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Claims for Patent: 7,037,917

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Claims for Patent: 7,037,917

Title:HIV replication inhibiting pyrimidines
Abstract:This invention concerns the use of compounds of formula ##STR00001## the N-oxides, the pharmaceutically acceptable addition salts, quaternary amines and the stereochemically isomeric forms thereof, wherein -a.sup.1=a.sup.2-a.sup.3=a.sup.4- forms a phenyl, pyridinyl, pyrimidinyl, pyridazinyl or pyrazinyl with the attached vinyl group; n is 0 to 4; and where possible 5; R.sup.1 is hydrogen, aryl, formyl, C.sub.1-6alkylcarbonyl, C.sub.1-6alkyl, C.sub.1-6alkyloxycarbonyl, substituted C.sub.1-6alkyl, or substituted C.sub.1-6alkyloxyC.sub.1-6alkylcarbonyl; each R.sup.2 independently is hydroxy, halo, optionally substituted C.sub.1-6alkyl, C.sub.2-6alkenyl or C.sub.2-6alkynyl, C.sub.3-7cycloalkyl, C.sub.1-6alkyloxy, C.sub.1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C.sub.1-6alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, --S(.dbd.O).sub.pR.sup.6, --NH--S(.dbd.O).sub.pR.sup.6, --C(.dbd.O)R.sup.6, --NHC(.dbd.O)H, --C(.dbd.O)NHNH.sub.2, --NHC(.dbd.O)R.sup.6, --C(.dbd.NH)R.sup.6 or a 5-membered heterocyclic ring; p is 1 or 2; L is optionally substituted C.sub.1-10alkyl, C.sub.2-10alkenyl, C.sub.2-10alkynyl or C.sub.3-7cycloalkyl; or L is --X--R.sup.3 wherein R.sup.3 is optionally substituted phenyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl; X is --NR.sup.1--, --NH--NH--, --N.dbd.N--, --O--, --C(.dbd.O)--, --CHOH--, --S--, --S(.dbd.O)-- or --S(.dbd.O).sub.2--; Q is hydrogen, C.sub.1-6alkyl, halo, polyhalo-C.sub.1-6alkyl or an optionally substituted amino group; Y represents hydroxy, halo, C.sub.3-7cycloalkyl, optionally substituted C.sub.1-6alkyl, C.sub.2-6alkenyl or C.sub.2-6alkynyl, C.sub.1-6alkyloxy, C.sub.1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C.sub.1-6alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, --S(.dbd.O).sub.pR.sup.6, --NH--S(.dbd.O).sub.pR.sup.6, --C(.dbd.O)R.sup.6, --NHC(.dbd.O)H, --C(.dbd.O)NHNH.sub.2, --NHC(.dbd.O)R.sup.6, --C(.dbd.NH)R.sup.6 or aryl; aryl is optionally substituted phenyl; Het is an optionally substituted heterocyclic radical; for the manufacture of a medicine for the treatment of subjects suffering from HIV (Human Immunodeficiency Virus) infection.
Inventor(s): De Corte; Bart (Southampton, PA), De Jonge; Marc Rene (Tilburg, NL), Heeres; Jan (Vosselaar, BE), Ho; Chih Yung (Lansdale, PA), Janssen; Paul Adriaan Jan (Vosselaar, BE), Kavash; Robert W. (Maple Glen, PA), Koymans; Lucien Maria Henricus (Turnhout, BE), Kukla; Michael Joseph (Maple Glen, PA), Ludovici; Donald William (Quakertown, PA), Van Aken; Koen Jeanne Alfons (Turnhout, BE)
Assignee: Janssen Pharmaceutica, N.V. (BE)
Application Number:10/634,682
Patent Claims: 1. A pyrimidinyl compound 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino- ]benzonitrile, a N-oxide, an addition salt, a quaternary amine or a stereochemically isomeric form thereof, said compound having the following structure: ##STR00032##

2. A pyrimidinyl compound wherein the pyrimidinyl compound is 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino- ]benzonitrile, said compound having the following structure: ##STR00033##

3. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an effective amount of a pyrimidinyl compound according to any of claims 1 or 2.

4. A combination comprising a pyrimidinyl compound according to any of claims 1 or 2 and an antiretroviral compound, wherein said antiretroviral compound comprises at least one of a nucleoside reverse transcriptase inhibitor, a non-nucleoside reverse transcriptase inhibitor, a TIBO compound, an .alpha.-APA compound, a TAT-inhibitor, a protease inhibitor, an immunomodulating agent, and mixtures thereof.

5. A combination according to claim 4, wherein said nucleoside reverse transcriptase inhibitor comprises at least one of zidovudine (3'-azido-3'-deoxythymidine, AZT), didanosine (dideoxy inosine; ddI), zalcitabine (dideoxycytidine, ddC), lamivudine (3'-thia-2'-3'-dideoxycytidine, 3TC), and mixtures thereof.

6. A combination according to claim 4, wherein said non-nucleoside reverse transciptase inhibitors comprises at least one of suramine, pentamidine, thymopentin, castanospermine, efavirenz, dextran sulfate, foscarnet-sodium (trisodium phosphono formate), nevirapine (11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido-[3,2-b:2',3'-e][1,4]dia- zepin-6-one), tacrine (tetrahydroaminoacridine), and mixtures thereof.

7. A combination according to claim 4, wherein said TIBO compound comprises (S)-8-chloro-4,5,6,7-tetrahydro-5-methyl-6-(3-methyl-2-butenyl)- imidazo[4,5,1-jk][1,4]benzodiazepine-2(1H)-thione.

8. A combination according to claim 4, wherein said .alpha.-APA compound comprises .alpha.-[(2-nitro-phenyl)amino]-2,6-dichlorobenzene-acetamide.

9. A combination according to claim 4, wherein said protease inhibitor comprises at least one of indinavir, ritanovir, saquinovir, ABT-378, and mixtures thereof.

10. A combination according to claim 4, comprising at least one of RO-5-3335, levamisole, and mixtures thereof.

11. A combination according to claim 5, further comprising a pharmaceutically acceptable carrier.

12. A combination according to claim 6, further comprising a pharmaceutically acceptable carrier.

13. A combination according to claim 7, further comprising a pharmaceutically acceptable carrier.

14. A combination according to claim 8, further comprising a pharmaceutically acceptable carrier.

15. A combination according to claim 9, further comprising a pharmaceutically acceptable carrier.

16. A combination according to claim 10, further comprising a pharmaceutically acceptable carrier.

17. A combination according to claim 4 wherein said pyrimidinyl compound and said antiretroviral compound are combined in a single preparation.

18. A combination according to claim 17, further comprising a pharmaceutically acceptable carrier.

19. A process for preparing a compound as claimed in claim 2, comprising reacting a compound of formula ##STR00034## with NH.sub.3 in the presence of a reaction inert solvent.

20. A process according to claim 19, wherein said reacting is performed in the presence of a base.

21. A method of treating subjects suffering from HIV (Human Immunodeficiency Virus) infection comprising administering to the subject an effective amount of a compound according to claims 1 or 2.

22. A method of treating subjects suffering from HIV (Human Immunodeficiency Virus) infection comprising administering to the subject a an effective amount of a combination according to claim 4.

23. A pyrimidinyl compound as claimed in claim 1, wherein the compound is an addition salt of 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino- ]benzonitrile.

24. A pyriniidinyl compound as claimed in claim 23, wherein the compound is the hydrochloride salt of 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino- ]benzonitrile.

25. A pyrimidinyl compound as claimed in claim 1, wherein the compound is a quaternary amine of 4-[[4amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]- benzonitrile.

26. A pharmaceutical composition as claimed in claim 3, wherein the pharmaceutical composition is a tablet.

27. A pharmaceutical composition as claimed in claim 3, wherein the effective amount is between 1 to 1000 mg of active ingredient per unit dosage form.

28. A pharmaceutical composition as claimed in claim 1, wherein the effective amount is between 5 and 200 mg of active ingredient per unit dosage form.

29. A tablet as claimed in claim 26, wherein the effective amount is between 1 to 1000 mg of active ingredient.

30. A tablet as claimed in claim 29, wherein the effective amount is between 5 to 200 ing of active ingredient.

31. A method of treating subjects suffering from HIV-1 (Human Immunodeficiency Virus) infection that have acquired resistance to art-known non-nucleoside reverse transcriptase inhibitors comprising administering to the subject an effective amount of a compound according to any of claims 1 or 2.

32. A method of treating subjects suffering from HIV-1 (Human Immunodeficiency Virus) infection that have acquired resistance to art-known non-nucleoside reverse transcriptase inhibitors comprising administering to the subject an effective amount of a combination comprising a pyrimidinyl compound according to any of claims 1 or 2 and an antiretroviral compound, wherein said antiretroviral compound comprises at least one of a nucleoside reverse transcriptase inhibitor, a non-nucleoside reverse transcriptase inhibitor, a TIBO compound, an .alpha.-APA compound, a TAT-inhibitor, a protease inhibitor, an immunomodulating agent, and mixtures thereof, and wherein said pyrimidinyl compound and said antiretroviral compound are administered simultaneously, separately or sequentially.
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