material Substances 0.000 description 14
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 12
- 230000002411 adverse Effects 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000007796 conventional method Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 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 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- NLARCUDOUOQRPB-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CON=C(C(O)=O)C1=CSC(N)=N1 NLARCUDOUOQRPB-UHFFFAOYSA-N 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 7
- 230000008030 elimination Effects 0.000 description 7
- POBMBNPEUPDXRS-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOC(=O)C(=NOC)C1=CSC(N)=N1 POBMBNPEUPDXRS-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 150000007522 mineralic acids Chemical class 0.000 description 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- DDLWWOLZXHAVNY-PVQCJRHBSA-N (6R)-3-(carbamoyloxymethyl)-7-[[2-(3-hydroxyphenyl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)COC(N)=O)C(=O)O)C1=O)C1=CC(=CC=C1)O DDLWWOLZXHAVNY-PVQCJRHBSA-N 0.000 description 6
- VGIJLQLDEHZKNU-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-methoxyiminoacetic acid Chemical compound CON=C(C(O)=O)C1=CC=CC(O)=C1 VGIJLQLDEHZKNU-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
- 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 6
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 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 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- PAVLRKXGMXXRRM-LWPABBACSA-M sodium (6R)-3-(carbamoyloxymethyl)-7-[[2-(3-hydroxyphenyl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CON=C(C(=O)NC1[C@@H]2N(C(=C(CS2)COC(N)=O)C(=O)[O-])C1=O)C1=CC(=CC=C1)O.[Na+] PAVLRKXGMXXRRM-LWPABBACSA-M 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- FLKYBGKDCCEQQM-ZHWMGRLRSA-M sodium;(6r)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)C(NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-ZHWMGRLRSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- MXJGKTHZWIGRJG-UHFFFAOYSA-N tert-butyl 2-aminooxyacetate Chemical compound CC(C)(C)OC(=O)CON MXJGKTHZWIGRJG-UHFFFAOYSA-N 0.000 description 1
- CZJIOLXNSPBYNA-UHFFFAOYSA-N tert-butyl 2-aminooxypropanoate Chemical compound NOC(C)C(=O)OC(C)(C)C CZJIOLXNSPBYNA-UHFFFAOYSA-N 0.000 description 1
- CVAWKJKISIPBOD-UHFFFAOYSA-N tert-butyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OC(C)(C)C CVAWKJKISIPBOD-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (55)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB14916/76A GB1576625A (en) | 1976-04-12 | 1976-04-12 | Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof |
JP51125826A JPS5941995B2 (ja) | 1976-04-12 | 1976-10-19 | 3,7−ジ置換−3−セフエム−4−カルボン酸化合物およびその塩類およびそれらの製造方法 |
US05/767,700 US4166115A (en) | 1976-04-12 | 1977-02-11 | Syn 7-oxoimino substituted derivatives of cephalosporanic acid |
DK075077A DK162391C (da) | 1976-04-12 | 1977-02-21 | Analogifremgangsmaade til fremstilling af syn-isomerer af 3,7-disubstituerede 3-cephem-4-carboxylsyreforbindelser |
ZA00771059A ZA771059B (en) | 1976-04-12 | 1977-02-22 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
SE7701964A SE443981B (sv) | 1976-04-12 | 1977-02-22 | Analogiforfarande for framstellning av syn-isomerer av 3,7 disubstituerade 3-cefem-4-karboxylsyraforeningar |
DE19772707565 DE2707565A1 (de) | 1976-04-12 | 1977-02-22 | Syn-isomere von 3,7-disubstituierten-3-cephem-4-carbonsaeureverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
CA000272430A CA1337522C (en) | 1976-04-12 | 1977-02-23 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
CH244777A CH638532A5 (de) | 1976-04-12 | 1977-02-25 | Verfahren zur herstellung der syn-isomere von 3,7-disubstituierten 3-cephem-4-carbonsaeuren. |
HU77FU362A HU183009B (en) | 1976-04-12 | 1977-02-28 | Process for producing 2-oximino-acetic acid derivatives substituted with thiazolyl-4-ring at the 2 position |
HU77FU348A HU177441B (en) | 1976-04-12 | 1977-02-28 | Process for preparing syn isomers of 3,7-disubstituted 3-cephem-4-carboxylic acid derivatives |
IE2634/80A IE45598B1 (en) | 1976-04-12 | 1977-03-01 | Intermediates in the preparation of syn-isomers of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
IE440/77A IE45597B1 (en) | 1976-04-12 | 1977-03-01 | Syn isomer of 3,7-disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof |
AT138477A AT358728B (de) | 1976-04-12 | 1977-03-02 | Verfahren zur herstellung von neuen synisomeren von 3,7-disubstituierten 3-cephem-4-carbon- saeureverbindungen |
FR7707173A FR2348219A1 (fr) | 1976-04-12 | 1977-03-10 | Procede de preparation d'isomeres syn de composes d'acides 3,7-cephem-4-carboxyliques 3,7-disubstitues et nouveaux produits ainsi obtenus, a activite antibacterienne |
BE175758A BE852427A (fr) | 1976-04-12 | 1977-03-14 | Procede de preparation d'isomeres syn de composes d'acides 3,7-cephem-4-carboxyliques 3,7-disubstitues et nouveaux produits ainsi obtenus |
ES457191A ES457191A1 (es) | 1976-04-12 | 1977-03-25 | Un procedimiento para preparar el isomero sin de los com- puestos del acido 3-cefem-4-carboxilico sustituido en las posiciones 3 y 7. |
MX775624U MX4985E (es) | 1976-04-12 | 1977-04-11 | Procedimiento para preparar el isomero,sin del acido 3-cefem 4-carboxilico disubstituido en las posiciones 3 y 7 |
MX8561A MX155110A (es) | 1976-04-12 | 1977-04-11 | Procedimiento para preparar un intermedio para la obtencion del isomero sin del acido 3-cefem-4-carboxilico disubstituido en las posiciones 3 y 7 |
NL7703969A NL191259C (nl) | 1976-04-12 | 1977-04-12 | Werkwijze ter bereiding van een geneesmiddel met antibacteriële werking, alsmede werkwijze voor het bereiden van de syn-isomeer van een 7-[2-gesubstitueerd-2-(veretherd oxyimino)aceetamido]-3-(gesubstitueerd methyl)-3-cefem-4-carbonzuurderivaat. |
KR7700883A KR840000141B1 (ko) | 1976-04-12 | 1977-04-12 | 3, 7-디서브스티튜티드-3-세펨-4-카르복실산화합물의 신(syn) 이성체의 제조방법 |
AR257178A AR227864A1 (es) | 1976-04-12 | 1977-04-20 | Procedimiento para obtener isomeros syn de compuestos del acido 3-cefem-4-carboxilicos 3,7 disustituidos |
JP8249077A JPS5368796A (en) | 1976-04-12 | 1977-07-08 | Syn-isomer of 3,7-disubstd.-3-cephem-4-carboxylic acids, and their preventingor treating agents containing their salts as active constituent againstdiseases caused by bacterial infection |
JP8248977A JPS5368795A (en) | 1976-04-12 | 1977-07-08 | Syn-isomer of 7-substd.-3-methyl-3-cephem-4-carboxylic acids, their salts,and their preparation |
FR7802762A FR2367756B1 (fr) | 1976-04-12 | 1978-02-01 | Derives 2-alcoxyamino-2-(amino-1,3-thiazolyl) acetiques et leur utilisation |
US05/883,395 US4544653A (en) | 1976-04-12 | 1978-03-06 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
US05/887,999 US4279818A (en) | 1976-04-12 | 1978-03-20 | Syn-isomers of 7-[2-alkoxyimino-2-(2-amino-thiazol-4-yl)acetamido]-3-[nitrobenzoyl-, or benzoyl-oxymethyl]-3-cephem-4-carboxylic acid |
AR271541A AR223143A1 (es) | 1976-04-12 | 1978-03-27 | Un procedimiento para preparar el isomero sin de los compuestos del acido 3-cefem-4-carboxilico sustituido en las posiciones 3 y 7 |
ES468719A ES468719A1 (es) | 1976-04-12 | 1978-04-12 | Un procedimiento para preparar el isomero sin de los com- puestos del acido 3-cefem-4-carboxilico sustituido en las posiciones 3 y 7. |
US05/916,952 US4316019A (en) | 1976-04-12 | 1978-06-19 | Preparation of syn-isomer of 3-alkanoyloxymethyl-7-(2-alkoxyimino-2-thiazolylacetamido-3-cephem-4-carboxylic acid compounds |
ES477741A ES477741A1 (es) | 1976-04-12 | 1979-02-15 | Un procedimiento para preparar derivados de acido acetico. |
US06/040,976 US4877873A (en) | 1976-04-02 | 1979-05-21 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
US06/077,557 US4304770A (en) | 1976-04-12 | 1979-09-21 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
ES485064A ES485064A1 (es) | 1976-04-12 | 1979-10-16 | Un procedimiento para preparar derivados de acido acetico |
ES485061A ES485061A1 (es) | 1976-04-12 | 1979-10-16 | Un procedimiento para preparar el siomero sin descompuestos de acido 3-cefem-4-carboxilico sustituido en las posiciones 3 y 7 |
ES485062A ES485062A1 (es) | 1976-04-12 | 1979-10-16 | Un procedimiento para preparar derivados de acido acetico |
ES485063A ES485063A1 (es) | 1976-04-12 | 1979-10-16 | Un procedimiento para preparar derivados de acido acetico |
AT0677379A AT372375B (de) | 1976-04-12 | 1979-10-17 | Verfahren zur herstellung von neuen 1,3-thiazol- verbindungen und von deren salzen |
AT0677579A AT372377B (de) | 1976-04-12 | 1979-10-17 | Verfahren zur herstellung von neuen 1,3-thiazol- verbindungen und von deren salzen |
JP15697479A JPS5598189A (en) | 1976-04-12 | 1979-12-03 | Syn-isomer of 3, 7-di-substituted-3-cephem-4-carboxylic acid compound, its salt, and their preparation |
US06/123,164 US4331664A (en) | 1976-04-12 | 1980-02-20 | Syn isomer of 7-[2-cyclo(lower) alkoxyimino-2-(2-amino-or substituted aminothiazol-4-yl)acetamido]-3-lower alkanoyloxymethyl or heterocyclicthiomethyl-3-cephem-4-carboxylic acid compounds |
US06/240,221 US4364943A (en) | 1976-04-12 | 1981-03-03 | Syn-isomer of 7-[2-alkoxyimino-2-(2-amino-alkanoylamino-or haloalkanoylamino-thiazol-4-yl) acetamids]-3-[hexanoyl-, or phenylalkanoyl-oxymethyl or benzothiazolylthiomethyl]-3-cephem-4-carboxylic acid |
US06/296,117 US4493833A (en) | 1976-04-12 | 1981-08-25 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds |
KR1019810003622A KR840000142B1 (ko) | 1976-04-12 | 1981-09-28 | 3,7-이치환-3-세펨-4-카르복실산화합물의 syn-이성체의 제조방법 |
US06/353,879 US4431643A (en) | 1976-04-12 | 1982-03-01 | Syn-isomer of 3-substituted-7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)-acetamido]-3 |
JP58128676A JPS5962597A (ja) | 1976-04-12 | 1983-07-13 | 3,7−ジ置換−3−セフエム−4−カルボン酸化合物のシン異性体およびその塩類およびそれらを製造する方法 |
CH409583A CH643557A5 (en) | 1976-04-12 | 1983-07-26 | Process for the preparation of syn isomers of 3,7-disubstituted 3-cephem-4-carboxylic acids |
CH409883A CH643836A5 (de) | 1976-04-12 | 1983-07-26 | Verfahren zur herstellung der syn-isomeren von 2-oxyiminoessigsaeuren. |
CH409783A CH643823A5 (de) | 1976-04-12 | 1983-07-26 | Verfahren zur herstellung der syn-isomeren von 2-oxyiminoessigsaeuren. |
CH409683A CH643822A5 (de) | 1976-04-12 | 1983-07-26 | Verfahren zur herstellung der syn-isomeren von 2-oxyiminoessigsaeuren. |
SE8304465A SE457351B (sv) | 1976-04-12 | 1983-08-17 | Tiazolderivat till anvaendning som mellanprodukt foer framstaellning av 3,7 disubstituerade 3-cefem-4-karboxylsyrafoereningar samt foerfarande foer framstaellning daerav |
US06/525,499 US4804752A (en) | 1976-04-12 | 1983-08-22 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
US06/615,721 US4871860A (en) | 1976-04-12 | 1984-05-31 | Syn-isomer of 3,7-disubstituted-3-cephem-4-caroxylic acid compounds and processes for the preparation thereof |
US07/370,873 US5079369A (en) | 1976-04-12 | 1989-06-23 | Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof |
JP2261173A JPH0684338B2 (ja) | 1976-04-12 | 1990-09-28 | 置換酢酸誘導体 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB14916/76A GB1576625A (en) | 1976-04-12 | 1976-04-12 | Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof |
GB2349076 | 1976-06-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1576625A true GB1576625A (en) | 1980-10-08 |
Family
ID=26250890
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB14916/76A Expired GB1576625A (en) | 1976-04-02 | 1976-04-12 | Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof |
Country Status (3)
Country | Link |
---|---|
JP (6) | JPS5941995B2 (enrdf_load_stackoverflow) |
GB (1) | GB1576625A (enrdf_load_stackoverflow) |
HU (1) | HU183009B (enrdf_load_stackoverflow) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2188046A (en) * | 1985-05-30 | 1987-09-23 | Shionogi & Co | Hydroxymethylcephem compounds and their preparation |
US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US4866055A (en) * | 1986-11-25 | 1989-09-12 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives and their crystalline derivatives |
US4880798A (en) * | 1986-11-25 | 1989-11-14 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US4888332A (en) * | 1983-12-29 | 1989-12-19 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US5064953A (en) * | 1983-12-29 | 1991-11-12 | Mochida Pharmaceutical Co., Ltd. | Intermediates cephalosporin derivatives |
US5189157A (en) * | 1987-06-16 | 1993-02-23 | Hoffmann La Roche Inc. | Antibacterial cephalosporin compounds |
EP0832893A1 (en) * | 1996-09-25 | 1998-04-01 | Eisai Chemical Co., Ltd. | Process for the production of cephem compounds |
CN112480024A (zh) * | 2020-12-11 | 2021-03-12 | 山东金城医药化工有限公司 | 生产氨噻肟酸反式异构体的方法 |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE878433A (fr) * | 1978-08-31 | 1980-02-25 | Fujisawa Pharmaceutical Co | Procede de preparation de derives d'acide 3-cephem-4-carboxylique 3,7-disubstitue, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
BE878514A (fr) * | 1978-09-04 | 1980-02-29 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3-cephem-4-carboxylique a disubstitution en positions 3 et 7, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
SE439312B (sv) * | 1977-03-25 | 1985-06-10 | Roussel Uclaf | Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra |
DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
NL7805715A (nl) * | 1977-06-03 | 1978-12-05 | Hoffmann La Roche | Werkwijze voor het bereiden van acylderivaten. |
FR2410655A1 (fr) * | 1977-12-05 | 1979-06-29 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
JPS5498795A (en) * | 1978-01-13 | 1979-08-03 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
JPS54128594A (en) * | 1978-03-27 | 1979-10-05 | Fujisawa Pharmaceut Co Ltd | 3,7-disubstituted-3-cephem-4-carboxylic acid derivative |
FR2432521A1 (fr) * | 1978-03-31 | 1980-02-29 | Roussel Uclaf | Nouvelles oximes o-substituees derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
FR2421907A1 (fr) * | 1978-04-07 | 1979-11-02 | Roussel Uclaf | Nouvelles cephalosporines derivees de l'acide 7-/2-(2-amino 4-thiazolyl)2-(carboxymethoxyimino/acetamido 3-substitue cephalosporanique, leur procede de preparation et leur application comme medicaments |
GB1604722A (en) * | 1978-05-26 | 1981-12-16 | Glaxo Operations Ltd | 7-(2-(2-amino-4-thiozolyl)-2-oxymino-acetamido)-cephem derivatives |
GB1604723A (en) * | 1978-05-26 | 1981-12-16 | Glaxo Operations Ltd | 7-(2-aminothiazol-4-yl)-2-oxyimino-acetamido)-cephem derivatives |
EP0009548B1 (en) * | 1978-07-17 | 1985-01-16 | Fujisawa Pharmaceutical Co., Ltd. | Cephalosporin derivatives, process for their preparation and pharmaceutical compositions containing them |
US4703046A (en) * | 1978-09-08 | 1987-10-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds and processes for preparation thereof |
BE878637A (fr) * | 1978-09-11 | 1980-03-06 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3-cephem-4-carboxylique 3,7-disubstitue et de leurs sels pharmaceutiquement acceptables, nouveaux produits ainsi obtenus et leur utilisation pour leurs activites antimicrobiennes |
JPH02111750A (ja) * | 1978-09-12 | 1990-04-24 | Fujisawa Pharmaceut Co Ltd | 酪酸誘導体 |
JPS5585594A (en) * | 1978-11-13 | 1980-06-27 | Fujisawa Pharmaceut Co Ltd | Cephem compound and their preparation |
JPS5579393A (en) * | 1978-12-11 | 1980-06-14 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
JPS5616490A (en) * | 1979-07-18 | 1981-02-17 | Hoechst Ag | Cephem compound manufacture |
IL61458A0 (en) * | 1979-12-07 | 1980-12-31 | Erba Farmitalia | N-substituted thiazolyl derivatives of oximino-substituted cephalosporins, their preparation and pharmalceutical compositions containing them |
DE3165922D1 (en) * | 1980-03-28 | 1984-10-18 | Biochemie Gmbh | New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production |
IL63207A (en) * | 1980-07-24 | 1985-09-29 | Lonza Ag | Process for the preparation of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyiminoacetic acid esters |
JPS57154175A (en) * | 1981-03-16 | 1982-09-22 | Mitsui Toatsu Chem Inc | 2-thiazoleamine derivative, its preparation, and drug composition comprising it |
JPS57157594U (enrdf_load_stackoverflow) * | 1981-03-31 | 1982-10-04 | ||
EP0115770B2 (en) * | 1983-01-07 | 1996-06-19 | Takeda Chemical Industries, Ltd. | Thiazole Derivatives |
WO1984004305A1 (en) * | 1983-05-02 | 1984-11-08 | Takeda Chemical Industries Ltd | Process for preparing aminothiazoleacetic acid derivatives |
WO1984002703A1 (en) * | 1983-01-07 | 1984-07-19 | Takeda Chemical Industries Ltd | Process for preparing aminothiazolylacetic acid derivatives |
GB8318846D0 (en) * | 1983-07-12 | 1983-08-10 | Fujisawa Pharmaceutical Co | Prophylactic/therapeutic agent against fish diseases |
JPS60178891A (ja) * | 1984-02-24 | 1985-09-12 | Kureha Chem Ind Co Ltd | セファロスポリン誘導体及び該誘導体を含有する医薬 |
JPS60155167A (ja) * | 1984-07-31 | 1985-08-15 | Fujisawa Pharmaceut Co Ltd | 置換イミノ酢酸誘導体およびその塩類 |
JPS6236386A (ja) * | 1985-08-09 | 1987-02-17 | Kureha Chem Ind Co Ltd | セフアロスポリン誘導体、その製造方法及び該誘導体を含有する医薬 |
JPS6332235A (ja) * | 1986-07-25 | 1988-02-10 | アトラス・エア・(オ−ストラリア)・ピ−テイ−ワイ・リミテツド | 区域空調方法及びその装置 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1445979A (en) * | 1972-10-25 | 1976-08-11 | Glaxo Lab Ltd | Cephalosporin derivatives |
GB1453049A (en) * | 1973-08-21 | 1976-10-20 | Glaxo Lab Ltd | Cephalosporing antibiotics |
JPS4849789A (enrdf_load_stackoverflow) * | 1971-10-25 | 1973-07-13 | ||
JPS50111093A (enrdf_load_stackoverflow) * | 1974-02-20 | 1975-09-01 | ||
GB1536281A (en) * | 1975-06-09 | 1978-12-20 | Takeda Chemical Industries Ltd | Cephem compounds |
SE440655B (sv) * | 1976-01-23 | 1985-08-12 | Roussel Uclaf | Sett att framstella nya oximderivat av 7-amino-tiazolyl-acetamido-cefalosporansyra |
FR2345153A1 (fr) * | 1976-03-25 | 1977-10-21 | Roussel Uclaf | Nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
-
1976
- 1976-04-12 GB GB14916/76A patent/GB1576625A/en not_active Expired
- 1976-10-19 JP JP51125826A patent/JPS5941995B2/ja not_active Expired
-
1977
- 1977-02-28 HU HU77FU362A patent/HU183009B/hu unknown
- 1977-07-08 JP JP8249077A patent/JPS5368796A/ja active Granted
- 1977-07-08 JP JP8248977A patent/JPS5368795A/ja active Pending
-
1979
- 1979-12-03 JP JP15697479A patent/JPS5598189A/ja active Granted
-
1983
- 1983-07-13 JP JP58128676A patent/JPS5962597A/ja active Granted
-
1990
- 1990-09-28 JP JP2261173A patent/JPH0684338B2/ja not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4888332A (en) * | 1983-12-29 | 1989-12-19 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US5064953A (en) * | 1983-12-29 | 1991-11-12 | Mochida Pharmaceutical Co., Ltd. | Intermediates cephalosporin derivatives |
US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US4904791A (en) * | 1985-04-01 | 1990-02-27 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US4956474A (en) * | 1985-04-01 | 1990-09-11 | Mochida Pharmaceutical Co., Ltd. | Intermediates of cephalosporin compounds |
GB2188046A (en) * | 1985-05-30 | 1987-09-23 | Shionogi & Co | Hydroxymethylcephem compounds and their preparation |
US4866055A (en) * | 1986-11-25 | 1989-09-12 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives and their crystalline derivatives |
US4880798A (en) * | 1986-11-25 | 1989-11-14 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US5189157A (en) * | 1987-06-16 | 1993-02-23 | Hoffmann La Roche Inc. | Antibacterial cephalosporin compounds |
EP0832893A1 (en) * | 1996-09-25 | 1998-04-01 | Eisai Chemical Co., Ltd. | Process for the production of cephem compounds |
CN112480024A (zh) * | 2020-12-11 | 2021-03-12 | 山东金城医药化工有限公司 | 生产氨噻肟酸反式异构体的方法 |
Also Published As
Publication number | Publication date |
---|---|
JPS6137250B2 (enrdf_load_stackoverflow) | 1986-08-22 |
JPS5962597A (ja) | 1984-04-10 |
JPS5598189A (en) | 1980-07-25 |
JPS52125190A (en) | 1977-10-20 |
JPS6141516B2 (enrdf_load_stackoverflow) | 1986-09-16 |
JPH0684338B2 (ja) | 1994-10-26 |
JPS5941995B2 (ja) | 1984-10-11 |
JPH03135946A (ja) | 1991-06-10 |
JPS5368796A (en) | 1978-06-19 |
JPH0373553B2 (enrdf_load_stackoverflow) | 1991-11-22 |
JPS5368795A (en) | 1978-06-19 |
HU183009B (en) | 1984-04-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19970208 |