US4421749A
Expired / Lapsed
US
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Aluminum pyridinethiols as antimicrobials
Assignee: F Hoffmann La Roche AG
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Filing: 1981-06-26
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Granted: 1983-12-20
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Expires: 2001-06-26
Abstract
Abstract Organoaluminum compounds of the formula ##STR1## wherein m, n and R are as defined hereinafter, and processes for their preparation are disclosed. The compounds of formula I possess antimicrobial properties and are useful in cosmetic compositions, such as hair-care compositions and foot-care compositions.
Inventors
- 👤 Horst Pauling
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 14:05
CPC Classifications
C; C07; C07F; C07F5/00; C07F5/06; C07F5/069; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/4906; A61K8/4933; A61P; A61P31/00; A61P31/04; A61Q; A61Q17/00; A61Q17/005; A61Q5/00; A61Q5/006; C07D; C07D213/00; C07D213/02; C07D213/89; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/576; C07F9/58; Y; Y10; Y10S; Y10S424/00; Y10S424/04
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
99 words
A compound of the formula ##STR8## wherein m is 1 or 2, n is 1 or 2, whereby the sum m+n is 3, and R is ethyl or n-hexadecyl; straight-chain or branched C 1-4 -alkyl monosubstituted with phenoxy; 2,4-hexadienoyl; unsubstituted phenyl or phenyl substituted with 1 to 5 chlorine atoms or a phenyl group; or a group of the formula ##STR9## wherein R 1 is C 1-6 -alkyl, or, where m is 1 and n is 2, the two R-symbols together form a 2,2'-methylene-bis-(3,4,6-trichloro-o-phenylene)group, or, where m is 2 and n is 1, R is a 2,4,5-trichloro-6-[2,3,5-trichloro-6-[di(2-pyridinethiolato)aluminum]oxy-benzyl]phenyl N,N'-dioxide group.
Claim 2
Dependent Claim
99 words
A compound of the formula ##STR8## wherein m is 1 or 2, n is 1 or 2, whereby the sum m+n is 3, and R is ethyl or n-hexadecyl; straight-chain or branched C 1-4 -alkyl monosubstituted with phenoxy; 2,4-hexadienoyl; unsubstituted phenyl or phenyl substituted with 1 to 5 chlorine atoms or a phenyl group; or a group of the formula ##STR9## wherein R 1 is C 1-6 -alkyl, or, where m is 1 and n is 2, the two R-symbols together form a 2,2'-methylene-bis-(3,4,6-trichloro-o-phenylene)group, or, where m is 2 and n is 1, R is a 2,4,5-trichloro-6-[2,3,5-trichloro-6-[di(2-pyridinethiolato)aluminum]oxy-benzyl]phenyl N,N'-dioxide group.
Claim 3
Dependent Claim
32 words
A compound according to claim 1, wherein R is straight-chain or branched C 1-4 -alkyl monosubstituted with phenoxy, 2,4-hexadienoyl, optionally substituted phenyl, a group of formula (a) or the 2,4,5-trichloro-6-[2,3,5-trichloro-6-[di(2-pyridinethiolato)aluminum]oxy-benzyl]phenyl N,N'-dioxide group.
Claim 4
Dependent Claim
16 words
A compound according to claim 1 or 2, wherein m is 1 and n is 2.
Claim 5
Dependent Claim
8 words
A compound according to claim 1, (2-phenoxyethoxy)bis(2-pyridinethiolato)aluminum N,N'-dioxide.
Claim 6
Dependent Claim
8 words
A compound according to claim 1, bis(ethylphosphonato)(2-pyridinethiolato)aluminum N-oxide.
Claim 7
Dependent Claim
8 words
A compound according to claim 1, (2-biphenylyloxy)bis(2-pyridinethiolato)aluminum N,N'-dioxide.
Claim 8
Dependent Claim
10 words
A compound according to claim 1, [methylene-bis(3,4,6-trichloro-o-phenyleneoxy)]bis[(di-2-pyridinethiolato)]aluminum N,N', N", N"'-tetroxide.
Claim 9
Dependent Claim
39 words
A compound according to claim 1, selected from the group consisting of: Ethoxy-bis(2-pyridinethiolato)aluminum N,N'-dioxide, (2,4,6-trichlorophenoxy)bis(2-pyridinethiolato)aluminum N,N'-dioxide, (1-hexadecanolato)bis(2-pyridinethiolato)aluminum N,N'dioxide, [methylene-bis(3,4,6-trichloro-o-phenyleneoxy)](2-pyridinethiolato)aluminum N-oxide, Bis(2-phenoxyethoxy)(2-pyridinethiolato)aluminum N-oxide, diphenoxy(2-pyridinethiolato)aluminum N-oxide, bis(2-biphenylyloxy)(2-pyridinethiolato)aluminum N-oxide, bis(n-butylphosphonato)(2-pyridinethiolato)aluminum N-oxide, (n-butylphosphonato)bis(2-pyridinethiolato)aluminum N,N'-dioxide, (ethylphosphonato)bis(2-pyridinethiolato)aluminum N,N'-dioxide, (sorbato)bis(2-pyridinethiolato)aluminum N,N'-dioxide, phenoxy-bis(2-pyridinethiolato)aluminum N,N'-dioxide and pentachlorophenoxy-bis(2-pyridinethiolato)aluminum N,N'-dioxide.
Claim 10
Dependent Claim
115 words
An antimicrobial cosmetic composition, comprising a cosmetic base and an antimicrobially-effective amount of at least one compound of the formula ##STR10## wherein m is 1 or 2, n is 1 or 2, whereby the sum m+n is 3, and R is ethyl or n-hexadecyl; straight-chain or branched C 1-4 -alkyl monosubstituted with phenoxy; 2,4-hexadienoyl; unsubstituted phenyl or phenyl substituted with 1 to 5 chlorine atoms or a phenyl group; or a group of the formula ##STR11## wherein R 1 is C 1-6 -alkyl, or, where m is 1 and n is 2, the two R-symbols together form a 2,2'-methylene-bis(3,4,6-trichloro-o-phenylene) group, or, where m is 2 and n is 1, R is a 2,4,5-trichloro-6-[2,3,5-trichloro-6-[di(2-pyridinethiolato)aluminum]oxy-benzyl]phenyl N,N'-dioxide group.
Claim 11
Dependent Claim
115 words
An antimicrobial cosmetic composition, comprising a cosmetic base and an antimicrobially-effective amount of at least one compound of the formula ##STR10## wherein m is 1 or 2, n is 1 or 2, whereby the sum m+n is 3, and R is ethyl or n-hexadecyl; straight-chain or branched C 1-4 -alkyl monosubstituted with phenoxy; 2,4-hexadienoyl; unsubstituted phenyl or phenyl substituted with 1 to 5 chlorine atoms or a phenyl group; or a group of the formula ##STR11## wherein R 1 is C 1-6 -alkyl, or, where m is 1 and n is 2, the two R-symbols together form a 2,2'-methylene-bis(3,4,6-trichloro-o-phenylene) group, or, where m is 2 and n is 1, R is a 2,4,5-trichloro-6-[2,3,5-trichloro-6-[di(2-pyridinethiolato)aluminum]oxy-benzyl]phenyl N,N'-dioxide group.
Claim 12
Dependent Claim
15 words
The antimicrobial cosmetic composition according to claim 9, comprising an antimicrobially-effective amount of (2-phenoxyethoxy)bis(2-pyridinethiolato)aluminum N,N'-dioxide.
Claim 13
Dependent Claim
15 words
An antimicrobial cosmetic composition according to claim 9, comprising an antimicrobially-effective amount of bis(ethylphosphonato)(2-pyridinethiolato)aluminum N-oxide.
Claim 14
Dependent Claim
15 words
An antimicrobial cosmetic composition according to claim 9, comprising an antimicrobially-effective amount of (2-biphenylyloxy)bis(2-pyridinethiolato)aluminum N,N'-dioxide.
Claim 15
Dependent Claim
17 words
An antimicrobial cosmetic composition according to claim 9, comprising an antimicrobially-effective amount of [methylene-bis(3,4,6-trichloro-o-phenyleneoxy)]bis[(di-2-pyridinethiolato)]aluminum N,N', N", N"'-tetroxide.
Claim 16
Dependent Claim
29 words
A method for the control or prevention of dandruff of the scalp, which comprises treating the scalp with an effective amount of the cosmetic composition according to claim 9.
Claim 17
Dependent Claim
29 words
A method for the control or prevention of dandruff of the scalp, which comprises treating the scalp with an effective amount of the cosmetic composition according to claim 10.
Claim 18
Dependent Claim
29 words
A method for the control or prevention of dandruff of the scalp, which comprises treating the scalp with an effective amount of the cosmetic composition according to claim 11.
Claim 19
Dependent Claim
29 words
A method for the control or prevention of dandruff of the scalp, which comprises treating the scalp with an effective amount of the cosmetic composition according to claim 12.
Claim 20
Dependent Claim
29 words
A method for the control or prevention of dandruff of the scalp, which comprises treating the scalp with an effective amount of the cosmetic composition according to claim 13.
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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) | 1986-12-19 | 1987-06-20 | 1987-12-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-19 | 1991-06-20 | 1991-12-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-19 | 1995-06-20 | 1995-12-20 | $7700.00 | Window Closed / Lapsed |