US4990603A
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Sialic acid derivatives and process therefor
Assignee: Mect Corp
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Filing: 1987-06-30
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Granted: 1991-02-05
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Expires: 2007-06-30
Abstract
Abstract The present invention relates to sialic acid derivatives. According to the present invention, there is provided sialic acid derivatives having the general formula (I): ##STR1## wherein, R 1 represents hydrogen, an acetyl group, a trityl group, ##STR2## (R 5 represents hydrogen or an acetyl group and R 6 represents hydrogen, sodium or a methyl group). R 2 represents hydrogen or an acetyl group, one of R 3 and R 4 represents ##STR3## (R 7 represents a hydrogen atom or an acetyl group, R 8 represents a hydrogen atom, an acetyl group or a benzyl group, R 9 represents a hydrogen atom, an acetyl group, a benzyl group or ##STR4## wherein R 10 represents a hydrogen atom or a benzoyl group), while the other represents --COOR 11 wherein R 11 represents hydrogen, sodium, or a methyl group.
Inventors
- 👤 Tomoya Ogawa
- 👤 Mamoru Sugimoto
- 👤 Masaaki Numata
- 👤 Shoji Yoshimura
- 👤 Masayoshi Ito
- 👤 Yoshiyasu Shitori
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 03:17
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; C07H15/10; C07H3/00; C07H3/06
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
115 words
A process for producing ganglioside GD 3 having the general formulae (8) and (9): ##STR15## (a) deacetylating a compound (3) having the following formula (3): ##STR16## , to produce a compound (4) having the following formula (4): ##STR17## (b) tritylating said compound (4), to produce a compound (5) having the following formula (5): ##STR18## wherein Tr is a trityl group, (c) acetylating said compound (5), to produce a compound (6) having the following formula (6): ##STR19## wherein Tr is defined above, (d) detritylating said compound (6), to produce a compound (7) having the following formula (7): ##STR20## , and then (e) reacting said compound (7) with a compound (2) having the following formula (2): ##STR21##
Claim 2
Dependent Claim
115 words
A process for producing ganglioside GD 3 having the general formulae (8) and (9): ##STR15## (a) deacetylating a compound (3) having the following formula (3): ##STR16## , to produce a compound (4) having the following formula (4): ##STR17## (b) tritylating said compound (4), to produce a compound (5) having the following formula (5): ##STR18## wherein Tr is a trityl group, (c) acetylating said compound (5), to produce a compound (6) having the following formula (6): ##STR19## wherein Tr is defined above, (d) detritylating said compound (6), to produce a compound (7) having the following formula (7): ##STR20## , and then (e) reacting said compound (7) with a compound (2) having the following formula (2): ##STR21##
Claim 3
Dependent Claim
120 words
A process for producing a compound (7) having the following formula (7): ##STR22## wherein ##STR23## is an OAc group and ##STR24## is an OBn group (Bn is a benzyl group), comprising: (a) deallylating a compound (1) having the following formula (1): ##STR25## wherein ##STR26## is defined above, to produce a compound (2) having the following formula (2): ##STR27## wherein ##STR28## is defined above, (b) chlorinating said compound (2) to produce a compound (3) having the following formula (3): ##STR29## wherein ##STR30## is defined above, (c) reacting said compound (3) with benzyl lactose, to produce compounds (4) and (5) having the following formulae (4) and (5): ##STR31## wherein ##STR32## and ##STR33## are defined above, and then (d) acetylating said compound (5).
Claim 4
Dependent Claim
120 words
A process for producing a compound (7) having the following formula (7): ##STR22## wherein ##STR23## is an OAc group and ##STR24## is an OBn group (Bn is a benzyl group), comprising: (a) deallylating a compound (1) having the following formula (1): ##STR25## wherein ##STR26## is defined above, to produce a compound (2) having the following formula (2): ##STR27## wherein ##STR28## is defined above, (b) chlorinating said compound (2) to produce a compound (3) having the following formula (3): ##STR29## wherein ##STR30## is defined above, (c) reacting said compound (3) with benzyl lactose, to produce compounds (4) and (5) having the following formulae (4) and (5): ##STR31## wherein ##STR32## and ##STR33## are defined above, and then (d) acetylating said compound (5).
Claim 5
Dependent Claim
184 words
A process for producing a compound having the following formula (13): ##STR34## comprising: (a) acetylating a compound (4) having the following formula (4): ##STR35## wherein ##STR36## is an OAc group and ##STR37## is an OBn group (Bn is a benzyl group), to produce a compound (6) having the following formula (6): ##STR38## wherein ##STR39## and ##STR40## are defined above, and then (b) debenzylating said compound (6), to produce a compound (8) having the following formula (8): ##STR41## wherein ##STR42## is defined above. (c) acetylating said compound (8), to produce a compound (9) having the following formula (9): ##STR43## wherein ##STR44## is defined above, (d) selectively deacetylating said compound (9), to produce a compound (10) having the following formula (10): ##STR45## wherein ##STR46## is defined above, (e) reacting said compound (10) with trichloroacetonitrile to produce a compound (11) having the following formula (11): ##STR47## wherein ##STR48## is defined above, (f) reacting said compound (11) with benzoylceramide, to produce a compound (12) having the following formula (12): ##STR49## wherein ##STR50## is defined above and Bz is a benzoyl group, and then (g) hydrolyzing said compound (12).
Claim 6
Dependent Claim
184 words
A process for producing a compound having the following formula (13): ##STR34## comprising: (a) acetylating a compound (4) having the following formula (4): ##STR35## wherein ##STR36## is an OAc group and ##STR37## is an OBn group (Bn is a benzyl group), to produce a compound (6) having the following formula (6): ##STR38## wherein ##STR39## and ##STR40## are defined above, and then (b) debenzylating said compound (6), to produce a compound (8) having the following formula (8): ##STR41## wherein ##STR42## is defined above. (c) acetylating said compound (8), to produce a compound (9) having the following formula (9): ##STR43## wherein ##STR44## is defined above, (d) selectively deacetylating said compound (9), to produce a compound (10) having the following formula (10): ##STR45## wherein ##STR46## is defined above, (e) reacting said compound (10) with trichloroacetonitrile to produce a compound (11) having the following formula (11): ##STR47## wherein ##STR48## is defined above, (f) reacting said compound (11) with benzoylceramide, to produce a compound (12) having the following formula (12): ##STR49## wherein ##STR50## is defined above and Bz is a benzoyl group, and then (g) hydrolyzing said compound (12).
Claim 7
Dependent Claim
48 words
A process for producing a compound (7) having the following formula (7): ##STR51## wherein ##STR52## is an OAc group and ##STR53## is an OBn group (Bn is a benzyl group), comprising acetylating a compound (6) having the following formula (6): ##STR54## wherein ##STR55## and ##STR56## are defined above.
Claim 8
Dependent Claim
48 words
A process for producing a compound (7) having the following formula (7): ##STR51## wherein ##STR52## is an OAc group and ##STR53## is an OBn group (Bn is a benzyl group), comprising acetylating a compound (6) having the following formula (6): ##STR54## wherein ##STR55## and ##STR56## are defined above.
Claim 9
Dependent Claim
39 words
The process of claim 4, wherein said compound (6) is one of the compounds obtained by reacting benzyl lactose with a compound (3) or (4) having the following formula (3) or (4). ##STR57## wherein ##STR58## is an OAc group.
Claim 10
Dependent Claim
28 words
The process of claim 5, wherein said compound (4) is obtained by pyridylsulfidizing a compound (2) having the following formula (2): ##STR59## wherein ##STR60## is an OAc group.
Claim 11
Dependent Claim
182 words
A process for producing a compound (14) having the following formula (14): ##STR61## comprising: (a) acetylating a compound (5) having the following formula (5): ##STR62## wherein ##STR63## is an OAc group and ##STR64## is an OBn group (Bn is a benzyl group), to produce a compound (8) having the following formula (8): ##STR65## wherein ##STR66## and ##STR67## are defined above, (b) debenzylating said compound (8), to produce a compound (9) having the following formula (9): ##STR68## wherein ##STR69## is defined above, (c) acetylating said compound (9), to produce a compound (10) having the following formula (10): ##STR70## wherein ##STR71## is defined above, (d) deacetylating said compound (10), to produce a compound (11) having the following formula (11): ##STR72## wherein ##STR73## is defined above, (e) reacting said compound (11) with Cl 3 CCN, to produce a compound (12) having the following formula (12): ##STR74## wherein ##STR75## is defined above, (f) reacting said compound (12) with benzoylceramide, to produce a compound (13) having the following formula (13): ##STR76## wherein ##STR77## is defined above, and then (g) deactylating, debenzylating and then saponifying said compound (13).
Claim 12
Dependent Claim
182 words
A process for producing a compound (14) having the following formula (14): ##STR61## comprising: (a) acetylating a compound (5) having the following formula (5): ##STR62## wherein ##STR63## is an OAc group and ##STR64## is an OBn group (Bn is a benzyl group), to produce a compound (8) having the following formula (8): ##STR65## wherein ##STR66## and ##STR67## are defined above, (b) debenzylating said compound (8), to produce a compound (9) having the following formula (9): ##STR68## wherein ##STR69## is defined above, (c) acetylating said compound (9), to produce a compound (10) having the following formula (10): ##STR70## wherein ##STR71## is defined above, (d) deacetylating said compound (10), to produce a compound (11) having the following formula (11): ##STR72## wherein ##STR73## is defined above, (e) reacting said compound (11) with Cl 3 CCN, to produce a compound (12) having the following formula (12): ##STR74## wherein ##STR75## is defined above, (f) reacting said compound (12) with benzoylceramide, to produce a compound (13) having the following formula (13): ##STR76## wherein ##STR77## is defined above, and then (g) deactylating, debenzylating and then saponifying said compound (13).
Claim 13
Dependent Claim
39 words
The process of claim 7, wherein said compound (5) is one of the compounds obtained by reacting benzyl lactose with a compound (3) or (4) having the following formula (3) or (4): ##STR78## wherein ##STR79## is an OAc group.
Claim 14
Dependent Claim
28 words
The process of claim 8, wherein said compound (4) is obtained by pyridylsulfidizing a compound (2) having the following formula (2): ##STR80## wherein ##STR81## is an OAc group.
Claim 15
Dependent Claim
72 words
A sialic acid derivative having the formula (I): ##STR82## wherein R 1 represents ##STR83## (R 5 represents hydrogen or an acetyl group and R 6 represents hydrogen, sodium or a methyl group) R 2 represents hydrogen or an acetyl group, one of R 3 and R 4 represents --OCH 2 CHCH 2 , or ##STR84## while the other represents -COOR 11 , wherein R 11 represents hydrogen, sodium or a methyl group.
Claim 16
Dependent Claim
72 words
A sialic acid derivative having the formula (I): ##STR82## wherein R 1 represents ##STR83## (R 5 represents hydrogen or an acetyl group and R 6 represents hydrogen, sodium or a methyl group) R 2 represents hydrogen or an acetyl group, one of R 3 and R 4 represents --OCH 2 CHCH 2 , or ##STR84## while the other represents -COOR 11 , wherein R 11 represents hydrogen, sodium or a methyl group.
Claim 17
Dependent Claim
112 words
A sialic acid derivative having the formula (I): ##STR85## wherein R 1 represents hydrogen, an acetyl group, a trityl group, ##STR86## (R 5 represents hydrogen or an acetyl group and R 6 represents hydrogen, sodium or a methyl group) R 2 represents hydrogen or an acetyl group, one of R 3 and R 4 represents ##STR87## (R 7 represents hydrogen or an acetyl group, R 8 represents hydrogen, an acetyl group or a benzyl group, R 9 represents hydrogen, an acetyl group, a benzyl group or ##STR88## wherein R 10 represents hydrogen or a benzoyl group), while the other represents -COOR 11 wherein R 11 represents hydrogen, sodium, or a methyl group.
Claim 18
Dependent Claim
112 words
A sialic acid derivative having the formula (I): ##STR85## wherein R 1 represents hydrogen, an acetyl group, a trityl group, ##STR86## (R 5 represents hydrogen or an acetyl group and R 6 represents hydrogen, sodium or a methyl group) R 2 represents hydrogen or an acetyl group, one of R 3 and R 4 represents ##STR87## (R 7 represents hydrogen or an acetyl group, R 8 represents hydrogen, an acetyl group or a benzyl group, R 9 represents hydrogen, an acetyl group, a benzyl group or ##STR88## wherein R 10 represents hydrogen or a benzoyl group), while the other represents -COOR 11 wherein R 11 represents hydrogen, sodium, or a methyl group.
References Cited (Backward Citations)
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