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Claims for Patent: 4,631,286

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Claims for Patent: 4,631,286

Title: 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds
Abstract:There are disclosed compounds having the formula ##STR1## wherein X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, NHCOR.sub.2 wherein R.sub.2 is loweralkyl, or a group of the formula NR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R and R.sub.1 are independently hydrogen, loweralkyl, phenylloweralkyl, phenylloweralkyl in which the phenyl group is substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl, diphenylloweralkyl or diphenylloweralkyl in which one or both phenyl groups are substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl; Y is C.dbd.O or CR.sub.5 OH wherein R.sub.5 is hydrogen or loweralkyl; Z is CH.sub.2 or C.dbd.CR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7 are independently hydrogen or loweralkyl; or Y and Z taken together is CR.sub.5 .dbd.CH wherein CR.sub.5 and CH correspond to Y and Z respectively; an optical antipode thereof, or a pharmaceutically acceptable acid addition salt thereof, which are useful for enhancing memory, methods for synthesizing them, and pharmaceutical compositions comprising an effective memory enhancing amount of such a compound.
Inventor(s): Shutske; Gregory M. (Somerset, NJ), Pierrat; Frank A. (Somerset, NJ)
Assignee: Hoechst-Roussel Pharmaceuticals Inc. (Somerville, NJ)
Application Number:06/664,731
Patent Claims: 1. A compund having the formula ##STR18## where X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, NHCOR.sub.2 wherein R.sub.2 is loweralkyl, or a group of the formula NR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R and R.sub.1 are independently hydrogen, loweralkyl, phenylloweralkyl, phenylloweralkyl in which the phenyl group is substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl, diphenylloweralkyl or diphenylloweralkyl in which one or both phenyl groups are substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl; Y is C.dbd.O or CR.sub.5 OH wherein R.sub.5 is hydrogen or loweralkyl; Z is CH.sub.2 or C.dbd.CR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7 are independently hydrogen or loweralkyl; an optical antipode thereof, or a pharmaceutically acceptable acid addition salt thereof.

2. The compound as defined in claim 1, wherein Y is C.dbd.O.

3. The compound as defined in claim 2, wherein Z is CH.sub.2.

4. The compound as defined in claim 2, wherein Z is C.dbd.CR.sub.6 R.sub.7.

5. The compound as defined in claim 4, wherein Z is C.dbd.CH.sub.2.

6. The compound as defined in claim 3, wherein R is H.

7. The compound as defined in claim 4, wherein R is H.

8. The compound as defined in claim 5, wherein R is H.

9. The compound as defined in claim 6, wherein R.sub.1 is H.

10. The compound as defined in claim 7, wherein R.sub.1 is H.

11. The compound as defined in claim 8, wherein R.sub.1 is H.

12. The compound as defined in claim 6, wherein R.sub.1 is loweralkyl.

13. The compound as defined in claim 7, wherein R.sub.1 is loweralkyl.

14. The compound as defined in claim 8, wherein R.sub.1 is loweralkyl.

15. The compound as defined in claim 6, wherein R.sub.1 is phenylloweralkyl.

16. The compound as defined in claim 7, wherein R.sub.1 is phenylloweralkyl.

17. The compound as defined in claim 8, wherein R.sub.1 is phenylloweralkyl.

18. The compound as defined in claim 6, wherein R.sub.1 is halophenylloweralkyl.

19. The compound as defined in claim 7, wherein R.sub.1 is halophenylloweralkyl.

20. The compound as defined in claim 8, wherein R.sub.1 is halophenylloweralkyl.

21. The compound as defined in claim 6, wherein R.sub.1 is diphenylloweralkyl.

22. The compound as defined in claim 7, wherein R.sub.1 is diphenylloweralkyl.

23. The compound as defined in claim 8, wherein R.sub.1 is diphenylloweralkyl.

24. The compound as defined in claim 3, wherein X is H.

25. The compound as defined in claim 4, wherein X is H.

26. The compound as defined in claim 5, wherein X is H.

27. The compound as defined in claim 6, wherein X is H.

28. The compound as defined in claim 7, wherein X is H.

29. The compound as defined in claim 8, wherein X is H.

30. The compound as defined in claim 9, wherein X is H, which is 9-amino-3,4-dihydroacridin-1(2H)-one.

31. The compound as defined in claim 10, wherein X is H.

32. The compound as defined in claim 11, wherein X is H, which is 9-amino-3,4-dihydro-2-methyleneacridin-1(2H)-one.

33. The compound as defined in claim 12, wherein X is H.

34. The compound as defined in claim 13, wherein X is H.

35. The compound as defined in claim 14, wherein X is H.

36. The compound as defined in claim 15, wherein X is H.

37. The compound as defined in claim 16, wherein X is H.

38. The compound as defined in claim 17, wherein X is H.

39. The compound as defined in claim 18, wherein X is H.

40. The compound as defined in claim 19, wherein X is H.

41. The compound as defined in claim 20, wherein X is H.

42. The compound as defined in claim 21, wherein X is H.

43. The compound as defined in claim 22, wherein X is H.

44. The compound as defined in claim 23, wherein X is H.

45. The compound as defined in claim 6, wherein X is halogen.

46. The compound as defined in claim 7, wherein X is halogen.

47. The compound as defined in claim 8, wherein X is halogen.

48. The compound as defined in claim 6, wherein X is NO.sub.2.

49. The compound as defined in claim 7, wherein X is NO.sub.2.

50. The compound as defined in claim 8, wherein X is NO.sub.2.

51. The compound as defined in claim 6, wherein X is NHCOR.sub.2.

52. The compound as defined in claim 7, wherein X is NHCOR.sub.2.

53. The compound as defined in claim 8, wherein X is NHCOR.sub.2.

54. The compound as defined in claim 6, wherein X is NR.sub.3 R.sub.4.

55. The compound as defined in claim 7, wherein X is NR.sub.3 R.sub.4.

56. The compound as defined in claim 8, wherein X is NR.sub.3 R.sub.4.

57. The compound as defined in claim 33, wherein R.sub.1 is methyl, which is 3,4-dihydro-9-(methylamino)acridin-1(2H)-one.

58. The compound as defined in claim 33, where R.sub.1 is n-propyl, which is 3,4-dihydro-9-(n-propylamino)acridin-1(2H)-one.

59. The compound as defined in claim 36, where R.sub.1 is benzyl, which is 9-benzylamino-3,4-dihydroacridin-1(2H)-one.

60. The compound as defined in claim 36, where R.sub.1 is phenethyl, which is 3,4-dihydro-9-(phenethylamino)acridin-1-2H-one.

61. The compound as defined in claim 39, where R.sub.1 is 2-fluorobenzyl, which is 3,4-dihydro-9-(2-fluorobenzylamino)acridin-1(2H)-one.

62. The compound as defined in claim 42, where R.sub.1 is 4,4-diphenylbutyl, which is 3,4-dihydro-9-(4,4-diphenylbutylamino)acridin-1(2H)-one.

63. The compound as defined in claim 45, where R.sub.1 is H.

64. The compound as defined in claim 63, where X is chlorine.

65. The compound as defined in claim 64, where X is 7-chloro, which is 9-amino-7-chloro-3,4-dihydroacridin-1(2H)-one.

66. The compound as defined in claim 64, where X is 6-chloro, which is 9-amino-6-chloro-3,4-dihydroacridin-1(2H)-one.

67. The compound as defined in claim 48, where R.sub.1 is H.

68. The compound as defined in claim 67, where X is 7-NO.sub.2, which is 9-amino-3,4-dihydro-7-nitroacridin-1(2H)-one.

69. The compound as defined in claim 48, where R.sub.1 is methyl.

70. The compound as defined in claim 69, where X is 7-NO.sub.2, which is 3,4-dihydro-9-methylamino-7-nitroacridin-1(2H)-one.

71. The compound as defined in claim 51, where R.sub.1 is H.

72. The compound as defined in claim 71, where X is NHCOCH.sub.3.

73. The compound as defined in claim 72, where X is 7-NHCOCH.sub.3, which is N-[9-amino-3,4-dihydro-1(2H)-oxoacridin-7-yl]-acetamide.

74. The compound as defined in claim 54, where R.sub.1 is H.

75. The compound as defined in claim 74, where X is NH.sub.2.

76. The compound as defined in claim 75, where X is 7-NH.sub.2, which is 7,9-diamino-3,4-dihydroacridin-1(2H)-one.

77. The compound as defined in claim 1, wherein Y is CR.sub.5 OH.

78. The compound as defined in claim 77, wherein R.sub.5 is H.

79. The compound as defined in claim 78, wherein Z is CH.sub.2.

80. The compound as defined in claim 78, wherein Z is C.dbd.CR.sub.6 R.sub.7.

81. The compound as defined in claim 80, wherein Z is C.dbd.CH.sub.2.

82. The compound as defined in claim 79, wherein R is H.

83. The compound as defined in claim 80, wherein R is H.

84. The compound as defined in claim 81, wherein R is H.

85. The compound as defined in claim 82, wherein R.sub.1 is H.

86. The compound as defined in claim 83, wherein R.sub.1 is H.

87. The compound as defined in claim 84, wherein R.sub.1 is H.

88. The compound as defined in claim 82, wherein R.sub.1 is loweralkyl.

89. The compound as defined in claim 83, wherein R.sub.1 is loweralkyl.

90. The compound as defined in claim 84, wherein R.sub.1 is loweralkyl.

91. The compound as defined in claim 82, wherein R.sub.1 is phenylloweralkyl.

92. The compound as defined in claim 83, wherein R.sub.1 is phenylloweralkyl.

93. The compound as defined in claim 84, wherein R.sub.1 is phenylloweralkyl.

94. The compound as defined in claim 82, wherein R.sub.1 is halophenylloweralkyl.

95. The compound as defined in claim 83, wherein R.sub.1 is halophenylloweralkyl.

96. The compound as defined in claim 84, wherein R.sub.1 is halophenylloweralkyl.

97. The compound as defined in claim 79, wherein X is H.

98. The compound as defined in claim 80, wherein X is H.

99. The compound as defined in claim 81, wherein X is H.

100. The compound as defined in claim 82, wherein X is H.

101. The compound as defined in claim 83, wherein X is H.

102. The compound as defined in claim 84, wherein X is H.

103. The compound as defined in claim 85, wherein X is H, which is 9-amino-1,2,3,4-tetrahydroacridin-1-ol.

104. The compound as defined in claim 86, wherein X is H.

105. The compound as defined in claim 87, wherein X is H.

106. The compound as defined in claim 88, wherein X is H.

107. The compound as defined in claim 89, wherein X is H.

108. The compound as defined in claim 90, wherein X is H.

109. The compound as defined in claim 91, wherein X is H.

110. The compound as defined in claim 92, wherein X is H.

111. The compound as defined in claim 93, wherein X is H.

112. The compound as defined in claim 94, wherein X is H.

113. The compound as defined in claim 95, wherein X is H.

114. The compound as defined in claim 96, wherein X is H.

115. The compound as defined in claim 82, wherein X is halogen.

116. The compound as defined in claim 83, wherein X is halogen.

117. The compound as defined in claim 84, wherein X is halogen.

118. The compound as defined in claim 106, wherein R.sub.1 is methyl, which is 9-methylamino-1,2,3,4-tetrahydroacridin-1-ol.

119. The compound as defined in claim 106, wherein R.sub.1 is n-propyl, which is 9-(n-propylamino)-1,2,3,4-tetrahydroacridin-1-ol.

120. The compound as defined in claim 109, wherein R.sub.1 is benzyl, which is 9-benzylamino-1,2,3,4-tetrahydroacridin-1-ol.

121. The compound as defined in claim 109, wherein R.sub.1 is phenethyl, which is 9-phenethylamino-1,2,3,4-tetrahydroacridin-1-ol.

122. The compound as defined in claim 112, wherein R.sub.1 is 2-fluorobenzyl, which is 9-(2-fluorobenzylamino)-1,2,3,4-tetrahydroacridin-1-ol.

123. The compound as defined in claim 115, where R.sub.1 is H.

124. The compound as defined in claim 123, where X is chlorine.

125. The compound as defined in claim 124, where X is 7-chloro, which is 9-amino-7-chloro-1,2,3,4-tetrahydroacridin-1-ol.

126. The compound as defined in claim 124, where X is 6-chloro, which is 9-amino-6-chloro-1,2,3,4-tetrahydroacridin-1-ol.

127. The compound as defined in claim 77, wherein R.sub.5 is loweralkyl.

128. The compound as defined in claim 127, where R.sub.5 is methyl.

129. The compound as defined in claim 128, where R is H.

130. The compound as defined in claim 129, where R.sub.1 is H.

131. The compound as defined in claim 130, where X is H, which is 9-amino-1-methyl-1,2,3,4-tetrahydroacridin-1-ol.

132. A pharmaceutical composition which comprises an effective memory enhancing amount of a compound defined in claim 1.

133. A pharmaceutical composition which comprises an effective memory enhancing amount of a compound defined in claim 3.

134. A pharmaceutical composition which comprises an effective memory enhancing amount of a compound defined in claim 79.

135. A pharmaceutical composition which comprises an effective memory enhancing amount of a compound defined in claim 91.

136. A pharmaceutical composition which comprises an effective memory enhancing amount of a compound defined in claim 103.

137. A pharmaceutical composition which comprises an effective memory enhancing amount of a compound defined in claim 120.

138. A method of treating a patient in need of memory enhancement, wherein an effective memory enhancing amount of a compound defined in claim 1 is administered to the patient.

139. A method of treating a patient in need of memory enhancement, wherein an effective memory enhancing amount of a compound defined in claim 3 is administered to the patient.

140. A method of treating a patient in need of memory enhancement, wherein an effective memory enhancing amount of a compound defined in claim 79 is administered to the patient.

141. A method of treating a patient in need of memory enhancement, wherein an effective memory enhancing amount of a compound defined in claim 91 is administered to the patient.

142. A method of treating a patient in need of memory enhancement, wherein an effective memory enhancing amount of a compound defined in claim 103 is administered to the patient.

143. A method of treating a patient in need of memory enhancement, wherein an effective memory enhancing amount of a compound defined in claim 120 is administered to the patient.
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