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(12) Patent Application Publication (10) Pub. No.: US 2003/0236225A1 Protopopova Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2003/0236225A1 Protopopova Et Al US 20030236225A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2003/0236225A1 Protopopova et al. (43) Pub. Date: Dec. 25, 2003 (54) METHODS OF USE AND COMPOSITIONS (22) Filed: May 17, 2002 FOR THE DAGNOSS AND TREATMENT OF INFECTIOUS DISEASE Publication Classification (76) Inventors: Marina Nikolaevna Protopopova, (51) Int. Cl.' ....................... A61 K 31/695; A61K 31/46; Silver Spring, MD (US); Richard A61K 31/445; A61K 31/137; Edward Lee, Cordova, TN (US); A61K 31/13 Richard Allan Slayden, Collins, CO (52) U.S. Cl. ............................ 514/63; 514/304, 514/649; (US); Clifton E. Barry III, Rockville, 514/659; 514/331; 54.6/124; MD (US) 546/246; 564/367; 564/453 Correspondence Address: (57) ABSTRACT JOHN S. PRATT, ESQ Methods and compositions for treating disease caused by KILPATRICK STOCKTON, LLP microorganisms, particularly tuberculosis. In particular, 1100 PEACHTREE STREET methods and compositions comprising Substituted ethylene SUTE 2800 diamines for the treatment of infectious diseases are pro ATLANTA, GA 30309 (US) Vided. In one embodiment, these methods and compositions are used for the treatment of mycobacterial infections, (21) Appl. No.: 10/147,587 including, but not limited to, tuberculosis. Patent Application Publication Dec. 25, 2003. Sheet 1 of 61 US 2003/0236225A1 RNH2/ENG-Pr). MeO ulCICHCHCl, RT MeO Py/THF Me PyBroP X,Y = Cl, Br Rink-acidO resin X= Cl, Br EtN(iso-Pr)2 R=H,4. Me, Et, Bu -NR O --O Me R4 X NHR2R3, Etn(-Pr). NHR2R3, Etn(-Pr). DMF, 70°C DMF, 70°C CCl6 10% TFACIC FIGURE 1 Patent Application Publication Dec. 25, 2003 Sheet 2 of 61 US 2003/0236225A1 Primary Amines 1. NH2 1. 4-Methylbenzylamine H3C 2. 2. Cyclopentylamine 3. N 3. 2-(Aminomethylo)pyridine 2 O NH2 6. Furfurylamine r C H 7. o-3 O HC1 Cu NH O 2 7. 3,4,5-Trimethoxybenzylamine C H3 NH 2 CH3 8. 1-Methyl-3-phenylproplyamine 9. NH2 9. Cyclobutylamine ? 10. H2 10. 1,2,3,4-Trimethoxybenzylamine FIGURE 2(a) Patent Application Publication Dec. 25, 2003. Sheet 3 of 61 US 2003/0236225A1 NH2 11. c 11. 2,3-Dimethylcyclohexylamine CH 12. Tyramine HO 3. 13. 2.-Fluorobenzylamine CreF (R) H erro 16. (R)-2-Amino-1-butanol NH2 1 CH 3 1 7. O H 3 17. 3,4-Dimethoxyphenethylamine “Cul NH 2 18 NH2 18. 3,3-Diphenylpropylamine 19 r 19. Propylamine CH3 21. r NH2 N 21. 1-(2-Aminoethyl)piperidine O FIGURE 20b) Patent Application Publication Dec. 25, 2003. Sheet 4 of 61 US 2003/0236225A1 22. 22. Phenethylamine rNH, C)O 23. 4-(2-Aminoethyl)morpholine NH2 24. (S)ch 24. (S)-Phenylglycinol 25 H N 25. Tryptamine 27. Cyclohexylamine 28a. ACH NH, H3C 28a. (+)-Isopinocampheylamine H3C 29. 29. Benzylamine 30. 30. 3-Amino-1-propanol H2N 1N1 No 31. 31. 2-Fluorophenethylamine F FIGURE 20c) Patent Application Publication Dec. 25, 2003 Sheet 5 of 61 US 2003/0236225A1 CH3 33. NH2 33. b-Methylphenethylamine 34. 1. O H3C Olus 34. 4-Methoxyphenethylamine NH2 35. ill 1. N n-1N 35. N,N-Dimethylethylenediamine H3C NH2 36. L - S H3C 1. Y-rro 36. L-Methioninol NH2 37. O 37. Tetrahydrofurfurylamine 38. 38. Amylamine H3C 1N1-N-N-2 NH2 39. Aminomethylcyclopropane 41. rN, N 41. 1-(2-Aminoethyl)piperazine CD FIGURE 20d) Patent Application Publication Dec. 25, 2003 Sheet 6 of 61 US 2003/0236225A1 42a. CH3 H2N CH3 CH3 42a. (+)-Bornylamine ' CH, CH3 43. tert-Octylamine H3CDuk CH3 44. t > ) 44. 1-Adamantanemethylamine 45. 2-Amino-1-propanol, d.l 46. 3-Phenyl-1-propylamine Cr NH2 47. 2,2-Diphenylamine NH2 48. r N 48. 1-(3-Aminopropyl)-2-pyrrolidinone ( - (tech) FIGURE 20e) Patent Application Publication Dec. 25, 2003 Sheet 7 of 61 US 2003/0236225A1 H2N F 49. 4-(Trifluoromethyl)benzylamine F 50. Nre, 50. 1-(2-Aminoehtyl)-pyrrolidine O si. -- HC1 O NH2 51. Veratryl amine 52. 1N1N1 N. 52. 5-Amino-1-pentanol H2N OH 53. 53. 2-(1-Cylcohexenyl)ethylamine O N N 54. CO 54. 5-Aminoquinoline NH2 H2N 55 55. 1-Aminomethyl-1-cylcohexanol, HCl Co 56. H. 56. 1-Aminopiperidine C FIGURE 20f) Patent Application Publication Dec. 25, 2003 Sheet 8 of 61 US 2003/0236225A1 57. F 57. 3-Fluorobenzylamine 59. (1S,2R)- C r 59. (1S,2R)-cis-1-Amino-2-indanol NH2 61. 1N1,N1OH 61. 4-Amino-1-butanol H2N 63. (S)- her rol 63. (S)-2-Amino-1-butanol NH2 66. NH2 CH, O 66. 2,4-Dimethoxybenzylamine CH3 68. H3C NH2 68. 1-(1-Naphthyl)ethylamine 69. O 69. 2-(2-Aminoethyoxy)ethanol HN1)-1N1 SoH 70. N s NH2 2N 70. 3-Amino-1,2,4-triazine N1 FIGURE 20g) Patent Application Publication Dec. 25, 2003 Sheet 9 of 61 US 2003/0236225A1 71. NH2 71. 2-Ethoxybenzylamine H3C ~5 72. NH2 72. 4-(3-Aminopropyl)morpholine C)O 73. NH2 O 73. 2-Amino-1-methoxypropane -- YoH 3 74a. CH3 74a. cis-(-)-Myrtanylamine re-r NH2 77a 77a. Cyclooctylamine Ore. H2N 78a 78a. 2-Adamantamine, HCl 79. 79. trans-2-Aminocyclohexanol, HCl OH N 80. 80. 3,Amino-5-phenyl pyrazole FIGURE 2(h) Patent Application Publication Dec. 25, 2003. Sheet 10 of 61 US 2003/0236225A1 82. 2,3-Dimethoxybenzylamine 83a. 83a. Noradamantamine, HCl () 84. 4-Amino-1-benzylpiperidine NH2 85. 85. 4-Methylcyclohexylamine HN 86. OH 86. (1R,2S)-1-Amino-2-indanol NH2 87 N 87. 3-Aminopyrazole 8 8. F 88. 4-Fluorobenzylamine NH2 90a. 90a, trans-2-Phenylcyclopropylamine, HCI O FIGURE 20i) Patent Application Publication Dec. 25, 2003. Sheet 11 of 61 US 2003/0236225A1 NH2 91. 1-(3-Aminopropyl)pipecoline O o-rrison 92. 2-Amino-1,3-propanediol NH2 93. OH OH H3C NH2 93. Thiomicamine S OH NH2 94. (R)-1-Amino-2-propanol H3C -N- 95. OH NH2 95. (S)-2-Amino-3-cyclohexyl-1-propanol, HCI 97. HO 97. 1-Amino-1-cyclopentane methanol O 98. NH2 OH H3C 98. (S)-Isoleucinol CH3 99. OH 99. 4-Clorophenylalaniol NH2 FIGURE 20) Patent Application Publication Dec. 25, 2003. Sheet 12 of 61 US 2003/0236225A1 100. CH3 NH2 100. l-Leucinol H3C ul-A-oh OH O1. NH2 OH 101. (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol 102. (S)-(+) luteOH 102. (S)-(+)-1-Amino-2-propanol H3C OH 103. CH3 H2N 103. 2-Amino-2-methyl-1,3-propanediol OH NH2 104. (d.,) HC1 O N OH 104. d, 1-Serine methyl ester, HCl O 105.a. H3 CH3 H3C 105a. (-)-Isopinocampheylamine NH2 107. H N 107. Histidinol FIGURE 20k) Patent Application Publication Dec. 25, 2003 Sheet 13 of 61 US 2003/0236225A1 108. N N1\ S-4 108. 2-Amino-5-cyclopropyl-1,3,4-thiadiaZol 109. CH3 H2N OH 109. 2-Amino-2-methyl-1-propanol H3C 111. an 1 NH 2 111. Allylamine 112. to-rrs, 112. 3-Amino-1,2-propanediol OH 115. - -,NH 115. Hexamethyleimine NH2 117. N S 17. 3-Aminorhodamine CH3 NH2 119. OH 119. (R)-(-)-2-Phenylglycinol 126. Methyl-3-aminocrotonate FIGURE 201) Patent Application Publication Dec. 25, 2003 Sheet 14 of 61 US 2003/0236225A1 29. cS 129. d, 1-Homocysteine, thiolactone, HCl NH2 137. 2-Amino-5trifluoromethyl-1,3,4-thiadiazol H2N 138. Racemic; "test" well H3C ~so 138. d, 1-2-Amino-1-butanol (test, making EMB) NH2 140. 140. 3-Etoxypropylamine HN1N1\o 1N CH3 141. her CH3 141. sec-Butylamine NH2 142. NH2 142. 2-Aminoheptane e-N-n-re. 3 143. CH3 H2N OH 143. 2-Amino-2-methyl-1-propanol H3C 144. NH2 144. (S)-1-Amino-2-(Methoxymethyl)pyrrolidine FIGURE 20m) Patent Application Publication Dec. 25, 2003. Sheet 15 of 61 US 2003/0236225A1 145a. NH2 145a, trans-l,2-Diaminocyclohexane NH2 147. O NH2 147. 3-Amino-2-methoxydibenzofuran O 148. *R OOH3 $-(N 148. 2-Amino-4-methoxybenzothiazole NH2 149. 149. 1-Aminohomopiperidine C) 150. CC H2 150. 2-Amino-3-hydroxypyridine OH 151. N 151. 1-Aminopyrrolidine, HCl NH2 152. CH3 HO 152. d, 1-2-Amino-1-pentanol NH2 154. OH 154. Ethanolamine H2N 1N1 FIGURE 2(n) Patent Application Publication Dec. 25, 2003 Sheet 16 of 61 US 2003/0236225A1 155. NH2 155. 3-Methylbenzylamine CH3 156. Hc1a1 N1\1\CH, o N- NH2 156. 3-(Dibutylamino)propylamine 157. HO CH3 NH2 157. Norephedrine, HCl 158. H2N O y O 158. Piperonylamine 159. O 159. 2-Methoxyethylamine HN1N1 NoH, 100. e-rrsch, 160. 1-Ethylpropylamine NH2 161. N S.N NH2 161. 1-(3-Aminopropyl)imidazol n-1N1 162. 162. 1-Aminoadamantamine t C 164. NH2 erro,O O 164. Dimethylaminomalonate, HCl O O FIGURE 200) Patent Application Publication Dec. 25, 2003 Sheet 17 of 61 US 2003/0236225A1 166. 166. Isopropylamine H3C CH3 167 it. 1. N1-a-NH2 167. 3-(Dimethylamino)propylamine H3C 169. cr" 169. 4-Fluorophenethylamine F 70. NH2 170. 2-(4-Aminophenyl)ethylamine 171. NH2 N 171. 3-Aminoisoxazole O 172. NH2 172. 1,2-Diaminopropane he-S- 2 173. D.L. H N NH2 O SCH 173. d, 1-Tryptophan methyl ester, HCl O 174. D- O 174. d-Aspartic acid, dimethyl ester, HCl NH2O 175. L- O CH3 hero- CH 3 175. l-Leucine ethyl ester, HCl NH2 FIGURE 20p) Patent Application Publication Dec. 25, 2003 Sheet 18 of 61 US 2003/0236225A1 176.Hics L- O O HN s 176. l-Methionine ethyl ester, HCl CH3 177. D.L O HC3 sore, 177. d.l-a-Amino-n-butyric acid methyl ester, HCI NH2 H3C 178. L- o? O H2N NO2 178.
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