KR880002860A - Pyrimidine derivatives - Google Patents

Abstract

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Description

Pyrimidine derivatives

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Claims (21)

The following general formula (I) compound and its tautomer Wherein R ¹ is halogen, C _1-4 alkyl or halo- (C _1-4 alkyl) and R ² is hydrogen, hydroxy or acyloxy and R ³ and R ⁴ are each hydrogen or C _1-4 alkyl R ⁵ is aryl or aryloxy, X is oxygen or NH, Y is -CO-CH ₂ , -CH- (OH) -CH _2- , -CH ₂ -CH _2- , -S-,- SO- or -SO _2- . The compound of claim 1, wherein R ⁵ is aryl and Y is —CO—CH ₂ , —CH— (OH) —CH ₂ —, —CH ₂ —CH ₂ —, —SO—, or —SO ₂ —. The compound of claim 1 or 2, wherein R ¹ is C _1-4 alkyl. The compound of any of claims 1-3, wherein R ² is hydroxy or C _1-4 alkanoyloxy. The compound of any one of claims 1-4, wherein R ³ and R ⁴ are each hydrogen. The compound according to any one of claims 1 to 5, wherein R ⁵ is dihalophenyl, The compound according to any one of claims 1 to 6, wherein X is oxygen, 8. The compound of claim 1, wherein Y is —CO—CH ₂ —, —CO (OH) —CH ₂ —, —CH ₂ —CH ₂ —, or —SO ₂ —. 9. 9. The compound of claim 1, wherein R ¹ is ethyl, R ² is hydroxy or acetoxy, R ³ and R ⁴ are each trouble, R ⁵ is 2,6-dichlorophenyl, X is Oxygen and Y is -CO-CH ₂ -or -CH (OH) -CH _2- . The compound of claim 1, wherein 3'-0-acetyl-5 '[3- (2,6-dichlorofetyl) -2-oxopropyl] 2' 5'-dideoxy-5-ethyluridine, 5 '-[ 3-2,6-dichlorophenyl) -2 (RS) -hydroxypropyl] -2'5'-dideoxy-5-ethyluridine and especially 5 '-[3- (2,6-dichlorophenyl)- 2 oxopropyl] 2'5'-dideoxy-5-ethyluridine. 3'-O-acetyl-2'5'-dideoxy-5-ethyl-5 '-[3- (2,6-dimethylphenyl) -2-oxopropyl] uridine, 3' -O-acetyl-2 ',-5'-dideoxy-5-ethyl-5'-[3- (2-methylphenyl) -2-oxopropyl] uridine, 3'-0-acetyl-5 '-[ 3- (2-chlorophenyl) -2-oxopropyl] -2 ', 5'-dideoxy-5-ethyluridine, 3'-0-acetyl-2', 5 'dideoxy-5-ethyl-5 '-(2-oxo-3-phenylpropyl) uridine, 3'-0-acetyl-2'5'-dideoxy-5-ethyl-5'-[2-oxo-3 (RS) -phenylbutyl] Uridine, 2 ', 5'-dideoxy-5-ethyl-5'-(2-oxo-3-phenylpropyl) uridine, 2 ', 5'-dideoxy-5-ethyl-5'-[3 -(2-methylphenyl) -2-oxopropyl] -uridine, 2 ', 5'-dideoxy-5-ethyl-5'-[3- (2,6-dimethylphenyl) -2-oxopropyl] uri Dine, 5 '-[3- (2-chlorophenyl) -2-oxopropyl] -2', 5'-dideoxy-5-ethylwoodydine, 2 ', 5'-dideoxy-5-ethyl-5 '-[2-oxo-3 (RS) -phenylbutyl] uridine, 2', 5'-dideoxy-5-ethyl-5 '-[2 (RS) -hydroxy-3-phenylpropyl] uridine , 2 ', 5'-dideoxy-5-ethyl-5'-[2 (RS)- Idoxy-3- (2-methylphenyl) propyl] uridine, 5 '-[3- (2-chlorophenyl) -2 (RS) -hydroxypropyl] -2', 5'-dideoxy-5-ethyl Uridine, 2,5'-dideoxy-5-ethyl-5 '-[2 (RS) -hydroxy-3- (2,6-dimethylphenyl) propyl] uridine, 2', 5'-dideoxy -5-ethyl-5 '-(3-phenylpropyl) uridine and 5'-benzylsulfonyl-2', 5'-dideoxy-5-ethyluridine. 2. The compound of claim 1, wherein 2′5′-dedeoxy-5 ′-[3- (2,6-dimethylphenyl) -2-oxopropyl] uridine, 3′-O-acetyl-5 ′-[3 ( RS)-(2,4-dichlorophenoxy) -2-oxobutyl] -2'5'-dideoxy-5-ethyluridine, 5 '-[3 (RS)-(2,4-diclofen Oxy) -2-oxobutyl] -2'5'-deoxy-5-ethylwoodydine, 5 '-[3 (RS)-(2,4-dichlorophenoxy) -2 (RS) -hydroxybutyl ] -2 ', 5'-dideoxy-5-ethyluridine, 5'-benzylthio-2', 5'-dideoxy-5-ethyluridine, 5 '-(2-chlorobenzylthio) -2 ', 5'-dideoxy-5-ethyluridine, 5'-(2,4-dichlorobenzylthio) -2'-5'-dideoxy-5-ethyluridine, 5 '(2,6-dichloro Benzylthio) -2 ', 5'-dideoxy-5-ethyluridine, 5'-(2-chlorobenzylsulfonyl) -2 ', 5'-dideoxy-5-ethyluridine, 5'-( 2,4-dichlorobenzylsulfonyl) -2 ', 5'-dideoxy-5-ethyluridine and 5'-(2,6-dichlorobenzylsulfonyl) -2 ', 5'-dideoxy-5- Compound selected from ethyluridines. The following general formula (II) compounds and their tautomers, Wherein R ¹ is halogen, C _1-4 alkyl or halo (C _1-4 -alkyl), R ^{2 ′} is hydrogen or acyloxy, and R ³ and R ⁴ are each hydrogen or C _1-4 -alkyl And R ⁵ is aryl or aryloxy and X is oxygen or NH. The compound according to any one of claims 1 to 12, which is therapeutically active and particularly useful as an antivirally active compound. (a) To prepare a compound of formula (I) or a tautomer thereof, wherein R ² is hydrogen or acyloxy and Y is -CO-CH _2- , the compound of formula (II) or Catalytically hydrogenated; (b) to prepare a compound of formula (I) wherein R ² is hydrogen or acyloxy and Y is —CH (OH) —CH ₂ —; or a tautomer thereof, R ² is hydrogen or acyloxy, and Y Reducing the compound of formula (I) or a tautomer thereof, which is a -CO-CH _2- , with a metal hydride complex; (c) To prepare a compound of formula (I) wherein R ² is hydrogen or acyloxy and Y is -CH ₂ -CH ₂ -or a tautomer thereof, R ² is hydrogen or acyloxy, and Y is- CH (OH) -CH ₂ - in the general formula (ⅰ) compound or its substituted Sat hydroxy groups the hydrogen atoms of the auto bots or; (d) To prepare a compound of formula (I) or a tautomer thereof, wherein Y is -S-, a compound of formula (III) or a tautomer thereof at an elevated temperature with an alkali metal derivative of the compound of formula (IV) To react; (e) To prepare a compound of formula (I) wherein Y is -SO- or -SO ₂ -or a tautomer thereof, the compound of formula (I) wherein Y is -S- or a tautomer thereof Or; (f) it is characterized by the general formula (Ⅰ) to produce a compound or its tautomers, the R ² acyloxy of the general formula (Ⅰ) hwaham acyl ride a compound or a tautomeric the R ² hydroxy To prepare a compound of formula (I) according to claim 1 and a tautomer thereof. Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X are as defined in claim 1, R ^{2 ′} is hydrogen or acyloxy and R ⁷ is C _1-4 alkyl or aryl . The method of claim 15, wherein the process (a), (b), (c), (e) and / or (f) is carried out, A medicament, in particular an antiviral agent, comprising the compound according to any one of claims 1 to 12 and a therapeutically inert excipient. Use of a compound according to any one of claims 1 to 12 in the switching, in particular in the inhibition or prevention of viral infection. Use of a compound according to any one of claims 1 to 12 for the manufacture of a medicament for the inhibition or prevention of viral infection. A compound according to any one of claims 1 to 12, prepared by the process according to claim 15 or 16 or a chemically equivalent method thereof, Inventions described herein, and in particular related to the examples. ※ Note: The disclosure is based on the initial application.