US4691012A
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Sialic acid derivative and process for preparing the same
Assignee: KANTO ISHI PHARMACEUTICAL CO Ltd
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Filing: 1985-03-06
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Granted: 1987-09-01
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Expires: 2005-03-06
Abstract
Abstract A novel N-acetylneuraminic acid derivative, represented by the general formula: ##STR1## wherein the R 1 groups are, independently, hydrogen or acetyl; R 2 is a nucleoside residue; and R 3 is carboxyl or methoxycarbonyl. The N-acetylneuraminic acid derivative is useful in inhibiting metastasis of cancer cells. Also provided is a process for the preparation of the derivatives.
Inventors
- 👤 Haruo Ogura
- 👤 Kimio Furuhata
- 👤 Toshiaki Osawa
- 👤 Satoshi Toyoshima
- 👤 Yoshiyasu Shitori
- 👤 Masayoshi Ito
- 👤 Shoji Yoshimura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 16:57
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
41 words
An N-acetylneuraminic acid represented by the general formula: ##STR7## wherein the R 1 groups are, independently, hydrogen or acetyl; R 2 is selected from the group consisting of uridine, 5-fluoro-uridine, 2', 3'-isopropylidene-uridine and 5-fluoro-2',3-isopropylidene-uridine; and R 3 is carboxyl or methoxycarbonyl.
Claim 2
Dependent Claim
41 words
An N-acetylneuraminic acid represented by the general formula: ##STR7## wherein the R 1 groups are, independently, hydrogen or acetyl; R 2 is selected from the group consisting of uridine, 5-fluoro-uridine, 2', 3'-isopropylidene-uridine and 5-fluoro-2',3-isopropylidene-uridine; and R 3 is carboxyl or methoxycarbonyl.
Claim 3
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is acetyl, R 2 is 2',3'-isopropylideneuridine and R 3 is methoxycarbonyl.
Claim 4
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is hydrogen, R 2 is 2',3'-isopropylideneuridine and R 3 is methoxycarbonyl.
Claim 5
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is hydrogen, R 2 is uridine and R 3 is carboxyl.
Claim 6
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is hydrogen, R 2 is 5-fluoro-2',3'-isopropylideneuridine and R 3 is methoxycarbonyl.
Claim 7
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is acetyl, R 2 is 5-fluoro-2',3'-isopropylideneuridine and R 3 is methoxycarbonyl.
Claim 8
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is hydrogen, R 2 is 5-fluorouridine and R 3 is methoxycarbonyl.
Claim 9
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is hydrogen R 2 is 5-fluorouridine and R 3 is carboxyl.
Claim 10
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is hydrogen, R 2 is uridine and R 3 is methoxycarbonyl.
Claim 11
Dependent Claim
23 words
The N-acetylneuraminic acid derivative as claimed in claim 1, wherein R 1 is acetyl, R 2 is uridine and R 3 is methoxycarbonyl.
Claim 12
Dependent Claim
101 words
A process for preparing an N-acetylneuraminic acid derivative represented by the following formula : ##STR8## wherein the R 1 groups are independently, hydrogen or acetyl; R 2 is selected from the group consisting of uridine, 5-fluoro-uridine, 2,3-isopropylidene-uridine and 5-fluoro-2',3-isopropylideneuridine; and R 3 is carboxyl or methoxycarbonyl; which comprises reacting a compound represented by the general formula: ##STR9## with a compound represented by the formula R 2 -H [III], wherein R 2 is nucleoside residue, in the presence of a catalyst; to produce the reaction product represented by isolating and a formula [I] purifying the reaction product step through a dual-chromatography step.
Claim 13
Dependent Claim
101 words
A process for preparing an N-acetylneuraminic acid derivative represented by the following formula : ##STR8## wherein the R 1 groups are independently, hydrogen or acetyl; R 2 is selected from the group consisting of uridine, 5-fluoro-uridine, 2,3-isopropylidene-uridine and 5-fluoro-2',3-isopropylideneuridine; and R 3 is carboxyl or methoxycarbonyl; which comprises reacting a compound represented by the general formula: ##STR9## with a compound represented by the formula R 2 -H [III], wherein R 2 is nucleoside residue, in the presence of a catalyst; to produce the reaction product represented by isolating and a formula [I] purifying the reaction product step through a dual-chromatography step.
Claim 14
Dependent Claim
38 words
The process as claimed in claim 11, wherein said isolation-purifying step is at least one of the dual-chromatography steps selected from the group consisting of: adsorption chromatography/adsorption chromatography; adsorption chromatography/partition chromatography; partition chromatography/adsorption chromatography; and partition chromatography/partition chromatography.
Claim 15
Dependent Claim
55 words
The process according to claim 12, wherein said adsorption and partition chromatography steps comprise using a column packed with a member selected from the group consisting of silica gel and alumina and elution is accomplished by one or more solvents selected from the group consisting of chloroform, methanol, ethyl acetate, ethanol, benzene, acetone and toluene.
Claim 16
Dependent Claim
34 words
The process as claimed in claim 11, wherein said compound represented by the formula [III] is a compound represented by the general formula: ##STR10## wherein R is hydrogen or fluorine, and Me is methyl.
Claim 17
Dependent Claim
22 words
The process as claimed in claim 11, wherein said reaction product is hydrolyzed before being subjected to said isolating and purifying step.
Claim 18
Dependent Claim
34 words
The process according to claim 15, wherein compound [II] is used in a ratio of at least about 1.2 moles per 1 mole of compound [III] in the step to produce said reaction product.
References Cited (Backward Citations)
US3501456A
Cited
US4447600A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-08-31 | 1991-03-02 | 1991-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-31 | 1995-03-02 | 1995-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-31 | 1999-03-02 | 1999-09-01 | $7700.00 | Window Closed / Lapsed |