US4287188A
Expired / Lapsed
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Purine derivatives
Assignee: SmithKline Beecham Corp
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Filing: 1978-06-29
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Granted: 1981-09-01
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Expires: 1998-06-29
Abstract
Abstract 9-(2-Hydroxyethoxymethyl) (and related) derivatives of certain 6-, and 2,6-substituted purines have been discovered to have potent anti-viral activities. Novel compounds and their pharamceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-Hydroxyethoxymethyl)guanine and 2-amino-9-(2-hydroxyethoxymethyl) adenine are examples of especially active compounds of this invention. Also preferred because of its high oral absorption is the phosphate and especially the monophosphate of 9-(2-hydroxyethoxymethyl)guanine as well as pharmaceutically acceptable salts thereof.
Inventors
- 👤 Howard J. Schaeffer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 01:14
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616
Claims Analysis
Total Claims: 72
Claim 1
Independent Claim
9 words
9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
9 words
9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
3 words
9-(2-hydroxethoxymethyl) guanine monophosphate.
Claim 4
Dependent Claim
3 words
9-(2-hydroxethoxymethyl) guanine monophosphate.
Claim 5
Dependent Claim
23 words
A compound of the formula ##STR14## where Z is a pharmaceutically acceptable cation and W is H or a a pharmaceutically acceptable cation.
Claim 6
Dependent Claim
23 words
A compound of the formula ##STR14## where Z is a pharmaceutically acceptable cation and W is H or a a pharmaceutically acceptable cation.
Claim 7
Dependent Claim
16 words
The compound of claim 3 where Z is sodium, potassium, or ammonium and W is H.
Claim 8
Dependent Claim
13 words
The compound of claim 3 where Z is sodium and W is H.
Claim 9
Dependent Claim
13 words
The compound of claim 3 where Z is ammonium and W is H.
Claim 10
Dependent Claim
24 words
A pharmaceutical composition comprising an effective non-toxic antiviral amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
24 words
A pharmaceutical composition comprising an effective non-toxic antiviral amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
19 words
A pharmaceutical composition comprising an effective non-toxic antiviral amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate and a pharmaceutically acceptable carrier therefore.
Claim 13
Dependent Claim
19 words
A pharmaceutical composition comprising an effective non-toxic antiviral amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate and a pharmaceutically acceptable carrier therefore.
Claim 14
Dependent Claim
37 words
A pharmaceutical composition comprising an effective nontoxic antiviral amount of a compound of the formula ##STR15## where Z is a pharmaceutically acceptable cation, and W is H or a pharmaceutically acceptable cation and a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
37 words
A pharmaceutical composition comprising an effective nontoxic antiviral amount of a compound of the formula ##STR15## where Z is a pharmaceutically acceptable cation, and W is H or a pharmaceutically acceptable cation and a pharmaceutically acceptable carrier.
Claim 16
Dependent Claim
16 words
The composition of claim 9 where Z is sodium, potassium, or ammonium and W is H.
Claim 17
Dependent Claim
13 words
The composition of claim 9 where Z is sodium and W is H.
Claim 18
Dependent Claim
13 words
The composition of claim 9 where Z is ammonium and W is H.
Claim 19
Dependent Claim
14 words
The composition of claim 7 in unit dosage form for parenteral or oral administration.
Claim 20
Dependent Claim
13 words
The composition of claim 13 in the form of a tablet or capsule.
Claim 21
Dependent Claim
19 words
The composition of claim 7 in which the amount is 1 to 250 mg. calculated as the free phosphate.
Claim 22
Independent Claim
33 words
The method of treating a susceptible viral infection in a mammal which comprises the administration to said mammal of an effective, antiviral, non-toxic amount of 9-(2-hydroxyethoxymethyl)guanine monophosphate or a pharmaceutically acceptable salt thereof.
Claim 23
Independent Claim
33 words
The method of treating a susceptible viral infection in a mammal which comprises the administration to said mammal of an effective, antiviral, non-toxic amount of 9-(2-hydroxyethoxymethyl)guanine monophosphate or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
21 words
The method of claim 16 in which the amount is 0.1 to 250 mg/kg calculated as free base of mammal bodyweight.
Claim 25
Dependent Claim
15 words
The method of claim 16 in which the compound is orally, parenterally or topically administered.
Claim 26
Dependent Claim
17 words
The method of claim 16 in which the virus causing said infection is a herpes simplex virus.
Claim 27
Dependent Claim
12 words
The method of claim 16 in which the virus is herpes zoster.
Claim 28
Dependent Claim
12 words
The method of claim 16 in which the virus is herpes varicella.
Claim 29
Independent Claim
40 words
The method of treating herpes simplex or herpes zoster infection in mammals which comprises orally administering to said mammals in unit dosage form 0.1 to 250 mg/kg calculated as base of the 9-(2-hydroxyethoxymethyl)quanine monophosphate or a pharmaceutically acceptable salt thereof.
Claim 30
Independent Claim
40 words
The method of treating herpes simplex or herpes zoster infection in mammals which comprises orally administering to said mammals in unit dosage form 0.1 to 250 mg/kg calculated as base of the 9-(2-hydroxyethoxymethyl)quanine monophosphate or a pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim
11 words
The method of claim 22 in which 9-(2-hydroxyethoxymethyl)quanine monophosphate is administered.
Claim 32
Dependent Claim
16 words
The method of claim 22 in which a pharmaceutically acceptable salt of 9-(2-hydroxyethoxymethyl)guanine monophosphate is administered.
Claim 33
Dependent Claim
16 words
The method of claim 22 in which the compound is administered as part of a tablet.
Claim 34
Dependent Claim
16 words
The method of claim 23 in which the compound is administered as part of a tablet.
Claim 35
Dependent Claim
16 words
The method of claim 24 in which the compound is administered as part of a tablet.
Claim 36
Dependent Claim
9 words
The compound of claim 3 wherein W is hydrogen.
Claim 37
Dependent Claim
9 words
The composition of claim 9 wherein W is hydrogen.
Claim 38
Dependent Claim
14 words
The composition of claim 8 in unit dosage form for parenteral or oral administration.
Claim 39
Dependent Claim
14 words
The composition of claim 9 in unit dosage form for parenteral or oral administration.
Claim 40
Dependent Claim
19 words
The composition of claim 8 in which the amount is 1 to 250 mg. calculated as the free phosphate.
Claim 41
Dependent Claim
19 words
The composition of claim 9 in which the amount is 1 to 250 mg. calculated as the free phosphate.
Claim 42
Dependent Claim
11 words
The method of claim 16 in which 9-(2-hydroxyethoxymethyl)guanine monophosphate is administered.
Claim 43
Independent Claim
41 words
The method of treating a susceptable viral infection in a mammal which comprises the administration to said mammal of a compound of the formula ##STR16## where Z is a pharmaceutically acceptable cation and W is H or a pharmaceutically acceptable cation.
Claim 44
Independent Claim
41 words
The method of treating a susceptable viral infection in a mammal which comprises the administration to said mammal of a compound of the formula ##STR16## where Z is a pharmaceutically acceptable cation and W is H or a pharmaceutically acceptable cation.
Claim 45
Dependent Claim
16 words
The method of claim 35 where Z is sodium potassium or ammonium and W is H.
Claim 46
Dependent Claim
13 words
The method of claim 35 where Z is sodium and W is H.
Claim 47
Dependent Claim
13 words
The method of claim 35 where Z is ammonium and W is H.
Claim 48
Independent Claim
32 words
The method of treating a cytomegalovirus infection in a mammal which comprises administering an effective cytomegalovirus infection treatment amount of 9-(2-hydroxyethoxymethyl)guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 49
Independent Claim
32 words
The method of treating a cytomegalovirus infection in a mammal which comprises administering an effective cytomegalovirus infection treatment amount of 9-(2-hydroxyethoxymethyl)guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 50
Independent Claim
33 words
The method of treating an adenovirus infection in a mammal which comprises administering an effective adenovirus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 51
Independent Claim
33 words
The method of treating an adenovirus infection in a mammal which comprises administering an effective adenovirus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 52
Dependent Claim
12 words
The method of claim 40 in which the adenovirus is adenovirus 5.
Claim 53
Independent Claim
35 words
The method of treating a rhino virus infection in a mammal which comprises administering an effective rhino virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 54
Independent Claim
35 words
The method of treating a rhino virus infection in a mammal which comprises administering an effective rhino virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 55
Independent Claim
35 words
The method of treating a Mengo virus infection in a mammal which comprises administering an effective Mengo virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 56
Independent Claim
35 words
The method of treating a Mengo virus infection in a mammal which comprises administering an effective Mengo virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 57
Independent Claim
35 words
The method of treating a Sindbis virus infection in a mammal which comprises administering an effective Sindbis virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 58
Independent Claim
35 words
The method of treating a Sindbis virus infection in a mammal which comprises administering an effective Sindbis virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 59
Independent Claim
35 words
The method of treating a vaccinia virus infection in a mammal which comprises administering an effective vaccinia virus infection treatment ammount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 60
Independent Claim
35 words
The method of treating a vaccinia virus infection in a mammal which comprises administering an effective vaccinia virus infection treatment ammount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 61
Independent Claim
35 words
The method of treating a varicella virus infection in a mammal which comprises administering an effective varicella virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 62
Independent Claim
35 words
The method of treating a varicella virus infection in a mammal which comprises administering an effective varicella virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 63
Independent Claim
37 words
The method of treating a herpes simplex virus infection in a mammal which comprises administering an effective herpes simplex virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 64
Independent Claim
37 words
The method of treating a herpes simplex virus infection in a mammal which comprises administering an effective herpes simplex virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 65
Independent Claim
37 words
The method of treating a herpes zoster virus infection in a mammal which comprises administering an effective herpes zoster virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 66
Independent Claim
37 words
The method of treating a herpes zoster virus infection in a mammal which comprises administering an effective herpes zoster virus infection treatment amount of 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof to the infected mammal.
Claim 67
Dependent Claim
40 words
A pharmaceutical composition suitable for administration to the eye to treat a virus infection thereof which comprises an effective virus treatment amount of the compound 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.
Claim 68
Dependent Claim
40 words
A pharmaceutical composition suitable for administration to the eye to treat a virus infection thereof which comprises an effective virus treatment amount of the compound 9-(2-hydroxyethoxymethyl) guanine monophosphate or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.
Claim 69
Dependent Claim
11 words
The composition of claim 49 in the form of an ointment.
Claim 70
Dependent Claim
11 words
The composition of claim 49 in the form of a cream.
Claim 71
Dependent Claim
11 words
The composition of claim 49 in the form of eye drops.
Claim 72
Dependent Claim
25 words
The composition of anyone of claims 49 to 52 in which the concentration of the compound or pharmaceutically acceptable salt thereof is 0.1 to 10%.
References Cited (Backward Citations)
BE833006A
Cited
US4199574A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-31 | 1985-03-02 | 1985-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-31 | 1989-03-02 | 1989-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-31 | 1993-03-02 | 1993-09-01 | $7700.00 | Window Closed / Lapsed |