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1. 发明专利

JPS60123494A SIALIC ACID-CONTAINING OLIGOSACCHARIDE AND ITS PREPARATION 失效
公开(公告)号：JPS60123494A
公开(公告)日：1985-07-02
申请号：JP23204383
申请日：1983-12-08
申请人： RIKAGAKU KENKYUSHO , TOUWA KASEI KOGYO KK , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , NUKADA YASUO , KITAJIMA TOORU , SUGIMOTO MAMORU , TAKEMURA MOTOHIRO , SHIDORI YOSHIYASU
IPC分类号： C07H7/02 , C07H3/06 , C07H7/027 , C07H15/18
摘要： NEW MATERIAL:A compound shown by the formula I or formula II (R1 is H, or methyl; R2 is H, or acetyl; R3 is H, or benzyl). USE:An immune adjusting agent. Having no side effects. PREPARATION:A saccharide acceptor shown by the formula III Ac is acetyl; Bn is benzyl) is reacted with a saccharide donor shown by the formula IV (X is halogen) in a solvent such as dichloromethane, etc. in the presence of glycosidation catalyst such as Hg(CN)2, etc. preferably at -20-150 deg.C for 1-120hr. If necessary, the reaction product is deacetylated, saponified, or debenzylated.

2. 发明专利

JPS63104986A CERAMIDE-RELATING COMPOUND 失效
公开(公告)号：JPS63104986A
公开(公告)日：1988-05-10
申请号：JP24898186
申请日：1986-10-20
申请人： RIKAGAKU KENKYUSHO , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , NUMATA MASAAKI , SUGIMOTO MAMORU , ITO MASAYOSHI , SHIDORI YOSHIYASU
IPC分类号： C07F7/18
摘要： NEW MATERIAL:A compound expressed by formula I (R represents H or trityl; R1 and R2 represent methyl or phenyl; R3 represents tertiary butyl or dimetylphenylmerhyl). USE:An intermediate for synthesis of gangliosides. PREPARATION:For example, a ceramide compound expressed by formula II is treated with trityl chloride in pyridine to form a trityl derivative, and reacted with a compound expressed by the formula R1R2R3SiCl [example; dimethyl (trimethylmethylphenyl)silyl chloride, etc.] in dimethylformamide to afford a compound expressed by formula III (Ph represents phenyl; Me represents methyl). Then the compound is hydrolyzed in a methylene chloride-methanol mixed solvent to afford the compound expressed by formula I.

3. 发明专利

JPS6341491A GANGLIOSIDE GM1-RELATED COMPOUND AND PRODUCTION THEREOF 失效
公开(公告)号：JPS6341491A
公开(公告)日：1988-02-22
申请号：JP18450186
申请日：1986-08-06
申请人： RIKAGAKU KENKYUSHO , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , SUGIMOTO MAMORU , NUMATA MASAAKI , ITO MASAYOSHI , SHIDORI YOSHIYASU
IPC分类号： C07H13/04 , C07H15/04 , C07H15/10 , C07H19/04
摘要： NEW MATERIAL:A compound expressed by formula I (R1 is H or acetyl; R2 is H or CH3; R3 is OH, etc.). EXAMPLE:A compound expressed by formula II. USE:A biochemical reagent in basic biology, etc. The titled compound has membranous receptor function, cell growth regulating activity and nerve cell growth promoting activity. PREPARATION:A compound expressed by formula III (AC is acetyl; Bn is formula IV) is reacted with a compound expressed by formula V. The resultant reaction product is successively subjected to demethylation, conversion of phthalic imide group thereof into amino group, acetylation, conversion of carboxyl group to methyl ester group, debenzoylation and acetylation. Then the product is treated with hydrazinium acetate, OCl3CN and NaH. The treated product is reacted with a compound expressed by formula VII and the reaction product is subjected to debenzoylation, deacetylation and demethylation.

4. 发明专利

JPS6314792A NEUACALPHA-9NEUAC SUGAR DONOR AND PRODUCTION THEREOF 失效
公开(公告)号：JPS6314792A
公开(公告)日：1988-01-21
申请号：JP15764686
申请日：1986-07-04
申请人： RIKAGAKU KENKYUSHO , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , SUGIMOTO MAMORU , NUMATA MASAAKI , YOSHIMURA SHOJI , ITO MASAYOSHI , SHIDORI YOSHIYASU
IPC分类号： C07H15/04 , C07H3/02 , C07H3/04 , C07H7/027 , C07H13/06 , C07H15/10 , C07H15/18
摘要： NEW MATERIAL:The sialic acid derivative of formula I (Ac is acetyl; R is H, acetyl, trityl, group of formula II, etc.; R is H or acetyl; one of R and R is Cl, OAc or group of formula OCH2CH=CH2 and the other is group of formula COOCH3). USE:Synthetic intermediate for ganglioside useful as a tumor marker and cell differentiation marker. PREPARATION:The compound of formula I can be produced e.g. by chlorinating the compound of formula III with HCl gas in acetyl chloride under ice cooling, allylating the resultant compound of formula IV with allyl alcohol and silver salicylate, subjecting the product successively to deacetylation, tritylation, acetylation and detritylation and reacting the resultant product with the compound of formula IV.

5. 发明专利

JPS6112697A Galactose derivative 失效
标题翻译： GALACTOSE DERIVATIVE
公开(公告)号：JPS6112697A
公开(公告)日：1986-01-21
申请号：JP13388284
申请日：1984-06-28
申请人： Kanto Ishi Pharma Co Ltd , Rikagaku Kenkyusho
发明人： OGAWA TOMOYA , SUGIMOTO MAMORU , SHIDORI YOSHIYASU , ITOU MASAYOSHI
IPC分类号： C07H15/18 , C07H5/06 , C07H15/00 , C07H15/10
摘要： NEW MATERIAL:A compound shown by the formula I [R
2 is H, or benzyl, when R
1 is benzyl; R
2 is H, acetyl, or benzyl when R
1 is group shown by the formula II(R
3 and R
4 are H or linked to form isopropylidene; R
5 is benzyl, or allyl; R
6 is H, acetyl, or benzyl)].
USE: Useful for synthesizing various gangliosides suitable as a differentiation marker of cell.
PREPARATION: For example, a galactose derivative of the aimed compound is synthesized from D-lactose octaacetate (1) (OAC group) corresponding to the reaction equations (OBn group), to give compounds shown by the formula (8) and formula (9).
COPYRIGHT: (C)1986,JPO&Japio
摘要翻译：新材料：由式I表示的化合物[R 2为H或苄基，当R 1为苄基时）当R 1为式II所示基团时，R 2为H，乙酰基或苄基（R 3和R 4为H或连接形成异亚丙基; R 5为苄基或烯丙基; R 6为H，乙酰基或苄基）]。用途：用于合成适合作为细胞分化标志物的各种神经节苷脂。制备：例如，由对应于反应式（OBn组）的D-乳糖八乙酸酯（1）（OAC基）合成目标化合物的半乳糖衍生物，得到式（8）和式（9）所示的化合物）。

6. 发明专利

JPS60190787A Sialic acid derivative and its preparation 失效
标题翻译：酸性衍生物及其制备方法
公开(公告)号：JPS60190787A
公开(公告)日：1985-09-28
申请号：JP4490584
申请日：1984-03-09
申请人： Kanto Ishi Pharma Co Ltd , Rikagaku Kenkyusho
发明人： OGAWA TOMOYA , FUJIKURA KAZUSHIGE , SUGIMOTO MAMORU , SHIDORI YOSHIYASU , ITOU MASAYOSHI
IPC分类号： C07H15/10 , A61K31/70 , A61K31/7028 , A61P31/04 , C07H15/04 , C07H15/18
CPC分类号： Y02P20/55
摘要： NEW MATERIAL:A compound shown by the formula I (R
1 is H, or CH
3 ; R
2 is acyl, or n-propyl; R
3 and R
4 are H, D-glucopyranosyl, 2,3,4-tri-O-benzyl-D-glycopyranosyl, 2,3,4-tri-O-benzyl-6-O-monochloroacetyl-D-glucopyranosyl, benzoyl, or benzyl; R
5 and R
6 are linked to form isopropylidene, or benzylidene; Ac is acetyl).
USE: A remedy for meningitis.
PREPARATION: A compound shown by the formula II is deacetylated, reacted with 2,2-dimethoxypropane to give a novel compound shown by formula III, which is reacted with a compound shown by the formula IV (X is halogen, Br is benzyl; MCA is monochloroacetyl) in a solvent such as 1,2-dichloroethane, etc. in the presence of glycosidation catalyst such as Hg(CH)
2 , etc. at -20W150°C for 1W120hr, and if necessary, the protecting group is removed, or reduced, to give a compound shown by the formula I .
COPYRIGHT: (C)1985,JPO&Japio
摘要翻译：新材料：由式I表示的化合物（R1为H或CH3; R2为酰基或正丙基; R3和R4为H，D-吡喃葡萄糖基，2,3,4-三-O-苄基-D - 吡喃葡萄糖基，2,3,4-三-O-苄基-6-O-单氯乙酰基-D-吡喃葡萄糖基，苯甲酰基或苄基; R5和R6连接形成异亚丙基或亚苄基; Ac是乙酰基。使用：脑膜炎的补救措施。制备：式II化合物脱乙酰化，与2,2-二甲氧基丙烷反应，得到式III所示的新化合物，其与式IV化合物（X为卤素，Br为苄基; MCA 是一氯乙酰基）在溶剂如1,2-二氯乙烷等中，在糖化催化剂如Hg（CH）2等存在下，在-20-150℃下反应1-120小时，如果需要，除去或还原保护基，得到式I所示的化合物。

7. 发明专利

JPH04363302A POLYLACTOSAMINE TYPE GLYCOLIPID 失效
公开(公告)号：JPH04363302A
公开(公告)日：1992-12-16
申请号：JP24231691
申请日：1991-08-29
申请人： RIKAGAKU KENKYUSHO , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , ITO YUKINARI , MATSUZAKI YUJI , SUGIMOTO MAMORU
IPC分类号： A61K31/715 , A61P35/00 , C07H3/04 , C07H3/06 , C07H15/04 , C07H15/10 , C08B37/00
摘要： PURPOSE:To provide the subject new polylactosamine type glycolipid having a branched structure on a lactosamine molecule and useful for diagnosis, therapy, etc., of cancer. CONSTITUTION:A I type polylactosamine type glycolipid of formula I (R is protectable OH; R is protectable amino group). The above-mentioned glycolipid can be obtained by reacting a compound of formula II (Phth is phthaloyl) with a compound of formula III (Piv is pivaloyl; Bn is benzyl; Ac is acetyl) in the presence of SnCL2/AgClO4, etc., in a solvent such as CCl4, hydrogenating the resultant compound of formula IV in the presence of Pd/C catalyst in a solvent such as methanol, then reacting the obtained reactional product in the presence of hydrazine acetate and 1,8-diazabicyclo(5,4,0)undecene-7 in order, subsequently reacting the resultant compound of formula V with a compound of formula VI in the presence of pyridinium para-toluenesulfonate, etc., in a solvent such as toluene and further reacting the reactional product with AC2O.

8. 发明专利

JPH0278694A NOVEL SIALIC ACID DONOR, PREPARATION THEREOF AND PREPARATION OF STEREOSELECTIVE GLYCOSIDE USING THE SAME SIALIC ACID DONOR 失效
公开(公告)号：JPH0278694A
公开(公告)日：1990-03-19
申请号：JP22793888
申请日：1988-09-12
申请人： RIKAGAKU KENKYUSHO , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , ITO YUKINARI , SUGIMOTO MAMORU
IPC分类号： C07H15/203
摘要： NEW MATERIAL:An alpha type sialic acid donor compound of formula I (R is lower alkyl; Bn is benzyl; Ac is acetyl; Ph is phenyl). USE:For the preparation of alpha-glycosides. The alpha-glycosides can be obtained selectively in high yields. PREPARATION:A compound of formula II is deacetylated and subsequently benzylated to prepare a compound of formula III, which is esterified with a lower alkyl and reacted with a halogenating agent to give a compound of formula IV [R is COOR or OH; R is OH or COOR; R is X (X is halogen) or H; R is H or X]. The compound of formula IV is reacted with thiophenol in the presence of a base and further treated with the base to give a compound of formula V, followed by halogenating the compound of formula V.

9. 发明专利

JPH0477496A SYNTHESIS OF OLIGOPEPTIDE CONTAINING NEUACALPHA2- 6GA1NACALPHA1-3SER STRUCTURE 失效
公开(公告)号：JPH0477496A
公开(公告)日：1992-03-11
申请号：JP18989290
申请日：1990-07-18
申请人： RIKAGAKU KENKYUSHO , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , NAKAHARA YOSHIAKI , IIJIMA HIROYUKI , SHIBAYAMA SHOHEI , SUGIMOTO MAMORU
IPC分类号： C07H15/04 , C07K1/02 , C07K1/113 , C07K9/00
摘要： PURPOSE:To synthesize in large quantities an oligopeptide containing a basal saccharide chain of mutin type sugar protein such as glycophorin which is a human erythrocyte membraneous glycoprotein as the basal unit by reacting specific two kinds of raw material compounds. CONSTITUTION:A compound expressed by formula I (Bn is benzyl; Ac is acetyl; (n) is 1-4 is made to react with a compound expressed by formula II (Fmoc is formula III). Thereby the glycopeptide chain is elongated to provide the objective compound expressed by formula IV ((n) is 2-5).

10. 发明专利

JPH03264597A INTERMEDIATE FOR SYNTHESIZING GLOBO GLUCOLIPID 失效
公开(公告)号：JPH03264597A
公开(公告)日：1991-11-25
申请号：JP6358690
申请日：1990-03-14
申请人： RIKAGAKU KENKYUSHO , KANTO ISHI PHARMA CO LTD
发明人： OGAWA TOMOYA , ITO YUKINARI , NUNOMURA SHIGEKI
IPC分类号： C07H13/08 , C07H15/10
摘要： NEW MATERIAL:A globo glucolipid of formula I (Ac is acetyl; X is OAc, OH, F; the group of formula II is OCOCH3). USE:An intermediate for synthesizing Forssman antigen used as a diagnostic drug or treating drug for cancer tissues. PREPARATION:For example, an azide monosaccharide of formula III is reacted with an azide monosacccharide of formula IV (Ph is phenyl), subjected to a reaction for removing the protecting group of the hydroxyl group and reacted with phthalic anhydride to convert the azide group into a phthalic imide group. The product is treated with acetic acid in the presence of PdCl2, etc., and the produced disaccharide of formula V (NPhth is phthalimide group; X is acetoxy, etc.) is subjected to a trimethylsilylation reaction, to a reaction with a trisaccharide of formula VI, to a phthaloyl group-removing reaction, to an acetylation, to a debenzylation and subsequently to an acetylation reaction to provide the globo glucolipid of formula I.

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