SU495841A3 - Способ получени производных цефалоспорина - Google Patents

Способ получени производных цефалоспорина

Info

Publication number: SU495841A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acid; product; water; mixture; ether
Prior art date: 1968-06-27

Application number

SU1343897A

Other languages

English (en)

Russian (ru)

Inventor

Мартель Жак

Эймес Рене

Original Assignee

Руссель Уклаф (Фирма)

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.)

1968-06-27

Filing date

1969-06-25

Publication date

1975-12-15

1969-06-25 Application filed by Руссель Уклаф (Фирма) filed Critical Руссель Уклаф (Фирма)

1975-12-15 Application granted granted Critical

1975-12-15 Publication of SU495841A3 publication Critical patent/SU495841A3/ru

Links

238000000034 method Methods 0.000 title description 4
229930186147 Cephalosporin Natural products 0.000 title 1
229940124587 cephalosporin Drugs 0.000 title 1
150000001780 cephalosporins Chemical class 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000000047 product Substances 0.000 description 28
239000000203 mixture Substances 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
-1 halogen anion Chemical group 0.000 description 15
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
239000013078 crystal Substances 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000243 solution Substances 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
238000010992 reflux Methods 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RRUSUYOWPCRORE-UHFFFAOYSA-N 1-benzyl-4,5-dioxopyrrolidine-3-carboxylic acid Chemical compound O=C1C(=O)C(C(=O)O)CN1CC1=CC=CC=C1 RRUSUYOWPCRORE-UHFFFAOYSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
FUFQRORDJRHVLE-UHFFFAOYSA-N Cl.O=C1NCC(C1=O)CN1CCOCC1 Chemical compound Cl.O=C1NCC(C1=O)CN1CCOCC1 FUFQRORDJRHVLE-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
MITCVKYANSENJT-UHFFFAOYSA-N benzyl 4,5-dioxopyrrolidine-3-carboxylate Chemical compound O=C1NCC(C1=O)C(=O)OCC1=CC=CC=C1 MITCVKYANSENJT-UHFFFAOYSA-N 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000002085 enols Chemical group 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
229940099259 vaseline Drugs 0.000 description 2
VYLDBYOSHBXGNF-UHFFFAOYSA-N 2-oxo-2-phenylmethoxyacetic acid Chemical compound OC(=O)C(=O)OCC1=CC=CC=C1 VYLDBYOSHBXGNF-UHFFFAOYSA-N 0.000 description 1
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
RHFFIPXCSYYCFE-UHFFFAOYSA-N 4,5-dioxopyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1CNC(=O)C1=O RHFFIPXCSYYCFE-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
238000005452 bending Methods 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
QGFRSPMTVBPWNK-UHFFFAOYSA-N dilithium;oxygen(2-);hydrate Chemical compound [Li+].[Li+].O.[O-2] QGFRSPMTVBPWNK-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
240000004308 marijuana Species 0.000 description 1
239000000155 melt Substances 0.000 description 1
OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical compound [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
ATUHHCSHAHGVEM-UHFFFAOYSA-M potassium;benzyl sulfate Chemical compound [K+].[O-]S(=O)(=O)OCC1=CC=CC=C1 ATUHHCSHAHGVEM-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
235000011888 snacks Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005866 tritylation reaction Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Classifications

- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H9/00—Details of switching devices, not covered by groups H01H1/00 - H01H7/00
- H01H9/18—Distinguishing marks on switches, e.g. for indicating switch location in the dark; Adaptation of switches to receive distinguishing marks
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
- 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
- C07D501/02—Preparation
- C07D501/08—Preparation by forming the ring or condensed ring systems
- 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
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/42—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by an araliphatic carboxylic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V17/00—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages
- F21V17/10—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening
- F21V17/16—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening by deformation of parts; Snap action mounting
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H13/00—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch
- H01H13/50—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member
- H01H13/52—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member the contact returning to its original state immediately upon removal of operating force, e.g. bell-push switch

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Physics & Mathematics (AREA)
Theoretical Computer Science (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
General Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
General Physics & Mathematics (AREA)
Life Sciences & Earth Sciences (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU1343897A 1968-06-27 1969-06-25 Способ получени производных цефалоспорина SU495841A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR156898		1968-06-27

Publications (1)

Publication Number	Publication Date
SU495841A3 true SU495841A3 (ru)	1975-12-15

Family

ID=8651750

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU1343897A SU495841A3 (ru)	1968-06-27	1969-06-25	Способ получени производных цефалоспорина
SU1340776A SU384232A3 (pl)	1968-06-27	1969-06-25

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU1340776A SU384232A3 (pl)	1968-06-27	1969-06-25

Country Status (14)

Country	Link
JP (2)	JPS5028440B1 (pl)
AT (2)	AT293614B (pl)
BE (1)	BE735127A (pl)
BR (3)	BR6910250D0 (pl)
CH (3)	CH513206A (pl)
DE (4)	DE1967030C3 (pl)
ES (2)	ES368820A1 (pl)
FR (1)	FR1584569A (pl)
GB (5)	GB1271015A (pl)
HU (1)	HU162644B (pl)
IL (1)	IL32379A (pl)
NL (2)	NL142415B (pl)
PL (1)	PL79142B1 (pl)
SU (2)	SU495841A3 (pl)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EA013864B1 (ru) *	2008-08-29	2010-08-30	Лимонова, Анастасия Викторовна	Способ повышения антимикробной активности цефалоспориновых антибиотиков

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUT60607A (en) *	1986-08-19	1992-10-28	Horst Forschner	Method for producing wearing apparels carrying out by the user and set for producing such wearing apparels

1968
- 1968-06-27 FR FR156898A patent/FR1584569A/fr not_active Expired
1969
- 1969-06-11 IL IL32379A patent/IL32379A/en unknown
- 1969-06-13 PL PL1969134161A patent/PL79142B1/pl unknown
- 1969-06-24 CH CH968169A patent/CH513206A/fr not_active IP Right Cessation
- 1969-06-24 CH CH968069A patent/CH515276A/fr not_active IP Right Cessation
- 1969-06-24 CH CH14171A patent/CH522635A/fr not_active IP Right Cessation
- 1969-06-25 SU SU1343897A patent/SU495841A3/ru active
- 1969-06-25 SU SU1340776A patent/SU384232A3/ru active
- 1969-06-25 HU HURO582A patent/HU162644B/hu unknown
- 1969-06-25 BE BE735127D patent/BE735127A/xx unknown
- 1969-06-26 DE DE1967030A patent/DE1967030C3/de not_active Expired
- 1969-06-26 ES ES368820A patent/ES368820A1/es not_active Expired
- 1969-06-26 NL NL696909850A patent/NL142415B/xx not_active IP Right Cessation
- 1969-06-26 DE DE19691966204 patent/DE1966204A1/de active Pending
- 1969-06-26 DE DE19691932498 patent/DE1932498A1/de not_active Withdrawn
- 1969-06-26 NL NL696909849A patent/NL142691B/xx not_active IP Right Cessation
- 1969-06-26 DE DE1966203A patent/DE1966203C3/de not_active Expired
- 1969-06-27 GB GB47787/71A patent/GB1271015A/en not_active Expired
- 1969-06-27 GB GB47789/71A patent/GB1271017A/en not_active Expired
- 1969-06-27 GB GB47788/71A patent/GB1271016A/en not_active Expired
- 1969-06-27 JP JP44050289A patent/JPS5028440B1/ja active Pending
- 1969-06-27 AT AT618469A patent/AT293614B/de not_active IP Right Cessation
- 1969-06-27 GB GB47790/71A patent/GB1271018A/en not_active Expired
- 1969-06-27 BR BR210250/69A patent/BR6910250D0/pt unknown
- 1969-06-27 GB GB32567/69A patent/GB1271013A/en not_active Expired
- 1969-06-27 BR BR210252/69A patent/BR6910252D0/pt unknown
- 1969-06-27 AT AT618569A patent/AT293615B/de not_active IP Right Cessation
- 1969-06-27 BR BR210251/69A patent/BR6910251D0/pt unknown
- 1969-06-27 JP JP44050288A patent/JPS4934999B1/ja active Pending
1971
- 1971-09-17 ES ES395175A patent/ES395175A2/es not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EA013864B1 (ru) *	2008-08-29	2010-08-30	Лимонова, Анастасия Викторовна	Способ повышения антимикробной активности цефалоспориновых антибиотиков

Also Published As

Publication number	Publication date
ES395175A2 (es)	1974-01-16
DE1966203C3 (de)	1980-10-09
NL142691B (nl)	1974-07-15
GB1271017A (en)	1972-04-19
CH513206A (fr)	1971-09-30
FR1584569A (pl)	1969-12-26
DE1932504A1 (de)	1970-01-15
DE1932504B2 (de)	1977-03-17
DE1932498A1 (de)	1970-02-26
NL6909850A (pl)	1969-12-30
IL32379A0 (en)	1969-08-27
JPS5028440B1 (pl)	1975-09-16
BE735127A (pl)	1969-12-29
GB1271015A (en)	1972-04-19
CH522635A (fr)	1972-05-15
BR6910251D0 (pt)	1973-02-08
AT293615B (de)	1971-10-25
DE1967030B2 (de)	1977-11-24
DE1966204A1 (de)	1971-10-21
DE1967030C3 (de)	1978-08-03
BR6910250D0 (pt)	1973-02-08
NL6909849A (pl)	1969-12-30
BR6910252D0 (pt)	1973-02-08
CH515276A (fr)	1971-11-15
JPS4934999B1 (pl)	1974-09-19
GB1271016A (en)	1972-04-19
NL142415B (nl)	1974-06-17
AT293614B (de)	1971-10-25
DE1966203A1 (de)	1972-01-27
HU162644B (pl)	1973-03-28
GB1271018A (en)	1972-04-19
IL32379A (en)	1973-10-25
GB1271013A (en)	1972-04-19
DE1967030A1 (de)	1976-07-29
DE1966203B2 (de)	1980-02-07
PL79142B1 (en)	1975-06-30
SU384232A3 (pl)	1973-05-23
ES368820A1 (es)	1971-05-16

Publication	Publication Date	Title
SE452459B (sv)	1987-11-30	Indol-5-metansulfonamid, en farmaceutisk komposition och ett forfarande for framstellning av foreningen
PT2311805E (pt)	2012-07-18	Nova forma polimórfica de acetato de bazedoxifeno
JPH05247013A (ja)	1993-09-24	アミノチアゾリル酢酸の新規なオキシム誘導体及びその製造法
SU633471A3 (ru)	1978-11-15	Способ получени замещенных трихлорацетамидинов или их солей
SU495841A3 (ru)	1975-12-15	Способ получени производных цефалоспорина
JPS63239279A (ja)	1988-10-05	新規な置換テトラヒドロフラン誘導体
SU558644A3 (ru)	1977-05-15	Способ получени имидазолов или их солей
FI62066C (fi)	1982-11-10	Foerfarande foer framstaellning av antitrombotiska cyklohexylfenylderivat
US3299095A (en)	1967-01-17	1-benzyl tetramic acid derivatives
SU538662A3 (ru)	1976-12-05	Способ получени производных 2-бензоил-3-аминопиридина или их солей
EP0043756A1 (fr)	1982-01-13	1,2,4-Triazinylthiométhyl-3-céphèmes sulfoxydes, procédé de préparation et compositions pharmaceutiques en contenant
CH637918A5 (fr)	1983-08-31	Derives ioniques polyiodes du benzene, utilisables comme produits opacifiants pour la radiographie.
Karady et al.	1971	Synthesis of D-and L-. alpha.-(3, 4-dihydroxybenzyl)-. alpha.-hydrazinopropionic acid via resolution
SU1039444A3 (ru)	1983-08-30	Способ получени 1-оксадетиацефалоспоринов
DE2747573A1 (de)	1978-05-18	4-(3-amino-3-carboxypropoxy)phenylglyoxylsaeuren und verfahren zu ihrer herstellung
JPS58173102A (ja)	1983-10-12	エ−テル化サイクロデキストリンの単離精製法
RU2047603C1 (ru)	1995-11-10	1-алкил-2-ацилиндолы и способы их получения
SU650502A3 (ru)	1979-02-28	Способ получени 4-(4"-хлорбензилокси)-бензилникотината или его солей
HU198292B (en)	1989-09-28	Process for producing salicilates and pharmaceutical compositions comprising such active ingredient
US2571852A (en)	1951-10-16	Substituted amino analogs of pantothenic acid and process
SU436057A1 (ru)	1974-07-15	СПОСОБ ПОЛУЧЕНИЯ ИЗОПРОПИЛИДЕНОВЫХ ПРОИЗВОДНЫХ ПИРИДОКСИНАВ ПТ5ФОНЯ mmim
SU642308A1 (ru)	1979-01-15	Способ получени 0-бензоильного 6-хлорзамещенного 3-окиси-1,2,3, 4-тетрагидродензо / /хинолина или его 7-бромпроизводного
RU2108326C1 (ru)	1998-04-10	Способ получения 2-карбокси-3-[2-(диметиламино)этил]-n-метил-1h-индол-5-метансульфонамида или его сложных эфиров
FI56379C (fi)	1980-01-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 6-aza-3h-1,4-benzodiazepin-2-oner och deras salter
DE1932504C3 (de)	1977-10-27	Verfahren zur Herstellung racemischer oder optisch aktiver Cephalosporinderivate

SU495841A3 - Способ получени производных цефалоспорина - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=8651750

Family Applications (2)

Family Applications After (1)

Country Status (14)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

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