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Patented Dec. 24-, 1946
‘2,413,077
UNITED STATES PATENT OFFICE
2,413,077
cl (+ ) -ALPHA, GAMBIA - DIHYDROXY - BETA,
BETA - DHWETHYL - BUTYRIC - ACID- (HY
DROXY-ALKYL)-AM[DES AND PROCESS
FOR THE MANUFACTURE OF SAME
@tto Schnider, Basel, Switzerland, assignor to
Hoffmann-La Roche Inc., Nutley, N. J., a cor
poration of New Jersey
No Drawing. Application May 8, 1943, Serial No.
486,270. In Switzerland May 8, 1942
6 Claims.
(Cl. 260-561)
2
1
Example 2
Pantothenic acid and homologs thereof have
been manufactured by reacting d(—) -u-hydroxy
130 parts ‘by Weight of (d—)-a-hydroxy-p,,3
dimethyl-v-butyric-acid-lactone and 89 parts by
?,?-dimetliyl-v~butyric-acid-lactone with p-ala
nine, salts or esters thereof, or with other corre
weight of 1-hydrcxy-3-aminobutane are dissolved
in 200 parts by volume of methyl alcohol. The re
action sets in under spontaneous heating of the
mixture. After 24 hours, the methyl alcohol is
sponding amino carboxylic acids (see, for in
stance, Science, vol. 91, year 1940, p. 411; Journal
of the American Chemical Society, vol. 62, year
1940, p, 1785; U. S. Letters Patent No. 2,234,680;
distilled off, The distillation is completed by heat
Helvetica Chimica Acta, vol. 23, year 1940, p. 651;
ing to 100° C. under a pressure of 0.02 mm. The
Journal of the American Chemical Society, vol. 10 d ( +) -a,'y-dihydroxy- {3,13 -dimethyl-butyric-acid
62, year 1940, p. 1628).
(1'-methyl-3’-hydroXy-propyl) -amide is a vis
It has now been found that new derivatives of
cous, colorless oil, easily soluble in water. Its op
d(—) -a,'y-dihydrcxy- 5,5 -dimethyl-butyric acid
tical activity “D20 amounts to +1614 for C=5.32%
can be obtained by allowing alcanolamines to re
in Water.
act thereon. Preferably, the reaction is effected 15 I claim:
in a solvent.
1. d ( +) -a,'y-Dihydroxy-p,p-dimethyl - butyric
The new compounds exert the biological activi
acid- (hydroxy-alkyl) -amides.
ties of pantothenic acid. They are to be used as
2. d(+) -a,'y-Dihydroxy- 13,5 -dimethyl-butyric
medicinal preparations.
'
Example 1
130 parts by weight of d(—) -u-hydroxy-?,,c
20
acid- (3’-hydroxy-propyl) -amide.
3. d(+) -a,'y-Dihydroxy- 5,13 -dimethyl-butyric'
acid- (1’-methyl-3’-hydroXy-propy1) -amide.
4. Process for the manufacture of d(+)-a?
dimethyl-y-butyric-acid-lactone are dissolved in
dihydroxy-ap-dimeth? - butyric-acid-(hydroxy
150 parts by volume of methyl alcohol. '75 parts
by Weight of B-hydroxy-propylamine are added, 25 alkyl) -amides, comprising reacting d(—) -hy
droXy-B?-dimethyl-v-butyric-acid-lactone with
in one portion, to the solution and the mixture is
an alcanolamine in a solvent.
Well stirred. While the reaction sets in, the tem
5. Process for the manufacture of d(+) —a,'y-di
perature of the mixture gradually rises by itself to
hydroxy-o,p-dimethyl - butyric-acid- (3'-hydroxy
about 50° C. and then drops again after about two
hours. To cause completion of the reaction, the 30 propyl) -amide, comprising reacting d(—) -hy
droxy-;8,?-dimethyl-v-butyric-acid-lactone with
mixture is allowed to stand at room temperature
S-hydroxy-propyl-amine in a solvent.
'
for 241 hours. The so obtained (d-l—)-oc,'y-dihy—
6. Process for the manufacture of d(+)-ow
droxy-cc-dimethyl - butyric - acid-(3’-hydroxy
dihydroXy-B,/8-dimethyl - butyric-acid- (l'-meth
propyD-amide is freed from methyl alcohol in
yl-3'-hydroxy-propyl)-amide, comprising react
vacuo. It is a colorless, viscous oil, easily soluble
in water. It boils under a pressure of 0.02 mm.
between 118 and 120° C. Its optical activity “D20
amounts to +29.7° for C=3% in water.
ing d( —) -hydroxy-?,p-dimethyl-q-butyric-acid
lactone with 1-methyl-3-hydroxy-propyl-amide
in a solvent.
O'I'I‘O SCHNIDER.
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