Patent US4025616A successfully refreshed from Google Patents.
US4025616A
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US
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Oral compositions for plaque, caries and calculus retardation with reduced staining tendencies
Assignee: Procter and Gamble Co
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Filing: 1975-11-25
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Granted: 1977-05-24
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Expires: 1995-11-25
Abstract
Abstract Oral compositions such as toothpastes, mouthwashes and the like containing an insoluble bis-biguanide compound which inhibits the formation of plaque and caries with reduced tendency of the bis-biguanide compound to produce a stain on oral surfaces as compared to soluble compounds.
Inventors
- 👤 John William Haefele
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 15:33
CPC Classifications
A; A61; A61Q; A61Q11/00; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/43; A61K8/55
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
515 words
An oral composition effective in inhibiting the formation of plaque, caries and calculus, said composition comprising a carrier suitable for use in the oral cavity and from about 0.01% to about 2.5% by weight of a water-soluble bis-biguanide compound having the generic formula: ##STR8## wherein A and A' each are selected from the group consisting of (A) substituted and unsubstituted phenyl radicals wherein the substituents are selected from the group consisting of up to two groups selected from the group consisting of alkyl and alkoxy groups containing from 1 to about 4 carbon atoms, a nitro group, and a halogen atom; (B) an alkyl group containing from 1 to about 12 carbon atoms; and (C) alicyclic groups containing from 4 to about 12 carbon atoms; wherein X and X' each represent an alkylene radical containing from 1 to 3 carbon atoms; wherein z and z' each are selected from the group consisting of 0 and 1; wherein R and R' each are selected from the group consisting of hydrogen, an alkyl radical containing from 1 to about 12 carbon atoms, and on aralkyl radical containing from 7 to about 12 carbon atoms; wherein n is an integer from 2 to 12 inclusive; wherein the polymethylene chain (CH 2 ) n can be interrupted by up to 5 moieties selected from the group consisting of ether, thioether, phenyl, and naphthyl; wherein L is a number from about 1 to 4; and wherein Y is an anion which will form a pharmaceutically acceptable water-insoluble bis-biguanide compound, said anion being derived from a compound selected from the group consisting of bisulfites, polymaleates, phosphites, hypophosphites, perfluorooctanoates, silicates, sorbates, salicylates, maleates, tartrates, citrates, fumarates, ethylenediamine tetraacetates, iminodiacetates, cinnamates, thiocyanates, arginates, pyromellitates, tetracarboxybutyrates, benzoates, glutarates, perfluoropropionates and polyphosphonates selected from the group consisting of: ##STR9## wherein in both formulae R 1 and R 2 are selected from the group consisting of hydrogen and CH 2 OH; n is an integer of from 3 to 12; R 3 is selected from the group consisting of hydrogen, alkyl containing from 1 to about 20 carbon atoms, alkenyl containing from 2 to about 20 carbon atoms, phenyl, naphthyl, phenylethenyl, benzyl, halogen, amino, dimethylamino, diethylamino, N-hydroxy-N-ethylamino, acetylamino, --CH 2 COOH, --CH 2 PO 3 H 2 , --CH(PO 3 H 2 ) (OH) and --CH 2 CH(PO 3 H 2 ) 2 ; and R 4 is selected from the group consisting of hydrogen, lower alkyl, amino, benzyl, halogen, hydroxyl, --CH 2 COOH, --CH 2 PO 3 H 2 , and -- CH 2 CH 2 PO 3 H 2 ; ##STR10## wherein R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each selected from the group consisting of hydrogen and lower alkyl; ##STR11## wherein n is an integer from 3 to 9; ##STR12## carboxyphosphonates selected from the group consisting of ##STR13## ##STR14## wherein X and Y are each selected from the group consisting of hydrogen and hydroxy; and the condensation products of ammonia and phosphorous pentoxide, said condensation products consisting of the compounds ##STR15##
Claim 2
Dependent Claim
515 words
An oral composition effective in inhibiting the formation of plaque, caries and calculus, said composition comprising a carrier suitable for use in the oral cavity and from about 0.01% to about 2.5% by weight of a water-soluble bis-biguanide compound having the generic formula: ##STR8## wherein A and A' each are selected from the group consisting of (A) substituted and unsubstituted phenyl radicals wherein the substituents are selected from the group consisting of up to two groups selected from the group consisting of alkyl and alkoxy groups containing from 1 to about 4 carbon atoms, a nitro group, and a halogen atom; (B) an alkyl group containing from 1 to about 12 carbon atoms; and (C) alicyclic groups containing from 4 to about 12 carbon atoms; wherein X and X' each represent an alkylene radical containing from 1 to 3 carbon atoms; wherein z and z' each are selected from the group consisting of 0 and 1; wherein R and R' each are selected from the group consisting of hydrogen, an alkyl radical containing from 1 to about 12 carbon atoms, and on aralkyl radical containing from 7 to about 12 carbon atoms; wherein n is an integer from 2 to 12 inclusive; wherein the polymethylene chain (CH 2 ) n can be interrupted by up to 5 moieties selected from the group consisting of ether, thioether, phenyl, and naphthyl; wherein L is a number from about 1 to 4; and wherein Y is an anion which will form a pharmaceutically acceptable water-insoluble bis-biguanide compound, said anion being derived from a compound selected from the group consisting of bisulfites, polymaleates, phosphites, hypophosphites, perfluorooctanoates, silicates, sorbates, salicylates, maleates, tartrates, citrates, fumarates, ethylenediamine tetraacetates, iminodiacetates, cinnamates, thiocyanates, arginates, pyromellitates, tetracarboxybutyrates, benzoates, glutarates, perfluoropropionates and polyphosphonates selected from the group consisting of: ##STR9## wherein in both formulae R 1 and R 2 are selected from the group consisting of hydrogen and CH 2 OH; n is an integer of from 3 to 12; R 3 is selected from the group consisting of hydrogen, alkyl containing from 1 to about 20 carbon atoms, alkenyl containing from 2 to about 20 carbon atoms, phenyl, naphthyl, phenylethenyl, benzyl, halogen, amino, dimethylamino, diethylamino, N-hydroxy-N-ethylamino, acetylamino, --CH 2 COOH, --CH 2 PO 3 H 2 , --CH(PO 3 H 2 ) (OH) and --CH 2 CH(PO 3 H 2 ) 2 ; and R 4 is selected from the group consisting of hydrogen, lower alkyl, amino, benzyl, halogen, hydroxyl, --CH 2 COOH, --CH 2 PO 3 H 2 , and -- CH 2 CH 2 PO 3 H 2 ; ##STR10## wherein R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each selected from the group consisting of hydrogen and lower alkyl; ##STR11## wherein n is an integer from 3 to 9; ##STR12## carboxyphosphonates selected from the group consisting of ##STR13## ##STR14## wherein X and Y are each selected from the group consisting of hydrogen and hydroxy; and the condensation products of ammonia and phosphorous pentoxide, said condensation products consisting of the compounds ##STR15##
Claim 3
Dependent Claim
21 words
A composition in accordance with claim 1 which has a pH within the range of from about 4 to about 9.
Claim 4
Dependent Claim
33 words
A composition in accordance with claim 2 which contains from about 0.05% to about 1.2% by weight of the bis-biguanide compound and which has a pH of from about 6 to about 7.5.
Claim 5
Dependent Claim
25 words
A composition in accordance with claim 3 wherein A-- (X) z and A' --(X') z' , each represent an ethylhexyl group and n is 6.
Claim 6
Dependent Claim
24 words
A composition in accordance with claim 3 wherein A and A' are each p-chlorophenyl groups, z and z' are 0, and n is 6.
Claim 7
Dependent Claim
35 words
A composition in accordance with claim 3 which contains a water-soluble source of fluoride in a quantity sufficient to provide fluoride in an amount of from about 0.025% to about 5.0% as F - .
Claim 8
Dependent Claim
242 words
A composition in accordance with claim 1 wherein the compound from which the anion Y is derived is a polyphosphonate selected from the group consisting of: ##STR16## wherein in both formulae R 1 and R 2 are selected from the group consisting of hydrogen and CH 2 OH; n is an integer of from 3 to 12; R 3 is selected from the group consisting of hydrogen, alkyl containing from 1 to about 20 carbon atoms, alkenyl containing from 2 to about 20 carbon atoms, phenyl, naphthyl, phenylethenyl, benzyl, halogen, amino, dimethylamino, diethylamino, N-hydroxy-N-ethylamino, acetylamino, --CH 2 COOH, -- CH 2 PO 3 H 2 , --CH(PO 3 H 2 ) (OH) and --CH 2 CH(PO 3 H 2 ) 2 ; and R 4 is selected from the group consisting of hydrogen, lower alkyl, amino, benzyl, halogen, hydroxyl, --CH 2 COOH, --CH 2 PO 3 H 2 , and --CH 2 CH 2 PO 3 H 2 ; ##STR17## wherein R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each selected from the group consisting of hydrogen and lower alkyl; ##STR18## wherein n is an integer from 3 to 9; ##STR19## carboxyphosphonates selected from the group consisting of ##STR20## wherein X and Y are each selected from the group consisting of hydrogen and hydroxy; and the condensation products of ammonia and phosphorous pentoxide, said condensation products consisting of the compounds ##STR21##
Claim 9
Dependent Claim
21 words
A composition in accordance with claim 7 which has a pH within the range of from about 4 to about 9.
Claim 10
Dependent Claim
32 words
A composition in accordance with claim 8 which contains from about 0.05% to about 1.2% by weight of the bis-biguanide compounds, and which has pH of from about 6 to about 7.5.
Claim 11
Dependent Claim
25 words
A composition in accordance with claim 9 wherein A-- (X) z and A'-- (X') z' , each represent an ethylhexyl group and n is 6.
Claim 12
Dependent Claim
24 words
A composition in accordance with claim 9 wherein A and A' are each p-chlorophenyl groups, z and z' are 0, and n is 6.
Claim 13
Dependent Claim
24 words
A composition in accordance with claim 11 wherein the bis-biguanide compound is [1,6-di(N 1 , N 1 '-p-chlorophenyldiguanido-N 5 , N 5 ')-hexane] ethane-1-hydroxy-1,1-diphosphonate.
Claim 14
Dependent Claim
35 words
A composition in accordance with claim 12 which contains a water-soluble source of fluoride in a quantity sufficient to provide fluoride in an amount of from about 0.025% to about 5.0% as F - .
Claim 15
Dependent Claim
48 words
A composition in accordance with claim 1 wherein the compound from which the anion Y is derived is selected from the group consisting of bisulfites, polymaleates, phosphites, hypophosphites, perfluorooctanoates, silicates, sorbates, salicylates, maleates, tartrates, citrates, fumarates, ethylenediamine tetraacetates, iminodiacetates, cinnamates, thiocyanates, arginates, pyromellitates, tetracarboxybutyrates, benzoates, glutarates, and perfluoropropionates.
Claim 16
Dependent Claim
21 words
A composition in accordance with claim 14 which has a pH within the range of from about 4 to about 9.
Claim 17
Dependent Claim
33 words
A composition in accordance with claim 15 which contains from about 0.05% to about 1.2% by weight of the bis-biguanide compound, and which has a pH of from about 6 to about 7.5.
Claim 18
Dependent Claim
25 words
A composition in accordance with claim 16 wherein A-- (X) z and A'-- (X') z' , each represent an ethylhexyl group and n is 6.
Claim 19
Dependent Claim
29 words
A composition in accordance with claim 17 wherein the compound from which the anion Y is derived is selected from the group consisting of citrates, tartrates, fumarates, and cinnamates.
Claim 20
Dependent Claim
24 words
A composition in accordance with claim 16 wherein A and A' are each p-chlorophenyl groups, z and z' are 0, and n is 6.
Claim 21
Dependent Claim
29 words
A composition in accordance with claim 19 wherein the compound from which the anion Y is derived is selected from the group consisting of citrates, tartrates, fumarates and cinnamates.
Claim 22
Dependent Claim
35 words
A composition in accordance with claim 16 which contains a water-soluble source of fluoride in a quantity sufficient to provide fluoride in an amount of from about 0.025% to about 5.0% as F - .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-23 | 1980-11-22 | 1981-05-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-23 | 1984-11-22 | 1985-05-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-23 | 1988-11-22 | 1989-05-24 | $7700.00 | Window Closed / Lapsed |