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US 5,474,994 AGranted
Bicyclic heterocyclic derivatives having .alpha..sub.1 -adrenergic and 5HT.sub.1A
AssigneeRecordati S.A., Chemical and Pharmaceutical Company
InventorsAmedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
Life of this patent
Estimating the term…
Abstract
This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.
Claims16
A compound having the general formula 1 ##STR22## wherein - - - represents a single or double bond;
- X represents a nitrogen, oxygen or sulfur atom, an amino or alkylamino, a sulfinyl or sulfonyl group;
- W represents a carbonyl, thiocarbonyl, hydroxymethylene, a methylene group or a bond;
- or
- X is nitrogen and W is methine, and the fused rings represent quinolyl ring;
- R.sub.2 represents a hydrogen atom or an alkyl, alkenyl, alkynyl, carbocyclic or heterocyclic group, each of which groups may optionally be substituted by one or more substituents selected from the group consisting of alkyl, cyano, hydroxy, alkoxy, halogen, phenyl, phenoxy, trifluoromethyl, nitro, acylamino, alkylsulfonylamino and benzoyl;
- or R.sub.2 itself represents a trifluoromethyl or an aroyl group;
- wherein the carbocyclic group can be substituted with amino, alkylamino or dialkylamino;
- with the proviso that the heterocyclic group cannot be linked through a nitrogen atom;
- R.sub.3 represents a hydrogen atom or an alkyl, hydroxyalkyl, phenyl, hydroxy, O-R.sub.4, alkyl-OR.sub.4 group, where R.sub.4 represents an alkyl group optionally substituted with an aryl group;
- R.sub.6 represents a hydrogen or halogen atom or a nitro, amino, acetylamino, alkylamino, dialkylamino, cyano, hydroxy, alkoxy or alkyl group;
- R.sub.7 represents a hydrogen atom or a methoxy group;
- Y represents one of the following groups, each of which is depicted with its left hand end being the end which attaches to the heterobicyclic ring and its right hand end being the end which attaches to the group Z:
- (Y1)--CO--,
- (Y2)--COO--,
- (Y3)--CONH--,
- (Y4)--CON(CH.sub.3)--,
- (Y5)--CON(OH)--,
- (Y6)--CH(OH)--,
- (Y7)--CH(OAlkyl)--,
- (Y8)--CH.dbd.CH--,
- (Y9)--CH.dbd.CH--COO--,
- (Y10)--CH.dbd.CH--CONH--,
- (Y11)--CH.dbd.NO--,
- (Y12)--CH.sub.2 --,
- (Y13)--CH.sub.2 COO--,
- (Y14)--CH.sub.2 CONH--,
- (Y15)--CH.sub.2 NH--,
- (Y16)--CH.sub.2 N(CH.sub.3)--,
- (Y17)--CH.sub.2 N(COCH.sub.3)--,
- (Y18)--CH.sub.2 N(CONH.sub.2)--,
- (Y19)--CH.sub.2 NHCO--,
- (Y20)--CH.sub.2 N(CH.sub.3)CO--,
- (Y21)--CH.sub.2 NH--CONH--,
- (Y22)--CH.sub.2 NHSO.sub.2 --,
- (Y23)--CH.sub.2 O--,
- (Y24)--CH.sub.2 S--,
- (Y25)--CH.sub.2 SO--,
- (Y26)--CH.sub.2 SO.sub.2 --,
- (Y27)--CH.sub.2 SO.sub.2 NH--,
- (Y28)--CH.sub.2 SO.sub.2 N(CH.sub.3)--,
- (Y29)--NH--,
- (Y30)--N(CH.sub.3)--,
- (Y31)--N(COCH.sub.3)--,
- (Y32)--N(CONH.sub.2)--,
- (Y33)--NHCO--,
- (Y34)--N(CH.sub.3)CO--,
- (Y35)--NH--CONH--,
- (Y36)--NHSO.sub.2 --,
- (Y37)--O--,
- (Y38)--S--,
- (Y39)--SO--,
- (Y40)--SO.sub.2 --,
- (Y41)--SO.sub.2 NH--,
- (Y42)--SO.sub.2 N(CH.sub.3)--,
- (Y43)--CONHO--,
- (Y44)--CON(COCH.sub.3)--,
- (Y45)--CSNH--,
- (Y46)--CSN(CH.sub.3)--, ##STR23## (Y48)--NHCOO-- and (Y49)--COS--
- Z represents a linear or branched chain alkylene group having from 1 to 6 carbon atoms and optionally having one hydroxy substituent;
- and
- B represents one of the following groups:
- ##STR24## wherein n is 1 or 2 and A represents a phenyl group;
- wherein said phenyl group is unsubstituted or substituted by one or more substituents selected from the group consisting of alkoxy, alkyl, halogen, hydroxy, or A represents a 2-pyrimidinyl group or a bicyclic ring of formula ##STR25## where - - - represents a single or double bond and E represents an oxygen atom or a bond;
- ##STR26## wherein L represents one or two groups selected among phenyl, 4-fluorobenzoyl or a 2-oxo-1-benzimidozolinyl group or a group of the formula (CH.sub.2).sub.n --O--A wherein n=0, 1, or 2 and A has the same meaning defined under B1, ##STR27## wherein each of R.sub.10 and R.sub.11 independently represents a hydrogen atom or an alkoxy or alkylthio group, R.sub.12 represents a hydrogen atom or an alkyl group and n is 2 or 3, ##STR28## wherein R.sub.12 has the meaning defined under B3 and R.sub.13 represents a hydrogen atom or a alkoxy group, ##STR29## wherein R.sub.12 has the meaning defined under B3, or an enantiomer, a diastereomer, an N-oxide, a prodrug, a metabolite, a prodrug of a metabolite, or a pharmaceutically acceptable salt of said compound.
61 more elements
Compound selected from the group consisting of:
- 8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-1-oxoethyl}-3-methyl-4-oxo-2-phen yl-4H-1-benzopyran/8-{2-[4-(2-methylphenyl)-1-piperazinyl]-1-oxoethyl}-3-me thyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{2-[4-(2-ethoxyphenyl)-1-piperazinyl] -1-oxoethyl}-3-methyl-4-oxo-2 -phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxy-phenyl)-1-piperazinyl]-1-oxopro pyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-pi perazinyl]-propoxycarbonyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{2-[4 -(2-methoxyphenyl)-1-piperazinyl]-ethoxycarbonyl}-3-methyl-4-oxo-2-phenyl-4 H-1-benzopyran/8-{3-[4-(2-chlorophenyl)-1-piper-azinyl]-propoxycarbonyl}-3- methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-[3-(4-phenyl-1-piperazinyl)-propoxy carbonyl]-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl) -1-piperazinyl]-2-methyl-2-propoxycarbonyl}-3-methyl-4-oxo-2-phenyl-4H-1-be nzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3-methyl -4-oxo-2-phenyl-4H-1-benzopyran/8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-et hyl-carbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[2-(2-methoxyph enoxy) -ethylamino]-propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-[3 -(4-phenyl-1-piperazinyl)-propylcarbamoyl]-3-methyl-4-oxo-2-phenyl-4H-1-ben zopyran/8-{N-methyl-2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethylcarbamoyl}-3 -methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{1-hydroxy-2-[4-(2-methoxyphenyl)- 1-piperazinyl]-ethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{1-hydroxy- 2-[4-(2-methylphenyl)-1-piperazinyl]-ethyl}-3-methyl-4-oxo-2-phenyl-4H-1-be nzopyran/8-{1-hydroxy-2-[4-(2-ethoxyphenyl)-1-piperazinyl]-ethyl}-3-methyl- 4-oxo-2-phenyl-4H-1-benzopyran/8-{1-hydroxy-3-[4-(2-methoxyphenyl)-1-pipera zinyl]-propyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{1-hydroxy-4-[4-(2 -methoxyphenyl)-1-piperazinyl]-butyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyr an/8-{1-ethoxy-2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl}-3-methyl-4-oxo-2 -phenyl-4H-1-benzopyran/8-{N-methyl-2-[4-(2-methoxyphenyl)-1-piperazinyl]-e thylaminomethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{N-acetyl-2-[4-( 2-methoxyphenyl)-1-piperazinyl]-ethylaminomethyl}-3-methyl-4-oxo-2-phenyl-4 H-1-benzopyran/8-[4-(2-methoxyphenyl)-1-piperazinylacetamidomethyl]-3-methy l-4-oxo-2-phenyl-4H-1-benzopyran/8-{N-methyl-2-[4-(2-methoxyphenyl)-1-piper azinyl]-acetamidomethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{2-[4-(2 -methoxyphenyl)-1-piperazinyl]ethoxymethyl}-3-methyl-4-oxo-2-phenyl-4H-1-be nzopyran/8-{2-[2-(2-ethoxyphenoxy)-ethylamino]-ethoxymethyl}-3-methyl-4-oxo -2-phenyl-4H-1-benzopyran/8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethylthi omethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{2-[4-(2-methoxyphenyl)- 1-piperazinyl]-ethylsulfinylmethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran /8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethylsulfonylmethyl}-3-methyl-4-o xo-2-phenyl-4H-1-benzopyran/8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethyla mino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-p iperazinyl]-propylamino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{4-[4-(2 -methoxyphenyl)-1-piperazinyl]-butylamino}-3-methyl-4-oxo-2-phenyl-4H-1-ben zopyran/8-{N-methyl-3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylamino}-3-me thyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{N-acetyl-3-[4-(2-methoxyphenyl)-1-pi perazinyl]-propylamino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2- methoxyphenyl)-1-piperazinyl]-propionamido}-3-methyl-4-oxo-2-phenyl-4H-1-be nzopyran/8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethylureido}-3-methyl-4-o xo-2-phenyl-4H-1-benzopyran/8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethoxy }-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piper azinyl]-propoxy}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8 -{4-[4-(2-methoxyphenyl)-1-piperazinyl]-butoxy}-3-methyl-4-oxo-2-phenyl-4H -1-benzopyran/8-{5-[4-(2-methoxyphenyl)-1-piperazinyl]pentoxy}-3-methyl-4-o xo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-oxo-1-piperazinyl]- propoxy}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{2-[2-(2,6-dimethoxyphen oxy)-ethylamino]-ethoxy}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{2-hydro xy-3-[4-(2-methoxyphenyl)-1-piperazinyl]-propoxy}-3-methyl-4-oxo-2-phenyl-4 H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylthio}-3-methy l-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-p ropylsulfonyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{2-[4-(2-methoxyph enyl)-1-piperazinyl]-ethylsulfamyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran /8-{N-methyl-2-[4-(2-methoxyphenyl)-1-piperazinyl]ethylsulfamyl}-3-methyl-4 -oxo-2-phenyl-4H-1-benzopyran/8-{N-aminocarbonyl-3-[4-(2-methoxyphenyl)-1-p iperazinyl]-propylamino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{4-[4-(2 -methoxyphenyl)-1-piperazinyl]-1-oxobutyl}-3-methyl-4-oxo-2-phenyl-4H-1-ben zopyran/8-{3-[2-(1,4-benzodioxanyl)methylamino]propylcarbamoyl}-3-methyl-4- oxo-2-phenyl-4H-1-benzopyran/8-{4-[4-(2-methoxyphenyl)-1-piperazinyl]butyl} -3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-[3-(4-phenyl-1-piperidinyl)propy lcarbamoyl]-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-[3-(4,4-Diphenyl-1-pi peridinyl)propylcarbamoyl]-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4- (4-fluorobenzoyl)-1-piperidinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H -1-benzopyran/8-{3-[4-(2-oxo-1-benzimidazolinyl)-1-piperidinyl]propyl-carba moyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran, 8-{-[4(2-Pyrimidinyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phen yl-4H-1-benzopyran/8-{3-[4-(2-hydroxyphenyl)-1-piperazinyl]propylcarbamoyl} -3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{4-[4-(2-methoxyphenyl)-1-pipera zinyl]butylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-me thoxyphenyl)-1-piperazinyl]propylsulfamyl}-3-methyl-4-oxo-2-phenyl-4H-1-ben zopyran/8-{3-[N -methyl-2-(2-methoxyphenoxy)ethylamino]propylcarbamoyl}-3-methyl-4-oxo-2-p henyl-4H-1-benzopyran/8-{N-methyl-3-[4-(2-methoxyphenyl)-1-piperazinyl]prop ionamido}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2methoxyphenyl)- 1-piperazinyl]propylcarbamoyl}-3-phenyl-4-oxo-4H-1-benzopyran/8-{3-[2-(3,4- dihydro-1,(2H)-naphthalenonyl)methylamino]propylcarbamoyl}-3-methyl-4-oxo-2 -phenyl-4H-1-benzopyran/8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]-ethoxycarb onylmethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{4-[4-(2-methoxypheny l)-1-piperazinyl]butylsulfamyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{ N,2-tetrahydropyranyloxy-3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylcarbam oyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{4-[4-(2-methoxyphenyl)-1-pi perazinyl]butyramido}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/E-8-{2-[4-(2- methoxyphenyl)-1-piperazinyl]ethoxyiminomethyl}-3-methyl-4-oxo-2-phenyl-4H- 1-benzopyran/8-{N -hydroxy-3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3-methyl-4 -oxo-2-phenyl-4H-1-benzopyran/E-8-{2-[2-[4-(2-methoxyphenyl)-1-piperazinyl] -ethylcarbamoyl]-ethenyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-4-[4-(2 -methoxyphenyl)-1-piperazinyl]butylsulfinyl}-3-methyl-4-oxo-2-phenyl-4H-1-b enzopyran/8-{3-[3-{2-methoxyphenoxy) propylamino]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/3-met hyl-8-{3-[2-(2-methylthiophenoxy)ethylamino]propyl carbamoyl}-4-oxo-2-phenyl-4H-1-benzopyran/8-{ 3-[2-(2,6-dimethoxyphenoxy)ethylamino]propylcarbamoyl}-3-methyl-4-oxo-2-ph enyl-4H-1-benzopyran/8-{3-[4-(5-chloro-2-methoxyphenyl)-1-piperazinyl]propy lcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/(E)-8-{4-[4-(2-methoxyp henyl)-1-piperazinyl]-1-butenyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/(E )-8-{2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethoxycarbonyl]ethenyl}-3-meth yl-4-oxo-2-phenyl-4H-1-benzopyran/8-{{2-[4-(2-methoxyphenyl)-1-piperazinyl] ethylcarbamoyl}methyl}-4-oxo-2-phenyl-4H-1-benzopyran/8-{N-acetyl-N-3-[4-(2 -methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1 -benzopyran/8-{2-[4-(2-methoxyphenyl)-1-piperazinyl]ethylsulfonylamino}-3-m ethyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperaziny l]propylthiocarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{4-[4-(2-m ethoxyphenyl)-1-piperazinyl]butylsulfonyl}-3-methyl-4-oxo-2-phenyl-4H-1-ben zopyran/3-hydroxymethyl-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarba moyl}-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperaziny l]propylcarbamoyl}-4-oxo-2-phenyl-4H-1-benzopyran/2,3-dihydro-8-{3-[4-(2-me thoxyphenyl)-1-piperazinyl]propylcarbamoyl}-4-oxo-4H-1-benzopyran/8-{3-[4-( 2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-4-oxo-4H-1-benzopyran/6-bro mo-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo- 2-phenyl-4H-1-benzopyran/6-methoxy-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl] propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/6-hydroxy-8-{3-[4- (2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H -1-benzopyran/3,6-dimethyl-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylca rbamoyl}-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperaz inyl]propylcarbamoyl}-3-methyl-6-nitro-4-oxo-2-phenyl-4H-1-benzopyran/6-ami no-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo- 2-phenyl-4H-1-benzopyran/6-acetylamino-8-{3-[4-(2-methoxyphenyl)-1-piperazi nyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran, 6-ethylamino-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-me thyl-4-oxo-2-phenyl-4H-1-benzopyran/6-dimethylamino-8-{3-[4-(2-methoxypheny l)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/7 -methoxy-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl- 4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]prop ylcarbamoyl}-3-methyl-4-oxo-2-(4-trifluoromethylphenyl)-4H-1-benzopyran/2-( 4-benzoylphenyl)-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3 -methyl-4-oxo-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propy lcarbamoyl}-3-methyl-4-oxo-2-(4-phenoxyphenyl)-4H-1-benzopyran/2,3-dimethyl -8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-4-oxo-4H-1-benzop yran/2-tert-butyl-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}- 3-methyl-4-oxo-4H-1-benzopyran/2-cyclohexyl-8-{3-[4-(2-methoxyphenyl)-1-pip erazinyl]propylcarbamoyl}-3-methyl-4-oxo-4H-1-benzopyran/2-(2-furyl)-8-{3-[ 4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-4H-1-benz opyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4- oxo-2-thienyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1piperazinyl]propyl carbamoyl}-4-oxo-2-phenyl-4H-1-benzothiopyran/(E)-8-{3-[4-(2-methoxyphenyl) -1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-(2-phenylethenyl)-4H-1-ben zopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-2 -4-methylphenyl)-4-oxo-4H-1-benzopyran/2-(4-methoxyphenyl)-8-}3-[4-(2-metho xyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-4H-1-benzopyran/2-( 4-fluorophenyl)-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl carbamoyl}-3-methyl-4-oxo-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-pipe razinyl]-propylcarbamoyl}-3-methyl-6-methanesulfonylamino-4-oxo-2-phenyl-4H -1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-me thyl-2-(4-nitrophenyl)-4-oxo-4H-1-benzopyran/6-diethoxyphosphonyloxy-8-{3-[ 4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl- 4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3- methyl-4-oxo-2-trifluoromethyl-4H-1-benzopyran/8-{N,3-[4-(2-methoxyphenyl)- 1-piperazinyl]propyl-N-methylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzop yran/2-benzoyl-3-ethyl-7-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbam oyl}benzo[b]furan/2-(4-biphenylyl)-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl] -propylcarbamoyl}-3-methyl-4-oxo-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)- 1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-(3-pyridyl)-4H-1-benzopyran /8-{3-[4-(2-acetoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-1-4-oxo- 2-phenyl-4H-1-benzopyran/3-methyl-8-{3-[4-(2-methylaminocarbonyloxyphenyl)- 1-piperazinyl]propylcarbamoyl}-4-oxo-2-phenyl-4H-1-benzopyran/6-acetoxy-8-{ 3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phen yl-4H-1-benzopyran/(R,S)-2,3-dihydro-4-hydroxy-8-{3-[4-(2-methoxyphenyl)-1- piperazinyl]propylcarbamoyl}-4H-1-benzopyran/2-(4-aminophenyl)-8-{3-[4-(2-m ethoxyphenyl)-1-piperazinyl]propylcarbamoyl}3-methyl-4-oxo-4H-1-benzopyran/ 2-(4-acetylaminophenyl)-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylcarb amoyl}-3-methyl-4H-1-benzopyran/2-(4-hydroxyphenyl)-8-{3-[4-(2-methoxypheny l)-1-piperazinyl]-propylcarbamoyl}-3-methyl-4H-1-benzopyran/8-{3-[4-(2-meth oxyphenyl)-1-piperazinyl]-propylcarbamoyl}-2-phenyl-4, N.sub.1,N4-trioxo-4H-1-benzothiopyran/7-{3-[4-(2-methoxyphenyl)-1-piperazi nyl]propylcarbamoyl}-2-phenylbenzo[b]furan/8-{3-[4-(2-methoxyphenyl)-1-pipe razinyl]propyl-N-methylsulfamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8 -{3-[4-(2-methoxyphenyl)-1-piperazinyl]butyl-N-methylsulfamoyl}-3-methyl-4- oxo-2-phenyl-4H-1-benzopyran/2-(4-dimethylaminophenyl)-8-{3-[4-(2-methoxyph enyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-4H-1-benzopyran/3-benzy loxy-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-4-oxo-2-pheny l-4H-1-benzopyran/8-{3-{4-(4-hydroxy-2-methoxyphenyl)-1-piperazinyl]propylc arbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[2-(8-methoxy-1,4-be nzodioxanyl) methylamino]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3- [4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-2-phenyl-4-thioxo-4H-1- benzopyran/8-{[2,2-dimethyl-3-(4-(2-methoxyphenyl)-1-piperazinyl)propyl]car bamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1 -piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-(2-phenylethyl)-4H-1-benzopy ran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-2-phenyl-1,1,4 -trioxo-4H-1-benzothiopyran/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylc arbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-N.sub.1 -oxide/8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4 -oxo-2-phenyl-4H-1-benzopyranN.sub.1,N.sub.4 -dioxide/8-{3-[4-(5-fluoro-2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl} -3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(2-methoxyphenyl)-1-pipera zinyl]propylcarbamoyl}-2-phenyl-4 (1H)-quinolone/2-(4-cyanophenyl)-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]p ropylcarbamoyl}-3-methyl-4-oxo-4H-1-benzopyran/6-cyano-8-{3-[4-(2-methoxyph enyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyra n/8-{3-[4-(4-fluoro -2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4 H-1-benzopyran/8-{3-[4-(3-methoxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3- methyl-4-oxo-2-phenyl-4H-1-benzopyran/8-{3-[4-(4-methoxyphenyl)-1-piperazin yl]-propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran/3-methoxy-8-{3 -[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-4-oxo-2-phenyl-4H-1-be nzopyran.
Dependencies are inferred from the claim text.