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Патент USA US3036107

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United States Patent
m
3,036,097
Patented May 22, 1962
1
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‘
3,036,097
QUATERNARY AMMONIUM SALTS OF 2043-_
AMINO-ALLOPREGNANE-IlB-OL
Percy George Holton, Mexico City, Mexico, assignor to
Syntex S.A., Mexico City, Mexico, a corporation of
Mexico
No Drawing. Filed July 6, 1961, Ser. No. 122,084
3 Claims. (Cl. 260-3975)
The present invention relates to novel cyclopentano 10
duction thereof.
More particularly the present invention relates to novel
phenanthrene compounds and to a process for the pro—
quaternary ammonium salts of ZOB-amino-allopregnan
3;3~ol.
The novel compounds of the present invention which
HO
.
v
15
are valuable hypotensive agents and muscle relaxants with
ganglionic blocking activities, are represented by the
In the above formulas X has the same meaning as
above set forth.
In practicing the process outlined above, the starting
following formula:
compound allopregnan-BB-ol-ZO-one (I) is conventionally
20
treated with hydroxylamine hydrochloride affording the
corresponding oxime (-II) which upon reduction with
sodium-ethanol furnishes 20?-amino-allopregnan-3B-ol
(III).
This compound is re?uxed with formic acid and’ form
aldehyde ,for a period of time of the order of 2 hours to
give 20B-N,N—dimethylaminoallopregnan-B‘?-ol (IV).
Upon treatment of this compound with a (w-bromo
loweralkyl) trirnethyl-ammonium—bromide, in a suitable
solvent such as acetonitrile, there is obtained the cor
30 responding ZOB-N-('N',N'-dimethylaminoloweralkyl) - N
methylamino-allopregnan-3,3-ol-bis-methobromide (V).
The following speci?c examples serve to illustrate but
In the above equation Me represents the methyl group;
are not intended to limit the, present invention:
X may be a number from 3 to 6 inclusive.
The products of the present invention are prepared by
the process illustrated ‘by the following equation:
35
Example I
A mixture of 1 g. of a1lopregnan-3B-ol-20-one, 2 g. of
hydroxylamine hydrochloride, and 2 g. of sodium acetate
in 200 cc. of 80% methanol is heated under re?ux for 20
‘hours. 100 ml. of water were added and the mixture
was evaporated under reduced pressure until the ap
not? -0?
pearance of crystals. After cooling, the formed crystals
were ?ltered o?? and dried, thus affording the allopregnan
318-01 20-one oxime.
To a re?uxing solution of this oxime in 100 cc. of n
‘butanol were added portionwise 5 g. of sodium. The
resulting solution was diluted ‘with 100 cc. of water,
acidi?ed with acetic acid and evaporated under reduced
II
CH3
CH;
IV
l
solution was washed with ether, made alkaline with a
OH;
e1
H0
pressure until the butanol had been removed. The acidic
- at
5% aqueous sodium hydroxide solution, the liberated
product extracted with methylene chloride, the extract
washed with water, dried over anhydrous sodium sulfate
and evaporated to dryness. Recrystallization from ace
tone a?orded 20?-amino-allopregnan-313-01.
Example II
1 g. of this last steroid was re?uxed with 3 cc. of 90%
formic acid and 2.5 cc. of 40% formaldehyde for 2 hours.
60 The mixture was evaporated under reduced pressure, the
residue alkalized with sodium carbonate solution and
the resulting mixture extracted with ether. The extract
was washed with water, dried over sodium sulfate and
evaporated to dryness. Recrystallization from ethanol
3,036,097
benzene 'a?orded 2018-(N,N-dimethy1amino)-5l1opiegnan- '
35-01.
‘Example III
I claimi
'
'
1. A compound of the folio, ‘ng formula:
‘
0H; CH.
C|H3
H——C—-N+—(C m) rN+~CH1
CH3
CH;
A’ mixture of 1 g. of the foregoing compound, 2 g. of
l ('y-bromopropyn-trimethy-l ammonium bromide, and 10
cc. of acetonitrile was refluxed for 24 hours, then cooled
2131"‘
and diluted with ether. The precipitate .thus formed was
collected andrrec'rystallized from methanol giving 205
N-(N’,N'-dimethylaminopropyl)N - methylamino - allo
pregnan-3?-obbis-methobromide.
1O
H0
Example IV
1 g. of 20,8-(N,N-dimethylamino)-al1opregnan-3|9-ol
was treated following the technique described in Example
III except that ('y~bromo-propyl)-trimethyl-a.mmonium
bromide was substituted ‘by (6-bromobutyD-trimethyl
wherein X is an integer from 3 to 6.
2. 2013 - Ny-(NZN’ - dimethy-laminopropyl) -N~- methyl
15
ammonium ‘bromide thus affording 20?-N-(N’,N'-dimeth- '
ylaminobutyl)—N-methylamino>.- allopregnan — 3,8 - 'ol-‘bis
methobromide.
‘
'
amino-allopregnan-3?-ol-bis-methobromide.
' '
3. 20B - N - (N',N'-di-methylaminobutyl)-(N - methyl-j
amino-allopregnan-S?-olebisemethobromider
'
No references citédl,
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