Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2000-03-17
2003-07-01
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C514S063000, C546S014000, C546S015000, C549S214000, C549S215000, C568S808000
Reexamination Certificate
active
06586613
ABSTRACT:
The present invention relates to substituted tetrahydro-naphthalenes and analogous compounds, to processes for their preparation and to their use in pharmaceuticals.
7-(polysubstituted pyridyl)-6-heptenoates for the treatment of arteriosclerosis, lipoproteinaemia and hyperproteinaemia are known from the publication U.S. Pat. No. 5,169,857-A2. In addition, the preparation of 7-(4-aryl-3-pyridyl)-3,5-dihydroxy-6-heptenoates is described in the publication EP-325 130-A2.
The present invention relates to substituted tetrahydro-naphthalenes and analogous compounds of the general formula (I),
in which
A represents cycloalkyl having 3 to 8 carbon atoms, or represents aryl having 6 to 10 carbon atoms, or
represents a 5- to 7-membered saturated, partially unsaturated or unsaturated, optionally benzo-fused heterocycle having up to 4 heteroatoms selected from the group consisting of S, N and/or O,
where aryl and the abovementioned heterocyclic ring systems may optionally be substituted up to 5 times by identical or different substituents selected from the group consisting of cyano, halogen, nitro, carboxyl, hydroxyl, trifluoromethyl, trifluoromethoxy, or by straight-chain or branched alkyl, acyl, hydroxyalkyl, alkylthio, alkoxycarbonyl, oxyalkoxycarbonyl or alkoxy having in each case up to 7 carbon atoms, or by a group of the formula —NR
3
R
4
in which
R
3
and R
4
are identical or different and each represents hydrogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms,
D represents a radical of the formula
in which
R
5
, R
6
and R
9
independently of one another each represent cycloalkyl having 3 to 6 carbon atoms, or
aryl having 6 to 10 carbon atoms or a 5- to 7-membered, optionally benzo-fused, saturated or unsaturated, mono-, bi- or tricyclic heterocycle having up to 4 heteroatoms selected from the group consisting of S, N and/or O,
where the cycles are optionally, in the case of the nitrogen-containing rings also via the N-function, substituted up to 5 times by identical or different constituents selected from the group consisting of halogen, trifluoromethyl, nitro, hydroxyl, cyano, carboxyl, trifluoromethoxy, straight-chain or branched acyl, alkyl, alkylthio, alkylalkoxy, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, by aryl or trifluoromethyl-substituted aryl having in each case 6 to 10 carbon atoms or by an optionally benzo-fused aromatic 5- to 7-membered heterocycle having up to 3 heteroatoms selected from the group consisting of S, N and/or O,
and/or by a group of the formula —OR
10
, —SR
11
, —SO
2
R
12
or —NR
13
R
14
,
in which
R
10
, R
11
and R
12
independently of one another each represent aryl having 6 to 10 carbon atoms which for its part is substituted up to 2 times by identical or different substituents selected from the group consisting of phenyl, halogen or by straight-chain or branched alkyl having up to 6 carbon atoms,
R
13
and R
14
are identical or different and are as defined above for R
3
and R
4
,
or
R
5
and/or R
6
represents/represent a radical of the formula
R
7
represents hydrogen, halogen or methyl,
and
R
8
represents hydrogen, halogen, azido, trifluoromethyl, hydroxyl, trifluoromethoxy, straight-chain or branched alkoxy or alkyl having in each case up to 6 carbon atoms or a radical of the formula —NR
15
R
16
,
in which
R
15
and R
16
are identical or different and are as defined above for R
3
and R
4
,
or
R
7
and R
8
together form a radical of the formula ═O or ═NR
17
,
in which
R
17
represents hydrogen or straight-chain or branched alkyl, alkoxy or acyl having in each case up to 6 carbon atoms,
L represents a straight-chain or branched alkylene or alkenylene chain, having in each case up to 8 carbon atoms, which is optionally substituted up to 2 times by hydroxyl,
T and X are identical or different and each represents a straight-chain or branched alkylene chain having up to 8 carbon atoms,
or
T or X represents a bond,
V represents an oxygen or sulphur atom or represents a —NR
18
group,
in which
R
18
represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms or phenyl,
E represents cycloalkyl having 3 to 8 carbon atoms, or represents straight-chain or branched alkyl having up to 8 carbon atoms which is optionally substituted by cycloalkyl having 3 to 8 carbon atoms or hydroxyl, or represents phenyl, which is optionally substituted by halogen or trifluoromethyl,
R
1
and R
2
together form a straight-chain or branched alkylene chain, having up to 7 carbon atoms, which has to be substituted by a carbonyl group and/or by a radical of the formula
in which
a and b are identical or different and each represents a number 1, 2 or 3,
R
19
represents hydrogen, cycloalkyl having 3 to 7 carbon atoms, straight-chain or branched silylalkyl having up to 8 carbon atoms or straight-chain or branched alkyl having up to 8 carbon atoms which is optionally substituted by hydroxyl, straight-chain or branched alkoxy having up to 6 carbon atoms or by phenyl which for its part may be substituted by halogen, nitro, trifluoromethyl, trifluoromethoxy or by phenyl or tetrazole-substituted phenyl, and alkyl is optionally substituted by a group of the formula —OR
22
,
in which
R
22
represents straight-chain or branched acyl having up to 4 carbon atoms or benzyl,
or
R
19
represents straight-chain or branched acyl having up to 20 carbon atoms or benzoyl which is optionally substituted by halogen, trifluoromethyl, nitro or trifluoromethoxy, or straight-chain or branched fluoracyl having up to 8 carbon atoms and 9 fluorine atoms,
R
20
and R
21
are identical or different and each represents hydrogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms,
or
R
20
and R
21
together form a 3- to 6-membered carbocycle,
and the alkylene chain which is formed by R
1
and R
2
is optionally substituted up to 6 times, optionally also geminally, by identical or different substituents selected from the group consisting of trifluoromethyl, hydroxyl, nitrile, halogen, carboxyl, nitro, azido, cyano, cycloalkyl or cycloalkyloxy having in each case 3 to 7 carbon atoms, by straight-chain or branched alkoxycarbonyl, alkoxy or alkylthio having in each case up to 6 carbon atoms or by straight-chain or branched alkyl having up to 6 carbon atoms which for its part is substituted up to 2 times by identical or different substituents selected from the group consisting of hydroxyl, benzyloxy, trifluoromethyl, benzoyl, straight-chain or branched alkoxy, oxyacyl and carboxyl having in each case up to 4 carbon atoms and phenyl which for its part may be substituted by halogen, trifluoromethyl or trifluoromethoxy,
and/or the alkylene chain which is formed by R
1
and R
2
is optionally substituted, also geminally, up to 5 times by identical or different substituents selected from the group consisting of phenyl, benzoyl, thiophenyl and sulphonylbenzyl, which for their part are optionally substituted by halogen, trifluoromethyl, trifluoromethoxy or nitro,
and/or the alkylene chain formed by R
1
and R
2
is optionally substituted by a radical of the formula
in which
c represents a number 1, 2, 3 or 4,
d represents a number 0 or 1,
R
23
and R
24
are identical or different and each represents hydrogen, cycloalkyl having 3 to 6 carbon atoms, straight-chain or branched alkyl having up to 6 carbon atoms, benzyl or phenyl, which is optionally substituted up to 2 times by identical or different substituents selected from the group consisting of halogen, trifluoromethyl, cyano, phenyl and nitro,
and/or the alkylene chain formed by R
1
and R
2
is optionally substituted by a spiro-linked radical of the formula
in which
W represents either an oxygen or a sulphur atom,
Y and Y′ together form a 2- to 6-membered straight-chain or branched alkylene chain,
e represents a number 1, 2, 3, 4, 5, 6 or 7,
f represents a number 1 or 2,
R
25
, R
26
, R
27
, R
28
, R
29
, R
30
and R
31
Antons Stefan
Bischoff Hilmar
Brandes Arndt
Bremm Klaus-Dieter
Lögers Michael
Bayer Aktiengellschaft
Chiu Jerrie L.
Shaver Paul F.
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