Derivatives of C2-substituted indan-1-ol compounds, methods...

Details Derivatives of C2-substituted indan-1-ol compounds, methods... Derivatives of C2-substituted indan-1-ol compounds, methods...

2002-08-30

2004-04-06

Jones, Dwayne C. (Department: 1614)

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfonic acids or salts thereof

C562S040000, C562S041000, C514S601000, C514S602000, C514S866000, C568S028000, C568S030000, C568S031000, C568S032000, C568S038000, C568S051000, C568S052000, C568S053000

Reexamination Certificate

active

06717008

ABSTRACT:

RELATED APPLICATION DATA
The instant application takes priority from DE 10142662.3-43 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 derivatives of C2-substituted indan-1-ol compounds and also their physiologically acceptable salts and physiologically functional derivatives.
2. Description of the Related Art
E. I. Gritsenko et al. (J. Org. Chem. USSR (English translation) 20, 673-678 (1984)) disclose the preparation of 1-methoxy-2-methylsulfanylindane.
1-Acetoxy-2-(4-chlorophenyl)sulfinylindane is disclosed as an intermediate by H. H. Szmant et al., J. Org. Chem. 43, 1835-37 (1978).
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
In a preferred embodiment, the present invention provides compounds which cause a reduction in weight in mammals and which are suitable for preventing and treating obesity.
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 instant invention relates to compounds of the formula (I)
in which
A) R1 to R4 are H;
X is S, SO, SO
2
;
Y is (CH
2
)
p
, where p can be 0, 1, 2 or 3;
R5 is CF
3
; (C
1
-C
18
)-alkyl; (C
3
-C
4
)-cycloalkyl, (C
6
-C
8
)-cycloalkyl, where in the alkyl groups one to seven hydrogen atoms can be replaced by fluorine;
(CH
2
)
r
—COR6, where r=1-6 and R6 can be OH, O—(C
1
-C
6
)-alkyl or NH
2
;
CH
2
—CH(NHR7)—COR8, where R7 can be H or C(O)—(C
1
-C
4
)-alkyl and R8 can 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 can be substituted up to two times by 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
-C
8
)-cycloalkyl, where in the alkyl groups in each case one to seven hydrogen atoms may be replaced by fluorine, F, Cl, Br, I, CN;
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;
except for the compounds where simultaneously
R1, R2, R3, R4=H, X═S, Y=a bond, R5=CH
3
, R9=CH
3
or
R1, R2, R3, R4=H, X═SO, Y=a bond, R5=4-chlorophenyl, R9=acetyl; or
B) R1, 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
4
and C
6
-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, 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 in the alkyl groups one to seven hydrogen atoms may be replaced by fluorine;
R2, R3 independen

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