Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-04-10
2003-11-11
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S266200, C514S266230, C514S266240, C514S266300, C514S266310, C514S258100, C514S234500, C514S252040, C514S252170, C544S116000, C544S238000, C544S253000, C544S284000, C544S286000
Reexamination Certificate
active
06645971
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a compound, which have antagonism effect on muscarinic receptor and can be useful as anticholinergic medicaments, its prodrug and pharmaceutically acceptable salt thereof, and their use. Antagonists against muscarinic receptor can be used, for example, as mydriatic medicament, anticonvulsant, parkinsonian remedy, antasthmatic, peptic ulcer remedy, secretagogue and motofacient for gastric and duodenal ulcer, intestinum hypersensitivity remedy, pollakiuria remedy, urinary incontinence remedy, antiarrhythmic medicament, esophageal achalasia remedy, chronic obstructive tracheal disease remedy and so on.
BACKGROUND ART
The quinazolinone derivatives having subneural, anti-inflammatory and analgesic action are described in Japanese Unexanined Patent Publication No. sho47-14183, the quinazolinone derivatives having an effect of inhibiting central nervous system are described in French Patent No. 2,027,023, and the quinazolinone derivatives having an effect of preventing overload of calcium ions are described in Japanese Unexamined Patent Publication No. hei7-41465, respectively. However, they do not refer to the use of anticholinergic medicament, especially urinary incontinence and pollakiuria remedy.
DISCLOSURE OF THE INVENTION
The subject of the present invention is to provide antagonists against muscarinic receptor which is useful as anticholinergic medicament.
The present inventors have earnestly studied for solving the above problem, found that the compounds given by general formula (1) below, their prodrugs and pharmaceutically acceptable salts thereof have antagonism effect on muscarinic receptor, and now completed the present invention. Namely, the present invention relates to the following [11] to [15]:
[1] An anticholinergic medicament comprising a compound given by general formula (1):
[wherein T represents oxygen or sulfur atom, and Y represents alkyl, cycloalkyl, cycloalkylalkyl, phenyl, substituted phenyl, aralkyl, substituted aralkyl, heteroaryl or substituted heteroaryl group. Ring W represents benzene, 5-6 membered heteroaromatic, 5-10 membered cycloalkene or 5-10 membered cycloalkane ring. R
1
and R
2
represent independently hydrogen atom, lower alkyl group, halogen atom, cyano, trifluoromethyl, nitro, amino, substituted amino, hydroxy, lower alkoxy, lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl group. R
3
represents hydrogen atom, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkylalkyl, aralkyl or substituted aralkyl group.
Z represents a group given by formula:
{wherein A
1
and A
2
represent independently hydrogen atom, alkyl, substituted alkyl, cycloalkyl, saturated heterocyclic, cycloalkylalkyl, cycloalkenylalkyl, aralkyl, substituted aralkyl, heteroarylalkyl, substituted heteroarylalkyl or —CH
2
R
4
group (wherein R
4
represents alkenyl or alkynyl group), or A
1
and A
2
are combined together and form heterocyclic ring. G represents straight chain alkylene having 1-6 of the carbon number, branched alkylene having 2-8 of the carbon number, a group given by formula:
(wherein p and m represent independently 0, 1 or 2 and D represents cycloalkane ring)} or
{wherein n represents 0, 1 or 2, ring E represents 4-8 membered saturated heterocyclic ring containing nitrogen atom(s), and A
3
represents hydrogen atom, alkyl, substituted alkyl, cycloalkyl, saturated heterocyclic, cycloalkylalkyl, cycloalkenylalkyl, aralkyl, substituted aralkyl, heteroarylalkyl, substituted heteroarylalkyl or —CH
2
R
4
group (wherein R
4
represents alkenyl or alkynyl group), or forms bicyclo ring together with ring E}], its prodrug or pharmaceutically acceptable salt thereof as an active ingredient.
[2] An anticholinergic medicament described in [1], wherein ring W represents 5-6 membered heteroaromatic, 5-10 membered cycloalkene or 5-10 membered cycloalkane ring.
[3] An anticholinergic medicament described in [1], wherein ring W represents benzene ring and Z represents a group given by formula:
[4] An anticholinergic medicament described in [1], wherein Z represents a group given by formula:
[5] An anticholinergic medicament described in [4], wherein ring W represents benzene or pyridine ring.
[6] An anticholinergic medicament described in [5], wherein ring W represents benzene ring.
[7] An anticholinergic medicament described in [6], wherein Y represents phenyl or substituted phenyl group.
[8] An anticholinergic medicament described in [4], wherein ring W represents benzene or pyridine ring and Z represents a group given by formula:
(wherein A
4
represents phenyl, substituted phenyl, cycloalkyl or cycloalkenyl group).
[9] An anticholinergic medicament described in [8], wherein A
4
represents cycloalkyl or cycloalkenyl group.
[10] An anticholinergic medicament described in [8], wherein A
4
represents phenyl or substituted phenyl group.
[11] An anticholinergic medicament described in [8], wherein A
4
represents substituted phenyl group and said substituent is cyano, alkoxyalkyl, alkanoylamino, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group.
[12] An anticholinergic medicament described in any of [1]-[11], wherein the medicament is urinary incontinence or pollakiuria remedy.
[13] A compound given by general formula (1):
[wherein T represents oxygen or sulfur atom, and Y represents alkyl, cycloalkyl, cycloalkylalkyl, phenyl, substituted phenyl, aralkyl, substituted aralkyl, heteroaryl or substituted heteroaryl group. Ring W represents benzene or pyridine ring. R
1
and R
2
represent independently hydrogen atom, lower alkyl group, halogen atom, cyano, trifluoromethyl, nitro, amino, substituted amino, hydroxy, lower alkoxy, lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl group. R
3
represents hydrogen atom, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, aralkyl or substituted aralkyl group. Z represents a group given by formula:
(wherein A
4
represents phenyl group substituted by alkoxyalkyl group), its prodrug or pharmaceutically acceptable salt thereof.
[14] A compound given by general formula (1a):
[wherein T represents oxygen or sulfur atom, and Y represents alkyl, cycloalkyl, cycloalkylalkyl, phenyl, substituted phenyl, aralkyl, substituted aralkyl, heteroaryl or substituted heteroaryl group. Ring W represents benzene, 5-6 membered heteroaromatic, 5-10 membered cycloalkene or 5-10 membered cycloalkane ring. R
1
and R
2
represent independently hydrogen atom, lower alkyl group, halogen atom, cyano, trifluoromethyl, nitro, amino, substituted amino, hydroxy, lower alkoxy, lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl group. R
31
represents alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, aralkyl or substituted aralkyl group. Z represents a group given by formula:
{wherein A
1
and A
2
represent independently hydrogen atom, alkyl, substituted alkyl, cycloalkyl, saturated heterocyclic, cycloalkylalkyl, cycloalkenylalkyl, aralkyl, substituted aralkyl, heteroarylalkyl, substituted heteroarylalkyl or —CH
2
R
4
group (wherein R
4
represents alkenyl or alkynyl group), or A
1
and A
2
are combined together and form heterocyclic ring. G represents straight chain alkylene having 1-6 of the carbon number, branched alkylene having 1-8 of the carbon number, a group given by formula:
(wherein p and m represent independently 0, 1 or 2 and D represents cycloalkane ring)} or formula:
{wherein n represents 0, 1 or 2, ring E represents 4-8 membered saturated heterocyclic ring containing nitrogen atom(s), and A
3
represe
Matsui Kazuki
Morishita Koji
Muraoka Masami
Ohashi Naohito
Shah Mukund J.
Sumitomo Pharmaceuticals Company Limited
Truong Tamthom N.
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