Derivatives of C2-substituted indan-1-ol systems for the...

Details Derivatives of C2-substituted indan-1-ol systems for the... Derivatives of C2-substituted indan-1-ol systems for the...

2002-08-29

2003-12-23

Vollano, Jean F. (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Sulfur, selenium or tellurium compound

C568S033000, C568S034000, C564S340000, C562S041000, C562S405000, C514S602000

Reexamination Certificate

active

06667345

ABSTRACT:

RELATED APPLICATION DATA
The instant application takes priority from DE 10142660.7 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 C2-substituted indan-1-ol systems and their physiologically acceptable salts and physiologically functional derivatives for the prophylaxis or treatment of obesity.
2. Description of the Related Art
EP 0009554 discloses indan-1-one and -1-ol derivatives as herbicides and analgesics.
WO 97/20806 discloses cyclopentyl-substituted indan-1-one derivatives having inter alia antiinflammatory action.
SUMMARY OF THE INVENTION
The present invention provides, in a preferred embodiment, compounds which can be used to cause a reduction in weight in mammals and which, in particular, reveal a therapeutically exploitable anorectic action.
In another preferred embodiment, the invention provides a pharmaceutical composition comprising an effective amount of a compound of formula I and a pharmaceutically acceptable carrier. Preferably, the composition may further comprise one or more active compounds suitable for reducing weight. Also, the instant invention contemplates those compositions further comprising agents suitable in treating other disorders.
In another preferred embodiment, the invention provides a method for the treating obesity by administering to a subject in need thereof, an effective amount of a compound according to formula I.
In another preferred embodiment, the invention provides a method of reducing weight in a mammal, comprising administering to said mammal an effective amount of a compound of formula I.
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 relates to 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, 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, 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, (C
2
-C
8
) -alkenyl, (C
2
-C
8
)-alkynyl, where in the alkyl, alkenyl and alkynyl groups in each case 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 group —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 CF
3
, (C
1
-C
18
)-alkyl, (C
3
-C
8
)-cycloalkyl, where in the alkyl groups one to seven hydrogen atoms may be replaced by fluorine;
(CH
2
)
r
—COR6, where r=1-6 and R6 may be OH, O—(C
1
-C
6
)-alkyl or NH
2
;
CH
2
—CH(NHR7)—COR8, where R7 may be H or C(O)—(C
1
-C
4
)-alkyl and R8 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 may be substituted up to two 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
2
-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
-C8)-cycloalkyl, where in the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine;
R9 is (C
1
-C
12
)-alkyl, (C
3
-C
8
)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
CO—O(C
1
-C
6
)-alkyl, CO—O(C
3
-C
8
)-cycloalkyl, C(O)—(C
1
-C
8
)-alkyl, C(O)—(C
3
-C
8
)-cycloalkyl, C(O)-phenyl, C(O)—CH(NHR12)—(C
1
-C
8
)-alkyl, phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, where the aryl or heteroaryl radicals 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, —CH
2
—COOH, O—CH
2
—CO—O(C
1
-C
8
)-alkyl, COOH, CO—O—(C
1
-C
4
)-alkyl, CO—NH
2
;
(CH
2
)—R10;
(CH
2
)
s
—R11, where s=2 or 3;
R10 is (C
1
-C
12
)-alkyl, (C
3
-C
8
)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
COOH, CONH
2
, CO—O(C
1
-C
6
)-alkyl, CO—O(C
3
-C
8
)-cycloalkyl; phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, 2- or 3-furyl or 2- or 3-thienyl, where the aryl or heteroaryl radicals 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, O—CH
2
—COOH, O—CH
2
—CO—O (C
1
-C
8
)-alkyl, COOH, CO—O—(C
1
-C
4
)-alkyl, CO—NH
2
;
R11 is (C
1
-C
12
)-alkyl, (C
3
-C
8
)-cycloalkyl, where in the alkyl radicals one to seven hydrogen atoms may be replaced by fluorine;
COOH, CONH
2
, CO—O(C
1
-C
6
)-alkyl, CO—O(C
3
-C
8
)-cycloalkyl; phenyl, 1- or 2-naphthyl, biphenyl, 2-, 3- or 4-pyridyl, 2- or 3-furyl, 2- or 3-thienyl or 1-imidazolyl, where the aryl or heteroaryl radicals 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, O—CH
2
—COOH, O—CH
2
—CO—O (C
1
-C
8
)-alkyl, COOH, CO—O—(C
1
-C
4
)-alkyl, CO—NH
2
;
R12 is H, C(O)—(C
1
-C
6
)-alkyl;
and their physiologically acceptable salts.
In a preferred embodiment, the invention provides compounds of the formula I in which
R1, 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;
R2, R3 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 can be 0, 1, 2 or 3;
R5 is (C
1
-C
18
)-alkyl; (C
3
-C
4
- and C
6
-C
8
)-cycloalkyl, where in the alkyl groups one to seven hydrogen atoms may be replaced by fluorine;
(CH
2
)
r
COR6, where r&e

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