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. .: , 2007. 608 c.
ISBN 5-98657-009-
( ): pharmazeutischewirkstoffe1982.djvu
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Alternativsynthese (Umsetzung der 3-Hydroxy-Verbindung mit Dimethylcarbamoylchlorid):
DOS 2 558 015 (Siphar; Anm. 22.12.1975; CH-Prior. 6.3.1975).
Vorprodukte:
GB-P 972 968 (Roche; Anm. 9.12.1960; USA-Prior. 10.12.1959,15.1.1960, 26.4,1960, 27.6.1960). L. H. Stembach u. E. Reeder, J. Org. Chem. 26,4936 (1961).
S. C. Bell u. S. J. Childress, J. Org. Chem. 27, 562,1691 (1962).
D: Albego® (Boehringer Ing.) I: Albego® (Simes)
Limpidon® (Crinos)
Camphotamid
4876-45-3
Analepticum
(Camphetamide)
3-diethylcarbamoyl-l-methylpyridinium с amphorsulfonate
CH3
Nicethamid (vgl.S. 630)
Camphersuifonsauremethyl-
ester
FP 812 032 (Soc. Franc, de Rech. Biochimiques; Anm. 1936).
F: Tonicorine® (Lematte et Boinot)
Camylofin
54-30-8
5892-41-1 Hydrochlorid
Spasmolyticum
(Acamylophenin)
iV-(2-diethylaminoethyl)-2-phenylglycine isopentyl ester
C2H5
• HCl
nh2
Phenylglycin-isopentylester
2-Diethylaminoethyl-
chlorid-Hydrochlorid
д
Camylofin
Camylofin - Capreomycin - Captodiam С 141
DBP 842 206 (Asta; Anm. 1950).
D: Avacan (Asta)
Avafortan® (Asta)-Komb.
F: Avafortan® (Lucien)-Komb. Dilavacol® (Sarget)-Komb. Sedomuth® (Lucien)-Komb.
I: Avacan® (Schering) J: Adopon® (Kowa) Avacan® (Uji) Rugo® (Hokuriku)
Capreomycin 110ОЗ-З8-6 Tuberkulostaticum
(Caprenomycin) 1406-37-4 Sulfat (Peptid-Antibioticum)
* Capreomycin
Neben IB enthalt es noch IA, IIA und 1IB
о CH3 0 CH2NH2
0 c-nh-ch-c-nh-ch
II I u I
ch2-ch2-ch2-ch-ch2-c-nh-ch h c=o o
NHj NHl ^H2 C^NH ^NH-C-NHj
NH-C-CH-NH-C-C=C |
■ Capreomycin II 0 H I
Aus Kulturfiltraten von Streptomyces capreolus durch Ionenaustauscheradsorption DOT 1,33 (1965).
USP 3 143468 (Eli Lilly; ert. 4.8.1964; Anm. 25.5.1962; Prior. 2.11.1959).
D: Ogostal® (Lilly) J: Capastat® (Shionogi)
F: Capastat® (Lilly) USA: Capastat® (Lilly)
GB: Capastat® (Dista)
Captodiam 486-17-9 Psychoregulans;
904-04-1 Hydrochlorid Sedativum
2-[p-(butylthio)-a-pheny!benzylthio]-iV,N-dimethylethylamine
H3C - (СН2)з- S НзС-(СН2|3 - S H3C — (CHih — s
0 „ 4
CH - OH -► CH
6 6 6
4-Butylthiobenzophenon U - Butytthiobenzhydrol 4 - Butylthiobenzhydrylchiorid
(aus л-Butylphenylthicether und Benzoylchlond)
142 С Captodiam - Captopril
). HjN-C-NH2
2. NaOH_
1 ThiohafrstoM
H3c—(CH2)3—s
CH-SH
4~0utylthiobenzhydrylmercaptan
МаОС2Н5 / С1-СНг-СН?-ЩСНз_ 2-Oimethylanninoethyl-chlond
USP 2 830088 (О. H. Hubner u. P. V. Petersen; ert. 1958; DK-Prior. 1952). F: Covatine® (Bailly)
Captopril
Antihypertonicum
l-[(2S)-3-mercapto-2-methylpropionyl]-L-proline
1. H2C = C-COOH + H3C-CO-SH CH3
Methacrylsaure
Thioessigsaure
H3C-CO-S-CH2-CH~COOH
CH3
3 - Acetylt hio- 2 - methylpropionsaure
// i—i
H3C-CO-S-CH2-CH-C s [Aj CH3 Cl
2 O,
4N^COOH
H
L-Prolin
ci —с-0 —CH2—C6H5 /NaOH
Chlorameisensaure-
benzylester
(Лсоон
I
*C-4
о' 0-CH2-C6H5
N- Senzyloxycarbonyl -L-prolin
H2C=C /H2S04 снз__
^^■С00С[СНз
СГ 0-СН2-СбН5
N-Benzyloxycarbonyl -l -proliri - terf-butylester
rv * [F
4N^COOC(CH3)3 '— H
L-Prolm-terf-
butylester
Captopril - Carazolol С 143
ПП Гд] NaOH^ j—у CF3COQH /Amsol ^
LJ + LJ v4:ooc(CH3)3 ^,И5«-
<r CH-CH2-S-CO-CH3
CH3
^ Racematspaltung ub*r das Dicyclo-
'■СООН hexylamin-Salz in Ethylacetat , ,, 4 . ... _ „ ,
N -► l-|3-AcetylthiO-2-o-methylpropanoyO-
q L-prolin
0^ ''CH-CHj-S-CO-CHj
CH3 | I
1-[3-Acethylthio-2-O.L-methyl- j N COOH i
propanoyl)-i--prolin nh3/ch3oh > .c
-* I О CH--CH2—SHj
! CH3 ]
| Captopril I
I—\ Oiastereomerentrennung ,—«
0-COOH. ♦ 0 -- (Лсоон Captopril
H I
с
0* vcm-ch2-s-co-ch3
СНз
L-Prolin М3-Acetylthio-2-o-methyi-
propanoyl)-L-prolin
DOF 3, 795 (1978); 4,844 (1979).
DOS 2 703 828 (Squibb; Anm. 31.1.1977; USA-Prior. 13.2.1976, 21.6.1976, 22.12.1976). USP 4046 889 (Squibb; ert. 6.9.1977; Anm. 13.2.1976).
USP 4105 776 (Squibb; ert. 8.8.1978; Prior. 13.2.1976, 21.6.1976, 22.12.1976).
USP 4154840 (Squibb; ert. 15.5.1979; Prior. 13.2.1976, 21.6.1976, 22.12.1976, 9.3.1978). Kombin. mit Diuretica:
DOS 2 854 316 (Squibb; Anm. 15.12.1978; USA-Prior. 27.12.1977).
D: Lopirin® (Heyden) J: Capoten® (Squibb)
F: Loprii® (Squibb) USA: Capoten® (Squibb)
GB: Capoten® (Squibb)
Carazolol
57775-29-8
Betablocker
l-(carbazol-4-yloxy)-3-(isopropylamino)-2-propanol
NaOH /Oioxan
4-Hydroxycar-
bazot
CI-CH2
Epichlorhydrin
Н^-СН(СН3)2 /с2н5он
0-CH2-<J
4-(2,3 -Epoxypropoxy)-carbazol
144 С Carazoiol - Carbachol - Carbamazepin
он CH3
i i 0-CH2-CH-CH2-NH-CH-CH3
DOF 2, 715 (1977); 3,859 (1978); 4, 848 (1979).
DOS 2240599 (Boehringer Mannh.; Anm. 18.8.1972).
GB-P 1369 580 (Boehringer Mannh.; Laufzeit ab 9.10.1974; D-Prior. 18.8.1972). Ausgangs verbindung:
DOS 2 928 483 (Boehringer Mannh., Anm. 14.7.1979).
D: Conducton® (Klinge)
Carbachol
(Carbacholine)
51-83-2
Parasympathomimeticum
choline chloride carbamate
Ci-CH2-CH2-0H + coci2
2-Chlor ethanol Pbosgen
(Ethylenchlorhydnn)
Cl--CH2-CH2-0--C,
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