Azaindoles, preparation processes and medicinal products containing them
First Claim
1. A compound selected from the group consisting of compounds of the formula I, ##STR6## wherein one of the groups X1 to X4 is nitrogen and the others are CH;
- R1 and R2, which may be located at position 1, 2 or 3 of azaindole, each are selected from hydrogen, linear or branched C1 to C12 alkyl or C2 to C6 alkenyl optionally substituted at the ω
position with a group selected from carboxyl, C1 to C3 alkyl carboxylate and phenyl;
R1 and R2 can also be C3 to C8 cycloalkyl or C3 to C8 cycloalkenyl or, when they are at position 2 or 3 of azaindole, halogen, or C1 to C4 alkylthio;
R1 and R2 can also be phenyl or benzyl, unsubstituted or having one to three substituents selected from halogen and C1 to C4 alkyl, C1 to C4 alkoxy and C1 to C4 alkylthio, or thienyl or pyridyl which can optionally have a substituent selected from halogen and C1 to C4 alkyl and C1 to C4 alkoxy;
one of R1 and R2 can also be selected from hydroxymethyl, (C1 to C4 alkoxy)methyl, N,N-di(C1 to C4 alkyl)amino(C1 to C4 alkyl)oxymethyl, piperidino, carboxyl and C1 to C3 alkyl carboxylate and the other hydrogen;
R3 and R4, which may be located on the ventricles 4, 5, 6 of 7 of azaindole provided that these vertices embody carbon, each are selected from hydrogen, halogen, C1 to C6 alkyl, C1 to C4 alkoxy, C1 to C6 alkylthio or C3 to C8 cycloalkyl;
--C(R5)(R6)--CH(R7)--N(R8)--CO--NH--R9 may be attached to the verticles 1, 2, or 3 of azaindole, on the understanding that, when nitrogen at position 1 of azaindole is not substituted with one of R1, R2 or --C(R5)(R6)--CH(R7)--N(R8)--CO--NH--R9, it bears hydrogen;
R5 and R6 are each selected from hydrogen, C1 to C12 alkyl, C2 to C6 alkenyl, C3 to C8 cycloalkyl, C3 to C8 cycloalkenyl, C2 to C12 alkoxyalkyl, C2 to C12 alkyl-thioalkyl, or alternatively R5 and R6 together form and alkylene chain of the formula --(CH2)p -- optionally substituted with one or two C1 to C4 alkyl and in which p can assume the values 3 to 7, or an alkyleneoxyalkylene chain of the formula --(CH2)x --O--(CH2)--y, in which x and y can independently assume the value 1 or 2;
R7 is selected from hydrogen, C2 to C6 alkyl and C3 to C8 cycloalkyl;
one of the substituents R5 to R7 can also be phenyl or benzyl, unsubstituted or having one to three substituents selected from halogen, C1 to C4 alkyl, alkoxy and alkylthio;
R8 is selected from hydrogen, C1 to C12 alkyl, C3 to C8 cycloalkyl and benzyl which is unsubstituted or bears 1 to 3 substituents selected from halogen, C1 to C4 alkyl, alkoxy and alkylthio;
R9 is pyrimidyl or phenyl, unsubstituted or bearing one to three substituents selected from halogen and C1 to C4 alkyl, C1 to C4 alkoxy and C1 to C4 alkylthio.
1 Assignment
0 Petitions
Accused Products
Abstract
These compounds correspond to the formula ##STR1## in which one of the groups X1 to X4 represents nitrogen and the others a CH radical,
R1 and R2 represent H, halogen, alkyl, hydroxymethyl, alkyloxymethyl, dialkylaminoalkyl, dialkylaminoalkyloxymethyl, carboxyl, ethyl carboxylate, piperidino, alkenyl, cycloalkyl, cycloalkenyl, alkylthio, benzyl, phenyl, thiophene or pyridine, optionally substituted,
R3 and R4 represent H, halogen, alkyl, cycloalkyl, alkoxy or alkylthio,
R5 and R6 denote H, alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl or alkylthioalkyl, or together form alkylene or alkyleneoxyalkylene chains,
R7 denotes H, alkyl or cycloalkyl; one of the radicals R5 to R7 can also denote optionally substituted phenyl or benzyl,
R8 represents H, alkyl, cycloalkyl or optionally substituted phenyl or benzyl,
R9 denotes optionally substituted phenyl, naphthyl or heterocyclic,
as well as their tautomeric forms, processes for preparing them and application as hypolipidaemic and antiatheromatous medicinal products.
113 Citations
12 Claims
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1. A compound selected from the group consisting of compounds of the formula I, ##STR6## wherein one of the groups X1 to X4 is nitrogen and the others are CH;
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R1 and R2, which may be located at position 1, 2 or 3 of azaindole, each are selected from hydrogen, linear or branched C1 to C12 alkyl or C2 to C6 alkenyl optionally substituted at the ω
position with a group selected from carboxyl, C1 to C3 alkyl carboxylate and phenyl;
R1 and R2 can also be C3 to C8 cycloalkyl or C3 to C8 cycloalkenyl or, when they are at position 2 or 3 of azaindole, halogen, or C1 to C4 alkylthio;
R1 and R2 can also be phenyl or benzyl, unsubstituted or having one to three substituents selected from halogen and C1 to C4 alkyl, C1 to C4 alkoxy and C1 to C4 alkylthio, or thienyl or pyridyl which can optionally have a substituent selected from halogen and C1 to C4 alkyl and C1 to C4 alkoxy;
one of R1 and R2 can also be selected from hydroxymethyl, (C1 to C4 alkoxy)methyl, N,N-di(C1 to C4 alkyl)amino(C1 to C4 alkyl)oxymethyl, piperidino, carboxyl and C1 to C3 alkyl carboxylate and the other hydrogen;R3 and R4, which may be located on the ventricles 4, 5, 6 of 7 of azaindole provided that these vertices embody carbon, each are selected from hydrogen, halogen, C1 to C6 alkyl, C1 to C4 alkoxy, C1 to C6 alkylthio or C3 to C8 cycloalkyl; --C(R5)(R6)--CH(R7)--N(R8)--CO--NH--R9 may be attached to the verticles 1, 2, or 3 of azaindole, on the understanding that, when nitrogen at position 1 of azaindole is not substituted with one of R1, R2 or --C(R5)(R6)--CH(R7)--N(R8)--CO--NH--R9, it bears hydrogen; R5 and R6 are each selected from hydrogen, C1 to C12 alkyl, C2 to C6 alkenyl, C3 to C8 cycloalkyl, C3 to C8 cycloalkenyl, C2 to C12 alkoxyalkyl, C2 to C12 alkyl-thioalkyl, or alternatively R5 and R6 together form and alkylene chain of the formula --(CH2)p -- optionally substituted with one or two C1 to C4 alkyl and in which p can assume the values 3 to 7, or an alkyleneoxyalkylene chain of the formula --(CH2)x --O--(CH2)--y, in which x and y can independently assume the value 1 or 2; R7 is selected from hydrogen, C2 to C6 alkyl and C3 to C8 cycloalkyl; one of the substituents R5 to R7 can also be phenyl or benzyl, unsubstituted or having one to three substituents selected from halogen, C1 to C4 alkyl, alkoxy and alkylthio; R8 is selected from hydrogen, C1 to C12 alkyl, C3 to C8 cycloalkyl and benzyl which is unsubstituted or bears 1 to 3 substituents selected from halogen, C1 to C4 alkyl, alkoxy and alkylthio; R9 is pyrimidyl or phenyl, unsubstituted or bearing one to three substituents selected from halogen and C1 to C4 alkyl, C1 to C4 alkoxy and C1 to C4 alkylthio. - View Dependent Claims (2, 3, 5, 6, 7, 8, 9, 10, 11, 12)
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4. A compound selected from the group consisting of:
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N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[2-(7-azaindol-1-yl)-2-alkyl-4-pentenyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[2(7-azaindol-1-yl)-2-allyl-4-pentenyl]-N2 -(4-fluoro-2-methylphenyl)urea; N1 -[2-(7-azaindol-1-yl)-2-phenethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[2-(7-azaindol-1-yl)-2-methyl-propyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[(1-methyl-7-azaindol-3-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[(5-azaindolyl-1-)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[2-(7-azaindol-1-yl)hexyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-ethyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(7-azaindol-1-yl)cyclohexylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(6-chloro-3-phenyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[2(7-azaindol-1-yl)-3-phenylpropyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-ethyl-4-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[4-(7azaindol-1-yl)-4-pyranylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[4-(7-azaindol-1-yl)-1-penten-5-yl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(2,3-dimethyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-benzyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-butyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 [1-(3-propyl-azaindol-1-yl)cyclopentylmethyl]-N2 -[2,6-diisopropylphenyl)urea; N1 -[1-(3-isopropyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-phenyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[2-(7-azaindol-1-yl)butyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-dimethylaminomethyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-methylthio-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl]urea; N1 -[1-(3-hydroxymethyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(5-chloro-3-ethyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(6-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(4-methyl-3-phenyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-methyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -{1-[3-(4-fluorophenyl)-7-azaindol-1-yl]cyclopentylmethyl}-N2 -(2,6-diisopropylphenyl)urea; N1 -[2-(3-phenyl-7-azaindol-1-yl)hexyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -{1-[3-(4-methoxyphenyl)-7-azaindol-1-yl]cyclopentylmethyl}-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-methoxycarbonyl-7-azaindol-1-yl)cyclopentylmethyl]N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-hexyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,4,6-trimethoxyphenyl)urea; N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N2 -(4,6-dimethoxy-5-pyrimidinyl)urea; N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diethylphenyl)urea; N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2-isopropylphenyl)urea; N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,4-diisopropylphenyl)urea; N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N1 -benzyl-N2 -(2,4-difluorophenyl)urea; N1 -[1-(3-bromo-7-azaindol-1-yl)cyclpentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-chloro-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-methoxymethyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -{1-[3-(2-diethylaminoethoxymethyl)-7-azaindol-1-yl]cyclopentylmethyl}-N.sup.2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-ethenyl-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -{1-[3-(2-phenylethen-1-yl)-7-azaindol-1-yl]cyclopentylmethyl}-N2 -(2,6-diisopropylphenyl)urea; N1 -{1-[3-(2-methoxycarbonylethen-1-yl)-7-azaindol-1-yl]cyclopentylmethyl}-N.sup.2 -(2,6-diisopropylphenyl)urea; N1 -[1-(3-piperidino-7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylphenyl)urea; N1 -[(7-azaindol-1-yl)cyclopentylmethyl]-N2 -(2,6-diisopropylpenyl)urea hydrochloride; N1 -[1-(7-azaindol-1-yl)cyclopentylmethyl]-N1 -benzyl-N2 -(2,6-diisopropylphenyl)urea; N1 -[2-(3-ethyl-7-azaindol-1-yl)hexyl]-N2 -(2,6-diisopropylphenyl)urea hydrochloride.
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Specification