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US4156729A
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1,2-Benzisothiazolin-3-ones
Assignee: Bayer AG
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Filing: 1977-01-19
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Granted: 1979-05-29
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Expires: 1997-01-19
Abstract
Abstract 6-Substituted-1,2-benzisothiazolin-3-ones carrying an aminoalkyl group in the 2-position and being optionally substituted in the 4- and/or 5-position are antithrombotic agents. The compounds, of which 2-(2-diethylaminoethyl)-4,5-dimethyl-1,2-benzisothiazolin-3-one is a representative embodiment, can be prepared by cyclization of an appropriately substituted bis-[2-(aminoalkylcarbamyl)phenyl]disulfide, or by other disclosed methods.
Inventors
- 👤 Horst Boshagen
- 👤 Ulrich Horlein
- 👤 Karl-August Meng, deceased
- 👤 Friedel Seuter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 15:01
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/04; A; A61; A61P; A61P7/00; A61P7/02; C07C; C07C323/00; C07D417/00; C07D417/02; C07D417/06
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
180 words
A compound selected from the group consisting of 6-substituted 7-unsubstituted 1,2-benzisothiazolin-3-ones depicted by the formula: ##STR48## and the pharmaceutically acceptable acid addition salts thereof wherein R 1 when taken independently of R 2 is chloro, bromo, fluoro, nitro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or an aromatic substituent selected from the group consisting of phenoxy, benzyloxy and phenylthio which aromatic substituent is unsubstituted or nonsubstituted with alkyl of 1 to 4 carbon atoms or halo; R 2 when taken independently of R 1 is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; R 1 and R 2 taken together are trimethylene, tetramethylene or pentamethylene; R 3 is hydrogen, halo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; each of R 4 and R 5 is alkyl of 1 to 4 carbon atoms; and A is alkylene of 2 to 5 carbon atoms, alkylenoxyalkyl of 4 to 8 carbon atoms or alkylenethioalkyl of 4 to 8 carbon atoms.
Claim 2
Dependent Claim
180 words
A compound selected from the group consisting of 6-substituted 7-unsubstituted 1,2-benzisothiazolin-3-ones depicted by the formula: ##STR48## and the pharmaceutically acceptable acid addition salts thereof wherein R 1 when taken independently of R 2 is chloro, bromo, fluoro, nitro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or an aromatic substituent selected from the group consisting of phenoxy, benzyloxy and phenylthio which aromatic substituent is unsubstituted or nonsubstituted with alkyl of 1 to 4 carbon atoms or halo; R 2 when taken independently of R 1 is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; R 1 and R 2 taken together are trimethylene, tetramethylene or pentamethylene; R 3 is hydrogen, halo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; each of R 4 and R 5 is alkyl of 1 to 4 carbon atoms; and A is alkylene of 2 to 5 carbon atoms, alkylenoxyalkyl of 4 to 8 carbon atoms or alkylenethioalkyl of 4 to 8 carbon atoms.
Claim 3
Dependent Claim
39 words
A compound according to claim 1 wherein R 1 taken independently of R 2 is chloro, nitro, methyl, methoxy, ethoxy, butoxy, phenoxy, benzyloxy, phenylthio or chlorophenylthio; R 2 is hydrogen or methoxy; and R 3 is hydrogen or methyl.
Claim 4
Dependent Claim
28 words
A compound according to claim 2 wherein A is ethylene, trimethylene, tetramethylene, 1-methyltetramethylene, ethylenoxyethyl or ethylenethioethyl; and each of R 4 and R 5 is methyl or ethyl.
Claim 5
Dependent Claim
40 words
A compound according to claim 1 wherein R 1 is chloro or methyl; R 2 is hydrogen; R 3 is hydrogen or methyl; A is ethylene or trimethylene and each of R 4 and R 5 is methyl or ethyl.
Claim 6
Dependent Claim
11 words
A compound according to claim 1 wherein said 1,2-benzisothiazolin-3-one is 2-(3-dimethylaminopropyl)-6-chloro-1,2-benzisothiazolin-3-one.
Claim 7
Dependent Claim
11 words
A compound according to claim 1 wherein said 1,2-benzisothiazolin-3-one is 2-(2-diethylaminoethyl)-6-chloro-1,2-benzisothiazolin-3-one.
Claim 8
Dependent Claim
11 words
A compound according to claim 1 wherein said 1,2-benzisothiazolin-3-one is 2-(2-diethylaminoethyl)-4,6-dimethyl-1,2-benzisothiazolin-3-one.
Claim 9
Dependent Claim
11 words
A compound according to claim 1 wherein said 1,2-benzisothiazolin-3-one is 2-(3-diethylaminopropyl)-4,6-dimethyl-1,2-benzisothiazolin-3-one.
Claim 10
Dependent Claim
11 words
A compound according to claim 1 wherein said 1,2-benzisothiazolin-3-one is 2-(3-dimethylaminopropyl)-4,6-dimethyl-1,2-benzisothiazolin-3-one.
Claim 11
Dependent Claim
63 words
A compound according to claim 1 which is a salt of said 1,2-benzoisothiazolin-3-one with an acid selected from the group consisting of oxalic acid, 1,5-naphthalenedisulfonic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, methanesulphonic acid, acetic acid, tartaric acid, lactic acid, succinic acid, citric acid, malic acid, maleic acid, sorbic acid, aconitic acid, salicyclic acid, phthalic acid, embonic acid, and enanthic acid.
Claim 12
Dependent Claim
35 words
The method of achieving an antithrombotic effect in a human or other warm blooded animal in need thereof which consists essentially of administering thereto an antithrombotically effective amount of a compound according to claim 1.
Claim 13
Dependent Claim
24 words
A pharmaceutical composition consisting essentially of an antithrombotically effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
44 words
A compound according to claim 1 wherein R 1 is halo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; R 2 is hydrogen; and R 3 is hydrogen, halo or alkyl of 1 to 4 carbon atoms.
References Cited (Backward Citations)
US3227715A
Cited
US4113728A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-28 | 1982-11-27 | 1983-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-28 | 1986-11-27 | 1987-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-28 | 1990-11-27 | 1991-05-29 | $7700.00 | Window Closed / Lapsed |