Novel aminoalkyl glucosaminide 4-phosphate derivative
AssigneeDaiichi Sankyo Company, Limited
InventorsHiroyuki Kobayashi, Tatsuya Oka, Yoshiko Fukuyama
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Abstract
The present invention provides a novel compound or a pharmaceutically acceptable salt thereof which has a TLR4 activating effect and can be used as an immunostimulant or an adjuvant in vaccines or allergen immunotherapy. The present invention provides a compound represented by the general formula (I) or a pharmaceutically acceptable salt thereof. In this context, X, Y, Z and n in the formula (I) are each as defined herein.
Claims24
A compound represented by the general formula (I):
- wherein
- X represents an oxygen atom or CH2,
- Y represents CH2 or C═O,
- Z represents a halogen atom or OR1,
- R1 represents a hydrogen atom or the following formula (II):
- wherein
- R2 represents a hydrogen atom or a carboxy group,
- R3 represents a hydrogen atom, a hydroxy group, or an acetylamino group,
- R4 represents a hydrogen atom or the following formula (III):
- R5 represents a hydrogen atom or a phosphoric acid group, and
- R6 represents a hydroxymethyl group, a methyl phosphate group, a carboxy group, or a (1S)-1,2-dihydroxyethyl group, and
- n represents 0 or 1,
- * is the point of attachment in formula (I),
- or a pharmaceutically acceptable salt thereof,
- with the proviso that a compound is excluded wherein X represents an oxygen atom, n represents 0, Z represents OR1, and R1 represents a hydrogen atom.
A compound selected from the following group:
- (3R)-3-{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-4-({3-O-[(3R)-3-(decanoyloxy)tetradecanoyl]-2-{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-2-deoxy-6-O-(3-deoxy-α-D-manno-oct-2-ulopyranonosyl)-4-O-phosphono-β-D-glucopyranosyl}oxy)butanoic acid,
- (2S)-2-{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-3-{[3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2-+4)-3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2-+6)-3-O-[(3R)-3-(decanoyloxy)tetradecanoyl]-2-{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-2-deoxy-4-O-phosphono-β-D-glucopyranosyl]oxy}propanoic acid,
- (2S)-2-{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-3-({3-O-[(3R)-3-(decanoyloxy)tetradecanoyl]-2-{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-2-deoxy-6-β-D-glucopyranuronosyl-4-O-phosphono-β-D-glucopyranosyl}oxy)propanoic acid,
- 6,10-anhydro-8-O-[(3R)-3-(decanoyloxy)tetradecanoyl]-3,7-bis{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-2,3,4,5,7-pentadeoxy-11-O-(3-deoxy-α-D-manno-oct-2-ulopyranonosyl)-9-O-phosphono-D-erythro-L-galacto-undecanoic acid, and
- 5,9-anhydro-7-O-[(3R)-3-(decanoyloxy)tetradecanoyl]-2,6-bis{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-2,3,4,6-tetradeoxy-10-O-(3-deoxy-α-D-manno-oct-2-ulopyranonosyl)-8-O-phosphono-D-erythro-L-galacto-decanoic acid,
- or a pharmaceutically acceptable salt thereof.
(3R)-3-{[(3R)-3-(Decanoyloxy)tetradecanoyl]amino}-4-({3-O-[(3R)-3-(decanoyloxy)tetradecanoyl]-2-{[(3R)-3-(decanoyloxy)tetradecanoyl]amino}-2-deoxy-6-O-(3-deoxy-α-D-manno-oct-2-ulopyranonosyl)-4-O-phosphono-β-D-glucopyranosyl}oxy)butanoic acid or a pharmaceutically acceptable salt thereof.
(canceled)
Dependencies are inferred from the claim text.