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.. , 1962. 711 c.
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NH-C0-0-CH,-CH,-0H
I 1 1
(CH 2)6
nh-co-o-ch2-ch2-oh
1 каг 2. N(CHjJ3
nh-co-o-ch2-ch,-ci
SOCIj I
-- (CH2)B
Thionyl- I
chlorid nh-co-o-ch2-ch2-ci
1 Kaliumbromid 2. Trimethyl-amtn
NH-C0-0-CH2-CH2-N(CH3)3
(CH2)6
NH-C0-0-CH2-CH2-N(CH3}3
Hexcarbacholin-bromid
DBP 1021842 (Osterr. Stickstoffwerke; Anm. 1954; A-Prior. 1953). D: Imbretil® (Hormonchemie)
Hexetidin
141-94-6
Antis epticum
5-amino-1,3-bis(2-ethylhexyl)hexahydro-5-methylpyrimidine
h5c2-no2 + ch2o
Form-
aldehyd
H3C CH2-0H
с
o2n xch2-oh
2-Melhyl-2-mtro-
propan-1,3-diot
2 rl9Ct-CH-CH2-NHj /CH20 l2-Ethylbe*yl)-amin /'Formaldetiyd
c2H5
H3<V-'K,-CH2"CH_C‘H5
°2N-r\N
N
I
CH2
I
CH “С?н5 I
C,H9
H3/Raney-Ni
N
c2h5
,СН2-СН-СдН9
CH,
I
CH—C-.He I 4 C^Hg
Hexetidin
USP 2415047 (Commercial Solvents; ert. 1947: Anm. 1945).
USP 3054797 (Commercial Solvents; ert. 18.9.1962; Prior. 11.10.1961). M. Senkus, J. Am. Chem. Soc. 68, 1611 (1946).
Reinigungsverfahren:
DBP 2011078 (Godecke; Anm. 9.3.1970).
DAS 2 355 917 (Meditest; Anm. 8.11.1973).
DOS 2709929 (Dolorgiet; Anm. 8.3.1977).
DOS 2310337 (Wulfing; Anm. 1.3.1973).
DAS 2 323150 (Wulfing; Anm. 8.5.1973).
464 H Hexetidin - Hexobarbital - Hexobendin
Salze mit aromatischen Sauren:
GB-P 1538603 (Doll; Anm. 5.11.1976; D-Prior. 6.11.1975, 3.6.1976,16.6.1976). USP4141968 (Doll; ert. 27.2.1979; D-Prior. 16.6.1976).
USP 4142050 (Doll; ert. 27.2.1979; D-Prior. 6.11.1975,3.6.1976).
Nicotinat:
DOS 2310338 (Wulfing; Anm. 1.3.1973).
Doreperoi® (Rentschler)-Komb. F: Collu-Hextril® (Substantia)
Glypesin® (Stada) Hextril® (Substantia)
Hexetidin-Woeim Gurgellosung GB: Oraldene® ("Warner)
(Woeim Pharma) I: Oraseptic1® (Vister)
Hexoral® (Godecke) Sterisil® (Vister)
Hexoral® Spray (Godecke) USA: Sterisil® (Wamer-Chitcott)
Hexobarbital
56-29-1
59-09-9
Na-Salz
Hypnoticum
5-(l-cyclohexen-l-yl)-l,S-dimethylbarbituric acid
I
rv
C00CH <3=0 + CH2 CN
f HN (СгН5)2 i
Cyclo- Cyanessig-
h ex anon saure~
metftylester
C00CH3
u?
CN
1-Cyctohexenyl-
cyanessigsaure-
methyiester
(HjCOIjSOj /NaOCHj
Dimethyl-
sulfat
H3C COOCH3
O'
2-Cyan-2-H-cyclo-
hexenyD-propransaure-
methyiester
NaOCHj/'HzN-C-NH-CN
O^N^NH
[H3C0);S0;
Dimethyl -sulfat
^NH Hexobarbital
DRP595175 (I.G. Farben; 1931). DRP 590175 (I.G. Farben; 1932).
D: Evfpan® (Bayer)
F: Dormopan® (Bayer Pharma)-Komb.
Noctivane® (Vaillant-Defresne)
GB: Evidorm® (Winthrop)-Korab.
J: Cydopan® (Teikoku Kagaku-Nsgase) Ouropan Soda® (Shionogi)
USA: Sombulex® (Riker)
Hexobendin
54-03-5
50-62-4
Coronardilatator
Dihydrochlorid
3,3'-[ethylenebis(methylimino)]di-l-propanol 3,4,5-trimethoxybenzoate diester
Hexobendin - Hexocycliummethylsulfat H 465
CH3 CH* CH, CH*
I I I I 3
2 H3COOC-CH=CH2 + HN-CH2-CH2-NH -► H3COOC-CH2-CH2-N-CH2-CH2-N-CH2-CH2-COOCH3
Acrylsaure- tyN'-Dimethyl-
methylester ethytendiamin
CH3 CH3
LiAlHi I I
-* HO-CH2-CH2-CH2-N-CH2-CH2-N-CH2~CH2-CH2-OH
lithium-
aJanst A/'-Dimethyl-^АЛ-bis-(3-hydroxypropyl)-ethytendiamin
и3С0
3,4,S-Tnmetto*V-
Denzoylchlorid
H3CO
ru ли OCH3 J
_/-=\ 1 3 I 3 /=( i
H3C0-I\ >-C0-0-(CH2)3-N-CH;-CH;-N-(CH2)3-0-C0-<^ ^och, H3CO 0CH3
Hexobendin I
DBP 1217397 (Lentia; Anm. 26.3.1962).
N,N'-bis-(3-hydroxypropyl)-l,2-ethylendiamin aus 1,2-Dichlorethan und 3-Aminopropanol:
DAS 2042320 (Lentia; Anm. 26.8.1970).
D: Instenon® (Byk Gulden)-Komb. F: Hityl® (Biosedra)-Komb.
Reoxyl® (Byk Gulden) Ustimon® (Merck-Clevenot)
I: Flussicor® (Farmalabor)
Hexocycliummethylsulfat 115-63-Э Spasmolyticum;
Anticholinergicum
4-(/>cyclohexyl-/З-hydroxyphenerhy])-1,1 -dimethyipiperazinum methylsulfate
o-
CH2~Br w-Bromacetophenon
HN N-СНз
N_t
1-Methylpiperazm
o<
CH2— _^N-СНз
4-Methyl-1-(2-oxo-2-phenyl-ethyU-piperazin
Cyclohenylbromid bzw. Cyclohexyl-magnesiumbromid
M,c/0H
_N-CH3
tH}C0)?S02
Dimethyl-sulfat
USP 2907 765 (Abbott; ert. 6.10.1959; Prior. 10.9.1956).
D: Traline® retard (Abbott) I: Tral® (Abbott)
F: Traline®(Abbott) USA: Tral® (Abbott)
466 H Hexoestrol - Hexoprenalin
Hexoestrol
(Hexestrol)
84-16-2
Oestrogen
4,4'-( 1,2-diethylelhylene)diphenol
H3CO-^~^-CH-C2H5 + H5C6-MgBr
Ether /Toluol /CoCb
Br
1-Brom-1-{i-methoxy-
phenyU-propan
{vgl. Qiethylstilboestrol-Synthese)
КоаШЛ)-
chtorid
Phenylmag-
nesiumbromid
c2h5
Jodwasserstoff
H3CO О сн-сн o- OCH3
1 _ C2HS 1
|но-0-^:н_|н"0^он! , C2H5 :
! Hexoestrol i
H3CO о CH-C2H5
1 -Brommethoxy -phenyU-propan
1 Metalle (Na,Mg,Al oder Fe) 2. HJ
1 INatnum.Magnesium,Aluminium oder EisenI
2 Jodwasserstoff
a M. S. Kharasch, M. Kleimann, J. Am. Chem. Soc. 65,491 (1943). b E. C. Dodds et al., Proc. R. Soc. London, Ser В 218, 253 (1940).
S. Bernstein, E. S. Wallis, J. Am. Chem. Soc. 62, 2871 (1940).
N. G. Buu-Hoi, N. G. Hoan, J. Org. Chem. 14,3023 (1949).
USP 2 357985 (Research Corp; 1944; Anm. 1940).
GB-P 523 320 (Boots; Anm. 1938),
FP 855 879 (Lab. Frani;. Chimiotherapie; Anm. 1939). Ausgangsverbindung:
S. Bernstein, E. S. Wallis, J. Am. Chem. Soc. 62,2871 (1940). Weitere Verfahren:
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