Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-03-08
2001-03-27
Seaman, D. Margaret (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S261100, C514S305000, C514S311000, C514S256000, C514S334000, C514S335000, C514S336000, C514S337000, C514S338000, C514S339000, C514S340000, C514S341000, C514S342000, C544S245000, C544S333000, C546S139000, C546S148000, C546S152000, C546S176000, C546S255000, C546S270100, C546S271700, C546S273400, C546S279700, C546S281700
Reexamination Certificate
active
06207671
ABSTRACT:
The present invention relates to cycloalkano-pyridines, processes for their preparation and their use in medicaments.
U.S. Pat. No. 5,169,857 A2 discloses 7-(polysubstituted pyridyl)-6-heptenoates for the treatment of arteriosclerosis, lipoproteinaemia and hyperlipoproteinaemia. The preparation of 7-(4-aryl-3-pyridyl)-3,5-dihydroxy-6-heptenoates is additionally described in the publication EP 325 130 A2. The compound 5(6H)-quinolone, 3-benzyl-7,8-dihydro-2,7,7-trimethyl-4-phenyl- is furthermore known from the publication Khim. Geterotsikl. Soedin. (1967), (6), 1118-1120.
The present invention relates to cycloalkano-pyridines of the general formula (I)
in which
A represents aryl having 6 to 10 carbon atoms, which is optionally substituted up to 5 times in an identical or different manner by halogen, nitro, hydroxyl, trifluoromethyl, trifluoromethoxy or by straight-chain or branched alkyl, acyl, hydroxyalkyl or alkoxy each having 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 denote hydrogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms,
D represents aryl having 6 to 10 carbon atoms, which is optionally substituted by phenyl, nitro, halogen, trifluoromethyl or trifluoromethoxy, or
represents a radical of the formula
in which
R
5
and R
6
and R
9
independently of one another denote cycloalkyl having 3 to 6 carbon atoms, or denote 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 from the series S, N and/or O, where the cycles are substituted, if appropriate, in the case of the nitrogen-containing rings also via the N function, up to 5 times in an identical or different manner by halogen, trifluoromethyl, nitro, hydroxyl, cyano, carboxyl, trifluoromethoxy, straight-chain or branched acyl, alkyl, alkylthio, alkylalkoxy, alkoxy or alkoxycarbonyl each having up to 6 carbon atoms, by aryl- or trifluoromethyl-substituted aryl each having 6 to 10 carbon atoms or by an optionally benzo-fused, aromatic 5- to 7-membered heterocycle having up to 3 heteroatoms from the series S, N and/or O, and/or are substituted 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 denote aryl having 6 to 10 carbon atoms, which for its part is substituted up to 2 times in an identical or different manner by 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 have the meaning of R
3
and R
4
indicated above,
or
R
5
and/or R
6
denote a radical of the formula
R
7
denotes hydrogen or halogen
and
R
8
denotes hydrogen, halogen, azido, trifluoromethyl, hydroxyl, trifluoromethoxy, straight-chain or branched alkoxy or alkyl each having 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 have the meaning of R
3
and R
4
indicated above,
or
R
7
and R
8
together form a radical of the formula ═O or ═NR
17
,
in which
R
17
denotes hydrogen or straight-chain or branched alkyl, alkoxy or acyl each having up to 6 carbon atoms,
L denotes a straight-chain or branched alkylene or alkenylene chain each having up to 8 carbon atoms, each of which is optionally substituted up to 2 times by hydroxyl,
T and X are identical or different and denote a straight-chain or branched alkylene chain having up to 8 carbon atoms,
or
T or X denotes a bond,
V represents an oxygen or sulphur atom or an —NR
18
group,
in which
R
18
denotes 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 must be substituted by a carbonyl group and/or by a radical of the formula
in which
a and b are identical or different and denote a number 1, 2 or 3,
R
19
denotes 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 can 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
denotes straight-chain or branched acyl having up to 4 carbon atoms or benzyl,
or
R
19
denotes straight-chain or branched acyl having up to 20 carbon atoms or benzoyl which is optionally substituted by halogen, trifluoromethyl, nitro or trifluoromethoxy, or denotes straight-chain or branched fluoroacyl having up to 8 carbon atoms and 9 fluorine atoms,
R
20
and R
21
are identical or different, and denote 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, if appropriate also geminally, the carbocycles formed are optionally substituted up to 6 times in an identical or different manner by trifluoromethyl, hydroxyl, halogen, carboxyl, nitro, azido, cyano, cycloalkyl or cycloalkyloxy each having 3 to 7 carbon atoms, by straight-chain or branched alkoxycarbonyl, alkoxy or alkylthio each having 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 in an identical or different manner by hydroxyl, benzyloxy, trifluoromethyl, benzoyl, straight-chain or branched alkoxy, oxyacyl or carboxyl each having up to 4 carbon atoms and/or phenyl, which for its part can be substituted by halogen, trifluoromethyl or trifluoromethoxy,
and/or the carbocycles formed, also geminally, are optionally substituted up to 5 times in an identical or different manner by phenyl, benzoyl, thiophenyl or sulphonylbenzyl, which for their part are optionally substituted by halogen, trifluoromethyl, trifluoromethoxy or nitro,
and/or are optionally substituted by a radical of the formula
in which
c denotes a number 1, 2, 3 or 4,
d denotes a number 0 or 1,
R
23
and R
24
are identical or different and denote 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 in an identical or different manner by halogen, trifluoromethyl, cyano, phenyl or nitro,
and/or the carbocycles formed are optionally substituted by a spiro-linked radical of the formula
in which
W either denotes an oxygen or a sulphur atom,
Y and Y′ together form a 2- to 6-membered straight-chain or branched alkylene chain,
e denotes a number 1, 2, 3, 4, 5, 6 or 7,
f denotes a number 1 or 2,
R
25
, R
26
, R
27
, R
28
, R
29
, R
30
and R
31
are identical or different and denote hydrogen, trifluoromethyl, phenyl, halogen or straight-chain or branched alkyl or alkoxy each having up to 6 carbon atoms,
or
R
25
and R
26
or R
27
and R
28
in each case together form a straight-chain or branched alkyl chain having up to 6 carbon atoms,
or
R
25
and R
26
or R
27
and R
28
in each case together form a radical of the
in which
W has the meaning indicated above,
g denotes a number 1, 2, 3, 4, 5, 6 or 7,
R
32
and R
33
together form a 3- to 7-membered heterocycle which contains an oxygen or sulphur atom or a group of the formula SO, SO
2
or —NR
34
,
in which
R
34
denotes hydrogen, phenyl, benzyl or straight-chain or branched alkyl having up to 4 carbon atoms,
and their salts and N-oxides, with the exception of 5(6H)-quinolone, 3-benzoyl-7,8-dihydro-2,7,7-trimethyl-4-phenyl-.
The a
Angerbauer Rolf
Bischoff Hilmar
Brandes Arndt
Bremm Klaus-Dieter
Conrad Michael
Bayer Aktiengesellschaft
Norris & McLaughlin & Marcus
Seaman D. Margaret
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