US4927830A
Expired / Lapsed
US
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Acyclic pyrrolo[2,3-D]pyrimidine analogs as antiviral agents
Assignee: MICHIGAN A CONSTITUTIONAL Corp OF MICHIGAN, University of, Regents of
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Filing: 1988-04-08
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Granted: 1990-05-22
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Expires: 2008-04-08
Abstract
Abstract This invention relates to the use of acyclic substituted pyrrolo[2,3-d]pyrimidine nucleoside analogs in the treatment of viral infections. Such substituted compounds retain antiviral properties present in their parent compounds, yet exhibit significantly decreased levels of cytotoxicity, thereby having therapeutic potential as antiviral agents.
Inventors
- 👤 Leroy B. Townsend
- 👤 John C. Drach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:58
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
61 words
A compound selected from the group consisting of compounds of the following formula and pharmaceutically acceptable salts thereof: ##STR6## where R 1 is NH 2 or NHOH; R 2 is CSNH 2 , Cl, Br, I, F, 2-buten-1-yl, 5-(1-hydroxyethyl) or 5-(1-methoxyethyl); R 3 is H, NH 2 or Br; and R 4 is (1,3-dihydroxy2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-ethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxyl-(1,3-dihydroxy2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl.
Claim 2
Dependent Claim
61 words
A compound selected from the group consisting of compounds of the following formula and pharmaceutically acceptable salts thereof: ##STR6## where R 1 is NH 2 or NHOH; R 2 is CSNH 2 , Cl, Br, I, F, 2-buten-1-yl, 5-(1-hydroxyethyl) or 5-(1-methoxyethyl); R 3 is H, NH 2 or Br; and R 4 is (1,3-dihydroxy2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-ethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxyl-(1,3-dihydroxy2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl.
Claim 3
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is Cl, R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 4
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is Br, R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 5
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is I, R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 6
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is thiocarboxamide, R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 7
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is Cl, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 8
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is Br, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 9
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is I, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 10
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is thiocarboxamide, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 11
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is NH 2 , R 2 is thiocarboxamide, R 3 is H and R 4 is 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl.
Claim 12
Independent Claim
101 words
The method of treating animal cells infected with a mammalian infectious virus comprising the step of contacting said cells with a composition comprising a compound in an amount sufficient to provide a therapeutic effect on said animal cells, said compound being selected from the group consisting of a compound of the following formula and pharmaceutically acceptable salts thereof: ##STR7## where R 1 is NH 2 or NHOH; R 2 is CSNH 2 , Cl, Br, I, F, 2-butenl-yl, 5-(1-hydroxyethyl) or 5-(1-methoxyethyl); R 3 is H, NH 2 or Br; and R 4 is (1,3-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-ethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl.
Claim 13
Independent Claim
101 words
The method of treating animal cells infected with a mammalian infectious virus comprising the step of contacting said cells with a composition comprising a compound in an amount sufficient to provide a therapeutic effect on said animal cells, said compound being selected from the group consisting of a compound of the following formula and pharmaceutically acceptable salts thereof: ##STR7## where R 1 is NH 2 or NHOH; R 2 is CSNH 2 , Cl, Br, I, F, 2-butenl-yl, 5-(1-hydroxyethyl) or 5-(1-methoxyethyl); R 3 is H, NH 2 or Br; and R 4 is (1,3-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-ethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl.
Claim 14
Dependent Claim
11 words
The method of claim 11 wherein the virus is human cytomegalovirus.
Claim 15
Dependent Claim
14 words
The method of claim 11 wherein the virus is herpes simplex virus type 1.
Claim 16
Dependent Claim
11 words
The method of claim 11 wherein said cells are human cells.
Claim 17
Dependent Claim
27 words
The method of claim 11 wherein R 1 is NH 2 , R 2 is a halo group, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 18
Dependent Claim
27 words
The method of claim 11 wherein R 1 is NH 2 , R 2 is a halo group, R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 19
Dependent Claim
10 words
The method of claim 15 wherein R 2 is Cl.
Claim 20
Dependent Claim
10 words
The method of claim 15 wherein R 2 is Br.
Claim 21
Dependent Claim
9 words
The method of claim 16 wherein R 2 Cl.
Claim 22
Dependent Claim
10 words
The method of claim 16 wherein R 2 is Br.
Claim 23
Dependent Claim
10 words
The method of claim 16 wherein R 2 is I.
Claim 24
Dependent Claim
27 words
The method of claim 11 wherein R 1 is NH 2 , R 2 is CSNH 2 , R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 25
Dependent Claim
27 words
The method of claim 11 wherein R 1 is NH 2 , R 2 is CSNH 2 , R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 26
Dependent Claim
12 words
The method of claim 11 wherein R 3 is NH 2 .
Claim 27
Dependent Claim
10 words
The method of claim 11 wherein R 3 is Br.
Claim 28
Dependent Claim
13 words
The method of claim 11 wherein said step of contacting occurs in vivo.
References Cited (Backward Citations)
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