US4587240A
Expired / Lapsed
US
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Pharmaceutical compositions
Assignee: BTG International Ltd
•
Filing: 1984-09-18
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Granted: 1986-05-06
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Expires: 2004-09-18
Abstract
Abstract Compounds which are a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, aliphatic amine, carboxy, cyano, aliphatic ester, halogen, hydroxy and sulpho groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic amine, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms in the compound is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group, or a salt thereof containing a physiolgically acceptable ion or ions, are of value in the treatment of patients having a toxic concentration of a metal, particularly iron, in the body whilst the iron complexes of such compounds are of value in the treatment of iron deficiency anaemia.
Inventors
- 👤 Robert C. Hider
- 👤 George Kontoghiorghes
- 👤 Jack Silver
- 👤 Michael A. Stockham
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 00:19
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/89; A; A61; A61P; A61P3/00; A61P7/00; A61P7/06; C07F; C07F15/00; C07F15/02; C07F15/025
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
146 words
A method for the treatment of a patient having a toxic concentration of iron in the body which comprises administering to said patient a compound being a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group, or a salt therof containing a physiologically acceptable cation in an amount effective to reduce said toxic concentration of the metal.
Claim 2
Independent Claim
146 words
A method for the treatment of a patient having a toxic concentration of iron in the body which comprises administering to said patient a compound being a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group, or a salt therof containing a physiologically acceptable cation in an amount effective to reduce said toxic concentration of the metal.
Claim 3
Dependent Claim
33 words
The method according to claim 1, in which at least one of the ring carbon atom substituents is a hydroxy, alkoxy or substituted alkoxy group, or a hydroxy- or alkoxy-substituted aliphatic hydrocarbon group.
Claim 4
Dependent Claim
79 words
The method according to claim 2, in which at least one of the ring carbon atom substituents is a hydroxy group, an alkoxy group of 1 to 5 carbon atoms, an alkoxy group of 2 to 4 carbon atoms substituted by a hydroxy group, or an alkoxy group of 2 to 4 carbon atoms substituted by an alkoxy group of 1 to 4 carbon atoms, the total number of carbon atoms in the alkoxyalkoxy group being 3 to 6.
Claim 5
Dependent Claim
39 words
The method according to claim 3, in which the ring carbon atoms of the 1-hydroxypyrid-2-one are substituted by a single one of said substituents and additionally by one or more aliphatic hydrocarbon groups of 1 to 4 carbon atoms.
Claim 6
Dependent Claim
25 words
The method according to claim 3, in which the ring carbon atoms of the 1-hydroxypyrid-2-one are substituted only by a single one of said substituents.
Claim 7
Dependent Claim
22 words
The method according to claim 5, in which the single one of said substituents is located at the 4-position of the 1-hydroxypyrid-2-one.
Claim 8
Dependent Claim
18 words
The method according to claim 1, in which the 1-hydroxypyrid-2-one is 1-hydroxy-4-methoxypyrid-2-one, 4-ethoxy-1-hydroxypyrid-2-one, 1,4-dihydroxypyrid-2-one, 1-hydroxy-4-(2'-hydroxyethoxy)-pyrid-2-one, 1-hydroxy-4-(3'-hydroxypropoxy)-pyrid-2-one or 1-hydroxy-4-(2'-methoxyethoxy)-pyrid-2-one.
Claim 9
Dependent Claim
43 words
The method according to claim 1, wherein said at least one substituent is an alkoxy group substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, and wherein at least one additional hydrogen atom may be substituted by a hydroxy group.
Claim 10
Dependent Claim
81 words
The method of claim 8, wherein one of the said hydrogen atoms attached to the ring carbon atoms of the 1-hydroxypyrid-2-one is replaced by a C 2-4 alkoxy group substituted by a hydroxy group or by a C 1-4 alkoxy group, with the total number of carbon atoms in the alkoxyalkoxy group ranging from 3 to 6, and wherein at least one more of the said hydrogen atoms can be replaced by an aliphatic group of 1 to 4 carbon atoms.
Claim 11
Independent Claim
142 words
A method for the treatment of a patient to effect an increase in the level of iron in the patient's bloodstream which comprises adminstering to said patient a compound being an iron complex of a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group, in an amount effective to achieve such an increase.
Claim 12
Independent Claim
142 words
A method for the treatment of a patient to effect an increase in the level of iron in the patient's bloodstream which comprises adminstering to said patient a compound being an iron complex of a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group, in an amount effective to achieve such an increase.
Claim 13
Dependent Claim
33 words
The method according to claim 10, in which at least one of the ring carbon atom substituents is a hydroxy, alkoxy or substituted alkoxy, group, or a hydroxy- or alkoxy-substituted aliphatic hydrocarbon group.
Claim 14
Dependent Claim
79 words
The method according to claim 11, in which at least one of the ring carbon atom substituents is a hydroxy group, an alkoxy group of 1 to 5 carbon atoms, an alkoxy group of 2 to 4 carbon atoms substituted by a hydroxy group, or an alkoxy group of 2 to 4 carbon atoms substituted by an alkoxy group of 1 to 4 carbon atoms, the total number of carbon atoms in the alkoxyalkoxy group being 3 to 6.
Claim 15
Dependent Claim
39 words
The method according to claim 12, in which the ring carbon atoms of the 1-hydroxypyrid-2-one are substituted by a single one of said substituents and additionally by one or more aliphatic hydrocarbon groups of 1 to 4 carbon atoms.
Claim 16
Dependent Claim
25 words
The method according to claim 12, in which the ring carbon atoms of the 1-hydroxypyrid-2-one are substituted only by a single one of said substituents.
Claim 17
Dependent Claim
22 words
The method according to claim 14 in which the single one of said substituents is located at the 4-position of the 1-hydroxypyrid-2-one.
Claim 18
Dependent Claim
18 words
The method according to claim 10, in which the 1-hydroxypyrid-2-one is 1-hydroxy-4-methoxypyrid-2-one, 4-ethoxy-1-hydroxypyrid-2-one, 1,4-dihydroxypyrid-2-one, 1-hydroxy-4-(2'-hydroxyethoxy)-pyrid-2-one, 1-hydroxy-4-(3'-hydroxypropoxy)-pyrid-2-one or 1-hydroxy-4-(2'-methoxyethoxy)-pyrid-2-one.
Claim 19
Dependent Claim
17 words
The method according to claim 16, in which the iron complex is the neutral 3:1 1-hydroxypyrid-2-one:iron(III) complex.
Claim 20
Dependent Claim
17 words
The method according to claim 10, in which the iron complex is the neutral 3:1 1-hydroxypyrid-2-one:iron(III) complex.
Claim 21
Dependent Claim
117 words
A pharmaceutical composition comprising a neutral 3:1 1-hydroxypyrid-2-one:iron(III) complex of a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group, together with a physiologically acceptable diluent or carrier.
Claim 22
Dependent Claim
117 words
A pharmaceutical composition comprising a neutral 3:1 1-hydroxypyrid-2-one:iron(III) complex of a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group, together with a physiologically acceptable diluent or carrier.
Claim 23
Dependent Claim
13 words
The pharmaceutical composition according to claim 19, which comprises a sterile, pyrogen-free diluent.
Claim 24
Dependent Claim
12 words
The pharmaceutical composition according to claim 19 which comprises a solid carrier.
Claim 25
Dependent Claim
24 words
The pharmaceutical composition according to claim 21 which is adapted to release of the iron complex in the intestine rather than in the stomach.
Claim 26
Dependent Claim
11 words
The pharmaceutical composition according to claim 19 in unit dosage form.
Claim 27
Dependent Claim
80 words
The pharmaceutical composition according to claim 19, in which at least one of the ring carbon atom substituents is a hydroxy group, an alkoxy group of 1 to 5 carbon atoms, an alkoxy group of 2 to 4 carbon atoms substituted by a hydroxy group, or an alkoxy group of 2 to 4 carbon atoms substituted by an alkoxy group of 1 to 4 carbon atoms, the total number of carbon atoms in the alkoxyalkoxy group being 3 to 6.
Claim 28
Dependent Claim
109 words
A compound being a neutral 3:1 1-hydroxypyrid-2-one:iron (III) complex of a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group.
Claim 29
Dependent Claim
109 words
A compound being a neutral 3:1 1-hydroxypyrid-2-one:iron (III) complex of a 1-hydroxypyrid-2-one in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by a substituent selected from aliphatic acyl, aliphatic amide, cyano, aliphatic ester, halogen and hydroxy groups, alkoxy groups and alkoxy groups substituted by an alkoxy, aliphatic amide, aliphatic ester, halogen or hydroxy group, aliphatic hydrocarbon groups and aliphatic hydrocarbon groups substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms is effected only by substituents selected from aliphatic hydrocarbon groups, halogen groups and aliphatic hydrocarbon groups substituted by a halogen group.
Claim 30
Dependent Claim
30 words
The compound according to claim 25, in which at least one of the ring carbon atom substituents is a hydroxy, alkoxy, substituted alkoxy, or hydroxy- or alkoxy-substituted aliphatic hydrocarbon group.
Claim 31
Dependent Claim
79 words
The compound according to claim 26, in which at least one of the ring carbon atom substituents is a hydroxy group, an alkoxy group of 1 to 5 carbon atoms, an alkoxy group of 2 to 4 carbon atoms substituted by a hydroxy group, or an alkoxy group of 2 to 4 carbon atoms substituted by an alkoxy group of 1 to 4 carbon atoms, the total number of carbon atoms in the alkoxyalkoxy group being 3 to 6.
Claim 32
Dependent Claim
39 words
The compound according to claim 27, in which the ring carbon atoms of the 1-hydroxypyrid-2-one are substituted by a single one of said substituents and additionally by one or more aliphatic hydrocarbon groups of 1 to 6 carbon atoms.
Claim 33
Dependent Claim
25 words
The compound according to claim 27, in which the ring carbon atoms of the 1-hydroxypyrid-2-one are substituted only by a single one of said substituents.
Claim 34
Dependent Claim
22 words
The compound according to claim 29, in which the single one of said substituents is located at the 4-position of the 1-hydroxypyrid-2-one.
Claim 35
Dependent Claim
18 words
The compound according to claim 30, in which the 1-hydroxypyrid-2-one is 1-hydroxy-4-methoxypyrid-2-one, 4-ethoxy-1-hydroxy-pyrid-2-one, 1,4-dihydroxypyrid-2-one, 1-hydroxy-4-(2'-hydroxyethoxy)-pyrid-2-one, 1-hydroxy-4-(3'-hydroxypropoxy)-pyrid-2-one or 1-hydroxy-4-(2'-methoxyethoxy)-pyrid-2-one.
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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) | 1989-05-05 | 1989-11-04 | 1990-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-05-05 | 1993-11-04 | 1994-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-05-05 | 1997-11-04 | 1998-05-06 | $7700.00 | Window Closed / Lapsed |