IP Library Granted Patent US 7,384,936
Granted Patent B2
US 7,384,936 · App. 10/501,029 · Granted Jun 10, 2008

Carboxamidine derivatives and their use in the treatment of vascular diseases

Assignee: CytRx Corporation
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Quick Facts
Patent No.
US 7,384,936
App. No.
10/501,029
Granted
Jun 10, 2008
Kind
B2
Abstract

The invention relates to carboxamidine derivatives to pharmaceutical compositions containing the same and the use thereof in the preparation of pharmaceutical compositions for the treatment of vascular diseases.

Claims (20)

1. A compound of formula III

wherein R 1 and R 2 are independently hydrogen, straight chained C 1-6 alkyl group optionally substituted with a phenyl group, branched C 1-6 alkyl group optionally substituted with a phenyl group, or R 1 and R 2 together with the nitrogen atom attached thereto form a 5-7 membered saturated heterocyclic ring optionally containing further nitrogen and/or oxygen heteroatoms, wherein said heterocyclic ring is optionally substituted with one or more hydroxy, oxo or benzyl groups;

A is a 5-6 membered N-containing heteroaromatic ring having a N-oxide structure on the nitrogen heteroatom;

n is 0, 1, or 2;

z is 0 or 1;

or a stereoisomer or salt thereof.

2. The compound according to claim 1 , wherein the compound is 5,6-dihydro-5-[(1-piperidinyl)methyl]-3-(1-oxido-3-pyridyl)-4H-1,2,4-oxadiazine, or a stereoisomer and/or salt thereof.

3. The compound according to claim 2 , wherein the compound is (+)-5,6-dihydro-5-[(1-piperidinyl)methyl]-3-(1-oxido-3-pyridyl)-4H-1,2,4-oxadiazine, or a stereoisomer and/or salt thereof.

4. The compound according to claim 1 , wherein the compound is 5,6-dihydro-5-[(1-oxido-1-piperidinyl)methyl]-3-(1-oxido-3-pyridyl)-4H-1,2,4-oxadiazine, or a stereoisomer and/or salt thereof.

5. A pharmaceutical composition comprising a compound of formula III as defined in claim 1 and a pharmaceutically acceptable carrier.

6. A compound of formula III

wherein R 1 and R 2 together with the nitrogen atom attached thereto form a 5-7 membered saturated heterocyclic ring optionally containing further nitrogen and/or oxygen heteroatoms, wherein said heterocyclic ring is substituted with one or more hydroxy, oxo or benzyl groups;

A is a phenyl group optionally substituted with one or more C 1-4 alkyl, C 1-4 haloalkyl, nitro, or halogen, or is a 5-6 membered heteroaromatic ring containing at least one heteroatom selected from nitrogen, oxygen, and sulfur, wherein the nitrogen heteroatom optionally has a N-oxide structure;

n is 0, 1, or 2;

z is 0 or 1;

or a stereoisomer or salt thereof.

7. The compound according to claim 6 , wherein the compound is 5,6-dihydro-5-[(4-benzyl-1-piperidinyl)methyl]-3-(3-pyridyl)-4H-1,2,4-oxadiazine, or a stereoisomer and/or salt thereof.

8. The compound according to claim 6 , wherein the compound is 5,6-dihydro-5-[(2-oxo-1-piperidinyl)methyl]-3-(3-pyridyl)-4H-1,2,4-oxadiazine, or a stereoisomer and/or salt thereof.

9. The compound according to claim 6 , wherein the compound is 5,6-dihydro-5-[(4-hydroxy-1-piperidinyl)methyl]-3-(3-pyridyl)-4H-1,2,4-oxadiazine, or a stereoisomer and/or salt thereof.

10. A pharmaceutical composition comprising a compound of formula III as defined in claim 6 and a pharmaceutically acceptable carrier.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2022
From: ORPHAZYME A/S
To: KEMPHARM, INC.
Reel/Frame 060592/0646 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2022
From: KEMPHARM, INC.
To: KEMPHARM DENMARK A/S
Reel/Frame 060592/0595 →
CHANGE OF NAME Recorded Apr 11, 2018
From: ORPHAZYME APS
To: ORPHAZYME A/S
Reel/Frame 045911/0992 →
PATENT ASSIGNMENT AGREEMENT Recorded Jun 26, 2013
From: CYTRX CORPORATION
To: ORPHAZYME APS
Reel/Frame 030694/0809 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2006
From: BRX MAGYARORSZAG RT
To: CYTRX CORPORATION
Reel/Frame 018590/0620 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2005
From: BIOREX KUTATÓ ÉS FEJLESZTÖ RT. ("V.A."); BRX RESEARCH AND DEVELOPMENT COMPANY LTD
To: CYTRX CORPORATION
Reel/Frame 016460/0725 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2005
From: BIROREX KUTATO ES FEJLESZTO RT.
To: CYTRX CORPORATION
Reel/Frame 016784/0135 →
Priority Claims (2)
HU 0200109 · Jan 11, 2002 · national
HU 0204362 · Dec 17, 2002 · national
Continuity (1)
Related Publication 20060058294A1 · Mar 16, 2006