IP Library Granted Patent US 7,064,204
Granted Patent B2
US 7,064,204 · App. 10/452,788 · Granted Jun 20, 2006

Pharmaceutically active compounds having a tricyclic pyrazolotriazolopyrimidine ring structure and methods of use

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Quick Facts
Patent No.
US 7,064,204
App. No.
10/452,788
Granted
Jun 20, 2006
Kind
B2
Abstract

New compounds having a tricyclic pyrazolotriazolopyrimidine ring structure are provided and methods of using those compounds for a variety of therapeutic indications.

Claims (32)

1. A compound of any one of the following Formula IX or X:

wherein:

R 1 is selected from the group consisting of hydrogen, C 1-6 alkylamino, di(C 1-6 ) alkylamino, and C 1-6 alkylthio;

R 2 is selected from optionally substituted C 1-6 alkyl and optionally substituted C 7-12 aralkyl;

R 3 is selected from the group consisting of optionally substituted a C 1-6 alkyl, optionally substituted C 7-12 aralkyl, and optionally substituted C 2-6 alkanoyl;

E is O or N—C 1-6 alkyl; and pharmaceutically acceptable salt thereof.

2. A compound that is:

4-(5-Amino-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-phenol;

2-(4-Chloro-phenyl)-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine;

2-(4-Ethoxy-phenyl)-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine; [4-(5-Amino-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-phenoxy]-acetic acid ethyl ester;

[4-(5-Amino-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-phenoxy]-acetic acid;

2-[4-(5-Amino-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-phenoxy]-N-(4-iodo-phenyl)-acetamide;

N9-Ethyl-2-furan-2-yl-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5,9-diamine;

N9-Ethyl-2-furan-2-yl-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5,9-diamine hydrochloride salt;

2-Furan-2-yl-N-9-(4-methoxy-phenyl)-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5,9-diamine;

2-Furan-2-yl-8-methyl-9-(4-methyl-piperazin-1-yl)-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine;

2-Furan-2-yl-8-methyl-9-(4-methyl-piperazin-1-yl)-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine dihydrochloride salt;

2-Furan-2-yl-8-methyl-9-methylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine;

2-Furan-2-yl-8-methyl-9-propylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine;

2-Furan-2-yl-9-methylsulfanyl-8-(3-phenyl-propyl)-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine;

1-(9-Ethylamino-2-furan-2-yl-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-3-(4-methoxy-phenyl)-urea;

1-(9-Ethylamino-2-furan-2-yl-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-3-(4-methoxy-phenyl)-urea hydrochloride salt;

1-[2-Furan-2-yl-8-methyl-9-(4-methyl-piperazin-1-yl)-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyimidin-5-yl]-3-(4-methoxy-phenyl)-urea;

1-(2-Furan-2-yl-8-methyl-9-methylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-3-(4-methoxy-phenyl)-urea;

N-(2-Furan-2-yl-8-methyl-9-methylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-2-(4-methoxy-phenyl)-acetamide;

N-(2-Furan-2-yl-8-methyl-9-methylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-2-(4-isobutyl-phenyl)-acetamide;

2-Benzo[1,3]dioxol-5-yl-N-(2-furan-2-yl-8-methyl-9-methylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-acetamide;

2-Benzo[1,3]dioxol-5-yl-N-(9-ethylamino-2-furan-2-yl-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-acetamide;

4-(5-Amino-2-furan-2-yl-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-9-ylamino)-phenol;

8-Methyl-2-[5-(4-methyl-piperazin-1-ylmethyl)-furan-2-yl]-9-methylsulfanyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine;

8-Methyl-9-methylsulfanyl-2-(5-morpholin-4-ylmethyl-furan-2-yl)-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine; or a pharmaceutically acceptable salt thereof.

3. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and one or more compounds of any one of claims 1 or 2 .

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Feb 3, 2011
From: CREDIT SUISSE AG
To: KING PHARMACEUTICALS RESEARCH AND DEVELOPMENT, INC.
Reel/Frame 025738/0132 →
SECURITY AGREEMENT Recorded May 13, 2010
From: KING PHARMACEUTICALS RESEARCH AND DEVELOPMENT, INC.
To: CREDIT SUISSE AG
Reel/Frame 025703/0628 →
RELEASE OF SECURITY INTEREST Recorded May 11, 2010
From: KING PHARMACEUTICALS RESEARCH AND DEVELOPMENT, INC.
To: CREDIT SUISSE AG
Reel/Frame 024369/0022 →
SECURITY AGREEMENT Recorded Dec 30, 2008
From: KING PHARMACEUTICALS RESEARCH & DEVELOPMENT, INC.
To: CREDIT SUISSE, AS AGENT
Reel/Frame 022034/0870 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 26, 2003
From: BARALDI, PIER GIOVANNI; BOREA, PIER ANDREA
To: KING PHARMACEUTICALS RESEARCH & DEVELOPMENT, INC.
Reel/Frame 014520/0342 →