IP Library Granted Patent US 9,149,479
Granted Patent B2
US 9,149,479 · App. 14/508,077 · Granted Oct 6, 2015

Hydroxy-6-heteroarylphenanthridines and their use as PDE4 inhibitors

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Quick Facts
Patent No.
US 9,149,479
App. No.
14/508,077
Granted
Oct 6, 2015
Kind
B2
Abstract

Compounds of the formula Ia***** in which the substituents have the definitions provided in the specification, are novel, effective PDE4 inhibitors, useful in the treatment of psoriasis.

Claims (34)

1. A method of treating psoriasis in a patient, comprising administering to said patient a compound of formula Ia*****

wherein

R1 is methoxy,

R2 is methoxy, ethoxy, difluoromethoxy or 2,2-difluoroethoxy,

R3 is hydrogen,

R31 is hydrogen,

R41 is hydrogen,

R5 is hydrogen,

Har is substituted by R6 and R7, and is pyridinyl, in which

R6 is oxo, and

R7 is methyl,

or a pharmaceutically acceptable salt thereof.

2. The method of treating psoriasis in a patient according to claim 1 , comprising administering to said patient a compound of formula Ia*****,

wherein

R1 is methoxy,

R2 is methoxy, ethoxy, difluoromethoxy or 2,2-difluoroethoxy,

R3 is hydrogen,

R31 is hydrogen,

R41 is hydrogen,

R5 is hydrogen,

Har is 1-methyl-1H-pyridin-2-one-5-yl,

or a pharmaceutically acceptable salt thereof.

3. The method of treating psoriasis in a patient according to claim 1 , comprising administering to said patient a compound of formula Ia*****,

wherein

R1 is methoxy,

R2 is ethoxy, difluoromethoxy or 2,2-difluoroethoxy,

R3 is hydrogen,

R31 is hydrogen,

R41 is hydrogen,

R5 is hydrogen,

Har is 1-methyl-1H-pyridin-2-one-5-yl,

or a pharmaceutically acceptable salt thereof.

4. The method of treating psoriasis in a patient according to claim 1 , comprising administering to said patient a compound of formula Ia*****, which is selected from the group consisting of 5-((2R,4aR,10bR)-9-Ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-6-yl)-1-methyl-1H-pyridin-2-one and a pharmaceutically acceptable salt thereof.

5. The method of treating psoriasis in a patient according to claim 1 , comprising administering to said patient a compound of formula Ia*****, which is 5-((2R,4aR,10bR)-9-Ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-6-yl)-1-methyl-1H-pyridin-2-one.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2021
From: TAKEDA GMBH
To: TAKEDA PHARMACEUTICAL COMPANY LIMITED
Reel/Frame 058043/0943 →
MERGER Recorded Jan 11, 2019
From: TAKEDA GMBH
To: NYCOMED ASSET MANAGEMENT GMBH
Reel/Frame 049367/0773 →
MERGER Recorded Jan 11, 2019
From: NYCOMED ASSET MANAGEMENT GMBH
To: NYCOMED GERMANY HOLDING GMBH
Reel/Frame 049367/0792 →
CHANGE OF NAME Recorded Jan 11, 2019
From: NYCOMED GERMANY HOLDING GMBH
To: TAKEDA GMBH
Reel/Frame 049367/0832 →
CHANGE OF NAME Recorded Jan 11, 2019
From: ALTANA PHARMA AG
To: NYCOMED GMBH
Reel/Frame 048066/0082 →
CHANGE OF NAME Recorded Jan 11, 2019
From: NYCOMED GMBH
To: TAKEDA GMBH
Reel/Frame 048046/0708 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2018
From: KAUTZ, ULRICH
To: ALTANA PHARMA AG
Reel/Frame 047844/0131 →