IP Library Granted Patent US 6,960,591
Granted Patent B2
US 6,960,591 · App. 10/311,688 · Granted Nov 1, 2005

Propane-1,3-dione derivative

Assignee: Yamanouchi Pharmaceutical Co., Ltd.
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Quick Facts
Patent No.
US 6,960,591
App. No.
10/311,688
Granted
Nov 1, 2005
Kind
B2
Abstract

Provided is a pharmaceutical composition containing a propane-1,3-dione derivative as the active ingredient, particularly a GnRH receptor antagonist. Also, provided is a propane-1,3-dione derivative having a GnRH antagonistic effect.

Claims (11)

1. A pharmaceutical composition comprising a propane-1,3-dione compound represented by the general formula (I):

(R 1 , R 2 , R 3 and R 4 : the same or different, H, NO 2 , CN, Halo, a hydrocarbon group which may be substituted, a heterocycle which may be substituted, a hydroxy which may be substituted, a carboxy which may be substituted, an acyl-O— which may be substituted, an acyl which may be substituted, a substituent —S(O)n 101 -(n 101 : an integer of 0 to 2, the same shall apply hereinafter), H—S(O)n 101 -, a carbamoyl which may be substituted, a sulfamoyl which may be substituted, or an amino which may be substituted, and two adjacent groups selected from the group of R 1 , R 2 , R 3 and R 4 may be combined to form an aryl or a cycloalkenyl; R 5 and R 6 : the same or different, H, Halo, a hydrocarbon group which may be substituted or an amino which may be substituted; X 1 and X 2 : the same or different, N, S or O atom; A and B: the same or different, an aryl which may be substituted or a heterocycle which may be substituted; Z 1 , Z 2 , Z 3 and Z 4 : C or N; provided that 1) when X 1 and X 2 each is S or O, one or both of the corresponding R 5 and R 6 are absent; 2) when one to four of Z 1 , Z 2 , Z 3 and/or Z 4 are N, the corresponding R 1 , R 2 , R 3 and/or R 4 are absent) or a pharmaceutically acceptable salt thereof as the active ingredient, and a pharmaceutically acceptable carrier.

2. The pharmaceutical composition comprising a propane-1,3-dione compound or a pharmaceutically acceptable salt thereof as the active ingredient according to claim 1 , wherein at least any one of X 1 and X 2 is N.

3. A method for treating sex hormone-dependent diseases comprising administering to a subject an effective amount of a propane-1,3-dione compound represented by the general formula (I), or a pharmaceutically acceptable salt thereof:

(R 1 , R 2 , R 3 and R 4 : the same or different, H, NO 2 , CN, Halo, a hydrocarbon group which may be substituted, a heterocycle which may be substituted, a hydroxy which may be substituted, a carboxy which may be substituted, an acyl-O— which may be substituted, an acyl which may be substituted, a substituent —S(O)n 101 -(n 101 : an integer of 0 to 2, the same shall apply hereinafter), H—S(O)n 101 -, a carbamoyl which may be substituted, a sulfamoyl which may be substituted, or an amino which may be substituted, and two adjacent groups selected from the group of R 1 , R 2 , R 3 and R 4 may be combined to form an aryl or a cycloalkenyl; R 5 and R 6 : the same or different, H, Halo, a hydrocarbon group which may be substituted or an amino which may be substituted; X 1 and X 2 : the same or different, N, S or O atom; A and B: the same or different, an aryl which may be substituted or a heterocycle which may be substituted; Z 1 , Z 2 , Z 3 and Z 4 : C or N; provided that 1) when X 1 and X 2 each is S or O, one or both of the corresponding R 5 and R 6 are absent; 2) when one to four of Z 1 , Z 2 , Z 3 and/or Z 4 are N, the corresponding R 1 , R 2 , R 3 and/or R 4 are absent), wherein the sex hormone-dependent disease is prostate cancer.

4. A method for treating sex hormone-dependent diseases comprising administering to a subject an effective amount of a propane-1,3-dione compound represented by the general formula (I), or a pharmaceutically acceptable salt thereof:

(R 1 , R 2 , R 3 and R 4 : the same or different, H, NO 2 , CN, Halo, a hydrocarbon group which may be substituted, a heterocycle which may be substituted, a hydroxy which may be substituted, a carboxy which may be substituted, an acyl-O— which may be substituted, an acyl which may be substituted, a substituent —S(O)n 101 -(n 101 : an integer of 0 to 2, the same shall apply hereinafter), H—S(O)n 101 -, a carbamoyl which may be substituted, a sulfamoyl which may be substituted, or an amino which may be substituted, and two adjacent groups selected from the group of R 1 , R 2 , R 3 and R 4 may be combined to form an aryl or a cycloalkenyl; R 5 and R 6 : the same or different, H, Halo, a hydrocarbon group which may be substituted or an amino which may be substituted; X 1 and X 2 : the same or different, N, S or O atom; A and B: the same or different, an aryl which may be substituted or a heterocycle which may be substituted; Z 1 , Z 2 , Z 3 and Z 4 : C or N; provided that 1) when X 1 and X 2 each is S or O, one or both of the corresponding R 5 and R 6 are absent; 2) when one to four of Z 1 , Z 2 , Z 3 and/or Z 4 are N, the corresponding R 1 , R 2 , R 3 and/or R 4 are absent), wherein the sex hormone-dependent disease is breast cancer.

5. A method for treating sex hormone-dependent diseases comprising administering to a subject an effective amount of a propane-1,3-dione compound represented by the general formula (I), or a pharmaceutically acceptable salt thereof:

(R 1 , R 2 , R 3 and R 4 : the same or different, H, NO 2 , CN, Halo, a hydrocarbon group which may be substituted, a heterocycle which may be substituted, a hydroxy which may be substituted, a carboxy which may be substituted, an acyl-O— which may be substituted, an acyl which may be substituted, a substituent —S(O)n 101 -(n 101 : an integer of 0 to 2, the same shall apply hereinafter), H—S(O)n 101 -, a carbamoyl which may be substituted, a sulfamoyl which may be substituted, or an amino which may be substituted, and two adjacent groups selected from the group of R 1 , R 2 , R 3 and R 4 may be combined to form an aryl or a cycloalkenyl; R 5 and R 6 : the same or different, H, Halo, a hydrocarbon group which may be substituted or an amino which may be substituted; X 1 and X 2 : the same or different, N, S or O atom; A and B: the same or different, an aryl which may be substituted or a heterocycle which may be substituted; Z 1 , Z 2 , Z 3 and Z 4 : C or N; provided that 1) when X 1 and X 2 each is S or O, one or both of the corresponding R 5 and R 6 are absent; 2) when one to four of Z 1 , Z 2 , Z 3 and/or Z 4 are N, the corresponding R 1 , R 2 , R 3 and/or R 4 are absent), wherein the sex hormone-dependent disease is endometriosis.

6. A method for treating sex hormone-dependent diseases comprising administering to a subject an effective amount of a propane-1,3-dione compound represented by the general formula (I), or a pharmaceutically acceptable salt thereof:

(R 1 , R 2 , R 3 and R 4 : the same or different, H, NO 2 , CN, Halo, a hydrocarbon group which may be substituted, a heterocycle which may be substituted, a hydroxy which may be substituted, a carboxy which may be substituted, an acyl-O— which may be substituted, an acyl which may be substituted, a substituent —S(O)n 101 -(n 101 : an integer of 0 to 2, the same shall apply hereinafter), H—S(O)n 101 -, a carbamoyl which may be substituted, a sulfamoyl which may be substituted, or an amino which may be substituted, and two adjacent groups selected from the group of R 1 , R 2 , R 3 and R 4 may be combined to form an aryl or a cycloalkenyl; R 5 and R 6 : the same or different, H, Halo, a hydrocarbon group which may be substituted or an amino which may be substituted; X 1 and X 2 : the same or different, N, S or O atom; A and B: the same or different, an aryl which may be substituted or a heterocycle which maybe substituted; Z 1 , Z 2 , Z 3 and Z 4 : C or N; provided that 1) when X 1 and X 2 each is S or O, one or both of the corresponding R 5 and R 6 are absent; 2) when one to four of Z 1 , Z 2 , Z 3 and/or Z 4 are N, the corresponding R 1 , R 2 , R 3 and/or R 4 are absent), wherein the sex hormone-dependent disease is uterine leiomyoma.

Assignments (2)
MERGER Recorded Sep 22, 2005
From: YAMANOUCHI PHARMACEUTICAL CO., LTD.
To: ASTELLAS PHARMA INC.
Reel/Frame 016570/0324 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2002
From: HIRANO, MASAAKI; KAWAMINAMI, EIJI; TOYOSHIMA, AKIRA; MORITOMO, HIROYUKI; SEKI, NORIO; WAKAYAMA, RYUTARO; OKADA, MINORU; KUSAYAMA, TOSHIYUKI
To: YAMANOUCHI PHARMACEUTICAL CO., LTD.
Reel/Frame 013719/0673 →
Priority Claims (2)
JP 2000-204425 · Jul 5, 2000 · national
JP 2001-153372 · May 23, 2001 · national
Continuity (1)
Related Publication 20030191164A1 · Oct 9, 2003