Claims
- 1. A compound of formula (I):
- 2. The compound of claim 1 wherein all of said alkoxy, alkanoyl, and alkyl are lower alkoxy, lower alkanoyl and lower alkyl groups.
- 3. A compound of claim 1, wherein R5 and R6 are as above, R1, R2, R3 and R4 are independently selected from hydrogen, halogen, hydroxy, alkyl, cycloalkyl, aralkyl, aryl, alkoxy, alkoxy alkyl, halo alkyl, aryloxy, alkylcarbonyl, arylcarbonyl, alkylthio, arylthio, alkylsulfoxyl, arylsulfoxyl, alkylsulfonyl, arylsulfonyl, amino, nitro, cyano, alkanoyloxy alkyl, aryloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, carboxy or heterocyclyl;
R7 is hydrogen, alkyl or cycloalkyl, whereby R7 is not hydrogen when R6 is hydrogen, alkyl, cycloalkyl or 1H-pyrrolo(2,3-b)pyridin-3-ylmethyl; and R8 is hydrogen.
- 4. The compound of claim 3, wherein R1, R2, R3 and R4 are independently selected from hydrogen, halogen, alkyl, alkoxy, haloalkyl, halo alkoxy and cyano.
- 5. The compound of claim 4, wherein one or two of R1, R2, R3 and R4 are independently selected from chloro, bromo, methyl, trifluoromethyl and cyano and the others are hydrogen.
- 6. The compound of claim 5, wherein R5 is hydrogen.
- 7. The compound of claim 6, wherein R6 is hydrogen, hydroxyalkyl, carbamoylalkyl, alkyloxycarbonylalkyl or —(CH2)n-A.
- 8. The compound of claim 7, wherein R6 is hydrogen.
- 9. The compound of claim 8, wherein A is oxazolidinone, cyclobutanonyl, [1,2,4]triazol-3-yl, [1,2,4]oxadiazol-3-yl, [1,2,4]triazol-3-one-5-yl, tetrazolyl, [1,3,4]oxadiazol-2-yl, [1,3,4]thiadiazol-2-yl, 1H-imidazol-2-yl or 1H-imidazol-4-yl.
- 10. The compound of claim 9, wherein A is 2-oxazolidin-2-one or cyclobutanon-2-yl.
- 11. The compound of claim 10, wherein n is 0 or 1.
- 12. The compound of claim 11, wherein R7 is hydrogen or alkyl.
- 13. The compound to claim 12, wherein R7 is methyl or ethyl.
- 14. The compound to claim 13, wherein R8 is hydrogen.
- 15. The compound of claim 1 wherein said compound has the formula:
- 16. The compound of claim 15 wherein R12 and R13 are halo and R14 is hydrogen and R17 is lower alkyl.
- 17. The compound of claim 16 wherein said compound is (4R,10aR)-7-chloro-8-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 18. The compound of claim 16 wherein said compound is (4R,10aR)-9-chloro-6-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 19. The compound of claim 16 wherein said compound is (4R,10aR)-6,7-difluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 20. The compound of claim 16 wherein said compound is (4R,10aS)-6,7-difluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 21. The compound of claim 16 wherein said compound is (4R,10aR)-7-chloro-6-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 22. The compound of claim 16 wherein said compound is (4RS,10aSR)-7,8-dibromo-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 23. The compound of claim 16 wherein said compound is (4R,10aR)-7-bromo-9-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 24. The compound of claim 16 wherein said compound is (4R,10aR)-7,9-dichloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 25. The compound of claim 16 wherein said compound is (4R,10aS)-7,9-dichloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 26. The compound of claim 16 wherein said compound is (4R,10aR)-6,7-dichloro-4-methyl-1,2,3,4,10,1 a-hexahydro-pyrazino[1,2-a]indole.
- 27. The compound of claim 16 wherein said compound is (4R,10aR)-6,9-difluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole; hydrochloride.
- 28. The compound of claim 16 wherein said compound is (4R,10a R)-8-bromo-7-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 29. The compound of claim 16 wherein said compound is (4R,10a S)-8-bromo-7-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 30. The compound of claim 15 wherein R12 is halogen and R13 and R14 are hydgrogen.
- 31. The compound of claim 30 wherein R17 is methyl.
- 32. The compound of claim 31 wherein said compound is (4R,10aR)-7-chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 33. The compound of claim 31 wherein said compound is(4R,10aS)-7-chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 34. The compound of claim 31 wherein said compound is (4S,10aS)-7-chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 35. The compound of claim 31 wherein said compound is (4S,10aR)-7-chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 36. The compound of claim 31 wherein said compound is (4R,10aR)-7-bromo-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 37. The compound of claim 31 wherein said compound is (4R,10aR)-9-chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 38. The compound of claim 31 wherein said compound is (4R,10aR)-8-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 39. The compound of claim 31 wherein said compound is (4R,10aR)-6-fluoro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 40. The compound of claim 31 wherein said compound is (4R,10aS)-6-bromo-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 41. The compound of claim 30 wherein R17 is ethyl.
- 42. The compound of claim 41 wherein said compound is (4RS,10aRS)-7-bromo-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 43. The compound of claim 41 wherein said compound is (4RS,10aSR)-7-bromo-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 44. The compound of claim 41 wherein said compound is (4R,10aR)-7-bromo-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole
- 45. The compound of claim 41 wherein said compound is (4S,10aS)-7-bromo-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 46. The compound of claim 41 wherein said compound is 7-chloro-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 47. The compound of claim 46 wherein said compound is (4R,10aR)-7-chloro-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 48. The compound of claim 46 wherein said compound is (4R,10aS)-7-chloro-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 49. The compound of claim 46 wherein said compound is (4S,10aS)-7-chloro-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 50. The compound of claim 46 wherein said compound is (4S,10aR)-7-chloro-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 51. The compound of claim 15 wherein R12, R13 and R14 are halo and R17 is lower alkyl.
- 52. The compound of claim 51 wherein said compound is (4RS,10aRS)-6,7,8-tribromo-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 53. The compound of claim 15 wherein R12 is hydrogen and R13 and R14 are independently hydrogen or lower alkyl; and R17 is lower alkyl.
- 54. The compound of claim 53 wherein said compound is (4R,10aS)-6-ethyl-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 55. The compound of claim 53 wherein said compound is (4R,10aR)-6-ethyl-4-methyl-1,2,3,4,10,1 a-hexahydro-pyrazino[1,2-a]indole.
- 56. The compound of claim 53 wherein said compound is (4R,10aR)-4,6,7-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]l indole hydrochloride.
- 57. The compound of claim 53 wherein said compound is (4RS,10aSR)-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 58. The compound of claim 53 wherein said compound is (4RS,10aRS)-4-ethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 59. The compound of claim 53 wherein said compound is (4R,10S,10aR)-4,6,10-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 60. The compound of claim 53 wherein said compound is (4R,10R,10aR)-4,6,10-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 61. The compound of claim 53 wherein said compound is (4R,10aR)-4,6-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 62. The compound of claim 53 wherein said compound is (4R, 10aS)-4,6-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 63. The compound of claim 53 wherein said compound is (4R,10aR)-4,7,9-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 64. The compound of claim 53 wherein said compound is (4R,10aR)-4,6,9-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 65. The compound of claim 53 wherein said compound is (4R,10aS)-4,6,7-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indol.
- 66. The compound of claim 53 wherein said compound is (4R,10aS)-4,6,9-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 67. The compound of claim 53 wherein said compound is (4R,10aR)-4,8-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole trifluoroacetate.
- 68. The compound of claim 53 wherein said compound is (4R,10aS) 4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 69. The compound of claim 53 wherein said compound is (4R,10aR) 4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 70. The compound of claim 53 wherein said compound is (4R,10aR)-4,7,8-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 71. The compound of claim 53 wherein said compound is (4R,10aS) 4,7,8-trimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 72. The compound of claim 15 wherein R12 is hydrogen, one of R13 and R14 is halo and the other is lower alkyl and R17 is lower alkyl.
- 73. The compound of claim 72 wherein said compound is (4R,10aR)-8-fluoro-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 74. The compound of claim 72 wherein said compound is (4R,10aS)-8-fluoro-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 75. The compound of claim 72 wherein said compound is (4R,10aR)-6-fluoro-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole; hydrochloride.
- 76. The compound of claim 72 wherein said compound is (4R,10aS)-6-fluoro-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole; hydrochloride.
- 77. The compound of claim 72 wherein said compound is (4R,10aS)-7-chloro-4,8-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 78. The compound of claim 72 wherein said compound is (4R,10aR)-7-chloro-4,8-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 79. The compound of claim 72 wherein said compound is 4R,10aR)-6-fluoro-4,9-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 80. The compound of claim 72 wherein said compound is (4R,10aS)-6-fluoro-4,9-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 81. The compound of claim 72 wherein said compound is (4R,10aR)-6-chloro-4,8-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 82. The compound of claim 72 wherein said compound is (4R,10aS)-6-chloro-4,8-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 83. The compound of claim 72 wherein said compound is (4R,10aR)-7-chloro-4,6-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 84. The compound of claim 72 wherein said compound is (4R,10aS)-7-chloro-4,6-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 85. The compound of claim 72 wherein said compound is 4R,10aS)-6-chloro-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 86. The compound of claim 72 wherein said compound is (4R,10aR)-6-chloro-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 87. The compound of claim 72 wherein said compound is (4R,10a R)-8-bromo-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 88. The compound of claim 72 wherein said compound is (4R,10a S)-8-bromo-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 89. The compound of claim 72 wherein said compound is (4R,10aS)-8-fluoro-4,6-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 90. The compound of claim 72 wherein said compound is (4R,10aR)-8-fluoro-4,6-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole; hydrochloride.
- 91. The compound of claim 72 wherein said compound is (4R,10aR)-6-bromo-4,7-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 92. The compound of claim 72 wherein said compound is (4R,10aR)-8-bromo-6-ethyl-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 93. The compound of claim 72 wherein said compound is (4R,10aR)-7-fluoro-4,6-dimethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 94. The compound of claim 15 wherein R12 is hydrogen, one of R13 and R14 is trifluoromethyl, trifluoromethoxy or cyano and the other is hydrogen, halo or lower alkyl.
- 95. The compound of claim 94 wherein R17 is methyl.
- 96. The compound of claim 95 wherein R13 is trifluoromethyl.
- 97. The compound of claim 96 wherein said compound is (4R,10aR)-4-methyl-7-trifluoromethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 98. The compound of claim 96 wherein said compound is (4R,10aS)-4-methyl-7-trifluoromethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 99. The compound of claim 96 wherein said compound is (4R,10aR)-4,8-dimethyl-7-trifluoromethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 100. The compound of claim 96 wherein said compound is (4R,10aS)-4,8-dimethyl-7-trifluoromethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 101. The compound of claim 96 wherein said compound is (4R,10aS)-8-bromo-4-methyl-7-trifluoromethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 102. The compound of claim 96 wherein said compound is (4R,10aR)-8-bromo-4-methyl-7-trifluoromethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole hydrochloride.
- 103. The compound of claim 95 wherein R13 is cyano.
- 104. The compound of claim 103 wherein said compound is (4R,10aR)-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole-7-carbonitrile hydrochloric acid.
- 105. The compound of claim 104 wherein said compound is (4R,10aR)-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole-6-carbonitrile hydrochloride.
- 106. The compound of claim 95 wherein R13 is trifluoromethoxy.
- 107. The compound of claim 106 wherein said compound is (4R,10aR)-4-methyl-6-trifluoromethoxy-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 108. The compound of claim 94 wherein R17 is hydroxylower alkyl.
- 109. The compound of claim 108 wherein R13 is trifluoromethyl.
- 110. The compound of claim 109 wherein said compound is (4S,10aS)-(7-trifluoromethyl-1,2,3,4,10,1α-hexahydro-pyrazino[1,2-a]indol-4-yl)-methanol.
- 111. the compound of claim 108 wherein said compound is (4S,10aR)-(7-trifluoromethyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indol-4-yl)-methanol.
- 112. The compound of claim 1 wherein said compound has the formula
- 113. The compound of claim 112 wherein R22 and R23 form with their attached carbon atoms said carbocyclic ring.
- 114. The compound of claim 113 wherein said compound is (10R,6aS)-10-methyl-2,3,6,6a,7,8,9,10-octahydro-1H-8,10a-diaza-cyclopenta[c]fluorene hydrochloride.
- 115. The compound of claim 112 wherein one of R22 and R23 is hydrogen and the other is hydroxy lower alkyl, lower alkylaminocarbonyl, di-lower alkylaminocarbonyl, lower alkoxy-lower alkyl, lower alkyl carbonylamino or lower alkoxy lower alkoxy lower alkyl.
- 116. The compound of claim 115 wherein said compound is (4R,10aR)-N-(4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indol-7-yl)-acetamide; hydrochloride.
- 117. The compound of claim 115 wherein said compound is (4R,10aR)-(4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indol-7-yl)-methanol; hydrochloride.
- 118. The compound of claim 115 wherein said compound is (4R,10aR)-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole-7-carboxylic acid butylamide; hydrochloride.
- 119. The compound of claim 115 wherein said compound is (4R,10aR)-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole-7-carboxylic acid diethylamide hydrochloride.
- 120. The compound of claim 115 wherein said compound is (4R,10aR)-7-methoxymethyl-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 121. The compound of claim 115 wherein said compound is (4R,10aR)-7-(2-methoxy-ethoxymethyl)-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole.
- 122. The compound of claim 1 wherein said compound has the formula:
- 123. The compound of claim 122 wherein said compound is (2S,10aR) and (2R,10aR)-2-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-yl)-cyclobutanone.
- 124. The compound of claim 122 wherein said compound is (2S,10aS) and (2R,10aS)-2-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-yl)-cyclobutanone.
- 125. The compound of claim 122 wherein said compound is (10aR)-3-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-ylmethyl)-oxazolidin-2-one.
- 126. The compound of claim 122 wherein said compound is (10aS)-3-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-ylmethyl)-oxazolidin-2-one.
- 127. The compound of claim 122 wherein said compound is (10aR)-2-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-yl)-ethanol.
- 128. The compound of claim 122 wherein said compound is (10aR)-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-yl)-acetic acid methyl ester.
- 129. The compound of claim 122 wherein said compound is (10aR)-2-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-yl)-acetamide.
- 130. A method of treatment of obesity or Type II diabetes in a human in need of such treatment which comprises administration to the human a therapeutically effective amount of the compound of claim 1 in conjunction with a therapeutically effective amount of a lipase inhibitor.
- 131. The method of claim 130 wherein the lipase inhibitor is orlistat.
- 132. The method of claim 131 wherein the orlistat and the compound of formula I are simultaneously, separately or sequentially administered.
- 133. A pharmaceutical composition comprising a compound of claim 1 in combination with a pharmaceutically acceptable carrier or excipient.
- 134. The pharmaceutical composition of claim 133 wherein the composition contains a therapeutically effective amount of a lipase inhibitor.
- 135. The pharmaceutical composition of claim 134 wherein the lipase inhibitor is orlistat.
Priority Claims (1)
Number |
Date |
Country |
Kind |
00116517.4 |
Jul 2000 |
EP |
|
CONTINUITY INFORMATION
[0001] This application is a continuation of Ser. No. 09/912,949, filed Jul. 25, 2001.
Continuations (1)
|
Number |
Date |
Country |
Parent |
09912949 |
Jul 2001 |
US |
Child |
10396242 |
Mar 2003 |
US |