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Generated: April 22, 2018

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Claims for Patent: 6,936,590

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Summary for Patent: 6,936,590
Title: C-aryl glucoside SGLT2 inhibitors and method
Abstract:A method is provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of a compound of the formula ##STR1## alone or in combination with one or more other antidiabetic agent(s) or other therapeutic agent(s).
Inventor(s): Washburn; William N. (Titusville, NJ), Ellsworth; Bruce (Princeton, NJ), Meng; Wei (Pennington, NJ), Wu; Gang (Princeton, NJ), Sher; Philip M. (Plainsboro, NJ)
Assignee: Bristol Myers Squibb Company (Princeton, NJ)
Application Number:10/264,410
Patent Claims: 1. A method for treating diabetes, diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, insulin resistance, hyperglycemia, hyperinsulinemia, hyperlipidemia, obesity, hypertriglyceridemia or atherosclerosis via the inhibition of SGLT2 transporters which comprises administering to a mammalian species in need of treatment a therapeutically effective amount of a compound of formula I having the structure ##STR116##

wherein R.sup.1, R.sup.2 and R.sup.2a are independently selected from the group consisting of hydrogen, OH, OR.sup.5, alkyl, CF.sub.3, OCHF.sub.2, OCF.sub.3, SR.sup.5i or halogen, or two of R.sup.1, R.sup.2 and R.sup.2a together with the carbons to which they are attached can form an annelated five, six or seven membered carbocycle or heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2 ; R.sup.1 and R.sup.4 are each independently selected from the group consisting of hydrogen, OH, OR.sup.5a,OAryl, OCH.sub.2 Aryl, alkyl, cycloalkyl, CF.sub.3, --OCHF.sub.2, --OCF.sub.3, halogen, --CN, --CO.sub.2 R.sup.5b, --CO.sub.2 H, COR.sup.6b, --CH(OH)R.sup.6c, --CH(OR.sup.5h)R.sup.6d, --CONR.sup.6 R.sup.6a, --NHCOR.sup.5c, --NHSO.sub.2 R.sup.5d, --NHSO.sub.2 Aryl, Aryl, --SR.sup.5e, --SOR.sup.5f, --SO.sub.2 R.sup.5g, --SO.sub.2 Aryl, and a five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2, or R.sup.3 and R.sup.4 together with the carbons to which they are attached form an annelated five, six or seven membered carbocycle or heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2 ; R.sup.5, R.sup.5a, R.sup.5b, R.sup.5c, R.sup.5d, R.sup.5e, R.sup.5f, R.sup.5g, R.sup.5h and R.sup.5i are independently alkyl; R.sup.6, R.sup.6a, R.sup.6b, R.sup.6c, and R.sup.6d are are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkylaryl and cycloalkyl, or R.sup.6 and R.sub.5a together with the nitrogen to which they are attached form an annelated five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2 ; and A is O or (CH.sub.2).sub.n where n is 0-3, or a pharmaceutically acceptable salt, stereoisomer, or prodrug ester thereof.

2. The method as defined in claim 1 comprising administering a therapeutically effective amount of a compound of formula I having the structure ##STR117##

3. A method for treating diabetes, via the inhibition of SGLT2 transporters which comprises administering to a mammalian species in need of treatment a therapeutically effective amount of a compound of formula I having the structure ##STR118##

wherein R.sup.1, R.sup.2 and R.sup.2a are independently selected from the group consisting of hydrogen, OH, OR.sup.5, alkyl, CF.sub.3, OCHF.sub.2, OCF.sub.3, SR.sup.5i and halogen, or two of R.sup.1, R.sup.2 and R.sup.2a together with the carbons to which they are attached can form an annelated five, six or seven membered carbocycle or heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2 ; R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, OH, OR.sup.5a, OAryl, OCH.sub.2 Aryl, alkyl, cycloalkyl, CF.sub.3, --OCHF.sub.2, --OCF.sub.3, halogen, --CN, --CO.sub.2 R.sup.5b, --CO.sub.2 H, COR.sup.6b, --CH(OH)R.sup.6c, --CH(OR.sup.5h)R.sup.6d, --CONR.sup.6 R.sup.6a, --NHCOR.sup.5c, --NHSO.sub.2 R.sup.5d, --NHSO.sub.2 Aryl, Aryl, --SR.sup.5e, --SOR.sup.5f, --SO.sub.2 R.sup.5g, --SO.sub.2 Aryl, and a five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2, or R.sup.3 and R.sup.4 together with the carbons to which they are attached form an annelated five, six or seven membered carbocycle or heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2 ; R.sup.5, R.sup.5a, R.sup.5b, R.sup.5c, R.sup.5d, R.sup.5e, R.sup.5f, R.sup.5g, R.sup.5h and R.sup.5i are independently alkyl; R.sup.6, R.sup.6a, R.sup.6b, R.sup.6c, and R.sup.6d are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkylaryl and cycloalkyl, or R.sup.6 and R.sub.5a together with the nitrogen to which they are attached form an annelated five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO.sub.2 ; and A is O or (CH.sub.2).sub.n where n is 0-3, or a pharmaceutically acceptable salt, stereoisomer, or prodrug ester thereof.

4. The method as defined in claim 1 comprising administering a therapeutically effective amount of a compound of formula I and at least one antidiabetic agent selected from the group consisting of metformin, glyburide, glimepiride, glipyride, glipizide, chlorpropamide, gliclazide, acarbose, miglitol, pioglitazone, troglitazone, rosiglitazone, insulin, isaglitazone, repaglinide and nateglinide.

5. The method as defined in claim 1 comprising administering a therapeutically effective amount of a compound of formula I and at least one anti-obesity agent selected from the group consisting of orlistat, sibutramine, topiramate, axokine, dexamphetamine, phentermine, phenylpropanolamine and mazindol.

6. The method as defined in claim 1 comprising administering a therapeutically effective amount of a compound of formula I and at least one lipid lowering agent selected from the group consisting of pravastatin, lovastatin, simvastatin, atorvastatin, cerivastatin, fluvastatin, nisvastatin, visastatin, atavastatin, rosuvastatin, fenofibrate, gemfibrozil, clofibrate and avasimibe.

7. The method as defined in claim 3 comprising administering a therapeutically effective amount of a compound of formula I and at least one antidiabetic agent selected from the group consisting of metformin, glyburide, glimepiride, glipyride, glipizide, chlorpropamide, gliclazide, acarbose, maglitol, pioglitazone, troglitazone, rosiglitazone, insulin, isaglitazone, repaglinide and nateglinide.

8. The method as defined in claim 3 comprising administering a therapeutically effective amount of a compound of formula I and at least one anti-obesity agent selected from the group consisting of orlistat, sibutramine, topiramate, axokine, dexamphetamine, phentermine, phenylpropanolamine and mazindol.

9. The method as defined in claim 3 comprising administering a therapeutically effective amount of a compound of formula I and at least one lipid lowering agent selected from the group consisting of pravastatin, lovastatin, simvastatin, atorvastatin, cerivastatin, fluvastatin, nisvastatin, visastatin, atavastatin, rosuvastatin, fenofibrate, gemfibrozil, clofibrate and avasimibe.

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