US4968686A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Acyclic pyrrolo [2,3-d]pyrimidine analogs as antiviral agents
Assignee: University of Michigan (System)
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Filing: 1989-06-21
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Granted: 1990-11-06
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Expires: 2009-06-21
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 G. Drach
- 👤 Charles Shipman, Jr.
- 👤 Jeffrey S. Pudlo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 00:28
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
63 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 , NHOH, OH or H; 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-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl.
Claim 2
Dependent Claim
63 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 , NHOH, OH or H; 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-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-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
Dependent Claim
23 words
The compound of claim 1 wherein R 1 is OH, R 2 is Cl, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 13
Dependent Claim
23 words
The compound of claim 1 wherein R 1 is NHOH, R 2 is Cl, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 14
Dependent Claim
23 words
The compound of claim 1 wherein R 1 is OH, R 2 is Br, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 15
Dependent Claim
23 words
The compound of claim 1 wherein R 1 is NHOH, R 2 is Br, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 16
Dependent Claim
23 words
The compound of claim 1 wherein R 1 is NHOH, R 2 is I, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 17
Dependent Claim
27 words
The compound of claim 1 wherein R 1 is wherein R 1 is OH, R 2 is I, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 18
Dependent Claim
12 words
The compound of claim 1 wherein R 3 is NH 2 .
Claim 19
Dependent Claim
10 words
The compound of claim 1 wherein R 3 is Br.
Claim 20
Independent Claim
123 words
A method of treating mammalian cells infected with a mammalian infectious virus selected from the group consisting of human cytomegalovirus and herpes simplex virus, the method comprising the step of contacting said cells with a composition comprising a therapeutically effective amount of a compound selected from the group consisting of compounds of the following formula or a pharmaceutically acceptable salt thereof: ##STR7## where R 1 is NH 2 , NHOH, OH or H; 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-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl, wherein said contacting of said cells comprises in vivo administration of said composition to the infected mammal.
Claim 21
Independent Claim
123 words
A method of treating mammalian cells infected with a mammalian infectious virus selected from the group consisting of human cytomegalovirus and herpes simplex virus, the method comprising the step of contacting said cells with a composition comprising a therapeutically effective amount of a compound selected from the group consisting of compounds of the following formula or a pharmaceutically acceptable salt thereof: ##STR7## where R 1 is NH 2 , NHOH, OH or H; 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-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl, wherein said contacting of said cells comprises in vivo administration of said composition to the infected mammal.
Claim 22
Dependent Claim
20 words
The method of claim 19 wherein said contacting of said cells comprises invivo administration of said composition to a mammal.
Claim 23
Dependent Claim
11 words
The method of claim 19 wherein said cells are human cells.
Claim 24
Dependent Claim
11 words
The method of claim 20 wherein said mammal is a human.
Claim 25
Dependent Claim
11 words
The method of claim 19 wherein the virus is human cytomegalovirus.
Claim 26
Dependent Claim
14 words
The method of claim 19 wherein the virus is herpes simplex virus type 1.
Claim 27
Dependent Claim
27 words
The method of claim 19 wherein R 1 is NH 2 , R 2 is a halogen group, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 28
Dependent Claim
25 words
The method of claim 19 wherein R 1 is NHOH, R 2 is a halogen group, R 3 is H and R 4 is (1,3-dihydroxy-2-propoxy)methyl.
Claim 29
Dependent Claim
27 words
The method of claim 19 wherein R 1 is NH 2 , R 2 is a halogen group, R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 30
Dependent Claim
10 words
The method of claim 25 wherein R 2 is Cl.
Claim 31
Dependent Claim
10 words
The method of claim 25 wherein R 2 is Br.
Claim 32
Dependent Claim
10 words
The method of claim 25 wherein R 2 is I.
Claim 33
Dependent Claim
10 words
The method of claim 26 wherein R 2 is Cl.
Claim 34
Dependent Claim
10 words
The method of claim 26 wherein R 2 is Br.
Claim 35
Dependent Claim
10 words
The method of claim 26 wherein R 2 is I.
Claim 36
Dependent Claim
10 words
The method of claim 27 wherein R 2 is Cl.
Claim 37
Dependent Claim
10 words
The method of claim 27 wherein R 2 is Br.
Claim 38
Dependent Claim
10 words
The method of claim 27 wherein R 2 is I.
Claim 39
Dependent Claim
27 words
The method of claim 19 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 40
Dependent Claim
27 words
The method of claim 19 wherein R 1 is NH 2 , R 2 is CSNH 2 , R 3 is H and R 4 is (2-hydroxyethoxy)methyl.
Claim 41
Dependent Claim
12 words
The method of claim 19 wherein R 3 is NH 2 .
Claim 42
Dependent Claim
10 words
The method of claim 19 wherein R 3 is Br.
Claim 43
Dependent Claim
70 words
A composition comprising a compound selected from the group consisting of compounds of the following formula and pharmaceutically acceptable salts thereof: ##STR8## where R 1 is NH 2 , NHOH, OH or H; R 2 CSNH 2 , Cl, Br, I, F, 2-buten-1-yl, 5-(1-hydroxyethyl) or 5-(1-methoxyethoxy); R 3 is H, NH 2 or Br; and R 4 is (1,3-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl; and a pharmaceutically acceptable carrier.
Claim 44
Dependent Claim
70 words
A composition comprising a compound selected from the group consisting of compounds of the following formula and pharmaceutically acceptable salts thereof: ##STR8## where R 1 is NH 2 , NHOH, OH or H; R 2 CSNH 2 , Cl, Br, I, F, 2-buten-1-yl, 5-(1-hydroxyethyl) or 5-(1-methoxyethoxy); R 3 is H, NH 2 or Br; and R 4 is (1,3-dihydroxy-2-propoxy)methyl, (2-hydroxyethoxy)methyl, (2-acetoxyethoxy)methyl, 2-hydroxy-1-(1,3-dihydroxy-2-propoxy)ethyl, (2-phosphonylmethoxy)ethyl or 3-hydroxy-2-phosphonylmethoxypropyl; and a pharmaceutically acceptable carrier.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-11-05 | 1994-05-07 | 1994-11-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-11-05 | 1998-05-07 | 1998-11-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-11-05 | 2002-05-07 | 2002-11-06 | $7700.00 | Window Closed / Lapsed |