HU182498B - Process for producing 7-bracket-iminoacetamido-bracket closed-3-thiomethyl-ceph-3-eme-4-caraoxylic acid - Google Patents

Process for producing 7-bracket-iminoacetamido-bracket closed-3-thiomethyl-ceph-3-eme-4-caraoxylic acid Download PDF

Info

Publication number: HU182498B
Authority: HU; Hungary
Prior art keywords: formula; methyl; compound; salts; compounds
Prior art date: 1977-06-03

Application number

HU78HO2077A

Other languages

English (en)

Hungarian (hu)

Inventor

Marc Montavon

Roland Reiner

Original Assignee

Hoffmann La Roche

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.)

1977-06-03

Filing date

1978-05-31

Publication date

1984-01-30

1978-05-31 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1984-01-30 Publication of HU182498B publication Critical patent/HU182498B/hu

Links

238000000034 method Methods 0.000 title claims description 27
239000002253 acid Substances 0.000 title claims description 24
150000001875 compounds Chemical class 0.000 claims abstract description 68
-1 aminocarbonylmethyl Chemical group 0.000 claims abstract description 58
150000003839 salts Chemical class 0.000 claims abstract description 52
150000004677 hydrates Chemical class 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000002541 furyl group Chemical group 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000001544 thienyl group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
238000002360 preparation method Methods 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
239000007858 starting material Substances 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 6
150000003573 thiols Chemical class 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 5
239000001257 hydrogen Substances 0.000 abstract description 5
229910052736 halogen Inorganic materials 0.000 abstract description 3
125000005843 halogen group Chemical group 0.000 abstract description 3
229930186147 Cephalosporin Natural products 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract description 2
229940124587 cephalosporin Drugs 0.000 abstract description 2
150000001780 cephalosporins Chemical class 0.000 abstract description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000047 product Substances 0.000 description 14
239000000243 solution Substances 0.000 description 13
125000000446 sulfanediyl group Chemical group *S* 0.000 description 13
159000000000 sodium salts Chemical class 0.000 description 12
239000000843 powder Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000006071 cream Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
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 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000606768 Haemophilus influenzae Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
241000588770 Proteus mirabilis Species 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
244000005700 microbiome Species 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
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 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PWYKZJJSLCPHSM-UHFFFAOYSA-N 2-methyl-1-sulfanyltriazinane-4,5-dione Chemical compound CN1N=C(O)C(=O)CN1S PWYKZJJSLCPHSM-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
MWOOKDULMBMMPN-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonate Chemical compound O1[N+](CC)=CC=C1C1=CC=CC(S([O-])(=O)=O)=C1 MWOOKDULMBMMPN-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
LZJMAYUYNZUEPC-UHFFFAOYSA-N CON=C1C=CC=CC1CC(O)=O Chemical compound CON=C1C=CC=CC1CC(O)=O LZJMAYUYNZUEPC-UHFFFAOYSA-N 0.000 description 1
QBRYVEBVCLYGEO-UHFFFAOYSA-N CON=C1OC=CC1CC(O)=O Chemical compound CON=C1OC=CC1CC(O)=O QBRYVEBVCLYGEO-UHFFFAOYSA-N 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
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 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
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125000002587 enol group Chemical group 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
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239000012467 final product Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
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150000007928 imidazolide derivatives Chemical class 0.000 description 1
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238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
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238000007918 intramuscular administration Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010410 layer Substances 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
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USSCYGYLFIOOIR-UHFFFAOYSA-N n'-(2-benzyl-3-phenylpropyl)ethane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(CNCCN)CC1=CC=CC=C1 USSCYGYLFIOOIR-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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239000008055 phosphate buffer solution Substances 0.000 description 1
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230000002265 prevention Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
238000012800 visualization Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

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

HU78HO2077A 1977-06-03 1978-05-31 Process for producing 7-bracket-iminoacetamido-bracket closed-3-thiomethyl-ceph-3-eme-4-caraoxylic acid HU182498B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU77485		1977-06-03
CH314278		1978-03-22

Publications (1)

Publication Number	Publication Date
HU182498B true HU182498B (en)	1984-01-30

Family

ID=25692293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU78HO2077A HU182498B (en)	1977-06-03	1978-05-31	Process for producing 7-bracket-iminoacetamido-bracket closed-3-thiomethyl-ceph-3-eme-4-caraoxylic acid

Country Status (26)

Country	Link
EP (1)	EP0000005B1 (de)
JP (1)	JPS5412394A (de)
AR (1)	AR225134A1 (de)
AT (2)	AT362501B (de)
AU (1)	AU518648B2 (de)
BR (1)	BR7803565A (de)
CA (1)	CA1114808A (de)
CU (1)	CU21118A (de)
DE (2)	DE2860248D1 (de)
DK (1)	DK246878A (de)
ES (2)	ES470442A1 (de)
FI (1)	FI781754A7 (de)
FR (1)	FR2393000A1 (de)
GB (1)	GB1599232A (de)
GR (1)	GR73554B (de)
HU (1)	HU182498B (de)
IE (1)	IE46903B1 (de)
IL (1)	IL54803A (de)
IT (1)	IT1098306B (de)
MC (1)	MC1195A1 (de)
NL (1)	NL7805715A (de)
NO (1)	NO781934L (de)
NZ (1)	NZ187392A (de)
PH (1)	PH14653A (de)
PT (1)	PT68134A (de)
SE (1)	SE7806465L (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4200745A (en) *	1977-12-20	1980-04-29	Eli Lilly And Company	7[2-(2-Aminothiazol-4-yl)-2-alkoxyimino]acetamido 3[4-alkyl-5-oxo-6-hydroxy-3,4 dihydro 1,2,4-triazin 3-yl]thio methyl cephalosporins
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
MC1259A1 (fr) *	1978-05-30	1980-01-14	Hoffmann La Roche	Derives acyles
FI782683A7 (fi) *	1978-07-19	1980-01-20	Hoffmann La Roche	Kefalosporinestrar och -estrar
US4472574A (en) *	1981-05-22	1984-09-18	Hoffman-La Roche Inc.	Process for the manufacture of a cephem carboxylic acid derivative
US4698338A (en) *	1986-02-19	1987-10-06	Eli Lilly And Company	7[2-(2-aminothiazol-4-yl)-2-benzyloximino]acetamido-3[4-alkyl-5-oxo-6-hydroxy-3,4-dihydro-1,2,4-triazin-3-yl]thiomethyl cephalosporins

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1399086A (en) *	1971-05-14	1975-06-25	Glaxo Lab Ltd	Cephalosporin compounds
CH609989A5 (en) *	1974-06-21	1979-03-30	Hoffmann La Roche	Process for the preparation of acyl derivatives
CA1100129A (en) *	1974-08-02	1981-04-28	William H.W. Lunn	Cephalosporin compounds
GB1555471A (en) *	1975-06-19	1979-11-14	Glaxo Lab Ltd	7 carbamoylalkoxyimino acetamido 3 em 4 carboxylic acidsand derivatives thereof
GB1576625A (en) *	1976-04-12	1980-10-08	Fujisawa Pharmaceutical Co	Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof
GB1596278A (en) *	1976-11-30	1981-08-26	Glaxo Operations Ltd	7-(-oxyimino-acetamino)cephalosporin derivatives

1978
- 1978-05-25 NL NL7805715A patent/NL7805715A/xx not_active Application Discontinuation
- 1978-05-25 GB GB22499/78A patent/GB1599232A/en not_active Expired
- 1978-05-26 IE IE1056/78A patent/IE46903B1/en unknown
- 1978-05-26 MC MC781305A patent/MC1195A1/fr unknown
- 1978-05-26 NZ NZ187392A patent/NZ187392A/en unknown
- 1978-05-29 AU AU36588/78A patent/AU518648B2/en not_active Expired
- 1978-05-29 IL IL54803A patent/IL54803A/xx unknown
- 1978-05-31 HU HU78HO2077A patent/HU182498B/hu unknown
- 1978-06-01 DE DE7878100078T patent/DE2860248D1/de not_active Expired
- 1978-06-01 JP JP6501078A patent/JPS5412394A/ja active Pending
- 1978-06-01 DE DE19782824065 patent/DE2824065A1/de not_active Withdrawn
- 1978-06-01 FR FR7816468A patent/FR2393000A1/fr active Granted
- 1978-06-01 SE SE7806465A patent/SE7806465L/xx unknown
- 1978-06-01 GR GR56409A patent/GR73554B/el unknown
- 1978-06-01 EP EP78100078A patent/EP0000005B1/de not_active Expired
- 1978-06-01 FI FI781754A patent/FI781754A7/fi not_active Application Discontinuation
- 1978-06-02 NO NO781934A patent/NO781934L/no unknown
- 1978-06-02 AT AT403578A patent/AT362501B/de not_active IP Right Cessation
- 1978-06-02 DK DK246878A patent/DK246878A/da not_active Application Discontinuation
- 1978-06-02 BR BR787803565A patent/BR7803565A/pt unknown
- 1978-06-02 PT PT68134A patent/PT68134A/pt unknown
- 1978-06-02 AR AR272437A patent/AR225134A1/es active
- 1978-06-02 PH PH21225A patent/PH14653A/en unknown
- 1978-06-02 ES ES470442A patent/ES470442A1/es not_active Expired
- 1978-06-02 IT IT24165/78A patent/IT1098306B/it active
- 1978-06-02 CA CA304,644A patent/CA1114808A/en not_active Expired
- 1978-07-03 CU CU7834929A patent/CU21118A/es unknown
1979
- 1979-02-27 ES ES478115A patent/ES478115A1/es not_active Expired
1980
- 1980-07-02 AT AT0345980A patent/AT365197B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT7824165A0 (it)	1978-06-02
SE7806465L (sv)	1978-12-04
ES470442A1 (es)	1979-10-01
DE2860248D1 (en)	1981-01-29
DK246878A (da)	1978-12-04
JPS5412394A (en)	1979-01-30
IT1098306B (it)	1985-09-07
IE781056L (en)	1978-12-03
MC1195A1 (fr)	1979-02-23
GR73554B (de)	1984-03-14
AT365197B (de)	1981-12-28
IL54803A (en)	1982-01-31
AR225134A1 (es)	1982-02-26
EP0000005B1 (de)	1980-10-29
EP0000005A1 (de)	1978-12-20
PH14653A (en)	1981-10-14
FI781754A7 (fi)	1978-12-04
IL54803A0 (en)	1978-07-31
FR2393000A1 (fr)	1978-12-29
DE2824065A1 (de)	1978-12-14
NZ187392A (en)	1984-05-31
CA1114808A (en)	1981-12-22
NL7805715A (nl)	1978-12-05
GB1599232A (en)	1981-09-30
ATA403578A (de)	1980-10-15
NO781934L (no)	1978-12-05
IE46903B1 (en)	1983-11-02
FR2393000B1 (de)	1982-10-29
ATA345980A (de)	1981-05-15
ES478115A1 (es)	1979-06-01
PT68134A (en)	1978-07-01
AU518648B2 (en)	1981-10-15
AU3658878A (en)	1979-12-06
BR7803565A (pt)	1979-02-20
CU21118A (es)	1983-04-06
AT362501B (de)	1981-05-25

Publication	Publication Date	Title
EP0134420B1 (de)	1986-12-10	Cephalosporinverbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Präparate
EP0360298A2 (de)	1990-03-28	Zwischenverbindungen für die Anwendung bei der Synthese von Cephalosporinderivaten
HU183089B (en)	1984-04-28	Process for preparing cef-3-em-4-carboxylic acid derivatives
HU184941B (en)	1984-11-28	Process for producing acyl derivatives of cepheme-carboxylic acids
HU187812B (en)	1986-02-28	Process for the preparation of new pyridinium-thio-methyl-cephem-carboxilic acid derivatives
JPS6153359B2 (de)	1986-11-17
EP0264091B1 (de)	1992-02-05	3-Propenylcephemderivate, ihre Herstellung, Zwischenverbindungen, pharmazeutische Präparate und Anwendung
US4971962A (en)	1990-11-20	Cephalosporin compounds
HU185644B (en)	1985-03-28	Process for producing 7-beta-square bracket-alpha-syn-methoxy-imino-alpha-bracket-2-amino-thiazol-4-yl-bracket closed-acetamido-square bracket closed-3-bracket-1,2,3-thiazol-5-yl-thio-nethyl-aracket closed-3-cepheme-4-carboxylic acid derivatives
HU201948B (en)	1991-01-28	Process for producing cefemcarboxylic acid derivatives and pharmaceutical compositions comprising same
CA1114808A (en)	1981-12-22	Derivatives of 7-¬substituted oxyiminoacetamido\| cephalosporins
US4576938A (en)	1986-03-18	Cephalosporin compound and process for preparing the same
US4178443A (en)	1979-12-11	Derivatives of 7 [-substituted oxyimins acetamido] cephalosporins
KR100696422B1 (ko)	2007-03-20	항생물질로서 사이클릭 아미노구아니딘 치환체를 가진세팔로스포린
US3953439A (en)	1976-04-27	Substituted phenylglycylcephalosporins
US4179502A (en)	1979-12-18	7[2-Hydroxyiminoacetamido]cephalosporins
WO1997024359A1 (en)	1997-07-10	Novel cephalosporin derivatives and processes for the preparation thereof
CA1104560A (en)	1981-07-07	Pyrrole cephalosporin derivatives
US4107440A (en)	1978-08-15	Intermediates for preparing substituted phenylglycylcephalosporins
KR810000807B1 (ko)	1981-07-08	세팔로스포린 유도체의 제조방법
FI73442C (fi)	1987-10-09	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara (6r,7r)-7-/2-(2-amino-4-tiazolyl)-2- hydroxiimino)acetamido/-3-//(substituerad-as-triazin-3-yl)tio/metyl/ -8-oxo-5-tia-1-azabicyklo/4.2.0/okt-2-en-2-karboxylsyror.
US4044047A (en)	1977-08-23	Intermediates for preparing substituted phenylglycylcephalosporins
HU183012B (en)	1984-04-28	Process for producing esters and ethers of cepheme carboxylic acid
US4013764A (en)	1977-03-22	Pharmaceutical compositions comprising substituted phenylglycylcephalosporins and methods of treating bacterial infections
IE47929B1 (en)	1984-07-25	Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acids