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Generated: August 22, 2017

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Title:2,4-di (phenylamino) pyrimidines useful in the treatment of neoplastic diseases, inflammatory and immune system disorders
Abstract: Novel pyrimidine derivatives of formula I ##STR00001## to process for their production, their use as pharmaceuticals and to pharmaceutical compositions comprising them.
Inventor(s): Garcia-Echeverria; Carlos (Basel, CH), Kanazawa; Takanori (Tsukuba, JP), Kawahara; Eiji (Tsukuba, JP), Masuya; Keiichi (Tsukuba, JP), Matsuura; Naoko (Tsukuba, JP), Miyake; Takahiro (Tsukuba, JP), Ohmori; Osamu (Tsukuba, JP), Umemura; Ichiro (Tsukuba, JP)
Assignee: Novartis AG (Basel, CH)
Application Number:10/549,250
Patent Claims: 1. A compound of formula I ##STR00545## each of R.sup.0 or R.sup.2 independently is hydrogen, C.sub.1-C.sub.8alkyl, unsubstituted or substituted 5 or 6 membered heterocyclyl comprising 1 or 2 hetero atoms selected from N, O and S, C.sub.1-C.sub.8alkoxy, unsubstituted or substituted heterocyclyloxy, unsubstituted or substituted heterocyclylC.sub.1-C.sub.8alkoxy, unsubstituted or substituted amino, or halogen; R.sup.1 is hydrogen, C.sub.1-C.sub.8alkyl, haloC.sub.1-C.sub.8alkyl, unsubstituted or substituted 5 or 6 membered heterocyclyl comprising 1 or 2 hetero atoms selected from N, O and S, C.sub.1-C.sub.8alkoxy, unsubstituted or substituted heterocyclyloxy, unsubstituted or substituted HeterocyclylC.sub.1-C.sub.8alkoxy, unsubstituted or substituted amino, halogen; R.sup.3 is C.sub.1-C.sub.8alkylsulfinyl, C.sub.1-C.sub.8alkylsulfonyl, C.sub.5-C.sub.10 arylsulfonyl, or unsubstituted or substituted carbamoyl; R.sup.4 is hydrogen; R.sup.5 is chloro or bromo; R.sup.6 is hydrogen; each of R.sup.7 and R.sup.9 independently is hydrogen, C.sub.1-C.sub.8alkyl, haloC.sub.1-C.sub.8alkyl, unsubstituted or substituted C.sub.5-C.sub.10aryl, unsubstituted or substituted 5 or 6 membered heterocyclyl comprising 1 or 2 hetero atoms selected from N, O and S, C.sub.1-C.sub.8alkoxy, unsubstituted or substituted heterocyclyloxy, unsubstituted or substituted heterocyclylC.sub.1-C.sub.8alkoxy, unsubstituted or substituted amino, halogen, unsubstituted or substituted carbamoyl, or unsubstituted or substituted sulfamoyl; R.sup.8 is C.sub.5-C.sub.10aryl; unsubstituted or substituted 5 or 6 membered heterocyclyl comprising 1 or 2 hetero atoms selected from N, O and S; C.sub.5-C.sub.10aryloxy; unsubstituted or substituted heterocyclyloxy; or unsubstituted or substituted heterocyclylC.sub.1-C.sub.8alkoxy; and R.sup.10 is C.sub.1-C.sub.8alkyl, haloC.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, unsubstituted or substituted heterocyclylC.sub.1-C.sub.8alkoxy, unsubstituted or substituted amino, or halogen; and A is C; or salts thereof.

2. The compound of claim 1, wherein each of R.sup.0, R.sup.1 or R.sup.2 is hydrogen.

3. The compound of claim 1, wherein R.sup.3 is C.sub.1-C.sub.8alkylsulfonyl, C.sub.5-C.sub.10arylsulfonyl or unsubstituted or substituted carbamoyl.

4. The compound of claim 1, wherein R.sup.3 is C.sub.1-C.sub.8alkylsulfonyl.

5. The compound of claim 1, wherein R.sup.3 is C.sub.5-C.sub.10arylsulfonyl.

6. The compound of claim 1, wherein R.sup.3 is unsubstituted or substituted carbamoyl.

7. The compound of claim 1, wherein R.sup.8 is piperidino, piperazino, N-methylpiperazino, morpholino, phenoxy, 1-methyl-4-piperidyloxy, 3-morpholinopropoxy, 2-morpholinoethoxy or 3-(N-methylpiperazino)-propoxy.

8. The compound of claim 1, wherein R.sup.8 is unsubstituted or substituted 5 or 6 membered heterocyclyl comprising 1 or 2 hetero atoms selected from N, O and S.

9. The compound of claim 1, wherein R.sup.0, R.sup.1 or R.sup.2 is hydrogen; R.sup.3 is C.sub.1-C.sub.8alkylsulfonyl; and R.sup.8 is unsubstituted or substituted 5 or 6 membered heterocyclyl comprising 1 or 2 hetero atoms selected from N, O and S.

10. The compound of claim 9, wherein R.sup.8 is piperidino, piperazino, N-methylpiperazino or morpholino.

11. The compound of claim 1, wherein said compound is selected from the group of compounds with the following names or formulae: 2-[5-chloro-2-(2-methoxy-4-morpholin-4-yl -phenylamino)-pyrimidin-4-ylamino]-N-methyl -benzamide; a compound of the formula ##STR00546## wherein Rx has one of the meanings given in the following table: TABLE-US-00038 Compound No. Rx 7-1 ##STR00547## 7-2 ##STR00548## 7-3 ##STR00549## 7-4 ##STR00550## 7-5 ##STR00551## 7-7 ##STR00552## 7-8 ##STR00553## 7-9 ##STR00554## 7-10 ##STR00555## 7-11 ##STR00556## 7-12 ##STR00557## 7-13 ##STR00558## 7-14 ##STR00559## 7-17 ##STR00560## 7-18 ##STR00561## 7-20 ##STR00562## 7-21 ##STR00563## 7-25 ##STR00564## 7-26 ##STR00565##

a compound of the formula ##STR00566## wherein Rx has one of the meanings given in the following table: TABLE-US-00039 Compound Rx 8-2 ##STR00567##

a compound of the formula ##STR00568## wherein Rx has one of the meanings given in the following table: TABLE-US-00040 Compound Rx 9-1 ##STR00569## 9-2 ##STR00570## 9-3 ##STR00571## 9-4 ##STR00572## 9-5 ##STR00573## 9-6 ##STR00574##

a compound of the formula ##STR00575## wherein Rx has one of the meanings given in the following table: TABLE-US-00041 Compound Rx 10-1 ##STR00576## 10-2 ##STR00577## 10-3 ##STR00578##

a compound of the formula ##STR00579## wherein Rx has one of the meanings given in the following table: TABLE-US-00042 Compound Rx 11-1 ##STR00580## 11-2 ##STR00581## 11-4 ##STR00582##

a compound of the formula ##STR00583## wherein Ry has one of the meanings given in the following table: TABLE-US-00043 Compound R 14-1 ##STR00584## 14-2 ##STR00585## 14-3 ##STR00586## 14-5 ##STR00587## 14-6 ##STR00588##

a compound of the formula ##STR00589## wherein Rx has one of the meanings given in the following table: TABLE-US-00044 Compound Rx 15-1 ##STR00590## 15-2 ##STR00591## 15-3 ##STR00592##

a compound of the formula ##STR00593## wherein Rx has one of the meanings given in the following table: TABLE-US-00045 Compound Rx 18-1 ##STR00594##

a compound of the formula ##STR00595## wherein Rx has one of the meanings given in the following table: TABLE-US-00046 Compound Rx 26-1 ##STR00596## 26-2 ##STR00597## 26-3 ##STR00598## 26-4 ##STR00599## 26-5 ##STR00600## 26-6 ##STR00601## 26-7 ##STR00602## 26-8 ##STR00603## 26-9 ##STR00604## 26-10 ##STR00605## 26-11 ##STR00606## 26-12 ##STR00607## 26-13 ##STR00608## 26-14 ##STR00609## 26-18 ##STR00610## 26-21 ##STR00611## 26-22 ##STR00612## 26-23 ##STR00613## 26-24 ##STR00614## 26-25 ##STR00615## 26-26 ##STR00616## 26-27 ##STR00617## 26-28 ##STR00618## 26-29 ##STR00619##

a compound of the formula ##STR00620## wherein Rx has one of the meanings given in the following table: TABLE-US-00047 Compound Rx 27-1 ##STR00621## 27-2 ##STR00622## 27-3 ##STR00623## 27-4 ##STR00624## 27-5 ##STR00625## 27-6 ##STR00626## 27-8 ##STR00627## 27-9 ##STR00628##

a compound of the formula ##STR00629## wherein Rx has one of the meanings given in the following table: TABLE-US-00048 Compound Rx 28-1 ##STR00630## 28-2 ##STR00631## 28-3 ##STR00632## 28-4 ##STR00633## 28-5 ##STR00634## 28-6 ##STR00635## 28-8 ##STR00636## 28-9 ##STR00637## 28-10 ##STR00638## 28-11 ##STR00639## 28-12 ##STR00640## 28-13 ##STR00641## 28-14 ##STR00642## 28-15 ##STR00643## 28-16 ##STR00644## 28-17 ##STR00645## 28-18 ##STR00646## 28-19 ##STR00647## 28-20 ##STR00648## 28-21 ##STR00649## 28-22 ##STR00650## 28-23 ##STR00651## 28-24 ##STR00652## 28-25 ##STR00653## 28-27 ##STR00654## 28-28 ##STR00655##

a compound of the formula ##STR00656## wherein Rx has one of the meanings given in the following table: TABLE-US-00049 Compound Rx 29-1 ##STR00657## 29-2 ##STR00658## 29-3 ##STR00659##

a compound of the formula ##STR00660## wherein Rx has one of the meanings given in the following table: TABLE-US-00050 Compound Rx 31-2 ##STR00661##

a compound of the formula ##STR00662## wherein Rx has one of the meanings given in the following table: TABLE-US-00051 Compound Rx 32-1 ##STR00663## 32-2 ##STR00664##

a compound of the formula ##STR00665## wherein Ry has one of the meanings given in the following table: TABLE-US-00052 Compound Ry 34-1 ##STR00666## 34-3 ##STR00667## 34-4 ##STR00668## 34-6 ##STR00669##

a compound of the formula ##STR00670## wherein Rx has one of the meanings given in the following table: TABLE-US-00053 Compound Rx 35-1 ##STR00671##

or a pharmaceutically acceptable salt thereof.

12. The compound of claim 1, wherein said compound is 2-[5-chloro-2-(2-methoxy-4-morpholin-4-yl -phenylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide, or N.sup.2-(4-[1,4']Bipiperidinyl-1'-yl-2-methoxy-phenyl)-5-chloro-N.sup.4-[- 2-(propane-1-sulfonyl)-phenyl]-pyrimidine-2,4-diamine, or a pharmaceutically acceptable salt thereof.

13. A process for the production of a compound of formula I according to claim 1, comprising reacting a compound of formula II ##STR00672## wherein R.sup.0, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are as defined in claim 1, and Y is a leaving group, with a compound of formula III ##STR00673## wherein A, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as defined in claim 1; and, if desired, converting a compound of formula I, wherein the substituents have the meaning as defined in claim 1, into another compound of formula I as defined in claim 1; and recovering the resulting compound of formula I in free from or as a salt, and, when required, converting the compound of formula I obtained in free form into the desired salt, or an obtained salt into the free form.

14. A pharmaceutical composition comprising a compound according to claim 1, as active ingredient together with one or more pharmaceutically acceptable diluents or carriers.

15. A combination comprising a therapeutically effective amount of a compound according to claim 1 and one or more known drug substances, said further drug substance being useful in the treatment of neoplastic diseases or immune system disorders.

16. A method for the treatment of breast tumors in a subject in need thereof which comprises administering an effective amount of a compound according to claim 1 or a pharmaceutical composition comprising same.

17. The method of claim 16, wherein said compound is 2-[5-chloro-2-(2-methoxy-4-morpholin-4-yl -phenylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide, or N.sup.2-(4-[1,4']Bipiperidinyl-1'-yl-2-methoxy-phenyl)-5-chloro-N.sup.4-[- 2-(propane-1-sulfonyl)-phenyl]-pyrimidine-2,4-diamine, or a pharmaceutically acceptable salt thereof.
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