| Sonstiges: |
- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 7,141,595
- Publication Date: November 28, 2006
- Appl. No: 10/995146
- Application Filed: November 24, 2004
- Assignees: Neuraxon Inc. (Toronto, CA)
- Claim: 1. A compound of Formula I, and pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof: [chemical expression included] wherein R 1 is selected from the group consisting of: [chemical expression included] R 2 is selected from the group consisting of H, [chemical expression included] —(CH 2) n R 8 and —(CH 2) m R 9 R 3 is selected from the group consisting of C 1-6 alkyl, SC 1-6 alkyl, thienyl and furanyl; R 4 is selected from the group consisting of H, C 1-6 alkyl, Ph, C(O)Ph and —C(O)C 1-6 alkyl; R 5 and R 6 are independently selected from the group consisting of H and C 1-6 alkyl or together R 5 and R 6 and the nitrogen to which they are attached form a 3 to 7-membered azacarbocylic ring wherein one of the carbon atoms in the ring may optionally be replaced with O, S, or NR 7 ; R 7 is selected from the group consisting of H, C 1-6 alkyl, Ph, Heteroaryl, CH 2 Ph, and CH 2 Heteroaryl, with Ph and Heteroaryl being optionally substituted with 1–3 groups independently selected from the group consisting of C 1-4 alkyl, halo, OH, OC 1-4 alkyl, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro and cyano; R 8 is selected from the group consisting of H, OH, Ph, naphthyl and heteroaryl, with Ph, naphthyl and heteroaryl being optionally substituted with 1–3 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl; R 9 is C 3-7 cycloalkyl optionally substituted with 1–3 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl and one or two of the carbon atoms in C 3-7 cycloalkyl may optionally be replaced with O or S; n is 1–6; m is 0–6; o is 0–2; p is 1–2; and the group R 1 NH— is attached to the 5- or 6-position of the aminobenzothiazole ring, with the proviso that, when R 2 is H then R 4 is not C 1-6 alkyl.
- Claim: 2. The compound according to claim 1 , wherein R 3 is selected from the group consisting of C 1-2 alkyl, SC 1-4 alkyl and thienyl.
- Claim: 3. The compound according to claim 2 , wherein R 3 is selected from the group consisting of SC 1-2 alkyl and thienyl.
- Claim: 4. The compound according to claim 1 , wherein R 4 is selected from the group consisting of H, C 1-4 alkyl, Ph, C(O)Ph and —C(O)C 1-4 alkyl.
- Claim: 5. The compound according to claim 4 , wherein R 4 is selected from the group consisting of H, and C(O)Ph.
- Claim: 6. The compound according to claim 1 , wherein R 5 and R 6 are independently selected from a group consisting of H and C 1-4 alkyl or together R 5 and R 6 and the nitrogen to which they are attached form a 4 to 6-membered azacarbocylic ring wherein one of the carbon atoms in the ring may optionally be replaced with O, S, or NR 7 .
- Claim: 7. The compound according to claim 6 , wherein R 5 and R 6 are independently selected from a group consisting of H and CH 3 or together R 5 and R 6 and the nitrogen to which they are attached form a 5 to 6-membered azacarbocylic ring.
- Claim: 8. The compound according to claim 1 , wherein R 7 is selected from H, C 1-4 alkyl, Ph, Heteroaryl, CH 2 Ph, and CH 2 Heteroaryl, with Ph and Heteroaryl being optionally substituted with 1–2 groups independently selected from the group consisting of C 1-4 alkyl, halo, OH, OC 1-4 alkyl, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro and cyano.
- Claim: 9. The compound according to claim 8 , wherein R 7 is selected from H, C 1-4 alkyl, Ph, Heteroaryl, CH 2 Ph, and CH 2 Heteroaryl, with Ph and Heteroaryl being optionally substituted with 1 group independently selected from the group consisting of C 1-4 alkyl, halo, OH, OC 1-4 alkyl, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro and cyano.
- Claim: 10. The compound according to claim 9 , wherein R 7 is selected from H, Ph, C 1-4 alkyl and CH 2 Ph, with Ph being optionally substituted with 1 groups independently selected from the group consisting of C 1-4 alkyl, halo, OH, OC 1-4 alkyl, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro and cyano.
- Claim: 11. The compound according to claim 10 , wherein R 7 is selected from H, C 1-2 alkyl, Ph and CH 2 Ph, with Ph being optionally substituted with 1 groups independently selected from the group consisting of methyl, halo, OH, methoxy, NH 2 , NHMe, NMe 2 nitro and cyano.
- Claim: 12. The compound according to claim 11 , wherein R 7 is selected from methyl and CH 2 Ph.
- Claim: 13. The compound according to claim 1 , wherein R 8 is selected from the group consisting of H, OH, Ph and heteroaryl, with Ph and heteroaryl being optionally substituted with 1–2 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 14. The compound according to claim 13 , wherein R 8 is selected from the group consisting of H, OH, Ph, and heteroaryl, with Ph and heteroaryl being optionally substituted with 1 group independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 15. The compound according to claim 14 , wherein heteroaryl is a 5 or 6 membered aromatic ring.
- Claim: 16. The compound according to claim 15 , wherein heteroaryl is selected from pyridyl, imidazolyl, thienyl and furanyl.
- Claim: 17. The compound according to claim 1 , wherein R 9 is C 3-7 cycloalkyl optionally substituted with 1–2 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl and wherein one of the carbon atoms in C 3-7 cycloalkyl may optionally be replaced with O or S.
- Claim: 18. The compound according to claim 17 , wherein R 9 is C 5-7 cycloalkyl optionally substituted with 1 group independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl and wherein one of the carbon atoms in C 3-7 cycloalkyl may optionally be replaced with O or S.
- Claim: 19. The compound according to claim 18 , wherein R 9 is C 5-7 cycloalkyl herein one of the carbon atoms in C 3-7 cycloalkyl may optionally be replaced with O.
- Claim: 20. The compound according to claim 17 , wherein R 9 is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, tetrahydropyranyl and tetrahydrofuran.
- Claim: 21. The compound according to claim 1 , wherein n is 1–4.
- Claim: 22. The compound according to claim 21 , wherein n is 2.
- Claim: 23. The compound according to claim 1 , wherein m is 0–2.
- Claim: 24. The compound according to claim 23 , wherein m is 0.
- Claim: 25. The compound according to claim 1 , wherein both o and p are 1 to provide a pyrrolidinyl ring.
- Claim: 26. The compound according to claim 1 , wherein o is 2 and p is 1, to provide a piperidinyl ring.
- Claim: 27. The compound according to claim 1 , wherein R 1 is [chemical expression included]
- Claim: 28. The compound according to claim 1 , wherein R 1 is [chemical expression included]
- Claim: 29. The compound according to claim 1 that is selected from the group consisting of: N-(2-Amino-benzothiazol-6-yl)-methylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-ethylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-propylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-isopropylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-methylcarboximidamide; N-(2-Amino-benzothiazol-6-yl)-thiophenecarboximidamide; N-[2-(2-pyrrolidin-1-ylethylamino)-benzothiazol-6-yl]-2-thiophenecarboximidamide; 1-(2-Amino-benzothiazol-5-yl)-3-benzoyl-thiourea; 1-(2-Amino-benzothiazol-5-yl)-3-ethyl-thiourea; N-(2-Amino-benzothiazol-5-yl)-thiophene-2-carboxamidine; N5-Thiazol-2-yl-benzothiazole-2,5-diamine; (2-Amino-benzothiazol-5-yl)-thiourea; N-[2-(Tetrahydro-pyran-4-ylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-{2-[2-(4-Bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiophene-2-carboxamidine; N-[2-(2-Pyridin-2-yl-ethylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-[2-(1-Benzyl-piperidin-4-ylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-{2-[2-(3H-Imidazol-4-yl)-ethylamino]-benzothiazol-6-yl}-thiophene-2-carboxamidine; N-[2-(2-Morpholin-4-yl-ethylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-[2-(2-Dimethylamino-ethylamino)-benzothiazol-5-yl]-thiophene-2-carboxamidine; N-{2-[2-(1-Methyl-pyrrolidin-2-yl)-ethylamino]-benzothiazol-5-yl}-thiophene-2-carboxamidine; N-{2-[2-(3-Chloro-phenyl)-ethylamino]-benzothiazol-6-yl}-thiophene-2-carboxamidine; N-[2-(4-Hydroxy-butylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-[2-(3-Imidazol-1-yl-propylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N2-(1-Benzyl-piperidin-4-yl)-N-6-thiazol-2-yl-benzothiazole-2,6-diamine; 1-Benzoyl-3-{2-[2-(4-bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiourea; {2-[2-(4-Bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiourea; and 1-{2-[2-(4-Bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-2-ethyl-isothiourea.
- Claim: 30. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.
- Claim: 31. A pharmaceutical composition comprising a compound according to claim 29 and a pharmaceutically acceptable carrier.
- Claim: 32. A method of treating, or reducing the risk of, a disease or condition which benefits from an inhibition of NOS activity comprising administering an effective amount of a compound of Formula I according to claim 1 to a cell or animal in need thereof, wherein the disease or condition is selected from the group consisting of migraine, a reversible obstructive airway disease, asthma, adult respiratory distress syndrome (ARDS), stroke, neurological deficits associated with coronary artery bypass graft (CABG), chronic pain, neuropathic pain, traumatic shock, reperfusion injury, multiple sclerosis, AIDS associated dementia, neuron toxicity, alcohol dependency, nicotine dependency, opioid induced tolerance and withdrawal symptoms, epilepsy, anxiety, head trauma, acute spinal cord injury, Huntington's disease, Parkinson's disease, Alzheimer's disease, glaucoma, macular degeneration, neurodegeneration and diabetic nephropathy.
- Claim: 33. The method according to claim 32 , wherein the disease or condition that benefits from an inhibition of NOS activity is selected from the group consisting of stroke, reperfusion injury, neurodegeneration, head trauma, neurological deficits associated with CABG, migraine, neuropathic pain and chronic pain.
- Claim: 34. The method according to claim 33 , wherein the disease or condition that benefits from an inhibition of NOS activity is neuropathic pain.
- Claim: 35. The method according to claim 33 , wherein the disease or condition that benefits from an inhibition of NOS activity is migraine.
- Claim: 36. The method according to claim 33 , wherein the disease or condition that benefits from an inhibition of NOS activity is stroke.
- Claim: 37. The method according to claim 33 , wherein the disease or condition that benefits from an inhibition of NOS activity is opioid induced tolerance and withdrawal symptoms.
- Claim: 38. The method according to claim 32 , wherein R 3 in the compound of Formula I is selected from the group consisting of C 1-2 alkyl, SC 1-4 alkyl and thienyl.
- Claim: 39. The method according to claim 38 , wherein R 3 is selected from the group consisting of SC 1-2 alkyl and thienyl.
- Claim: 40. The method according to claim 32 , wherein R 4 in the compound of Formula I is selected from the group consisting of H, C, 1-4 alkyl, Ph, C(O)Ph and —C(O)C 1-4 alkyl.
- Claim: 41. The method according to claim 38 , wherein R 4 in the compound of Formula I is selected from the group consisting of H, and C(O)Ph.
- Claim: 42. The method according to claim 32 , wherein R 5 and R 6 in the compound of Formula I are independently selected from a group consisting of H and C 1-4 alkyl or together R 5 and R 6 and the nitrogen to which they are attached form a 4 to 6-membered azacarbocylic ring wherein one of the carbon atoms in the ring may optionally be replaced with O, S, or NR 7 .
- Claim: 43. The method according to claim 42 , wherein R 5 and R 6 in the compound of Formula I are independently selected from a group consisting of H and CH 3 or together R 5 and R 6 and the nitrogen to which they are attached form a 5 to 6-membered azacarbocylic ring.
- Claim: 44. The method according to claim 32 , wherein in the compound of Formula I R 7 is selected from H, C 1-4 alkyl, Ph, Heteroaryl, CH 2 Ph, and CH 2 Heteroaryl, with Ph and Heteroaryl being optionally substituted with 1–2 groups independently selected from the group consisting of C 1-4 alkyl, halo, OH, OC 1-4 alkyl, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro and cyano.
- Claim: 45. The method according to claim 44 , wherein in the compound of Formula I R 7 is selected from H, C 1-4 alkyl, Ph, Heteroaryl, CH 2 Ph, and CH 2 Heteroaryl, with Ph and Heteroaryl being optionally substituted with 1 group independently selected from the group consisting of C 1-4 alkyl, halo, OH, OC 1-4 alkyl, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro and cyano.
- Claim: 46. The method according to claim 45 , wherein in the compound of Formula I R 7 is selected from H, Ph, C 1-4 alkyl and CH 2 Ph, with Ph being optionally substituted with 1 groups independently selected from the group consisting of C 1-4 alkyl, halo, OH, OC 1-4 alkyl, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro and cyano.
- Claim: 47. The method according to claim 46 , wherein in the compound of Formula I R 7 is selected from H, C 1-2 alkyl, Ph and CH 2 Ph, with Ph being optionally substituted with 1 groups independently selected from the group consisting of methyl, halo, OH, methoxy, NH 2 , NHMe, NMe 2 nitro and cyano.
- Claim: 48. The method according to claim 47 , wherein in the compound of Formula I R 7 is selected from methyl and CH 2 Ph.
- Claim: 49. The method according to claim 32 , wherein in the compound of Formula I R 8 is selected from the group consisting of H, OH, Ph and heteroaryl, with Ph and heteroaryl being optionally substituted with 1–2 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 50. The method according to claim 49 , wherein in the compound of Formula I R 8 is selected from the group consisting of H, OH, Ph, and heteroaryl, with Ph and heteroaryl being optionally substituted with 1 group independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 51. The method according to claim 50 , wherein in the compound of Formula I heteroaryl is a 5 or 6 membered aromatic ring.
- Claim: 52. The method according to claim 51 , wherein in the compound of Formula I heteroaryl is selected from pyridyl, imidazolyl, thienyl and furanyl.
- Claim: 53. The method according to claim 32 , wherein in the compound of Formula I R 9 is C 3-7 cycloalkyl optionally substituted with 1–2 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl and wherein one of the carbon atoms in C 3-7 cycloalkyl may optionally be replaced with O or S.
- Claim: 54. The method according to claim 53 , wherein in the compound of Formula I R 9 is C 5-7 cycloalkyl optionally substituted with 1 group independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl and wherein one of the carbon atoms in C 3-7 cycloalkyl may optionally be replaced with O or S.
- Claim: 55. The method according to claim 54 , wherein in the compound of Formula I R 9 is C 5-7 cycloalkyl herein one of the carbon atoms in C 3-7 cycloalkyl may optionally be replaced with O.
- Claim: 56. The method according to claim 55 , wherein in the compound of Formula I R 9 is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, tetrahydropyranyl and tetrahydrofuran.
- Claim: 57. The method according to claim 32 , wherein in the compound of Formula I n is 1–4.
- Claim: 58. The method according to claim 57 , wherein in the compound of Formula I n is 2.
- Claim: 59. The method according to claim 32 , wherein in the compound of Formula I m is 0–2.
- Claim: 60. The method according to claim 59 , wherein in the compound of Formula I m is 0.
- Claim: 61. The method according to claim 32 , wherein in the compound of Formula I both o and p are 1 to provide a pyrrolidinyl ring.
- Claim: 62. The method according to claim 32 , wherein in the compound of Formula I o is 2 and p is 1 to provide a piperidinyl ring.
- Claim: 63. The method according to claim 32 , wherein in the compound of Formula I R 1 is [chemical expression included]
- Claim: 64. The method according to claim 32 , wherein in the compound of Formula I R 1 is [chemical expression included]
- Claim: 65. The method according to claim 63 , wherein R 3 is selected from the group consisting of thienyl and furanyl.
- Claim: 66. The method according to 65 , wherein in the compound of Formula I, R 2 is [chemical expression included]
- Claim: 67. The method according to claim 66 , wherein m is 0.
- Claim: 68. The method according to claim 67 , wherein o is 2 and p is 1 to provide a piperidinyl ring.
- Claim: 69. The method according to claim 68 , wherein R 7 is CH 2 Ph and Ph is optionally substituted with 1–3 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 70. The method according to claim 69 , wherein R 7 is CH 2 Ph and Ph is optionally substituted with 1 group selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 71. The method according to claim 70 , wherein R 7 is CH 2 Ph and Ph is substituted with halo.
- Claim: 72. The method according to claim 32 , wherein, in the compound of Formula I, heteroaryl is selected from the group consisting of pyridinyl, imidazolyl, thienyl, furanyl, indolyl, isoquinolinyl, quinolinyl, benzothienyl and benzofuranyl.
- Claim: 73. The method according to claim 32 , wherein, in the compound of Formula I, C 3-7 cycloalkyl is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, wherein, in each of the latter groups, one or two of the carbon atoms is optionally replaced with O or S.
- Claim: 74. The method according to claim 32 , wherein in the compound of Formula I, the 3- to 7-membered azacarbocyclic ring is selected from the group consisting of pyrolidine, piperazine and homopiperazine wherein, in each of the latter groups, one of the carbon atoms is optionally replaced with O, S or NR 7 .
- Claim: 75. The method according to claim 32 wherein the compound of Formula I is selected from the group consisting of: N-(2-Amino-benzothiazol-6-yl)-methylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-ethylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-propylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-isopropylthiocarboximidamide; N-(2-Amino-benzothiazol-6-yl)-methylcarboximidamide; N-(2-Amino-benzothiazol-6-yl)-2-thiophenecarboximidamide; N-[2-(2-pyrrolidin-1-ylethylamino)-benzothiazol6yl]-2-thiophenecarboximidamide; 1-(2-Amino-benzothiazol-5-yl)-3-benzoyl-thiourea; 1-(2-Amino-benzothiazol-5-yl)-3-ethyl-thiourea; N-(2-Amino-benzothiazol-5-yl)-thiophene-2carboxamidine; N5-Thiazol-2-yl-benzothiazole-2,5-diamine; (2-Amino-benzothiazol-5-yl)-thiourea; N-[2-(Tetrahydro-pyran-4-ylamino)-benzothiazol-6-yl]-thiophene-2carboxamidine; N-{2-[2-(4-Bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiophene-2-carboxamidine; N-[2-(2-Pyridin-2-yl-ethylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-[2-(1-Benzyl-piperidin-4-ylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-{2-[2-(3H-Imidazol-4-yl)-ethylamino]-benzothiazol-6-yl}-thiophene-2-carboxamidine; N-[2-(2-Morpholin-4-yl-ethylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-[2-(2-Dimethylamino-ethylamino)-benzothiazol-5-yl]-thiophene-2-carboxamidine; N-{2-[2-(1-Methyl-pyrrolidin-2-yl)-ethylamino]-benzothiazol-5-yl}-thiophene-2-carboxamidine; N-{2-[2-(3-Chloro-phenyl)-ethylamino]-benzothiazol-6-yl}-thiophene-2-carboxamidine; N-[2-(4-Hydroxy-butylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N-[2-(3-Imidazol-1-yl-propylamino)-benzothiazol-6-yl]-thiophene-2-carboxamidine; N2-(1-Benzyl-piperidin-4-yl)-N6-thiazol-2-yl-benzothiazole-2,6-diamine; 1-Benzoyl-3-{2-[2-(4-bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiourea; {2-[2-(4-Bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiourea; and 1-{2-[2-(4-Bromo-phenyl)-ethylamino]-benzothiazol-6yl}-2ethyl-isothiourea.
- Claim: 76. The compound according to claim 27 , wherein R 3 is selected from the group consisting of thienyl and furanyl.
- Claim: 77. The compound according to claim 76 , wherein R 2 is [chemical expression included]
- Claim: 78. The compound according to claim 77 , wherein m is 0.
- Claim: 79. The compound according to claim 78 , wherein o is 2 and p is 1 to provide a piperidinyl ring.
- Claim: 80. The compound according to claim 79 , wherein R 7 is CH 2 Ph and Ph is optionally substituted with 1–3 groups independently selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl), nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 81. The compound according to claim 80 , wherein R 7 is CH 2 Ph and Ph is optionally substituted with 1 group selected from the group consisting of C 1-4 alkyl, halo, NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl)(C 1-4 alkyl) nitro, cyano, OH and OC 1-4 alkyl.
- Claim: 82. The compound according to claim 81 , wherein R 7 is CH 2 Ph and Ph is substituted with halo.
- Claim: 83. The compound according to claim 1 , wherein heteroaryl is selected from the group consisting of pyridinyl, imidazolyl, thienyl, furanyl, indolyl, isoquinolinyl, quinolinyl, benzothienyl and benzofuranyl.
- Claim: 84. The compound according to claim 1 , wherein C 3-7 cycloalkyl is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, wherein, in each of the latter groups, one or two of the carbon atoms is optionally replaced with O or S.
- Claim: 85. The compound according to claim 1 , wherein the 3- to 7-membered azacarbocyclic ring is selected from the group consisting of pyrolidine, piperazine and homopiperazine, wherein, in each of the latter groups, one of the carbon atoms is optionally replaced with O, S or NR 7 .
- Current U.S. Class: 514/367
- Patent References Cited: 5677321 October 1997 Jeon et al. ; 6156777 December 2000 Rohde et al. ; 2003/0134859 July 2003 Amemiya et al. ; 0282971 September 1988 ; WO 95/09619 April 1995 ; WO 97/15306 May 1997 ; WO 00/69838 November 2000 ; WO 01/94325 December 2001
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- Assistant Examiner: Barker, Michael P.
- Primary Examiner: Saeed, Kamal A.
- Attorney, Agent or Firm: Folkins, Patricia
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