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Generated: August 21, 2019

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Claims for Patent: 7,186,740

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Summary for Patent: 7,186,740
Title:Imidazopyrazines as cyclin dependent kinase inhibitors
Abstract: In its many embodiments, the present invention provides a novel class of imidazo[1,2-a] pyrazine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.
Inventor(s): Paruch; Kamil (Garwood, NJ), Guzi; Timothy J. (Chatham, NJ), Dwyer; Michael P. (Scotch Plains, NJ), Doll; Ronald J. (Convent Station, NJ), Girijavallabhan; Viyyoor M. (Parsippany, NJ)
Assignee: Schering Corporation (Kenilworth, NJ)
Application Number:10/666,424
Patent Claims:1. A compound represented by the structural formula ##STR00036## wherein: R is selected from the group consisting of alkyl. CF.sub.3, cycloalkyl, cycloalkylalkyl, arylalkyl, and --C(O)R.sup.7, wherein each of said alkyl, arylalkyl, and cycloalkyl can be unsubstituted or optionally independently substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of halogen, alkyl, cycloalkyl, CF.sub.3, CN, --OCF.sub.3, --OR.sup.6, --C(O)R.sup.7, --NR.sup.5R.sup.6, --C(O.sub.2)R.sup.6,--C(O)NR.sup.5R.sup.6, --(CHR.sup.5).sub.nOR.sup.6, --SR.sup.5, --S(O.sub.2)R.sup.7, --S(O.sub.2)NR.sup.5R.sup.6, --N(R.sup.5)S(O.sub.2)R.sup.7, --N(R.sup.5)C(O)R.sup.7 and --N(R.sup.5)C(O)NR.sup.5R.sup.6; R.sup.1 is H, halogen or alkyl; R.sup.2 is selected from the group consisting of H, halogen, CN, cycloalkyl, heterocyclyl, alkynyl and --CF.sub.3; R.sup.3 is selected from the group consisting of aryl (with the exception of phenyl), heteroaryl (with the exception of furyl), heterocyclyl, --(CHR.sup.5).sub.n-- heteroaryl, --S(O.sub.2)R.sup.6, --C(O)R.sup.6, --S(O.sub.2)NR.sup.5R.sup.6, --C(O)OR.sup.6, --C(O)NR.sup.5R.sup.6, ##STR00037## wherein each of said aryl, heteroaryl and heterocyclyl can be unsubstituted or optionally substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of halogen, alkyl, aryl, cycloalkyl, CF.sub.3, CN, --OCF.sub.3, --OR.sup.5, --NR.sup.5R.sup.6, --C(O.sub.2)R.sup.5, --C(O)NR.sup.5R.sup.6, --SR.sup.6, --S(O.sub.2)R.sup.6, --S(O.sub.2)NR.sup.5R.sup.6, --N(R.sup.5)S(O.sub.2)R.sup.7, --N(R.sup.5)C(O)R.sup.7 and --N(R.sup.5)C(O)NR.sup.5R.sup.6, with the proviso that when R.sup.3 is --(CHR.sup.5).sub.n-heteroaryl, R.sup.2 can additionally be alkyl; R.sup.5is H or alkyl; R.sup.6 is selected from the group consisting of H, alkyl, aryl, heteroaryl, arylalkyl and heteroarylalkyl, wherein each of said alkyl, heteroarylalkyl, aryl, heteroaryl and arylalkyl can be unsubstituted or optionally substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of halogen, alkyl, aryl, cycloalkyl, CF.sub.3, OCF.sub.3, CN, --OR.sup.5, --NR.sup.5R.sup.6, --CH.sub.2OR.sup.5, --C(O.sub.2)R.sup.5, --C(O)NR.sup.5R.sup.6, --SR.sup.6, --S(O.sub.2)R.sup.7, --S(O.sub.2)NR.sup.5R.sup.6, --N(R.sup.5)S(O.sub.2)R.sup.7, --N(R.sup.5)C(O)R.sup.7 and --N(R.sup.5)C(O)NR.sup.5R.sup.6; R.sup.7 is selected from the group consisting of alkyl, aryl, heteroaryl, arylalkyl and heteroarylalkyl, wherein each of said alkyl, heteroarylalkyl, aryl, heteroaryl and arylalkyl can be unsubstituted or optionally substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of halogen, alkyl, aryl, cycloalkyl, CF.sub.3, OCF.sub.3, CN, --OR.sup.5, --NR.sup.5R.sup.6, --CH.sub.2OR.sup.5, --C(O.sub.2)R.sup.5, --C(O)NR.sup.5R.sup.6, --SR.sup.6, --S(O.sub.2)R.sup.7, --S(O.sub.2)NR.sup.5R.sup.6, --N(R.sup.5)S(O.sub.2)R.sup.7, --N(R.sup.5)C(O)R.sup.7 and --N(R.sup.5)C(O)NR.sup.5R.sup.6; R.sup.8 is selected from the group consisting of R.sup.6, --C(O)NR.sup.5R.sup.6, --S(O.sub.2)NR.sup.5R.sup.6, --C(O)R.sup.7, --C(O.sub.2)R.sup.6, --S(O.sup.2)R.sup.7 and --(CH.sub.2)-aryl; m is 0 to 4; and n is 1 4.

2. The compound of claim 1, wherein R is selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl and arylalkyl, wherein each of said alkyl, cycloalkyl, and arylalkyl can be unsubstituted or optionally independently substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of halogen, alkyl, cycloalkyl, CF.sub.3, CN, --OCF.sub.3, --OR.sup.6, --C(O)R.sup.7, --NR.sup.5R.sup.6, --C(O.sub.2)R.sup.5, --C(O)NR.sup.5R.sup.6, --SR.sup.6, --S(O.sub.2)R.sup.7, --S(O.sub.2)N R.sup.5R.sup.6, --N(R.sup.5)S(O.sup.2)R.sup.7, --N(R.sup.5)C(O)R.sup.7 and --N(R.sup.5)C(O)NR.sup.5R.sup.6; R.sup.1 is H or halogen; R.sup.2 is selected from the group consisting of H, halogen, cycloalkyl, CN, alkynyl and --CF.sup.3; R.sup.3 is selected from the group consisting of aryl, heteroaryl, heterocyclyl, --(CHR.sup.5).sub.n-heteroaryl, --S(O.sub.2)R.sup.6, --C(O)R.sup.6, --S(O.sup.2)NR.sup.5R.sup.6, --C(O)OR.sup.6, --C(O)NR.sup.5R.sup.6, ##STR00038## wherein each of said aryl, heteroaryl and heterocyclyl can be unsubstituted or optionally substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of halogen, alkyl, aryl, cycloalkyl, CF.sub.3, CN, --OCF.sub.3, --N(R.sup.5)C(O)R.sup.7, --C(O)NR.sup.5R.sup.6, --S(O.sub.2)R.sup.6, and --N(R.sup.5)C(O)R.sup.7; R.sup.5 is H or lower alkyl; m is 0 to 2; and n is 1 to 3.

3. The compound of claim 2, wherein R is alkyl, arylalkyl or cycloalkylalkyl.

4. The compound of claim 3, wherein R is selected from the group consisting of methyl, ethyl, t-butyl, cyclohexylmethyl, benzyl and phenethyl.

5. The compound of claim 2, wherein R.sup.1 is H.

6. The compound of claim 2, wherein R.sup.1 is methyl.

7. The compound of claim 2, wherein R.sup.2 is H, F, Cl, Br or I.

8. The compound of claim 7, wherein R.sup.2 is Br.

9. The compound of claim 8, wherein R.sup.3 is (pyrid-2-yl)methyl, (pyrid-3-yl)methyl, (pyrid-4-yl )methyl, thien-2-yl or thien-3yl, wherein said pyridyl and thienyl can be unsubstituted or optionally independently substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of F, Cl, Br, CF.sub.3, lower alkyl, methoxy and CN.

10. The compound of claim 9, wherein R.sup.3 is (pyrid-2-yl)methyl.

11. The compound of claim 9, wherein R.sup.3 is (pyrid-3-yl)methyl.

12. The compound of claim 9, wherein R.sup.3 is (pyrid-4-yl)methyl.

13. The compound of claim 2, wherein m is 0.

14. The compound of claim 2, wherein n is 1.

15. A compound of the formula: ##STR00039## ##STR00040## or a pharmaceutically acceptable salt thereof.

16. A pharmaceutical composition comprising a therapeutically effective amount of at least one compound of claim 1 in combination with at least one pharmaceutically acceptable carrier.

17. The pharmaceutical composition of claim 16, additionally comprising one or more anti-cancer agents selected from the group consisting of a cytostatic agent, cisplatin, doxorubicin, taxotere, taxol, etoposide, CPT-11, irinotecan, camptostar, topotecan, paclitaxel, docetaxel, epothilones, tamoxifen, 5-fluorouracil, methoxtrexate, 5FU, temozolomide, cyclophosphamide, SCH 66336, R115777, L778,123, BMS 214662, Iressa, Tarceva, antibodies to EGFR, Gleevec, intron, ara-C, adriamycin, cytoxan, gemcitabine, Uracil mustard, Chlormethine, Ifosfamide, Melphalan, Chlorambucil, Pipobroman, Triethylenemelamine, Triethylenethiophosphopramine, Busulfan, Carmustine, Lomustine, Streptozocin, Dacarbazine, Floxuridine, Cytarabine, 6-Mercaptopurine, 6-Thioguanine, Fludarabine phosphate, Pentostatine, Vinblastine, Vincristine, Vindesine, Bleomycin, Dactinomycin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mithramycin, Deoxycoformycin, Mitomycin-C, L-Asparaginase, Teniposide 17.alpha.-Ethinylestradiol, Diethylstilbestrol, Testosterone, Prednisone, Fluoxymesterone, Dromostanolone propionate, Testolactone, Megestrolacetate, Methylprednisolone, Methyltestosterone, Prednisolone, Triamcinolone, Chlorotrianisene, Hydroxyprogesterone, Aminoglutethimide, Estramustine, Medroxyprogesteroneacetate, Leuprolide, Flutamide, Toremifene, goserelin, Cisplatin, Carboplatin, Hydroxyurea, Amsacrine, Procarbazine, Mitotane, Mitoxantrone, Levamisole, Navelbene, CPT-11, Anastrazole, Letrazole, Capecitabine, Reloxafine, Droloxafine, or Hexamethylmelamine.

18. A compound of claim 1 in purified form.

Details for Patent 7,186,740

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Merck ELSPAR asparaginase VIAL 101063 001 1978-01-10   Try a Free Trial Schering Corporation (Kenilworth, NJ) 2036-04-30 RX search
Schering INTRON A interferon alfa-2b VIAL 103132 001 1986-06-04   Try a Free Trial Schering Corporation (Kenilworth, NJ) 2036-04-30 RX search
Schering INTRON A interferon alfa-2b VIAL 103132 002 1986-06-04   Try a Free Trial Schering Corporation (Kenilworth, NJ) 2036-04-30 RX search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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