Claims
- 1. A compound having the formula
- 2. The compound of claim 1, wherein said resulting aryl, pyridinyl, pyrimidinyl or pyrazinyl group is substituted with a substituent selected from the group consisting of lower alkyl; cycloalkyl; trihalomethyl; halo; a conjugated five- or six-membered cyclic or heterocyclic ring; nitro; NHCO-alkyl; NCO-dialkyl; sulfonamidoalkyl; hydroxyl; and cyano.
- 3. The compound of claim 2, wherein both Z atoms are C; R2 is nitro, NHCO-alkyl, NCO-dialkyl, or aminoalkyl; and R3 is H.
- 4. The compound of claim 3, wherein said NHCO-alkyl is NHCO-lower alkyl.
- 5. The compound of claim 4, wherein said NHCO-lower alkyl is NHCO—(CH3), NHCO—(CH2CH3), NHCO—(CH2CH2—CH3), or NHCO—(CH(CH2)2.
- 6. The compound of claim 3, wherein R2 is in the meta position.
- 7. The compound of claim 1, wherein said lower alkyl or alkoxy is lower (C1-C4).
- 8. The compound of claim 1, wherein said cycloalkyl is (C1-C6).
- 9. The compound of claim 1, wherein R1 is n-butyl, s-butyl, i-butyl, p-toluene, p-halophenyl, or cycloalkyl.
- 10. The compound of claim 9, wherein said cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, 2-cyclohexylmethyl, or cyclohexylphenyl.
- 11. The compound of claim 1, wherein m is 0.
- 12. The compound of claim 1, wherein n is 3 or 4.
- 13. The compound of claim 1, wherein said compound is a 5-HT receptor antagonist.
- 14. The compound of claim 13, wherein said compound is a 5-HT1 receptor antagonist.
- 15. The compound of claim 14, wherein said compound is a 5-HT1A, B, C, D, E or F receptor antagonist.
- 16. The compound of claim 14, wherein said compound is a 5-HT1A receptor antagonist.
- 17. The compound of claim 16, wherein the half-life of said compound in vivo is HLM T1/2>20-90 min., up to 100% of the compound remaining unchanged.
- 18. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat generalized anxiety disorder, and a pharmaceutically-acceptable carrier.
- 19. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat sexual dysfunction, and a pharmaceutically-acceptable carrier.
- 20. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat attention deficit disorder, with or without hyperactivity, and a pharmaceutically-acceptable carrier.
- 21. A method of treating a subject afflicted with a condition requiring treatment, comprising administering an effective amount of a compound of claim 1 to treat said condition.
- 22. A method of treating a 5-HT-related condition, comprising administering an effective amount of a compound of claim 1.
- 23. A method of modulating a 5-HT receptor, comprising contacting said receptor with a compound of claim 1.
- 24. A method of treating generalized anxiety disorder, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said generalized anxiety disorder.
- 25. A method of treating generalized anxiety disorder, comprising diagnosing a patient in need of treatment and administering to a patient in need thereof a therapy including a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat generalized anxiety disorder.
- 26. A method of treating sexual dysfunction, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said sexual dysfunction.
- 27. A method of treating sexual dysfunction, comprising diagnosing a patient in need of treatment and administering to a patient in need thereof a therapy including a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said sexual dysfunction.
- 28. A method of treating attention deficit disorder, with or without hyperactivity, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said attention deficit disorder.
- 29. A method of treating attention deficit disorder, with or without hyperactivity, comprising diagnosing a patient in need of treatment and administering to a patient in need thereof a therapy including a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat attention deficit disorder.
- 30. A composition comprising 4-Methyl-N-{4-[4-(3-nitro-phenyl)-piperazin-1-yl]-butyl}-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 31. A composition comprising 4-Methyl-N-{4-[4-(3-nitro-phenyl)-piperazin-1-yl]-butyl}-benzenesulfonamide HCl.
- 32. A composition comprising N-(3-{4-[4-(Toluene-4-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-butyramide; and pharmaceutically acceptable salts and/or esters thereof.
- 33. A composition comprising 2,2-Dimethyl-N-(3-{4-[4-(toluene-4-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-propionamide; and pharmaceutically acceptable salts and/or esters thereof.
- 34. A composition comprising N-(3-{4-[4-(Toluene-4-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-isobutyramide; and pharmaceutically acceptable salts and/or esters thereof.
- 35. A composition comprising N-{4-[4-(3-Ethanesulfonylamino-phenyl)-piperazin-1-yl]-butyl}-4-methyl-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 36. A composition comprising 4-Methyl-N-(4-{4-[3-(propane-2-sulfonylamino)-phenyl]-piperazin-1-yl}-butyl)-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 37. A composition comprising 4-Methyl-N-{4-[4-(3-nitro-phenyl)-piperazin-1-yl]-butyl}-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 38. A composition comprising 4-Methyl-N-[4-(4-pyridin-2-yl-piperazin-1-yl)-butyl]-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 39. A composition comprising N-{4-[4-(2-Methoxy-5-nitro-phenyl)-piperazin-1-yl]-butyl}-4-methyl-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 40. A composition comprising 4-Methyl-N-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl]-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 41. A composition comprising N-{4-[4-(3-Methoxy-phenyl)-piperazin-1-yl]-butyl}-4-methyl-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 42. A composition comprising N-{4-[4-(3-Ethanesulfonylamino-phenyl)-piperazin-1-yl]-butyl}-4-methyl-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 43. A composition comprising N-{4-[4-(3-Methanesulfonylamino-phenyl)-piperazin-1-yl]-butyl}-4-methyl-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 44. A composition comprising 4-Methyl-N-{4-[4-(3-pyrazin-2-yl-phenyl)-piperazin-1-yl]-butyl}-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 45. A composition comprising N-[4-(4-Biphenyl-3-yl-piperazin-1-yl)-butyl]4-methyl-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 46. A composition comprising 4-Methyl-N-[4-(4-phenyl-piperazin-1-yl)-butyl]-benzenesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 47. A composition comprising C-Cyclohexyl-N-{4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-methanesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 48. A composition comprising N-(3-{4-[4-(Toluene-4-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-propionamide; and pharmaceutically acceptable salts and/or esters thereof.
- 49. A composition comprising (3-{4-[1-(4-Fluoro-benzenesulfonyl)-piperidin-4-ylmethyl]-piperazin-1-yl}-phenyl)-dimethyl-amine; and pharmaceutically acceptable salts and/or esters thereof.
- 50. A composition comprising 1-[1-(4-Fluoro-benzenesulfonyl)-piperidin-4-ylmethyl]-4-pyridin-2-yl-piperazine; and pharmaceutically acceptable salts and/or esters thereof.
- 51. A composition comprising C-Cyclohexyl-N-{4-[4-(3-dimethylamino-phenyl)-piperazin-1-yl]-butyl}-methanesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 52. A composition comprising C-Cyclohexyl-N-[4-(4-pyridin-2-yl-piperazin-1-yl)-butyl]-methanesulfonamide; and pharmaceutically acceptable salts and/or esters thereof.
- 53. A composition comprising N-(3-{4-[1-(4-Fluoro-benzenesulfonyl)-piperidin-4-ylmethyl]-piperazin-1-yl}-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 54. A composition comprising N-(3-{4-[4-(4-Fluoro-benzenesulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 55. A composition comprising 1-(2-Methoxy-phenyl)-4-[1-(toluene-4-sulfonyl)-piperidin-3-ylmethyl]-piperazine; and pharmaceutically acceptable salts and/or esters thereof.
- 56. A compound having the formula
- 57. The compound of claim 56, wherein both Z atoms are C; R2 is nitro, NHCO-alkyl, NCO-dialkyl, or aminoalkyl; and R3 is H.
- 58. The compound of claim 57, wherein said NHCO-alkyl is NHCO-lower alkyl.
- 59. The compound of claim 58, wherein said NHCO-lower alkyl is NHCO—(CH3), NHCO—(CH2CH3), NHCO—(CH2CH2—CH3), or NHCO—(CH(CH2)2.
- 60. The compound of claim 57, wherein R2 is in the meta position.
- 61. The compound of claim 56, wherein said lower alkyl or alkoxy is lower (C1-C4).
- 62. The compound of claim 56, wherein said cycloalkyl is (C1-C6).
- 63. The compound of claim 56, wherein R1 is n-butyl, s-butyl, i-butyl, p-toluene, p-halophenyl, or cycloalkyl.
- 64. The compound of claim 63, wherein said cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, or cyclohexylphenyl.
- 65. The compound of claim 56, wherein m is 0.
- 66. The compound of claim 56, wherein n is 3 or 4.
- 67. The compound of claim 56, wherein p is 1.
- 68. The compound of claim 56, wherein said compound is a 5-HT receptor agonist.
- 69. The compound of claim 56, wherein said compound is a 5-HT1 receptor agonist.
- 70. The compound of claim 56, wherein said compound is a 5-HT1A, B, C, D, E or F receptor agonist.
- 71. The compound of claim 56, wherein said compound is a 5-HT1A receptor agonist.
- 72. The compound of claim 56, wherein the half-life of said compound in vivo is HLM T1/2>20-90 min., up to 100% of the compound remaining unchanged.
- 73. A composition comprising Cyclopropanecarboxylic acid (3-{4-[4-(toluene-4-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-amide; and pharmaceutically acceptable salts and/or esters thereof.
- 74. A composition comprising N-(3-{4-[4-(Toluene-4-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 75. A composition comprising N-{3-[4-(4-Cyclohexylmethanesulfonylamino-butyl)-piperazin-1-yl]-phenyl}-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 76. A composition comprising N-{3-[4-(1-Cyclohexylmethanesulfonyl-piperidin-4-ylmethyl)-piperazin-1-yl]-phenyl}-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 77. A composition comprising Cyclopropanecarboxylic acid {3-[4-(4-cyclohexylmethanesulfonylamino-butyl)-piperazin-1-yl]-phenyl}-amide; and pharmaceutically acceptable salts and/or esters thereof.
- 78. A composition comprising N-(3-{4-[1-(Propane-2-sulfonyl)-piperidin-4-ylmethyl]-piperazin-1-yl}-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 79. A composition comprising N-(3-{4-[4-(Propane-2-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 80. A composition comprising N-{3-[4-(4-Cyclohexanesulfonylamino-butyl)-piperazin-1-yl]-phenyl}-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 81. A composition comprising N-(3-{4-[4-(Cyclohexylmethanesulfonyl-methyl-amino)-butyl]-piperazin-1-yl}-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 82. A composition comprising N-(3-{4-[4-(2-Methyl-propane-1-sulfonylamino)-butyl]-piperazin-1-yl}-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 83. A composition comprising N-[3-(4-{4-[Methyl-(2-methyl-propane-1-sulfonyl)-amino]-butyl}-piperazin-1-yl)-phenyl]-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 84. A composition comprising N-(3-piperazin-1-yl-phenyl)-acetamide; and pharmaceutically acceptable salts and/or esters thereof.
- 85. A composition comprising Cyclopropanecarboxylic acid (3-piperazin-1-yl-phenyl)-amide; and pharmaceutically acceptable salts and/or esters thereof.
- 86. A pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat generalized anxiety disorder, and a pharmaceutically-acceptable carrier.
- 87. A pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat sexual dysfunction, and a pharmaceutically-acceptable carrier.
- 88. A pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat attention deficit disorder, with or without hyperactivity, and a pharmaceutically-acceptable carrier.
- 89. A method of treating a subject afflicted with a condition requiring treatment, comprising administering an effective amount of a compound of claim 56 to treat said condition.
- 90. A method of treating a 5-HT-related condition, comprising administering an effective amount of a compound of claim 56.
- 91. A method of modulating a 5-HT receptor, comprising contacting said receptor with a compound of claim 56.
- 92. A method of treating generalized anxiety disorder, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat said generalized anxiety disorder.
- 93. A method of treating generalized anxiety disorder, comprising diagnosing a patient in need of treatment and administering to a patient in need thereof a therapy including a pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat generalized anxiety disorder.
- 94. A method of treating sexual dysfunction, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat said sexual dysfunction.
- 95. A method of treating sexual dysfunction, comprising diagnosing a patient in need of treatment and administering to a patient in need thereof a therapy including a pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat sexual dysfunction.
- 96. A method of treating attention deficit disorder, with or without hyperactivity, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat said attention deficit disorder.
- 97. A method of treating attention deficit disorder, with or without hyperactivity, comprising diagnosing a patient in need of treatment and administering to a patient in need thereof a therapy including a pharmaceutical composition comprising the compound of claim 56 in an amount effective to treat attention deficit disorder.
RELATED APPLICATIONS
[0001] This application claims the benefit of priority under 35 U.S.C. 119(e) to copending U.S. Provisional Application No. 60/443,988, filed on Jan. 31, 2003; 60/458,297, filed on Mar. 28, 2003, and 60/503,520, filed on September 16, 2003, the entire contents of which are incorporated herein by reference.
Provisional Applications (3)
|
Number |
Date |
Country |
|
60443988 |
Jan 2003 |
US |
|
60458297 |
Mar 2003 |
US |
|
60503520 |
Sep 2003 |
US |