Polysubstituted indan-1-ol compounds, and methods for their...

Details Polysubstituted indan-1-ol compounds, and methods for their... Polysubstituted indan-1-ol compounds, and methods for their...

2002-08-30

2003-12-30

Vollano, Jean F. (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Sulfur, selenium or tellurium compound

C568S034000, C564S340000, C562S041000, C562S405000, C514S601000, C514S602000

Reexamination Certificate

active

06670401

ABSTRACT:

RELATED APPLICATION DATA
The instant application takes priority from DE 10142661.5 filed Aug. 31, 2001 which is incorporated herein by reference in its entirety.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to substituted indan-1-old systems and also their physiologically acceptable salts and physiologically functional derivatives.
2. Description of the Related Art
WO 97/20806 discloses cyclopentyl-substituted indan-1-ol derivatives as antiinflammatory substances.
SUMMARY OF THE INVENTION
In a preferred embodiment, the invention provides compounds which can be used for reducing weight in mammals. The instant compounds have a therapeutically exploitable anorectic action.
In another preferred embodiment, the invention provides a pharmaceutical composition comprising one or more compounds of the instant invention and a pharmaceutically acceptable carrier. The compositions may comprise one or more active compounds for reducing weight in mammals.
In another preferred embodiment, the invention provides a method for reducing weight in mammals, comprising administering to said mammal an effective amount of a compound of the instant invention.
In another preferred embodiment, the invention provides a method of treating obesity, comprising administering to a subject in need thereof, an effective amount of a compound of the instant invention.
In another preferred embodiment, the invention provides a method of treating type II diabetes, comprising administering to a subject in need thereof, an effective amount of a compound of the instant invention.
In another preferred embodiment, the invention provides a method of maintaining weight loss, comprising administering to a subject in need thereof, an effective amount of a compound of the instant invention.
The methods may further comprise administering one or more active compounds for reducing weight in mammals.
Additional objects, features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The objects, features and advantages of the invention may be realized and obtained by means of the instrumentalities and combinations particularly pointed out in the appended claims.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention provides compounds of the formula (I)
in which
R1, R2, R3, R4 independently of one another are H; F, Cl, Br, I, CN, N
3
, NO
2
, OH, O(C
1
-C
8
)-alkyl, O(C
3
-C
8
)-cycloalkyl, O—CH
2
-phenyl, O-phenyl, O—CO—(C
1
-C
8
)-alkyl, O—CO—(C
3
-C
8
)-cycloalkyl, where in the alkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
S(O)
0-2
(C
1
-C
8
)-alkyl, S(O)
0-2
(C
3
-C
8
)-cycloalkyl, where in the alkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
NH
2
, NH—(C
1
-C
8
)-alkyl, NH—(C
3
-C
8
)-cycloalkyl, N[(C
1
-C
8
)-alkyl]
2
, N[(C
3
-C
8
)-cycloalkyl]
2
, NH—CO—(C
1
-C
8
)-alkyl, NH—CO—(C
3
-C
8
)-cycloalkyl;
SO
3
H, SO
2
—NH
2
, SO
2
—NH—(C
1
-C
8
)-alkyl, SO
2
—NH—(C
3
-C
8
)-cycloalkyl;
SO
2
—(C
1
-C
6
)-alkyl;
NH—SO
2
—NH
2
; NH—SO
2
—(C
1
-C
8
)-alkyl, NH—SO
2
—(C
3
-C
8
)-cycloalkyl;
O—CH
2
—COOH, O—CH
2
—CO—O(C
1
-C
8
)-alkyl, COOH, COO(C
1
-C
8
)-alkyl, CO—O—(C
3
-C
8
)-cycloalkyl, CO—NH
2
, CO—NH(C
1
-C
8
)-alkyl, CO—N[(C
1
-C
8
)-alkyl]
2
;
(C
1
-C
8
)-alkyl, (C
3
-C
8
)cycloalkyl, (C
2
-C
8
)-alkenyl, (C
2
-C
8
)-alkynyl, where in the alkyl, alkenyl and alkynyl groups one to seven hydrogen atoms may be replaced by fluorine;
or one hydrogen may be replaced by OH, OC(O)CH
3
, O—CH
2
—Ph,
NH
2
, NH—CO—CH
3
or N(COOCH
2
Ph)
2
;
phenyl, 1- or 2-naphthyl,
5-tetrazolyl, 1-[(C
1
-C
6
)-alkyl]-5-tetrazolyl, 2-[(C
1
-C
6
)-alkyl]-5-tetrazolyl,
1-imidazolyl,
1- or 4-[1,2,4]-triazolyl,
2- or 3-thienyl,
2- or 3-furyl,
2-, 3- or 4-pyridyl,
2-, 4- or 5-oxazolyl,
3-, 4- or 5-isoxazolyl,
2-, 4- or 5-thiazolyl,
3-, 4- or 5-isothiazolyl,
 where the aryl radical or heterocycle may be substituted up to two times by
F, Cl, Br, CN,
OH, (C
1
-C
4
)-alkyl, CF
3
, O—(C
1
-C
4
)-alkyl,
S(O)
0-2
(C
1
-C
6
)-alkyl, NH
2
, NH—SO
2
—(C
1
-C
4
)-alkyl;
COOH, CO—O—(C
1
-C
4
)-alkyl, CO—NH
2
and where in the alkyl groups one to seven hydrogen atoms may be replaced by fluorine; or
R2 and R3 together form the radical —O—CH
2
—O—;
x is S, SO, SO
2
;
Y is (CH
2
)
p
, where p may be 0, 1, 2 or 3;
R5 is (C
1
-C
18
)-alkyl, (C
3
-C
4
)-cycloalkyl, (C
6
-C
8
)-cycloalkyl,
where in the alkyl groups up to seven hydrogen atoms may be replaced by fluorine;
(CH
2
)
1-6
—COOH, (CH
2
)
1-6
—COO—(C
1
-C
6
)-alkyl, (CH
2
)
1-6
—CONH
2
;
CH
2
—CH(NHR10)-COR11, where R10 may be H or C(O)—(C
1
-C
6
)-alkyl and R11 may be OH, O—(C
1
-C
6
)-alkyl or NH
2
;
phenyl, 1- or 2-naphthyl, biphenyl, or a heterocyclic radical, where the rings or ring systems are in each case substituted up to three times by
F, Cl, Br, I, CN, OH, O(C
1
-C
8
)-alkyl, O(C
3
-C
8
)-cycloalkyl, O—CO—(C
1
-C
8
)-alkyl, O—CO—(C
3
-C
8
)-cycloalkyl, S(O)
0-2
(C
1
-C
8
)-alkyl, S(O)
0-2
(C
3
-C
8
)-cycloalkyl, NH
2
, NH—(C
1
-C
8
)-alkyl, NH—(C
3
-C
8
)-cycloalkyl, N[(C
1
-C
8
)-alkyl]
2
, N[(C
3
-C
8
)-cycloalkyl]
2
, NH—CO—(C
1
-C
8
)-alkyl, NH—CO—(C
3
-C
8
)-cycloalkyl, SO
3
H; SO
2
—NH
2
, SO
2
—NH—(C
1
-C
8
)-alkyl, SO
2
—NH—(C
3
-C
8
)-cycloalkyl, NH—SO
2
—NH
2
; NH—SO
2
—(C
1
-C
8
)-alkyl, NH—SO
2
—(C
3
-C
8
)-cycloalkyl; O—CH
2
—COOH, O—CH
2
—CO—O(C
1
-C
8
)-alkyl, COOH, CO—O(C
1
-C
8
)-alkyl, CO—O—(C
3
-C
8
)-cycloalkyl, CO—NH
2
, CO—NH(C
1
-C
8
)-alkyl, CO—N[(C
1
-C
8
)-alkyl]
2
;
(C
1
-C
8
)-alkyl, (C
3
-C
8
)-cycloalkyl, where in the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine;
R6 is (CH
2
)
0-6
—R9, (CH
2
)
0-6
—COOH, (CH
2
)
0-6
—COO—(C
1
-C
6
)-alkyl, (CH
2
)
0-6
—CONH
2
, (CH
2
)
0-6
—CH(NHR15)—COR16, F, Cl, Br, CN, (C
1
-C
18
)-alkyl, (C
3
-C
4
)-cycloalkyl, (C
6
-C
8
)-cycloalkyl, where in the alkyl radicals or cycloalkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
R15 is H, C(O)—(C
1
-C
6
)-alkyl;
R16 is OH, O—(C
1
-C
6
)-alkyl, NH
2
;
R7 is (CH
2
)
0-4
—R12, H, (C
1
-C
12
)-alkyl, (C
3
-C
4
)-cycloalkyl, (C
6
-C
8
)-cycloalkyl, COO(C
1
-C
6
)-alkyl, COO(C
3
-C
8
)-cycloalkyl, where in the alkyl radicals or cycloalkyl radicals up to seven hydrogen atoms may be replaced by fluorine;
R8 is (CH
2
)
0-4
—R14, (C
1
-C
12
)-alkyl, (C
3
-C
4
)-cycloalkyl, (C
6
-C
8
) cycloalkyl, where in the alkyl or cycloalkyl radicals up to seven hydrogen atoms may be replaced by fluorine atoms;
R9, R12, R14 independently of one another are
phenyl, 1- or 2-naphthyl, biphenyl, or a heterocyclic radical, where the rings or ring systems are in each case substituted up to three times by
F, Cl, Br, I, CN, OH, O(C
1
-C
8
)-alkyl, O(C
3
-C
8
)-cycloalkyl, O—CO—(C
1
-C
8
)-alkyl, O—CO—(C
3
-C
8
)-cycloalkyl, S(O)
0-2
(C
1
-C
8
)-alkyl, S(O)
0-2
(C
3
-C
8
)-cycloalkyl, NH
2
, NH—(C
1
-C
8
)-alkyl, NH—(C
3
-C
8
)-cycloalkyl, N[(C
1
-C
8
)-alkyl]
2
, N[(C
3
-C
8
)-cycloalkyl]
2
, NH—CO—(C
1
-C
8
)-alkyl, NH—CO—(C
3
-C
8
)-cycloalkyl, SO
3
H; SO
2
—NH
2
, SO
2
—NH—(C
1
-C
8
)-alkyl, SO
2
—NH—(C
3
-C
8
)-cycloalkyl, NH—SO
2
—NH
2
; NH—SO
2
—(C
1
-C
8
)-alkyl, NH—SO
2
—(C
3
-C
8
)-cycloalkyl; O—CH
2
—COOH, O—CH
2
—CO—O(C
1
-C
8
)-alkyl, COOH, CO—O(C
1
-C
8
)-alkyl, CO—O—(C
3
-C
8
)-cycloalkyl, CO—NH
2
, CO—NH(C
1
-C
8
)-alkyl, CO—N[(C
1
-C
8
)-alkyl]
2
;
(C
1
-C
8
)-alkyl, (C
3
-C
8
)-cycloalkyl, where in the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine;
and their physiologically acceptable salts.
Preferably, the instant invention provides compounds of the formula I in which
R1, R2, R3, R4 independently of one another are H, F, Cl, Br, N
3
, O(C
1
-C
8
)-alkyl, (C
1
-C
8
)-alkyl and where in the alkyl groups one to seven hydrogen atoms may be replaced by fluorine;
where in each case at least one of the radicals R1, R2, R3 and R4 is different from hydrogen;
X is S, SO, SO
2
;
Y is (CH
2
)p, where p may b

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