- ..
ISBN 978-5-9704-0578-9
( ):
Cefoperazon 62893-19-0 Antibioticum
(6R,7R)-7-[(K)-2-(4-ethyl-2,3-dioxo-l-piperazmecarboxamido)-2-(/»~hydroxyphenyl)acetamido]-3-[[(1-methyl-l#-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
170 С Cefoperazon
HjN
CH2-O-CO-CH3
COOH
7-Aminocephalosporansaure
5,5
N—N_
1-Methyl-1 W-1,2,3,4-tetrazol-5-thiol
H2N
cooh
H3C
/ гч CH2— S—(\ II M-N
7- Amino-3-[5-(1 -methyl-1,2,3,4-tetrazolyU-thiomethyl) -^3-cephem-
4-carbonsaure
(vgt. auch Cefamandol-Synthese, S. 166)
O-^^-CH-COONa
nh-c=ch-cooch3 ;omf/ch2c;2/ci-cooc2hs/-is* bis -ювс/н3с-Анэ
o-(-)-4-(Hydroxyphenyl)- Chlofameisen- A/,O-0is-(trimethyi-
glycin (DANE-Salz) saureethylester silyU-aeetamid
OH
7-[o-{-)-a-Amino-(4-hydroxyphenyl)-acet' amido ]-3-{5-n-methy}-J,2,3,4-tetrazolyl)-thiomethyl]- /43-cephem-6-car bonsaure
M /?
H5c2-N^_/К2СОз / 0 bis 5°C
2,3 - Oioxo - 4 - ethyl -1 -piperazin-carbonyl -chlorid (vgl. PiperaciHin-Synthese, S. 732)
0, ,0
H3C
H5C2-N N-C-NH-CH-C-NH-j—f' '"i
^ ’ 0^N-f^CH2-S4^
COOH N*^
OH
Cefoperazon
u
H5C2-N N-
H2N-CH-COONa
2,3-Oioxo-i-ethyl-l-
piperazin-carbonyl-
chlorid
0-M-4-(Hydroxy-
phenyl)-glycm
(Na-Salz
V4° Я
hsc2-n N-C-NH-CH-COOH
V_/
D-{-)-a-{213-Dioxo-i-ethyl-1-piperaztno-
carbonylamino)-4-hydroxyphenylesatg5aure
1. CH2Clj / DMF/A/^-Oimethylamlin / -15QC / Cl -COOC2Hs HH, H3C C-S|(CH3)3
/CH3CN/H3C-C / - 20 °C
4N —Si{CH3)3
-► Cefoperazon
1 Chlorameisersaureethylestsr
2. 7-Amino-3-|5-(1-methyl - A/,0-Bis-|tnmetnylaiyl)-1,2,3,4-tetrazotyl) - thio - aeetamrd
methyl ]-^3-cephem- 4-carbcnsaure
CH2-S-<4
Cefoperazon - Cefotaxim С 171
DOF 4, 675(1979)
USP 4110327 (Toyama; ert. 29.8.1978; J-Prior. 9.5.1974,13.5.1974, 31.5.1974,13.8.1974,26.9.1974,
13.12.1974, 27.3.1975).
DOS 2 519400 (Toyama; Anm. 30.4.1975; J-Prior. 9.5.1974,13.5,1974,31.5.1974,13.8.1974,
26.9.1974.13.12.1974.27.3.1975).
GB-P 1508062 (Toyama; Anm. 28.4.1975; J-Prior. 9.5.1974,13.5.1974, 31.5.1974,24.7.1974,
7.8.1974.13.8.1974, 26.9.1974,12.10.1974,28.10.1974, 6.12.1974,13.12.1974,17.2.1975,
26.3.1975.27.3.1975).
GB-P 1508 071 (Toyama; Anm. 19.1.1976). jV,N-Dimethylacetamid-Adduktc:
DOS 2 841 706 (Toyama; Anm. 25.9.1978; J-Prior. 27.9.1977).
J: Cefobid® (Toyama/Pfizer)
Cefotaxim
60846-23-3
Antibioticum
(6/J,7^)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid a-(0-methyloxime), acetate (ester)
НзС-СО-СН2-СООСгН5
2 - Acetessigsaureethylestef
H3C-CO-C-COOC2H5
NOH
2-Acetyl-2-0ximtn0-essigsaureethylester {Isomtrosoacetessigester)
К 2 CO? / ICHjOizSO; □imethyl-suifat
H3C-CO-C-COOC2H5
N-OCH3
2 - A с etyl - 2 - met hoxyi m i no -essigsaureethylester
CH^CI? /| p-Tos—OH] /Br;
Br-CH2-CO-C-COOC2H5
N-OCH3
i-Brom - 2-methoxyimmo -acetessigsaureethylestef
NH2
S^N
4-
//
-cooc2Hs
CHjClj /N(C2Hs)3/{C6Hs)3C-Cl
'0CH3
2-[2-Ammo-4-
thiazolyl)-2-methoxy-
imino-essigsaureethyl-
ester
Ш-С(СвН5)з
К
C-COOC2H5
$
0CH3
2 - Methoxyimino- 2 -(2-trityfamino-i-thiazolyl) -essigsaure-ethylester
Ж-С{СбН5)э
К
с-COOH //
\
OCH3
н и , NH-C(C6HS)3
HzN-j—Y ^ 1
ch2ci2/occo/ A-tKftK S r\
2-O-CO-CH3 0
H H
•S.
C~C—NH i Y
/-Ammocephalosporansaure // J I j
N a<’~N'^vCH2-0-C0-CH3
'ОСНэ *
слои
172 С Cefotaxim - Cefotiam
wassr. HCOOH /55°C
nh2
К Si |k ^-c-NH-hr ^
\ СГ N''f^H2~0-CO-CH3
OCH3 I
Coort
Cefotaxim
DOF 3, 749(1978).
DOS 2702 501 (Roussel-Uclaf; Anm. 21.1.1977; F-Prior. 23.1.1976,11.6.1976,18.8.1976). Na-Salz:
DAS 2 708 439 (Hoechst; Anm. 26.2.1977).
D: Claforan® (Hoechst/Glaxo)
Cefotiam 61622-34-2 Antibioticum
(6/?,7/?)-7-[2-(2-amino-4-thiazolyl)acetamido]-3-[[[l-[2-(dimethylamino)-ethyl]-l#-tetrazol-5-yl] thio]methyl]-8-oxo-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CH2-CH2-NICH3)2
H H s j. I. NaHCOj/pH 7/60 - 65"C
H3C-CO-CH2-CO-NH-|—Y 'l HS'^’ 71 2. NH2OH * HC1 /pH 3,6
0^-МукСНз_0-------N-N
-СО-СНз COOH
7-Acetoacetamidocephalosporansaure 1-(2-Dimethy!arrunoethyl)-
1 W-tetrazol-5-thiol
DOF 4,400(1979).
S. Tsushima et al., Chem. Pharm. Bull. 27, 696 (1979).
DOS 2 461478 (Takeda; Anm. 24.12.1974; J-Prior. 25.12.1973, 20.2.1974, 15.4.1974,17.7.1974,
13.11.1974).
DAS 2462 736 (Takeda; Anm. 24.12.1974; J-Prior. 25.12.1973, 20.2.1974,15.4.1974,17.7.1974,
13.11.1974).
Zwischenstufen:
DOS 2607 064 (Takeda; Anm. 21.2.1976; J-Prior. 24.2.1975,20.3.1975, 21.3.1975,1.1.1976).
D: Spi/eF' (Gilinenthul Taкrdu)
Cefoxitin С 173
Cefoxitin 35607-66-0 Antibioticum
33564-30-6 Na-Salz
3-(hydroxymethyl)-7-methoxy-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid carbamate (ester)
HOOC — СИ — fCHjts—С — MH —j—>
NH2 0-7_N's^c:H2_0_co_NH2
COOH Cephamycin С
= 7/?-(D-5-Amino-5-carboxyvaleramido)-3-aminocarbonyl-oxymethyO-T-methcxy-^-cephem-i-carbonsaure {aus KulturfiUraten von Streptomyces lactamdurans (мА-290в|)
