- ..
( ):
dioxolan
со-о-снг-<^СНз
CH3
I j/hci
4,7-OiCWor-chinoltft
CO-0-CH2-CH-CH2-0H OH
Glafenin
DOT 2, 139(1966).
USP 3 232 944 (Roussel-Uclaf; ert. 1.2.1966; F-Prior. 20.8.1962). FP-M 2413 (Roussel-Uclaf; Anm. 20.11.1962; Prior. 20.8.1962). Anthranils2uremonoglycerid aus Isatosaureanhydrid:
E-Anm. 678 (Pierre Fabre; Anm. 18.7.1978; F-Prior. 26.7.1977).
442 G Glafenin-Glaziovin
D: Glifanan® (Albert-Roussel) I: Giifan® (Roussei-Maestrctti)
F: Adalgur® (Roussel)-Komb. J: Glifanan® (Nippon Roussel-Chugai)
Glifanan® (Roussel)
Glaziovin 17127-48-9 Tranquilizer
* (±)-glaziovine
CH2-COOH
H3CO.
H3CO'
xxj
ch3
Palyphospftcrsaure
6J7-D'rnethoxy-2-methyt-
1,2,3,4-tetrahydroisochrnolin-
1-essigsaure
H3CO'
(СеН5Р=СН—OCH3/PMSO _
Methoxymethylen-
tnphenylphospfiofan
H3CO-C
H0YT'N"CH3
НзСО'^^ ^
HjC-SO^H /Нг0
Methansglfor-
saure
HO.
H3CO'
.CH3
H3C-C-CH=Cb2/KOC(CH3h
Metfiylvmyiketon Kalium-
tert -butyiat
H3CO
(i)-Dihydroglaziovin
I (С^зСО)^О f Pyndin 2. Bf2 / HBr /СН3СООН
1,8-Diaza*
bicyclo|5 4 Oj-undecen- (7)
DOT 13, 24 (1977).
DOS 2 363 531 (Siphar; Anm. 20.12.1973; CH-Prior. 22.12.1972).
GB-P 1459 210 (Siphar; Laufzeit ab 18.12.1973; CH-Prior. 22.12.1972. Weitere Verfahren:
USP 3 886 166 (Siphar; ert. 27.5.1975; CH-Prior. 22.12.1972, 26.2.1973). DOS 2 363 529 (Siphar; Anm. 20.12.1973; CH-Prior. 22.12.1972, 26.2.1973). T. Kametani et al., Tetrahedron Lett. 1973,4219.
DOS 2 363 530 (Siphar; Anm. 20.12.1973; CH-Prior. 22.12.1972).
Isolierung aus den Blattem der Ocotea glaziovii:
B. Gilbert et al., J. Am. Chem. Soc. 86, 694 (1964).
I: Suavedol® (Simes)
Glibenclamid - Glibornurid G 443
Glibenclamid 10238-21-8 Antidiabeticum
(Glyburide)
l-[4-[2-(5-chloro-2-methoxybenzamido)ethyl]-phenylsulfonyl]-3-cyclohexylurea
ОСНз (/ \_C00H
Thionyi-
chlorid
рСНз
h2n-ch2
-снг~0
2-Phenylethylamrn
5-Chlor-2-methoxy-
benzoesaure
Cl
\. CISO3H
2. NH3
I Chlor-
0 sutfonsaure f Q
0"fi-NH-CH*-CH*-0 fmU— • <p^C-NH-CH2-CH2-H0>-SO2-
ОСНз
nh2
ОСНз
0=c=n-Q ' ^^-с-мн^-снг-снг—SO2-NH-C-NH—{^)|
Cyclohexyliso- Cl 0 6
cyanat i
I Glibenclamid
DOTS, 98(1969).
W. Aumuller et al., Arzneim.-Forsch. 16,1640 (1966).
DBP 1283 837 (Hoechst; Anm. 13.7.1967; CDN-Prior. 21.7.1966) DBP 1 301 812 (Hoechst; Anm. 27.7.1965).
Belg-P 684 652 (Hoechst; Anm. 27.7.1966; D-Prior. 27.7.1965).
D: Euglucon® (Boehringer Mannh.-Hoechst)
Semi-Euglucon® (Hoechst/Boehringer Mannh.) F: Daonil® (Hoechst)
Euglucan® (Pierre Fabre)
Hemi-Daonil® (Hoechst)
Miglucan® (Pierfe Fabre)
GB: Daonil® (Hoechst)
Euglucon® (Roussell)
I: Daonil® (Hoechst)
Euglucon®-5 (Boehringer Biochemia) Gliben® (Gentili) u. Komb.-Prap.
J: Daonil® (Hoechst)
Euglucon® (Yamanouchi)
USA: Diabeta® (Hoechst-Roussell) Micronase® (Upjohn)
Glibornurid 26944-48-9 Antidiabeticum
l-(2-endc>-hydroxy-3-ertd0-bornyl)-3-(-p-tolylsulfonyl)-urea
h3c ch3 j H3CYCCHH33]
H3M^-S02-NH-C* + H * H3C-«^^-S02-NH-C-NH
p-Toiuolsulfonylethyiurethan S-endo-Amino- L___ Glibornurid
D-borneol
444 G Glibornurid - Gliclazid - Glipizid
DOT 8,88 (1972).
DBP 1 695 201 (Hoffmann-LaRoche; Anm. 21.9.1967; CH-Prior. 28.10.1966, 24.4.1967,17.7.1967). USP 3 654357 (Roche; ert. 4.4.1972; CH-Prior. 26.4.1968).
D: Gluborid® (Griinenthal) F: GJutril® (Roche)
Glutril® (Roche) GB: Glutril® (Roche)
Gliclazid 21187-98-4 Antidiabeticum
l-(3-azabicyclo[3,3,0]oct-3-yl)-3-[p-tolylsulfonyl)urea
,±aN0-’'HiU on-nQ^>
3-Azabicydo N- Amino- 3- azabi-
J 3.3.0 j-octan cyclo 13.3.Q] -octan
HjC—^>-S0;-Nh-c0°c2h5 4-TolylsulfonyUthyiurethan
H3C—s°2-NH -C - NH-\^X0>
Gliclazid
USP 3501 495 (Science Union; ert. 17.3.1970; GB-Prior. 10.2.1966).
FP 1510714 (Science Union; Anm. 9,2.1967; GB-Prior. 10.2.1966).
D: Diamicron® (Pharmacodex) I: Diamicron® (Servier)
F: Diamicron® (Servier) Dramion®(Maggioni)
Glipizid 29094-61-9 Antidiabeticum
l-cyclohexyl-3-[[p-[2-(5-methylpyrazinecarboxamido)ethyl]phenyi]sulfonyl]urea
H3C^JV.
W N
XI
^N'TOOH
6-Methylpyrazin-
3-carbonsaure
1. S0C12
Z. HjN-CHj-CHi—^>-S02-NH2 I Thionylcblond
2. 4-(2'Amino*thyl)-berzoUulfonamid |s 4- Aminosulfonyl-2-phenylethyl-
amm}
A-
и
о
,nh-ch2-ch2-
•S02-NH2
Cyclohexylisocyanat
| H3C^N. --—|
| ^NH—CHj—CH2—у—S02~NH—С — ЧН—( V
N С п
Glipizid
DAS 2012 138 (Carlo Erba; Anm. 14.3.1970; I-Prior. 26.3.1969, 18.6.1969). USP 3 669966 (Carlo Erba; ert. 13.6.1972; I-Prior. 26.3.1969,18.6.1969).
V. Ambrogli et al., Arzneim.-Forsch. 21,200 (1971).
Glipizid - Gliquidon - Glisoxepid G 445
D: Giibenese® (Pfizer) GB: Glibenese® (Pfizer)
F: Glibenese® (Pfizer) Minodiab® (Montedison)
Minidiab® (Carlo Erba) I: Minidiab® (Erba)
Gliquidon 33342-05-1 Antidiabeticum
l-cyciohexyl-3-[[/?-[2-(3,4-dihydro-7>methoxy-4,4-dirnethyI-l,3-dioxo-2(l//)-isoquinolyl)ethyl]
phenyl]sulfonyl]urea
CH3
НзС
о
‘CH3
1. HN03
2 Hi / Raney-Ni
3 NaNO*
4 wass. H?50i
5 (CH*QliSOi
2,/*,4-Trimethyl-
