US4708959A
Expired / Lapsed
US
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4,5-trimethylene-4-isothiazoline-3-ones and their use as a bactericide and fungicide agent
Assignee: Galderma Research and Development SNC
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Filing: 1983-07-27
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Granted: 1987-11-24
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Expires: 2003-07-27
Abstract
Abstract A 4,5-trimethylene-4-isothiazoline-3-one of the formula ##STR1## wherein R 1 represents (i) hydrogen, (ii) alkyl having 1-12 carbon atoms, (iii) alkyl having 2 or 3 carbon atoms and substituted by one or two hydroxy groups, (iv) alkenyl having 3 to 6 carbon atoms, (v) ##STR2## wherein n is 0 or 1, m is 1 or 2, R 1 is hydrogen or lower alkyl having from 1 to 5 carbon atoms and R 2 is hydrogen, lower alkyl, nitro, trifluoromethyl or halogen, (vi) cycloalkyl having 3 to 6 carbon atoms and (vii) ##STR3## wherein R 3 is hydrogen, alkyl having 1-12 carbon atoms or ##STR4## defined above, or the salt thereof with a mineral or organic acid. These compounds are useful as bactericides or fungicides.
Inventors
- 👤 Braham Shroot
- 👤 Jean Maignan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 23:21
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/04; A; A01; A01N; A01N43/00; A01N43/72; A01N43/80; A61; A61P; A61P31/00; A61P31/04; A61P31/10
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
38 words
A 4,5-trimethylene-4-isothiazoline-3-one having the formula ##STR19## wherein R 1 is selected from the group consisting of hydrogen and linear or branched alkyl having from 1 to 12 carbon atoms, and their salts of a mineral or organic acid.
Claim 2
Dependent Claim
38 words
A 4,5-trimethylene-4-isothiazoline-3-one having the formula ##STR19## wherein R 1 is selected from the group consisting of hydrogen and linear or branched alkyl having from 1 to 12 carbon atoms, and their salts of a mineral or organic acid.
Claim 3
Dependent Claim
52 words
The 4,5-trimethylene-4-isothiazoline-3-one of claim 1 selected from the group consisting of: (1) 4,5-trimethylene-4-isothiazoline-3-one, (2) the hydrochloride of (1), (3) 2-methyl-4,5-trimethylene-4-isothiazoline-3-one, (4) the hydrochloride of (3), (5) 2-ethyl-4,5-trimethylene-4-isothiazoline-3-one, (6) 2-propyl-4,5-trimethylene-4-isothiazoline-3-one, (7) 2-isopropyl-4,5-trimethylene-4-isothiazoline-3-one, (8) the hydrochloride of (7), (9) 2-butyl-4,5-trimethylene-4-isothiazoline-3-one, (10) the hydrochloride of (9), (11) 2-isobutyl-4,5-trimethylene-4-isothiazoline-3-one, (12) 2-tert.butyl-4,5-trimethylene-4-isothiazoline-3-one, (13) 2-hexyl-4,5-trimethylene-4-isothiazoline-3-one and (14) 2-octyl-4,5-trimethylene-4-isothiazoline-3-one.
Claim 4
Dependent Claim
20 words
The 4,5-trimethylene-4-isothiazoline-3-one of claim 1 wherein R 1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert.butyl, hexyl, octyl or dodecyl.
Claim 5
Dependent Claim
24 words
The 4,5-trimethylene-4-isothiazoline-3-one of claim 1 in the form of a salt selected from a hydrochloride, a hydrobromide, a nitrate, a sulfate or a succinate.
Claim 6
Dependent Claim
12 words
An anti-bacteria, anti-fungus or anti-acne agent comprising the 4,5-trimethylene-4-isothiazoline-3-one of claim 1.
Claim 7
Dependent Claim
18 words
A cosmetic composition comprising in a cosmetically acceptable carrier an effective amount of the 4,5-trimethylene-4-isothiazoline-3-one of claim 1.
Claim 8
Dependent Claim
30 words
The cosmetic composition of claim 6 wherein said 4,5-trimethylene-4-isothiazoline-3-one is present in an amount ranging from 0.1 to 10 percent by weight based on the total weight of said composition.
Claim 9
Dependent Claim
23 words
A pharmaceutical composition for human or veterinary use comprising in a pharmaceutically acceptable carrier an effective amount of the 4,5-trimethylene-4-isothiazoline-3-one of claim 1.
Claim 10
Dependent Claim
30 words
The pharmaceutical composition of claim 8 wherein said 4,5-trimethylene-4-isothiazoline-3-one is present in an amount ranging from 0.1 to 10 percent by weight based on the total weight of said composition.
Claim 11
Dependent Claim
61 words
A process for preventing or treating infectious bacterial, fungal or acneal diseases of the epidermis comprising administering to a human an effective amount of a 4,5-trimethylene-4-isothiazoline-3-one having the formula: ##STR20## wherein R 1 is selected from the group consisting of hydrogen and linear or branched alkyl having 1 to 12 carbon atoms, and its salt of a mineral or organic acid.
Claim 12
Dependent Claim
61 words
A process for preventing or treating infectious bacterial, fungal or acneal diseases of the epidermis comprising administering to a human an effective amount of a 4,5-trimethylene-4-isothiazoline-3-one having the formula: ##STR20## wherein R 1 is selected from the group consisting of hydrogen and linear or branched alkyl having 1 to 12 carbon atoms, and its salt of a mineral or organic acid.
Claim 13
Dependent Claim
56 words
The process of claim 10 wherein said 4,5-trimethylene-4-isothiazoline-3-one is selected from the group consisting of: (1) 4,5-trimethylene-4-isothiazoline-3-one, (2) the hydrochloride of (1), (3) 2-methyl-4,5-trimethylene-4-isothiazoline-3-one, (4) the hydrochloride of (3), (5) 2-ethyl-4,5-trimethylene-4-isothiazoline-3-one, (6) 2-propyl-4,5-trimethylene-4-isothiazoline-3-one, (7) 2-isopropyl-4,5-trimethylene-4-isothiazoline-3-one, (8) the hydrochloride of (7), (9) 2-butyl-4,5-trimethylene-4-isothiazoline-3-one, (10) the hydrochloride of (9), (11) 2-isobutyl-4,5-trimethylene-4-isothiazoline-3-one, (12) 2-tert.butyl-4,5-trimethylene-4-isothiazoline-3-one, (13) 2-hexyl-4,5-trimethylene-4-isothiazoline-3-one and (14) 2-octyl-4,5-trimethylene-4-isothiazoline-3-one.
Claim 14
Dependent Claim
23 words
The process of claim 10 where in said 4,5-trimethylene-4-isothiazoline-3-one R 1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert.butyl, hexyl, octyl or dodecyl.
Claim 15
Dependent Claim
28 words
The process of claim 10 wherein said 4,5-trimethylene-4-isothiazoline-3-one is in the form of a salt selected from a hydrochloride, a hydrobromide, a nitrate, a sulfate or a succinate.
Claim 16
Dependent Claim
29 words
A 4,5-trimethylene-4-isothiazoline-3-one selected from the group consisting of: (1) 4,5-trimethylene-4-isothiazoline-3-one, (2) the hydrochloride of (1), (3) 2-methyl-4,5-trimethylene-4-isothiazoline-3-one, (4) 2-isopropyl-4,5-trimethylene-4-isothiazoline-3-one, (5) 2-butyl-4,5-trimethylene-4-isothiazoline-3-one, (6) the hydrochloride of (5) and (7) 2-octyl-4,5-trimethylene-4-isothiazoline-3-one.
Claim 17
Dependent Claim
29 words
A 4,5-trimethylene-4-isothiazoline-3-one selected from the group consisting of: (1) 4,5-trimethylene-4-isothiazoline-3-one, (2) the hydrochloride of (1), (3) 2-methyl-4,5-trimethylene-4-isothiazoline-3-one, (4) 2-isopropyl-4,5-trimethylene-4-isothiazoline-3-one, (5) 2-butyl-4,5-trimethylene-4-isothiazoline-3-one, (6) the hydrochloride of (5) and (7) 2-octyl-4,5-trimethylene-4-isothiazoline-3-one.
Claim 18
Dependent Claim
8 words
An anti-bacteria, anti-fungus or anti-acne agent comprising 4,5-trimethylene-4-isothiazoline-3-one.
Claim 19
Dependent Claim
8 words
An anti-bacteria, anti-fungus or anti-acne agent comprising 4,5-trimethylene-4-isothiazoline-3-one.
Claim 20
Dependent Claim
30 words
A cosmetic composition comprising in a cosmetically acceptable carrier 4,5-trimethylene-4-isothiazoline-3-one present in an amount ranging from 0.1 to 10 percent by weight based on the total weight of said composition.
Claim 21
Dependent Claim
30 words
A cosmetic composition comprising in a cosmetically acceptable carrier 4,5-trimethylene-4-isothiazoline-3-one present in an amount ranging from 0.1 to 10 percent by weight based on the total weight of said composition.
Claim 22
Dependent Claim
35 words
A pharmaceutical composition for human or veterinary use comprising in a pharmaceutically acceptable carrier, 4,5-trimethylene-4-isothiazoline-3-one present in an amount ranging from 0.1 to 10 percent by weight based on the total weight of said composition.
Claim 23
Dependent Claim
35 words
A pharmaceutical composition for human or veterinary use comprising in a pharmaceutically acceptable carrier, 4,5-trimethylene-4-isothiazoline-3-one present in an amount ranging from 0.1 to 10 percent by weight based on the total weight of said composition.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-11-23 | 1991-05-25 | 1991-11-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-11-23 | 1995-05-25 | 1995-11-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-11-23 | 1999-05-25 | 1999-11-24 | $7700.00 | Window Closed / Lapsed |