Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-08-30
2003-09-23
Ramsuer, Robert W. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S236000
Reexamination Certificate
active
06624185
ABSTRACT:
CROSS-REFERENCE TO RELATED APPLICATIONS
The present application claims priority under 35 U.S.C. §119 of German Application Nos. 10142734.4 and 10223273.3, filed Aug. 31, 2001 and May 24, 2002, respectively, the disclosures of which are expressly incorporated by reference herein.
DESCRIPTION
1. Field of the Invention
The invention relates to diarylcycloalkyl derivatives and to their physiologically acceptable salts and physiologically functional derivatives.
2. Background of the Invention
Compounds of similar structure have already been described in the prior art for the treatment of hyperlipidemia and diabetes (PCT/US/0011490).
SUMMARY OF THE INVENTION
An object of the invention is to provide compounds having a therapeutically exploitable triglyceride-lowering action and a favorable effect on lipid and carbohydrate metabolism, such as for syndromes of dyslipidemias, type II diabetes and the metabolic syndrome/syndrome X. Another object of the invention is to provide compounds having improved action compared with the compounds of PCT/US00/14490. The compounds of the invention may activate the PPAR&agr; receptor.
In one aspect, the present invention is directed to a compound of formula I
in which
Ring A is (C
3
-C8)-cycloalkyl or (C
3
-C
8
)-cycloalkenyl where, in the cycloalkyl or cycloalkenyl rings, one or more carbon atoms may be replaced by oxygen atoms;
R1, R2, R4, R5 independently of one another are H, F, Cl, Br, OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl or O-(C
1
-C
6
)-alkyl;
R3 is H or (C
1
-C
6
)-alkyl;
x is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
Y is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
and its physiologically acceptable salts.
In another aspect, the present invention is directed to a compound of formula Ia
wherein
Ring A is cyclohexyl;
R1, R2 independently of one another are H, F, Cl, Br, OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl or O-(C
1
-C
6
)-alkyl;
R3 is H or (C
1
-C
6
)-alkyl;
X is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
Y is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms; and its physiologically acceptable salts.
In another aspect, the present invention is directed to a pharmaceutical, comprising at least one of the above compounds or physiologically acceptable salts and a pharmaceutically acceptable carrier.
In still another aspect, the present invention is directed to a pharmaceutical, comprising at least one of the above compounds or physiologically acceptable salts, at least one further active compound, and a pharmaceutically acceptable carrier.
In yet another aspect, the present invention is directed to a pharmaceutical, comprising at least one of the above compounds or physiologically acceptable salts, at least one lipid- or triglyceride-lowering active compound, and a pharmaceutically acceptable carrier.
The present invention is also directed to a method of treating a lipid metabolism disorder, type II diabetes, syndrome X, disturbed glucose tolerance, eating disorders, obesity, cardiomyopathy, cardiac insufficiency, osteoporosis, atherosclerosis, Alzheimer's disease, or inflammation, comprising administering to a host in need of such treatment an effective amount of at least one the above compounds or physiologically acceptable salts.
In another aspect, the present invention is directed to a method of treating a lipid metabolism disorder, type II diabetes, or syndrome X, comprising administering to a host in need of such treatment an effective amount of a combination of at least one of the above compounds or physiologically acceptable salts and at least one further active compound.
In another aspect, the present invention is directed to a process for preparing a pharmaceutical, comprising mixing at least one of the above compounds or physiologically acceptable salts with a pharmaceutically acceptable carrier to form a mixture and bringing this mixture into a form suitable for administration to form the pharmaceutical.
DESCRIPTION OF THE INVENTION
The particulars shown herein are by way of example and for purposes of illustrative discussion of the various embodiments of the present invention only and are presented in the cause of providing what is believed to be the most useful and readily understood description of the principles and conceptual aspects of the invention. In this regard, no attempt is made to show details of the invention in more detail than is necessary for a fundamental understanding of the invention, the description making apparent to those skilled in the art how the several forms of the invention may be embodied in practice.
Unless otherwise stated, a reference to a compound or component, includes the compound or component by itself, as well as in combination with other compounds or components, such as mixtures of compounds.
The invention relates to compounds of formula I
in which
Ring A is (C
3
-C
8
)-cycloalkyl or (C
3
-C
8
)-cycloalkenyl where, in the cycloalkyl or cycloalkenyl rings, one or more carbon atoms may be replaced by oxygen atoms;
R1, R2, R4, R5 independently of one another are H, F, Cl, Br, OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl or O-(C
1
-C
6
)-alkyl;
R3 is H or (C
1
-C
6
)-alkyl;
X is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
Y is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
and their physiologically acceptable salts.
The invention also includes compounds of formula I in which
Ring A is (C
3
-C
8
)-cycloalkyl or (C
3
-C
8
)-cycloalkenyl where, in the cycloalkyl or cycloalkenyl rings, one or more carbon atoms may be replaced by oxygen atoms;
R1, R2, R4 independently of one another are H, F, Cl, Br, OH, NO
2
, CF3, OCF
3
, (C
1
-C
6
)-alkyl or O-(C
1
-C
6
)-alkyl;
R5 is (C
1
-C
6
)-alkyl;
R3 is H or (C
1
-C
6
)-alkyl;
X is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
Y is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
and their physiologically acceptable salts.
The invention further includes compounds of formula I in which
Ring A is (C
3
-C
8
)-cycloalkyl or (C
3
-C
8
)-cycloalkenyl;
R1, R2 independently of one another are H, F, Cl, Br, OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl or O-(C
1
-C
6
)-alkyl;
R3 is H or (C
1
-C
6
)-alkyl;
X is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
Y is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
and their physiologically acceptable salts.
The invention also includes compounds of formula Ia
wherein
Ring A is cyclohexyl;
R1, R2 independently of one another are H, F, Cl, Br, OH, NO
2
, CF
3
, OCF
3
, (C
1
-C
6
)-alkyl or O-(C
1
-C
6
)-alkyl;
R3 is H or (C
1
-C
6
)-alkyl;
X is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
Y is (C
1
-C
6
)-alkyl where, in the alkyl group, one or more carbon atoms may be replaced by oxygen atoms;
and their physiologically acceptable salts.
The invention embraces compounds of formula I in the form of their racemates, racemic mixtures and pure enantiomers, and also their diastereomers and mixtures thereof.
The alkyl radicals in the substituents R1, R2, R3, R4 and R5 can be straight-chain or branched.
Pharmaceutically acceptable salts are suitable for medical applications because of their greater solubility in water compared with the starting or base compounds. These salts must have a pharmaceutically acceptable anion or cation. Suitable pharmaceutically acceptable acid addition salts of the compounds of the invention are salts of inorganic acids such as hydrochloric acid, hydrobromic, phosphoric, metaphosphoric, nitric and sulfuric acids, and of organic acids such as, for example, acetic acid, benze
Falk Eugen
Frick Wendelin
Glombik Heiner
Keil Stefanie
Schäfer Hans-Ludwig
Aventis Pharma Deutschland GmbH
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Ramsuer Robert W.
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