Use of polycyclic 2-aminothiazole systems for the treatment...

Details Use of polycyclic 2-aminothiazole systems for the treatment... Use of polycyclic 2-aminothiazole systems for the treatment...

2000-02-10

2002-11-05

Webman, Edward J. (Department: 1617)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S909000, C424S451000, C424S464000, C424S474000, C424S436000

Reexamination Certificate

active

06476059

ABSTRACT:

BACKGROUND OF THE INVENTION
The invention relates to the use of polycyclic 2-aminothiazole systems and of their physiologically tolerated salts and physiologically functional derivatives for producing medicines for the prophylaxis or treatment of obesity.
2-Aminothiazole systems are described as anti-inflammatory substances in R. Gupta et al., Indian J. Pharm. Sci. 1991, 53, 245-248.
The invention was based on the object of providing compounds which display a therapeutically utilizable anorectic effect.
SUMMARY OF THE INVENTION
The invention relates to a method for the treatment of obesity comprising administering to a patient in need of such treatment a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of formula I:
in which
Y is a direct linkage, CH
2
or CH
2
—CH
2
;
X is CH
2
, O, NH, NR6 or S;
R1, R1′ are independently H, F, Cl, Br, I, CF
3
, CN, NO
2
, COOH, COO(C
1
-C
6
)alkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]
2
, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, O—(C
1
-C
6
)-alkyl (where one, more than one or all hydrogen(s) in the alkyl, alkenyl and alkynyl radicals may be replaced by fluorine, or one hydrogen may be replaced by OH, OC(O)CH
3
, OC(O)H, O—CH
2
—Ph, NH
2
, NH—CO—CH
3
or N(COOCH
2
Ph)
2
), SO
2
—NH
2
, SO
2
NH(C
1
-C
6
)-alkyl, SO
2
N[(C
1
-C
6
)-alkyl]
2
, S—(C
1
-C
6
)-alkyl, S—(CH
2
)
n
-phenyl, SO—(C
1
-C
6
)-alkyl, SO—(CH
2
),-phenyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—(CH
2
)
n
-phenyl (where n is 0-6 and the phenyl radical may be optionally substituted up to two times by F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl or NH
2
), NH
2
, NH—(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, NH(C
1
-C
7
)-acyl, phenyl, biphenylyl, O—(CH
2
)
n
-phenyl (where n is 0-6), 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl, 2- or 3-thienyl (wherein the phenyl, biphenylyl, naphthyl, pyridyl, furanyl or thienyl rings may be optionally substituted up to 3 times by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), 1,2,3-triazol-5-yl (wherein triazol ring may be optionally substituted in position 1, 2 or 3 by methyl or benzyl) or tetrazol-5-yl (wherein the tetrazol ring may be optionally substituted in position 1 or 2 by methyl or benzyl);
R2 is NH
2
, NHR3 or NR4R5, wherein
R3 is (C
1
-C
6
)alkyl, CN, CHO, CO—NH
2
, CH═NH, C(S)—NH
2
, C(═NH)—NH-phenyl (wherein the phenyl ring may be optionally substituted up to two times by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C1-C6)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), phenyl, CH
2
-phenyl (wherein the phenyl ring may be optionally substituted up to 3 times by F, Cl, Br, I, OH, NO
2
, CN, OCF
3
, O—(C
2
-C
6
)-alkyl, (C
2
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), biphenylyl, 1- or 2-naphthyl, 4-pyridyl, 2- or 3-furanyl, 2- or 3- thienyl, 5-tetrazolyl (wherein the biphenylyl, naphthyl, pyridyl, furanyl or thienyl rings may be optionally substituted up to two times by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-6
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), CH
2
-phenyl, CH
2
-2-pyridyl or CH
2
-4-pyridyl (wherein the phenyl or pyridyl ring may be optionally substituted once or twice by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
);
R4 is C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl, phenyl or CH
2
-phenyl (wherein the phenyl ring may be optionally substituted once or twice by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
);
R5 is H, C
1
-C
6
)-alkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl, phenyl or CH
2
-phenyl (wherein the phenyl ring may be optionally substituted once or twice by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
) or
R4 and R5 together form one of the groups CH
2
—CH
2
—CH
2
—CH
2
CH
2
, CH
2
—CH
2
—N(CH
3
)—CH
2
—CH
2
, CH
2
—CH
2
—N(CH
2
-phenyl)—CH
2
—CH
2
, CH
2
—CH
2
—O—CH
2
—CH
2
or CH
2
—CH
2
—CH
2
—CH
2
;
R6 is (C
1
-C
6
)alkyl, acyl, (C═O)—(C
1
-C
6
)alkyl, (C═O)-(C
3
-C
6
)-cycloalkyl, phenyl, naphthyl, pyridyl, —SO
2
-phenyl, or SO
2
-naphthyl;
and their physiologically tolerated salts and physiologically functional derivatives.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention is directed to a method of treating obesity which encompasses prophylaxis and amelioration of obesity comprising administering to a patient in need thereof a pharmaceutical composition comprising a compound of formula I:
in which
Y is a direct linkage, CH
2
or CH
2
—CH
2
;
X is CH
2
, O, NH, NR6 or S;
R1, R1′ are independently H, F, Cl, Br, I, CF
3
, CN, NO
2
, COOH, COO(C
1
-C
6
)alkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]
2
, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, O—(C
1
-C
6
)-alkyl (where one, more than one or all hydrogen(s) in the alkyl, alkenyl and alkynyl radicals may be replaced by fluorine, or one hydrogen may be replaced by OH, OC(O)CH
3
, OC(O)H, O—CH
2
—Ph, NH
2
, NH—CO—CH
3
or N(COOCH
2
Ph)
2
), SO
2
—NH
2
, SO
2
NH(C
1
-
6
)-alkyl SO
2
N[(C
1
-C
6
)-alkyl]
2
, S—(C
1
-C
6
)-alkyl, S—(CH
2
)
n
-phenyl, SO—(C
1
-C
6
)-alkyl, SO—(CH
2
)
n
-phenyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—(CH)
n
-phenyl (where n is 0-6 and the phenyl radical may be optionally substituted up to two times by F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl or NH
2
), NH
2
, NH—(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, NH(C
1
-C
7
)-acyl, phenyl, biphenylyl, O—(CH
2
)
n
-phenyl (where n is 0-6), 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl, 2- or 3-thienyl (wherein the phenyl, biphenylyl, naphthyl, pyridyl, furanyl or thienyl rings may be optionally substituted up to 3 times by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), 1,2,3-triazol-5-yl (wherein triazol ring may be optionally substituted in position 1, 2 or 3 by methyl or benzyl) or tetrazol-5-yl (wherein the tetrazol ring may be optionally substituted in position 1 or 2 by methyl or benzyl);
R2 is NH
2
, NHR3 or NR4R5, wherein
R3 is (C
1
-C
6
)alkyl, CN, CHO, CO—NH
2
, CH═NH, C(S)—NH
2
, C(═NH)—NH-phenyl (wherein the phenyl ring may be optionally substituted up to two times by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), phenyl, CH
2
-phenyl (wherein the phenyl ring may be optionally substituted up to 3 times by F, Cl, Br, I, OH, NO
2
, CN, OCF
3
, O—(C
2
-C
6
)-alkyl, (C
2
-C
6
)-alkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), biphenylyl, 1- or 2-naphthyl, 4-pyridyl, 2- or 3-furanyl, 2- or 3- thienyl, 5-tetrazolyl (wherein the biphenylyl, naphthyl, pyridyl, furanyl or thienyl rings may be optionally substituted up to two times by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-6
6
)-alkyl, (C
1
-C
6
) NH
2
, NH(C
1
-C
6
)-alkyl, N((C
1
C
6
)-alkyl)
2
, SO
2
—CH
3
, COOH, COO—(C
1
-C
6
)-alkyl or CONH
2
), CH
2
-phenyl, CH
2
-pyridyl or CH
2
-4-pyridyl (wherein t

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