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Last Updated: April 3, 2025

Claims for Patent: 8,247,400

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Summary for Patent: 8,247,400

Title:	Cephem compounds useful for the treatment of bacterial infections
Abstract:	The present invention relates to new cephem compounds useful for the treatment of bacterial infections of formula I: ##STR00001## The invention also relates to methods of preparing the compounds, pharmaceutical compositions comprising the compounds, and to methods of treatment using the compounds. The new cephem compounds are stable, exhibit good solubility, and are particularly well suited for, e.g., parenteral administration for the treatment of bacterial infections.
Inventor(s):	Dedhiya; Mahendra G. (Pomona, NY), Singh; Brahma N. (Syosset, NY)
Assignee:
Application Number:	12/710,417
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 8,247,400
Patent Claims:	1. A compound of formula (I): ##STR00007## wherein R.sup.1 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, --C(O)alkyl, --C(O)OH, --CH(NH.sub.2)(CH.sub.2).sub.3--NH--C(NH)NH.sub.2 or --CH(NH.sub.2)--CH.sub.2--C(O)NH.sub.2; wherein, when present, any alkyl, aryl, heteroaryl or heterocycle group may optionally be substituted by halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, arylamino, diarylamino, amido, carboxyl, alkyl, halogenated alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycle, heterocyclealkyl, aroyl, acyl, alkoxy, aryloxy, heteroaryloxy, cycloalkyloxy, cycloalkylalkyloxy, arylalkyloxy, heteroarylalkyloxy, thio, alkylhio, arylthio, alkylsulfinyl, alkylsulfonyl, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl, heteroarylsulfonyl, alkoxycarbonyl, aryloxycarbonyl or heteroaryloxycarbonyl; or a pharmaceutically acceptable salt thereof. 2. A compound according to claim 1, wherein R.sup.1 is hydrogen, alkyl or aryl. 3. A compound according to claim 1, wherein the compound is (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]a- cetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-- oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate or a pharmaceutically acceptable salt thereof. 4. A pharmaceutical composition comprising a compound selected from the group consisting of ceftaroline, ceftaroline fosamil, ceftaroline fosamil acetate, and a pharmaceutically acceptable salt and/or a prodrug thereof and a compound according to claim 3. 5. A pharmaceutical composition comprising ceftaroline fosamil or ceftaroline fosamil acetate and a compound according to claim 3. 6. The pharmaceutical composition according to claim 5 comprising up to about 10 mg of (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]a- cetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-- oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate or a pharmaceutically acceptable salt thereof. 7. The pharmaceutical composition according to claim 5 comprising up to about 5 mg of (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]a- cetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-- oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate or a pharmaceutically acceptable salt thereof. 8. The pharmaceutical composition according to claim 5 comprising up to about 2.5 mg of (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]a- cetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-- oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate or a pharmaceutically acceptable salt thereof. 9. The pharmaceutical composition according to claim 5 comprising up to about 1 mg of (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]a- cetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-- oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate or a pharmaceutically acceptable salt thereof. 10. A method of treating a bacterial infection comprising administering to a patient in need thereof a composition according to claim 8. 11. A method of treating a bacterial infection comprising administering to a patient in need thereof a composition according to claim 9. 12. A crystalline form of (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]a- cetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-- oxo-5-thia-1-azabicylo[4.2.0]oct-2-ene-2-carboxylate hydrochloride] characterized by a X-ray powder diffraction pattern with CuK.infin.radiation comprising characteristic peaks at about 9.6, about 20.6, about 21.9, about 23.0 and about 24.3.+-.0.2 degrees 2.theta.. 13. The method of claim 11 wherein the bacterial infection is selected from the group consisting of community acquired bacterial pneumonia and bacterial skin and skin structure infections. 14. The method of claim 13 wherein the pharmaceutical composition comprises 600 mg ceftaroline fosamil. 15. The method of claim 14 wherein the pharmaceutical composition is administered every 12 hours by intravenous infusion. 16. The method of claim 10 wherein the bacterial infection is selected from the group consisting of community acquired bacterial pneumonia and bacterial skin and skin structure infections. 17. The method of claim 16 wherein the pharmaceutical composition comprises 600 mg ceftaroline fosamil. 18. The method of claim 17 wherein the pharmaceutical composition is administered every 12 hours by intravenous infusion. 19. A method of treating a bacterial infection comprising administering to a patient in need thereof a pharmaceutical composition according to claim 7 wherein the bacterial infection is selected from the group consisting of community acquired bacterial pneumonia and bacterial skin and skin structure infections and the pharmaceutical composition comprises 600 mg ceftaroline fosamil. 20. The method of claim 13 wherein the pharmaceutical composition comprises 400 mg ceftaroline fosamil. 21. The method of claim 20 wherein the pharmaceutical composition is administered every 12 hours by intravenous infusion. 22. The method of claim 16 wherein the pharmaceutical composition comprises 400 mg ceftaroline fosamil. 23. The method of claim 22 wherein the pharmaceutical composition is administered every 12 hours by intravenous infusion.

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