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Last Updated: October 23, 2019

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Claims for Patent: 7,820,646

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Summary for Patent: 7,820,646
Title:Cyclized derivatives as Eg-5 inhibitors
Abstract: The present invention relates to new substituted imidazole compounds have the following Formula (I) and to the pharmaceutically acceptable salts, esters, or prodrugs thereof, to compositions of the compounds together with pharmaceutically acceptable carriers, and to uses of the compounds: ##STR00001##
Inventor(s): Boyce; Rustum (Singapore, SG), Martin; Eric (El Cerrito, CA), Wang; Weibo (Moraga, CA), Yang; Hong (Fremont, CA), Barsanti; Paul A. (Pleasant Hill, CA)
Assignee: Novartis Vaccines and Diagnostics, Inc. (Emeryville, CA)
Application Number:11/969,164
Patent Claims:1. A compound of Formula (I): ##STR00135## or a pharmaceutically acceptable salt thereof, wherein: R.sup.1 is selected from the group consisting of alkyl and substituted alkyl; R.sup.2 is selected from the group consisting of hydrogen, alkyl, and substituted alkyl; L is selected from the group consisting of a) --O--; b) --OCH.sub.2--, --CH.sub.2O--, --C(O)NR.sup.7--; c) --CH.sub.2OCH.sub.2--, --CH.sub.2NR.sup.7CH.sub.2--, --CH.sub.2CH.sub.2O--, --C(O)NR.sup.7CH.sub.2--, and --CH.sub.2CH.sub.2NR.sup.7--; R.sup.3 and R.sup.4 are independently selected from the group consisting of halo, alkyl, and substituted alkyl; R.sup.5 and R.sup.6 are independently selected from the group consisting of cyano, alkyl, substituted alkyl, alkoxy, substituted alkoxy, halo, and hydroxy; R.sup.7 is selected from the group consisting of hydrogen, alkyl, and --SO.sub.2alkyl; m is 0, 1, 2, or 3; n is 0, 1, 2, or 3; and p is 0 or 1.

2. A compound of claim 1 wherein R.sup.1 and R.sup.2 are alkyl.

3. A compound of claim 1 wherein R.sup.1 is alkyl and R.sup.2 is hydrogen.

4. A compound of claim 3 wherein R.sup.1 is selected from the group consisting of isopropyl, t-butyl, and propyl.

5. A compound of claim 1 wherein R.sup.4 is substituted alkyl.

6. A compound of claim 5 wherein R.sup.4 is alkyl substituted with 1 to 5 substituents selected from the group consisting of amino, substituted amino, halo, alkoxy, substituted alkoxy, and hydroxy.

7. A compound of claim 1 wherein R.sup.4 is selected from the group consisting of halo, --CH.sub.2NH.sub.2, --(CH.sub.2).sub.2NH.sub.2, --(CH.sub.2).sub.3NH.sub.2, and --CH.sub.2OH.

8. A compound of claim 1 wherein m is 0.

9. A compound of claim 1 wherein R.sup.6 is halo.

10. A compound of claim 1 wherein R.sup.6 and the phenyl ring to which it is attached is selected from the group consisting of phenyl, 3-bromophenyl, 3-chlorophenyl, 4-cyanophenyl, 2,5-difluorophenyl, 3-fluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, and 3-trifluoromethylphenyl.

11. A compound of claim 1, wherein L and the atoms to which it is joined form a ring selected from the group consisting of ##STR00136## ##STR00137## ##STR00138##

12. A compound of claim 1 having Formula (Ia) or a pharmaceutically acceptable salt thereof: ##STR00139##

13. A compound of claim 1 having Formula (Ib)-(Id) or a pharmaceutically acceptable salt thereof: ##STR00140##

14. A compound of claim 1 having Formula (Ie)-(Ii) or a pharmaceutically acceptable salt thereof: ##STR00141## ##STR00142##

15. A compound that is (S)-5-(aminomethyl)-3-((R)-1-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol- -2-yl)-2,2-dimethylpropyl)oxazolidin-2-one or a pharmaceutically acceptable salt thereof: ##STR00143##

16. A compound that is (R)-5-(aminomethyl)-3-((R)-1-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol- -2-yl)-2,2-dimethylpropyl)oxazolidin-2-one or a pharmaceutically acceptable salt thereof: ##STR00144##

17. A compound claim 1 selected from: (5R)-5-(2-aminoethyl)-3-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-- dimethylpropyl]-1,3-oxazolidin-2-one; (5S)-5-(2-aminoethyl)-3-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-- dimethylpropyl]-1,3-oxazolidin-2-one; 5-(aminomethyl)-3-{(1R)-1-[1-benzyl-4-(3-chlorophenyl)-1H-imidazol-2-yl]-- 2-methylpropyl}-1,3-oxazolidin-2-one; (5S)-5-(aminomethyl)-3-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1,3-oxazinan-2-one; (5R)-5-(aminomethyl)-3-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1,3-oxazinan-2-one; (6S)-6-(aminomethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]morpholin-3-one; (6R)-6-(aminomethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]morpholin-3-one; (6R)-6-(aminomethyl)-4-{(1R)-1-[1-benzyl-4-(3-chlorophenyl)-1H-imidazol-2- -yl]-2-methylpropyl}morpholin-3-one; (6S)-6-(aminomethyl)-4-{(1R)-1-[1-benzyl-4-(3-chlorophenyl)-1H-imidazol-2- -yl]-2-methylpropyl}morpholin-3-one; (6R)-6-(2-aminoethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-- dimethylpropyl]morpholin-3-one; (6S)-6-(2-aminoethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-- dimethylpropyl]morpholin-3-one; (6S)-6-(2-aminoethyl)-4-{(1R)-1-[1-benzyl-4-(3-chlorophenyl)-1H-imidazol-- 2-yl]-2-methylpropyl}morpholin-3-one; (6R)-6-(2-aminoethyl)-4-{(1R)-1-[1-benzyl-4-(3-fluorophenyl)-1H-imidazol-- 2-yl]-2-methylpropyl}morpholin-3-one; (2S,6R)-6-(aminomethyl)-4-{(1R)-1-[1-benzyl-4-(3-fluorophenyl)-1H-imidazo- l-2-yl]-2,2-dimethylpropyl}-2-methylmorpholin-3-one; (2R,6R)-6-(aminomethyl)-4-{(1R)-1-[1-benzyl-4-(3-fluorophenyl)-1H-imidazo- l-2-yl]-2,2-dimethylpropyl}-2-methylmorpholin-3-one; (5R)-5-(aminomethyl)-1-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]piperazine-2,3-dione; (5S)-5-(aminomethyl)-1-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]piperazine-2,3-dione; (5R)-5-(aminomethyl)-1-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-4-methylpiperazine-2,3-dione; (2S)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-dimethylpropyl]-2- -(hydroxymethyl)-1,4-diazepan-5-one; (2R)-2-(aminomethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1,4-diazepan-5-one; (2R)-2-(aminomethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1-(methylsulfonyl)-1,4-diazepan-5-one; (2S)-2-(aminomethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1,4-oxazepan-5-one; (2R)-2-(aminomethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1,4-oxazepan-5-one; (6S)-6-(aminomethyl)-4-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1,4-oxazepan-3-one; (6R)-6-(aminomethyl)-4-{(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl}-1,4-oxazepan-3-one; (6R)-6-(aminomethyl)-4-{(1R)-1-[1-(3,5-difluorobenzyl)-4-(3-fluorophenyl)- -1H-imidazol-2-yl]-2,2-dimethylpropyl}-1,4-oxazepan-3-one; (6R)-6-(aminomethyl)-4-{(1R)-1-[1-benzyl-4-(3-fluorophenyl)-1H-imidazol-2- -yl]-2,2-dimethylpropyl}-1,4-oxazepan-3-one; (6R)-6-(aminomethyl)-4-{(1R)-1-[1-(3-fluorobenzyl)-4-(3-fluorophenyl)-1H-- imidazol-2-yl]-2,2-dimethylpropyl}-1,4-oxazepan-3-one; (6S)-6-(aminomethyl)-4-{(1R)-1-[1-(3-fluorobenzyl)-4-(3-fluorophenyl)-1H-- imidazol-2-yl]-2,2-dimethylpropyl}-1,4-oxazepan-3-one; (6S)-6-(aminomethyl)-1-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-d- imethylpropyl]-1,4-diazepane-2,3-dione; (6R)-1-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-dimethylpropyl]-6- -fluoro-1,4-diazepan-2-one; or (6S)-1-[(1R)-1-(1-benzyl-4-phenyl-1H-imidazol-2-yl)-2,2-dimethylpropyl]-6- -fluoro-1,4-diazepan-2-one; or a pharmaceutically acceptable salt thereof.

18. A pharmaceutical composition comprising a therapeutically effective amount of a compound of any one of claims 1 to 17 and a pharmaceutically acceptable carrier.

19. The composition of claim 18 further comprising at least one additional agent for the treatment of cancer.

20. The composition of claim 19, wherein the additional agent for the treatment of cancer is selected from the group consisting of irinotecan, topotecan, gemcitabine, imatinib, trastuzumab, 5-fluorouracil, leucovorin, carboplatin, cisplatin, docetaxel, paclitaxel, tezacitabine, cyclophosphamide, vinca alkaloids, anthracyclines, rituximab, and trastuzumab.

Details for Patent 7,820,646

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech RITUXAN rituximab VIAL 103705 001 1997-11-26   Start Trial Novartis Vaccines and Diagnostics, Inc. (Emeryville, CA) 2027-01-05 RX search
Genentech HERCEPTIN trastuzumab VIAL; INTRAVENOUS 103792 001 1998-09-25   Start Trial Novartis Vaccines and Diagnostics, Inc. (Emeryville, CA) 2027-01-05 RX Orphan search
Genentech Inc RITUXAN HYCELA rituximab; hyaluronidase (human recombinant) SOLUTION;SUBCUTANEOUS 761064 001 2017-06-22   Start Trial Novartis Vaccines and Diagnostics, Inc. (Emeryville, CA) 2027-01-05 RX Orphan search
Genentech Inc RITUXAN HYCELA rituximab; hyaluronidase (human recombinant) SOLUTION;SUBCUTANEOUS 761064 002 2017-06-22   Start Trial Novartis Vaccines and Diagnostics, Inc. (Emeryville, CA) 2027-01-05 RX Orphan search
Genentech Inc HERCEPTIN HYLECTA trastuzumab;hyaluronidase-oysk INJECTABLE;SUBCUTANEOUS 761106 001 2019-02-28   Start Trial Novartis Vaccines and Diagnostics, Inc. (Emeryville, CA) 2027-01-05 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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