EP0057548A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
7-Beta-D-arabinofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-4-amine 5'-phosphate compounds useful as antiviral agents, pharmaceutical compositions containing the compounds, and processes for producing the compounds
Assignee: Warner Lambert Co LLC
•
Filing: 1982-01-25
•
Granted: —
•
Expires: 2002-01-25
Abstract
Abstract 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidine, its hydroxy, amino and sulfhydryl derivatives, corresponding esters and non-toxic pharmaceutically acceptable salts are disclosed. Such compounds may be produced by arabinofura- nosylation of the requisite heterocyclic compound, with 2,3,5-tri-O-benzyl-a-D-arabinofuranosyl halide and further reaction to obtain the desired compound. These water-soluble compounds are resistant to adenosine deaminase and exhibit antiviral activity.
Inventors
- 👤 Philip Daniel Cook
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 23:28
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/14; A; A61; A61P; A61P31/00; A61P31/12
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
110 words
CLAIMS (for all designated States other than Austria): 1. A 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d] pyrimidine compound having the following general formula: or a tautomer thereof, or a pharmaceutically acceptable salt thereof, wherein X is NH 2 , OH or SH ; Y is H or NH 2 ; R is H or an acyl radical containing from 2 to 6 carbon atoms ; and R 1 is H, an acyl radical containing from 2 to 6 carbon atoms, or a phosphate group; with the provisos that, when Y is NH 2 , X is NH 2 or OH ; and, when all of Y, R and R 1 are hydrogen, X is SH.
Claim 2
Dependent Claim
16 words
A compound according to Claim 1, designated 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4- amine 5'-phosphate or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
15 words
A compound according to Claim 1, designated 7-β-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-one .5'-phosphate or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
15 words
A compound according to Claim 1, designated 7-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-7H-pyrrolo [2,3-d]pyrimidin-4-amine or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
15 words
A compound according to Claim 1, designated 7-B-D-arabinofuranosyl-3, 7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-thione or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
10 words
The compound designated 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidine or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
14 words
A compound according to Claim 1, designated 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2,4-diamine or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
15 words
A compound according to Claim 1, designated 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2,4-diamine 5'-phosphate or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
14 words
A compound according to Claim 1, desingated 2-amino-7-β-D-arabinofuranosyl-3,7-dihydro-pyrrolo-[2,3-d]pyrimidin-4-one or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
15 words
A compound according to Claim 1, designated 2-amino-7-P-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo-[2,3-d]pyrimidin-4-one 5'-phosphate or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
21 words
A pharmaceutical composition comprising a compound according to any one of Claims 1 to 10 and a pharmaceutically acceptable carrier therefor.
Claim 12
Dependent Claim
58 words
A process for producing a compound having the following general formula:- wherein Z is a hydrogen atom or a methylmercapto group and Bz represents a benzyl radical, which process comprises treating 4-chloro-7H-pyrrolo[2,3-d]pyrimidine or the corresponding 2-methylmercapto compound with sodium hydride in a polar solvent to form an anion having the formula: and β-D-arabinofuranosylating that anion with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride.
Claim 13
Dependent Claim
4 words
CLAIMS (for Austria alone):
Claim 14
Dependent Claim
58 words
A process for producing a compound having the following general formula:'- herein Z is a hydrogen atom or a methylmercapto group and Bz represents a benzyl radical, which process comprises treating 4-chloro-7H-pyrrolo-[2,3-d]pyrimidine or the corresponding 2-methylmercapto compound with sodium hydride in a polar solvent to form an anion having the formula: and β-D-arabinofuranosylating that anion with 2,3,5-tri-0-benzyl-a-D-arabinofuranosyl chloride.
Claim 15
Dependent Claim
72 words
A process for producing a component having the following general formula:- which process comprises converting the compound produced in accordance with the process of Claim 1 to the compound having the following formula:- by (1) treatment at an elevated temperature with ammonia or (2) treatment with excess hydrazine to produce the 4-hydrazine compound followed by hydrogenolysis; and removing the three benzyl blocking groups of the 4-amino compound to give the desired compound.
Claim 16
Dependent Claim
40 words
A process for producing a compound having the following formula:- which comprises subjecting the corresponding 5 1- OH compound, produced in accordance with the process of Claim 2, to treatment with a phosphorylating agent, for example phosphoryl chloride in triethylphosphate.
Claim 17
Dependent Claim
29 words
A process for producing a compound having the following formula:- which comprises treating the corresponding 4-amino compound, produced in accordance with the process of Claim 3, with sodium nitrite.
Claim 18
Dependent Claim
48 words
A process for producing a compound having the following formula:- which comprises appropriately treating the corresponding 4-amino, 5'-OH compound, produced in accordance with the process of Claim 2, for example with sodium nitrite, to produce 3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one and phosphorylating the latter at the 5'-position to produce the desired compound.
Claim 19
Dependent Claim
46 words
- A process for producing a compound having the following formula:- which comprises converting 7-β-D-arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-4-amine produced in accordance with the process of Claim 2, to the corresponding 7-β-D-arabinofuranosyl-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-one, and converting the 4-one group of the latter compound to a 4-thione group to give the desired compound.
Claim 20
Dependent Claim
30 words
A process for producing a compound having the following formula:- which canprises treating the compound produced by the process of Claim 6 with Raney nickel to produce the desired compound.
Claim 21
Dependent Claim
34 words
A process for producing a compound having the following formula:- which comprises acylating, for example with acetic anhydride, 7-β-D-arabinofuranosyl-7H-pyrrolo [2,3-d]pyrimidine-4-amine produced in accordance with the process of Claim 2, to give the desired compound.
Claim 22
Dependent Claim
35 words
A process for producing a compound having the following formula:- which comprises subjecting to hydrogenolysis a compound having the first formula shown in Claim 1 and produced in accordance with the process of Claim 1.
Claim 23
Dependent Claim
56 words
A process for producing a compound having the following formula:- which comprises oxidising the compound 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3,-dJpyrimidine produced in accordance with the process of Claim 1, to give the corresponding 2-methylsulfonyl compound which is reacted sequentially with sodium allyloxide and liquid ammonia and deblocked by hydrogenation in the presence of a catalyst to give the desired compound.
Claim 24
Dependent Claim
31 words
A process for producing a compound having the following formula:- which comprises phosphorylating, for example with phosphoryl chloride and triethyl phosphate, the compound produced by the process according to Claim 10.
Claim 25
Dependent Claim
46 words
A process for producing a compound having the following formula:- which comprises oxidising the compound 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine produced in accordance with the process of Claim 1, to give the corresponding 2-methylsulfonyl compound which is sequentially treated with hydrazine and Raney nickel to give the desired 2,4-diamine compound.
Claim 26
Dependent Claim
42 words
A process for producing a compound having the following general formula:- which comprises phosphorylating, for example with triethyl phosphate and phosphoryl chloride, the compound having the structural formula shown in Claim 12 and produced in accordance with the process of Claim 12.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.