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WO1994003467B1 - Antiretroviral enantiomeric nucleotide analogs - Google Patents

Antiretroviral enantiomeric nucleotide analogs

Info

Publication number
WO1994003467B1
WO1994003467B1 PCT/US1993/007360 US9307360W WO9403467B1 WO 1994003467 B1 WO1994003467 B1 WO 1994003467B1 US 9307360 W US9307360 W US 9307360W WO 9403467 B1 WO9403467 B1 WO 9403467B1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
enriched
och
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1993/007360
Other languages
French (fr)
Other versions
WO1994003467A2 (en
WO1994003467A3 (en
Filing date
Publication date
Priority claimed from US07/925,610 external-priority patent/US6057305A/en
Priority to US08/379,551 priority Critical patent/US6653296B1/en
Priority to EP93918659A priority patent/EP0654037B1/en
Priority to DE69324923T priority patent/DE69324923T2/en
Priority to JP1994505559A priority patent/JP3561272B6/en
Priority to CA002141589A priority patent/CA2141589C/en
Application filed filed Critical
Priority to DK93918659T priority patent/DK0654037T3/en
Priority to HK98113194.0A priority patent/HK1011998B/en
Publication of WO1994003467A2 publication Critical patent/WO1994003467A2/en
Publication of WO1994003467A3 publication Critical patent/WO1994003467A3/en
Publication of WO1994003467B1 publication Critical patent/WO1994003467B1/en
Anticipated expiration legal-status Critical
Priority to GR990401839T priority patent/GR3030754T3/en
Ceased legal-status Critical Current

Links

Abstract

Resolved enantiomers of formulae (IA) and (IB) wherein B is a purine or pyrimidine base or aza and/or deaza analogs thereof are useful in antiviral pharmaceutical compositions to treat retroviral infections.

Claims

- 96 -
AMENDED CLAIMS
[received by the International Bureau on 14 May 1994 (14.05.94); original claims 27 and 32 cancelled; original claims 30, 31 and 33 amended; new claims 67-69 added; remaining claims unchanged (4 pages)]
B- CH2CH- CH3
OCH2P(O) (OR)2 (NI)
followed by treating said derivative of formula VI with a halotrimethylsilane in an inert aprotic solvent.
24. The method of claim 23 wherein the alkali carbonate is cesium carbonate.
25. The method of claim 23 wherein the inert aprotic solvent is acetonitrile, dimethyiformamide or a halogenated hydrocarbon.
26. The method of claim 23 wherein the halotrimethylsilane is bromotrimethylsilane.
28. A compound of the formula:
Figure imgf000003_0001
wherein LvO is a leaving group, as a racemate or as the enriched or resolved enantiomers.
.97.
29. A compound of the formula:
Figure imgf000004_0001
II
wherein B is as defined in claim 1 or is a protected form thereof, as a racemate or as the enriched or resolved enantiomers.
30. An enriched or resolved enantiomer of a compound of the formula
B- CH2CH- CH3
I
OH πi
wherein B is a substituted or unsubstituted purine or pyrimidine moiety, an aza and/or deaza analogue thereof, or a protected form thereof.
31. A compound of the formula:
Figure imgf000004_0002
as the enriched or resolved R enantiomer. -98-
33. A compound of the formula:
* CH3 CH— CH2OCH2C6H5
OCH2Cj XIV
as the enriched or resolved R enantiomer.
34. A compound of the formula:
CH3 CH- CH2OCH2C6H5
OCH2P(O) (OR)2 XV
wherein R is independently alkyl (1-6C), aryl or aralkyl as a racemate or as the enriched or resolved enantiomers.
35. A compound of the formula:
CH3 CH— CH2OH
OCH2P(O) (OR)2 XVI
wherein R is alkyl (1-6C), aryl or aralkyl as a racemate or as the enriched or resolved enantiomers. - 99 -
65. A compound selected from the group consisting of 9- (R)-(2-Phosphononethoxypropyl)-2,6-diaminopurine and the 1,3-dideaza, 1-deaza, 3-deaza or 8-aza analogs thereof.
66. A method to synthesize the compounds of claim 1 wherein B is 2-amino purine substituted at the 6 position with alkylamino, dialkylamino, aralkylamino, heteroalkylamino or heterocyclic amino, comprising reacting the corresponding amine or heterocyclic amine with an alkyl (1-6C), aryl or aralkyl diester of 9-(R)-(2- phosphonomethoxypropyl)-2-amino-6-chloropurine.
67. A compound of the formula
B- CH2CH- CH3
I OH m
wherein B is a substituted or unsubstituted purine or pyrimidine moiety, an aza and/or deaza analogue thereof, or a protected form thereof, as a racemate or as the enriched or resolved enantiomers, provided however that B is not adenine, 8-azaadenine, 2-aminopurine, or adenine substituted at the 6 position with halogen, hydroxy, alkoxy, alkylamino, diallaylamino, mercapto, -NHNH2 or -NHOH.
68. The enantiomer of claim 30 wherein B is a substituted or unsubstituted purine moiety, an aga and /or deaza analogue thereof, or a protected form thereof.
69. The compound of claim 67 wherein B is a substituted or unsubstituted purine moiety, an aza and/or deaza analogue thereof, or a protected form thereof.
PCT/US1993/007360 1992-08-05 1993-08-04 Antiretroviral enantiomeric nucleotide analogs Ceased WO1994003467A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
HK98113194.0A HK1011998B (en) 1992-08-05 1993-08-04 Antiretroviral enantiomeric nucleotide analogs
EP93918659A EP0654037B1 (en) 1992-08-05 1993-08-04 Antiretroviral enantiomeric nucleotide analogs
DE69324923T DE69324923T2 (en) 1992-08-05 1993-08-04 Antiretroviral, enantiomeric nucleotide analogs
JP1994505559A JP3561272B6 (en) 1992-08-05 1993-08-04 Antiretroviral enantiomeric nucleotide analogues
CA002141589A CA2141589C (en) 1992-08-05 1993-08-04 Antiretroviral enantiomeric nucleotide analogs
US08/379,551 US6653296B1 (en) 1992-08-05 1993-08-04 Antiretroviral enantiomeric nucleotide analogs
DK93918659T DK0654037T3 (en) 1992-08-05 1993-08-04 Enantiomeric anti-retroviral nucleotide analogues
GR990401839T GR3030754T3 (en) 1992-08-05 1999-07-14 Antiretroviral enantiomeric nucleotide analogs.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/925,610 US6057305A (en) 1992-08-05 1992-08-05 Antiretroviral enantiomeric nucleotide analogs
US07/925,610 1992-08-05

Publications (3)

Publication Number Publication Date
WO1994003467A2 WO1994003467A2 (en) 1994-02-17
WO1994003467A3 WO1994003467A3 (en) 1994-06-23
WO1994003467B1 true WO1994003467B1 (en) 1994-07-21

Family

ID=25451994

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/007360 Ceased WO1994003467A2 (en) 1992-08-05 1993-08-04 Antiretroviral enantiomeric nucleotide analogs

Country Status (12)

Country Link
US (3) US6057305A (en)
EP (2) EP0897917A1 (en)
JP (2) JP4083691B2 (en)
AT (1) ATE179983T1 (en)
CA (2) CA2141589C (en)
CZ (2) CZ290797B6 (en)
DE (1) DE69324923T2 (en)
DK (1) DK0654037T3 (en)
ES (1) ES2131116T3 (en)
GR (1) GR3030754T3 (en)
SG (1) SG47761A1 (en)
WO (1) WO1994003467A2 (en)

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