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. .: , 2007. 608 c.
ISBN 5-98657-009-
( ): pharmazeutischewirkstoffe1982.djvu
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D: Panoral® (Lilly) J: Kefral® (Shionogi)
GB: Distador® (Dista) USA: C’ccioi* (Lulv)
Cefadroxil 50370-12-2 Antibioticum
(6R,7/?)-7-[(R)-2-arnino-2-(/>-hydroxyphcnyl)acetamido]-3-methyl-8-oxo-5-thia-
l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CH-COOH
NH-C=CH-C00CH3 CH3
D-|-)-4-Hydroxyphenylglycin (DANE-Salz)
USP 3 489 752 (Bristol-Myers; ert. 13.1.1970; Anm. 5.9.1967).
GB-P 1240687 (Bristol-Myers; Anm. 5.9.1968; USA-Prior. 5.9.1967).
USP 3 985 741 (Bristol-Myers; ert. 12.10.1976; Prior. 15.9.1972,18.10.1974). GB-P 1 532 682 (Bristol-Myers; Anm. 27.4.1976; Laufzeit ab 7.3.1977). Kristallines Monohydrat:
USP 4 160 863 (Bristol-Myers; ert. 10.7.1979; Prior. 7.4.1977, 2.2.1978).
DOS 2 718 741 (Bristol-Myers; Anm. 27.4.1977; GB-Prior. 27.4.1976, 7.3.1977).
D: Cephamox® (Bristol) USA: Duricef® (Mead Johnson)
F: Oracefal® (Bristol)
Cefalexin 15686-71-2 Antibioticum
(Cephalexin) 23325-78-2 Monohydrat
7-(D-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid
1 Cl-COOC2Hs/NtC2Hs)3
H H s
2 О^к^СНэ
_COOH_
2. 7-Дп\«чо-3-dea«toxy-cephatosporansaur»
I
NH2
H H
CO —NH—j—г 's|
CH3
162 С Cefalexin
Cefaloglycin
COOH
Q"
H H
CH-CO-NH-j—
NH2 о^М%^Сн2-о-СО-СН3
COOH
Cefaloglycin
О
if
+ (H3O3C-O-C
Chlorameisensaure-
terf-butylester
(Boc-Cl)
Q-
H*/Pd-BaS04/NaHC03
NH-Boc N'^4-CH2-0-C0-CH3
COOH
О-1
н н
CH-CO-NH-j—
NH-Boc
COOH
\ CFjCOOH 2 AmbeMite LA-1
CH3
N-Si{CH3)3
H3C—C‘
S0—Si(CH3;3
A/,0-BJS-(trimethyl-
silyU-acetamid
H2N_H" 'i
COOH
7-Amino-3-deacet-
oxycephalosporan-
IH3CbSi “ NH —j—Y >
COOSi{CH3)3
('V- CH-COONa ,
\=/ I /CH3CN/
1. NH-C-CH-COOCH3 /(HjC]2N_CH2_CMs /
CH3 I C( —COOCH3
2. СНзОН__
1 3-(a-Carho*ybef\zyi-amirK5)- N- Benzyldim«thyl-crotonsauremelhylester (Na- amm salz) [0-1 ~ I - Phenylgtycin,
DANE-Salz]
DOT 4,164 (1970), 7,183,187 (1971).
USP 3 507 861 (Lilly; ert. 21.4.1970; Prior. 31.7.1962,14.9.1966). a und b
C. W. Ryan et al., J. Med. Chem. 12,310 (1968).
FP 1 524225 (Eli Lilly; Anm. 23.3.1967; USA-Prior. 14.9.1966). GB-P 1 174335 (Eli Lilly; Anm. 7.3.1967). с DOS 1 942454 (Lilly; Anm. 20.8.1969; USA-Prior. 23.8.1968).
GB-P 1459 807 (Proter S.p.A.; Anm. 27.5.1975). Reinigungsverfahren:
USP 3 634416 (Glaxo; ert. 11.1.1972; GB-Prior. 26.3.1969).
USP 3 676437 (Glaxo; ert. 11.7.1972, GB-Prior. 26.9.1969).
Cefalexin - Cefaloglycin С 163
Weitere Verfahren (auch Ringerweiterung von PenicilUn-sulfoxidestern):
GB-P 1 204 394 (Eli Lilly; Anm. 8.5.1968; USA-Prior. 8.5.1967).
USP 3 502 663 (Eli Lilly; ert. 24.3.1970; Anm. 21.4.1969).
USP 3 671449 (Lilly; ert. 20.6.1972; Prior. 23.8.1968, 19.8.1970).
DAS 2 012 955 (Eli Lilly; Anm. 18.3.1970; USA-Prior. 18.3.1969).
DOS 2 117 377 (Bristol-Myers; Anm. 8.4.1971; USA-Prior. 10.4.1970,5.10.1970). DOS 2 127 225 (Yamanouchi; Anm. 2.6.1971; J-Prior. 12.6.1970, 15.6.1970).
DAS 2 241 091 (Toyo Jozo; Anm. 21.8.1972; J-Prior. 20.8.1971, 14.1.1972).
DAS 2 242 684 (Lilly; Anm. 30.8.1972; GB-Prior. 11.9.1971).
USP 3 946002 (Eli Lilly; ert. 23.3.1976; Anm. 11.7.1974).
DOS 2 728 578 (Lilly; Anm. 24.6.1977; USA-Prior. 1.7.1976).
R. R. Chauvette et al., J. Org. Chem. 36,1259 (1971).
Acylierung iiber 1,3,2-Dioxaboranyl-Derivate:
DOS 2 755 902 (Dobfar; Anm. 15.12.1977; I-Prior. 16.12.1976).
Mikrobiologische Acylierung:
USP 4073 687 (Shionogi; ert. 14.2.1978; J-Prior. 14.5.1975).
Kristallines Monohydrat:
USP3531 481 (Lilly; ert. 29.9.1970; Prior. 21.4.1969).
USP 3655656 (Lilly; ert. 11.4.1972; Prior. 21.4.1969,4.6.1970).
Salze mit Sulfonsauren:
USP 3 676434 (Lilly; ert. 11.7.1972; Prior. 29.7.1970).
Retard-Praparation:
GB-P 1543 543 (Shionogi; Anm. 11.5.1977; J-Prior. 13.5.1976).
D:
GB:
Ceporexin® (Hoechst-Glaxo)
Oracef® (Lilly)
Ceporexine® (Glaxo)
Keforal® (Eli Lilly France)
Ceporexine® (Glaxo)
Keflex® (Lilly)
Cefaxin® (Bristol)
Ceporex® (Glaxo)
Cepoven® (Glaxo)
ChemoSporal® (Erba)
Diabeton® (Teknofarma)
Lorexina® (Crosara)
Monohydrat:
Domucef® (Medici Domus)
Keforal® (Lilly)
Latoral® (Dukron)
Sasperos® (Schiapparelli)
Na-Salz:
Alfaspoven® (Alfa Farm.)
Cepoduc® (Glaxo)-Komb.
Cephalexin (Kowa; Maruko; Nihon Iyakuhin; Sanko; Santen; Sanwa; Sawai;Toho;
Towa; Tsuruhara)
Cephaiomax® (Daisan)
Cephazal® (Hokuriku)
Cepol® (Torii)
CEX® (Glaxo)
Ciponium® (Nippon Kayaku) Derantel® (Nippon Chemiphar) Garasin® (Wakamoto) Iwalexin® (Iwaki)
Keflex® (Shionogi)
Larixin® (Toyama)
Madlexin® (Meiji)
Mamalexin® (Showa) Mepilacin®-DS (Kanto Ishi) Ohlexin® (Ohta)
Oracocin® (Tobishi)
Oroxin® (Otsuka)
Rinesal® (Kissei)
Saiitex® (Banyu)
Segoramin® (Takata) Sencephalin® (Takeda) Suciralin® (Mohan)
Syncl® (Toyo Jozo)
Taicelexin® (Taiyo) Tokiolexin® (Isei)
Xahl® (SS Seiyaku)
USA: Keflex® (Lilly)
Cefaloglycin 3577-01-3 Antibioticum
(Cephaloglycin) 22202-75-1 Dihydrat
7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-l-azabicyclo[4.2.0]oct-2-ene-
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