C2-substituted indan-1-ols and their derivatives, processes...

Details C2-substituted indan-1-ols and their derivatives, processes... C2-substituted indan-1-ols and their derivatives, processes...

2002-08-30

2003-12-02

Vollano, Jean F. (Department: 1621)

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

Organic compounds

Sulfur containing

C568S034000, C568S035000, C564S084000, C564S086000, C560S017000, C562S030000, C562S037000

Reexamination Certificate

active

06657086

ABSTRACT:

This application claims the benefit of foreign priority under 35 U.S.C. §119 of German patent application no. 10142667.4, filed on Aug. 31, 2001, the contents of which are expressly incorporated by reference herein.
DESCRIPTION
C2-substituted indan-1-ols and their derivatives, processes for their preparation and their use as pharmaceuticals.
Other applications that describe similar compounds and methods of using these compounds include: 1) “Use of C2-substituted indan-1-one systems for preparing medicaments for the prophylaxis or treatment of obesity” of Gerhard Jaehne, Volker Krone, Martin Bickel, and Matthias Gossel filed Aug. 31, 2002, Attorney Docket Number 02481.1797; 2) “C2-substituted indan-1-ones and their derivatives, processes for their preparation and their use as pharmaceuticals” of Gerhard Jaehne, Volker Krone, Martin Bickel, and Matthias Gossel filed Aug. 31, 2002, Attorney Docket Number 02481.1795; and 3) “Use of C2-substituted indan-1-ol systems for preparing medicaments for the prophylaxis or treatment of obesity” of Gerhard Jaehne, Volker Krone, Martin Bickel, and Matthias Gossel filed Aug. 31, 2002, Attorney Docket Number 02481.1800; all of which are hereby incorporated by reference.
Embodiments of the invention relate to C2-substituted indan-1-ols and their derivatives and also their physiologically acceptable salts and physiologically functional derivatives.
EP 0009554 discloses indan-1-one and -1-ol derivatives as herbicides and analgesics.
EP 0313296 discloses indan-1-one and -1-ol derivatives as pharmaceuticals for asthma.
WO 97/20806 discloses cyclopentyl-substituted indan-1-one derivatives having inter alia antiinflammatory action.
In one embodiment, an object of the present invention is to provide compounds which can be used for reducing the weight in mammals and which are suitable for preventing and treating obesity.
Embodiments of the invention also relate to compounds of the formula (I)
in which
A)
R1 to R4 are H;
X is S, SO, or SO
2
;
Y is (CH
2
)
p
, where p is 0, 1, 2 or 3;
R5 is CF
3
, (C
2
-C
18
)-alkyl, (C
3
-C
4
)-cycloalkyl, or (C
6
-C
8
)-cycloalkyl, wherein the alkyl or cycloalkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
(CH
2
)
r
—COR6, where r is 1-6 and R6 is OH, O—(C
1
-C
6
)-alkyl or NH
2
;
CH
2
—CH(NHR7)—COR8, where R7 is H, C(O)—(C
1
-C
4
)-alkyl or C(O)O—(C
1
-C
4
)-alkyl and R8 is 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 unsubstituted or substituted one or 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, or (C
3
-C
8
)-cycloalkyl, wherein the alkyl or cycloalkyl groups in each case have zero to seven hydrogen atoms independently replaced by fluorine, or
F, Cl, Br, I, or CN;
with the proviso that R5 is not unsubstituted phenyl, 4-fluorophenyl, 4-bromophenyl, 4-chlorophenyl, 3-methylphenyl, 4-methylphenyl, 4-methoxyphenyl, 4-n-butylphenyl, 4-t-butylphenyl, 2-aminophenyl, 2-nitrophenyl or C
12
-alkyl;
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, or (C
2
-C
8
)-alkynyl, where in the alkyl, cycloalkyl, alkenyl and alkynyl groups in each case have zero to seven hydrogen atoms replaced by fluorine, or one hydrogen replaced by OH, OC(O)CH
3
, O—CH
2
—Ph, NH
2
, NH—CO—CH
3
or N(COOCH
2
Ph)
2
; or
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, or
3-, 4- or 5-isothiazolyl
where in each case the aryl radical or heterocycle is unsubstituted or substituted one or 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, or CO—NH
2
and wherein the alkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
R2, R3 independently of one another are
H, F, Cl, Br, I, CN, N
3
, NO
2
, 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
5
-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
5
-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
3
)-alkyl, (C
3
-C
8
)-cycloalkyl, (C
2
-C
8
)-alkenyl, or (C
2
-C
8
)-alkynyl, where in the alkyl, cycloalkyl, alkenyl and alkynyl groups in each case have zero to seven hydrogen atoms replaced by fluorine, or one hydrogen replaced by OH, OC(O)CH
3
, O—CH
2
—Ph, NH
2
, NH—CO—CH
3
or N(COOCH
2
Ph)
2
; or
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, or
3-, 4- or 5-isothiazolyl
where the heterocycle is unsubstituted or substituted one or 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, or CO—NH
2
wherein the alkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
or R2 and R3 together form the group —O—CH
2
—O—;
where in each case at least one of the radicals R1, R2, R3 and R4 is different from hydrogen;
X is S, SO, or SO
2
;
Y is (CH
2
)
p
, where p can be 0, 1, 2 or 3;
R5 is (C
1
-C
18
)-alkyl, or (C
3
-C
4
and C
6
-C
8
)-cycloalkyl, wherein the alkyl and cycloalkyl groups in each case have zero to seven hydrogen atoms replaced by fluorine;
(CH
2
)
r
—COR6, where r is 1-6 and R6 is OH, O—(C
1
-C
6
)-alkyl or NH
2
;
CH
2
—CH(NHR7)—COR8, where R7 is H, C(O)—(C
1
-C
4
)-alkyl or C(O)O—(C
1
-C
4
)-alkyl and R8 is 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 unsubstituted or substituted one or 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

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