Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Cyclopentanohydrophenanthrene ring system doai
Reexamination Certificate
2000-12-21
2003-03-18
Qazi, Sabiha (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Cyclopentanohydrophenanthrene ring system doai
C514S172000, C514S173000, C514S174000, C552S508000, C552S523000, C552S525000, C552S623000, C552S610000, C552S500000
Reexamination Certificate
active
06534490
ABSTRACT:
DESCRIPTION
The invention relates to new, unsaturated 14,15-cyclopropano-androstanes, their production and pharmaceutical preparations that contain these compounds.
Unsaturated 14,15-cyclopropano-androstanes of general formula I
are described.
In general formula I, R
1
is a hydrogen atom, a hydroxy group, an alkyloxy, acyloxy, aryloxy, aralkyloxy or an alkylaryloxy group, a radical —OCONHR
9
or —OCOOR
9
with R
9
standing for a hydrogen atom, an alkyl, aryl, aralkyl or alkylaryl radical with 1-10 carbon atoms in each case,
R
2
stands for a hydrogen atom, a hydroxyl group, an alkyl, acyl, aryl, aralkyl, alkylaryl group with 1-10 carbon atoms in each case,
for a radical —(CH
2
)
n
CH
2
Y with n=0, 1 or 2, and Y stands for a fluorine, chlorine, bromine or iodine atom, for a cyano, azido or rhodano group, for a radical —OR
10
or —SR
10
with R
10
standing for a hydrogen atom, an alkyl, aryl, aralkyl or alkylaryl radical with 1-10 carbon atoms in each case or an acyl radical COR9 with R
9
standing for an alkyl, aryl, aralkyl, or alkylaryl radical with 1-10 carbon atoms in each case, a radical —OR
9
with R
9
standing for a hydrogen atom, an alkyl, aryl, aralkyl or alkylaryl radical with 1-10 carbon atoms in each case,
for a radical —(CH
2
)
m
—CH═CH(CH
2
)
n
—R
8
with m=0, 1, 2 or 3 and n=0, 1 or 2, and R
8
stands for a hydrogen atom, an alkyl, aryl, aralkyl or alkylaryl radical with 1-10 carbon atoms in each case or a hydroxyl group, an alkoxy group or acyloxy group with 1-10 carbon atoms in each case,
a radical —(CH
2
)
o
C≡CR
11
with o=0, 1 or 2, and R
11
stands for a hydrogen atom, a fluorine, chlorine, bromine or iodine atom, an alkyl, aryl, aralkyl, alkylaryl or an acyl radical with 1-10 carbon atoms in each case,
R
1
and R
2
, independently of one another, stand for a keto, methylene, or difluoromethylene group,
there can be a double bond between C-6 and C-7,
an &agr;- or &bgr;-cyclopropane group X, indicated by X, that is shown standing for a CZ
2
group with Z standing for a hydrogen, fluorine, chlorine, bromine or iodine atom, is located between C-14 and C-15,
R
3
and R
4
, independently of one another, stand for a hydrogen atom, an &agr;- or &bgr;-position alkyl group with 1-10 carbon atoms,
R
5
stands for an alkyl group with 1-3 carbon atoms.
The compounds according to the invention, the new, unsaturated 14,15-cyclopropano-androstanes, have not yet been described. Their biological action is still unknown.
The object of this invention is to make available unsaturated 14,15-cyclopropano-androstanes of general formula
and their pharmaceutically acceptable salts as well as a process for their production.
Another object is to make available pharmaceutical preparations that contain at least one compound of general formula I or their pharmaceutically acceptable salts.
In general formula I
R
1
is a hydrogen atom, a hydroxy group, an alkyloxy, acyloxy, aryloxy, aralkyloxy or an alkylaryloxy group, a radical —OCONHR
9
or —OCOOR
9
with R
9
standing for a hydrogen atom, an alkyl, aryl, aralkyl or alkylaryl radical with 1-10 carbon atoms in each case,
R
2
stands for a hydrogen atom, a hydroxyl group, an alkyl, acyl, aryl, aralkyl or alkylaryl group with 1-10 carbon atoms in each case,
R
2
stands for a radical —(CH
2
)
n
CH
2
Y with n 0, 1 or 2, and Y stands for a fluorine, chlorine, bromine or iodine atom, for a cyano, azido or rhodano group, for a radical —OR
10
or —SR
10
with R
10
standing for a hydrogen atom, an alkyl, aryl, aralkyl, or alkylaryl radical with 1-10 carbon atoms in each case or an acyl radical COR
9
, with R
9
standing for an alkyl, aryl, aralkyl, or alkylaryl radical with 1-10 carbon atoms in each case, a radical —OR
9
with R
9
standing for a hydrogen atom, an alkyl, aryl, aralkyl or alkylaryl radical with 1-10 carbon atoms in each case,
for a radical —(CH
2
)
m
—CH═CH(CH
2
)
n —R
8
with m=0, 1, 2 or 3 and n=0, 1 or 2, and R
8
stands for a hydrogen atom, an alkyl, aryl, aralkyl or alkylaryl radical with 1-10 carbon atoms in each case or a hydroxyl group, an alkoxy group or acyloxy group with 1-10 carbon atoms in each case,
a radical —(CH
2
)
o
C≡CR
11
with o=0, 1 or 2, and R
11
stands for a hydrogen atom, a fluorine, chlorine, bromine or iodine atom, an alkyl, aryl, aralkyl, alkylaryl or an acyl radical with 1-10 carbon atoms in each case,
R
1
and R
2
, independently of one another, stand for a keto, methylene, or difluoromethylene group,
there can be a double bond between C-6 and C-7,
an &agr;- or &bgr;-cyclopropane group X, indicated by X, that is shown standing for a CZ
2
group with Z standing for a hydrogen, fluorine, chlorine, bromine or iodine atom, is located between C-14 and C-15,
R
3
and R
4
, independently of one another, stand for a hydrogen atom, an &agr;- or &bgr;-position alkyl group with 1-10 carbon atoms,
R
5
stands for an alkyl group with 1-3 carbon atoms.
Most preferred are
17&bgr;-Hydroxy-14&agr;,15&agr;-methylen-androst-4-en-3-one (J 1193),
17&agr;-hydroxy-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&bgr;-hydroxy-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&agr;-hydroxy-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&agr;-methyl,17&bgr;-hydroxy-14&agr;,15&agr;-methylen-androst-4-ene-3-one,
17&bgr;-methyl,17&agr;-hydroxy-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&agr;-methyl,17&bgr;-hydroxy-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&bgr;-methyl,17&agr;-hydroxy-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&bgr;-hydroxy-6&agr;-methyl-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&agr;-hydroxy-6&agr;-methyl-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&bgr;-hydroxy-6&agr;-methyl-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&agr;-hydroxy-6&agr;-methyl-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&bgr;-hydroxy-7&agr;-methyl-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&agr;-hydroxy-7&agr;-methyl-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&bgr;-hydroxy-7&agr;-methyl-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&agr;-hydroxy-7&agr;-methyl-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&bgr;-hydroxy-14&agr;,15&agr;-methylen-androsta-4,6-dien-3-one,
17&agr;-hydroxy-14&agr;,15&agr;-methylen-androsta-4,6-dien-3-one,
17&bgr;-hydroxy-14&bgr;,15&bgr;-methylen-androsta-4,6-dien-3-one,
17&agr;-hydroxy-14&bgr;,15&bgr;-methylen-androsta-4,6-dien-3-one,
17&agr;-methyl,17&bgr;-hydroxy-14&agr;,15&agr;-methylen-androsta-4,6-dien-3-one,
17&bgr;-methyl,17&agr;-hydroxy-14&agr;,15&agr;-methylen-androsta-4,6-dien-3-one,
17&agr;-methyl,17&bgr;-hydroxy-14&bgr;,15&bgr;-methylen-androsta-4,6-dien-3-one,
17&bgr;-methyl,17&agr;-hydroxy-14&bgr;,15&bgr;-methylen-androsta-4,6-dien-3-one,
17&bgr;-hydroxy-7&agr;,17&agr;-dimethyl-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&agr;-hydroxy-7&agr;,17&bgr;-dimethyl-14&agr;,15&agr;-methylen-androst-4-en-3-one,
17&bgr;-hydroxy-7&agr;,17&agr;-dimethyl-14&bgr;,15&bgr;-methylen-androst-4-en-3-one,
17&agr;-hydroxy-7&agr;,17&bgr;-dimethyl-14&bgr;,15&bgr;-methylen-androst-4-en-3-one.
The invention also relates to a process for the production of the compounds according to general formula I and their pharmaceutically acceptable salts, which is characterized in that a compound of general formula II
in which R
1
, R
2
, R
3
and R
5
have the above-indicated meaning,
R
4
stands for a hydrogen atom, a hydroxy group, an alkoxyl group, an acyloxy group, an alkyl group with 1-10 carbon atoms in each case,
R
6
stands for a hydrogen atom, a hydroxy group, an alkoxyl group, an acyloxy group, an alkyl group with 1-10 carbon atoms in each case,
an &agr;- or &bgr;-cyclopropane group X, indicated by X, that is shown representing a CZ
2
group, in which Z can mean a hydrogen, fluorine, chlorine, bromine or iodine atom, is located between carbon atoms 14 and 15,
cleaves the 3,5-cyclopropane grouping with acids, whereby mineral acids, organic acids and Lewis acids are preferred, and then converts into the desired compounds of general formula I according to the methods that are known to one skilled in the art.
Subjects
Elger Walter
Kaufmann Günter
Ring Sven
Schneider Birgitt
Schwarz Sigfrid
Jenapharm GmbH & Co. KG.
Millen White Zelano & Branigan P.C.
Qazi Sabiha
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