Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma

Patent metadata

Field	Value
Publication number	US-9802954-B2
Application number	US-201313963513-A
Country	US
Kind code	B2
Filing date	Aug 9, 2013
Priority date	Aug 24, 2011
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

Piperidino-dihydrothienopyrimidine sulfoxides of formula I

wherein:
Ring A is a 6-membered aromatic ring optionally comprising one or two nitrogen atoms and R is Cl and is located in the para-, meta-, or ortho-position of Ring A, S* is a sulphur atom that represents a chiral center,

and all pharmaceutically acceptable salts, enantiomers and racemates, hydrates and solvates thereof and the use of these compounds for the treatment of inflammatory or allergic diseases of the respiratory tract such as COPD or asthma.

First claim

The invention claimed is:

1. A method of treating COPD, asthma or idiopathic pulmonary fibrosis comprising the step of administering to a patient in need thereof an effective amount of a compound of formula I

wherein:
Ring A is a 6-membered aromatic ring optionally comprising one or two nitrogen atoms,
R is Cl and is located in the para-, meta-, or ortho-position of Ring A, and
S* is a sulphur atom that represents a chiral center,
or of a pharmaceutically acceptable salt thereof.

2. The method of claim 1 , wherein R is Cl and is located in the para-position of Ring A.

3. The method of claim 1 , wherein Ring A is phenyl, pyridinyl, or pyrimidinyl.

4. The method of claim 1 , wherein the compound of formula I is

5. The method of claim 1 , wherein the compound of formula I is

6. The method of claim 1 , wherein S* is in the R-configuration.

7. The method of claim 2 , wherein S* is in the R-configuration.

8. The method of claim 4 , wherein S* is in the R-configuration.

9. The method of claim 5 , wherein S* is in the R-configuration.

10. The method of claim 1 , wherein S* is in the S-configuration.

11. The method of claim 2 , wherein S* is in the S-configuration.

12. The method of claim 4 , wherein S* is in the S-configuration.

13. The method of claim 5 , wherein S* is in the S-configuration.

14. The method of claim 5 , wherein the compound of formula I shows a reflex peak in the X-ray powder diffraction diagram with a d-value of 4.62 Å.

15. The method of claim 5 , wherein the compound of formula I shows reflex peaks in the X-ray powder diffraction diagram with d-values of 4.62 Å, 6.82 Å, and 10.09 Å.

16. The method of claim 5 , wherein the compound of formula I shows reflex peaks in the X-ray powder diffraction diagram with d-values of 4.62 Å, 4.17 Å, and 3.66 Å.

17. The method of claim 5 , wherein the compound of formula I shows reflex peaks in the X-ray powder diffraction diagram with d-values of 4.62 Å, 6.82 Å, 10.09 Å, 3.93 Å, and 4.94 Å.

18. The method of claim 5 , wherein the compound of formula I shows reflex peaks in the X-ray powder diffraction diagram with d-values of 4.62 Å, 4.17 Å, 3.66 Å, 3.73 Å, and 18.47 Å.

19. The method of claim 5 , wherein the compound of formula I shows a reflex peak in the X-ray powder diffraction diagram with a d-value of 4.12 Å.

20. The method of claim 5 , wherein the compound of formula I shows reflex peaks in the X-ray powder diffraction diagram with d-values of 4.12 Å, 4.29 Å, and 5.15 Å.

21. The method of claim 5 , wherein the compound of formula I shows reflex peaks in the X-ray powder diffraction diagram with d-values of 4.12 Å, 4.29 Å, 5.15 Å, 3.95 Å, and 3.36 Å.

Assignees

• Boehringer Ingelheim Int

Inventors

• Pouzet Pascale A J
• Nickolaus Peter
• Werthmann Ulrike
• Frutos Rogelio P
• Yang Bing-Shiou
• Kim Soojin
• Mulder Jason Alan
• Patel Nitinchandra D
• Senanayake Chris Hugh
• Tampone Thomas Gabriel
• Wei Xudong

Classifications

• C07D495/04 Primary

  Ortho-condensed systems · CPC title