# US 7,612,078 B2 · Piperidinylamino-thieno[2,3-D] pyrimidine compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,612,078 B2 - Document ID: US7612078B2 - Status: Granted - Kind: B2 - Application number: 11/075,565 - Filed: 2005-03-08 - Published: 2005-10-06 - Granted: 2009-11-03 - Earliest claimed: 2003-03-31 - Assignees: Epix Delaware, Inc. - Inventors: Dale S. Dhanoa; Oren Becker; Silvia Noiman; A. Sekar Reddy; Srinivasa R. Cheruku; Rosa E. Melendez; Anurag Sharadendu; Dongli Chen; Yael Marantz; Sharon Shacham; Alexander Heifetz; Boaz Inbal; Venkitasamy Kesavan; Shay Bar-Haim - Web page: https://patentgrep.com/patent/US7612078B2 ## CPC - C07D 495/04: Ortho-condensed systems - A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system - A61P 5/00: Drugs for disorders of the endocrine system - A61P 5/02: of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin - A61P 5/08: for decreasing, blocking or antagonising the activity of the anterior pituitary hormones - A61P 9/00: Drugs for disorders of the cardiovascular system - A61P 9/08: Vasodilators for multiple indications - A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis - A61P 9/12: Antihypertensives - A61P 11/00: Drugs for disorders of the respiratory system - A61P 11/06: Antiasthmatics - A61P 11/08: Bronchodilators - A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives - A61P 15/10: for impotence - A61P 19/00: Drugs for skeletal disorders - A61P 25/00: Drugs for disorders of the nervous system - A61P 25/04: Centrally acting analgesics, e.g. opioids - A61P 25/06: Antimigraine agents - A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia - A61P 25/16: Anti-Parkinson drugs - A61P 25/20: Hypnotics; Sedatives - A61P 25/22: Anxiolytics - A61P 25/24: Antidepressants - A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia - A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] - A61P 35/00: Antineoplastic agents - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract The invention relates to 5-HT receptor modulators, particularly 5-HT2B antagonists. Novel piperidinylamino-thieno[2,3-d]pyrimidine compounds represented by Formula I, II and III, and uses thereof for treating conditions including pulmonary arterial hypertension, congestive heart failure, and hypertension. ## Claims ### Claim 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 R1 is selected from the group consisting of halo, lower alkyl, cyano, and trihalomethyl; each R2 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, R2 is not hydrogen, and when n is 2, both R2 groups are not hydrogen; or a pharmaceutically acceptable salt thereof; and formula III is represented by wherein X is halo; R3 is hydrogen, halo, cyano, or trihalomethyl; and n is 1 or 2, provided that when n is 1, R3 is not hydrogen, and when n is 2, both R3 groups are not hydrogen; or a pharmaceutically acceptable salt thereof. ### Claim 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 R1 is selected from the group consisting of halo, lower alkyl, cyano, and trihalomethyl; each R2 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, R2 is not hydrogen, and when n is 2, both R2 groups are not hydrogen; or a pharmaceutically acceptable salt thereof; and formula III is represented by wherein X is halo; R3 is hydrogen, halo, cyano, or trihalomethyl; and n is 1 or 2, provided that when n is 1, R3 is not hydrogen, and when n is 2, both R3 groups are not hydrogen; or a pharmaceutically acceptable salt thereof. ### Claim 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 R1 is selected from the group consisting of halo, lower alkyl, cyano, and trihalomethyl; each R2 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, R2 is not hydrogen, and when n is 2, both R2 groups are not hydrogen; or a pharmaceutically acceptable salt thereof; and formula III is represented by wherein X is halo; R3 is hydrogen, halo, cyano, or trihalomethyl; and n is 1 or 2, provided that when n is 1, R3 is not hydrogen, and when n is 2, both R3 groups are not hydrogen; or a pharmaceutically acceptable salt thereof. ### Claim 4 (depends on 3) The method of claim 3, wherein the disorder is pulmonary arterial hypertension. ### Claim 5 (depends on 3) The method of claim 3, wherein the disorder is migraine. ### Claim 6 (depends on 1) The method of claim 1, wherein the composition comprises a compound of formula III. ### Claim 7 (depends on 2) The method of claim 2, wherein the composition comprises a compound of formula III. ### Claim 8 (depends on 3) The method of claim 3, wherein the composition comprises a compound of formula III. ### Claim 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. ### Claim 10 (depends on 4) The method of claim 4, wherein the composition comprises a compound of formula III. ### Claim 11 (depends on 10) The method of claim 10, wherein R3 is halo or cyano. ### Claim 12 (depends on 5) The method of claim 5, wherein the composition comprises a compound of formula III. ### Claim 13 (depends on 12) The method of claim 12, wherein R3 is halo or cyano. ### Claim 14 (depends on 5) 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. ### Claim 15 (depends on 7) The method of claim 7, wherein R3 is halo or cyano. ### Claim 16 (depends on 7) 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.