Polycyclic Dihydrothiazoles, their preparation and use as...

Details Polycyclic Dihydrothiazoles, their preparation and use as... Polycyclic Dihydrothiazoles, their preparation and use as...

2000-06-27

2001-09-18

Stockton, Laura L. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S366000

Reexamination Certificate

active

06291486

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to polycyclic dihydrothiazoles, and to their physiologically tolerable salts and physiologically functional derivatives.
BACKGROUND OF THE INVENTION
Some thiazolidine derivatives having anorectic action have been described in the art (Austrian Patent No. 365181).
SUMMARY OF THE INVENTION
The invention has the objective of making available further compounds which display a therapeutically utilizable anorectic action. It is one object of the invention to provide compounds that have anorectic action. Another object is to provide a pharmaceutical composition that comprises at least one polycyclic dihydrothiazole. Yet another object of the invention is a process for the production of a pharmaceutical comprising mixing a polycyclic dihydrothiazole with a pharmaceutically suitable vehicle. Other objects of the invention will be apparent from the specification.
Embodiments of the invention relate to compounds, medicants containing such compounds, and processes for preparing medicants, the compounds represented by the formula I
in which
Y is a direct bond, —CH
2
—, or —CH
2
—CH
2
—;
X is CH
2
, CH(CH
3
), CH(C
2
H
5
), CH(C
3
H
7
), or CH(C
6
H
5
);
R1, R1′ independently of one another are H, F, Cl, Br, I, CF
3
, NO
2
, CN, 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, and/or O—(C
1
-C
6
)-alkyl, it being possible in the alkyl radicals for one or more, or all hydrogens to be replaced by F, or a hydrogen to be replaced by OH, OC(O)CH
3
, OC(O)H, OCH
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
)
n
-phenyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—(CH
2
)
n1
-phenyl, wherein n can be 0-6 and the phenyl radical can be 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, NH
2
; NH
2
, NH—(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, NH(C
1
-C
7
)-acyl, phenyl, biphenyl, O—(CH
2
)
n1
-phenyl, wherein n1 is 0-6, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, wherein the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings each can be substituted one 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, CONH
2
; 1,2,3-triazol-5-yl, wherein the triazole ring can be substituted in the 1-, 2- or 3-position by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring can be substituted in the 1- or 2-position by methyl or benzyl;
R2 is H, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, (CH
2
)
n2
-phenyl, (CH
2
)
n
-thienyl, (CH
2
)
n
-pyridyl, (CH
2
)
n
-furyl, C(O)—(C
1
-C
6
)-alkyl, C(O) (C
3
-C
6
)-cycloalkyl, C(O)—(CH
2
)
n1
-phenyl, C(O)—(CH
2
)
n
-thienyl, C(O)—(CH
2
)
n1
-pyridyl, C(O)—(CH
2
)
n1
-furyl, wherein n can be 0-5 and in which phenyl, thienyl, pyridyl, furyl each can be substituted up to two times by Cl, F, CN, CF
3
, (C
1
-C
3
)-alkyl, OH, O—(C
1
-C
6
)-alkyl;
R3 is H, (C
1
-C
6
)-alkyl, F, CN, N
3
, O—(C
1
-C
6
)-alkyl, (CH
2
)
n1
-phenyl, (CH
2
)
n
-thienyl, (CH
2
)
n
-pyridyl, (CH
2
)
n
-furyl, wherein n can be 0-5 and in which phenyl, thienyl, pyridyl, furyl each substituted up to two times by Cl, F, CN, CF
3
, (C
1
-C
3
)-alkyl, OH, O—(C
1
-C
6
)-alkyl; (C
2
-C
6
)-alkynyl, (C
2
-C
6
)-alkenyl, C(O)OCH
3
, C(O)OCH
2
CH
3
, C(O)OH, C(O)NH
2
, C(O)NHCH
3
, C(O)N(CH
3
)
2
, OC(O)CH
3
;
R4 is (C
1
-C
8
)-alkyl, (C
3
-C
7
)-cycloalkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
4
-C
7
)-cycloalkenyl, it being possible in the alkyl radicals for one or more, or all hydrogens to be replaced by F or a hydrogen to be replaced by OH, OC(O)CH
3
, OC(O)H, O—CH
2
-Ph or O—(C
1
-C
4
)-alkyl; (CH
2
)
n1
—NR6R7, wherein n can be 1-6 and R6 and R7 independently of one another can be H, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, CO—(C
1
-C
6
)-alkyl, CHO or CO-phenyl, or —NR6R7 is a ring such as pyrrolidine, piperidine, morpholine, piperazine, N-4-methylpiperazin-1-yl, N-4-benzylpiperazin-1-yl, phthalimidoyl; (CH
2
)
n
-aryl, wherein n can be 0-6 and aryl can be phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 2-, 4- or 5-thiazolyl, 2-, 4- or 5-oxazolyl, 1-pyrazolyl, 3- or 5-isoxazolyl, 2- or 3-pyrrolyl, 2- or 3-pyridazinyl, 2-, 4- or 5-pyrimidinyl, 2-pyrazinyl, 2-(1,3,5-triazinyl), 2- or 5-benzimidazolyl, 2-benzothiazolyl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, tetrazol-5-yl, indol-3-yl, indol-5-yl or N-methyl-imidazol-2-, -4- or -5-yl and the aryl radical or heteroaryl radical can be substituted up to two times by F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, COOH, COO(C
1
-C
6
)alkyl, COO(C
3
-C
6
)-cycloalkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]2, CONH(C
3
-C
6
)cycloalkyl, NH
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl, pyrrolidin-1-yl, morpholin-1-yl, piperidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, (CH
2
)n-phenyl, O—(CH
2
)
n1
-phenyl, S—(CH
2
)
n
-phenyl, SO
2
—(CH
2
)
n
-phenyl, wherein n1=0-3;
and their physiologically tolerable salts and physiologically functional derivatives.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The inventors discovered that the compounds of the formula I are distinguished by their favorable effects on lipid metabolism; in particular, they are suitable as anorectics/slimming preparations. The compounds can be employed on their own or in combination with further slimming preparations (such as are described, for example, in Chapter D1 of the Roten Liste). The compounds are suitable for the prophylaxis and in particular for the treatment of obesity. The compounds are furthermore suitable for the prophylaxis and in particular for the treatment of type II diabetes.
a. Preferred Compounds
Preferred compounds of the formula I are those in which one or more radicals has or have the following meaning:
Y is a direct bond;
X is CH
2
;
R1, R1′ independently of one another are H, F, Cl, Br, I, CF
3
, NO
2
, CN, 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, it being possible in the alkyl radicals for one or more, or all hydrogens to be replaced by F, or a hydrogen to 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
)
n
-phenyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—(CH
2
)
n
-phenyl, wherein n can be 0-6 and the phenyl radical can be 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, NH
2
; NH
2
, NH—(C
1
-C
6
)-alkyl, N((C
1
-C
6
)-alkyl)
2
, NH(C
1
-C
7
)-acyl, phenyl, biphenyl, O—(CH
2
)
n
-phenyl, wherein n can be 0-6; 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, wherein the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings each can be substituted one 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, CONH
2
; 1,2,3-triazol-5-yl, wherein the triazole ring can be substituted in the 1-, 2- or 3-position by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring can be substituted in the 1- or 2-position by methyl or benzyl;
R2 is H, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, (CH
2
)
n1
-phenyl, (CH
2
)
n1
-thienyl, (CH
2
)
n1
-pyridyl, (CH
2
)
n1
-furyl, C(O)—(C
1
-C
6
)-alkyl, C(O)—(C
3
-C
6
)-cycloalkyl, C(O)—(CH
2
)
n
-phenyl, C(O)—(CH
2
)
n1
-thienyl, C(O)—(CH
2
)
n1

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