US4293713A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel 1,1,3,5-substituted biuret compound and a pharmaceutical composition containing the same
Assignee: Taiho Pharmaceutical Co Ltd
•
Filing: 1980-03-27
•
Granted: 1981-10-06
•
Expires: 2000-03-27
Abstract
Abstract A novel 1,1,3,5-substituted biuret compound of the formula: ##STR1## wherein R 1 and R 2 are respectively the same or different, and each are alkyl groups having 1 to 4 carbon atoms; R 3 is a cyclohexyl group or a phenyl group which may be unsubstituted or may have at least one substituent selected from the group consisting of chlorine, bromine, fluorine, methyl, trifluoromethyl, dimethylamino, methoxy, methylthio, nitro and acetyl. The novel 1,1,3,5-substituted biuret compounds are useful as an analgesic, anti-inflammatory and/or anti-pyretic agent.
Inventors
- 👤 Hajime Fujimura
- 👤 Yasuzo Hiramatsu
- 👤 Takahiro Yabuuchi
- 👤 Masakatu Hisaki
- 👤 Katsuo Takikawa
- 👤 Takaji Honna
- 👤 Hidekazu Miyake
- 👤 Makoto Kajitani
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 20:50
CPC Classifications
C; C07; C07C; C07C275/00; C07C275/46; C07C275/58; C07C275/62; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
47 words
A 1,1,3-trimethyl-5-substituted biuret compound of the formula: ##STR42## wherein R 3 is a cyclohexyl group or a phenyl group which may be unsubstituted or may have at least one substituent selected from the group consisting of chlorine, bromine, fluorine, methyl, trifluoromethyl, dimethylamino, methoxy, methylthio, nitro and acetyl.
Claim 2
Dependent Claim
47 words
A 1,1,3-trimethyl-5-substituted biuret compound of the formula: ##STR42## wherein R 3 is a cyclohexyl group or a phenyl group which may be unsubstituted or may have at least one substituent selected from the group consisting of chlorine, bromine, fluorine, methyl, trifluoromethyl, dimethylamino, methoxy, methylthio, nitro and acetyl.
Claim 3
Dependent Claim
12 words
Compound of claim 1, wherein R 3 is substituted or unsubstituted phenyl.
Claim 4
Dependent Claim
6 words
1,1,3-Trimethyl-5-phenylbiuret as claimed in claim 1.
Claim 5
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2-fluorophenyl)biuret as claimed in claim 1.
Claim 6
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-fluorophenyl)biuret as claimed in claim 1.
Claim 7
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2,3,5,6-tetrafluorophenyl)biuret as claimed in claim 1.
Claim 8
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2-chlorophenyl)biuret as claimed in claim 1.
Claim 9
Dependent Claim
6 words
1,1,3-Trimethyl-5-(3-chlorophenyl)biuret as claimed in claim 1.
Claim 10
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-chlorophenyl)biuret as claimed in claim 1.
Claim 11
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2,4-dichlorophenyl)biuret as claimed in claim 1.
Claim 12
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2,6-dichlorophenyl)biuret as claimed in claim 1.
Claim 13
Dependent Claim
6 words
1,1,3-Trimethyl-5-(3,4-dichlorophenyl)biuret as claimed in claim 1.
Claim 14
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-bromophenyl)biuret as claimed in claim 1.
Claim 15
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2-trifluoromethylphenyl)-biuret as claimed in claim 1.
Claim 16
Dependent Claim
6 words
1,1,3-Trimethyl-5-(3-trifluoromethylphenyl)-biuret as claimed in claim 1.
Claim 17
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-dimethylaminophenyl)-biuret as claimed in claim 1.
Claim 18
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-nitrophenyl)biuret as claimed in claim 1.
Claim 19
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2-methyoxyphenyl)biuret as claimed in claim 1.
Claim 20
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-methoxyphenyl)biuret as claimed in claim 1.
Claim 21
Dependent Claim
6 words
1,1,3-Trimethyl-5-(3,4-dimethoxyphenyl)biuret as claimed in claim 1.
Claim 22
Dependent Claim
6 words
1,1,3-Trimethyl-5-(3,4,5-trimethoxyphenyl)biuret as claimed in claim 1.
Claim 23
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2-methylphenyl)biuret as claimed in claim 1.
Claim 24
Dependent Claim
6 words
1,1,3-Trimethyl-5-(3-methylphenyl)biuret as claimed in claim 1.
Claim 25
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-methylphenyl)biuret as claimed in claim 1.
Claim 26
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2,3-dimethylphenyl)biuret as claimed in claim 1.
Claim 27
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2,6-dimethylphenyl)biuret as claimed in claim 1.
Claim 28
Dependent Claim
6 words
1,1,3-Trimethyl-5-(3,4-dimethylphenyl)biuret as claimed in claim 1.
Claim 29
Dependent Claim
6 words
1,1,3-Trimethyl-5-(2-methyl-3-chlorophenyl)-biuret as claimed in claim 1.
Claim 30
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-acetylphenyl)biuret as claimed in claim 1.
Claim 31
Dependent Claim
6 words
1,1,3-Trimethyl-5-(4-methylthiophenyl)biuret as claimed in claim 1.
Claim 32
Dependent Claim
6 words
1,1,3-Trimethyl-5-cyclohexylbiuret as claimed in claim 1.
Claim 33
Dependent Claim
67 words
A process for preparing the substituted biuret compound of claim 1, said process comprising reacting an allophanoyl chloride of formula (4). ##STR43## wherein R 1 and R 2 are defined in claim 1, with an amine of formula (5) R.sup.3 --NH (5) wherein R 3 is defined in claim 1, at a temperature of about -20° C. to about 50° C. to produce said 1,1,3,5-substituted biuret compound.
Claim 34
Dependent Claim
65 words
A process for preparing the 1,1,3,5-substituted biuret compound of claim 1, said process comprising reacting an allophanoyl chloride of formula (6) ##STR44## wherein R 2 and R 3 are defined in claim 1, with an amine of formula (7) ##STR45## wherein R 1 is defined in claim 1, at a temperature of about -20° C. to about 50° C. to produce said 1,1,3,5-substituted biuret compound.
References Cited (Backward Citations)
US3253902A
Cited
US3149338A
Cited
US3189431A
Cited
US3305549A
Cited
GB1096006A
Cited
US3407193A
Cited
US3556766A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-05 | 1985-04-06 | 1985-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-05 | 1989-04-06 | 1989-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-05 | 1993-04-06 | 1993-10-06 | $7700.00 | Window Closed / Lapsed |