Aminoalcohol derivatives

Details Aminoalcohol derivatives Aminoalcohol derivatives

2003-03-21

2004-11-30

Nguyen, Chau N. (Department: 2831)

Electricity: electrical systems and devices

Electrolytic systems or devices

Liquid electrolytic capacitor

C361S506000, C361S507000, C514S332000, C514S522000, C514S534000, C514S510000

Reexamination Certificate

active

06826033

ABSTRACT:

TECHNICAL FIELD
This invention relates to new aminoalcohol derivatives and salts thereof which are beta-3 (&bgr;
3
) adrenergic receptor agonists and useful as a medicament.
DISCLOSURE OF INVENTION
This invention relates to new aminoalcohol derivatives which are &bgr;
3
adrenergic receptor agonists and salts thereof.
More particularly, it relates to new aminoalcohol derivatives and salts thereof which have gut sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic, anti-urinary incontinence, anti-pollakiuria activities, anti-diabetes and anti-obesity, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method of using the same therapeutically in the treatment and/or prevention of gastro-intestinal disorders caused by smooth muscle contractions in human beings or animal.
One object of this invention is to provide new and useful aminoalcohol derivatives and salts thereof which have gut sympathomimetic, anti-ulcerous, lipolytic, anti-urinary incontinence, anti-pollakiuria activities, anti-diabetes and anti-obesity.
Another object of this invention is to provide processes for the preparation of said aminoalcohol derivatives and salts thereof.
A further object of this invention is to provide a pharmaceutical composition comprising, as an active ingredient, said aminoalcohol derivatives and salts thereof.
Still further object of this invention is to provide a therapeutical method for the treatment and/or prevention of aforesaid diseases in human beings or animals, using said aminoalcohol derivatives and salts thereof.
The object aminoalcohol derivatives of this invention are new and can be represented by the following formula [I]:
wherein
X
1
is bond or —O—CH
2
—,
(in which R
2
is hydrogen or lower alkyl and n is an integer of 1 or 2)
[in which
(in which R
3
is hydrogen or lower alkyl),
(in which R
4
is hydrogen or lower alkyl),
(in which Y
2
is lower alkylene)],
R
1
is hydrogen or an amino protective group,
A is phenyl, indolyl or carbazolyl, each of which may be substituted with one or two substituent(s) selected from the group consisting of halogen, hydroxy, hydroxy(lower)alkyl and benzyloxy, and
B is hydrogen; halogen; lower alkyl; lower alkoxycarbonyl; cyclo(lower)alkyl; or a heterocyclic group, naphthyl, 1,2,3,4-tetrahydronaphthyl, benzyl or phenyl, each of which may be substituted with one or two substituent(s) selected from the group consisting of halogen, lower alkoxy, mono(or di or tri)halo(lower)alkoxy, carboxy(lower)alkoxy, lower alkoxycarbonyl(lower)alkoxy, phenoxy, lower alkyl, mono(or di or tri)-halo(lower)alkyl, cyano, carboxy, lower alkoxycarbonyl, lower alkanoyl, benzoyl, mono(or di)(lower)-alkylcarbamoyl, (lower alkylsulfonyl)carbamoyl, (lower alkylsulfonyl)amino, (lower alkoxycarbonyl)amino, amino, nitro, pyridyl, triazolyl, thiazolyl optionally substituted with phenyl or lower alkyl, and phenyl optionally substituted with mono(or di or tri)halo(lower)alkyl,
or a salt thereof.
The object compound [I] or a salt thereof can be prepared by the following processes.
wherein X
1
, X
2
, R
1
, A and B are each as defined above,
R
a
1
is an amino protective group,
R
a
2
is lower alkyl,
W
1
is a leaving group,
W
2
is an acid residue,
m is an integer of 1 or 2,
k is 0 or an integer of 1, and
{circle around (P)} is polymer.
In the above and subsequent description of the present specification, suitable examples of the various definition to be included within the scope of the invention are explained in detail in the following.
The term “lower” is intended to mean a group having 1 to 6, preferably 1 to 4, carbon atom(s), unless otherewise provided.
Suitable example of “lower alkyl” and “lower alkyl” moiety in the terms of “hydroxy(lower)alkyl”, “mono(or di or tri)halo(lower)alkyl”, etc. may include straight or branched one having 1 to 6 carbon atom(s), such as methyl, ethyl propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 1-methylpentyl, tert-pentyl, neo-pentyl, hexyl, isohexyl, and the like.
Suitable “lower alkoxy” and “lower alkoxy” moiety in the terms of “lower alkoxycarbonyl”, “carboxy(lower)alkoxy”, etc. may be a straight or branched one such as methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, butoxy, sec-butoxy, tert-butoxy, pentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, and the like, in which the preferred one may be C
1
-C
4
alkoxy, and the most preferred one may be methoxy or ethoxy.
Suitable “lower alkylene” may include straight or branched one such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, methylmethylene, ethylethylene, propylene, and the like, in which more preferable example may be C
1
-C
4
alkylene and the most preferable one may be trimethylene.
Suitable example of “halogen” may be fluoro, chloro, bromo and iodo.
Suitable “cyclo(lower)alkyl” may include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, in which the preferred one may be cyclohexyl.
Suitable “lower alkanoyl” may be formyl, acetyl, propanoyl, butanoyl, 2-methylpropanoyl, pentanoyl, 2,2-dimethylpropanoyl, hexanoyl and the like, in which the preferred one may be acetyl.
Suitable “mono(or di or tri)halo(lower)alkyl” may be fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, 1 or 2-fluoroethyl, 1 or 2-bromoethyl, 1 or 2-chloroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, and the like, in which the preferred one may be trifluoromethyl.
Suitable example of “heterocyclic group” may include
unsaturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing 1 to 4 nitrogen atom(s), for example, pyrrolyl, pyrrolinyl, imidazolyl, pyrazolyl, pyridyl, dihydropyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazolyl (e.g., 4H-1,2,4-triazolyl, 1H-1,2,3-triazolyl, 2H-1,2,3-triazolyl, etc.), tetrazolyl (e.g., 1H-tetrazolyl, 2H-tetrazolyl, etc.), etc.;
saturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing 1 to 4 nitrogen atom(s), for example, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, etc.;
unsaturated condensed heterocyclic group containing 1 to 4 nitrogen atom(s), for example, indolyl, isoindolyl, indolinyl, indolizinyl, benzimidazolyl, quinolyl, isoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, indazolyl, benzotriazolyl, etc.;
unsaturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing 1 or 2 oxygen atom(s) and 1 to 3 nitrogen atom(s), for example, oxazolyl, isoxazolyl, oxadiazolyl (e.g., 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, etc.), etc.;
saturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing 1 or 2 oxygen atom(s) and 1 to 3 nitrogen atom(s), for example, morpholinyl, sydnonyl, etc.;
unsaturated condensed heterocyclic group containing 1 or 2 oxygen atom(s) and 1 to 3 nitrogen atom(s), for example, benzoxazolyl, benzoxadiazolyl, etc.;
unsaturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing 1 or 2 sulfur atom(s) and 1 to 3 nitrogen atom(s), for example, thiazolyl, isothiazolyl, thiadiazolyl (e.g., 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, etc.), dihydrothiazinyl, etc.;
saturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing 1 or 2 sulfur atom(s) and 1 to 3 nitrogen atom(s), for example, thiazolidinyl, etc.;
unsaturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing 1 or 2 sulfur atom(s), for example, thienyl, dihydrodithiinyl, dihydrodithionyl, etc.;
unsaturated condensed heterocyclic group containing 1 or 2 sulfur atom(s) and 1 to 3 nitrogen atom(s), for example, benzothiazolyl, benzothiadiazolyl, imidazothiadiazolyl, etc.;
unsaturated 3 to 8-membered (more preferably 5 or 6-membered) heteromonocyclic group containing an oxygen atom, for example, furyl, etc.;
saturated 3 to 8-membered (more preferably 5

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