Diphenyl derivatives

Details Diphenyl derivatives Diphenyl derivatives

2002-02-26

2004-08-17

Berch, Mark L (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S570000, C514S571000, C514S618000, C514S619000, C514S620000, C514S621000, C514S622000, C514S563000, C514S545000, C564S162000, C564S163000, C564S169000, C564S170000, C564S171000, C560S011000, C560S017000, C560S045000, C562S460000, C562S429000, C562S431000

Reexamination Certificate

active

06777442

ABSTRACT:

The invention relates to novel diphenyl derivatives, to processes for their preparation and to their use in medicaments.
EP-A-580 550 describes oxamic acid derivatives having cholesterol-lowering properties in mammals. The pharmacological property that is emphasized is the reduction of plasma cholesterol, in particular of LDL cholesterol. Cholesterol-lowering actions are also described in EP-A-188 351 for certain diphenyl ethers having thyroid-hormone-like actions.
Diphenyl ethers as thyroid receptor ligands are also disclosed in WO 99/00353 and WO 00/39077. Further diphenyl derivatives having thyroid-hormone-like properties are described in WO 98/57919, WO 99/26966 and WO 00/58279. Certain diphenyl sulphones are claimed in WO 00/72810 and WO 00/73265 for treating hair loss.
It is an object of the present invention to provide novel compounds having improved, in particular pharmaceutical, actions.
It has now been found that compounds of the general formula (I)
in which
X represents O, S, SO, SO
2
, CH
2
, CHF, CF
2
or represents NR
8
in which R
8
represents hydrogen or (C
1
-C
4
)-alkyl,
R
1
and R
2
are identical or different and represent hydrogen or (C
1
-C
4
)-alkyl,
R
3
and R
4
are identical or different and represent hydrogen, halogen, cyano, (C
1
-C
6
)-alkyl, CF
3
, CHF
2
, CH
2
F, vinyl or (C
3
-C
7
)-cycloalkyl, where at least one of the two substituents is not hydrogen,
R
5
represents hydrogen, (C
1
-C
4
)-alkyl or halogen,
R
6
represents a group of the formula —S—R
9
, —S(O)
n
—R
10
, —NR
11
—C(O)—R
12
, —CH
2
—R
13
or —M—R
14
, in which
R
9
represents (C
1
-C
10
)-alkyl, (C
3
-C
8
)-cycloalkyl, (C
2
-C
6
)-alkenyl, (C
6
-C
10
)-aryl, (C
6
-C
10
)-arylmethyl or represents a saturated, partially unsaturated or aromatic 5- to 10-membered heterocycle having up to four identical or different heteroatoms from the group consisting of N, O and S, where the abovementioned radicals are optionally substituted by one, two or three identical or different substituents selected from the group consisting of halogen, hydroxyl, oxo, cyano, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkoxy, carboxyl and (C
1
-C
4
)-alkoxycarbonyl,
n represents the number 1 or 2,
R
10
represents OR
15
, NR
16
R
17
, (C
1
-C
10
)-alkyl, (C
3
-C
8
)-cycloalkyl, (C
2
-C
6
)-alkenyl, (C
6
-C
10
)-aryl, (C
6
-C
10
)-arylmethyl or represents a saturated, partially unsaturated or aromatic 5- to 10-membered heterocycle having up to four identical or different heteroatoms from the group consisting of N, O and S, where the abovementioned radicals are optionally substituted by one, two or three identical or different substituents selected from the group consisting of halogen, hydroxyl, oxo, cyano, nitro, amino, NR
18
R
19
, trifluoromethyl, (C
1
-C
6
)-alkyl, optionally R
20
-substituted (C
1
-C
6
)-alkoxy, (C
3
-C
8
)-cycloalkyl, (C
6
-C
10
)-aryl, which for its part is optionally substituted by halogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, trifluoromethyl, nitro or cyano, —O—C(O)—R
21
, —C(O)—OR
22
, —C(O)—N
23
R
24
, —SO
2
—NR
25
R
26
, —NH—C(O)—R
27
and —NH—C(O)—OR
28
, where
R
15
, R
18
, R
19
, R
20
, R
21
, R
22
, R
23
, R
24
, R
25
, R
26
, R
27
and R
28
are identical or different and each represents hydrogen, phenyl, benzyl, (C
1
-C
6
)-alkyl or (C
3
-C
8
)-cycloalkyl which for their part are optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, hydroxyl, amino, carboxyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkoxycarbonylamino, (C
1
-C
5
)-alkanoyloxy, a heterocycle or by phenyl which for its part is optionally substituted by halogen or hydroxyl, and
R
16
and R
17
are identical or different and independently of one another represent hydrogen, straight-chain or branched (C
1
-C
6
)-alkyl which may be mono- or polysubstituted by identical or different substituents from the group consisting of mono-(C
1
-C
6
)-alkylamino, di-(C
1
-C
6
)-alkyl amino, (C
1
-C
4
)-alkoxy, (C
1
-C
6
)-alkoxycarbonyl, carboxyl, pyridyl or (C
6
-C
10
)-aryl, where the latter for its part is optionally substituted by halogen, trifluoromethyl, (C
1
-C
6
)-alkyl or (C
1
-C
6
)-alkoxy,
represent (C
3
-C
8
)-cycloalkyl or represent a 5- to 7-membered heterocycle which contains one or two nitrogen atoms, where cycloalkyl and heterocycle are optionally substituted by (C
1
-C
4
)-alkyl, or
R
16
and R
17
together with the nitrogen atom to which they are attached form a 5- to 7-membered saturated, optionally benzo-fused heterocycle which may contain up to two further heteroatoms from the group consisting of N, O and S and which may be substituted by amino, (C
1
-C
6
)-alkyl, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkoxycarbonylamino or phenyl,
R
11
represents hydrogen, straight-chain or branched (C
1
-C
6
)-alkyl which may be mono- or polysubstituted by identical or different substituents from the group consisting of mono-(C
1
-C
6
)-alkylamino, di-(C
1
-C
6
)-alkylamino, (C
1
-C
4
)-alkoxy, (C
1
-C
6
)-alkoxycarbonyl, carboxyl, pyridyl and (C
6
-C
10
)-aryl, where the latter for its part is optionally substituted by halogen, trifluoromethyl, (C
1
-C
6
)-alkyl or (C
1
-C
6
)-alkoxy, represents (C
3
-C
8
)-cycloalkyl or represents a 5- to 7-membered heterocycle which contains one or two nitrogen atoms, where cycloalkyl and heterocycle are optionally substituted by (C
1
-C
4
)-alkyl,
R
12
represents straight-chain or branched (C
1
-C
15
)-alkyl which may be substituted by (C
3
-C
8
)-cycloalkyl, (C
1
-C
4
)-alkoxy, phenyl, phenoxy or benzyloxy, where the aromatic radicals mentioned for their part may each be substituted up to three times by identical or different substituents from the group consisting of halogen, (C
1
-C
6
)-alkyl and (C
1
-C
4
)-alkoxy,
represents (C
3
-C
8
)-cycloalkyl which may be substituted by (C
1
-C
4
)-alkoxy or phenyl,
represents (C
6
-C
10
)-aryl which may be substituted up to three times by identical or different substituents from the group consisting of (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkoxy, halogen, cyano, amino, trifluoromethyl and phenyl, or
represents a 5- or 6-membered saturated or aromatic, optionally benzo-fused heterocycle having up to two heteroatoms from the group consisting of N, O and S, or
represents a group of the formula —OR
29
or —NR
30
R
31
, in which
R
29
represents straight-chain or branched (C
1
-C
6
)-alkyl, and
R
30
and R
31
are identical or different and independently of one another
represent hydrogen, straight-chain or branched (C
1
-C
12
)-alkyl which may be substituted by aminocarbonyl, a group of the formula —NR
32
R
33
, 5- or 6-membered heteroaryl which contains up to 3 heteroatoms selected from the group consisting of N, O and S, or by phenyl, where phenyl is optionally substituted up to two times by identical or different substituents from the group consisting of halogen, (C
1
-C
4
)-alkyl, trifluoromethyl and (C
1
-C
4
)-alkoxy,
represent (C
3
-C
8
)-cycloalkyl which may be substituted by (C
1
-C
4
)-alkyl,
represent (C
6
-C
10
)-aryl which may be substituted up to three times by identical or different substituents from the group consisting of halogen, (C
1
-C
4
)-alkyl, trifluoromethyl, (C
1
-C
4
)-alkoxy, amino, phenyl and phenoxy, or
represent a 5- to 7-membered saturated or unsaturated heterocycle which contains one or two nitrogen atoms and is optionally substituted by (C
1
-C
4
)-alkyl or an oxo group, where
R
32
and R
33
are identical or different and independently of one another represent hydrogen, (C
1
-C
6
)-alkyl, phenyl or (C
6
-C
10
)-arylsulphonyl, or
together with the nitrogen atom to which they are attached form a 3- to 7-membered saturated heterocycle which optionally contains up to two further heteroatoms from the group consisting of N, O and S or
R
30
and R
31
together with the nitrogen atom to which they are attached form a 4- to 7-membered saturated heterocycle which may contain up to two further heteroatoms from the group consisting of N, O and S and which may be substituted by amino, (C
1
-C
6
)-alkyl, (C
1
-C
4
)-alkanoyl, aminocarbonyl, (C
1
-C
4
)-alkox

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