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H
2-Methylpentan-2,4-diol Chloralhydrat
CH3 CH3 H3C-C-CH2-CH-0-CH-CC(3 OH OH
USP 2 931 838 (Det Danske Med.-& Kem.-Komp.; ert. 5.4.1960; DK-Prior. 8.12.1956). GB: Medodorm® (Medo)
Chlorambucil зоб-оз-з
4-[p-[bis(2-chlorethyl)amino]phenyi]butyricacid
Cytostaticum
Chlorambucil - Chloramphenicol С 185
H3C“C0‘
Acetamlid
-nh-0
H3C—CO—NH-
■On-1
•CH2—CH2—COOH
Н2/Р(1-С,СНзОН
Bernstein-saure-
anhydrid
4-(4-AcetaminophenylM-oxobuttersaure
H3C-CO-NH-^^-
(CH2)3-COOCH3
H2N“Q~'
(CH213-COOH
4-(4-Aminophenyl)-butter-
saure
Ethyten-
oxid
но-сн2-сн2
HO-CH2“CH2
K>
(CH2)3-COOH
) P0C13 2.H?0
! Phosphoroxy-cMond
Ct-CH2“CH2
/
CI-CH2-CH2
1-^~^-(СН2),-СООН
Chlorambucil
USP 3 046 301 (Borroughs Wellcome; ert. 24.7.1962; Prior. 29.10.1959).
D: Leukeran® (Wellcome) I: Leukeron® (Wellcome)
F: Chloraminophene® (Techni-Pharma) Linfolysin® (Isfn)
GB: Leukeran® (Burroughs Wellcome) USA: Leukeran® (Burroughs Wellcome)
Chloramphenicol 56-75-7 Antibioticum
d-//im>2,2-dichloro-iV-[/3-hydroxy-«-(hydroxymethyl)]-/7-nitrophenethylacetamide
Parke-Davis-Verfahren-.
1. (CHj)sNt
OjN-fTVc-CH, 02М-<ГЛ-С-СН2-вг -► 02мЧ~У C-CH2-NH2- HCI
^_{/ || Brom v_U II 1. Hexamethylen- '—' Ц
0 0 letramm 0
4-Nitroacetophenon w-Brom-A-mtroacetophenon w-Ammo-4-nitroacetophenon-
(4-Nitrophenacyl-bromtd) Hydrochlorid
(H3C-C0)20
NH -CO-CH-s
/=\ (CH20)n Л=\ I
°2N-^^-C-CH2-NH-CO-CH3 -* 02N-^J>“C-CH-CH2-0H
Acetan- _ .. _
hydrid 0 0
w-Acetamido-4-nitroacetophenon a~ Acetamido-/?-hydroxy-
4-nitropropiophenon
H NH—CO —CH3 ,__ H NH2
Ai lOCH(CH,)2]3 /НО-СН(СН3)2 /=\ II HCI _ _/^\ ’ ' Л11 -—-^ 02N-<\ /)-C-C-CH2-OH -* 02U-\ /VC-C-CH2-0H
Aluminium- '-' 11 - I '
isopropylat OH H OH H
D,L-Mra>-2-Acetamido-l- D,i-f/>reo-2-Arnino-1-№-nitro-
14 - nitrophenyl) -1,3 - propandiol phenyl)-1j3-propandiol
186 С Chloramphenicol
. OjN-Q-W-CH,-» C'-CH-C^
' I I Diehioressiaa^ire
I f Dichloressigsaure-
O'* " methylester
D-(-)-^reo-2-Amino-'l-(4-nitro-
phenyl)-1,3-propandiol
H NH-C0-CHC12
0 2N—^^ ^^2 “0^
OH H Chloramphenicol
Verfahren von Boehringer, Mannheim:
<^^-CH=CH-CH2-OH
Br2/HjO
Zimtalkohol
Br
I
^^-CH-CH-CH,-OH OH
2-Brom-l-phenyl-1,3-propandiol
IHjCljCO
__ Br <QbCH-CH-CHa ^c/°
/ \
H3C CH3
5-Brom-2,2-dimethy(-
4-phenyl-1,3-dioxan
NH2
Q-ch-Ah-ch,
04
с
НзС^ SCH3
0, L-f/veo-5-Amino-
2,2-dimethyl-
4-phenyl-1,3-dioxan
0"ih
0^
nh2
-CH-
CH2
I z
НзС-' чсн3
0-H-f/>reo-5-Amino-
2,2-dimethyl-
4-phenyl-1,3-dioxan
Cl2CH-COOC2H5
Dichloressigsaure-
elhyles)er
NH-CO-CHCb
Г'Усн-сн-снг ^ H nh-co-chci2
x\ fj 1 1 1 HNO.yH.sq. J I ,
0^ -— » 02N-<^-C-C-CH2-0NO2
/C\ CbNO h
H3C CH3 2
o-M-fhreo-5-Dichloracetamido- D-l-)-threo-2 D.chloracetamido-
2,2-dimethyl-4-phenyl-1,3-dioxan Md-nitrophenylM^-propan-
diol-dinitrat
Chloramphenicol
Ehrhart-Ruschig IV, 398 ff.
a L. M. Long, H. D. Troutman, J. Am. Chem. Soc. 71,2469, 2473 (1949).
USP 2 483 871 (Parke-Davis; ert. 1949; Anm. 1948).
USP 2483 884 (Parke-Davis; ert. 1949; Anm. 1948).
USP 2 483 885 (Parke-Davis; ert. 1949; Anm. 1949).
USP 2 483 892 (Parke-Davis; ert. 1949; Anm. 1948).
USP 2 687 434 (Parke-Davis; ert. 1954; Anm. 1953).
USP 2 651661 (Monsanto; ert. 1953; Anm. 1950).
USP2786 870 (Parke-Davis; ert. 1957; Anm. 1954).
М. C. Rebstock et al., J. Am. Chem. Soc. 71,2458-2468 (1949). b Belg-P 539991 (Boehringer Mannh.; Anm. 1955; D-Prior. 1954).
DBP 1 016 718 (Boehringer Mannh.; Anm. 1953).
Belg-P 558 378 (Boehringer Mannh.; Anm. 14.6.1957; D-Prior. 27.6.1956, 22.12.1956). Altemativsynthesen (aus Benzaldehyd und Nitromethan Oder 6-N’itroathanol iiber 2-Nitro-l-phenyl-1, 3-propandiol:
DBP 862 302 (Parke-Davis; Anm. 1949; USA-Prior. 1948).
DBP 1064937 (Boehringer Mannh.; Anm. 1957).
DOS 2 708 301 (Egyt; Anm. 25.2.1977, H-Prior. 25.2.1976).
О-3-Monophosphat:
DAS 1668 961 (Roussel-Uclaf; Anm. 20.2.1968; I-Prior. 20.2.1967,18.5.1967).
Chloramphenicol - Chlorazanil - Chlorbenzoxamin С 187
D: Aquamycetin® (Dr. Winzer)
Catilan® (Hoechst)
Chloramphenicol ,,V“ Heyl® (Heyl) Chloramsaar® (Chephasaar)
Chloromycetin® (Parke-Davis)
Chloroptic® (Pharm-Allergen)
Dura Phenicol (Durachemie)
Fenbiotic® (Eberth)
Fenicol® (Roland Essen)
Isopto Fenicol® (Alcon)
Kamaver® (Engelhard)
Leukomycin® (Bayer)
Nevimycin® (Griinenthal)
Oleomycetin® (Dr. Winzer)
Pantovemil® (Heyden)
Paraxin® (Boehringer Mannh.)
F: Cebenicol® (Chauvin-BIache)
Chloramphenicol Roger BeHon (Roger Bellon) Chloramphenicol Chibret (Chibret)
Isophenicol (Bouchara)
Ophtaphenicol (Faure)
Sintomycetine (Lepetit)
Solnicol® (Robert et Carriere)
Tifomycine® (Roussel)
GB: Chloromycetin® (Parke-Davis)
Kemicotine® (Carlo Erba)
I: Cafenolo® (Benvegna) Chemicetina® (Erba)
Chemyzin® (Sit)
Chloromycetin® (Parke-Davis) Cloramfen® (ScJavo)
Lomecitina® (Locatelli) Micoclorina® (Zambon)
Mycetin® (Farmigea) Paidomicetina® (Lafare)
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