US4988680A
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Phosphonoalkylpurine derivatives
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1989-04-14
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Granted: 1991-01-29
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Expires: 2009-04-14
Abstract
Abstract Halogenated 9-phosphonoalkyl derivatives of guanine and hypoxanthine are inhibitors of purine nucleoside phosphorylase and are useful as immuno suppressant and antiparasitic agents as well as against T cell leukemia and antiureicopoietic agents.
Inventors
- 👤 Serge J. Halazy
- 👤 Charles Danzin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:06
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/16; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616; A; A61; A61P; A61P33/00; A61P33/02; A61P37/00; A61P37/02; A61P37/06; A61P43/00
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
163 words
A compound of the formula ##STR12## wherein R is a phosphoroalkyl group of the formula: ##STR13## wherein m and n are each an integer of from 1 to 5 with the proviso that m+n must be an interger of from 2 to 6; Z is an oxy group or a methylene group; R 4 is a hydrogen and R 4 ' is a hydrogen or hydroxy group or R 4 and R 4 ' taken together with the carbon atom to which they are attached form a keto group; X and Y are each a hydrogen, fluoro or chloro group with the proviso that both of X and Y cannot be hydrogen; R 5 and R 6 are each a hydrogen or a (C 1 -C 4 )alkyl group; R 1 is a hydroxy or sulfhydryl group; R 2 is a hydrogen or amino group; and R 3 is a hydrogen, amino, hydroxy or --NH--NH 2 group; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
163 words
A compound of the formula ##STR12## wherein R is a phosphoroalkyl group of the formula: ##STR13## wherein m and n are each an integer of from 1 to 5 with the proviso that m+n must be an interger of from 2 to 6; Z is an oxy group or a methylene group; R 4 is a hydrogen and R 4 ' is a hydrogen or hydroxy group or R 4 and R 4 ' taken together with the carbon atom to which they are attached form a keto group; X and Y are each a hydrogen, fluoro or chloro group with the proviso that both of X and Y cannot be hydrogen; R 5 and R 6 are each a hydrogen or a (C 1 -C 4 )alkyl group; R 1 is a hydroxy or sulfhydryl group; R 2 is a hydrogen or amino group; and R 3 is a hydrogen, amino, hydroxy or --NH--NH 2 group; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
12 words
A compound of claim 1 wherein R 2 is an amino group.
Claim 4
Dependent Claim
20 words
A compound of one of claims 1 or 2 wherein one or both of X and Y are fluoro groups.
Claim 5
Dependent Claim
16 words
A compound of one of claims 1 or 2 wherein R 3 is an amino group.
Claim 6
Dependent Claim
26 words
A compound of one of claims 1 or 2 wherein Z is a methylene and wherein n +m is an integer of from 2 to 5.
Claim 7
Dependent Claim
8 words
A compound of claim 1 which is 9-(7-phosphono-7,7difluoroheptyl)guanine.
Claim 8
Dependent Claim
9 words
A compound of claim 1 which is 9-(7-phosphono-7,7- difluorohept-6-ol)guanine.
Claim 9
Dependent Claim
10 words
A compound of claim 1 which is 9-(7-phosphono-7,7-difluoroheptyl)guanine ethyl ester.
Claim 10
Dependent Claim
8 words
A compound of claim 1 which is 9-(6-phosphono-6-fluoroheptyl)guanine.
Claim 11
Dependent Claim
8 words
A compound of claim 1 which is [9-(5-phosphono-5,5-difluoropentyl)guanine].
Claim 12
Dependent Claim
9 words
A compound of claim 1 which is 8-amino-[9-(5- phosphono-5,5-difluoropentyl)]guanine.
Claim 13
Independent Claim
169 words
A method of suppressing the immune system in a patient in need thereof which comprises administering to the patient an effective amount of a compound of the formula ##STR14## wherein R is a phosphonoalkyl group of the formula: ##STR15## wherein m and n are each an integer of from 1 to 5 with the proviso that m+n must be an integer of from 2 to 6; Z is an oxy group or a methylene group; R 4 is a hydrogen and R 4 ' is a hydrogen or hydroxy group or R 4 and R 4 ' taken together with the carbon atom to which they are attached form a keto group; X and Y are each a hydrogen, fluoro or chloro group with the proviso that both of X and Y cannot be hydrogen; R 1 is a hydroxy or sulfhydryl group; R 2 is a hydrogen or amino group; and R 3 is a hydrogen, amino, hydroxy or --NH--NH 2 group; or a pharmaceutically acceptable salt thereof.
Claim 14
Independent Claim
169 words
A method of suppressing the immune system in a patient in need thereof which comprises administering to the patient an effective amount of a compound of the formula ##STR14## wherein R is a phosphonoalkyl group of the formula: ##STR15## wherein m and n are each an integer of from 1 to 5 with the proviso that m+n must be an integer of from 2 to 6; Z is an oxy group or a methylene group; R 4 is a hydrogen and R 4 ' is a hydrogen or hydroxy group or R 4 and R 4 ' taken together with the carbon atom to which they are attached form a keto group; X and Y are each a hydrogen, fluoro or chloro group with the proviso that both of X and Y cannot be hydrogen; R 1 is a hydroxy or sulfhydryl group; R 2 is a hydrogen or amino group; and R 3 is a hydrogen, amino, hydroxy or --NH--NH 2 group; or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
12 words
A method of claim 12 wherein R 2 is an amino group.
Claim 16
Independent Claim
20 words
A method of one of claims 12 or 13 wherein one or both of X and Y are fluoro groups.
Claim 17
Independent Claim
16 words
A method of one of claims 12 or 13 wherein R 3 is an amino group.
Claim 18
Independent Claim
26 words
A method of one of claims 12 or 13 wherein Z is a methylene and wherein n+ m is an integer of from 3 to 5.
Claim 19
Dependent Claim
11 words
A method of claim 12 wherein the compound is 9-(7- phosphono-7,7-difluoroheptyl)guanine.
Claim 20
Dependent Claim
10 words
A method of claim 12 wherein the compound is 9-(7-ohosphone-7,7-difluorohept-6-ol)guanine.
Claim 21
Dependent Claim
13 words
A method of claim 12 wherein the compound is 9-(7- phosphono-7,7-difluoroheptyl)guanine ethyl ester.
Claim 22
Dependent Claim
10 words
A method of claim 12 wherein the compound is 9-(6-phosphono-6-fluoroheptyl)guanine.
Claim 23
Dependent Claim
11 words
A method of claim 12 wherein the compound is [9-(5- phosphono-5,5-difluoropentyl)guanine].
Claim 24
Dependent Claim
11 words
A method of claim 12 wherein the compound is 8-amino-[ 9-(5-phosphono-5,5-difluoropentyl)]guanine.
Claim 25
Independent Claim
184 words
A method of inhibiting purine nucleoside phosphorylase in a patient in need thereof which comprises administering to the patient an effective amount of a compound of the formula: ##STR16## wherein R is a phosphonoalkyl group of the formula ##STR17## wherein m and n are each an integer of from 1 to 5 with the proviso that m+n must be an integer of from 2 to 6; Z is an oxy group or a methylene group; R 4 is a hydrogen and R 4 ' is a hydrogen or hydroxy group or R 4 and R 4 ' taken together with the carbon atom to which they are attached form a keto group; X and Y are each a hydrogen, fluoro or chloro group with the proviso that both of X and Y cannot be hydrogen; R 5 and R 6 are each a hydrogen or (C 1 --C 4 )alkyl group; R 1 is a hydroxy or sulfhydryl group; R 2 is a hydrogen or amino group; and R 3 is a hydrogen, amino, hydroxy or--NH--NH 2 group; or a pharmaceutically acceptable salt thereof.
Claim 26
Independent Claim
184 words
A method of inhibiting purine nucleoside phosphorylase in a patient in need thereof which comprises administering to the patient an effective amount of a compound of the formula: ##STR16## wherein R is a phosphonoalkyl group of the formula ##STR17## wherein m and n are each an integer of from 1 to 5 with the proviso that m+n must be an integer of from 2 to 6; Z is an oxy group or a methylene group; R 4 is a hydrogen and R 4 ' is a hydrogen or hydroxy group or R 4 and R 4 ' taken together with the carbon atom to which they are attached form a keto group; X and Y are each a hydrogen, fluoro or chloro group with the proviso that both of X and Y cannot be hydrogen; R 5 and R 6 are each a hydrogen or (C 1 --C 4 )alkyl group; R 1 is a hydroxy or sulfhydryl group; R 2 is a hydrogen or amino group; and R 3 is a hydrogen, amino, hydroxy or--NH--NH 2 group; or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim
12 words
A method of claim 23 wherein R 2 is an amino group.
Claim 28
Independent Claim
20 words
A method of one of claims 23 or 24 wherein one or both of X and Y are fluoro groups.
Claim 29
Independent Claim
16 words
A method of one of claims 23 or 24 wherein R 3 is an amino group.
Claim 30
Independent Claim
26 words
A method of one of claims 23 or 24 wherein Z is a methylene and wherein n+ m is an integer of from 2 to 5.
Claim 31
Dependent Claim
10 words
A method of claim 23 wherein the compound is 9-(7-phosphono-7,7-difluoroheptyl)guanine.
Claim 32
Dependent Claim
10 words
A method of claim 23 wherein the compound is 9-(7-phosphono-7,7-difluorohept-6-ol)guanine.
Claim 33
Dependent Claim
13 words
A method of claim 23 wherein the compound is 9-(7- phosphono-7,7-difluoroheptyl)guanine ethyl ester.
Claim 34
Dependent Claim
10 words
A method of claim 23 wherein the compound is 9-(6-phosphono-6-fluoroheptyl)guanine.
References Cited (Backward Citations)
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US4695654A
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US4719313A
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1994-01-28 | 1994-07-30 | 1995-01-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-01-28 | 1998-07-30 | 1999-01-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-01-28 | 2002-07-30 | 2003-01-29 | $7700.00 | Window Closed / Lapsed |