IP Library Granted Patent US 6,939,887
Granted Patent B2
US 6,939,887 · App. 10/470,813 · Granted Sep 6, 2005

Benzimidazolidinone derivatives

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Quick Facts
Patent No.
US 6,939,887
App. No.
10/470,813
Granted
Sep 6, 2005
Kind
B2
Abstract

The present invention can provide novel compounds useful as orally administrable growth hormone releaser, more specifically a benzimidazolidinone derivative of formula (1) or a pharmaceutically acceptable salt thereof: (1) wherein R 1 is optionally substituted alkyl or the like; R 2 , R 3 and R 4 are each hydrogen, optionally substituted alkyl, or the like; R 5 is optionally substituted aryl; q is 0 or 1; and W 1 is a group represented by formula (2): (2) n is 1, 2 or 3; m is 0, 1, 2 or 3; R 6 and R 7 are each hydrogen, optionally substituted alkyl, or the like; and R 8 and R 9 are each hydrogen, optionally substituted alkyl, or the like.

Claims (26)

1. A benzimidazolidinone derivative of formula (1) or a pharmaceutically acceptable salt thereof:

wherein

R 1 is optionally substituted C 1 -C 3 alkyl, optionally substituted C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, hydroxy, cyano, halogen or nitro;

R 2 is hydrogen, optionally substituted C 1 -C 3 alkyl, optionally substituted C 1 -C 3 alkoxy, hydroxy, cyano or halogen;

R 3 is optionally substituted C 1 -C 6 alkyl, optionally substituted C 3 -C 7 alkynyl, optionally substituted C 1 -C 6 alkoxy, carbamoyl, amino, hydroxy, cyano, nitro or halogen;

R 4 is hydrogen, hydroxy, cyano, fluorine or chlorine;

q is 0 or 1;

R 5 is optionally substituted aryl;

W 1 is a group represented by formula (2):

wherein

n is 1, 2 or 3; m is 0, 1, 2 or 3;

R 6 and R 7 are each independently hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl; or R 6 and R 7 are taken together to form optionally substituted saturated heterocyclic ring containing nitrogen(s);

R 8 and R 9 are each independently hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl; or R 8 and R 9 are taken together to form optionally substituted cycloalkane or optionally substituted saturated heterocyclic ring;

or R 6 and R 8 are taken together to form optionally substituted saturated heterocyclic ring containing nitrogen(s); or R 7 and R 9 are taken together to form optionally substituted saturated heterocyclic ring containing nitrogen(s).

2. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to claim 1 wherein R 1 is optionally substituted C 1 -C 3 alkyl.

3. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to claim 1 wherein R 1 is C 1 -C 3 alkyl substituted by halogen(s).

4. A pharmaceutical composition comprising the benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to claim 1 and an inactive carrier.

5. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to claim 1 , wherein q=0.

6. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to any of claims 1 - 3 and 5 , wherein both of R 2 and R 4 are hydrogen.

7. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to any of claims 1 - 3 and 5 , wherein R 3 is optionally substituted C 3 -C 7 alkynyl or carbamoyl.

8. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to any of claims 1 - 3 and 5 , wherein R 5 is optionally substituted phenyl, optionally substituted 1-naphthyl, or optionally substituted 2-naphthyl.

9. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to claim 8 , wherein R 5 is phenyl substituted by alkyl(s), halogen(s), trifluoromethyl(s), or alkoxy(s).

10. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to any of claims 1 - 3 and 5 , wherein R 6 and R 7 are each independently optionally substituted alkyl or optionally substituted cycloalkyl; or R 6 and R 7 are taken together to form optionally substituted saturated heterocyclic ring containing nitrogen(s).

11. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to any of claims 1 - 3 and 5 , wherein W 1 is a group represented by formula (3):

wherein p is 2, 3, or 4; R 10 and R 11 are each independently optionally substituted alkyl.

12. The benzimidazolidinone derivative or a pharmaceutically acceptable salt thereof according to claim 11 , wherein R 10 and R 11 are each independently methyl or ethyl.

Assignments (2)
MERGER/NAME CHANGE Recorded Nov 11, 2005
From: SUMITOMO PHARMACEUTICALS CO., LTD.
To: DAINIPPON SUMITOMO PHARMA CO., LTD.
Reel/Frame 016770/0431 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 21, 2003
From: OKAZAKI, KAZUHIKO; UEKI, YASUYUKI
To: SUMITOMO PHARMACEUTICALS CO., LTD.
Reel/Frame 014407/0877 →