Piperidinylamino-thieno[2,3-D] Pyrimidine Compounds

1 . A compound having the formula

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 and/or ester thereof.

2 . A compound having the formula

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 and/or ester thereof.

3 . A pharmaceutically acceptable salt of the compound of claim 1 which is a maleate, hydrochloride or fumarate salt.

4 . A method of treating pulmonary hypertension, comprising administering to a patient in need thereof the compound of claim 1 .

5 . A method of treating erectile dysfunction, comprising administering to a patient in need thereof the compound of claim 1 .

6 . A method of treating systemic hypertension, comprising administering to a patient in need thereof the compound of claim 1 .

7 . A method of treating a disease state that is alleviated by treatment with a 5-HT 2B antagonist, 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 disease state, 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 and/or ester thereof; and

wherein 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 and/or ester thereof.

8 . The method of claim 7 , wherein the disease state is selected from the diseases pulmonary arterial hypertension, CHF, migraine, hypertension, disorders of the gastrointestinal tract, restenosis, asthma, obstructive airway disease, prostatic hyperplasia, erectile dysfunction and priapism.

9 . The method of claim 7 , wherein the disease state comprises inflammatory pain, neuropathic pain, cancer pain, acute pain or chronic pain.

10 . The method of claim 7 , wherein the disease state comprises allergic asthma, irritable bowel syndrome, hypertonic lower esophageal sphincter, motility disorders or benign prostatic hyperplasia.

11 . The method of claim 7 , wherein the disease state comprises depression, anxiety, attention deficit hyperactivity disorder, obesity, sleeping disorder, Alzheimer's disease, or Parkinson disease.

12 . The method of claim 7 , wherein the disease state comprises carcinoid tumors or teratocarcinoma.

13 . The method of claim 7 , wherein the disease state comprises hyperprolactinemia or acromegaly.

14 . A pharmaceutically acceptable salt of the compound of claim 2 which is a maleate, hydrochloride or fumarate salt.

15 . A method of treating pulmonary hypertension, comprising administering to a patient in need thereof the compound of claim 2 .

16 . A method of treating erectile dysfunction, comprising administering to a patient in need thereof the compound of claim 2 .

17 . A method of treating systemic hypertension, comprising administering to a patient in need thereof the compound of claim 2 .