Piperidinylamino-thieno[2,3-D] pyrimidine compounds

1. A method of treating pulmonary hypertension, comprising administering to a patient in need thereof a composition comprising a compound of formula II or III; wherein formula II is represented by

wherein

R 1 is selected from the group consisting of halo, lower alkyl, cyano, and trihalomethyl;

each R 2 is independently hydrogen, halo, cyano, trihalomethyl, lower alkoxy, carboxylate, an amide, or a sulfonyl group; and

n is 1 or 2, provided that when n is 1, R 2 is not hydrogen, and when n is 2, both R 2 groups are not hydrogen;

or a pharmaceutically acceptable salt thereof; and

formula III is represented by

wherein

X is halo;

R 3 is hydrogen, halo, cyano, or trihalomethyl; and

n is 1 or 2, provided that when n is 1, R 3 is not hydrogen, and when n is 2, both R 3 groups are not hydrogen;

or a pharmaceutically acceptable salt thereof.

2. A method of treating systemic hypertension, comprising administering to a patient in need thereof a composition comprising a compound of formula II or III; wherein formula II is represented by

wherein

R 1 is selected from the group consisting of halo, lower alkyl, cyano, and trihalomethyl;

each R 2 is independently hydrogen, halo, cyano, trihalomethyl, lower alkoxy, carboxylate, an amide, or a sulfonyl group; and

n is 1 or 2, provided that when n is 1, R 2 is not hydrogen, and when n is 2, both R 2 groups are not hydrogen;

or a pharmaceutically acceptable salt thereof; and

formula III is represented by

wherein

X is halo;

R 3 is hydrogen, halo, cyano, or trihalomethyl; and

n is 1 or 2, provided that when n is 1, R 3 is not hydrogen, and when n is 2, both R 3 groups are not hydrogen;

or a pharmaceutically acceptable salt thereof.

3. A method of treating a disorder selected from the group consisting of migraine and pulmonary arterial hypertension, comprising administering to a patient in need thereof a composition comprising a compound of formula II or III or its salt in an amount effective to treat the disorder; wherein formula II is represented by

wherein

R 1 is selected from the group consisting of halo, lower alkyl, cyano, and trihalomethyl;

each R 2 is independently hydrogen, halo, cyano, trihalomethyl, lower alkoxy, carboxylate, an amide, or a sulfonyl group; and

n is 1 or 2, provided that when n is 1, R 2 is not hydrogen, and when n is 2, both R 2 groups are not hydrogen;

or a pharmaceutically acceptable salt thereof; and

formula III is represented by

wherein

X is halo;

R 3 is hydrogen, halo, cyano, or trihalomethyl; and

n is 1 or 2, provided that when n is 1, R 3 is not hydrogen, and when n is 2, both R 3 groups are not hydrogen;

or a pharmaceutically acceptable salt thereof.

4. The method of claim 3 , wherein the disorder is pulmonary arterial hypertension.

5. The method of claim 3 , wherein the disorder is migraine.

6. The method of claim 1 , wherein the composition comprises a compound of formula III.

7. The method of claim 2 , wherein the composition comprises a compound of formula III.

8. The method of claim 3 , wherein the composition comprises a compound of formula III.

9. A method of treating pulmonary arterial hypertension, comprising administering to a patient in need thereof a composition comprising 5-((4-(6-chlorothieno[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)methyl)-2-fluorobenzonitrile or a pharmaceutically acceptable salt thereof.

10. The method of claim 4 , wherein the composition comprises a compound of formula III.

11. The method of claim 10 , wherein R 3 is halo or cyano.

12. The method of claim 5 , wherein the composition comprises a compound of formula III.

13. The method of claim 12 , wherein R 3 is halo or cyano.

14. The method of claim 5 , wherein said compound of formula III is 5-((4-(6-chlorothieno[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)methyl)-2-fluorobenzonitrile or a pharmaceutically acceptable salt thereof.

15. The method of claim 7 , wherein R 3 is halo or cyano.

16. The method of claim 7 , wherein said compound of formula III is 5-((4-(6-chlorothieno[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)methyl)-2-fluorobenzonitrile or a pharmaceutically acceptable salt thereof.