Back to results
US 8,575,342 B2Granted
HIV inhibiting 5-heterocyclyl pyrimidines
AssigneeTibotech Pharmaceuticals Ltd.
InventorsJerôme Emile Georges Guillemont, Jan Heeres, Paulus Joannes Lewi
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I), N-oxides, pharmaceutical acceptable salts, quaternary amines or stereoisomeric forms thereof, and their use as HIV replication inhibitors, In the formula, -a1=a2-a3=a4- and -b1=b2-b3=b4- may be —C═C—C═C—; X1 may be O, NR1, etc.; R1, R2, R2a, R3, R4 and R5 are assorted substituents as defined in the specification.
Claims24
A compound of formula
- an N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine or a stereochemically isomeric form thereof, wherein
- -a1=a2-a3=a4- represents a bivalent radical of formula
- —CH═CH—CH═CH— (a-1);
- -b1=b2-b3=b4- represents a bivalent radical of formula
- —CH═CH—CH═CH— (b-1);
- n is 0, 1, 2, 3 or 4;
- m is 0, 1, 2, 3 or 4;
- each R1 independently is hydrogen;
- aryl;
- formyl;
- C1-6alkylcarbonyl;
- C1-6alkyl;
- C1-6alkyloxycarbonyl;
- C1-6alkyl substituted with formyl, C1-6alkylcarbonyl, C1-6alkyloxycarbonyl, or with C1-6alkylcarbonyloxy;
- each R2 independently is halo, C1-6alkyl optionally substituted with cyano, C2-6alkenyl optionally substituted with cyano, C2-6alkynyl optionally substituted with cyano, C1-6alkyloxycarbonyl, carboxyl, cyano, amino, mono(C1-6alkylamino, or di(C1-6alkyl)amino;
- R2a is halo, cyano, aminocarbonyl, C1-6alkyl optionally substituted with cyano or aminocarbonyl, or C2-6alkenyl optionally substituted with cyano or aminocarbonyl;
- X1 is —NR1—, —O—, —C(═O)—, —CH2—, —CHOH—, —S—, —S(═O)p—;
- R3 is C1-6alkyl substituted with cyano or aminocarbonyl, or C2-6alkenyl substituted with cyano or aminocarbonyl;
- X3 is —NR1—, —O—, —C(═O)—, —S—, —S(═O)p—;
- R4 is halo, hydroxy, C1-4alkyl, C1-4alkyloxy, or cyano;
- R5 is a 5- or 6-membered completely unsaturated ring system wherein one, two, three or four ring members are hetero atoms each independently selected from the group consisting of nitrogen, oxygen and sulfur, and wherein the remaining ring members are carbon atoms;
- and, where possible, any nitrogen ring member may optionally be substituted with C1-6alkyl;
- which ring system may optionally be annelated with a benzene ring;
- and wherein any ring carbon atom, including any carbon of an optionally annelated benzene ring, may, each independently, optionally be substituted with a substituent selected from halo, hydroxy, mercapto, cyano, C1-6alkyl, hydroxyC1-4alkyl, carboxyC1-4alkyl, C1-4alkyloxyC1-4alkyl, cyanoC1-4alkyl, di(C1-4alkyl)aminoC1-4alkyl, Het-C1-4alkyl, arylC1-4alkyl, polyhaloC1-4alkyl, C3-7cycloalkyl, C2-6alkenyl, arylC2-4alkenyl, C1-4alkyloxy, —OCONH2, polyhaloC1-4alkyloxy, aryloxy, amino, mono- and di-C1-4alkylamino, C1-4alkylcarbonylamino, formyl, C1-4alkylcarbonyl, C1-4alkyloxycarbonyl, aminocarbonyl, mono- and diC1-4alkylaminocarbonyl, aryl, Het;
- wherein Het is pyridyl, thienyl, furanyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, quinolinyl, benzothienyl, benzofuranyl;
- which each may optionally be substituted with one or two C1-4alkyl radicals;
- Q is hydrogen, amino, mono- or di-C1-4alkylamino;
- each p is 1 or 2;
- each aryl is phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, mercapto, C1-6alkyl, hydroxyC1-6alkyl, aminoC1-6alkyl, mono or di(C1-6alkyl)aminoC1-6alkyl, C1-6alkylcarbonyl, C3-7cycloalkyl, C1-6alkyloxy, C1-6alkyloxycarbonyl, C1-6alkylthio, cyano, nitro, polyhaloC1-6alkyl, polyhaloC1-6alkyloxy, aminocarbonyl, Het or —X3-Het.
26 more elements
Dependencies are inferred from the claim text.