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Патент USA US2405540

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Patented Aug. 6, 1946
2,405,54
UNITED STATES PATENT‘ QFFICE
2,405,540
NONBENZENOID COMPOUNDS
Lewis W. Butz, Beltsville, Md., assignor to the
United States of America, as represented by the
Secretary of Agriculture
No‘Drawingz- Original application December 12,
1942, Serial No. 468,795. Divided and this ap
plication July 10, 1945, Serial No. 604,289
1 Claim. (01. 260-344;.6)
(Granted under the act of March 3, 1883, as
amended April 30, 1928; 370 0. G. 757)
1
2
four rings of carbon atoms having substantially
‘This application is made under the act of
March 3, 1883, as amended by the act of April 30,
1928, and the invention herein described and
the structure:
0-00
claimed, if patented, may be manufactured and
00/
used by or for the Government of the United 5
States of America for governmental purposes
without the payment to me of any royalty
0H:
thereon.
This application is a division of my copending
‘
My invention relates to non-benzenoid fused
$H
CH—CH’
0
0
CH2
on,
\o%
\(f
\Céz
l
I
I
application for patent Serial No. 468,795, ?led 10
December 12, 1942.
(BE
\ / \
0%’ f5 f5
0H:
CH
00
0(';_.O
polycyclic organic compounds and to processes for '
preparing them.
This is non-benzenoid ‘steroid. It possesses the
I have found that organic compounds belong 15 seventeen-carbon four-ring skeleton common to
ing to the class of 1,5-diene-3-ynes, i. e., com
pounds containing the atomic grouping
all the steroids which have been found in organic
materials. Furthermore, it is a steroid contain
ing only hydrogenated rings and one novel fea
ture of the process'is its capacity to yield poly
react with two moles of dienophilic compounds 20 cyclic compounds lacking any aromatic (benze
containing the atomic grouping
noid) ring.
* All known processes for the synthesis of steroids
relate to the preparation of benzenoid steroids.
such as, maleic anhydride, methyl fumarate,
But the majority of the naturally occurring ste
ethyl fumarate, and other maleates and fuma 25 roids, among them the therapeutically important
rates including substituted compounds, to form
male hormones, adrenocortical hormones, and
stable addition products which contain two car
progesterone are non-benzenoids
bon rings more than are contained in the dim
My process makes available, for the ?rst time,
eyne employed. The reaction is carried out in
the absence of any solvent and at a temperature 30 by synthesis, steroids of the non-benzenoid type,
as well as non-steroid types of polycyclic com
of 130° C. to 175° C. The molecular weight of
pounds,
which are useful as intermediates in the
these products is equal to the sum of the molec
synthesis of therapeutic compounds.
ular weight of the dieneyne employed and twice
The following example for the preparation of
the molecular weight of the dienophilic com
1 - methyl - 5,6 - propano-2,3,4,6,7,8 - hexahydro
pound used.
Thus the dieneyne, cyclohexenylcyclopentenyl
acetylene
011-4311,
\
||
|
/CE= /C§ /C\ /CH1
on,
c
\o
011,
JJH’ gH
\CH
2
reacts readily with maleic anhydride. By this
naphthalene-3,4,7,S-tetracarboxylic-3,4;7,8-dian
hydride will illustrate my invention more fully.
One molecular
proportion of cyclopentenyliso
,
propenylacetylene was added to two molecular
_ proportions of maleic anhydride in an open vessel
40 at 120° C. while passing a stream of carbon diox
ide to exclude air. The mixture was heated at
150°-160° C. for two hours. Volatile components
were then removed by fractional distillation. The
residue was dissolved in ethyl acetate and ether
reaction, there is formed a compound containing 45 was added, resulting in the precipitation of an
2,405,540
3
4
amorphous material. This amorphous material
and its empiric composition is CHI-1140s. The
presence of two conjugated double bonds spread
over two rings is substantiated by absorption
spectrum data.
Having thus described my invention, I claim:
was separated. Part of the ether and ethyl ace
tate was evaporated and the solution was set
aside to crystallize. After seven days, crystals
formed which were separated and recrystallized
from benzene-petroleum ether. The crystalline
The 1 - methy1—5,6-propano-2,3,4,6,7,8-hexahy
product is represented by the following structural
dronaphthalene - 3,4,7,8 - tetracarboxylic-3,4;7,8
formula:
dianhydride, having substantially the structure:
O-GO
10
41H; 05-0
The product has a melting point of 168°-1'70° 0.,
CHE-CE?
CH1
15
LEWIS W. BUTZ.
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