IP Library Granted Patent US 8,853,385
Granted Patent B2
US 8,853,385 · App. 12/863,429 · Granted Oct 7, 2014

Combination therapy comprising SGLT inhibitors and DPP4 inhibitors

Inventors: Kiichiro Ueta (Osaka, JP); Kenji Arakawa (Osaka, JP); Yasuaki Matsushita (Osaka, JP)
Assignee: Mitsubishi Tanabe Pharma Corporation
C07H7/04
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Quick Facts
Patent No.
US 8,853,385
App. No.
12/863,429
Granted
Oct 7, 2014
Kind
B2
Abstract

The present invention relates to combination therapy comprising a DPP4 inhibitor and an SGLT inhibitor. The combination of the present invention leads to increase plasma GLP-1 level and the combination is useful for prevention or treatment of conditions such as diabetes and diseases related to diabetes.

Claims (42)

1. A method for increasing plasma active GLP-1 level comprising administering to a patient a therapeutically effective amount of an SGLT inhibitor and a DPP4 inhibitor, wherein the SGLT inhibitor is a compound selected from the group consisting of:

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof;

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof;

3-(4-Cyclopropylphenylmethyl)-4-fluoro-1-(β-D-glucopyranosyl)indole or a pharmaceutically acceptable salt thereof; and

3-(4 Cyclopropylphenylmethyl)-4,6-difluoro-1-(β-D-glucopyranosyl)indole or a pharmaceutically acceptable salt thereof and;

the DPP4 inhibitor is a compound selected from the group consisting of:

3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl]piperazin-1-yl]pyrrolidin-2-ylcarbonyl)thiazolidine or a pharmaceutically acceptable salt thereof;

Sitagliptin or a pharmaceutically acceptable salt thereof; and

(2S)-2-cyano-1-[trans-4-(dimethylaminocarbonyl)cyclohexylamino]acetylpyrrolidine or a pharmaceutically acceptable salt thereof.

2. A method for treating a disease which is associated with plasma active GLP-1 level comprising administering to a patient in need thereof a therapeutically effective amount of an SGLT inhibitor and a DPP4 inhibitor, wherein the SGLT inhibitor is a compound selected from the group consisting of:

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof;

3-(5-(4-Fluorophenyl)-2-thienylmethyl)-1-(β-D-glucopyranosyl)-4-methylbenzene or a pharmaceutically acceptable salt thereof;

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3 pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof;

3-(4-Cyclopropylphenylmethyl)-4-fluoro-1-(β-D-glucopyranosyl)indole or a pharmaceutically acceptable salt thereof; and

3-(4-Cyclopropylphenylmethyl)-4,6-difluoro-1-(β-D-glucopyranosyl)indole or a pharmaceutically acceptable salt thereof; and

the DPP4 inhibitor is a compound selected from the group consisting of:

3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine or a pharmaceutically acceptable salt thereof;

Sitagliptin or a pharmaceutically acceptable salt thereof; and

(2S)-2-cyano-1-[trans-4-(dimethylaminocarbonyl)cyclohexylamino]acetylpyrrolidine or a pharmaceutically acceptable salt thereof; and wherein the disease which is associated with plasma active GLP-1 level is selected from the group consisting of diabetes, a condition related to diabetes, myocardial infarction, stroke and a neurodegenerative disorder, and wherein the condition related to diabetes is selected from the group consisting of hyperglycemia, impaired glucose tolerance, impaired fasting glucose, insulin resistance, pancreatic beta-cell insufficiency, enteroendocrine cell insufficiency, glucosuria, metabolic acidosis, cataracts, diabetic nephropathy, diabetic neuropathy, diabetic retinopathy, diabetic coronary artery disease, diabetic cerebrovascular disease, diabetic peripheral vascular disease, metabolic syndrome, hyperlipidemia, atherosclerosis, hypertension, and obesity.

3. A method according to claim 2 , wherein the disease associated with plasma active GLP-1 level is a neurodegenerative disorder, which is selected from excitotoxic brain damage caused by severe epileptic seizures, Alzheimer's disease, Parkinson's disease, Huntington's disease, prion-associated disease, motor-neuron disease, traumatic brain injury, spinal cord injury, and peripheral neuropathy.

4. The method according to claim 1 or 2 , wherein the SGLT inhibitor is 3-(5-(4-fluorophenyl)-2-thienylmethyl)-1-(β-D-glucopyranosyl)-4-methylbenzene or a pharmaceutically acceptable salt thereof; and the DPP4 inhibitor is 3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine or a pharmaceutically acceptable salt thereof.

5. The method according to claim 1 or 2 , wherein the SGLT inhibitor is 3-(5-(4-fluorophenyl)-2-thienylmethyl)-1-(β-D-glucopyranosyl)-4-methylbenzene or a pharmaceutically acceptable salt thereof; and the DPP4 inhibitor is Sitagliptin or a pharmaceutically acceptable salt thereof.

6. A pharmaceutical composition comprising an SGLT inhibitor, a DPP4 inhibitor and a pharmaceutically acceptable carrier or diluent, wherein the SGLT inhibitor and the DPP4 inhibitor are in amounts sufficient to increase plasma active GLP-1 level in a patient, wherein the SGLT inhibitor is a compound selected from the group consisting of:

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof;

3-(5-(4-Fluorophenyl)-2-thienylmethyl)-1-(β-D-glucopyranosyl)-4-methylbenzene or a pharmaceutically acceptable salt thereof;

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof;

3-(4-Cyclopropylphenylmethyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof; and

3-(4-Cyclopropylphenylmethyl)-4,6-difluoro-1-(β-D-glucopyranosyl)indole or a pharmaceutically acceptable salt thereof; and

the DPP4 inhibitor is a compound selected from the group consisting of:

3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine or a pharmaceutically acceptable salt thereof;

Sitagliptin or a pharmaceutically acceptable salt thereof; and

(2S)-2-cyano-1-[trans-4-(dimethylaminocarbonyl)cyclohexylamino]acetylpyrrolidine or a pharmaceutically acceptable salt thereof.

7. A product comprising an SGLT inhibitor and a DPP4 inhibitor as a combined preparation for simultaneous, separate or sequential administration for treating a disease associated with plasma active GLP-1 level, wherein the SGLT inhibitor is a compound selected from the group consisting of:

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]-benzene or a pharmaceutically acceptable salt thereof;

3-(5-(4-Fluorphenyl-2-thienylmethyl)-1-(β-D-glucopyranosyl)-4-methylbenzene or a pharmaceutically acceptable salt thereof;

1-(β-D-Glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof;

3-(4-Cyclopropylphenylmethyl)-4-fluoro-1-(β-D-glucopyranosyl)indole or a pharmaceutically acceptable salt thereof; and

3-(4-Cyclopropylphenylmethyl-4,6-difluoro-1-(β-D-glucopyranosyl)indole or a pharmaceutically acceptable salt thereof; and

the DPP4 inhibitor is a compound selected from the group consisting of:

3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine or a pharmaceutically acceptable salt thereof;

Sitagliptin or a pharmaceutically acceptable salt thereof; and

(2S)-2-cyano-1-[trans-4-(dimethylaminocarbonyl)cyclohexylamino]acetylpyrrolidine or a pharmaceutically acceptable salt thereof; and wherein the disease which is associated with plasma active GLP-1 level is selected from the group consisting of diabetes, a condition related to diabetes, myocardial infarction, stroke and a neurodegenerative disorder, and wherein the condition related to diabetes is selected from the group consisting of hyperglycemia, impaired glucose tolerance, impaired fasting glucose, insulin resistance, pancreatic beta-cell insufficiency, enteroendocrine cell insufficiency, glucosuria, metabolic acidosis, cataracts, diabetic nephropathy, diabetic neuropathy, diabetic retinopathy, diabetic coronary artery disease, diabetic cerebrovascular disease, diabetic peripheral vascular disease, metabolic syndrome, hyperlipidemia, atherosclerosis, hypertension, and obesity.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE ADDRESS OF THE ASSIGNEE PREVIOUSLY RECORDED ON REEL 037163 FRAME 0836. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECT ADDRESS. Recorded Dec 21, 2015
From: MITSUBISHI TANABE PHARMA CORPORATION
To: MITSUBISHI TANABE PHARMA CORPORATION
Reel/Frame 037354/0943 →
CHANGE OF ADDRESS Recorded Nov 30, 2015
From: MITSUBISHI TANABE PHARMA CORPORATION
To: MITSUBISHI TANABE PHARMA CORPORATION
Reel/Frame 037163/0836 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2010
From: UETA, KIICHIRO; ARAKAWA, KENJI; MATSUSHITA, YASUAKI
To: MITSUBISHI TANABE PHARMA CORPORATION
Reel/Frame 024735/0120 →
Continuity (2)
Provisional Application 61021777 · Jan 17, 2008
Related Publication 20110059912A1 · Mar 10, 2011