US4235875A
Expired / Lapsed
US
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Anticaries piperidino compounds
Assignee: Pharmacia Animal Health Inc
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Filing: 1978-04-24
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Granted: 1980-11-25
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Expires: 1998-04-24
Abstract
Abstract Novel alkyl 1-(hydroxyalkyl)piperidines and acid addition salts thereof, useful as inhibitors of dental plaque and therefore also useful against dental caries and periodontitis, are disclosed. Methods of making same, orally-acceptable compositions thereof, a method of treating therewith, and important and novel intermediates for the production thereof are also disclosed.
Inventors
- 👤 Sven E. H. Hernestam
- 👤 Lars O. Willard
- 👤 Aina L. Abramo
- 👤 Hans-Bertil Johansson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 07:37
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/10; C07D211/14; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/4906; A61K8/4926; A61P; A61P1/00; A61P1/02; A61P29/00; A61Q; A61Q11/00
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
142 words
An oral and dental hygiene composition suitable for use in the inhibition of dental plaque comprising (a) an alkyl 1-hydroxyalkylpiperidine having the Formula I, ##STR32## which is substituted in the 2,3, or 4 position with ##STR33## wherein R 1 is an alkyl group, straight or branched, having at least seven carbon atoms, R 2 is hydrogen or an alkyl group, R 1 and R 2 together having 7-14 carbon atoms, and wherein R 3 is a hydroxyalkyl group of 2-6 carbon atoms, the sum of the carbon atoms in R 1 , R 2 , and R 3 being at least ten; "C" representing CH 2 except for the one carbon atom bearing the said R 1 R 2 substitution, or (b) an orally acceptable acid addition salt thereof, in an amount effective for said purpose, in association with an orally-acceptable carrier.
Claim 2
Dependent Claim
142 words
An oral and dental hygiene composition suitable for use in the inhibition of dental plaque comprising (a) an alkyl 1-hydroxyalkylpiperidine having the Formula I, ##STR32## which is substituted in the 2,3, or 4 position with ##STR33## wherein R 1 is an alkyl group, straight or branched, having at least seven carbon atoms, R 2 is hydrogen or an alkyl group, R 1 and R 2 together having 7-14 carbon atoms, and wherein R 3 is a hydroxyalkyl group of 2-6 carbon atoms, the sum of the carbon atoms in R 1 , R 2 , and R 3 being at least ten; "C" representing CH 2 except for the one carbon atom bearing the said R 1 R 2 substitution, or (b) an orally acceptable acid addition salt thereof, in an amount effective for said purpose, in association with an orally-acceptable carrier.
Claim 3
Dependent Claim
9 words
Composition of claim 1 wherein R 3 is omega-hydroxyalkyl.
Claim 4
Dependent Claim
26 words
Composition of claim 1 wherein the total number of carbon atoms in R 1 , R 2 , and R 3 is between ten and fifteen.
Claim 5
Dependent Claim
17 words
Composition of claim 1 wherein R 1 is selected from the group consisting n-octyl, n-nonyl, and n-decyl.
Claim 6
Dependent Claim
20 words
Composition of claim 1 wherein R 3 is selected from the group consisting of 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl, and 6-hydroxyhexyl.
Claim 7
Dependent Claim
14 words
Composition of claim 1 wherein R 1 is n-octyl and R 3 is 3-hydroxypropyl.
Claim 8
Dependent Claim
14 words
Composition of claim 1 wherein the active ingredient is a 4-n-octyl-1-(3-hydroxypropyl)piperidine acid addition salt.
Claim 9
Dependent Claim
13 words
Composition of claim 1 wherein R 1 and R 2 are both alkyl.
Claim 10
Dependent Claim
14 words
The composition of claim 1 wherein R 1 is a symmetrically branched octyl group.
Claim 11
Dependent Claim
12 words
The composition of claim 1 wherein R 2 is hydrogen or methyl.
Claim 12
Dependent Claim
16 words
The composition of claim 1 wherein R 1 is a n-nonyl and R 3 is 3-hydroxypropyl.
Claim 13
Dependent Claim
15 words
The composition of claim 1 wherein the active ingredient is 3-n-nonyl-1-(3-hydroxypropyl) piperidine acid addition salt.
Claim 14
Dependent Claim
13 words
The composition of claim 1 wherein the active ingredient is 3-n-nonyl-1-(3-hydroxypropyl) piperidine hydrochloride.
Claim 15
Dependent Claim
15 words
The composition of claim 1 wherein R 1 is 2,2-dipropylethyl and R 3 is 2-hydroxyethyl.
Claim 16
Dependent Claim
15 words
The composition of claim 1 wherein the active ingredient is 4-(2,2-dipropylethyl)-1-(2-hydroxyethyl) piperidine acid addition salt.
Claim 17
Dependent Claim
13 words
The composition of claim 1 wherein the active ingredient is 4-(2,2-dipropylethyl)-1-(2-hydroxyethyl) piperidine hydrochloride.
Claim 18
Dependent Claim
136 words
Method for the inhibition of dental plaque, comprising the step of contacting a tooth with (a) an alkyl 1-hydroxyalkylpiperidine having the Formula I, ##STR34## which is substituted in the 2, 3, or 4 position with ##STR35## wherein R 1 is an alkyl group, straight or branched, having at least seven carbon atoms, R 2 is hydrogen or an alkyl group, R 1 and R 2 together having 7-14 carbon atoms, and wherein R 3 is a hydroxyalkyl group of 2-6 carbon atoms, the sum of the carbon atoms in R 1 , R 2 , and R 3 being at least ten; "C" representing CH 2 except for the one carbon atom bearing the said R 1 R 2 substitution, or (b) an orally acceptable acid addition salt thereof, in an amount effective for said purpose.
Claim 19
Dependent Claim
136 words
Method for the inhibition of dental plaque, comprising the step of contacting a tooth with (a) an alkyl 1-hydroxyalkylpiperidine having the Formula I, ##STR34## which is substituted in the 2, 3, or 4 position with ##STR35## wherein R 1 is an alkyl group, straight or branched, having at least seven carbon atoms, R 2 is hydrogen or an alkyl group, R 1 and R 2 together having 7-14 carbon atoms, and wherein R 3 is a hydroxyalkyl group of 2-6 carbon atoms, the sum of the carbon atoms in R 1 , R 2 , and R 3 being at least ten; "C" representing CH 2 except for the one carbon atom bearing the said R 1 R 2 substitution, or (b) an orally acceptable acid addition salt thereof, in an amount effective for said purpose.
Claim 20
Dependent Claim
14 words
The method of claim 17, wherein R 1 is a symmetrically branched octyl group.
Claim 21
Dependent Claim
12 words
The method of claim 17 wherein R 2 is hydrogen or methyl.
Claim 22
Dependent Claim
15 words
The method of claim 17 wherein R 1 is n-nonyl and R 3 is 3-hydroxypropyl.
Claim 23
Dependent Claim
15 words
The method of claim 17 wherein the active ingredient is 3-n-nonyl-1-(3-hydroxypropyl) piperidine acid addition salt.
Claim 24
Dependent Claim
13 words
The method of claim 17 wherein the active ingredient is 3-n-nonyl-1-(3-hydroxypropyl) piperidine hydrochloride.
Claim 25
Dependent Claim
15 words
The method of claim 17 wherein R 1 is 2,2-dipropylethyl and R 3 is 2-hydroxyethyl.
Claim 26
Dependent Claim
15 words
The method of claim 17 wherein the active ingredient is 4-(2,2-dipropylethyl)-1-(2-hydroxyethyl) piperidine acid addition salt.
Claim 27
Dependent Claim
13 words
The method of claim 17 wherein the active ingredient is 4-(2,2-dipropylethyl)-1-(2-hydroxyethyl) piperidine hydrochloride.
Claim 28
Dependent Claim
10 words
The method of claim 17 wherein R 3 is omega-hydroxyalkyl.
Claim 29
Dependent Claim
27 words
The method of claim 17 wherein the total number of carbon atoms in R 1 , R 2 , and R 3 is between ten and fifteen.
Claim 30
Dependent Claim
19 words
The method in claim 17 wherein R 1 is selected from the group consisting of n-octyl, n-nonyl, and n-decyl.
Claim 31
Dependent Claim
21 words
The method of claim 17 wherein R 3 is selected from the group consisting of 2-hydroxyethyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl, and 6-hydroxyhexyl.
Claim 32
Dependent Claim
15 words
The method of claim 17 where R 1 is n-octyl and R 3 is 3-hydroxypropyl.
Claim 33
Dependent Claim
15 words
The method of claim 17 wherein the active ingredient is a 4-n-octyl-1-(3-hydroxypropyl)piperidine acid addition salt.
Claim 34
Dependent Claim
14 words
The method of claim 17, wherein both R 1 and R 2 are alkyl.
Claim 35
Dependent Claim
50 words
A compound selected from the group consisting of (a) an alkyl 1-hydroxyalkyl piperidine having the formula B ##STR36## wherein R 1 is selected from the group consisting of 2,2-dipropylethyl and 2-ethyl-3-propylbutyl, R 2 is hydrogen, and R 3 is omega-hydroxyethyl or omega-hydroxypropyl, and (b) an orally-acceptable acid addition salt thereof.
Claim 36
Dependent Claim
50 words
A compound selected from the group consisting of (a) an alkyl 1-hydroxyalkyl piperidine having the formula B ##STR36## wherein R 1 is selected from the group consisting of 2,2-dipropylethyl and 2-ethyl-3-propylbutyl, R 2 is hydrogen, and R 3 is omega-hydroxyethyl or omega-hydroxypropyl, and (b) an orally-acceptable acid addition salt thereof.
Claim 37
Dependent Claim
10 words
The compound of claim 33 wherein R 1 is 2,2-dipropylethyl.
Claim 38
Dependent Claim
10 words
The compound of claim 33 wherein R 1 is 2-ethyl-3-propylbutyl.
Claim 39
Dependent Claim
10 words
The compound of claim 33 wherein R 3 is 2-hydroxyethyl.
Claim 40
Dependent Claim
10 words
The compound of claim 33 wherein R 3 is 3-hydroxypropyl.
Claim 41
Dependent Claim
12 words
The compound of claim 33 which is 4-(2,2-dipropylethyl)-1-(3-hydroxypropyl) piperidine acid addition salt.
Claim 42
Dependent Claim
12 words
The compound of claim 33 which is 4-(2,2-dipropylethyl)-1-(2-hydroxyethyl) piperidine acid addition salt.
Claim 43
Dependent Claim
9 words
The compound of claim 33 which is 4-(2,2-dipropylethyl)-1-(2-hydroxyethyl)piperidine hydrochloride.
Claim 44
Dependent Claim
12 words
The compound of claim 33 which is 4-(2-ethyl-3-propylbutyl)-1-(3-hydroxypropyl) piperidine acid addition salt.
Claim 45
Dependent Claim
9 words
The compound of claim 33 which is 4-(2,2-dipropylethyl)-1-(3-hydroxypropyl)piperidine hydrochloride.
Claim 46
Dependent Claim
9 words
The compound of claim 33 which is 4-(2-ethyl-3-propylbutyl)-1-(3-hydroxypropyl)piperidine hydrochloride.
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) | 1983-11-25 | 1984-05-26 | 1984-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-25 | 1988-05-26 | 1988-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-25 | 1992-05-26 | 1992-11-25 | $7700.00 | Window Closed / Lapsed |