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EP0273388A2
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Sialic acid derivatives having active carbonyl group
Assignee: Mect Corp
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Filing: 1987-12-23
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Granted: —
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Expires: 2007-12-23
Abstract
Abstract A sialic acid derivative having an active carbonyl group represented by the formula [I]: <CHEM> (wherein R<1> represents hydrogen or acetyl group; R<2> represents hydrogen, a metal or a lower alkyl group; R<3> represents hydrogen, hydroxyl group, or a residue removed hydrogen from an alcohol portion of an active ester; Ac represents acetyl group; and n is 1 to 20, respectively). This sialic acid derivative [I] can be utilized as a starting material for various complex having a sialic acid in the molecule since it has an active carbonyl group in the molecule so that it shows high reactivity.
Inventors
- 👤 Shoji Yoshimura
- 👤 Shohei Shibayama
- 👤 Masaaki Numata
- 👤 Masayoshi Ito
- 👤 Yoshiyasu Shitori
- 👤 Tomoya Ogawa
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-23 15:16
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; A; A61; A61K; A61K31/00; A61K31/70; A61K31/715; A61K47/00; A61K47/06; A61K47/26; A61P; A61P43/00
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
64 words
(a) A sialic acid derivative having an active carbonyl group represented by the formula [I]: (wherein R 1 represents hydrogen or acetyl group; R 2 represents hydrogen, a metal or a lower alkyl group; R 3 represents hydrogen, hydroxyl group, or a residue removed hydrogen from an alcohol portion of an active ester; Ac represents acetyl group; and n is 1 to 20, respectively).
Claim 2
Dependent Claim
28 words
(2) The sialic acid derivative having an active carbonyl group according to Claim 1, wherein said compound is represented by the formula [la]: (wherein Ac represents acetyl group).
Claim 3
Dependent Claim
28 words
(3) The sialic acid derivative having an active carbonyl group according to Claim 1, wherein said compound is represented by the formula [Ih]: (wherein Ac represents acetyl group).
Claim 4
Dependent Claim
28 words
(4) The sialic acid derivative having an active carbonyl group according to Claim 1, wherein said compound is represented by the formula (li): (wherein Ac represents acetyl group).
Claim 5
Dependent Claim
28 words
(5) The sialic acid derivative having an active carbonyl group according to Claim 1, wherein said compound is represented by the formula (Ij]: (wherein Ac represents acetyl group).
Claim 6
Dependent Claim
28 words
(6) The sialic acid derivative having an active carbonyl group according to Claim 1, wherein said compound is represented by the formula [Ik]: (wherein Ac represents acetyl group).
Claim 7
Dependent Claim
28 words
(7) The sialic acid derivative having an active carbonyl group according to Claim 1, wherein said compound is represented by the formula [II]: (wherein Ac represents acetyl group).
Claim 8
Dependent Claim
37 words
(8) The sialic acid derivative having an active carbonyl group according to Claim 1, wherein an alcohol portion of an active ester is one selected from the group consisting of N-hydroxyphthalimide, N-hydroxybenzotriazole, p-nitrophenol, 2,4-dinitrophenol, 2,4,5-trichlorophenol and pentachlorophenol.
Claim 9
Dependent Claim
75 words
(9) A biological half-life elongating agent of a physiologically active substance comprising a sialic acid derivative having an active carbonyl group represented by the formula [I]: (wherein R 1 represents hydrogen or acetyl group; R 2 represents hydroger a metal or a lower alkyl group; R 3 represents hydrogen, hydroxyl group, or a residue removed hydrogen from an alcohol portion of an active ester; Ac represents acetyl group; and n is 1 to 20, respectively).
Claim 10
Dependent Claim
29 words
(10) The biological half-life elongating agent of a physiologically active substance according to Claim 9, wherein said compound is represented by the formula [Ih]: (wherein Ac represents acetyl group).
Claim 11
Dependent Claim
29 words
(11) The biological half-life elongating agent of a physiologically active substance according to Claim 9, wherein said compound is represented by the formula [li]: (wherein Ac represents acetyl group).
Claim 12
Dependent Claim
29 words
(12) The biological half-life elongating agent of a physiologically active substance according to Claim 9, wherein said compound is represented by the formula [Ij]: (wherein Ac represents acetyl group).
Claim 13
Dependent Claim
29 words
(13) The biological half-life elongating agent of a physiologically active substance according to Claim 9, wherein said compound is represented by the formula [Ik]: (wherein Ac represents acetyl group).
Claim 14
Dependent Claim
29 words
(14) The biological half-life elongating agent of a physiologically active substance according to Claim 9, wherein said compound is represented by the formula [II]: (wherein Ac represents acetyl group).
Claim 15
Dependent Claim
29 words
(15) The biological half-life elongating agent of a physiologically active substance according to Claim 9, wherein said compound is represented by the formula [Im]: (wherein Ac represents acetyl group).
Claim 16
Dependent Claim
40 words
(16) The biological half-life elongating agent of a physiologically active substance according to Claim 9, wherein an alcohol portion of an active ester is one selected from the group consisting of N-hydroxysuccinimide, N-hydroxy-5-norbornene-2,3-dicarboximide, N-hydroxyphthalimide, N-hydroxybenzotriazole, p-nitrophenol, 2,4-dinitrophenol, 2,4,5-trichlorophenol and pentachlorophenol.
Claim 17
Dependent Claim
75 words
(17) A binder of a coupling gel for affinity chromatography comprising a sialic acid derivative having an active carbonyl group represented by the formula [I]: (wherein R 1 represents hydrogen or acetyl group; R 2 represents hydrogen, a metal or a lower alkyl group; R 3 repre sents hydrogen, hydroxyl group, or a residue removed hydrogen from an alochol portion of an active ester; Ac represents acetyl group; and n is 1 to 20, respectively).
Claim 18
Dependent Claim
28 words
(18) The binder of a coupling gel for affinity chromatography according to Claim 17, wherein said compound is represented by the formula [Ih]: (wherein Ac represents acetyl group).
Claim 19
Dependent Claim
28 words
(19) The binder of a coupling gel for affinity chromatography according to Claim 17, wherein said compound is represented by the formula [li]: (wherein Ac represents acetyl group).
Claim 20
Dependent Claim
28 words
(20) The binder of a coupling gel for affinity chromatography according to Claim 17, wherein said compound is represented by the formula [Ij]: (wherein Ac represents acetyl group).
Claim 21
Dependent Claim
28 words
(21) The binder of a coupling gel for affinity chromatography according to Claim 17, wherein said compound is represented by the formula [Ik]: (wherein Ac represents acetyl group).
Claim 22
Dependent Claim
28 words
(22) The binder of a coupling gel for affinity chromatography according to Claim 17, wherein said compound is represented by the formula [II]: (wherein Ac represents acetyl group).
Claim 23
Dependent Claim
28 words
(23) The binder of a coupling gel for affinity chromatography according to Claim 17, wherein said compound is represented by the formula [Im]: (wherein Ac represents acetyl group).
Claim 24
Dependent Claim
41 words
(24) The binder of a coupling gel for affinity chromatography according to Claim 17, wherein an alcohol portion of arr active ester is one selected from the group consisting of N-hydroxysuccinimide. N-hydroxy-5-norbornene-2.3-dicarboximide, N-hydroxyphthalimide, N-hydroxybenzotriazole, p - nitrophenol, 2,4-dinitrophenol, 2,4,5-trichlorophenol and pentachlorophenol.
Claim 25
Dependent Claim
56 words
(25) A sialic acid derivative represented by the formula [II]: (wherein R 1 represents hydrogen or acetyl group; R 2 represents hydrogen, sodium or a lower alkyl group; Ac represents acetyl group; X represents a residue removed m amino group(s) from an amino compound; m is 1 to 60 and n is 1 to 20, respectively).
Claim 26
Dependent Claim
25 words
(26) The sialic acid derivative according to Claim 25, wherein X is a residue removed one amino group from an amino acid, or derivative thereof.
Claim 27
Dependent Claim
34 words
(27) The sialic acid derivative according to Claim 26, wherein said compound is represented by the formula [Ila]: (wherein -R 4 represents -CONH- CH -COOCH 3 ; and Ac represents CH3 acetyl group, respectively).
Claim 28
Dependent Claim
35 words
(28) The sialic acid derivative according to Claim 26, wherein said compound is represented by the formula [Ilb]: (wherein -R 5 represents ; and Ac represents acetyl group, respectively. Also, CBZ represents a benzyloxycarbonyl group.).
Claim 29
Dependent Claim
36 words
(29) The sialic acid derivative according to Claim 26, wherein said compound is represented by the formula [Ilc]: C H 3 (wherein -R 4 represents -CONH- C H - COOCH3; and Ac represents acetyl group, respectively).
Claim 30
Dependent Claim
35 words
(30) The sialic acid derivative according to Claim 26, wherein said compound is represented by the formula [IId]: (wherein -R 5 represents ; and Ac represents acetyl group, respectively. Also, CBZ represents a benzyloxycarbonyl group.).
Claim 31
Dependent Claim
38 words
(31) The sialic acid derivative according to Claim 26, wherein said compound is represented by the formula [Ile]: (wherein -R 4 represents -CONH- C H - COOCH 3 ; and Ac represents C H 3 acetyl group, respectively).
Claim 32
Dependent Claim
35 words
(32) The sialic acid derivative according to Claim 26, wherein said compound is represented by the formula [Ilf]: (wherein -R 6 represents -CONH- C H -COONa; and Ac represents C H 3 acetyl group, respectively).
Claim 33
Dependent Claim
37 words
(33) The sialic acid derivative according to Claim 26, wherein X is a residue removed 1 to 60 amino group from peptide or protein, or conjugated protein with which the above and a prosthetic group are combined.
Claim 34
Dependent Claim
30 words
(34) The sialic acid derivative according to Claim 33, wherein said compound is represented by the formula [IIg]: (wherein Ac represents acetyl group; and BSA represents Bovine Serum Albumin, respectively).
Claim 35
Dependent Claim
30 words
(35) The sialic acid derivative according to Claim 33, wherein said compound is represented by the formula [Ilh]: (wherein Ac represents acetyl group; and BSA represents Bovine Serum Albumin, respectively).
Claim 36
Dependent Claim
30 words
(36) The sialic acid derivative according to Claim 33, wherein said compound is represented by the formula [IIi]: (wherein Ac represents acetyl group; and BSA represents Bovine Serum Albumin, respectively).
References Cited (Backward Citations)
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