# US 9,006,273 B2 · N-hetero-ring-substituted amide derivative

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- Number: US 9,006,273 B2
- Document ID: US9006273B2
- Status: Granted
- Kind: B2
- Application number: 14/235,331
- Filed: 2012-07-27
- Published: 2014-08-07
- Granted: 2015-04-14
- Earliest claimed: 2011-07-29
- Assignees: Daiichi Sankyo Company, Limited
- Applicants: Shigeo Yamanoi; Madoka Hatta; Hidenori Namiki; Koji Matsumoto; Tomomi Yoshitomi
- Inventors: Shigeo Yamanoi; Madoka Hatta; Hidenori Namiki; Koji Matsumoto; Tomomi Yoshitomi
- Web page: https://patentgrep.com/patent/US9006273B2

## CPC

- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A61P 1/18: for pancreatic disorders, e.g. pancreatic enzymes
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/48: of the pancreatic hormones
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds having an excellent hypoglycemic effect and β cell- or pancreas-preserving effects or pharmaceutically acceptable salts thereof, and a pharmaceutical composition having an excellent therapeutic effect and/or prophylactic effect on type 1 diabetes, type 2 diabetes, and the like, which cause hyperglycemia due to abnormal glucose metabolism. A compound represented by general formula (I), or a pharmaceutically acceptable salt thereof, is disclosed.

## Claims

### Claim 1

A compound represented by general formula (I):
wherein
R1 represents
* represents the point of attachment to the nitrogen atom, and
R2 represents a methyl group or an ethyl group;
or a pharmaceutically acceptable salt thereof.

### Claim 2

A compound selected from the group consisting of the following compounds:
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro -N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}1,2,4-oxadiazol-3-yl)-2-fluoro -N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]ethyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4 -(cyclopropylcarbonyl)phenoxy]ethyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R)-2-oxotetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S)-2-oxotetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}- 1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S)-5-oxotetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}- 1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R)-2-oxopyrrolidin-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}- 1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S)-2-oxopyrrolidin-3-yl]benzamide;
4-(5-{(1R)-1[4-(cyclopropylcarbonyl)phenoxy]propyl}--1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4S)-4-hydroxy-2-oxotetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1[4-(cyclopropylcarbonyl)phenoxy]ethyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-[(3R)-2-oxopyrrolidin-3-yl]benzamide;
4-(5-{(1R)-1[4-(cyclopropylcarbonyl)phenoxy]ethyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S)-2-oxopyrrolidin-3-yl]benzamide;
4-(5-{(1R)-1[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxy-2-oxotetrahydrofuran-3-yl]benzamide;
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]ethyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide; and
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxyl]ethyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4S)-4-hydroxytetrahydrofuran-3 -yl]benzamide;
or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

A pharmaceutical composition comprising an excipient and, as an active ingredient, a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

A method for treating type 1diabetes, type 2 diabetes, or obesity, the method comprising administering to a mammal a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 4)

A method according to claim 4, wherein the mammal is a human being.

### Claim 6 (depends on 4)

A method according to claim 4, wherein the disease is type 1 diabetes.

### Claim 7 (depends on 2)

A method for treating type 1 diabetes, type 2 diabetes, or obesity, the method comprising administering to a mammal a compound according to claim 2 or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 7)

A method according to claim 7, wherein the mammal is a human being.

### Claim 9 (depends on 7)

A method according to claim 7, wherein the disease is type 1 diabetes.

### Claim 10 (depends on 1)

A method for protecting β-cell or the pancreas, the method comprising administering to a mammal a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 10)

A method according to claim 10, wherein the mammal is a human being.

### Claim 12 (depends on 2)

A method for protecting β-cell or the pancreas, the method comprising administering to a mammal a compound according to claim 2 or a pharmaceutically acceptable salt thereof.

### Claim 13 (depends on 12)

A method according to claim 12, wherein the mammal is a human being.

### Claim 14 (depends on 2)

A pharmaceutical composition comprising an excipient and, as an active ingredient, a compound according to claim 2 or a pharmaceutically acceptable salt thereof.