Claims
- 1. A compound of the Formula I:
- 2. The compound according to claim 1, wherein:
R1 and R2 are each independently saturated or unsaturated straight or branched substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted 3 to 8 membered cycloalkyl, substituted or unsubstituted 5 to 16 membered aryl, substituted or unsubstituted 5 to 10 membered arylalkyl, substituted or unsubstituted4 to 12 membered heterocycloalkyl or heteroaryl group having at least one oxygen, sulfur, or nitrogen atom within the ring, wherein, if present, the substituent is least one C1-C4 alkyl, hydroxy, halide, methoxy, ethoxy, carboxylic acid, ester, amine, or C1-C4 alkylamine; R3 is hydrogen, saturated or unsaturated straight or branched substituted or unsubstituted alkyl C1-C8 alkyl, substituted or unsubstituted 3 to 8 membered cycloalkyl, substituted or unsubstituted 5 to 16 membered aryl, substituted or unsubstituted 5 to 10 membered arylalkyl, substituted or unsubstituted 4 to 12 membered heterocycloalkyl or heteroaryl having at least one oxygen, sulfur, or nitrogen atom within the ring, wherein, if present, the substituent, is at least one hydroxy, fluoride, chloride, bromine, C1-C4 alkoxy, C1-C4 sulfide, C1-C4 sulfonyl, nitro, carboxylic acid, ester, amine, or C1-C4 alkylamine; R4, R4′, R8, and R8′ each independently is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, amine, C1-C4 alkylamine, carboxylic acid, ester, C1-C4 amide, halide, hydroxy, nitro, C1-C4 sulfide, C1-C4 sulfonyl, or sulfonamide; X is a bond, straight chain or branched substituted or unsubstituted C1-C4 alkyl, —(C1-C4 alkyl)N—, —(C1-C4 alkyl)O—, carbonyl, or sulfur; Y is nitrogen, phosphorus, oxygen, or sulfur; wherein, if Y is oxygen or sulfur, R2 is not present; and n is from 0 to about 1.
- 3. The compound according to claim 1, wherein:
X is a bond, methylene, or ethylene; Y is nitrogen, phosphorus, oxygen, or sulfur; wherein, if Y is oxygen or sulfur, R2 is not present; and n is 1.
- 4. The compound according to claim 1, wherein:
R3 is a substituted or unsubstituted phenyl, substituted or unsubstituted pyrrolidinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzodioxanyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenylphenolyl, wherein, if present, the substituent is at least one C1-C4 alkyl, C1-C4 alkoxy, C1-C4 sulfide, C1-C4 sulfonyl, nitro, fluoride, chloride, or bromide; X is a methylene; Y is nitrogen, phosphorus, oxygen, or sulfur; wherein, if Y is oxygen or sulfur, R2 is not present; and n is 1.
- 5. The compound according to claim 1, wherein at least one of R1, R2, or R3 is a benzimidazole.
- 6. The compound according to claim 5, wherein X is a bond or methylene, R3 is a 2-benzimidazole, and at least one of R1 or R2 is a 2-benzimidazole or 2-methylenebenzimidazole.
- 7. The compound according to claim 1, wherein the compound of Formula I is an enantiomer or diastereomer.
- 8. The compound according to claim 1, wherein R4′ and R8′ are hydrogen, methyl, methyl ester, ethyl ester, C1-C2 amide, carboxylic acid, methoxy, or sulfonamide.
- 9. The compound according to claim 1, wherein R4′ and R8′ are both hydrogen.
- 10. The compound according to claim 1, wherein R4, R4′, R8, and R8′ are all hydrogen.
- 11. The compound according to claim 1, wherein at least one of R4, R4′, R8, or R8′ is not hydrogen.
- 12. The compound according to claim 1, wherein at least two of R4, R4′, R8, and R8′ are not hydrogen.
- 13. The compound according to claim 1, wherein at least three of R4, R4′, R8, and R8′ are not hydrogen.
- 14. The compound according to claim 1, wherein at least one of Z2 and Z4 is nitrogen.
- 15. The compound according to claim 1, wherein both of Z2 and Z4 are nitrogen.
- 16. The compound according to claim 1, wherein Z4 is nitrogen.
- 17. A compound of the Formula II:
- 18. The compound according to claim 17, wherein
R1 and R2 are each independently: C1-C8 saturated or unsaturated straight or branched substituted or unsubstituted alkyl, substituted or unsubstituted 3 to 8 membered cycloalkyl, substituted or unsubstituted 5 to 16 membered aryl, substituted or unsubstituted 5 to 10 membered arylalkyl,4 to 12 membered heterocycloalkyl or heteroaryl with at least one oxygen, sulfur, or nitrogen atom within the ring, wherein, if present, the substituent is at least one hydroxy, halide, methoxy, ethoxy, carboxylic acid, ester, amine, or alkylamine.
- 19. The compound according to claim 16, wherein
R3 is C1-C4 straight chain or branched alkyl, substituted or unsubstituted 3 to 6 membered cycloalkyl, substituted or unsubstituted 5 to 12 membered aryl, substituted or unsubstituted 5 to 12 membered arylalkyl, or 4 to 12 membered heterocycloalkyl or heteroaryl with at least one oxygen, sulfur, or nitrogen atom within the ring, wherein, if present, the substituent is at least one hydroxy, halide, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 sulfide, C1-C4 sulfonyl, nitro, carboxylic acid, ester, amine, or C1-C4 alkylamine.
- 20. The compound according to claim 17, wherein
R4, R4′, R8, and R8′ are each independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, amine, C1-C4 alkylamine, C1-C4 amide, carboxylic acid, ester, halide, hydroxy, nitro, C1-C4 sulfide, C1-C4 sulfonyl, or sulfonamide.
- 21. The compound according to claim 17, wherein at least one of R1, R2, or R3 is a benzimidazole.
- 22. The compound according to claim 17, wherein R3 is a 2-benzimidazole, and at least one of R1 or R2 is a 2-benzimidazole or 2-methylene benzimidazole.
- 23. The compound according to claim 17, wherein the compound of Formula II is an enantiomer or diastereomer.
- 24. The compound according to claim 17, wherein R4, R4′, R8, and R8′ are hydrogen.
- 25. The compound according to claim 17, wherein at least one of R4, R4′, R8, or R8′ is not hydrogen.
- 26. The compound according to claim 17, wherein at least one of Z2 and Z4 is nitrogen.
- 27. The compound according to claim 17, wherein both of Z2 and Z4 are nitrogen.
- 28. The compound according to claim 17, wherein Z4 is nitrogen.
- 29. A compound of the Formula III:
- 30. The compound according to claim 29, wherein:
R1, and R2 are each independently saturated or unsaturated straight or branched substituted or unsubstituted C1-C11 alkyl, C1-C12 alkoxy, substituted or unsubstituted C1-C11 alkylamino, substituted or unsubstituted 3 to 10 membered cycloalkyl, substituted or unsubstituted 3 to 10 membered heterocycloalkyl, substituted or unsubstituted 5 to 12 membered aryl, substituted or unsubstituted 5 to 12 membered arylalkyl, substituted or unsubstituted 4 to 13 membered heteroaryl, alkanoyl, or imide, wherein, if present, the substituent is at least one C1-C4 alkyl, cyano, fluoride, chloride, bromide, hydroxy, nitro, or thiol.
- 31. The compound according to claim 29, wherein:
R4, R4′, R5, R5′, R8, R8′, R9, and R9′ are each independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, amine, C1-C4 alkylamine, C1-C4 amide, carboxylic acid, ester, halide, hydroxy, nitro, C1-C4 sulfide, C1-C4 sulfonyl, or sulfonamide.
- 32. The compound according to claim 29, wherein:
R6 is a saturated or unsaturated straight or branched substituted or unsubstituted C1-C8 alkyl, C1 -C4 alkoxy, substituted or unsubstituted C2-C6 alkylamino, substituted or unsubstituted 3 to 6 membered cycloalkyl, substituted or unsubstituted 4 to 5 membered heterocycloalkyl having at least one oxygen, nitrogen, or sulfur atom within the ring, substituted or unsubstituted 5 to 16 membered aryl, substituted or unsubstituted 5 to 10 membered arylalkyl, substituted or unsubstituted 4 to 6 membered heteroaryl having at least one oxygen, nitrogen, or sulfur atom in the ring, C1-C4 alkanoyl, or imide, wherein, if present, the substituent is at least one C1-C4 alkyl, cyano, fluoride, chloride, bromide, hydroxy, nitro, or thiol.
- 33. The compound according to claim 29, wherein:
R1 and R2 are each independently hydrogen, methyl, ethyl, propyl, isopropyl, sec-butyl, 3-methylbutyl, 2-methyl-2-propenyl, 2-propynyl, pentyl, hexyl, 2-butylyl, 2-hydroxy-2-(4-hydroxyphenyl)ethyl, 2-(2-pyridinyl)ethyl, 2-hydroxy-2-(3,4-dihydroxyphenyl)ethyl, 3-pyridinylmethyl, 2,5-difluorobenzyl, 4-trifluoromethoxyphenylmethyl, 3-methoxypropyl, 2-hydroxyethyl, 4-phenylbutyl, 2-phosphonatethyl, 3-(2-methyl)ethoxypropyl, 2-(2-thiophenyl)ethyl, N-benzyl-4-piperidinyl, 3-(1-pyrrolidinyl)propyl, 2-(N,N-diethyl)ethyl, tetrahydrofuranylmethyl, cyclopentyl, or cyclohexyl.
- 34. The compound according to claim 29, wherein R6 is hydrogen.
- 35. The compound according to claim 29, wherein the compound of Formula III is an enantiomer or diastereomer.
- 36. The compound according to claim 29, wherein R4′, R5′, R8′, and R9′ are hydrogen.
- 37. The compound according to claim 29, wherein at least one of R4, R4′, R8, and R8′ is not hydrogen.
- 38. The compound according to claim 29, wherein at least two of R4, R4′, R8′, and R8′ are not hydrogen.
- 39. The compound according to claim 29, wherein at least one of R5, R5′, R9, and R9′ is not hydrogen.
- 40. The compound according to claim 29, wherein at least one of Z2 and Z4 is nitrogen.
- 41. The compound according to claim 29, wherein both of Z2 and Z4 are nitrogen.
- 42. The compound according to claim 29, wherein Z4 is nitrogen.
- 43. The compound according to claim 29 having Formula V:
- 44. A compound of the Formula IV:
- 45. The compound according to claim 44, wherein:
—R1—N—R2— form a saturated or unsaturated, substituted or unsubstituted 3 to 7 membered cycloalkyl, substituted or unsubstituted 3 to 7 membered heterocycloalkyl, substituted or unsubstituted 3 to 7 membered heteroaryl, wherein, if present, the substituent is at least one substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C1-C4 alkoxy, C1-C4 esters, hydroxy, fluoride, chloride, bromide, substituted or unsubstituted 3 to 8 membered aryl, substituted or unsubstituted 4 to 6 membered cycloalkyl, substituted or unsubstituted 3 to 8 membered heterocycloalkyl, carbonyl, or nitro.
- 46. The compound according to claim 44, wherein:
R4, R4′, R5, R5′, R6, R8, R8′, R9, and R9′ are each independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, amine, C1-C4 alkylamine, C1-C4 amide, carboxylic acid, ester, halide, hydroxy, nitro, C1-C4 sulfide, C1-C4 sulfonyl, or sulfonamide.
- 47. The compound according to claim 44, wherein R4′, R5′, R8′, and R9′ are hydrogen.
- 48. The compound according to claim 44 wherein at least one of R4, R4′, R8, and R8′ is not hydrogen.
- 49. The compound according to claim 44, wherein R5, R5′, R9, and R9′ are hydrogen.
- 50. The compound according to claim 44, wherein at least one of R5, R5′, R9, and R9′ is not hydrogen.
- 51. The compound according to claim 44, wherein R6 is hydrogen.
- 52. The compound according to claim 44, wherein:
—R1—N—R2— form a 5, 6, or 8 membered ring; and R4, R4′, R5, R5′, R6, R8, R8′, R9, and R9 are each independently are hydrogen C1-C2 alkyl, C1-C2 alkoxy, amine, C1-C2 alkylamine, fluoride, chloride, bromide, hydroxy, nitro, C1-C2 sulfide, or C1-C2 sulfonyl.
- 53. The compound according to claim 44, wherein the 5, 6, or 8 membered ring formed by —R1—N—R2— is a pyrrolidinyl, piperidinyl, pyrrolyl, imidazolyl, pyridinyl, pyrimidinyl, piperazinyl, quinolinyl, acridinyl, thiazole, morpholinyl, or unsubstituted or substituted phenyl wherein, if present, the substituent, if present, is at least one methyl, ethyl, ester, methanol, 2-ethanol, or aldehyde.
- 54. The compound according to claim 44, wherein the compound of Formula IV is an enantiomer or diastereomer.
- 55. The compound according to claim 44, wherein at least one of Z2 and Z4 is nitrogen.
- 56. The compound according to claim 44, wherein both of Z2 and Z4 are nitrogen.
- 57. The compound according to claim 44, wherein Z4 is nitrogen.
- 58. The compound according to claim 44 having Formula VI:
- 59. A pharmaceutical composition comprising the compound according to claim 1 and a pharmaceutically acceptable carrier.
- 60. A pharmaceutical composition comprising the compound according to claim 17 and a pharmaceutically acceptable carrier.
- 61. A pharmaceutical composition comprising the compound according to claim 29 and a pharmaceutically acceptable carrier.
- 62. A pharmaceutical composition comprising the compound according to claim 43 and a pharmaceutically acceptable carrier.
- 63. A pharmaceutical composition comprising the compound according to claim 44 and a pharmaceutically acceptable carrier.
- 64. A pharmaceutical composition comprising the compound according to claim 58 and a pharmaceutically acceptable carrier.
- 65. A method of treating, preventing, or ameliorating one or more symptoms associated with a respiratory syncytial virus (RSV) infection in a mammal comprising administering to the mammal a therapeutically or prophylactically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.
- 66. The method of treating, preventing, or ameliorating a viral infection according to claim 65, wherein the compound is administered orally, parenterally, transdermally, or mucosally.
- 67. The method of treating, preventing, or ameliorating a viral infection according to claim 65, wherein the compound is administered in an amount from about 10 mg/kg/day to about 15 mg/kg/day.
- 68. The method of treating, preventing, or ameliorating a viral infection according to claim 65, wherein the mammal is a human subject.
- 69. The method of treating, preventing, or ameliorating a viral infection according to claim 68, wherein the human subject is a human infant.
- 70. A method of inhibiting membrane fusion associated events characteristic of a viral infection in a mammal comprising administering the compound of claim 1 and a pharmaceutically acceptable carrier.
- 71. A method of treating, preventing, or ameliorating one or more symptoms associated with a HPV infection in a mammal comprising administering to the mammal a therapeutically or prophylactically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.
- 72. A method of treating, preventing, or ameliorating one or more symptoms associated with a hMPV infection in a mammal comprising administering to the mammal a therapeutically or prophylactically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.
Parent Case Info
[0001] This application claims the benefit of U.S. Provisional Application No. 60/424,940 filed Nov. 8, 2002, which is incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60424940 |
Nov 2002 |
US |