US4464531A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4-Carbamoylimidazolium-5-olate derivatives
Assignee: Sumitomo Chemical Co Ltd
•
Filing: 1982-04-07
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Granted: 1984-08-07
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Expires: 2002-04-07
Abstract
Abstract There are provided compounds of the formula: <IMAGE> +TR <IMAGE> <IMAGE> +TR <IMAGE> wherein either R1 or R2 is a hydrogen atom, a hydroxy group, an acyloxy group, a phthalimido group or an acetamido group and the other is a hydrogen atom; either R3 or R4 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R5 or R6 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R7 or R8 is a hydrogen atom, a methyl group, a hydroxymethyl group, an acyloxymethyl group, an alkoxycarbonyl group, a group of the formula: <IMAGE> (wherein X1 and X2 are a hydrogen atom or a lower alkyl group), or a carboxyl group and the other is a hydrogen atom; either R11 or R12 is a hydrogen atom, a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R13 or R14 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R15 or R16 is a methyl group, a hydroxymethyl group or an acyloxymethyl group and the other is a hydrogen atom; and a process for producing them. These compounds are useful as antitumor agents.
Inventors
- 👤 Toshio Atsumi
- 👤 Yuzo Tarumi
- 👤 Tetsutaro Sanjiki
- 👤 Yoshiaki Takebayashi
- 👤 Noboru Yoshida
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 23:10
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/02
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
277 words
A compound selected from the group consisting of compounds of the formulae: ##STR15## wherein one of R 1 and R 2 is selected from the group consisting of hydrogen, hydroxy, acyloxy, phthalimido and acetamido and the other is hydrogen; one of R 3 and R 4 is selected from the group consisting of hydroxy and acyloxy and the other is hydrogen; one of R 5 and R 6 is selected from the group consisting of hydroxy and acyloxy and the other is hydrogen; one of R 7 and R 8 is selected from the group consisting of hydrogen, methyl, hydroxymethyl, acyloxymethyl, alkoxycarbonyl of 1 to 4 carbon atoms in the alkoxy group, a group of the formula: ##STR16## (wherein X 1 and X 2 are selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms) and carboxyl and the other is hydrogen; one of R 11 and R 12 is selected from the group consisting of hydrogen, hydroxy and acyloxy and the other is hydrogen; one of R 13 and R 14 is selected from the group consisting of hydroxy and acyloxy and the other is hydrogen; one of R 15 and R 16 is selected from the group consisting of methyl, hydroxymethyl and acyloxymethyl and the other is hydrogen, wherein all of said acyloxy groups, including the acyloxy groups of said acyloxymethyl groups, are selected from the group consisting of alkanoyloxy of 2 to 7 carbon atoms and benzoyloxy, said benzoyloxy being unsubstituted or substituted by a member selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro and halogen.
Claim 2
Dependent Claim
277 words
A compound selected from the group consisting of compounds of the formulae: ##STR15## wherein one of R 1 and R 2 is selected from the group consisting of hydrogen, hydroxy, acyloxy, phthalimido and acetamido and the other is hydrogen; one of R 3 and R 4 is selected from the group consisting of hydroxy and acyloxy and the other is hydrogen; one of R 5 and R 6 is selected from the group consisting of hydroxy and acyloxy and the other is hydrogen; one of R 7 and R 8 is selected from the group consisting of hydrogen, methyl, hydroxymethyl, acyloxymethyl, alkoxycarbonyl of 1 to 4 carbon atoms in the alkoxy group, a group of the formula: ##STR16## (wherein X 1 and X 2 are selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms) and carboxyl and the other is hydrogen; one of R 11 and R 12 is selected from the group consisting of hydrogen, hydroxy and acyloxy and the other is hydrogen; one of R 13 and R 14 is selected from the group consisting of hydroxy and acyloxy and the other is hydrogen; one of R 15 and R 16 is selected from the group consisting of methyl, hydroxymethyl and acyloxymethyl and the other is hydrogen, wherein all of said acyloxy groups, including the acyloxy groups of said acyloxymethyl groups, are selected from the group consisting of alkanoyloxy of 2 to 7 carbon atoms and benzoyloxy, said benzoyloxy being unsubstituted or substituted by a member selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro and halogen.
Claim 3
Dependent Claim
49 words
A compound according to claim 1 which is selected from the group consisting of compounds of the formulae: ##STR17## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in claim 1.
Claim 4
Dependent Claim
43 words
A compound according to claim 1 which is selected from the group consisting of compounds of the formulae: ##STR18## wherein R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are as defined in claim 1.
Claim 5
Dependent Claim
1 words
4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 6
Dependent Claim
1 words
4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 7
Dependent Claim
1 words
4-β-D-glucopyranosyloxy-1H-imidazole-5-carboxamide.
Claim 8
Dependent Claim
1 words
4-β-D-glucopyranosyloxy-1H-imidazole-5-carboxamide.
Claim 9
Dependent Claim
1 words
4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 10
Dependent Claim
1 words
4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 11
Dependent Claim
1 words
4-β-D-galactopyranosyloxy-1H-imidazole-5-carboxamide.
Claim 12
Dependent Claim
1 words
4-β-D-galactopyranosyloxy-1H-imidazole-5-carboxamide.
Claim 13
Dependent Claim
1 words
4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 14
Dependent Claim
1 words
4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 15
Dependent Claim
1 words
4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 16
Dependent Claim
1 words
4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 17
Dependent Claim
1 words
4-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 18
Dependent Claim
1 words
4-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 19
Dependent Claim
1 words
4-α-L-rhamnopyranosyloxy-1H-imidazole-5-carboxamide.
Claim 20
Dependent Claim
1 words
4-α-L-rhamnopyranosyloxy-1H-imidazole-5-carboxamide.
Claim 21
Dependent Claim
1 words
4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 22
Dependent Claim
1 words
4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 23
Dependent Claim
1 words
4-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 24
Dependent Claim
1 words
4-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 25
Dependent Claim
2 words
Methyl 1-O-(5-carbamoyl-1H-imidazole-4-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate.
Claim 26
Dependent Claim
2 words
Methyl 1-O-(5-carbamoyl-1H-imidazole-4-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate.
Claim 27
Dependent Claim
2 words
Methyl 1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyranuronate.
Claim 28
Dependent Claim
2 words
Methyl 1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyranuronate.
Claim 29
Dependent Claim
1 words
1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyranuronamide.
Claim 30
Dependent Claim
1 words
1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyranuronamide.
Claim 31
Dependent Claim
1 words
N-methyl[1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyran]uronamide.
Claim 32
Dependent Claim
1 words
N-methyl[1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyran]uronamide.
Claim 33
Dependent Claim
2 words
Ammonium 1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyranuronate.
Claim 34
Dependent Claim
2 words
Ammonium 1-O-(5-carbamoyl-1H-imidazole-4-yl)-β-D-glucopyranuronate.
Claim 35
Dependent Claim
1 words
4-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 36
Dependent Claim
1 words
4-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 37
Dependent Claim
1 words
4-α-D-arabinofuranosyloxy-1H-imidazole-5-carboxamide.
Claim 38
Dependent Claim
1 words
4-α-D-arabinofuranosyloxy-1H-imidazole-5-carboxamide.
Claim 39
Dependent Claim
1 words
4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 40
Dependent Claim
1 words
4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)oxy-1H-imidazole-5-carboxamide.
Claim 41
Dependent Claim
1 words
4-β-D-ribofuranosyloxy-1H-imidazole-5-carboxamide.
Claim 42
Dependent Claim
1 words
4-β-D-ribofuranosyloxy-1H-imidazole-5-carboxamide.
References Cited (Backward Citations)
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US4260774A
Cited
US4248999A
Cited
US4140788A
Cited
US4218457A
Cited
US4317825A
Cited
US4332806A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-08-07 | 1988-02-06 | 1988-08-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-07 | 1992-02-06 | 1992-08-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-07 | 1996-02-06 | 1996-08-07 | $7700.00 | Window Closed / Lapsed |