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Патент USA US3065245

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United States Patent O??ce
3,055,235
Patented Nov. 20, 1962
1
2
3,065,235
7-CHLORG-2-CHLQREDMETHYL-G-SULFAMYL
1,2,3,d-TETRAHYDRO-4-QUINAZOLINGNE
Elliott Cohen, Mount Vernon, and Eetty Klarberg, New
York, N.Y., assignors to American Cyanamid Com
The invention will be described in greater detail in
conjunction with the following speci?c example.
EXAMPLE
Preparation of 7-Chl0r0-2-ChI0r0met‘hyl-6-Sulfamyl
1,2,3,4-Tetrahydr0-4~Quinaz0lin0ne
pany, New York, N.Y., a corporation of Maine
No Drawing. Filed June 15, 1960, Ser. No. 36,140
1 Claim. (Cl. 260--256.4)
H
NH,
'
l
I
N
This invention relates to 7-chloro-2-chloro-methyl'6 10
ooNH,
01
H
4011,01
sulfamyl;1,2,3,4-tetrahydro-4-quinazolinone of the for
mula:
O1_
1?
N
01
NH
\/NH
||
501N112
H
_onloi
Nuzsoi
CIOHHOHO Nmsok
0
Three grains of 4-chloro-S-sulfamylanthranilamide
were dissolved in 400 milliliters of hot ethanol. The
solution was concentrated to 300 milliliters and 0.3
milliliter of concentrated hydrochloric acid and 5.0
milliliters of 40% aqueous chloroacetaldehyde were
O
20 added. After re?uxing for four hours, the solution Was
The novel compound of this invention is a useful
evaporated to dryness. The solid was dissolved in meth
diuretic and saluretic of low toxicity. The new com
anol. Three batches of product were obtained by con
11
pound also has greater potency than previously reported
quinazolinones.
The new compound may be adminis
centrating the solution. Crude yield: 2.4 g. (65%). A
portion (0.30 g.) of the solid was treated with activated
tered orally or parenterally and when so administered 25 charcoal and recrystallized from ethanol, yielding 0.18
has been found to be effective in causing ?uid sodium
and chloride diuresis in low dosage. For example, in
test animals an oral dose of 0.1 mg./kg. has been found
to result in a 4-fold increase over the controls in 0-24
g. of white powder, M.P. 225° (eii).
We claim:
7 - chloro-2-chloromethyl-6-sulfamyl-1,2,354-tetrahydro
4-quinazolinone of the formula:
hour sodium and chloride excretion.
30
The new compound is a white crystalline solid, in
soluble in water and relatively soluble in lower alkanols,
acetone, dimethylformamide and the like.
IiN
01
The novel compound may be prepared by reacting 4
chloro—5-sulfamylanthranilamide with a lower haloalkyl 35
aldehyde or haloalkyl acetal such as chloroacetaldehyde.
H2NOlS~
011,01
VNH
H
0
The reaction is preferably carried out in a solvent such
as diethylene glycol dimethyl ether, alkyl ethers, alkoxy
References Cited in the ?le of this patent
UNITED STATES PATENTS
alkanols, dioxanes, tetrahydrofurans or lower alkanols.
The temperature may range from about 30° to about
130° with optimum results being obtained at 80° C. to
100° C. The product may be isolated from the reaction
mixture in any convenient manner and may be puri?ed
by recrystallization in a standard manner.
/
3,004,024
Bernstein et a1 _________ __ Oct. 10, 1961
OTHER REFERENCES
Smith et al.: “Tetrahedron,” volume 1, pp. 38-44
(1957).
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