CS195680B2 - Process for preparing derivatives of 7-/substituted phenylglycinamido/-3-substituted-3-cephem-4-carboxylic acid - Google Patents

Process for preparing derivatives of 7-/substituted phenylglycinamido/-3-substituted-3-cephem-4-carboxylic acid Download PDF

Info

Publication number: CS195680B2
Authority: CS; Czechoslovakia
Prior art keywords: solution; compound; substituted; cephem; ethyl acetate
Prior art date: 1973-05-10

Application number

CS743339A

Other languages

Czech (cs)

English (en)

Inventor

Takashi Kamiya

Kunihiko Tanaka

Yoshihisa Saito

Teiji Kishimoto

Hisatoyo Yazawa

Tsutomu Teraji

Keiji Takai

Yoshiharu Nakai

Original Assignee

Fujisawa Pharmaceutical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-05-10

Filing date

1974-05-08

Publication date

1980-02-29

1973-05-10 Priority claimed from JP5231273A external-priority patent/JPS49135989A/ja

1973-07-06 Priority claimed from JP48076785A external-priority patent/JPS5934715B2/ja

1974-02-07 Priority claimed from JP49016552A external-priority patent/JPS5857438B2/ja

1974-02-08 Priority claimed from JP1655074A external-priority patent/JPS5716116B2/ja

1974-05-08 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1977-07-27 Priority to CS774977A priority Critical patent/CS195681B2/cs

1980-02-29 Publication of CS195680B2 publication Critical patent/CS195680B2/cs

Links

-1 phenylglycinamido Chemical group 0.000 title claims description 80
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 33
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
231100000252 nontoxic Toxicity 0.000 claims abstract description 5
230000003000 nontoxic effect Effects 0.000 claims abstract description 5
150000001768 cations Chemical class 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 67
238000000034 method Methods 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
239000007795 chemical reaction product Substances 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000004149 thio group Chemical group *S* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical class OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000004185 ester group Chemical group 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 21
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 8
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
229930186147 Cephalosporin Natural products 0.000 abstract description 2
229940124587 cephalosporin Drugs 0.000 abstract description 2
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
125000004468 heterocyclylthio group Chemical group 0.000 abstract 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
125000001589 carboacyl group Chemical group 0.000 abstract 1
150000001780 cephalosporins Chemical class 0.000 abstract 1
239000003085 diluting agent Substances 0.000 abstract 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
150000003573 thiols Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 240
239000000243 solution Substances 0.000 description 110
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 103
239000000203 mixture Substances 0.000 description 86
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
239000010410 layer Substances 0.000 description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
239000002253 acid Substances 0.000 description 28
238000005481 NMR spectroscopy Methods 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
238000001816 cooling Methods 0.000 description 26
239000002904 solvent Substances 0.000 description 26
239000000047 product Substances 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 21
235000019253 formic acid Nutrition 0.000 description 20
239000000843 powder Substances 0.000 description 20
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 19
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
238000000354 decomposition reaction Methods 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 16
239000000706 filtrate Substances 0.000 description 15
239000013078 crystal Substances 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
229960000583 acetic acid Drugs 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
239000000284 extract Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
239000004471 Glycine Substances 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
238000005406 washing Methods 0.000 description 8
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
NVIAYEIXYQCDAN-HWZXHQHMSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000872 buffer Substances 0.000 description 4
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000002024 ethyl acetate extract Substances 0.000 description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000007787 solid Substances 0.000 description 4
SDMNLZJVXWONEY-LLVKDONJSA-N (2r)-2-[3-(methanesulfonamido)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)C1=CC=CC(NS(C)(=O)=O)=C1 SDMNLZJVXWONEY-LLVKDONJSA-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 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 3
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
150000005331 phenylglycines Chemical class 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 description 2
VVROHPDPNYEIKD-JLHJGDBNSA-N 2,2,2-trichloroethyl (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride Chemical compound Cl.S1CC(C)=C(C(=O)OCC(Cl)(Cl)Cl)N2C(=O)C(N)[C@@H]12 VVROHPDPNYEIKD-JLHJGDBNSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
239000008272 agar Substances 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
244000005700 microbiome Species 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
235000011837 pasties Nutrition 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
URLVTQBXNZMMBN-LLVKDONJSA-N (2R)-2-[3-(methylcarbamothioylamino)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CNC(=S)NC1=CC=CC(=C1)[C@@H](NC(=O)OC(C)(C)C)C(O)=O URLVTQBXNZMMBN-LLVKDONJSA-N 0.000 description 1
APIPQYWFSQKATH-LLVKDONJSA-N (2R)-2-[3-(methylcarbamoylamino)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound C(C)(C)(C)OC(=O)N[C@@H](C(=O)O)C1=CC(=CC=C1)NC(=O)NC APIPQYWFSQKATH-LLVKDONJSA-N 0.000 description 1
SCDCKPMPGFECHB-LLVKDONJSA-N (2R)-2-[4-hydroxy-3-(methanesulfonamido)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)C1=CC(NS(C)(=O)=O)=C(O)C=C1 SCDCKPMPGFECHB-LLVKDONJSA-N 0.000 description 1
OFKRKCHCYWQZLY-DLTQXHKRSA-N (6R)-7-[[(2R)-2-amino-2-[3-(methanesulfonamido)phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S(=O)(=O)(C)NC=1C=C(C=CC=1)[C@@H](N)C(=O)NC1[C@@H]2N(C(=C(CS2)C)C(=O)O)C1=O OFKRKCHCYWQZLY-DLTQXHKRSA-N 0.000 description 1
FZDRVLJSDYQRPO-HWZXHQHMSA-N (6r)-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2CC(=O)N21 FZDRVLJSDYQRPO-HWZXHQHMSA-N 0.000 description 1
YZLSXKIVGNQGPR-UHFFFAOYSA-N 1,2-oxazole;hydrate Chemical compound O.C=1C=NOC=1 YZLSXKIVGNQGPR-UHFFFAOYSA-N 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 1
PVUUUZGQAPDABO-XCGJVMPOSA-N 2,2,2-trichloroethyl (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC(C)=C(C(=O)OCC(Cl)(Cl)Cl)N2C(=O)C(N)[C@@H]12 PVUUUZGQAPDABO-XCGJVMPOSA-N 0.000 description 1
RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
DWKNOLCXIFYNFV-HSZRJFAPSA-N 2-[[(2r)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-n,n,6-trimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NC(NC(=O)[C@@H]2N(C(=O)CC2)C2CCN(CC=3C=C(C)C(Cl)=CC=3)CC2)=C1 DWKNOLCXIFYNFV-HSZRJFAPSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
CTYJGUDXWIAZCM-UHFFFAOYSA-N 2-ethyl-3h-1,2-benzoxazol-7-ol Chemical class C1=CC(O)=C2ON(CC)CC2=C1 CTYJGUDXWIAZCM-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
241000208140 Acer Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
229920000388 Polyphosphate Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
101150046432 Tril gene Proteins 0.000 description 1
125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
238000011482 antibacterial activity assay Methods 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001951 carbamoylamino group Chemical class C(N)(=O)N* 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
239000006179 pH buffering agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 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
150000003536 tetrazoles Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000000080 wetting agent Substances 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
- 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
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
- 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)

CS743339A 1973-05-10 1974-05-08 Process for preparing derivatives of 7-/substituted phenylglycinamido/-3-substituted-3-cephem-4-carboxylic acid CS195680B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS774977A CS195681B2 (cs)	1974-05-08	1977-07-27	Způsob přípravy derivátů 7-[substituovaný fenylglycinamido ]-3- . -8ub8tituovaný-3 ceřein-4-karboxylové kyseliny

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP5231273A JPS49135989A (es)	1973-05-10	1973-05-10
JP48076785A JPS5934715B2 (ja)	1973-07-06	1973-07-06	７−置換アシルアミノ−３−置換−３−セフエム−４−カルボン酸類の製造法
JP49016552A JPS5857438B2 (ja)	1974-02-07	1974-02-07	７− ジチカンフエニルグリシンアミド −ルカメチル −３− セフエム −４− カルボンサンユウドウタイノセイゾウホウ
JP1655074A JPS5716116B2 (es)	1974-02-08	1974-02-08

Publications (1)

Publication Number	Publication Date
CS195680B2 true CS195680B2 (en)	1980-02-29

Family

ID=27456595

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS743339A CS195680B2 (en)	1973-05-10	1974-05-08	Process for preparing derivatives of 7-/substituted phenylglycinamido/-3-substituted-3-cephem-4-carboxylic acid

Country Status (14)

Country	Link
AR (2)	AR205537A1 (es)
AU (1)	AU499409B2 (es)
BE (1)	BE814727A (es)
CH (1)	CH603667A5 (es)
CS (1)	CS195680B2 (es)
DD (1)	DD111683A5 (es)
DE (1)	DE2422385C2 (es)
FR (1)	FR2228476B1 (es)
GB (1)	GB1473672A (es)
HU (1)	HU172016B (es)
IE (1)	IE39968B1 (es)
NL (1)	NL7406319A (es)
SE (2)	SE421128B (es)
SU (1)	SU608478A3 (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4007173A (en) *	1973-05-07	1977-02-08	Smithkline Corporation	α-amino-α-(ureidophenyl)acetamidocephalosporins
IL48090A0 (en) *	1974-09-19	1975-11-25	Merck Patent Gmbh	Cephem derivatives,their preparation and compositions containing them
CH622802A5 (es) *	1975-08-20	1981-04-30	Ciba Geigy Ag
DE2861767D1 (en) *	1977-07-18	1982-06-09	Ciba Geigy Ag	Cephalosprin derivatives, process for their preparation and pharmaceutical compositions containing them
US4409215A (en)	1979-11-19	1983-10-11	Fujisawa Pharmaceutical Co., Ltd.	7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3507861A (en) *	1966-09-14	1970-04-21	Lilly Co Eli	Certain 3-methyl-cephalosporin compounds
US3489750A (en) *	1967-09-05	1970-01-13	Bristol Myers Co	7-amino-cephalosporanic and decephalosporanic acid derivatives
US3641021A (en) *	1969-04-18	1972-02-08	Lilly Co Eli	3 7-(ring-substituted) cephalosporin compounds
IL38099A (en) *	1970-12-17	1976-01-30	Smith Kline French Lab	3-heterocyclyl thiomethylcephalosporins

1974
- 1974-01-01 AR AR253682A patent/AR205537A1/es active
- 1974-05-06 AU AU68654/74A patent/AU499409B2/en not_active Expired
- 1974-05-07 CH CH618874A patent/CH603667A5/xx not_active IP Right Cessation
- 1974-05-08 CS CS743339A patent/CS195680B2/cs unknown
- 1974-05-08 SU SU742028801A patent/SU608478A3/ru active
- 1974-05-08 BE BE144069A patent/BE814727A/xx unknown
- 1974-05-09 IE IE979/74A patent/IE39968B1/xx unknown
- 1974-05-09 HU HU74FU00000327A patent/HU172016B/hu unknown
- 1974-05-09 DE DE2422385A patent/DE2422385C2/de not_active Expired
- 1974-05-09 DD DD178389A patent/DD111683A5/xx unknown
- 1974-05-09 GB GB2063774A patent/GB1473672A/en not_active Expired
- 1974-05-09 FR FR7416107A patent/FR2228476B1/fr not_active Expired
- 1974-05-09 SE SE7406237A patent/SE421128B/xx unknown
- 1974-05-10 NL NL7406319A patent/NL7406319A/xx not_active Application Discontinuation
1975
- 1975-01-01 AR AR258488D patent/AR204577A1/es active
1978
- 1978-10-03 SE SE7810360A patent/SE7810360L/xx unknown

Also Published As

Publication number	Publication date
SE7810360L (sv)	1978-10-03
AU6865474A (en)	1975-11-06
CH603667A5 (es)	1978-08-31
DD111683A5 (es)	1975-03-05
IE39968B1 (en)	1979-02-14
FR2228476A1 (es)	1974-12-06
GB1473672A (en)	1977-05-18
AU499409B2 (en)	1979-04-12
FR2228476B1 (es)	1977-07-08
NL7406319A (es)	1974-11-12
SU608478A3 (ru)	1978-05-25
AR205537A1 (es)	1976-05-14
DE2422385A1 (de)	1974-11-28
SE421128B (sv)	1981-11-30
IE39968L (en)	1974-11-10
HU172016B (hu)	1978-05-28
AR204577A1 (es)	1976-02-12
BE814727A (fr)	1974-11-08
DE2422385C2 (de)	1983-04-28

Publication	Publication Date	Title
US4517361A (en)	1985-05-14	Cephalosporin derivatives
US4142046A (en)	1979-02-27	Intermediates for the preparation of 7-acyl-3-(substituted triazolylthiomethyl)cephalosporins
US4252952A (en)	1981-02-24	7-(α-Substituted glycinamido)-3-substituted methyl-3-cephem-4-carboxylic acids and their derivatives
US4382932A (en)	1983-05-10	Isoquinolinium substituted cephalosporins
US4286089A (en)	1981-08-25	7-Acyl-3-(substituted tetrazolyl thiomethyl)cephalosporins
US4263302A (en)	1981-04-21	Quinolinecarboxylic acid substituted penicillins and pharmaceutical compositions containing the same
CS195680B2 (en)	1980-02-29	Process for preparing derivatives of 7-/substituted phenylglycinamido/-3-substituted-3-cephem-4-carboxylic acid
US4388316A (en)	1983-06-14	Amino-substituted oxazole, oxadiazole and isoxazole-substituted cephalosporins
US4018921A (en)	1977-04-19	Substituted phenylglycylcephalosporins
US4131734A (en)	1978-12-26	7β-Acyloxy-3-heterocyclicthiomethyl cephalosporins
US4178444A (en)	1979-12-11	Hydrazono derivatives of cephalosporins
JPS6133825B2 (es)	1986-08-04
US3720664A (en)	1973-03-13	Alpha-ureidocyclohexadienylalkylene-penicillins
US4126682A (en)	1978-11-21	7-acyl-3-(carboxyalkyl and carbamoylalkyl substituted oxadiazolylthiomethyl) cephalosporins and antibacterial compositions and methods employing them
US3953439A (en)	1976-04-27	Substituted phenylglycylcephalosporins
US4005081A (en)	1977-01-25	3-Heterothiomethyl-7α-methoxy-7β-tetrazolylmethylthioacetamido-3-cephem derivatives
US4150224A (en)	1979-04-17	7[[(1-Pyrrollyl)7 acetyl]amino]cephalosporin derivatives
US4092480A (en)	1978-05-30	Intermediates for preparing substituted phenylglycylcephalosporins
US5585485A (en)	1996-12-17	Cephalosporin intermediate products
US4137314A (en)	1979-01-30	7-Dithioacetamido cephalosporins and pharmaceutical compositions and methods employing them having antibacterial activity
IE43376B1 (en)	1981-02-11	7-/ -amino-w-(3,4-methylenedioxyphenyl) acylamido/cephalosporanic acid derivatives
US4497811A (en)	1985-02-05	1-Oxadethiacephalosporin compound and antibacterial agent containing the _same
US4044047A (en)	1977-08-23	Intermediates for preparing substituted phenylglycylcephalosporins
GB1574791A (en)	1980-09-10	7-(a-cyanoalkylureido-acetamido)-cephalosporins
US4218564A (en)	1980-08-19	7β-Hydroxy-3-heterocyclicthio-methyl cephalosporin intermediates