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Last Updated: March 28, 2024

Claims for Patent: 7,189,716


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Summary for Patent: 7,189,716
Title:Tyrosine kinase inhibitors
Abstract: The present invention provides compounds of formula I ##STR00001## and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase enzymes thereby making them useful as anti-cancer agents.
Inventor(s): Beaulieu; Francis (LaPrairie, CA), Ouellet; Carl (Boucherville, CA), Zimmermann; Kurt (Durham, CT), Velaparthi; Upender (North Haven, CT), Wittman; Mark D. (Wallingford, CT)
Assignee: Bristol-Myers Squibb Company (Princeton, NJ)
Application Number:10/751,798
Patent Claims:1. A compound according to formula I: ##STR00074## its enantiomers, diastereomers, pharmaceutically acceptable salts, hydrates, prodrugs and solvates thereof; wherein A, B, and are each C; D is N; X is selected from the group consisting of N or C wherein each of said N or C may be optionally substituted, independently, with R.sup.7 and n is 0, 1, 2, or 3; Y is selected from the group consisting of O and S; W is selected from the group consisting of N, C, O, and S, provided that when W is O or S, R.sup.41 is absent; R.sup.3 is morpholine R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.41, and R.sup.42 are each independently selected from the group consisting of H, C.sub.1-6 alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, halo, amino, aminoalkyl, alkoxy, thioalkoxy, nitro, aryl, heteroaryl, alkoxyalkyl, thioalkoxyalkyl, aminoalkyl, aralkyl, heteroarylalkyl, heterocycloalkylalkyl, --CN, --CO.sub.2R.sup.8, --CONR.sup.9R.sup.10, --CO.sub.2NR.sup.11R.sup.12, --NR.sup.13CONR.sup.14R.sup.15, --NR.sup.16SO.sub.2R.sup.17, --SO.sub.2NR.sup.18R.sup.19, --C(NR.sup.20)NR.sup.21R.sup.22, --NH-Z, --NH-Z-aryl, and NH-Z-heteroaryl, or any two of R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, or R.sup.4 and R.sup.5 can be taken together to form a heterocyclic ring having at least one nitrogen atom; Z is selected from the group consisting of C.sub.1 C.sub.6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, and alkynyl; Z optionally having one or more hydroxy, thiol, alkoxy, thioalkoxy, amino, halo, NR.sup.23S.sub.2R.sup.24 groups and optionally incorporating one or more groups selected from --CO, --CNOH, --CNOR.sup.26, --CNNR.sup.27, --CNNCOR.sup.28 or --CNNSO.sub.2R.sup.29; R.sup.8,R.sup.9,R.sup.10,R.sup.11,R.sup.12,R.sup.13,R.sup.14,R.sup.15,R.s- up.16,R.sup.17,R.sup.18,R.sup.19,R.sup.20,R.sup.21,R.sup.22,R.sup.23,R.sup- .24, and R.sup.26 are independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, hydroxy, alkoxy, aryl, heteroaryl, heterocyclyl, heteroarylalkyl, and alkyl-R.sup.25 wherein R.sup.25 is alkenyl, hydroxy, thiol, alkoxy, thioalkoxy, amino, alkylamino, dialkylamino, aryl, heteroaryl, cyano, halo, heteroaryl, heterocyloalkyl, sulfoxy, sulfonyl, --NR.sup.27COOR.sup.28, --NR.sup.29C(O)R.sup.30, --NR.sup.31SOI.sub.2R.sup.32, SO.sub.2NR.sup.31R.sup.32, --C(O)NR.sup.33R.sup.34, and; R.sup.27,R.sup.28,R.sup.29,R.sup.30,R.sup.31,R.sup.32,R.sup.33 and R.sup.34 are, independently, hydrogen, alkyl, or cycloalkyl.

2. The compound according to claim 1 wherein R.sup.1,R.sup.2,R.sup.4,R.sup.5,R.sup.41, and R.sup.42 are absent, H, or C.sub.1 to C.sub.4 alkyl; R.sup.3 is morpholine.

3. The compound according to claim 2 wherein R.sup.6 is --NH-Z-aryl.

4. The compound according to claim 3 wherein said aryl group is a phenyl group substituted at 1 or more positions on the ring.

5. The compound according to claim 4 wherein said substituent is a Br, F, Cl, or a methoxy group.

6. The compound according to claim 2 wherein R.sup.6 is selected from the group consisting of H, 2-aminomethylpyridine, NHCH.sub.2CH(OH)aryl, and NHCH(CH.sub.2OH)CH.sub.2aryl.

7. The compound according to claim 6 wherein said aryl is an optionally substituted phenyl.

8. The compound according to claim 7 wherein said phenyl is substituted with at least one of Br, Cl, F, alkoxy or --NHSO.sub.2CH.sub.3.

9. A compound selected from the group consisting of: 4-[2-(3-Chloro-phenyl)-2(S)-hydroxy-ethylamino]-3-(6-methyl-2-morpholin-4- -yl-9H-purin-8-yl)-1H-pyridin-2-one hydrochloride; 4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-methyl-6-morpholin-4-yl- -1H-imidazo[4,5-c]pyridin-2-yl)-1H-pyridin-2-one bis-hydrochloride.

10. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

11. The pharmaceutical composition according to claim 10 further comprising at least one other anti-cancer agent selected from the group consisting of tamoxifen, toremifen, raloxifene, droloxifene, jodoxyfene, megestrol acetate, anastroxole, letrazole, borazole, exemestane, flutamide, nilutamide, bicalutamide, cyproterone acetate, goserelin acetate, luprolide, finasteride, trastuzumab, methotrexate, 5-fluorouracil, cytosine arabinoside, doxorubicin, daunamycin, epirubicin, idarubicin, mitomycin-C, dactinomycin, mithramycin, cisplatin, carboplatin, melphalan, chlorambucil, busulphan, cyclophosphamide, ifosfamide, thiotephan, vincristine, paclitaxel, docetaxel, etoposide, teniposide, amsacrine, irinotecan, topotecan, gefitinib, and erlotinibformulated as a fixed dose.

Details for Patent 7,189,716

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Genentech, Inc. HERCEPTIN trastuzumab For Injection 103792 09/25/1998 ⤷  Try a Trial 2023-01-03
Genentech, Inc. HERCEPTIN trastuzumab For Injection 103792 02/10/2017 ⤷  Try a Trial 2023-01-03
Genentech, Inc. HERCEPTIN HYLECTA trastuzumab and hyaluronidase-oysk Injection 761106 02/28/2019 ⤷  Try a Trial 2023-01-03
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

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