Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-11-22
2002-12-17
Rotman, Alan L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S222500, C514S223800, C514S231200, C514S237800, C514S255030, C514S259500, C514S307000, C514S311000, C514S319000, C514S357000, C514S382000, C514S383000, C514S385000, C514S403000, C514S415000, C514S428000, C514S443000, C514S459000, C514S468000, C514S471000, C514S475000, C514S534000, C514S539000, C514S541000, C514S561000, C514S562000, C514S563000, C514S577000, C514S617000, C544S008000, C544S067000, C544S159000, C544S162000, C544S283000, C544S358000, C544S386000, C544S398000, C544S402000, C546S139000, C546S
Reexamination Certificate
active
06495546
ABSTRACT:
TECHNICAL FIELD
This invention relates to new propanolamine derivatives which is the &bgr;
3
adrenergic receptor agonist and salts thereof which are useful as a medicament.
DISCLOSURE OF INVENTION
This invention relates to new propanolamine derivatives which is the &bgr;
3
adrenergic receptor agonist and salts thereof.
More particularly, it relates to new propanolamine derivatives and salts thereof which have gut selective sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic, anti-urinary incontinence and anti-pollakiuria activities, 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 animals, and more particularly to a method for the treatment and/or prevention of spasm or hyperanakinesia in case of irritable bowel syndrome, gastritis, gastric ulcer, duodenal ulcer, enteritis, cholecystopathy, cholangitis, urinary calculus and the like; for the treatment and/or prevention of ulcer such as gastric ulcer, duodenal ulcer, peptic ulcer, ulcer caused by non steroidal anti-inflammatory drugs, or the like; for the treatment and/or prevention of dysuria such as pollakiuria, urinary incontinence or the like in case of nervous pollakiuria, neurogenic bladder dysfunction, nocturia, unstable bladder, cystospasm, chronic cystitis, chronic prostatitis, overflow incontinence, passive incontinence, reflux incontinence, urge incontinence, urinary stress incontinence or the like; and for the treatment and/or prevention of pancreatitis, obesity, diabetes, glycosuria, hyperlipidemia, hypertension, atherosclerosis, glaucoma, melancholia, depression and the like.
One object of this invention is to provide new and useful propanolamine derivatives and salts thereof which have gut selective sympathomimetic, anti-ulcerous, lipolytic, anti-urinary incontinence and anti-pollakiuria activities.
Another object of this invention is to provide processes for the preparation of said propanolamine derivatives and salts thereof.
A further object of this invention is to provide a pharmaceutical composition comprising, as an active ingredient, said propanolamine 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 propanolamine derivatives and salts thereof.
The object propanolamine derivatives of this invention are new and can be represented by the following general formula [I]:
wherein
R
1
is aryl which may have one or more suitable substituent(s), heterocyclic group or cyclo(lower)alkyl,
R
2
is hydrogen or amino protective group,
R
3
and R
4
are independently hydrogen, halogen, hydroxy, amino, nitro, carboxy, protected carboxy, aryl, lower alkyl, hydroxy(lower)alkyl, amino(lower)alkyl, acyloxy(lower)alkyl, acylamino(lower)alkyl, lower alkylamino(lower)alkyl which may have one or more suitable substituent(s), mono or di-(lower)alkylamino, acylamino, acyl group, lower alkoxy, halo(lower)alkoxy, lower alkenyloxy, lower alkoxy(lower)alkoxy, aryloxy, cyclo(lower)alkyloxy, heterocyclicoxy, ar(lower)alkyloxy, acyloxy or acyl(lower)alkoxy,
R
5
is hydrogen, lower alkyl, or aryl,
A is lower alkylene which may have one or more suitable substituent(s) or lower alkenylene,
X is O, S, SO, SO
2
or NH, and
m is an integer of 0 or 1.
The object compound [I] or a salt thereof can be prepared by the following processes.
wherein
R
1
, R
2
, R
3
, R
4
, R
5
, A, X and m are each as defined above, and
R
a
2
is amino protective group.
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 carbon atom(s), unless otherwise provided.
The preferable number of the “one or more” in the term of “one or more suitable substituent(s)” may be 1 to 4.
Suitable example of “halogen” may be fluoro, chloro, bromo, iodo, and the like.
Suitable example of “lower alkyl” 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 example of “higher alkyl” may include straight or branched one having 7 to 20 carbon atoms, such as heptyl, octyl, 3,5-dimethyloctyl, 3,7-dimethyloctyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, and the like.
Suitable “lower alkoxy” and “lower alkoxy” moiety 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.
Suitable example of “aryl” and “ar” moiety may include phenyl which may have lower alkyl (e.g., phenyl, mesityl, tolyl, etc.), naphthyl, anthryl, and the like, in which the preferred one may be phenyl and naphthyl.
Suitable example of “aroyl” moiety may include benzoyl, toluoyl, naphthoyl, anthrylcarbonyl, and the like, in which the preferred one may be benzoyl and naphthoyl.
Suitable example of “protected carboxy” may be a conventional protecting group such as an esterified carboxy group, or the like, and concrete examples of the ester moiety in said esterified carboxy group may be the ones such as lower alkyl ester [e.g. methyl ester, ethyl ester, propyl ester, isopropyl ester, butyl ester, isobutyl ester, tert-butyl ester, pentyl ester, hexyl ester, 1-cyclopropylethyl ester, etc.] which may have suitable substituent(s), for example, lower alkanoyloxy(lower)alkyl ester [e.g. acetoxymethyl ester, propionyloxymethyl ester, butyryloxymethyl ester, valeryloxymethyl ester, pivaloyloxymethyl ester, 1-acetoxyethyl ester, 1-propionyloxyethyl ester, pivaloyloxyethyl ester, 2-propionyloxyethyl ester, hexanoyloxymethyl ester, etc.], lower alkanesulfonyl(lower)alkyl ester [e.g. 2-mesylethyl ester, etc.] or mono(or di or tri)halo(lower)alkyl ester [e.g. 2-iodoethyl ester, 2,2,2-trichloroethyl ester, etc.];
higher alkyl ester [e.g. heptyl ester, octyl ester, 3,5-dimethyloctyl ester, 3,7-dimethyloctyl ester, nonyl ester, decyl ester, undecyl ester, dodecyl ester, tridecyl ester, tetradecyl ester, pentadecyl ester, hexadecyl ester, heptadecyl ester, octadecyl ester, nonadecyl ester, adamantyl ester, etc.];
lower alkenyl ester [e.g. (C
2
-C
6
)alkenyl ester (e.g. vinyl ester, allyl ester, etc.)];
lower alkynyl ester [e.g. (C
2
-C
6
)alkynyl ester (e.g. ethynyl ester, propynyl ester, etc.)];
ar(lower)alkyl ester which may have one or more suitable substituent(s) [e.g. phenyl(lower)alkyl ester which may have 1 to 4 lower alkoxy, halogen, nitro, hydroxy, lower alkyl, phenyl, or halo(lower)alkyl (e.g. benzyl ester, 4-methoxybenzyl ester, 4-chlorobenzyl ester, 4-nitrobenzyl ester, phenethyl ester, trityl ester, benzhydryl ester, bis(methoxyphenyl)methyl ester, 3,4-dimethoxybenzyl ester, 4-hydroxy-3,5-di-tert-butylbenzyl ester, 4-trifluoromethylbenzyl ester, etc.)];
aryl ester which may have one or more suitable substituent(s) [e.g. phenyl ester which may have 1 to 4 lower alkyl, or halogen (e.g. phenyl ester, 4-chlorophenyl ester, tolyl ester, 4-tert-butylphenyl ester, xylyl ester, mesityl ester, cumenyl ester, etc.)];
cycloalkyloxycarbonyloxy(lower)alkyl ester which may have lower alkyl (e.g., cyclopentyloxycarbonyloxymethyl ester, cyclohexyloxycarbonyloxymethyl ester, cycloheptyloxycarbonyloxymethyl ester, 1-methylcyclohexyloxycarbonyloxymethyl ester, 1-(or 2-)[cyclopentyloxycarbonyloxy]ethyl ester, 1-(or 2-)[cyclohexyloxycarbonyloxy]ethyl ester, 1-(or 2-)-[cycloheptyloxycarbonyloxy]ethyl ester, etc.), etc.];
(5-(lower)alkyl-2
Fujii Naoaki
Hanioka Naomi
Hosoi Kumi
Ishikawa Hirofumi
Sakurai Minoru
Covington Raymond
Fujisawa Pharmaceutical Co. Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Rotman Alan L.
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